{ "Abnormal Beckmann rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.016508254127063533, 0.10973208123048867, 0.1790895447723862, 0.9200612964710203 ], "category_id": 1, "smiles": "*/C([2*])=N/O", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 4.9694 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1640 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3311 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9694 -2.2283 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1640 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\nM ISO 1 2 2\nA 2\nR2\nA 3\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.24062031015507754, 0.11817301055591087, 0.3051525762881441, 0.4895739008744879 ], "category_id": 2, "text": [ "H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3791895947973987, 0.2982461694982512, 0.592296148074037, 0.7231062788778356 ], "category_id": 1, "smiles": "[1*]N#C[2*]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 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0.5167583791895948, 0.043200171514328596, 0.704352176088044, 0.4408632887872508 ], "category_id": 1, "smiles": "[H]C1(C(C=C)CC)C=CC=CC1=O", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 4.1965 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2535 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2535 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3929 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4500 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1965 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2535 -6.3228 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1965 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0571 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0571 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0571 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 1 0\n 6 12 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5167583791895948, 0.043200171514328596, 0.704352176088044, 0.4408632887872508 ], "category_id": 1, "smiles": "[H]C1(C(C=C)CC)C=CC=CC1=O", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 4.1965 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2535 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2535 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3929 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4500 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1965 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2535 -6.3228 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1965 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0571 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0571 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0571 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 1 0\n 6 12 1 0\n 8 9 2 0\n 9 10 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0 0 0 0 0 0 0 0 0 0\n 5.9673 -1.2047 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 2.1584 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2539 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2539 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1584 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9673 -7.8189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0930 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.9974 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1571 -8.2913 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 12.1885 -4.8268 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 12.1885 -5.2205 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 6.6021 0.2913 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 17 1 0\n 5 6 1 0\n 5 7 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 16 2 0\n 9 10 2 0\n 9 15 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\n 17 18 2 0\nM CHG 5 11 -1 19 -1 20 -1 21 -1 22 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7493746873436719, 0.0585675522830424, 0.9624812406203102, 0.27945089232194514 ], "category_id": 1, "smiles": "O=C(c1ccccc1[O-])C1OC1c1ccccc1.[I-].[I-].[I-].[I-]", "molfile": "\n RDKit 2D\n\n 22 20 0 0 0 0 0 0 0 0999 V2000\n 15.9974 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0930 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0616 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0616 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1571 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0144 -6.4016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8718 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9673 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0628 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0628 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9673 -1.2047 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 2.1584 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2539 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2539 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1584 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9673 -7.8189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0930 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.9974 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1571 -8.2913 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 12.1885 -4.8268 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 12.1885 -5.2205 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 6.6021 0.2913 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 17 1 0\n 5 6 1 0\n 5 7 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 16 2 0\n 9 10 2 0\n 9 15 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\n 17 18 2 0\nM CHG 5 11 -1 19 -1 20 -1 21 -1 22 -1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2381190595297649, 0.4133195832546135, 0.32066033016508255, 0.4660303803093516 ], "category_id": 2, "text": [ "B-attack" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.35167583791895946, 0.3329983686950125, 0.5352676338169085, 0.5756353710104739 ], "category_id": 1, "smiles": "O=C1c2ccccc2OC(c2ccccc2)C1O", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n 12.4643 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6695 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9743 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9743 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1795 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4843 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7892 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7892 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9943 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2991 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2991 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9943 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4843 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4843 -8.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1795 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9743 -6.2441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6695 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4643 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 17 1 0\n 5 6 1 0\n 5 15 1 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 8 13 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 13 14 2 0\n 13 15 1 0\n 15 16 1 0\n 17 18 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.35167583791895946, 0.3329983686950125, 0.5352676338169085, 0.5756353710104739 ], "category_id": 1, "smiles": "O=C1c2ccccc2OC(c2ccccc2)C1O", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n 12.4643 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6695 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9743 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9743 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1795 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4843 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7892 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7892 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9943 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2991 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2991 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9943 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4843 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0.3171014616467581, 0.8329164582291145, 0.557228426007232 ], "category_id": 1, "smiles": "O=c1c(O)c(-c2ccccc2)oc2ccccc12", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n 12.3760 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6793 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9826 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9826 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1861 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4894 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6928 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6928 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9961 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2994 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2994 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9961 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4894 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4894 -8.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1861 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9826 -6.2441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6793 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.3760 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 17 1 0\n 5 6 1 0\n 5 15 2 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 8 13 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 13 14 2 0\n 13 15 1 0\n 15 16 1 0\n 17 18 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2226113056528264, 0.7722550108178304, 0.4307153576788394, 0.9755680851718206 ], "category_id": 1, "smiles": "O=C(c1ccccc1[O-])C1OC1c1ccccc1.O=C(c1ccccc1[O-])C1OC1c1ccccc1", "molfile": "\n RDKit 2D\n\n 36 40 0 0 0 0 0 0 0 0999 V2000\n 6.3415 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3415 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3176 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2937 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2698 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2698 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2937 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3176 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 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0 0\n 0.3476 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3476 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0859 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0259 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6053 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9788 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4852 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 17 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 16 1 0\n 5 6 2 0\n 6 7 1 0\n 6 14 1 0\n 7 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 9 14 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 2 0\n 16 17 2 0\nM END\n" } ] } ], "Allan\u2013Robinson reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03751875937968985, 0.10669334667333667, 0.18009004502251125, 0.39501941446913935 ], "category_id": 1, "smiles": "*CC(=O)c1ccccc1O", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 9.3611 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6274 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0947 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8283 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6605 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3942 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3942 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6605 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8283 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0947 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0947 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 11 2 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\nA 2\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.192096048024012, 0.17528192667762454, 0.29814907453726863, 0.2400600300150075 ], "category_id": 2, "text": [ "enolization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.2671335667833917, 0.06477810333738299, 0.5342671335667833, 0.4788499011410467 ], "category_id": 1, "smiles": "*/C=C(\\O[H])c1ccccc1O.[1*]C(=O)OC([1*])=O", "molfile": "\n RDKit 2D\n\n 19 18 0 0 0 0 0 0 0 0999 V2000\n 9.7989 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3461 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2517 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2517 -5.3780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7045 -6.3228 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7045 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1573 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6101 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6101 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1573 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7045 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2517 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1826 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1826 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6354 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6354 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0882 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1826 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.7298 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 3 6 1 0\n 4 5 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 13 14 1 0\n 13 15 1 0\n 13 19 2 0\n 15 16 1 0\n 16 17 1 0\n 16 18 2 0\nM ISO 2 14 1 17 1\nA 2\nR\nA 14\nR1\nA 17\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2671335667833917, 0.06477810333738299, 0.5342671335667833, 0.4788499011410467 ], "category_id": 1, "smiles": "*/C=C(\\O[H])c1ccccc1O.[1*]C(=O)OC([1*])=O", "molfile": "\n RDKit 2D\n\n 19 18 0 0 0 0 0 0 0 0999 V2000\n 9.7989 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3461 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2517 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2517 -5.3780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7045 -6.3228 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7045 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1573 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6101 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6101 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1573 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7045 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2517 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6354 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0882 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6354 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1826 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1826 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.7298 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1826 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 3 6 1 0\n 4 5 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 13 14 1 0\n 13 15 1 0\n 13 19 2 0\n 15 16 1 0\n 16 17 1 0\n 16 18 2 0\nM ISO 2 14 1 17 1\nA 2\nR\nA 14\nR1\nA 17\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5492746373186593, 0.1625803377879416, 0.6398199099549775, 0.23878987112603922 ], "category_id": 2, "text": [ "acylation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6623311655827914, 0.0609676266704781, 0.8599299649824912, 0.3861283022463613 ], "category_id": 1, "smiles": "*C(C(=O)c1ccccc1O)C([1*])(O)OC([1*])=O", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 0.2430 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2430 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3086 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3743 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4399 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3840 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4497 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3840 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4497 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1690 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4497 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4399 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3743 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3743 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3086 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 5 12 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\n 13 14 1 0\n 13 15 2 0\nM ISO 1 10 1\nA 7\nR\nA 9\nOCOR1\nA 10\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6623311655827914, 0.0609676266704781, 0.8599299649824912, 0.3861283022463613 ], "category_id": 1, "smiles": "*C(C(=O)c1ccccc1O)C([1*])(O)OC([1*])=O", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 0.2430 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2430 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3086 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3743 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4399 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3840 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4497 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3840 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4497 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1690 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4497 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4399 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3743 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3743 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3086 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 5 12 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\n 13 14 1 0\n 13 15 2 0\nM ISO 1 10 1\nA 7\nR\nA 9\nOCOR1\nA 10\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8724362181090545, 0.11939493556301961, 0.9634817408704353, 0.21211653445770504 ], "category_id": 2, "text": [ "OzCRI" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.07953976988494248, 0.5588699111460492, 0.3246623311655828, 0.9246756711689178 ], "category_id": 1, "smiles": "*.*.*C([H])(C([4*])=O)C(=O)c1ccccc1O", "molfile": "\n RDKit 2D\n\n 17 15 0 0 0 0 0 0 0 0999 V2000\n 0.2674 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2674 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0057 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7441 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4824 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2207 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9590 -4.9055 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2207 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2207 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2847 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2264 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4824 -6.9528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7441 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7441 0.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0057 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9008 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7031 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 5 12 2 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 2 0\n 13 14 1 0\n 13 15 2 0\nM ISO 1 10 4\nA 8\nR\nA 10\nR4\nA 16\nO2CRf\nA 17\nO2CRf\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.07953976988494248, 0.5588699111460492, 0.3246623311655828, 0.9246756711689178 ], "category_id": 1, "smiles": "*.*.*C([H])(C([4*])=O)C(=O)c1ccccc1O", "molfile": "\n RDKit 2D\n\n 17 15 0 0 0 0 0 0 0 0999 V2000\n 0.2674 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2674 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0057 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7441 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4824 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2207 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9590 -4.9055 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2207 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2207 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1510 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2264 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4824 -6.9528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7441 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7441 0.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0057 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9008 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7031 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 5 12 2 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 2 0\n 13 14 1 0\n 13 15 2 0\nM ISO 1 10 4\nA 8\nR\nA 10\nR4\nA 16\nO2CRf\nA 17\nO2CRf\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2416208104052026, 0.6655632578193859, 0.34817408704352176, 0.7405026322685153 ], "category_id": 2, "text": [ "enolization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.36218109054527264, 0.5601400700350175, 0.5097548774387194, 0.929756306724791 ], "category_id": 1, "smiles": "*/C(C([1*])=O)=C(\\O)c1ccccc1O[H]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 0.2394 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2394 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9949 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6706 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4260 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4260 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1815 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9370 -6.0079 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1815 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1442 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0966 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6706 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6706 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9949 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9949 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 1 0\n 12 15 2 0\n 13 14 1 0\nM ISO 1 10 1\nA 8\nR\nA 10\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.36218109054527264, 0.5601400700350175, 0.5097548774387194, 0.929756306724791 ], "category_id": 1, "smiles": "*/C(C([1*])=O)=C(\\O)c1ccccc1O[H]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 0.2394 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2394 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9949 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6706 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4260 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4260 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1815 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9370 -6.0079 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1815 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1442 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0966 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6706 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6706 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9949 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9949 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 1 0\n 12 15 2 0\n 13 14 1 0\nM ISO 1 10 1\nA 8\nR\nA 10\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5487743871935968, 0.5156845089211273, 0.7723861930965483, 0.9792925033945544 ], "category_id": 1, "smiles": "*.*C1=C(O[H])c2ccccc2OC1([1*])O", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 0.1922 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.1922 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5378 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9795 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3251 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7668 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5357 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3046 -1.2047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7668 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2085 -3.7244 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3251 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3251 -5.3780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7668 -6.1654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9795 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5378 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7463 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 11 14 1 0\n 12 13 1 0\n 14 15 2 0\nM ISO 1 7 1\nA 7\nR1\nA 10\nR\nA 16\nO2CdRf\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5487743871935968, 0.5156845089211273, 0.7723861930965483, 0.9792925033945544 ], "category_id": 1, "smiles": "*.*C1=C(O[H])c2ccccc2OC1([1*])O", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 0.1922 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.1922 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5378 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9795 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3251 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7668 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5357 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3046 -1.2047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7668 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2085 -3.7244 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3251 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3251 -5.3780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7668 -6.1654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9795 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5378 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7463 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 11 14 1 0\n 12 13 1 0\n 14 15 2 0\nM ISO 1 7 1\nA 7\nR1\nA 10\nR\nA 16\nO2CdRf\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7873936968484242, 0.5855432478143834, 0.9399699849924963, 0.8878410633888373 ], "category_id": 1, "smiles": "*c1oc2ccccc2c(=O)c1*", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 0.4005 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4005 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6036 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8066 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9094 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1125 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3155 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1125 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3155 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9094 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9094 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8066 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6036 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 2 0\n 10 12 1 0\n 12 13 2 0\nA 7\nR\nA 9\nR\nM END\n" } ] } ], "Anionic oxy-Cope rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03951975987993997, 0.11217758411916239, 0.18209104552276137, 0.4533844024816146 ], "category_id": 1, "smiles": "*C(O)(C=C)CC=C", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 0.5099 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7731 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1382 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1382 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8093 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7.1814 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7215 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7100 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6413 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 8 2 0\nA 5\nR\nA 6\nOK\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3151575787893947, 0.10438747411088722, 0.45722861430715356, 0.4471523144749945 ], "category_id": 1, "smiles": "*C(C=C)(CC=C)O[K]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6413 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1814 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1814 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7215 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7100 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6413 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 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2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 0.6337 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4357 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4912 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1110 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2932 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4357 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6337 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 7 1 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\nA 5\nOX\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.15957978989494748, 0.6434630866835287, 0.3106553276638319, 0.9363712229946749 ], "category_id": 1, "smiles": "*OC1=CCCC=C1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 0.6337 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4357 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4912 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1110 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2932 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4357 0.4488 0.0000 C 0 0 0 0 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13 14 2 0\nA 9\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.496248124062031, 0.05883824265073713, 0.7358679339669835, 0.477931690303356 ], "category_id": 1, "smiles": "*.C=C([O-])c1ccccc1OC(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 9.5175 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5175 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8502 -5.7717 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.3714 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3714 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0387 -8.8425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9859 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9859 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0387 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0387 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9859 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9859 0.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1197 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8502 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 2 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 2 0\nM CHG 1 3 -1\nA 12\nPh\nA 14\nOe\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.496248124062031, 0.05883824265073713, 0.7358679339669835, 0.477931690303356 ], "category_id": 1, "smiles": "*.C=C([O-])c1ccccc1OC(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 9.5175 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5175 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8502 -5.7717 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.3714 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3714 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0387 -8.8425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9859 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9859 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0387 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0387 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9859 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9859 0.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1197 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8502 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 2 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 2 0\nM CHG 1 3 -1\nA 12\nPh\nA 14\nOe\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8269134567283641, 0.03509649561622917, 0.9879939969984992, 0.4861896892718805 ], "category_id": 1, "smiles": "O=C1CC([O-])(c2ccccc2)Oc2ccccc21", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 5.1191 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4903 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5014 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4210 -0.8110 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1.8615 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8615 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4903 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4903 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8615 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2327 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2327 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1191 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7479 -6.0079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 12 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 7 12 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 12 13 2 0\nM CHG 1 4 -1\nA 3\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.29014507253626814, 0.6368981704474528, 0.5342671335667833, 0.9734116284148266 ], "category_id": 1, "smiles": "O=C(CC(=O)c1ccccc1O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 11.0821 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3221 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9600 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8379 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7158 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4758 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4758 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3537 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3537 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4758 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7158 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8379 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0821 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 2 0\n 3 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 2 0\n 5 11 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\nA 2\nPh\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.5757878939469735, 0.7081234115509768, 0.6583291645822912, 0.818574147754992 ], "category_id": 1, "smiles": "[14O]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 9.0551 -4.9055 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\nM ISO 1 1 14\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.5632816408204102, 0.8433481446605655, 0.6653326663331666, 0.9166378855062206 ], "category_id": 2, "text": [ "workup" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7013506753376688, 0.6761236655479442, 0.9459729864932466, 0.9661858793173675 ], "category_id": 1, "smiles": "O=C(CC(=O)c1ccccc1O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 12.8825 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4864 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4156 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9488 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3449 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8780 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8780 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4111 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4111 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8780 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3449 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9488 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8825 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 2 0\n 3 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 2 0\n 5 11 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\nA 2\nPh\nM END\n" } ] } ], "Bamford\u2013Stevens reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03451725862931466, 0.05849415936038194, 0.2926463231615808, 0.9378563550781238 ], "category_id": 1, "smiles": "CO.[1*]/C(=N\\[N-]S(=O)(=O)c1ccc(C)cc1)C([2*])([3*])[H]", "molfile": "\n RDKit 2D\n\n 10 8 0 0 0 0 0 0 0 0999 V2000\n 2.7058 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7058 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9019 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9019 -7.2677 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5097 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5097 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2233 -6.2441 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0272 -5.2205 0.0000 N 0 0 0 0 0 2 0 0 0 0 0 0\n 10.0115 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7058 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 1 0\nM CHG 1 8 -1\nM ISO 3 2 3 3 2 6 1\nA 2\nR3\nA 3\nR2\nA 6\nR1\nA 9\nTs\nA 10\nMeO\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3751875937968984, 0.17743228339315856, 0.6568284142071036, 0.8091692044852836 ], "category_id": 1, "smiles": "[1*]/C(=[NH+]\\NS(=O)(=O)c1ccc(C)cc1)C([2*])([3*])[H]", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 3.9599 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9599 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2289 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3655 -6.4803 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4178 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4178 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0123 -5.0630 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 11.4701 -3.4882 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3377 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 1 0\nM CHG 1 7 1\nM ISO 3 2 3 3 2 6 1\nA 2\nR3\nA 3\nR2\nA 6\nR1\nA 9\nTs\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3751875937968984, 0.17743228339315856, 0.6568284142071036, 0.8091692044852836 ], "category_id": 1, "smiles": "[1*]/C(=[NH+]\\NS(=O)(=O)c1ccc(C)cc1)C([2*])([3*])[H]", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 3.9599 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9599 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2289 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3655 -6.4803 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4178 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4178 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0123 -5.0630 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 11.4701 -3.4882 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3377 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 1 0\nM CHG 1 7 1\nM ISO 3 2 3 3 2 6 1\nA 2\nR3\nA 3\nR2\nA 6\nR1\nA 9\nTs\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7583791895947974, 0.1871813099532222, 0.984992496248124, 0.8091692044852836 ], "category_id": 1, "smiles": "*=N=C([1*])C([2*])([3*])[H]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5490 -0.5490 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -1.8481 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -3.1471 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 2 0\nM ISO 3 2 3 3 2 6 1\nA 2\nR3\nA 3\nR2\nA 6\nR1\nA 8\nNg\nM END\n" } ] } ], "Barbier coupling reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.24362181090545273, 0.20409143965922358, 0.3566783391695848, 0.45870056240241336 ], "category_id": 1, "smiles": "*[Mg]*.[Sg+].[Sg+].[Sg+].[Sg+]", "molfile": "\n RDKit 2D\n\n 6 1 0 0 0 0 0 0 0 0999 V2000\n 3.1068 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8606 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5667 -7.8189 0.0000 Sg 0 0 0 0 0 15 0 0 0 0 0 0\n 0.9179 -0.9685 0.0000 Sg 0 0 0 0 0 15 0 0 0 0 0 0\n 3.6011 -0.9685 0.0000 Sg 0 0 0 0 0 15 0 0 0 0 0 0\n 6.5667 -0.1811 0.0000 Sg 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\nM CHG 4 3 1 4 1 5 1 6 1\nA 1\nR\nA 2\nMgX\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4807403701850925, 0.23642275683296193, 0.6048024012006002, 0.3950482817166159 ], "category_id": 1, "smiles": "*[Mg]OC(*)(*)[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 4.9572 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3033 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6025 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3632 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9401 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nM ISO 1 5 2\nA 2\nOMgX\nA 3\nR\nA 4\nR\nA 5\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4807403701850925, 0.23642275683296193, 0.6048024012006002, 0.3950482817166159 ], "category_id": 1, "smiles": "*[Mg]OC(*)(*)[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 4.9572 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3033 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6025 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3632 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9401 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nM ISO 1 5 2\nA 2\nOMgX\nA 3\nR\nA 4\nR\nA 5\nR2\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.6458229114557279, 0.21621568359937546, 0.7128564282141071, 0.305126805827156 ], "category_id": 1, "smiles": "[14O]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 9.0428 -4.9843 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\nM ISO 1 1 14\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7388694347173587, 0.23743311049464128, 0.832416208104052, 0.38898615974653994 ], "category_id": 1, "smiles": "*C([1*])([2*])O", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 5.2070 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3754 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5544 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9403 -7.2677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3683 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nM ISO 2 3 1 5 2\nA 2\nR\nA 3\nR1\nA 5\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.13056528264132067, 0.7122993314839239, 0.24562281140570286, 0.9396289053617719 ], "category_id": 1, "smiles": "[1*]C([2*])=O.[2*]", "molfile": "\n RDKit 2D\n\n 5 3 0 0 0 0 0 0 0 0999 V2000\n 3.7911 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8717 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0486 -3.0945 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0486 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7755 -1.6772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 4 1 0\n 2 5 2 0\nM ISO 3 1 2 3 1 4 2\nA 1\nR2\nA 3\nR1\nA 4\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.35417708854427216, 0.7213925144390376, 0.4687343671835918, 0.9254839540982613 ], "category_id": 1, "smiles": "*.*[Mg]OC([1*])[2*]", "molfile": "\n RDKit 2D\n\n 6 4 0 0 0 0 0 0 0 0999 V2000\n 2.8432 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1550 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2647 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1550 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3744 -2.1496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3744 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\nM ISO 2 2 1 4 2\nA 1\nR\nA 2\nR1\nA 4\nR2\nA 6\nMgX\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.35417708854427216, 0.7213925144390376, 0.4687343671835918, 0.9254839540982613 ], "category_id": 1, "smiles": "*.*[Mg]OC([1*])[2*]", "molfile": "\n RDKit 2D\n\n 6 4 0 0 0 0 0 0 0 0999 V2000\n 2.8432 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1550 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2647 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1550 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3744 -2.1496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3744 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\nM ISO 2 2 1 4 2\nA 1\nR\nA 2\nR1\nA 4\nR2\nA 6\nMgX\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.576288144072036, 0.7476617096427002, 0.6998499249624812, 0.9062872345263541 ], "category_id": 1, "smiles": "*[Mg]OC(*)(*)[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 4.9298 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2574 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4649 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2325 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9017 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nM ISO 1 5 2\nA 2\nOMgX\nA 3\nR\nA 4\nR\nA 5\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.576288144072036, 0.7476617096427002, 0.6998499249624812, 0.9062872345263541 ], "category_id": 1, "smiles": "*[Mg]OC(*)(*)[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 4.9298 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2574 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4649 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2325 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9017 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nM ISO 1 5 2\nA 2\nOMgX\nA 3\nR\nA 4\nR\nA 5\nR2\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.7433716858429215, 0.7294753437324724, 0.8089044522261131, 0.8163657586368943 ], "category_id": 1, "smiles": "[13O]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 8.8789 -4.9843 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\nM ISO 1 1 13\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.8524262131065533, 0.7527134779510968, 0.9444722361180591, 0.9032561735413162 ], "category_id": 1, "smiles": "*C(*)([7*])O", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 5.0712 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3653 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3142 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4381 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7770 -7.2677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nM ISO 1 3 7\nA 2\nR\nA 3\nR7\nA 4\nR\nM END\n" } ] } ], "Bartoli indole synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04402201100550275, 0.06117044932432241, 0.24362181090545273, 0.2628063748748667 ], "category_id": 1, "smiles": "*c1ccccc1[N+](=O)[O-].C=C[Mg]Br", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 0.3525 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3525 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3500 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3500 -6.9528 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3474 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3449 -4.4331 0.0000 N 0 0 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3\nOMgBr\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7058529264632316, 0.06117044932432241, 0.904952476238119, 0.24166103436769348 ], "category_id": 1, "smiles": "*c1ccccc1N=O.C=C[Mg]Br", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 0.3919 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3919 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6125 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6125 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9638 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1845 -5.2205 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5358 -3.8819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9638 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6125 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5852 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1483 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.3283 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 9 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 5 8 1 0\n 6 7 2 0\n 8 9 2 0\n 10 11 1 0\n 10 12 2 0\nA 4\nR\nA 11\nBrMg\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2161080540270135, 0.4085581862278818, 0.352176088044022, 0.5860280083416567 ], "category_id": 1, "smiles": "*C1=CC=CC=C1N([O-]C=C)[Mg]Br", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 6.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 12 2 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\nM CHG 1 3 -1\nA 5\nMgBr\nA 8\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3616808404202101, 0.4274379545378579, 0.5377688844422212, 0.48332206873538697 ], "category_id": 2, "text": [ "[3,3]-sigmatropic" ] }, { "category": "[Txt]", "bbox": [ 0.3736868434217109, 0.5044674092425602, 0.5307653826913457, 0.5460028995245074 ], "category_id": 2, "text": [ "rearrangement" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5622811405702851, 0.3994958974390933, 0.7328664332166083, 0.5860280083416567 ], "category_id": 1, "smiles": "*C1=CC=CC(CC([H])=O)C1=N[Mg]Br", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3260 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3260 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6077 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6077 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8894 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0624 -5.1417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0624 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8894 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0624 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3441 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3441 -3.7244 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5172 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6077 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 2 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 5 8 1 0\n 6 7 1 0\n 8 9 1 0\n 8 13 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 2 0\nA 4\nR\nA 7\nMgBr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5622811405702851, 0.3994958974390933, 0.7328664332166083, 0.5860280083416567 ], "category_id": 1, "smiles": "*C1=CC=CC(CC([H])=O)C1=N[Mg]Br", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3260 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3260 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6077 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6077 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8894 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0624 -5.1417 0.0000 N 0 0 0 0 0 0 0 0 0 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0\n 1.8520 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8520 -8.3701 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2778 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2778 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8520 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1855 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2041 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9635 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5745 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5559 0.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4265 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 4 1 0\n 2 9 1 0\n 4 5 1 0\n 4 10 2 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 2 0\n 10 11 1 0\n 11 12 1 0\n 13 14 1 0\n 13 15 2 0\nA 6\nR\nA 12\nOMg\nA 14\nBrMg\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.128064032016008, 0.7189415772438882, 0.33166583291645824, 0.9809927613863557 ], "category_id": 1, "smiles": "*C1=CC=CC2([H])CC(O[Mg])N=C12.C=C[Mg]Br", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 5.1855 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4261 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4261 -1.9134 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4261 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8520 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8520 -8.3701 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2778 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2778 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8520 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1855 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2041 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9635 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5745 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5559 0.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4265 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 4 1 0\n 2 9 1 0\n 4 5 1 0\n 4 10 2 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 2 0\n 10 11 1 0\n 11 12 1 0\n 13 14 1 0\n 13 15 2 0\nA 6\nR\nA 12\nOMg\nA 14\nBrMg\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.3586793396698349, 0.7831327894978066, 0.423711855927964, 0.8510999554137204 ], "category_id": 1, "smiles": "*", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 2.8468 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nH3O\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.34667333666833416, 0.8722452959208936, 0.42621310655327665, 0.9160463584000381 ], "category_id": 2, "text": [ "workup" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4442221110555278, 0.7483940158074508, 0.6198099049524762, 0.9643785652735768 ], "category_id": 1, "smiles": "*C1=CC=CC2=C1NC([OH2])C2[H]", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 1.2135 -2.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6401 -3.1891 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2135 -2.7256 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -3.6073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -5.1073 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 11 1 0\n 3 4 1 0\n 3 9 2 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\nA 8\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4442221110555278, 0.7483940158074508, 0.6198099049524762, 0.9643785652735768 ], "category_id": 1, "smiles": "*C1=CC=CC2=C1NC([OH2])C2[H]", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 1.2135 -2.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6401 -3.1891 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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22 1 0\n 22 23 1 0\n 23 25 1 0\n 25 26 1 0\n 4 3 1 1\n 5 6 1 1\n 8 9 1 1\n 11 12 1 1\n 23 24 1 6\nA 2\nOAc\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.33016508254127064, 0.4279028765196931, 0.47573786893446723, 0.4713447929176315 ], "category_id": 2, "text": [ "1,5-hydrogen" ] }, { "category": "[Txt]", "bbox": [ 0.3356678339169585, 0.48437736783701296, 0.46623311655827915, 0.5202169488653121 ], "category_id": 2, "text": [ "abstraction" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.48874437218609307, 0.31766901365992445, 0.8149074537268635, 0.5652879371281733 ], "category_id": 1, "smiles": "CC(=O)OCC(=O)[C@H]1CC[C@@]2(C)C3CCC4=CC(=O)CC[C@]4(C)C3[C@@H](O)C[C@]12C.N=O", "molfile": "\n RDKit 2D\n\n 28 30 0 0 0 0 0 0 0 0999 V2000\n 11.1470 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5974 0.4488 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2729 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8226 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4714 -4.0394 0.0000 C 0 0 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0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3828 0.5621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2954 -0.6125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 2.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 4.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 2.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 3\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 11 1 0\n 6 13 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 12 1 0\n 10 11 1 0\n 12 13 1 0\n 14 15 1 0\n 15 16 1 0\n 15 17 2 0\nA 14\nPh\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6623311655827914, 0.42848733603749667, 0.7228614307153577, 0.47066655817868774 ], "category_id": 2, "text": [ "aldol" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7848924462231116, 0.3340862198167357, 0.9259629814907454, 0.5945261787520266 ], "category_id": 1, "smiles": "[H]C(CN1CCNCC1)(C(C)=O)C(O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 7.0047 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5240 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1003 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5240 -4.2756 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6196 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1390 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6196 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1003 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2461 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6128 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7586 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2779 -8.1339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6264 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4807 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5240 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 2 0\n 3 4 1 0\n 3 5 1 0\n 3 8 1 0\n 5 6 1 0\n 5 7 1 0\n 8 9 1 0\n 9 10 1 0\n 9 14 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\nA 6\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7848924462231116, 0.3340862198167357, 0.9259629814907454, 0.5945261787520266 ], "category_id": 1, "smiles": "[H]C(CN1CCNCC1)(C(C)=O)C(O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 7.0047 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5240 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1003 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5240 -4.2756 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6196 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1390 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6196 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1003 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2461 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6128 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7586 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2779 -8.1339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6264 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4807 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5240 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 2 0\n 3 4 1 0\n 3 5 1 0\n 3 8 1 0\n 5 6 1 0\n 5 7 1 0\n 8 9 1 0\n 9 10 1 0\n 9 14 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\nA 6\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4672336168084042, 0.3421203573674388, 0.6178089044522261, 0.6266627289548389 ], "category_id": 1, "smiles": "CC(O)=CCN12CCN(CC1)CC2.[H]C(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 17 17 0 0 0 0 0 0 0 0999 V2000\n 5.2500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 -5.1962 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3828 0.5621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2954 -0.6125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 2.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 4.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 2.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 3\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 11 1 0\n 6 13 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 12 1 0\n 10 11 1 0\n 12 13 1 0\n 14 15 1 0\n 15 16 1 0\n 15 17 2 0\nA 14\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4672336168084042, 0.3421203573674388, 0.6178089044522261, 0.6266627289548389 ], "category_id": 1, "smiles": "CC(O)=CCN12CCN(CC1)CC2.[H]C(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 17 17 0 0 0 0 0 0 0 0999 V2000\n 5.2500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 -5.1962 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3828 0.5621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2954 -0.6125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 2.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 4.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 2.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 3\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 11 1 0\n 6 13 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 12 1 0\n 10 11 1 0\n 12 13 1 0\n 14 15 1 0\n 15 16 1 0\n 15 17 2 0\nA 14\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.20110055027513757, 0.3588581439314035, 0.2706353176588294, 0.5161933376326718 ], "category_id": 1, "smiles": "C=CC(C)=O", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9806 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9146 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9806 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 3 5 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.09104552276138068, 0.48204825304218374, 0.19609804902451225, 0.6065773850780812 ], "category_id": 1, "smiles": "C1CN2CCN1CC2", "molfile": "\n RDKit 2D\n\n 8 9 0 0 0 0 0 0 0 0999 V2000\n 0.4452 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0957 -7.1102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0957 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1435 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1435 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0818 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3010 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3150 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 8 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 8 1 0\n 6 7 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3166583291645823, 0.4967775052184727, 0.40670335167583793, 0.5349396585843122 ], "category_id": 2, "text": [ "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4672336168084042, 0.3421203573674388, 0.6178089044522261, 0.6266627289548389 ], "category_id": 1, "smiles": "CC(O)=CCN12CCN(CC1)CC2.[H]C(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 17 17 0 0 0 0 0 0 0 0999 V2000\n 5.2500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 -5.1962 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3828 0.5621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2954 -0.6125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 2.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 4.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 2.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 3\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 11 1 0\n 6 13 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 12 1 0\n 10 11 1 0\n 12 13 1 0\n 14 15 1 0\n 15 16 1 0\n 15 17 2 0\nA 14\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2801400700350175, 0.7003089898362835, 0.42621310655327665, 0.9560623685336644 ], "category_id": 1, "smiles": "C/C([O-])=C(\\CN1CCNCC1)C(O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 7.4600 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8356 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8356 -0.6535 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 4.3316 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7674 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2032 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7674 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3316 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4292 -6.4803 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8730 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9706 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4666 -8.1339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4666 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4292 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\n 4 5 1 0\n 4 8 1 0\n 5 6 1 0\n 5 7 1 0\n 8 9 1 0\n 9 10 1 0\n 9 14 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\nM CHG 1 3 -1\nA 6\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5502751375687844, 0.7639125787793496, 0.6953476738369184, 0.9004929171413016 ], "category_id": 1, "smiles": "C=C(C(C)=O)C(O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 13.6810 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7891 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0084 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2277 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2245 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2277 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0084 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7891 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 2 0\n 3 4 1 0\n 3 7 2 0\n 4 5 1 0\n 4 6 1 0\nA 5\nPh\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7668834417208604, 0.7706076934049354, 0.8569284642321161, 0.8984843827536259 ], "category_id": 1, "smiles": "C1CN2CCN1CC2", "molfile": "\n RDKit 2D\n\n 8 9 0 0 0 0 0 0 0 0999 V2000\n 7.0514 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0398 -7.1102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0398 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0230 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0230 -3.7244 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8876 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2770 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4407 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 1 0\n 2 3 1 0\n 2 8 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5502751375687844, 0.7639125787793496, 0.6953476738369184, 0.9004929171413016 ], "category_id": 1, "smiles": "C=C(C(C)=O)C(O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 13.6810 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7891 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0084 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2277 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2245 -5.2205 0.0000 R 0 0 0 0 0 0 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0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5021 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nM ISO 2 1 12 3 12\nA 1\nR12\nA 3\nR12\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7898949474737369, 0.08884603355850691, 0.927463731865933, 0.413963936580296 ], "category_id": 1, "smiles": "O.[2*]C#[N-][16*]", "molfile": "\n RDKit 2D\n\n 5 3 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 1.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\nM CHG 1 1 -1\nM ISO 1 4 2\nA 2\nR16\nA 4\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7898949474737369, 0.08884603355850691, 0.927463731865933, 0.413963936580296 ], "category_id": 1, "smiles": "O.[2*]C#[N-][6*]", "molfile": "\n RDKit 2D\n\n 5 3 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 N 0 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0.6361090101364675, 0.8284142071035517, 0.9456289578236217 ], "category_id": 1, "smiles": "*C(=O)C(*)O", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 4.7903 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4739 -3.1732 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3697 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3175 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3697 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7903 -7.8189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 1 0\nA 2\nAr\nA 4\nAr\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.8824412206103052, 0.6964198822960967, 0.9409704852426213, 0.8466280922030981 ], "category_id": 1, "smiles": "[Co]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 3.5816 -6.2441 0.0000 Co 0 0 0 0 0 15 0 0 0 0 0 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6693346673336669, 0.6361090101364675, 0.8284142071035517, 0.9456289578236217 ], "category_id": 1, "smiles": "*C(=O)C(*)O", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 4.7903 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4739 -3.1732 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3697 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3175 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3697 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7903 -7.8189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 1 0\nA 2\nAr\nA 4\nAr\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.8824412206103052, 0.6964198822960967, 0.9409704852426213, 0.8466280922030981 ], "category_id": 1, "smiles": "[Co]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 3.5816 -6.2441 0.0000 Co 0 0 0 0 0 15 0 0 0 0 0 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.40520260130065033, 0.6076604855328688, 0.5847923961980991, 0.9638360135699249 ], "category_id": 1, "smiles": "*C([H])(O)C(*)(O)C#N", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 4.7897 -3.8819 0.0000 C 0 0 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0.6588294147073537, 0.038104766669048815, 0.8299149574787393, 0.18072546477320295 ], "category_id": 1, "smiles": "*C(O)C([H])(C(=O)OCC)C(C)=O[H]", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 2.5981 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8481 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -0.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3481 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3481 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8481 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3481 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4019 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 13 2 3\n 3 4 1 0\n 3 5 1 0\n 3 10 1 0\n 5 6 1 0\n 5 9 2 0\n 6 7 1 0\n 7 8 1 0\n 10 11 1 0\n 10 12 1 0\n 13 14 1 0\nA 11\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6588294147073537, 0.038104766669048815, 0.8299149574787393, 0.18072546477320295 ], "category_id": 1, "smiles": "*C(O)C([H])(C(=O)OCC)C(C)=O[H]", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 2.5981 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8481 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -0.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3481 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3481 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8481 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3481 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4019 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 13 2 3\n 3 4 1 0\n 3 5 1 0\n 3 10 1 0\n 5 6 1 0\n 5 9 2 0\n 6 7 1 0\n 7 8 1 0\n 10 11 1 0\n 10 12 1 0\n 13 14 1 0\nA 11\nAr\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.09204602301150576, 0.29286234954211804, 0.26413206603301653, 0.43602740145582997 ], "category_id": 1, "smiles": "*COC(=O)/C(=C(/C)O[H])C(*)O", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 0.7212 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6787 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6787 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7212 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6363 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5938 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5513 -4.5906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5089 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4664 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5938 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6363 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6787 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5938 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 5 2 0\n 3 4 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 1 0\n 6 10 2 0\n 7 8 1 0\n 8 9 1 0\n 11 12 1 0\n 11 13 1 0\nA 9\n,\nA 12\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.09204602301150576, 0.29286234954211804, 0.26413206603301653, 0.43602740145582997 ], "category_id": 1, "smiles": "*COC(=O)/C(=C(/C)O[H])C(*)O", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 0.7212 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6787 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6787 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7212 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6363 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5938 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5513 -4.5906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5089 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4664 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5938 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6363 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6787 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5938 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 5 2 0\n 3 4 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 1 0\n 6 10 2 0\n 7 8 1 0\n 8 9 1 0\n 11 12 1 0\n 11 13 1 0\nA 9\n,\nA 12\nAr\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.2786393196598299, 0.333688885258956, 0.3341670835417709, 0.3756041285949097 ], "category_id": 1, "smiles": "*.[Ir]", "molfile": "\n RDKit 2D\n\n 2 0 0 0 0 0 0 0 0 0999 V2000\n 2.2421 -5.4567 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1747 -5.4567 0.0000 Ir 0 0 0 0 0 15 0 0 0 0 0 0\nA 1\n4+\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.35117558779389696, 0.2955841185899072, 0.5212606303151576, 0.4523580157425652 ], "category_id": 1, "smiles": "*C(O)/C(C(=O)OC[I-])=C(\\C)O[H]", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 1.0236 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7917 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7917 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0236 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4667 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1417 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9098 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5848 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3529 -4.0394 0.0000 I 0 0 0 0 0 1 0 0 0 0 0 0\n 6.1417 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4667 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2334 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1417 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 5 2 0\n 3 4 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 1 0\n 6 10 2 0\n 7 8 1 0\n 8 9 1 0\n 11 12 1 0\n 11 13 1 0\nM CHG 1 9 -1\nM RAD 1 9 2\nA 12\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.35117558779389696, 0.2955841185899072, 0.5212606303151576, 0.4523580157425652 ], "category_id": 1, "smiles": "*C(O)/C(C(=O)OC[I-])=C(\\C)O[H]", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 1.0236 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7917 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7917 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0236 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4667 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1417 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9098 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5848 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3529 -4.0394 0.0000 I 0 0 0 0 0 1 0 0 0 0 0 0\n 6.1417 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4667 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2334 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1417 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 5 2 0\n 3 4 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 1 0\n 6 10 2 0\n 7 8 1 0\n 8 9 1 0\n 11 12 1 0\n 11 13 1 0\nM CHG 1 9 -1\nM RAD 1 9 2\nA 12\nAr\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5417708854427213, 0.2754430276362671, 0.7128564282141071, 0.49100713622117187 ], "category_id": 1, "smiles": "*/C=C(C(=O)OCC)\\C(C)=[O+]/[H].NC([NH2+])=O", "molfile": "\n RDKit 2D\n\n 16 14 0 0 0 0 0 0 0 0999 V2000\n 8.1660 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8731 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5801 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2872 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9942 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7013 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4083 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7013 -0.4173 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 2.9942 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9942 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3610 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2872 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6482 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3552 -6.1654 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.9411 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6482 -8.4488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 1 0\n 5 10 2 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 10 11 1 0\n 13 14 1 0\n 13 15 1 0\n 13 16 2 0\nM CHG 2 8 1 14 1\nM RAD 1 14 2\nA 11\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5417708854427213, 0.2754430276362671, 0.7128564282141071, 0.49100713622117187 ], "category_id": 1, "smiles": "*/C=C(C(=O)OCC)\\C(C)=[O+]/[H].NC([NH2+])=O", "molfile": "\n RDKit 2D\n\n 16 14 0 0 0 0 0 0 0 0999 V2000\n 8.1660 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8731 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5801 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2872 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9942 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7013 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4083 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7013 -0.4173 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 2.9942 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9942 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3610 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2872 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6482 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3552 -6.1654 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.9411 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6482 -8.4488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 1 0\n 5 10 2 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 10 11 1 0\n 13 14 1 0\n 13 15 1 0\n 13 16 2 0\nM CHG 2 8 1 14 1\nM RAD 1 14 2\nA 11\nAr\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7243621810905453, 0.3374993619258609, 0.8254127063531765, 0.37233800573756265 ], "category_id": 2, "text": [ "conjugate" ] }, { "category": "[Txt]", "bbox": [ 0.7338669334667334, 0.3864912047860665, 0.8159079539769885, 0.41643066431174774 ], "category_id": 2, "text": [ "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.1265632816408204, 0.5438094557482823, 0.2991495747873937, 0.7229018590928118 ], "category_id": 1, "smiles": "*C(NC(N)=O)/C(C(=O)OCC)=C(\\C)O", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 10.2306 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5805 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0129 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4453 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8777 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8777 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6103 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2276 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2276 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8777 -8.0551 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6600 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2276 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2276 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6600 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4453 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 15 2 0\n 5 6 1 0\n 5 12 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 1 0\n 12 14 1 0\nA 7\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1265632816408204, 0.5438094557482823, 0.2991495747873937, 0.7229018590928118 ], "category_id": 1, "smiles": "*C(NC(N)=O)/C(C(=O)OCC)=C(\\C)O", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 10.2306 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5805 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0129 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4453 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8777 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8777 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6103 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2276 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2276 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8777 -8.0551 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6600 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2276 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2276 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6600 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4453 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 15 2 0\n 5 6 1 0\n 5 12 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 1 0\n 12 14 1 0\nA 7\nAr\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.42021010505252626, 0.5465312247960715, 0.632816408204102, 0.7196357362354647 ], "category_id": 1, "smiles": "*C(NC(N)=O)C(C(=O)OCC)C(C)=O[H]", "molfile": "\n RDKit 2D\n\n 16 15 0 0 0 0 0 0 0 0999 V2000\n 3.8971 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2990 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4952 0.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 2 3\n 3 4 1 0\n 3 9 1 0\n 4 5 1 0\n 4 8 2 0\n 5 6 1 0\n 6 7 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 2 0\n 15 16 1 0\nA 10\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.42021010505252626, 0.5465312247960715, 0.632816408204102, 0.7196357362354647 ], "category_id": 1, "smiles": "*C(NC(N)=O)C(C(=O)OCC)C(C)=O[H]", "molfile": "\n RDKit 2D\n\n 16 15 0 0 0 0 0 0 0 0999 V2000\n 3.8971 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 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-1\nA 9\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6253126563281641, 0.6062121970075947, 0.7668834417208604, 0.9145897059201539 ], "category_id": 1, "smiles": "*C1=NCCc2ccccc21", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 7.4367 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1485 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7649 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3814 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3814 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7649 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1485 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4367 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4367 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8202 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8202 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\nA 9\nR\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.7863931965982992, 0.712958257785019, 0.8329164582291145, 0.8038900873361582 ], "category_id": 2, "text": [ "HCI" ] }, { "category": "[Mol]", "bbox": [ 0.8694347173586794, 0.6417942172667361, 0.9489744872436218, 0.8697827174456794 ], "category_id": 1, "smiles": "O=P(=[O-])Cl", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 2 4 2 0\nM CHG 1 1 -1\nM END\n" } ] } ], "Blaise reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.10905452726363181, 0.21167573918538218, 0.2336168084042021, 0.36302937653037043 ], "category_id": 1, "smiles": "[1*]C(Br)C(=O)O[2*]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 6.1424 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1424 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5708 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9999 -1.1260 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\nM ISO 1 2 1\nA 2\nR1\nA 3\nCO2R2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.24212106053026514, 0.23141751796951107, 0.29814907453726863, 0.2939331507859193 ], "category_id": 2, "text": [ "Zn(0)" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.32416208104052024, 0.20619191174534637, 0.447223611805903, 0.41786765093072853 ], "category_id": 1, "smiles": "*C([1*])C(=O)O[2*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 6.6441 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9260 -3.7244 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6441 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1608 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1608 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7781 -5.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\nM ISO 1 3 1\nA 2\nBrZn\nA 3\nR1\nA 5\nOR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.32416208104052024, 0.20619191174534637, 0.447223611805903, 0.41786765093072853 ], "category_id": 1, "smiles": "*C([1*])C(=O)O[2*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 6.6441 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9260 -3.7244 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6441 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1608 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1608 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7781 -5.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\nM ISO 1 3 1\nA 2\nBrZn\nA 3\nR1\nA 5\nOR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.46023011505752875, 0.20948220820936783, 0.5722861430715358, 0.2741913720017904 ], "category_id": 2, "text": [ "nucleophilic" ] }, { "category": "[Txt]", "bbox": [ 0.47873936968484243, 0.29722344724994076, 0.5542771385692846, 0.353158487138306 ], "category_id": 2, "text": [ "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.551775887943972, 0.09541859745662305, 0.7453726863431716, 0.4156741199547142 ], "category_id": 1, "smiles": "*/N=C(/*)C([1*])C(=O)O[2*].[H][O-]", "molfile": "\n RDKit 2D\n\n 9 7 0 0 0 0 0 0 0 0999 V2000\n 6.3908 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8193 -6.3228 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0671 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6386 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0671 -8.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3908 -3.4882 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0671 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5144 -0.9685 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 4.4002 -0.9685 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 1 0\n 6 7 1 0\n 8 9 1 0\nM CHG 1 8 -1\nM ISO 1 5 1\nA 2\nR\nA 4\nCO2R2\nA 5\nR1\nA 7\nZnBr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.551775887943972, 0.09541859745662305, 0.7453726863431716, 0.4156741199547142 ], "category_id": 1, "smiles": 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0.5052526263131566, 0.06668334167083542, 0.5457728864432216, 0.10325162581290645 ], "category_id": 2, "text": [ "SN2" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5887943971985993, 0.03298315824578956, 0.6918459229614807, 0.16419876604969152 ], "category_id": 1, "smiles": "[1*][C@@H](O)[C@@H]([2*])N", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 4.0778 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1524 -3.0945 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0778 -7.8189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7372 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3967 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7372 -0.1024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 4 1 0\n 4 5 1 0\n 1 3 1 6\n 4 6 1 6\nM ISO 2 2 1 5 2\nA 2\nR1\nA 5\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.12306153076538269, 0.3427380356845089, 0.36568284142071034, 0.4804068701017175 ], "category_id": 1, "smiles": "*.[1*][C@@H](O)[C@@H]([2*])N[N+]#N", "molfile": "\n RDKit 2D\n\n 9 7 0 0 0 0 0 0 0 0999 V2000\n 5.3553 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7437 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3801 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7437 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3553 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9173 -5.3780 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6941 -5.3780 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 15.6693 -5.3780 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 21.0246 -6.0079 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 4 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 3 0\n 1 3 1 6\n 4 6 1 6\nM CHG 1 7 1\nM ISO 2 2 1 5 2\nA 2\nR1\nA 5\nR2\nA 9\nPPh3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.42021010505252626, 0.3319826579956645, 0.6398199099549775, 0.47036851759212933 ], "category_id": 1, "smiles": "*[N-]=NNC([2*])C([4*])O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -2.2500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -3.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -4.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 6\n 1 4 1 0\n 4 5 1 0\n 4 6 1 6\n 6 7 1 0\n 7 8 2 3\n 8 9 1 0\nM CHG 1 8 -1\nM ISO 2 2 4 5 2\nA 2\nR4\nA 5\nR2\nA 9\nPh3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.42021010505252626, 0.3319826579956645, 0.6398199099549775, 0.47036851759212933 ], "category_id": 1, "smiles": "*[N-]=NNC([2*])C([4*])O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -2.2500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -3.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -4.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 6\n 1 4 1 0\n 4 5 1 0\n 4 6 1 6\n 6 7 1 0\n 7 8 2 3\n 8 9 1 0\nM CHG 1 8 -1\nM ISO 2 2 4 5 2\nA 2\nR4\nA 5\nR2\nA 9\nPh3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6863431715857929, 0.32481240620310153, 0.8924462231115557, 0.4631982657995664 ], "category_id": 1, "smiles": "[1*][C@@H](O)[C@@H]([2*])N=NN=P[3*]", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 5.5751 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9266 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7031 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9266 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5751 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7987 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6707 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5427 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4147 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 4 1 0\n 4 5 1 0\n 6 7 2 3\n 7 8 1 0\n 8 9 2 0\n 1 3 1 6\n 4 6 1 6\nM ISO 2 2 1 5 2\nA 2\nR1\nA 5\nR2\nA 9\nPR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6863431715857929, 0.32481240620310153, 0.8924462231115557, 0.4631982657995664 ], "category_id": 1, "smiles": "[1*][C@@H](O)[C@@H]([2*])N=NN=P[3*]", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 5.5751 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9266 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7031 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9266 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5751 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7987 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6707 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5427 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4147 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 4 1 0\n 4 5 1 0\n 6 7 2 3\n 7 8 1 0\n 8 9 2 0\n 1 3 1 6\n 4 6 1 6\nM ISO 2 2 1 5 2\nA 2\nR1\nA 5\nR2\nA 9\nPR3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.42021010505252626, 0.3319826579956645, 0.6398199099549775, 0.47036851759212933 ], "category_id": 1, "smiles": "*[N-]=NNC([2*])C([4*])O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -2.2500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -3.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -4.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 6\n 1 4 1 0\n 4 5 1 0\n 4 6 1 6\n 6 7 1 0\n 7 8 2 3\n 8 9 1 0\nM CHG 1 8 -1\nM ISO 2 2 4 5 2\nA 2\nR4\nA 5\nR2\nA 9\nPh3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2651325662831416, 0.5858095714523929, 0.3371685842921461, 0.6990995497748874 ], "category_id": 1, "smiles": "*n1nnP1[3*]", "molfile": "\n RDKit 2D\n\n 5 5 0 0 0 0 0 0 0 0999 V2000\n 1.1435 -1.2047 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7886 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7886 -6.0079 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9334 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1435 -4.6693 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 2 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\nA 2\nPR3\nA 4\nX\nM END\n" } ], "conditions": [], "products": [ { "category": "[Txt]", "bbox": [ 0.4447223611805903, 0.6223778555944639, 0.47573786893446723, 0.6632482908120727 ], "category_id": 2, "text": [ "Nz" ] }, { "category": "[Mol]", "bbox": [ 0.5352676338169085, 0.5470902117725529, 0.6388194097048524, 0.7191762547940638 ], "category_id": 1, "smiles": "[1*][C@@H](O)[C@@H]([2*])NP[3*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 5.1380 -2.2283 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1380 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1380 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1661 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1098 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8789 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1098 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 3 1 1 6\n 5 7 1 6\nM ISO 2 4 2 6 1\nA 2\nPR3\nA 4\nR2\nA 6\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5352676338169085, 0.5470902117725529, 0.6388194097048524, 0.7191762547940638 ], "category_id": 1, "smiles": "[1*][C@@H](O)[C@@H]([2*])NP[3*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 5.1380 -2.2283 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1380 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1380 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1661 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1098 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8789 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1098 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 3 1 1 6\n 5 7 1 6\nM ISO 2 4 2 6 1\nA 2\nPR3\nA 4\nR2\nA 6\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7213606803401701, 0.5492412873103218, 0.8374187093546773, 0.7213273303318326 ], "category_id": 1, "smiles": "[1*]C(O)[C@@H]([2*])N=P[3*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 4.1225 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1225 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9849 -4.5906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1837 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2449 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1837 -2.2283 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1837 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 6 1 0\n 6 7 2 0\n 4 5 1 6\nM ISO 2 2 1 5 2\nA 2\nR1\nA 5\nR2\nA 7\nPR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7213606803401701, 0.5492412873103218, 0.8374187093546773, 0.7213273303318326 ], "category_id": 1, "smiles": 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0.45822911455727866, 0.9651158912789728 ], "category_id": 1, "smiles": "[1*][C@H]1O[3*]N[C@@H]1[2*]", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 4.0157 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0472 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9921 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5118 -1.5197 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1417 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5827 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 3 1 0\n 1 6 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 1 2 1 1\n 6 7 1 6\nM ISO 3 2 1 4 3 7 2\nA 2\nR1\nA 4\nR3\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.34667333666833416, 0.8059363014840754, 0.45822911455727866, 0.9651158912789728 ], "category_id": 1, "smiles": "[1*][C@H]1O[3*]N[C@@H]1[2*]", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 4.0157 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 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0.3765181253330975, 0.4177088544272136, 0.4419133786804249 ], "category_id": 2, "text": [ "transfer" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.45722861430715356, 0.11691878628764607, 0.7458729364682342, 0.5548688162803542 ], "category_id": 1, "smiles": "*.CC.[H]Cc1cccc[n+]1OC(=O)C(F)(F)F", "molfile": "\n RDKit 2D\n\n 15 13 0 0 0 0 0 0 0 0999 V2000\n 4.5207 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9591 -2.9370 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0823 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0823 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6439 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2055 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2055 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6439 -3.7244 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 1.6439 -5.5354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0823 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0823 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5207 -5.5354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5825 -4.5906 0.0000 C 0 0 0 0 0 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8.7597 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7597 -1.4409 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8986 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9358 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9358 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 6 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 7 8 1 0\n 7 18 1 0\n 8 9 1 0\n 9 10 1 0\n 9 17 1 0\n 10 11 2 0\n 10 15 1 0\n 11 12 1 0\n 12 13 1 0\n 12 16 1 0\n 13 14 1 0\n 14 15 1 0\n 15 16 1 0\n 17 18 1 0\n 19 20 2 0\n 19 24 1 0\n 20 21 1 0\n 21 22 2 0\n 22 23 1 0\n 23 24 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6928464232116058, 0.14348273207811335, 0.8884442221110556, 0.20954672382630943 ], "category_id": 2, "text": [ "hetero-Diels-Alder" ] }, { "category": "[Txt]", "bbox": [ 0.7448724362181091, 0.24361096957147305, 0.8379189594797398, 0.3045137119643413 ], "category_id": 2, "text": [ "reaction" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.08604302151075538, 0.607995174057617, 0.2366183091545773, 0.9672181291884332 ], "category_id": 1, "smiles": "[N-]C1=CC([N-])C1C(C1N=CC([N-])=N1)N1CCCC1", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n 4.7738 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4781 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4328 -5.7717 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9555 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7968 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7968 -1.6772 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7516 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7516 0.0551 0.0000 N 0 0 0 0 0 1 0 0 0 0 0 0\n 8.3883 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4335 -4.5118 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9102 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7516 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7516 0.0551 0.0000 N 0 0 0 0 0 1 0 0 0 0 0 0\n 8.3883 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7516 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7968 -1.6772 0.0000 N 0 0 0 0 0 1 0 0 0 0 0 0\n 6.2742 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4788 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 18 1 0\n 2 3 1 0\n 3 4 1 0\n 3 17 1 0\n 4 5 1 0\n 4 11 1 0\n 5 6 1 0\n 5 10 1 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\n 11 12 1 0\n 11 15 1 0\n 12 13 1 0\n 12 14 2 0\n 14 15 1 0\n 15 16 1 0\n 17 18 1 0\nM CHG 3 8 -1 13 -1 16 -1\nM RAD 3 8 2 13 2 16 2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.08604302151075538, 0.607995174057617, 0.2366183091545773, 0.9672181291884332 ], "category_id": 1, "smiles": "[N-]C1=CC([N-])C1C(C1N=CC([N-])=N1)N1CCCC1", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n 4.7738 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4781 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4328 -5.7717 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9555 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7968 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7968 -1.6772 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7516 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7516 0.0551 0.0000 N 0 0 0 0 0 1 0 0 0 0 0 0\n 8.3883 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4335 -4.5118 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9102 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7516 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7516 0.0551 0.0000 N 0 0 0 0 0 1 0 0 0 0 0 0\n 8.3883 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7516 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7968 -1.6772 0.0000 N 0 0 0 0 0 1 0 0 0 0 0 0\n 6.2742 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4788 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 18 1 0\n 2 3 1 0\n 3 4 1 0\n 3 17 1 0\n 4 5 1 0\n 4 11 1 0\n 5 6 1 0\n 5 10 1 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\n 11 12 1 0\n 11 15 1 0\n 12 13 1 0\n 12 14 2 0\n 14 15 1 0\n 15 16 1 0\n 17 18 1 0\nM CHG 3 8 -1 13 -1 16 -1\nM RAD 3 8 2 13 2 16 2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.25512756378189094, 0.7163814105195012, 0.4332166083041521, 0.7793486526545006 ], "category_id": 2, "text": [ "retro-Diels-Alder" ] }, { "category": 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0 0 0 0 0 0 0 0\n 12.5140 1.0000 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\n 4 5 1 0\n 4 6 1 0\n 7 8 1 0\nM CHG 1 4 1\nM ISO 4 1 1 3 2 5 3 6 4\nA 1\nR1\nA 3\nR2\nA 5\nR3\nA 6\nR4\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5507753876938469, 0.21918201440553145, 0.7583791895947974, 0.8377210889567346 ], "category_id": 1, "smiles": "CI.[1*]/C([2*])=[N+](\\[3*])[4*]", "molfile": "\n RDKit 2D\n\n 8 6 0 0 0 0 0 0 0 0999 V2000\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1531 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3063 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1531 -5.6929 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 0.0000 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3063 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1491 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5140 1.0000 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\n 4 5 1 0\n 4 6 1 0\n 7 8 1 0\nM CHG 1 4 1\nM ISO 4 1 1 3 2 5 3 6 4\nA 1\nR1\nA 3\nR2\nA 5\nR3\nA 6\nR4\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8209104552276139, 0.26561888186433047, 0.9514757378689345, 0.8061440190847512 ], "category_id": 1, "smiles": "[1*]C([2*])([H])N([3*])[4*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 4.5932 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7666 -1.5197 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2078 -1.5197 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5932 -0.1024 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5932 -6.0079 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7666 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2078 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 4 2 1 3 2 6 3 7 4\nA 2\nR1\nA 3\nR2\nA 6\nR3\nA 7\nR4\nM END\n" } ] } ], "Borsche\u2013Drechsel cyclization.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04852426213106553, 0.05824391696739635, 0.21160580290145073, 0.4588194275390815 ], "category_id": 1, "smiles": "[H].[H]C1CCCC/C1=N/Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 7.3028 0.8425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5532 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5532 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7275 -1.2835 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3028 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3028 -5.1417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5532 -6.0866 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7275 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9778 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2282 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2282 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9778 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7275 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2807 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2807 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1285 -8.3701 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 15 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 5 14 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3091545772886443, 0.08201694430102752, 0.4607303651825913, 0.438612354305495 ], "category_id": 1, "smiles": "C1=C([NH+]Nc2ccccc2)CCCC1", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 7.9490 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0412 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0412 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9490 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9490 -6.4803 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.0412 -7.7402 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0540 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0540 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1462 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2385 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2385 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1462 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9363 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9363 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 13 14 1 0\nM CHG 1 5 1\nM RAD 1 5 2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3091545772886443, 0.08201694430102752, 0.4607303651825913, 0.438612354305495 ], "category_id": 1, "smiles": "C1=C([NH+]Nc2ccccc2)CCCC1", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 7.9490 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0412 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0412 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9490 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9490 -6.4803 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.0412 -7.7402 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0540 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0540 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1462 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2385 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2385 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1462 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9363 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9363 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 13 14 1 0\nM CHG 1 5 1\nM RAD 1 5 2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.04852426213106553, 0.05824391696739635, 0.21160580290145073, 0.4588194275390815 ], "category_id": 1, "smiles": "[H].[H]C1CCCC/C1=N/Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 7.3028 0.8425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5532 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5532 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7275 -1.2835 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3028 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3028 -5.1417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5532 -6.0866 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7275 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9778 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2282 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2282 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9778 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7275 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2807 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2807 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2807 -8.3701 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 15 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 5 14 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3091545772886443, 0.08201694430102752, 0.4607303651825913, 0.438612354305495 ], "category_id": 1, "smiles": "C1=C([NH+]Nc2ccccc2)CCCC1", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 7.9490 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0412 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0412 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9490 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9490 -6.4803 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.0412 -7.7402 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0540 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0540 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1462 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2385 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2385 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1462 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9363 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9363 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 13 14 1 0\nM CHG 1 5 1\nM RAD 1 5 2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4852426213106553, 0.16759984270209974, 0.663831915957979, 0.2508054383698088 ], "category_id": 2, "text": [ "[3,3]-sigmatropic" ] }, { "category": "[Txt]", "bbox": [ 0.49524762381190596, 0.29003093347030023, 0.6533266633316658, 0.35540675863778587 ], "category_id": 2, "text": [ "rearrangement" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6873436718359179, 0.0879602011344353, 0.8384192096048024, 0.3993868592050036 ], "category_id": 1, "smiles": "N=C1C=CC=CC1C1CCCCC1=N", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 8.9815 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8042 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8042 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6268 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6268 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8042 -8.2126 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4495 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3629 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3629 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4495 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9815 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9815 -6.9528 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1588 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1588 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 3 4 1 0\n 3 11 1 0\n 4 5 1 0\n 4 10 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 2 0\n 11 13 1 0\n 13 14 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6873436718359179, 0.0879602011344353, 0.8384192096048024, 0.3993868592050036 ], "category_id": 1, "smiles": "N=C1C=CC=CC1C1CCCCC1=N", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 8.9815 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8042 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8042 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6268 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6268 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8042 -8.2126 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4495 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3629 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3629 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4495 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9815 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9815 -6.9528 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1588 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1588 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 3 4 1 0\n 3 11 1 0\n 4 5 1 0\n 4 10 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 2 0\n 11 13 1 0\n 13 14 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8774387193596799, 0.1509587235685579, 0.9224612306153076, 0.2567486952032166 ], "category_id": 2, "text": [ "H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.1485742871435718, 0.5955143347074606, 0.31165582791395696, 0.906940992778029 ], "category_id": 1, "smiles": "[H]C1(C2CCCCC2=[NH2])C=CC=CC1=N.[OH]", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 2.6491 -1.6339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 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0\n 8 9 2 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3891945972986493, 0.6264192702411812, 0.6003001500750376, 0.9675622124787884 ], "category_id": 1, "smiles": "[H].[H]C12CCCCC1([NH2+])Nc1ccccc12", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 9.5084 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3052 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3776 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8701 -0.0236 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2904 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2032 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3479 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3479 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2032 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2904 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3776 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7690 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3924 -5.0630 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 9.9722 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8998 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0306 -8.2126 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 15 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 12 1 0\n 5 6 1 0\n 5 10 2 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\nM CHG 1 13 1\nM RAD 1 13 2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3891945972986493, 0.6264192702411812, 0.6003001500750376, 0.9675622124787884 ], "category_id": 1, "smiles": "[H].[H]C12CCCCC1([NH2+])Nc1ccccc12", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 9.5084 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3052 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3776 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8701 -0.0236 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2904 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2032 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3479 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3479 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2032 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2904 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3776 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7690 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3924 -5.0630 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 9.9722 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8998 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0306 -8.2126 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 15 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 12 1 0\n 5 6 1 0\n 5 10 2 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\nM CHG 1 13 1\nM RAD 1 13 2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6833416708354177, 0.6371171325413153, 0.8424212106053026, 0.9259594146449338 ], "category_id": 1, "smiles": "c1ccc2c3c([nH]c2c1)CCCC3", "molfile": "\n RDKit 2D\n\n 13 15 0 0 0 0 0 0 0 0999 V2000\n 11.0899 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5228 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"molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6161 -1.0216 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8297 -1.9033 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 8 2 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 8 1 0\n 5 6 1 0\n 6 7 1 0\nM ISO 1 2 2\nA 5\nX\nA 6\nY\nA 7\nZ\nA 8\nA\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6298149074537268, 0.0815806839590008, 0.9804902451225613, 0.8672381403467692 ], "category_id": 1, "smiles": "[H][2H]B*C1=N**=*1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 3.5260 -1.2990 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0260 -1.2990 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n 5.7760 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 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"[Mol]", "bbox": [ 0.3581790895447724, 0.09040403286220225, 0.46773386693346675, 0.2745296777742105 ], "category_id": 1, "smiles": "*[W].[H]C(=O)N(C)C", "molfile": "\n RDKit 2D\n\n 6 4 0 0 0 0 0 0 0 0999 V2000\n 2.5680 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2917 -8.0551 0.0000 W 0 0 0 0 0 1 0 0 0 0 0 0\n 6.6925 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2022 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0270 -4.3543 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6925 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 2 0\nA 1\nR\nA 4\nMe2N\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3581790895447724, 0.09040403286220225, 0.46773386693346675, 0.2745296777742105 ], "category_id": 1, "smiles": "*[W].[H]C(=O)N(C)C", "molfile": "\n RDKit 2D\n\n 6 4 0 0 0 0 0 0 0 0999 V2000\n 2.5680 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2917 -8.0551 0.0000 W 0 0 0 0 0 1 0 0 0 0 0 0\n 6.6925 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2022 -4.3543 0.0000 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C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5877 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8519 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1161 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2725 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2725 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5368 -3.4094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1161 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8519 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5877 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8223 0.0551 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 10 11 2 0\nM CHG 1 12 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.24762381190595298, 0.03187071476914928, 0.44022011005502754, 0.29500841106827924 ], "category_id": 1, "smiles": "[H].[H]C1([H])C(=O)C=Cc2ccccc21", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 5.0710 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9162 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0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\n 13 14 2 0\n 16 17 1 0\nA 11\nOSO2H\nA 17\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.471735867933967, 0.04004269291508499, 0.6343171585792896, 0.2843848394785628 ], "category_id": 1, "smiles": "[H]C1([H])C(O)=CC(O[SH](=O)=O)c2ccccc21", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 5.3996 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3711 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4281 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6855 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9713 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2571 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2571 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9713 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6855 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3996 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3996 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1138 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1138 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8280 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 13 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 13 14 1 0\nA 11\nOSO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.16758379189594796, 0.3742765990838557, 0.38969484742371185, 0.630876712866237 ], "category_id": 1, "smiles": "[H].[H]C1([H])c2ccccc2C(O[SH](=O)=O)CC1(O)[NH](=N)c1ccccc1", "molfile": "\n RDKit 2D\n\n 17 17 0 0 0 0 0 0 0 0999 V2000\n 5.3358 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3353 -0.4173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3363 -0.4173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6684 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0009 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3335 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3335 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0009 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6684 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3358 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3358 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0032 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0032 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0042 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8949 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0037 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5604 -0.4173 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 13 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\n 13 14 1 0\n 13 16 1 0\n 14 15 1 0\nA 11\nOSO2H\nA 14\nNHNH\nA 15\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.45572786393196596, 0.40941610511137916, 0.671335667833917, 0.6120811631305849 ], "category_id": 1, "smiles": "B.[H]C1=C(NNc2ccccc2)C=C2=C(C=CC=C2)C1[O-]", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.0000 4.8971 0.0000 B 0 0 0 0 0 15 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 3.8971 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 14 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 1 0\n 5 13 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 13 14 1 0\nM CHG 1 7 -1\nA 11\nNHNHPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45572786393196596, 0.40941610511137916, 0.671335667833917, 0.6120811631305849 ], "category_id": 1, "smiles": "B.[H]C1=C(NNc2ccccc2)C=C2=C(C=CC=C2)C1[O-]", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.0000 4.8971 0.0000 B 0 0 0 0 0 15 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 3.8971 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 14 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 1 0\n 5 13 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 13 14 1 0\nM CHG 1 7 -1\nA 11\nNHNHPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.16758379189594796, 0.3742765990838557, 0.38969484742371185, 0.630876712866237 ], "category_id": 1, "smiles": "[H].[H]C1([H])c2ccccc2C(O[SH](=O)=O)CC1(O)[NH](=N)c1ccccc1", "molfile": "\n RDKit 2D\n\n 17 17 0 0 0 0 0 0 0 0999 V2000\n 5.3358 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3353 -0.4173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3363 -0.4173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6684 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0009 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3335 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3335 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0009 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6684 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3358 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3358 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0032 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0032 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0042 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8949 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0037 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5604 -0.4173 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 13 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\n 13 14 1 0\n 13 16 1 0\n 14 15 1 0\nA 11\nOSO2H\nA 14\nNHNH\nA 15\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45572786393196596, 0.40941610511137916, 0.671335667833917, 0.6120811631305849 ], "category_id": 1, "smiles": "B.[H]C1=C(NNc2ccccc2)C=C2=C(C=CC=C2)C1[O-]", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.0000 4.8971 0.0000 B 0 0 0 0 0 15 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 3.8971 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 14 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 1 0\n 5 13 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 13 14 1 0\nM CHG 1 7 -1\nA 11\nNHNHPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7343671835917959, 0.37019061001088777, 0.896448224112056, 0.630876712866237 ], "category_id": 1, "smiles": "c1ccc([NH+][NH+]c2ccc3ccccc3c2)cc1", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n 3.5872 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2613 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9353 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9353 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6094 -3.0945 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 8.6094 -4.9843 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.9353 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9353 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2613 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5872 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9132 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2391 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2391 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9132 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5872 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2613 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2613 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5872 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 17 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 7 16 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 10 15 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 2 0\n 17 18 2 0\nM CHG 2 5 1 6 1\nM RAD 2 5 2 6 2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7343671835917959, 0.37019061001088777, 0.896448224112056, 0.630876712866237 ], "category_id": 1, "smiles": "c1ccc([NH+][NH+]c2ccc3ccccc3c2)cc1", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n 3.5872 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2613 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9353 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9353 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6094 -3.0945 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 8.6094 -4.9843 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.9353 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9353 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2613 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5872 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9132 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2391 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2391 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9132 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5872 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2613 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2613 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5872 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 17 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 7 16 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 10 15 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 2 0\n 17 18 2 0\nM CHG 2 5 1 6 1\nM RAD 2 5 2 6 2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.45572786393196596, 0.40941610511137916, 0.671335667833917, 0.6120811631305849 ], "category_id": 1, "smiles": "B.[H]C1=C(NNc2ccccc2)C=C2=C(C=CC=C2)C1[O-]", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.0000 4.8971 0.0000 B 0 0 0 0 0 15 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 3.8971 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 14 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 1 0\n 5 13 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 13 14 1 0\nM CHG 1 7 -1\nA 11\nNHNHPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2586293146573287, 0.7117792965110006, 0.43621810905452724, 0.9708310037371627 ], "category_id": 1, "smiles": "[H]C1(C2C=CC=CC2=[NH2+])C(=N)C=Cc2ccccc21", "molfile": "\n RDKit 2D\n\n 19 21 0 0 0 0 0 0 0 0999 V2000\n 0.2649 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2649 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9425 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6201 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2977 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6201 -4.0394 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2977 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6201 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6201 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2977 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9753 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9753 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6529 -3.0945 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 6.9753 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9753 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2977 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6201 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9425 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6529 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 17 1 0\n 5 6 1 0\n 5 7 1 0\n 5 14 1 0\n 7 8 1 0\n 7 12 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\n 14 19 2 0\n 15 16 2 0\n 16 17 1 0\n 17 18 2 0\nM CHG 1 13 1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5007503751875938, 0.7199512746569363, 0.7168584292146073, 0.9691966081079755 ], "category_id": 1, "smiles": "[H].[H]C12C=CC=CC1([NH2+])Nc1ccc3ccccc3c12", "molfile": "\n RDKit 2D\n\n 20 22 0 0 0 0 0 0 0 0999 V2000\n 0.2222 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2222 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0002 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6670 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3339 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7784 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7782 -2.9370 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5560 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3339 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2230 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4453 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6675 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6677 -2.7008 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 8.5564 -4.4331 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1118 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1118 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3339 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6670 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0002 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5568 -3.4882 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 1 19 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 18 1 0\n 5 6 1 0\n 5 15 2 0\n 6 7 1 0\n 6 8 1 0\n 6 12 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\n 15 16 1 0\n 16 17 2 0\n 17 18 1 0\n 18 19 2 0\nM CHG 1 13 1\nM RAD 1 13 2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5007503751875938, 0.7199512746569363, 0.7168584292146073, 0.9691966081079755 ], "category_id": 1, "smiles": "[H].[H]C12C=CC=CC1([NH2+])Nc1ccc3ccccc3c12", "molfile": "\n RDKit 2D\n\n 20 22 0 0 0 0 0 0 0 0999 V2000\n 0.2222 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2222 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 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6 8 1 0\n 6 12 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\n 15 16 1 0\n 16 17 2 0\n 17 18 1 0\n 18 19 2 0\nM CHG 1 13 1\nM RAD 1 13 2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7873936968484242, 0.7183168790277491, 0.9429714857428715, 0.9659278168496013 ], "category_id": 1, "smiles": "c1ccc2c(c1)ccc1[nH]c3ccccc3c12", "molfile": "\n RDKit 2D\n\n 17 20 0 0 0 0 0 0 0 0999 V2000\n 0.2424 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2424 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0201 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7169 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4946 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8178 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6058 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4138 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4339 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5651 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7571 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6459 -4.4331 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1915 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1915 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4946 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7169 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0201 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 17 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 16 1 0\n 5 6 1 0\n 5 13 2 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\n 14 15 2 0\n 15 16 1 0\n 16 17 2 0\nM END\n" } ] } ], "Bucherer reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1040520260130065, 0.06274508625684214, 0.3216608304152076, 0.2603253578741323 ], "category_id": 1, "smiles": "[HH].[H]OC1=CC2=CC=C=CC=2C=C1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 12 2 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 11 2 0\n 5 6 2 0\n 6 7 1 0\n 6 9 1 0\n 7 8 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.400200100050025, 0.03204004404604705, 0.6748374187093547, 0.3230704441309744 ], "category_id": 1, "smiles": "[H].[H]C1([H])C(=O)C=Cc2ccccc21.[O-].[O-]", "molfile": "\n RDKit 2D\n\n 16 14 0 0 0 0 0 0 0 0999 V2000\n 12.5769 -0.6535 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 6.3380 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1593 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3380 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4176 -1.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3380 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1593 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4176 -9.0000 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\n 8.4176 -9.0000 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 10 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 9 14 1 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\nM CHG 2 15 -1 16 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.400200100050025, 0.03204004404604705, 0.6748374187093547, 0.3230704441309744 ], "category_id": 1, "smiles": "[H].[H]C1([H])C(=O)C=Cc2ccccc21.[O-].[O-]", "molfile": "\n RDKit 2D\n\n 16 14 0 0 0 0 0 0 0 0999 V2000\n 12.5769 -0.6535 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 6.3380 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1593 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3380 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4176 -1.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3380 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1593 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4176 -9.0000 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\n 8.4176 -9.0000 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 10 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 9 14 1 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\nM CHG 2 15 -1 16 -1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.1040520260130065, 0.06274508625684214, 0.3216608304152076, 0.2603253578741323 ], "category_id": 1, "smiles": "[HH].[H]OC1=CC2=CC=C=CC=2C=C1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 12 2 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 11 2 0\n 5 6 2 0\n 6 7 1 0\n 6 9 1 0\n 7 8 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.400200100050025, 0.03204004404604705, 0.6748374187093547, 0.3230704441309744 ], "category_id": 1, "smiles": "[H].[H]C1([H])C(=O)C=Cc2ccccc21.[O-].[O-]", "molfile": "\n RDKit 2D\n\n 16 14 0 0 0 0 0 0 0 0999 V2000\n 12.5769 -0.6535 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 6.3380 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1593 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3380 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4176 -1.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3380 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1593 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4176 -9.0000 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\n 8.4176 -9.0000 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 10 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 9 14 1 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\nM CHG 2 15 -1 16 -1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6963481740870435, 0.052065071574826455, 0.9154577288644322, 0.302377915684569 ], "category_id": 1, "smiles": "[H]OC1=CC(O[SH4][N+](=O)[O-])c2ccccc2C1([H])[H]", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 5.6216 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6079 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6354 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8706 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0275 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2765 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2765 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0275 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8706 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6216 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6216 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3726 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3726 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2158 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9668 -2.6220 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 13 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 1 0\nA 11\nOSO2NH4\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6963481740870435, 0.052065071574826455, 0.9154577288644322, 0.302377915684569 ], "category_id": 1, "smiles": "[H]OC1=CC(O[SH4][N+](=O)[O-])c2ccccc2C1([H])[H]", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 5.6216 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6079 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6354 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8706 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0275 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2765 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2765 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0275 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8706 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6216 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6216 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3726 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3726 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2158 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9668 -2.6220 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 13 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 1 0\nA 11\nOSO2NH4\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.400200100050025, 0.03204004404604705, 0.6748374187093547, 0.3230704441309744 ], "category_id": 1, "smiles": "[H].[H]C1([H])C(=O)C=Cc2ccccc21.[O-].[O-]", "molfile": "\n RDKit 2D\n\n 16 14 0 0 0 0 0 0 0 0999 V2000\n 12.5769 -0.6535 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 6.3380 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1593 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3380 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4176 -1.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3380 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1593 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0796 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4176 -9.0000 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\n 8.4176 -9.0000 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 10 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 9 14 1 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\nM CHG 2 15 -1 16 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.29664832416208103, 0.4105130643399778, 0.5672836418209104, 0.6174383488040317 ], "category_id": 1, "smiles": "N.O=C1Cc2ccccc2C(O[SH](=O)=O)C1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 6.8898 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6850 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4803 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4134 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4134 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4803 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6850 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8898 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8898 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9567 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9567 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1614 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6063 -2.5433 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 2 0\nA 9\nOSO2H\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6518259129564783, 0.4025030533284661, 0.8749374687343672, 0.6241133579802915 ], "category_id": 1, "smiles": "NC1(O)Cc2ccccc2C(O[SH4][N+](=O)[O-])C1", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 6.4855 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3591 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3390 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3190 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3190 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3390 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3591 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4855 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4855 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5055 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5055 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8446 -1.8346 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6750 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 1 0\nA 9\nOSO2NH4\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6518259129564783, 0.4025030533284661, 0.8749374687343672, 0.6241133579802915 ], "category_id": 1, "smiles": "NC1(O)Cc2ccccc2C(O[SH4][N+](=O)[O-])C1", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 6.4855 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3591 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3390 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3190 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3190 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3390 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3591 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4855 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4855 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5055 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5055 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8446 -1.8346 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6750 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 1 0\nA 9\nOSO2NH4\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.29664832416208103, 0.4105130643399778, 0.5672836418209104, 0.6174383488040317 ], "category_id": 1, "smiles": "N.O=C1Cc2ccccc2C(O[SH](=O)=O)C1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 6.8898 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6850 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4803 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4134 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4134 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4803 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6850 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8898 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8898 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9567 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9567 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1614 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6063 -2.5433 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 2 0\nA 9\nOSO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6518259129564783, 0.4025030533284661, 0.8749374687343672, 0.6241133579802915 ], "category_id": 1, "smiles": "NC1(O)Cc2ccccc2C(O[SH4][N+](=O)[O-])C1", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 6.4855 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3591 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3390 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3190 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3190 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3390 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3591 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4855 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4855 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5055 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5055 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8446 -1.8346 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6750 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 1 0\nA 9\nOSO2NH4\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8979489744872436, 0.4305380918687572, 0.9454727363681841, 0.5006256882194852 ], "category_id": 2, "text": [ "H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.12906453226613307, 0.7222359928713106, 0.3471735867933967, 0.9825613507454429 ], "category_id": 1, "smiles": "[I-].[NH2+]C1(O)Cc2ccccc2C(O[SH4][N+](=O)[O-])C1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 5.2946 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6180 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9414 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2647 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2647 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9414 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6180 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2946 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2946 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8830 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8830 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8243 -2.9370 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 7.8537 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9422 -4.5118 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 1 0\nM CHG 2 12 1 14 -1\nM RAD 1 12 2\nA 9\nOSO2NH4\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.12906453226613307, 0.7222359928713106, 0.3471735867933967, 0.9825613507454429 ], "category_id": 1, "smiles": "[I-].[NH2+]C1(O)Cc2ccccc2C(O[SH4][N+](=O)[O-])C1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 5.2946 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6180 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9414 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2647 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2647 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9414 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6180 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2946 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2946 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8830 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8830 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8243 -2.9370 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 7.8537 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9422 -4.5118 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 1 0\nM CHG 2 12 1 14 -1\nM RAD 1 12 2\nA 9\nOSO2NH4\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4062031015507754, 0.706215970848287, 0.6233116558279139, 0.9652063268871673 ], "category_id": 1, "smiles": "[H]C1=C2C=CC=CC2C([O-])C([H])C1=N", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 0.2638 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2638 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9348 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6057 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2766 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2766 -7.6614 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 6.9475 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5305 -5.6929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9475 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2766 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2766 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6057 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9348 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5305 -1.6772 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 12 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 14 2 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\nM CHG 1 6 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4062031015507754, 0.706215970848287, 0.6233116558279139, 0.9652063268871673 ], "category_id": 1, "smiles": "[H]C1=C2C=CC=CC2C([O-])C([H])C1=N", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 0.2638 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2638 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9348 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6057 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2766 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2766 -7.6614 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 6.9475 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5305 -5.6929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9475 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2766 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2766 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6057 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9348 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5305 -1.6772 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 12 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 14 2 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\nM CHG 1 6 -1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.12906453226613307, 0.7222359928713106, 0.3471735867933967, 0.9825613507454429 ], "category_id": 1, "smiles": "[I-].[NH2+]C1(O)Cc2ccccc2C(O[SH4][N+](=O)[O-])C1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 5.2946 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6180 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9414 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2647 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2647 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9414 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6180 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2946 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2946 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8830 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8830 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8243 -2.9370 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 7.8537 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9422 -4.5118 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 1 0\nM CHG 2 12 1 14 -1\nM RAD 1 12 2\nA 9\nOSO2NH4\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4062031015507754, 0.706215970848287, 0.6233116558279139, 0.9652063268871673 ], "category_id": 1, "smiles": "[H]C1=C2=C(C=CC=C2)C([O-])C([H])C1=N", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 3.8971 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 14 2 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\nM CHG 1 6 -1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6758379189594798, 0.7789735708695189, 0.8914457228614308, 0.911138752559463 ], "category_id": 1, "smiles": "Nc1ccc2ccccc2c1", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 0.5125 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5125 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9290 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1747 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5912 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0077 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0077 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.4243 -0.4961 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5912 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1747 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9290 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 10 11 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6758379189594798, 0.7789735708695189, 0.8914457228614308, 0.911138752559463 ], "category_id": 1, "smiles": "Nc1ccc2ccccc2c1", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 0.5125 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5125 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9290 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1747 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5912 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0077 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0077 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.4243 -0.4961 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5912 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1747 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9290 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 10 11 2 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4062031015507754, 0.706215970848287, 0.6233116558279139, 0.9652063268871673 ], "category_id": 1, "smiles": "[H]C1=C2=C(C=CC=C2)C([O-])C([H])C1=N", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 3.8971 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 14 2 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\nM CHG 1 6 -1\nM END\n" } ] } ], "Bucherer\u2013Bergs reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0720360180090045, 0.08712396399204628, 0.24862431215607803, 0.34737888207085116 ], "category_id": 1, "smiles": "*C(*)=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -9.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 15.1572 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1572 -9.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 15.1572 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\nM ISO 2 1 1 3 2\nA 1\n1*\nA 3\n2*\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3151575787893947, 0.07930514671070878, 0.44222111055527763, 0.3149866390481673 ], "category_id": 1, "smiles": "[1*]C([2*])([NH2+])O", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 6.8504 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8504 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1804 -4.4331 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5203 -4.4331 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.8504 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nM CHG 1 4 1\nM RAD 1 4 2\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3151575787893947, 0.07930514671070878, 0.44222111055527763, 0.3149866390481673 ], "category_id": 1, "smiles": "[1*]C([2*])([NH2+])O", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 6.8504 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8504 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1804 -4.4331 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5203 -4.4331 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.8504 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nM CHG 1 4 1\nM RAD 1 4 2\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5572786393196598, 0.0, 0.6503251625812907, 0.20440622321210855 ], "category_id": 1, "smiles": "[1*]C([2*])=[NH2+]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 4.8000 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2800 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9200 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8000 -2.3071 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM CHG 1 4 1\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.5292646323161581, 0.26248886587347275, 0.575287643821911, 0.3563146732495226 ], "category_id": 2, "text": [ "NC" ] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5572786393196598, 0.0, 0.6503251625812907, 0.20440622321210855 ], "category_id": 1, "smiles": "[1*]C([2*])=[NH2+]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 4.8000 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2800 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9200 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8000 -2.3071 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM CHG 1 4 1\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.5292646323161581, 0.26248886587347275, 0.575287643821911, 0.3563146732495226 ], "category_id": 2, "text": [ "NC" ] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.696848424212106, 0.0, 0.8489244622311155, 0.3686013861201958 ], "category_id": 1, "smiles": "O=C=O.[1*]C([1*])([NH2+])C#N", "molfile": "\n RDKit 2D\n\n 9 7 0 0 0 0 0 0 0 0999 V2000\n 4.6586 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6586 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4021 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6586 -4.2756 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.6240 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5893 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0919 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0572 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0954 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 3 0\n 7 8 2 0\n 8 9 2 0\nM CHG 1 4 1\nM RAD 1 4 2\nM ISO 2 2 1 3 1\nA 2\nR1\nA 3\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0895447723861931, 0.49817035821093125, 0.2381190595297649, 0.8410813446924467 ], "category_id": 1, "smiles": "[1*]C([2*])(C#N)NC(=O)O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 2.6640 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9134 -1.9921 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0656 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4147 -2.1496 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6982 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8399 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8399 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5013 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6430 -7.3465 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 3 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.31615807903951976, 0.5138079927736062, 0.45672836418209106, 0.8433152924871146 ], "category_id": 1, "smiles": "[1*]C1([2*])[NH+]C(=O)OC1=N", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 2.7692 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0478 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1226 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6402 -2.0709 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.5113 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7565 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9125 -5.5354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6673 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3201 -7.4252 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 1 0\n 8 9 2 0\nM CHG 1 4 1\nM RAD 1 4 2\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.31615807903951976, 0.5138079927736062, 0.45672836418209106, 0.8433152924871146 ], "category_id": 1, "smiles": "[1*]C1([2*])[NH+]C(=O)OC1=N", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 2.7692 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0478 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1226 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6402 -2.0709 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 6.5113 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7565 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9125 -5.5354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6673 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3201 -7.4252 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 1 0\n 8 9 2 0\nM CHG 1 4 1\nM RAD 1 4 2\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5157578789394698, 0.5205098361576098, 0.6803401700850426, 0.852251083665786 ], "category_id": 1, "smiles": "*C(*)([N-]=C=O)C([NH2+])=O.*O", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.5981 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 1.2990 4.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 5.0981 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 0.5490 5.6471 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 6.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 8.2452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 3.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5490 3.0490 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 1.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 9 1 0\n 6 7 2 0\n 7 8 2 0\n 9 10 1 0\n 9 11 2 0\nM CHG 2 6 -1 10 1\nM ISO 2 3 1 5 2\nA 1\n*\nA 3\n1*\nA 5\n2*\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5157578789394698, 0.5205098361576098, 0.6803401700850426, 0.852251083665786 ], "category_id": 1, "smiles": "*C(*)([N-]=C=O)C([NH2+])=O.*O", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.5981 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 1.2990 4.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 5.0981 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 0.5490 5.6471 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 6.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 8.2452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 3.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5490 3.0490 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 1.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 9 1 0\n 6 7 2 0\n 7 8 2 0\n 9 10 1 0\n 9 11 2 0\nM CHG 2 6 -1 10 1\nM ISO 2 3 1 5 2\nA 1\n*\nA 3\n1*\nA 5\n2*\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7628814407203601, 0.5272116795416134, 0.9019509754877438, 0.8019872582857592 ], "category_id": 1, "smiles": "[1*]C1([2*])NC(=O)NC1=O", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 3.2949 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4248 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3358 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4321 -1.5197 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7475 -2.9370 0.0000 C 0 0 0 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15 1 0\n 1 17 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 8 9 1 0\n 9 10 2 0\n 9 11 1 0\n 11 12 1 0\n 12 13 1 0\n 12 17 1 0\n 13 14 1 0\n 14 15 1 0\n 14 16 2 0\nM CHG 2 1 -1 17 -1\nA 12\nMeN\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.33366683341670833, 0.7501875937968985, 0.4487243621810905, 0.8170445900033351 ], "category_id": 1, "smiles": "*C=C", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 1.1732 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1512 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.0677 -2.4646 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\nA 3\nBr2\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.47873936968484243, 0.5556945139236285, 0.6863431715857929, 0.7640799566449893 ], "category_id": 1, "smiles": "CN(CC[N+](=O)[O-])CC[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 5.9742 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9742 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 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0.37168584292146073, 0.1850173641734162 ], "category_id": 1, "smiles": "[N-]=[N+]=CC(=O)O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 11.4134 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1444 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8045 -4.7480 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 0.0000 -4.7480 0.0000 N 0 0 0 0 0 2 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 2 0\nM CHG 2 3 1 4 -1\nA 2\nCO2H\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4047023511755878, 0.052036133673773306, 0.46823411705852924, 0.12141764523880437 ], "category_id": 2, "text": [ "[Rh]" ] } ], "products": [ { "category": "[Txt]", "bbox": [ 0.5097548774387194, 0.09732684261205748, 0.567783891945973, 0.18405373206834633 ], "category_id": 2, "text": [ "Nz ^" ] }, { "category": "[Mol]", "bbox": [ 0.6058029014507254, 0.08672688945628884, 0.8269134567283641, 0.18598099627848608 ], "category_id": 1, "smiles": "O=C(O)C=c1ccccc1", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 8.7095 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4140 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.1136 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\nA 1\nPh\nA 3\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04102051025512756, 0.41628906939018645, 0.327663831915958, 0.6128700188244413 ], "category_id": 1, "smiles": "*.*=CC(=O)OC.c1ccccc1", "molfile": "\n RDKit 2D\n\n 13 11 0 0 0 0 0 0 0 0999 V2000\n 27.9310 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0548 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0548 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 20.0136 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.9723 -2.3071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0548 -2.3071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8762 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9587 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9587 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 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0.5301 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5301 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7104 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8907 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6011 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 9 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\nA 2\nCO2H\nA 3\nRhJ\nA 10\nRhJ\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7933966983491746, 0.41147090886483706, 0.9214607303651826, 0.4798887883247983 ], "category_id": 2, "text": [ "reductive" ] }, { "category": "[Txt]", "bbox": [ 0.7873936968484242, 0.5184340725275933, 0.9289644822411206, 0.5878155840926244 ], "category_id": 2, "text": [ "elimination" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.1455727863931966, 0.7506694098494334, 0.3931965982991496, 0.9221959245518714 ], "category_id": 1, "smiles": "COC(=O)C1C2C=CC=CC21", "molfile": "\n RDKit 2D\n\n 8 9 0 0 0 0 0 0 0 0999 V2000\n 16.8683 -4.0394 0.0000 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0 0 0 0 0 0 0 0 0 0\n 13.9104 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 20.0569 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4099 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 26.8504 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 32.3499 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 38.1728 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 3 0\n 7 8 1 0\nM ISO 2 2 1 8 2\nA 2\nR1\nA 4\nGu\nA 5\nX\nA 8\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6048024012006002, 0.08427828104739732, 0.9004502251125562, 0.29571326683297305 ], "category_id": 1, "smiles": "**(C#C[1*])C#C[2*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 8.0875 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9410 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9104 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 20.0569 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 19.4099 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 26.8504 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 32.3499 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 38.1728 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 3 0\n 7 8 1 0\nM ISO 2 2 1 8 2\nA 2\nR1\nA 4\nGu\nA 5\nX\nA 8\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Txt]", "bbox": [ 0.38369184592296146, 0.7511116977557516, 0.4487243621810905, 0.8693970044889408 ], "category_id": 2, "text": [ "CuX" ] }, { "category": "[Mol]", "bbox": [ 0.512256128064032, 0.7451974324190921, 0.7553776888444222, 0.8620041728181165 ], "category_id": 1, "smiles": "[1*]C#CC#C[7*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 14.3786 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3550 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 24.9230 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 34.5087 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 45.0531 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 55.1181 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\n 4 5 3 0\n 5 6 1 0\nM ISO 2 2 1 6 7\nA 2\nR1\nA 6\nR7\nM END\n" } ] } ], "Camps quinoline synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1950975487743872, 0.04691290368802492, 0.3411705852926463, 0.2116665535447791 ], "category_id": 1, "smiles": "[1*]CC(=O)c1ccccc1NC(=O)C[2*]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 6.9973 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7077 -1.5197 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2868 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6541 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6541 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2868 -5.3780 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2868 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9973 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7077 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6541 -8.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9437 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2332 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2332 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9437 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2868 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 15 2 0\n 4 5 2 0\n 4 14 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 1 0\n 7 8 1 0\n 7 10 2 0\n 8 9 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\nM ISO 2 2 1 9 2\nA 2\nR1\nA 9\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.35967983991996, 0.1049955463493891, 0.423711855927964, 0.13682930242340602 ], "category_id": 2, "text": [ "NaOR" ] }, { "category": "[Txt]", "bbox": [ 0.36368184092046024, 0.14967450224274617, 0.42021010505252626, 0.18039128441942914 ], "category_id": 2, "text": [ "ROH" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4517258629314657, 0.061992051302032926, 0.6208104052026013, 0.18374220611143094 ], "category_id": 1, "smiles": "[1*]c1c(C[2*])nc2ccccc2c1O", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 0.3651 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5555 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8676 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0580 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0580 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3701 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5605 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3701 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5605 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8726 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0580 -8.0551 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8676 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5555 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3651 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 3 12 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 11 1 0\n 9 10 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\nM ISO 2 7 1 10 2\nA 7\nR1\nA 10\nR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.6498249124562281, 0.04635441673935795, 0.8014007003501751, 0.18765161475209968 ], "category_id": 1, "smiles": "[1*]Cc1c([2*])c(O)nc2ccccc12", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 6.1217 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2381 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1217 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2381 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2381 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2603 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2825 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2825 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2603 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1217 -8.1339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0994 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0772 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0994 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0772 -3.5669 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 2 0\n 3 13 1 0\n 4 5 1 0\n 4 9 1 0\n 5 6 1 0\n 5 10 2 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 10 11 1 0\n 11 12 1 0\n 11 13 2 0\n 13 14 1 0\nM ISO 2 2 1 14 2\nA 2\nR1\nA 14\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.11105552776388194, 0.38368053373420374, 0.2571285642821411, 0.5758000440756392 ], "category_id": 1, "smiles": "[1*]C([H])C(=O)c1ccccc1NC(=O)C[2*]", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 5.8785 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2813 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4089 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4089 -5.8504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0061 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0061 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4089 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8785 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0141 -4.5906 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2813 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4089 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6032 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2004 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2004 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6032 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0061 -8.3701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 16 2 0\n 4 5 1 0\n 5 6 2 0\n 5 15 1 0\n 6 7 1 0\n 6 12 1 0\n 7 8 1 0\n 7 11 2 0\n 8 9 1 0\n 8 10 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\nM ISO 2 2 2 10 1\nA 2\nR2\nA 10\nR1\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.29164582291145574, 0.4216576462435573, 0.344672336168084, 0.47024601077758305 ], "category_id": 1, "smiles": "*", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 6.0330 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nOP\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3676838419209605, 0.39373329881020913, 0.535767883941971, 0.5651887920509667 ], "category_id": 1, "smiles": "[1*]/C=C(\\[O-])c1ccccc1NC(=O)C[2*]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 6.7113 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4322 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0765 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0765 -0.8898 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 3.5277 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5277 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0765 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0555 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0020 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9809 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0020 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8929 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2581 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2581 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8929 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 5 15 1 0\n 6 7 1 0\n 6 12 1 0\n 7 8 1 0\n 8 9 1 0\n 8 11 2 0\n 9 10 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\nM CHG 1 4 -1\nM ISO 2 2 1 10 2\nA 2\nR1\nA 10\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3676838419209605, 0.39373329881020913, 0.535767883941971, 0.5651887920509667 ], "category_id": 1, "smiles": "[1*]/C=C(\\[O-])c1ccccc1NC(=O)C[2*]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 6.7113 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4322 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0765 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0765 -0.8898 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 3.5277 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5277 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0765 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0555 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0020 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9809 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0020 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8929 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2581 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2581 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8929 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 5 15 1 0\n 6 7 1 0\n 6 12 1 0\n 7 8 1 0\n 8 9 1 0\n 8 11 2 0\n 9 10 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\nM CHG 1 4 -1\nM ISO 2 2 1 10 2\nA 2\nR1\nA 10\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6018009004502252, 0.4216576462435573, 0.7713856928464232, 0.5640718181536329 ], "category_id": 1, "smiles": "[1*]C1C(=O)c2ccccc2NC1(O)C[2*]", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 8.1393 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0176 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1393 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1393 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0176 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8959 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2610 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3827 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3827 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5044 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6261 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6261 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5044 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2610 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2610 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 14 1 0\n 3 4 1 0\n 3 5 1 0\n 3 7 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 9 14 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 2 0\nM ISO 2 2 1 6 2\nA 2\nR1\nA 6\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6018009004502252, 0.4216576462435573, 0.7713856928464232, 0.5640718181536329 ], "category_id": 1, "smiles": "[1*]C1C(=O)c2ccccc2NC1(O)C[2*]", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 8.1393 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0176 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1393 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1393 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0176 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8959 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2610 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3827 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3827 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5044 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6261 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6261 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5044 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2610 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2610 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 14 1 0\n 3 4 1 0\n 3 5 1 0\n 3 7 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 9 14 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 2 0\nM ISO 2 2 1 6 2\nA 2\nR1\nA 6\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7998999499749875, 0.4490235067282385, 0.8454227113556778, 0.4903515409295937 ], "category_id": 2, "text": [ "H" ] }, { "category": "[Txt]", "bbox": [ 0.7878939469734867, 0.503196740748934, 0.8509254627313657, 0.5350304968229508 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Idt]", "bbox": [ 0.8674337168584292, 0.48364969754559023, 0.8899449724862432, 0.5154834536196071 ], "category_id": 3, "text": [ "2" ] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.12156078039019509, 0.7355273113943906, 0.2661330665332666, 0.9399335346064992 ], "category_id": 1, "smiles": "[1*]CC(=O)c1ccccc1NC(=O)C([2*])[H]", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 5.6212 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9953 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2472 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9355 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9355 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2472 -4.0394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2472 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6212 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9953 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6212 -7.8189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9355 -6.3228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5615 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.1874 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.1874 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5615 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2472 0.4488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 16 2 0\n 4 5 2 0\n 4 15 1 0\n 5 6 1 0\n 5 12 1 0\n 6 7 1 0\n 7 8 1 0\n 7 11 2 0\n 8 9 1 0\n 8 10 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\nM ISO 2 2 1 9 2\nA 2\nR1\nA 9\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3806903451725863, 0.7506064590083987, 0.5322661330665333, 0.927646821735826 ], "category_id": 1, "smiles": "[1*]CC(=O)c1ccccc1N/C(O)=C/[2*]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 9.5703 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6864 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6864 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5703 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7271 -9.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8432 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8839 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8839 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8432 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8432 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8839 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7271 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7271 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 12 14 1 0\n 14 15 1 0\nM ISO 2 1 2 15 1\nA 1\nR2\nA 15\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3806903451725863, 0.7506064590083987, 0.5322661330665333, 0.927646821735826 ], "category_id": 1, "smiles": "[1*]CC(=O)c1ccccc1N/C(O)=C/[2*]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 9.5703 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6864 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6864 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5703 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7271 -9.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8432 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8839 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8839 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8432 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8432 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8839 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7271 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7271 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 12 14 1 0\n 14 15 1 0\nM ISO 2 1 2 15 1\nA 1\nR2\nA 15\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6143071535767884, 0.7506064590083987, 0.759879939969985, 0.9097752393784833 ], "category_id": 1, "smiles": "[1*]CC1(O)c2ccccc2NC(=O)C1[2*]", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 5.4474 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7651 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4474 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7651 -1.9921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7651 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7651 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0027 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2403 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2403 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0027 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4474 -7.1102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2099 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9723 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2099 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9723 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 14 1 0\n 5 6 2 0\n 5 10 1 0\n 6 7 1 0\n 6 11 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 1 0\n 12 13 2 0\n 12 14 1 0\n 14 15 1 0\nM ISO 2 2 1 15 2\nA 2\nR1\nA 15\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6143071535767884, 0.7506064590083987, 0.759879939969985, 0.9097752393784833 ], "category_id": 1, "smiles": "[1*]CC1(O)c2ccccc2NC(=O)C1[2*]", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 5.4474 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7651 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4474 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7651 -1.9921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7651 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7651 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0027 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2403 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2403 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0027 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4474 -7.1102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2099 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9723 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2099 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9723 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 14 1 0\n 5 6 2 0\n 5 10 1 0\n 6 7 1 0\n 6 11 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 1 0\n 12 13 2 0\n 12 14 1 0\n 14 15 1 0\nM ISO 2 2 1 15 2\nA 2\nR1\nA 15\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7863931965982992, 0.7969608757477565, 0.832416208104052, 0.8382889099491119 ], "category_id": 2, "text": [ "H" ] }, { "category": "[Txt]", "bbox": [ 0.7753876938469234, 0.8477831880764503, 0.83991995997999, 0.8796169441504671 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Idt]", "bbox": [ 0.8589294647323662, 0.8254437101297717, 0.8814407203601801, 0.8561604923064547 ], "category_id": 3, "text": [ "3" ] } ] } ], "Cannizzaro reaction.png": [], "Carroll rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03651825912956478, 0.1052894868486875, 0.20060030015007504, 0.4574646669977457 ], "category_id": 1, "smiles": "C=CCOC(=O)CC(C)=O", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 10.8957 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3268 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9350 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4547 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9744 -4.3543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9744 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4547 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9350 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4547 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3268 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 2 0\n 3 4 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.25062531265632815, 0.20573807775030892, 0.2771385692846423, 0.2819821889165999 ], "category_id": 2, "text": [ "4" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.31265632816408206, 0.05203963143096049, 0.47723861930965483, 0.45141354706391307 ], "category_id": 1, "smiles": "[H]O/C(=C\\C(C)=O)OCC=C", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 9.7638 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3543 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1496 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9449 -4.9055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9449 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1496 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3543 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1496 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3543 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 2 0\n 4 5 1 0\n 4 9 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 9 10 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.31265632816408206, 0.05203963143096049, 0.47723861930965483, 0.45141354706391307 ], "category_id": 1, "smiles": "[H]O/C(=C\\C(C)=O)OCC=C", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 9.7638 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3543 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1496 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9449 -4.9055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9449 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1496 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3543 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1496 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3543 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 2 0\n 4 5 1 0\n 4 9 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 9 10 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5062531265632816, 0.19726650984294325, 0.7288644322161081, 0.29408442878426505 ], "category_id": 2, "text": [ "[3,3]-sigmatropic" ] }, { "category": "[Txt]", "bbox": [ 0.5182591295647824, 0.34975473217552516, 0.7188594297148574, 0.4368908592227148 ], "category_id": 2, "text": [ "rearrangement" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7773886943471736, 0.06535209528539224, 0.9409704852426213, 0.4659362349051113 ], "category_id": 1, "smiles": "[H]OC(=O)C(CC=C)C(C)=O", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 9.5786 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3981 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2176 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1150 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1150 -1.2047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2176 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8566 -4.9055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2176 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1150 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8566 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3981 -1.2047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 1 0\n 3 8 1 0\n 4 5 1 0\n 4 7 2 0\n 5 6 1 0\n 8 9 1 0\n 9 10 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7773886943471736, 0.06535209528539224, 0.9409704852426213, 0.4659362349051113 ], "category_id": 1, "smiles": "[H]OC(=O)C(CC=C)C(C)=O", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 9.5786 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3981 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2176 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1150 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1150 -1.2047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2176 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8566 -4.9055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2176 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1150 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8566 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3981 -1.2047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 1 0\n 3 8 1 0\n 4 5 1 0\n 4 7 2 0\n 5 6 1 0\n 8 9 1 0\n 9 10 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.19809904952476237, 0.6740947606289532, 0.29064532266133064, 0.7745433515305747 ], "category_id": 2, "text": [ "COz" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.33466733366683343, 0.5228167622831379, 0.43621810905452724, 0.9173497819690245 ], "category_id": 1, "smiles": "[H]O/C(C)=C/CC=C", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.4687 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2226 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2226 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4687 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0254 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0254 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2226 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4687 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 5 2 0\n 3 4 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.33466733366683343, 0.5228167622831379, 0.43621810905452724, 0.9173497819690245 ], "category_id": 1, "smiles": "[H]O/C(C)=C/CC=C", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.4687 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2226 -3.6457 0.0000 C 0 0 0 0 0 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0 0 0 0 0 0 0 0 0 0\n 3.3418 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0826 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0826 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3418 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6482 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3418 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 2 0\nM END\n" } ] } ], "Castro\u2013Stephens coupling.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.06303151575787894, 0.2331291630067002, 0.21410705352676337, 0.3129391467387237 ], "category_id": 1, "smiles": "*C=C=[Cu]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 14.0026 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1371 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 23.8681 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 35.3248 -4.7480 0.0000 Cu 0 0 0 0 0 2 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 2 0\nM RAD 1 4 2\nA 2\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2416208104052026, 0.1491186538150965, 0.3501750875437719, 0.274084286237607 ], "category_id": 2, "text": [ "ligands", "(solvent)" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3736868434217109, 0.11551445013845506, 0.5562781390695347, 0.3864483422813769 ], "category_id": 1, "smiles": "CC.[1*]C#C[Cu](I)(I)I", "molfile": "\n RDKit 2D\n\n 9 7 0 0 0 0 0 0 0 0999 V2000\n 7.1467 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6850 -3.0157 0.0000 Cu 0 0 0 0 0 4 0 0 0 0 0 0\n 3.5734 -6.4803 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5734 -0.1024 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6700 -4.4331 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4918 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1718 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0551 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8468 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 3 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 6 7 1 0\n 8 9 1 0\nM RAD 1 2 2\nM ISO 1 7 1\nA 7\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3736868434217109, 0.11551445013845506, 0.5562781390695347, 0.3864483422813769 ], "category_id": 1, "smiles": "CC.[1*]C#C[Cu](I)(I)I", "molfile": "\n RDKit 2D\n\n 9 7 0 0 0 0 0 0 0 0999 V2000\n 7.1467 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6850 -3.0157 0.0000 Cu 0 0 0 0 0 4 0 0 0 0 0 0\n 3.5734 -6.4803 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5734 -0.1024 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6700 -4.4331 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4918 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1718 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0551 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8468 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 3 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 6 7 1 0\n 8 9 1 0\nM RAD 1 2 2\nM ISO 1 7 1\nA 7\nR1\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5857928964482241, 0.23522942573649028, 0.6928464232116058, 0.44525569871549947 ], "category_id": 1, "smiles": "Ic1ccccc1.[2*]C", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 3.8767 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3434 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7308 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6126 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8428 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2755 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5899 -7.5827 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4780 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2478 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 2 0\n 3 9 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\nM ISO 1 2 2\nA 2\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7323661830915458, 0.028353546852166237, 0.9174587293646823, 0.4715089828378756 ], "category_id": 1, "smiles": "I[Cu](I)(C#C[Rf])[IH]c1ccccc1.[2*]C", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 6.1514 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8793 -8.3701 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 4.6308 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4191 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"molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 6.1514 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8793 -8.3701 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 4.6308 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4191 -5.4567 0.0000 Cu 0 0 0 0 0 4 0 0 0 0 0 0\n 2.4191 -7.5827 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4147 -6.3228 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4191 -3.2520 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7323 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3176 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5617 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2205 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6352 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3911 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3911 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5337 -2.4646 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\nM RAD 1 4 2\nM ISO 1 15 2\nA 15\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6938469234617308, 0.6111764543689167, 0.897448724362181, 0.9493187538651215 ], "category_id": 1, "smiles": "*[Cu]1(*)[IH]C2(=CC=CC=C2)C1#C[Rf]", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 3.2595 -3.5244 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8107 -3.1362 0.0000 Cu 0 0 0 0 0 4 0 0 0 0 0 0\n 1.4224 -4.5850 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3618 -2.7479 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1989 -1.6873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4979 -0.9373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7970 -1.6873 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 11 1 0\n 4 5 1 0\n 5 6 1 0\n 5 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"category_id": 2, "text": [ "AIHzRz" ] } ], "products": [ { "category": "[Txt]", "bbox": [ 0.3261630815407704, 0.44540399970977856, 0.3711855927963982, 0.6337462624441992 ], "category_id": 2, "text": [ "Hz^" ] }, { "category": "[Mol]", "bbox": [ 0.40670335167583793, 0.15525510847026566, 0.5407703851925963, 0.8526305137301474 ], "category_id": 1, "smiles": "*C#C[C@@H]([1*])O[Al](*)(*)([H])C", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4698 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9396 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3322 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8020 -6.4016 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3322 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9396 -1.2835 0.0000 Al 0 0 0 0 0 5 0 0 0 0 0 0\n 3.4731 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0973 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0839 -1.2835 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4698 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 3 0\n 3 4 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 7 11 1 0\n 4 6 1 6\nM ISO 1 5 1\nA 1\n*\nA 5\nR1\nA 8\n*\nA 9\n*\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.40670335167583793, 0.15525510847026566, 0.5407703851925963, 0.8526305137301474 ], "category_id": 1, "smiles": "*C#C[C@@H]([1*])O[Al](*)(*)([H])C", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4698 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9396 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3322 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8020 -6.4016 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3322 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9396 -1.2835 0.0000 Al 0 0 0 0 0 5 0 0 0 0 0 0\n 3.4731 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0973 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0839 -1.2835 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4698 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 3 0\n 3 4 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 7 11 1 0\n 4 6 1 6\nM ISO 1 5 1\nA 1\n*\nA 5\nR1\nA 8\n*\nA 9\n*\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5892946473236619, 0.28251339410163095, 0.720360180090045, 0.8780821708564206 ], "category_id": 1, "smiles": "*/C([H])=C/[C@@H]([1*])O[Al](*)*", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8255 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8255 -4.0394 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6511 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3883 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2139 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3883 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6511 -2.3071 0.0000 Al 0 0 0 0 0 3 0 0 0 0 0 0\n 2.8255 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3883 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\n 4 5 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 5 7 1 6\nM ISO 1 6 1\nA 1\n*\nA 6\nR1\nA 9\n*\nA 10\n*\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5892946473236619, 0.28251339410163095, 0.720360180090045, 0.8780821708564206 ], "category_id": 1, "smiles": "*/C([H])=C/[C@@H]([1*])O[Al](*)*", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8255 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8255 -4.0394 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6511 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3883 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2139 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3883 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6511 -2.3071 0.0000 Al 0 0 0 0 0 3 0 0 0 0 0 0\n 2.8255 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3883 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\n 4 5 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 5 7 1 6\nM ISO 1 6 1\nA 1\n*\nA 6\nR1\nA 9\n*\nA 10\n*\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7313656828414207, 0.36141353119307745, 0.8129064532266133, 0.5166686396633431 ], "category_id": 2, "text": [ "workup" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.8449224612306153, 0.2697875655384944, 0.9809904952476238, 0.6541075881452177 ], "category_id": 1, "smiles": "*/C=C/[C@H]([1*])O", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 4.9656 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4187 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6543 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2012 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.8899 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2012 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 1\nM ISO 1 5 1\nA 2\nR\nA 5\nR1\nM END\n" } ] } ], "Chan\u2013Lam C\u2013X coupling reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05152576288144072, 0.46851864594007037, 0.24412206103051526, 0.8279641679575847 ], "category_id": 1, "smiles": 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3 1 0\n 3 4 1 0\n 3 5 2 0\nA 2\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7498749374687343, 0.08546263013462888, 0.8724362181090545, 0.17317427685174797 ], "category_id": 1, "smiles": "*CC([H])=N", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 5.0773 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3622 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7924 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7924 -7.4252 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2598 -0.5748 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 2 0\nA 2\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5437718859429714, 0.08265135940651608, 0.6753376688344173, 0.17092526026925775 ], "category_id": 1, "smiles": "*/C=C(\\[H])N.[I-]", "molfile": "\n RDKit 2D\n\n 6 4 0 0 0 0 0 0 0 0999 V2000\n 4.8383 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3076 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2382 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2382 -7.4252 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6381 -0.5748 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0841 -3.6457 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 3 5 1 0\nM CHG 1 6 -1\nA 2\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.018009004502251125, 0.30530400107304917, 0.14657328664332167, 0.47173122817732643 ], "category_id": 1, "smiles": "*C([H])C([H])=O.N", "molfile": "\n RDKit 2D\n\n 7 5 0 0 0 0 0 0 0 0999 V2000\n 2.7427 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7427 -2.6220 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7542 -6.0079 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6626 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6626 -8.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5825 -4.8268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0340 0.1339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\nA 3\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.22511255627813906, 0.3013682220536913, 0.34967483741870936, 0.4812895486529099 ], "category_id": 1, "smiles": "*/C=C(\\[H])[O-].*CC([H])=O", "molfile": "\n RDKit 2D\n\n 10 8 0 0 0 0 0 0 0 0999 V2000\n 4.1697 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6603 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2075 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7358 -4.9055 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6556 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4528 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7358 -1.6772 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2311 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2311 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0093 -2.7008 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\nM CHG 1 10 -1\nA 2\nR\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.22511255627813906, 0.3013682220536913, 0.34967483741870936, 0.4812895486529099 ], "category_id": 1, "smiles": "*/C=C(\\[H])[O-].*CC([H])=O", "molfile": "\n RDKit 2D\n\n 10 8 0 0 0 0 0 0 0 0999 V2000\n 4.1697 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6603 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2075 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7358 -4.9055 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6556 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4528 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7358 -1.6772 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2311 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2311 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0093 -2.7008 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\nM CHG 1 10 -1\nA 2\nR\nA 7\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.38969484742371185, 0.3429750288297606, 0.4607303651825913, 0.37895929414960433 ], "category_id": 2, "text": [ "Aldol" ] }, { "category": "[Txt]", "bbox": [ 0.35467733866933465, 0.3935779019357909, 0.49524762381190596, 0.4267508965275218 ], "category_id": 2, "text": [ "condensation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5077538769384692, 0.3143000674030101, 0.6448224112056028, 0.4649841784298558 ], "category_id": 1, "smiles": "*CC([H])(O)C(*)([H])C([H])=O", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 2.9096 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8082 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1426 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3549 -5.9291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9096 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0316 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0316 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0522 -3.5669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 2 0\nA 2\nR\nA 8\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5077538769384692, 0.3143000674030101, 0.6448224112056028, 0.4649841784298558 ], "category_id": 1, "smiles": "*CC([H])(O)C(*)([H])C([H])=O", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 2.9096 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8082 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1426 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3549 -5.9291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9096 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0316 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0316 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0522 -3.5669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 2 0\nA 2\nR\nA 8\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6648324162081041, 0.3519710951597215, 0.7408704352176088, 0.39470241022703595 ], "category_id": 2, "text": [ "H2O" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7783891945972986, 0.30867752594678455, 0.9479739869934968, 0.48016504036166485 ], "category_id": 1, "smiles": "*C/C=C(\\*)C([H])=O.*CC=N", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 11.1111 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9239 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9239 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6492 -9.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1872 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4619 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4619 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1872 -1.5197 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6492 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6492 1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9239 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 2 0\nA 1\n*\nA 5\n*\nA 9\n*\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2271135567783892, 0.3013682220536913, 0.34967483741870936, 0.4812895486529099 ], "category_id": 1, "smiles": "*/C=C(\\[H])[O-].*CC([H])=O", "molfile": "\n RDKit 2D\n\n 10 8 0 0 0 0 0 0 0 0999 V2000\n 4.0987 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5809 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1699 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7233 -4.9055 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6274 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4110 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7233 -1.6772 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1589 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1589 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9069 -2.7008 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\nM CHG 1 10 -1\nA 2\nR\nA 7\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5077538769384692, 0.3143000674030101, 0.6448224112056028, 0.4649841784298558 ], "category_id": 1, "smiles": "*CC([H])(O)C(*)([H])C([H])=O", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 2.9096 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8082 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1426 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3549 -5.9291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9096 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0316 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0316 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0522 -3.5669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 2 0\nA 2\nR\nA 8\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5077538769384692, 0.3143000674030101, 0.6448224112056028, 0.4649841784298558 ], "category_id": 1, "smiles": "*CC([H])(O)C(*)([H])C([H])=O", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 2.9096 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8082 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1426 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3549 -5.9291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9302 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9096 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0316 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0316 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0522 -3.5669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 2 0\nA 2\nR\nA 8\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7498749374687343, 0.08546263013462888, 0.8724362181090545, 0.17317427685174797 ], "category_id": 1, "smiles": "*CC([H])=N", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 5.0773 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3622 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7924 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7924 -7.4252 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2598 -0.5748 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 2 0\nA 2\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4897448724362181, 0.5476355378363719, 0.5827913956978489, 0.6032986982530051 ], "category_id": 1, "smiles": "[H][NH3+]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 7.5726 -5.3780 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 14.5512 -5.3780 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nM CHG 1 1 1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.19609804902451225, 0.6061099689811179, 0.38819409704852426, 0.7106892400669137 ], "category_id": 1, "smiles": "*CC(/N=C\\C(*)[H])/C(*)=C\\O", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 4.2031 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2932 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2745 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3460 -7.7402 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7408 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.8423 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6205 -1.6772 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 19.3987 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2745 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2031 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3460 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4174 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\nA 2\nR\nA 8\nR\nA 10\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.19609804902451225, 0.6061099689811179, 0.38819409704852426, 0.7106892400669137 ], "category_id": 1, "smiles": "*CC(/N=C\\C(*)[H])/C(*)=C\\O", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 4.2031 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2932 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2745 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3460 -7.7402 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7408 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.8423 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.6205 -1.6772 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 19.3987 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2745 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2031 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3460 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4174 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\nA 2\nR\nA 8\nR\nA 10\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4792396198099049, 0.6061099689811179, 0.6678339169584793, 0.7747862126678854 ], "category_id": 1, "smiles": "*/C=C/N([H])C(C*)C(*)C([H])=O", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 2.5784 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7933 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4626 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3468 -6.3228 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2559 -8.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5285 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7185 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9002 -4.4331 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4626 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5784 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3468 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2309 -3.1732 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3468 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\n 7 8 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 2 0\nA 2\nR\nA 8\nR\nA 10\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4792396198099049, 0.6061099689811179, 0.6678339169584793, 0.7747862126678854 ], "category_id": 1, "smiles": "*/C=C/N([H])C(C*)C(*)C([H])=O", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 2.5784 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7933 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4626 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3468 -6.3228 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2559 -8.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5285 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7185 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9002 -4.4331 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4626 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5784 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3468 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2309 -3.1732 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3468 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\n 7 8 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 2 0\nA 2\nR\nA 8\nR\nA 10\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7478739369684843, 0.5853065655930833, 0.9109554777388694, 0.7567940800079636 ], "category_id": 1, "smiles": "*CC1C(*)C([H])(O)C(*)C=N1[H]", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4895 2.7762 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 12 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 12 1 0\n 12 13 1 0\nA 2\nR\nA 8\nR\nA 13\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7478739369684843, 0.5853065655930833, 0.9109554777388694, 0.7567940800079636 ], "category_id": 1, "smiles": "*CC1C(*)C([H])(O)C(*)C=N1[H]", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4895 2.7762 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 12 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 12 1 0\n 12 13 1 0\nA 2\nR\nA 8\nR\nA 13\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.14157078539269635, 0.8355096603951218, 0.3076538269134567, 0.9721374177814034 ], "category_id": 1, "smiles": "*CC1N=CC(*)([H])C([H])(O)C1*", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 3.3545 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9739 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7351 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1158 -8.0551 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4964 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4964 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8770 -5.3780 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8770 -2.6220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1158 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7090 -0.4173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4143 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7351 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3545 -2.6220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 12 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 12 1 0\n 12 13 1 0\nA 2\nR\nA 8\nR\nA 13\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.14157078539269635, 0.8355096603951218, 0.3076538269134567, 0.9721374177814034 ], "category_id": 1, "smiles": "*CC1N=CC(*)([H])C([H])(O)C1*", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 3.3545 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9739 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7351 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1158 -8.0551 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4964 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4964 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8770 -5.3780 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8770 -2.6220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1158 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7090 -0.4173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4143 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7351 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3545 -2.6220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 12 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 12 1 0\n 12 13 1 0\nA 2\nR\nA 8\nR\nA 13\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.38819409704852426, 0.8394454394144796, 0.551775887943972, 0.9755109426551388 ], "category_id": 1, "smiles": "*CC1([H])N=CC(*)=CC1(*)[H]", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 3.3117 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9615 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6619 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6619 -8.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0122 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3624 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3624 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7126 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0122 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6619 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6619 -0.0236 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3117 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 10 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\nA 2\nR\nA 8\nR\nA 12\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.38819409704852426, 0.8394454394144796, 0.551775887943972, 0.9755109426551388 ], "category_id": 1, "smiles": "*CC1([H])N=CC(*)=CC1(*)[H]", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 3.3117 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9615 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6619 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6619 -8.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0122 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3624 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3624 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7126 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0122 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6619 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6619 -0.0236 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3117 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 10 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\nA 2\nR\nA 8\nR\nA 12\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5817908954477239, 0.8613733510937595, 0.711855927963982, 0.8951085998311129 ], "category_id": 2, "text": [ "autoxidation" ] }, { "category": "[Txt]", "bbox": [ 0.6273136568284142, 0.9136629866366572, 0.6678339169584793, 0.9490849978108785 ], "category_id": 2, "text": [ "[0]" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7458729364682342, 0.857999826220024, 0.9069534767383692, 0.9608923348689522 ], "category_id": 1, "smiles": "*Cc1ncc(*)cc1*", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 4.3142 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2525 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3759 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3759 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3142 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4376 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4994 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4219 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4994 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4376 -7.6614 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 2 0\n 3 10 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\nA 2\nR\nA 5\nR\nA 8\nR\nM END\n" } ] } ], "Chugaev reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.15657828914457228, 0.1598573259232356, 0.39569784892446225, 0.452167864754295 ], "category_id": 1, "smiles": "*CCOC(=S)SC", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.2741 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5627 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9855 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8922 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6036 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 20.3150 -0.6535 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 24.2217 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6036 -7.2677 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 8 2 0\n 6 7 1 0\nA 2\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.45972986493246626, 0.17660428387709837, 0.48724362181090547, 0.26947377798488287 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5532766383191596, 0.004567352169235302, 0.7033516758379189, 0.5435149081390009 ], "category_id": 1, "smiles": "*C([H])COC(=S)SC", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 2.0703 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8014 -4.0394 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8014 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4746 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 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2.0703 -6.0079 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 9 2 0\n 7 8 1 0\nA 3\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.09004502251125562, 0.7231640934622562, 0.18509254627313657, 0.8693193628777859 ], "category_id": 1, "smiles": "*C=C", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 10.8661 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8346 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1102 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\nA 2\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.27613806903451726, 0.6181149935698442, 0.4227113556778389, 0.9393520961393939 ], "category_id": 1, "smiles": "[H]SC(=O)SC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 13.4231 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2761 -7.4252 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2027 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3831 -3.9606 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 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"[1*]C1(O)ONC(=O)C1[2*]", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 5.6488 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5865 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3387 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9527 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1457 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9938 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7522 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6139 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7796 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\nM ISO 2 2 2 8 1\nA 2\nR2\nA 8\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4122061030515258, 0.6283052637429827, 0.5012506253126563, 0.7142526818965038 ], "category_id": 2, "text": [ "Hzo" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5137568784392196, 0.5986682230003891, 0.6703351675837919, 0.8604620828932986 ], "category_id": 1, "smiles": "[1*]c1o[nH]c(=O)c1[2*]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 5.8769 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9179 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6755 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3546 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6083 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2762 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0374 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1455 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nM ISO 2 2 2 8 1\nA 2\nR2\nA 8\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5137568784392196, 0.5986682230003891, 0.6703351675837919, 0.8604620828932986 ], "category_id": 1, "smiles": "[1*]c1o[nH]c(=O)c1[2*]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 5.8769 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9179 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6755 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3546 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6083 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2762 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0374 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1455 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nM ISO 2 2 2 8 1\nA 2\nR2\nA 8\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7433716858429215, 0.6085472365812536, 0.9114557278639319, 0.8663894910418173 ], "category_id": 1, "smiles": "[1*]c1onc(O)c1[2*]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 5.9644 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9426 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7950 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4125 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7049 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3797 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0546 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1229 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nM ISO 2 2 2 8 1\nA 2\nR2\nA 8\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7433716858429215, 0.6085472365812536, 0.9114557278639319, 0.8663894910418173 ], "category_id": 1, "smiles": "[1*]c1onc(O)c1[2*]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 5.9644 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9426 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7950 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4125 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7049 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3797 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0546 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1229 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nM ISO 2 2 2 8 1\nA 2\nR2\nA 8\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5137568784392196, 0.5986682230003891, 0.6703351675837919, 0.8604620828932986 ], "category_id": 1, "smiles": "[1*]c1o[nH]c(=O)c1[2*]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 5.8769 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9179 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6755 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3546 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6083 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2762 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0374 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1455 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nM ISO 2 2 2 8 1\nA 2\nR2\nA 8\nR1\nM END\n" } ] } ], "Claisen rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.015507753876938469, 0.21764701795342117, 0.17358679339669836, 0.7594491690289589 ], "category_id": 1, "smiles": "*C(C=C)OC=C", "molfile": "\n RDKit 2D\n\n 7 6 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7 7 0 0 0 0 0 0 0 0999 V2000\n 7.5461 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3940 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2418 -1.3622 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3940 -6.6378 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 7.5461 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6983 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6983 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\nM CHG 1 4 1\nA 3\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5537768884442221, 0.16670835417708854, 0.7048524262131065, 0.740926018564838 ], "category_id": 1, "smiles": "*c1cccc[o+]1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 7.5461 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3940 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2418 -1.3622 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3940 -6.6378 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 7.5461 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6983 -6.4803 0.0000 C 0 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"text": [ "3" ] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5537768884442221, 0.16670835417708854, 0.7048524262131065, 0.740926018564838 ], "category_id": 1, "smiles": "*c1cccc[o+]1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 7.5461 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3940 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2418 -1.3622 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3940 -6.6378 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 7.5461 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6983 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6983 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\nM CHG 1 4 1\nA 3\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8419209604802401, 0.16670835417708854, 0.9859929964982491, 0.7108258990606415 ], "category_id": 1, "smiles": "*/C=C/CCC=O", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 4.8271 -2.3858 0.0000 C 0 0 0 0 0 0 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"\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 10.0921 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4961 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7840 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4961 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\nA 3\nPh\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3921960980490245, 0.12040844153805191, 0.5137568784392196, 0.1565309739994675 ], "category_id": 2, "text": [ "Zn(Hg); HCI" ] }, { "category": "[Txt]", "bbox": [ 0.4272136068034017, 0.17201205934007419, 0.4782391195597799, 0.20182748295902037 ], "category_id": 2, "text": [ "SET" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.512256128064032, 0.1003403679483766, 0.6498249124562281, 0.21788194183076062 ], "category_id": 1, "smiles": "CC(O)c1ccccc1.Cl", "molfile": "\n RDKit 2D\n\n 5 3 0 0 0 0 0 0 0 0999 V2000\n 7.6204 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0803 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4343 -7.5039 0.0000 R 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5367 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3729 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5367 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5367 -7.6614 0.0000 Zn 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\nA 3\nPh\nA 4\nOZnCl\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.25212606303151575, 0.3268229127461409, 0.3631815907953977, 0.42831002775678473 ], "category_id": 1, "smiles": "*C(C)([Zn])c1ccccc1", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 8.5028 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5367 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3729 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5367 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5367 -7.6614 0.0000 Zn 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\nA 3\nPh\nA 4\nOZnCl\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4767383691845923, 0.3268229127461409, 0.5857928964482241, 0.41225556888504444 ], "category_id": 1, "smiles": "*.CC(=[Zn])c1ccccc1", "molfile": "\n RDKit 2D\n\n 5 3 0 0 0 0 0 0 0 0999 V2000\n 14.6429 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3436 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0709 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0709 -0.4173 0.0000 Zn 0 0 0 0 0 2 0 0 0 0 0 0\n 12.6828 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\nA 1\n.\nA 2\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4767383691845923, 0.3268229127461409, 0.5857928964482241, 0.41225556888504444 ], "category_id": 1, "smiles": "*.CC(=[Zn])c1ccccc1", "molfile": "\n RDKit 2D\n\n 5 3 0 0 0 0 0 0 0 0999 V2000\n 14.6429 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3436 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0709 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0709 -0.4173 0.0000 Zn 0 0 0 0 0 2 0 0 0 0 0 0\n 12.6828 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\nA 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"products": [ { "category": "[Mol]", "bbox": [ 0.6028014007003502, 0.6456185960564117, 0.7128564282141071, 0.7465323375359219 ], "category_id": 1, "smiles": "*C([H])(C)c1ccccc1", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 8.5159 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5452 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3765 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5452 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5452 -7.6614 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\nA 3\nPh\nA 4\nOZnG\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6028014007003502, 0.6456185960564117, 0.7128564282141071, 0.7465323375359219 ], "category_id": 1, "smiles": "*C([H])(C)c1ccccc1", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 8.5159 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5452 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3765 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5452 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 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0.894447223611806, 0.7746276405614674 ], "category_id": 2, "text": [ "CIO" ] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.8349174587293647, 0.6031889547525267, 0.9444722361180591, 0.7230240227594451 ], "category_id": 1, "smiles": "[H]*C([H])(C)c1ccccc1", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 4.6341 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9033 -6.4803 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6341 -7.9764 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6341 -2.2283 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0688 -0.8110 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1167 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 6 1 0\n 4 5 1 0\nA 2\nPh\nA 4\nOZnG\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.8489244622311155, 0.7430920963491203, 0.894447223611806, 0.7746276405614674 ], "category_id": 2, "text": [ "CIO" ] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6028014007003502, 0.6456185960564117, 0.7128564282141071, 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1 2 1 0\n 2 3 1 0\n 2 4 1 0\nA 3\nPh\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6493246623311656, 0.8755413820409775, 0.7198599299649825, 0.9277183733741333 ], "category_id": 2, "text": [ "e ; H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7383691845922962, 0.889875720319317, 0.848424212106053, 0.9701480146780184 ], "category_id": 1, "smiles": "[H]C([H])(C)c1ccccc1", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 10.8301 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0956 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1121 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8549 -0.6535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2118 -0.6535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\nA 3\nPh\nM END\n" } ] } ], "Combes quinoline synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0639863944660673, 0.0240120060030015, 0.20465069965593424, 0.11905952976488245 ], "category_id": 1, "smiles": "Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 0.4449 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4449 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6708 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7854 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9000 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7854 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6708 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.09148467969115406, 0.11855927963981991, 0.26546421505756845, 0.2351175587793897 ], "category_id": 1, "smiles": "[1*]C(CC([2*])=O)=O[H]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 4 2 0\n 5 6 1 0\n 5 7 2 3\n 7 8 1 0\nM ISO 2 3 2 6 1\nA 3\nR2\nA 6\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3426709389587736, 0.04702351175587794, 0.5600131548724403, 0.20210105052526264 ], "category_id": 1, "smiles": "[1*]C(O)(CC([2*])=O)Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.3127 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3127 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2930 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1690 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0451 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0254 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0254 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0057 -6.5591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0254 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0057 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8818 -3.1732 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0057 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1690 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2930 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 2 0\n 13 14 2 0\nM ISO 2 7 1 11 2\nA 7\nR1\nA 11\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3426709389587736, 0.04702351175587794, 0.5600131548724403, 0.20210105052526264 ], "category_id": 1, "smiles": "[1*]C(O)(CC([2*])=O)Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.3127 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3127 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2930 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1690 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0451 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0254 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0254 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0057 -6.5591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0254 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0057 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8818 -3.1732 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0057 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1690 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2930 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 2 0\n 13 14 2 0\nM ISO 2 7 1 11 2\nA 7\nR1\nA 11\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5843385610330939, 0.08704352176088044, 0.6763520539016534, 0.12056028014007003 ], "category_id": 2, "text": [ "proton" ] }, { "category": "[Txt]", "bbox": [ 0.5816944951460663, 0.13706853426713356, 0.6795249329660866, 0.17058529264632316 ], "category_id": 2, "text": [ "transfer" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7001486468849016, 0.04402201100550275, 0.9164332364437572, 0.19559779889944973 ], "category_id": 1, "smiles": "[1*]C([OH2+])(CC([2*])=O)Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.3192 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3192 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2347 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1502 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9593 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9812 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9812 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8967 -6.7165 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 7.9812 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8967 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8122 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8967 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1502 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2347 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 2 0\n 13 14 2 0\nM CHG 1 8 1\nM ISO 2 7 1 11 2\nA 7\nR1\nA 11\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7001486468849016, 0.04402201100550275, 0.9164332364437572, 0.19559779889944973 ], "category_id": 1, "smiles": "[1*]C([OH2+])(CC([2*])=O)Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.3192 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3192 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2347 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1502 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9593 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9812 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9812 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8967 -6.7165 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 7.9812 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8967 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8122 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8967 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1502 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2347 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 2 0\n 13 14 2 0\nM CHG 1 8 1\nM ISO 2 7 1 11 2\nA 7\nR1\nA 11\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.0856677347396934, 0.3006503251625813, 0.30195232429854896, 0.45222611305652827 ], "category_id": 1, "smiles": "[1*]/C(CC([2*])=O)=N/c1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3192 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3192 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2347 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2566 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1721 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1940 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1095 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1940 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1095 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1314 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1095 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2566 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2347 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 2 0\nM ISO 2 7 1 10 2\nA 7\nR1\nA 10\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0856677347396934, 0.3006503251625813, 0.30195232429854896, 0.45222611305652827 ], "category_id": 1, "smiles": "[1*]/C(CC([2*])=O)=N/c1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3192 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3192 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2347 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2566 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1721 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1940 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1095 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1940 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1095 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1314 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1095 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2566 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2347 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 2 0\nM ISO 2 7 1 10 2\nA 7\nR1\nA 10\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.31517265373368686, 0.3391695847923962, 0.3786302350223486, 0.3806903451725863 ], "category_id": 2, "text": [ "H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3886776853930534, 0.3071535767883942, 0.6039046485970979, 0.44222111055527763 ], "category_id": 1, "smiles": "[1*]/C(CC([2*])=O)=N/c1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3570 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3570 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4987 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7594 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9011 -7.9764 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1619 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4226 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1619 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4226 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5643 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4226 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7594 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4987 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 2 0\nM ISO 2 7 1 10 2\nA 7\nR1\nA 10\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3886776853930534, 0.3071535767883942, 0.6039046485970979, 0.44222111055527763 ], "category_id": 1, "smiles": "[1*]/C(CC([2*])=O)=N/c1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3570 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3570 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4987 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7594 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9011 -7.9764 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1619 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4226 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1619 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4226 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5643 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4226 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7594 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4987 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 2 0\nM ISO 2 7 1 10 2\nA 7\nR1\nA 10\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6922164492238189, 0.2926463231615808, 0.8757146217835325, 0.4462231115557779 ], "category_id": 1, "smiles": "[1*]/C(=C/C([2*])=O)Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3564 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3564 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2278 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0991 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9704 -6.8740 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8418 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7131 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8418 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9704 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9704 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8318 -1.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0991 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2278 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 2 0\nM ISO 2 7 1 10 2\nA 7\nR1\nA 10\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6922164492238189, 0.2926463231615808, 0.8757146217835325, 0.4462231115557779 ], "category_id": 1, "smiles": "[1*]/C(=C/C([2*])=O)Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3564 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3564 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2278 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0991 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9704 -6.8740 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8418 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7131 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8418 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9704 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9704 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8318 -1.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0991 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2278 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 2 0\nM ISO 2 7 1 10 2\nA 7\nR1\nA 10\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8873485116864538, 0.32516258129064535, 0.9407586426044109, 0.3706853426713357 ], "category_id": 2, "text": [ "H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.1142236463195912, 0.5582791395697849, 0.2993082584115214, 0.71935967983992 ], "category_id": 1, "smiles": "[1*]/C(=C/C([2*])=[O+]/[H])Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.2560 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2560 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1333 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9253 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6319 -6.8740 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5092 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3012 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5092 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6319 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6319 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6693 -1.9921 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 3.6693 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9253 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1333 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 13 14 2 0\nM CHG 1 11 1\nM ISO 2 7 1 10 2\nA 7\nR1\nA 10\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1142236463195912, 0.5582791395697849, 0.2993082584115214, 0.71935967983992 ], "category_id": 1, "smiles": "[1*]/C(=C/C([2*])=[O+]/[H])Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.2560 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2560 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1333 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9253 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6319 -6.8740 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5092 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3012 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5092 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6319 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6319 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6693 -1.9921 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 3.6693 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9253 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1333 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 13 14 2 0\nM CHG 1 11 1\nM ISO 2 7 1 10 2\nA 7\nR1\nA 10\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2993082584115214, 0.599799899949975, 0.36223702652277767, 0.6418209104552276 ], "category_id": 2, "text": [ "H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3786302350223486, 0.5537768884442221, 0.5615995944046567, 0.7363681840920461 ], "category_id": 1, "smiles": "[2*]C1(O[H])C=C([7*])N([H])=C2C=CC=CC21[H]", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0941 2.1730 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7605 4.0753 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0905 3.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.1700 4.5883 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 16 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 1 0\n 5 7 1 0\n 5 16 1 0\n 7 8 1 0\n 7 9 1 0\n 7 11 1 0\n 9 10 1 0\n 11 12 2 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\nM ISO 2 8 2 13 7\nA 8\nR2\nA 13\nR7\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3786302350223486, 0.5537768884442221, 0.5615995944046567, 0.7363681840920461 ], "category_id": 1, "smiles": "[2*]C1(O[H])C=C([7*])N([H])=C2C=CC=CC21[H]", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0941 2.1730 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7605 4.0753 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0905 3.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.1700 4.5883 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 16 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 1 0\n 5 7 1 0\n 5 16 1 0\n 7 8 1 0\n 7 9 1 0\n 7 11 1 0\n 9 10 1 0\n 11 12 2 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\nM ISO 2 8 2 13 7\nA 8\nR2\nA 13\nR7\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6472673291443501, 0.5472736368184092, 0.8323519412362803, 0.7138569284642321 ], "category_id": 1, "smiles": "[2*]C1(O[H])C=C([Rf])Nc2ccccc21", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 0.3320 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3320 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1579 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9008 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7268 -7.0315 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5527 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4616 -7.0315 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 7.5527 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7268 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5527 -1.8346 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7268 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9008 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9008 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1579 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 13 1 0\n 11 12 1 0\n 13 14 2 0\nM ISO 1 10 2\nA 10\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6472673291443501, 0.5472736368184092, 0.8323519412362803, 0.7138569284642321 ], "category_id": 1, "smiles": "[2*]C1(O[H])C=C([Rf])Nc2ccccc21", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 0.3320 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3320 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1579 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9008 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7268 -7.0315 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5527 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4616 -7.0315 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 7.5527 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7268 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5527 -1.8346 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7268 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9008 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9008 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1579 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 13 1 0\n 11 12 1 0\n 13 14 2 0\nM ISO 1 10 2\nA 10\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8582637869291506, 0.5937968984492246, 0.9111451046697021, 0.64032016008004 ], "category_id": 2, "text": [ "H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.17345072218900884, 0.7913956978489245, 0.35853533428093903, 0.9649824912456229 ], "category_id": 1, "smiles": "[2*]C1([O-]([H])[H])=CC([Rf])=[NH+]C2=C1C=CC=C2", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0905 3.1111 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7605 4.0753 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n -0.6114 5.0395 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1700 4.5883 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 15 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\n 9 14 1 0\n 11 12 1 0\n 11 13 1 0\n 14 15 1 0\nM CHG 2 5 1 11 -1\nM ISO 1 10 2\nA 10\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.17345072218900884, 0.7913956978489245, 0.35853533428093903, 0.9649824912456229 ], "category_id": 1, "smiles": "[2*]C1([O-]([H])[H])=CC([Rf])=[NH+]C2=C1C=CC=C2", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0905 3.1111 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7605 4.0753 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n -0.6114 5.0395 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1700 4.5883 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 15 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\n 9 14 1 0\n 11 12 1 0\n 11 13 1 0\n 14 15 1 0\nM CHG 2 5 1 11 -1\nM ISO 1 10 2\nA 10\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.44420306902063245, 0.8034017008504252, 0.6261148020481295, 0.9709854927463731 ], "category_id": 1, "smiles": "[1*]C1=N([H])C2=C(C=CC=C2)C([2*])=C1", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 3.8971 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\nM ISO 2 8 1 11 2\nA 8\nR1\nA 11\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.44420306902063245, 0.8034017008504252, 0.6261148020481295, 0.9709854927463731 ], "category_id": 1, "smiles": "[1*]C1=N([H])C2=C(C=CC=C2)C([2*])=C1", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 3.8971 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\nM ISO 2 8 1 11 2\nA 8\nR1\nA 11\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6208266702740743, 0.8319159579789895, 0.6837554383853306, 0.8734367183591796 ], "category_id": 2, "text": [ "~H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.69327407557863, 0.8059029514757379, 0.8762434349609382, 0.9419709854927464 ], "category_id": 1, "smiles": "[2*]c1cc([4*])nc2ccccc12", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 0.4020 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4020 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6128 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7231 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9339 -8.0551 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1447 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3555 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1447 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9339 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9339 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7231 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6128 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 12 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 11 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\n 11 12 2 0\nM ISO 2 7 4 10 2\nA 7\nR4\nA 10\nR2\nM END\n" } ] } ], "Conrad\u2013Limpach reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.10955477738869435, 0.049816797406173736, 0.2466233116558279, 0.1900154986778341 ], "category_id": 1, "smiles": 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1 0\n 3 5 2 0\nA 2\nCO2Et\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.38819409704852426, 0.09678692067485184, 0.4737368684342171, 0.1401987012716604 ], "category_id": 2, "text": [ "proton" ] }, { "category": "[Txt]", "bbox": [ 0.38319159579789897, 0.16937711118099072, 0.4792396198099049, 0.2142122288465471 ], "category_id": 2, "text": [ "transfer" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5147573786893447, 0.07899520731550408, 0.7408704352176088, 0.25477733530586 ], "category_id": 1, "smiles": "CCOC(=O)CC(C)(O)Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 13.6823 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9459 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9459 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6823 -6.1654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9459 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0654 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4729 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8805 -6.1654 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"bbox": [ 0.5757878939469735, 0.4995913111304852, 0.7723861930965483, 0.5465614343991633 ], "category_id": 2, "text": [ "electrocyclization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7983991995997999, 0.34800591330884223, 0.9714857428714357, 0.5657764848272588 ], "category_id": 1, "smiles": "[H]OC1(OCC)C=C(C)N=C2C=CC=CC21[H]", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 6.3924 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3457 -2.2283 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3924 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3504 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3504 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3504 -2.2283 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3504 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3084 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2664 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2664 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3084 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3924 -8.1339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 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0 0 0 0\n 0.2664 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2664 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3084 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3924 -8.1339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3457 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3877 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3457 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 1 0\n 1 15 1 0\n 3 4 1 0\n 5 6 1 0\n 5 7 1 0\n 5 11 1 0\n 7 8 1 0\n 7 12 2 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 12 13 1 0\n 13 14 1 0\n 13 15 2 0\nA 2\nOEt\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.0735367683841921, 0.7885287360862929, 0.17208604302151076, 0.8440388817674579 ], "category_id": 2, "text": [ "HOEt" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.19809904952476237, 0.7180735511832759, 0.36418209104552274, 0.9337091170985706 ], "category_id": 1, "smiles": "[H]C12C=CC=CC1=NC(C)=CC2=O", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 10.9278 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6046 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4534 -9.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4744 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4744 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4744 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4093 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3442 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3442 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4093 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4534 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4534 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6046 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 13 2 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 5 7 1 0\n 5 11 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 2 0\n 11 13 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.19809904952476237, 0.7180735511832759, 0.36418209104552274, 0.9337091170985706 ], "category_id": 1, "smiles": "[H]C12C=CC=CC1=NC(C)=CC2=O", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 10.9278 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6046 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4534 -9.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4744 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4744 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4744 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4093 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3442 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3442 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4093 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4534 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4534 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6046 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 13 2 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 5 7 1 0\n 5 11 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 2 0\n 11 13 1 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4512256128064032, 0.732306921870754, 0.6143071535767884, 0.9543475045954141 ], "category_id": 1, "smiles": "Cc1cc(=O)c2ccccc2[nH]1", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 10.2031 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1461 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1713 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1965 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3039 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3291 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3291 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3039 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1965 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1713 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1713 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1461 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 10 12 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4512256128064032, 0.732306921870754, 0.6143071535767884, 0.9543475045954141 ], "category_id": 1, "smiles": "Cc1cc(=O)c2ccccc2[nH]1", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 10.2031 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1461 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1713 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1965 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3039 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3291 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3291 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3039 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1965 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1713 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1713 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1461 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 10 12 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6518259129564783, 0.7849703934144234, 0.7388694347173587, 0.8340755222862233 ], "category_id": 2, "text": [ "proton" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7823911955977989, 0.7266135735957626, 0.9469734867433717, 0.9208990834798403 ], "category_id": 1, "smiles": "Cc1cc(O)c2ccccc2n1", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 11.8400 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4529 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4529 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1613 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1613 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8697 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6735 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3819 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3819 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6735 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8697 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1613 -8.0551 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 12 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 6 11 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7823911955977989, 0.7266135735957626, 0.9469734867433717, 0.9208990834798403 ], "category_id": 1, "smiles": "Cc1cc(O)c2ccccc2n1", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 11.8400 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4529 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4529 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1613 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1613 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8697 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6735 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3819 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3819 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6735 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8697 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1613 -8.0551 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 12 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 6 11 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.647823911955978, 0.8604072580580578, 0.7443721860930466, 0.9073773813267361 ], "category_id": 2, "text": [ "transfer" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4512256128064032, 0.732306921870754, 0.6143071535767884, 0.9543475045954141 ], "category_id": 1, "smiles": "Cc1cc(=O)c2ccccc2[nH]1", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 10.2031 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1461 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1713 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1965 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3039 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3291 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3291 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3039 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1965 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1713 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1713 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1461 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 10 12 1 0\nM END\n" } ] } ], "Cope elimination reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.015507753876938469, 0.025647439104167464, 0.28714357178589295, 0.9473522819101858 ], "category_id": 1, "smiles": "*C([1*])([H])C([2*])([3*])N(C)(C)[O-]", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3481 0.2010 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7990 -1.8481 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5490 -3.1471 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 4.0981 -1.0981 0.0000 C 0 0 0 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0 0 0 0 0 0\n 9.4230 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4230 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 3\n 4 5 1 0\n 4 6 1 0\nM ISO 2 5 2 6 3\nA 2\nR\nA 3\nR\nA 5\nR2\nA 6\nR3\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.8414207103551776, 0.2837247950898526, 0.9889944972486243, 0.7549964886289298 ], "category_id": 1, "smiles": "CN(C)O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 0.6368 -8.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9350 -5.8504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9350 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3923 -8.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\nM END\n" } ] } ], "Cope rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.015507753876938469, 0.21858854738572606, 0.16808404202101052, 0.8937227950074622 ], "category_id": 1, "smiles": "*C(C=C)CC=C", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1484 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3955 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5439 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1484 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3955 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5439 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 5 1 0\n 3 4 2 0\n 5 6 1 0\n 6 7 2 0\nA 1\n*\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.21460730365182593, 0.25179187103925404, 0.5147573786893447, 0.4897490238895381 ], "category_id": 2, "text": [ "[3,3]-sigmatropic" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5867933966983492, 0.24072409648807805, 0.7383691845922962, 0.9047905695586381 ], "category_id": 1, "smiles": "*c1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 8.4698 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8826 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3950 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8826 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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"category": "[Mol]", "bbox": [ 0.8379189594797398, 0.19368605464558003, 0.9859929964982491, 0.8660533586295222 ], "category_id": 1, "smiles": "*/C=C/CCC=C", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 5.0442 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7131 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3752 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6111 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6111 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3752 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0442 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 2 0\nA 2\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5867933966983492, 0.24072409648807805, 0.7383691845922962, 0.9047905695586381 ], "category_id": 1, "smiles": "*c1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 8.4698 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8826 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3950 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8826 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4698 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0570 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0570 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\nA 3\nR\nM END\n" } ] } ], "Corey\u2013Bakshi\u2013Shibata (CBS) reagent.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2786393196598299, 0.10825217803707049, 0.3966983491745873, 0.24248487880303787 ], "category_id": 1, "smiles": "CC(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 10.4416 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8740 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3920 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9100 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3423 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3423 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9100 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3920 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0 0 0 0\n 1.6713 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 9 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 9 1 0\n 7 12 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 7 8 1 6\nA 2\nMe\nA 5\nPh\nA 6\nPh\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.4147073536768384, 0.20969993345466795, 0.6208104052026013, 0.24867071754801331 ], "category_id": 2, "text": [ "BH3, THF , rt, 97% ee" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6388194097048524, 0.10144775541759747, 0.7548774387193596, 0.2375362078070575 ], "category_id": 1, "smiles": "C[C@@H](O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 10.2198 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7272 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7272 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2345 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8250 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4154 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4154 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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-1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -0.4961 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7819 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7819 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8055 -0.9685 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0828 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 1 0\n 3 4 1 0\n 3 5 1 0\n 3 8 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 1 0\n 8 9 1 6\nM CHG 1 3 1\nA 2\nR\nA 4\nH3B-\nA 11\nPh\nA 12\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7258629314657329, 0.31176627274676294, 0.8539269634817409, 0.48496975760607575 ], "category_id": 1, "smiles": "*B1OC(c2ccccc2)(c2ccccc2)[C@]2([H])CCC[N+]12*", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 5.7819 -5.6142 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5046 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -4.9055 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 3.1078 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5900 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2891 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5900 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -0.4961 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7819 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7819 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8055 -0.9685 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0828 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 1 0\n 3 4 1 0\n 3 5 1 0\n 3 8 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 1 0\n 8 9 1 6\nM CHG 1 3 1\nA 2\nR\nA 4\nH3B-\nA 11\nPh\nA 12\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.27763881940970486, 0.3241379502367139, 0.407703851925963, 0.4930113479745439 ], "category_id": 1, "smiles": "*B1OC(c2ccccc2)(c2ccccc2)[C@]2([H])CCCN12", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 6.0186 -5.6142 0.0000 B 0 0 0 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0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5328 4.0667 0.0000 B 0 0 0 0 0 5 0 0 0 0 0 0\n 0.8938 4.5302 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9963 5.4933 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.9593 3.6032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.2958 4.2842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.6324 4.9651 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6149 5.6207 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.9768 2.9476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 7 1 0\n 1 11 1 0\n 2 3 1 6\n 2 8 1 0\n 3 4 1 0\n 3 7 1 1\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\n 11 12 1 1\n 12 13 1 1\n 12 14 1 0\n 12 15 1 0\nM CHG 1 8 -1\nA 9\nR\nA 10\nPh\nA 14\nPh\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.4102051025512756, 0.7466307365185375, 0.45822911455727866, 0.7843643528628877 ], "category_id": 2, "text": [ "BH3" ] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4842421210605303, 0.5579626547967862, 0.6693346673336669, 0.7924059432313558 ], "category_id": 1, "smiles": "*[B-]12OC(c3ccccc3)(c3ccccc3)C3([H])CCCN13B([H])[H]B([H])([H])O2C([H])(C)c1ccccc1", "molfile": "\n RDKit 2D\n\n 23 25 0 0 0 0 0 0 0 0999 V2000\n -1.3505 1.0837 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7607 -1.8338 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.9140 1.9635 0.0000 B 0 0 0 0 0 4 0 0 0 0 0 0\n -2.5000 3.3443 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 3.1771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 2.7135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7062 4.1807 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8941 2.7397 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8667 1.4997 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.6949 1.5577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.2874 3.0203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1904 4.0433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -5.1691 4.2338 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -5.5010 2.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8768 1.7525 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2594 1.2752 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -5.0578 -0.6426 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2215 0.8505 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 23 1 0\n 3 4 1 0\n 3 10 1 0\n 3 14 1 0\n 4 5 1 1\n 4 6 1 0\n 4 15 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 10 11 1 6\n 10 12 1 0\n 12 13 1 0\n 13 14 1 0\n 15 16 1 6\n 15 20 1 0\n 16 17 1 0\n 16 18 1 1\n 16 19 1 0\n 20 21 1 0\n 20 22 1 0\n 20 23 1 0\nM CHG 1 4 -1\nA 5\nR\nA 8\nPh\nA 9\nPh\nA 17\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4842421210605303, 0.5579626547967862, 0.6693346673336669, 0.7924059432313558 ], "category_id": 1, "smiles": "*[B-]12OC(c3ccccc3)(c3ccccc3)C3([H])CCCN13B([H])[H]B([H])([H])O2C([H])(C)c1ccccc1", "molfile": "\n RDKit 2D\n\n 23 25 0 0 0 0 0 0 0 0999 V2000\n -1.3505 1.0837 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7607 -1.8338 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.9140 1.9635 0.0000 B 0 0 0 0 0 4 0 0 0 0 0 0\n -2.5000 3.3443 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 3.1771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 2.7135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7062 4.1807 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8941 2.7397 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8667 1.4997 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.6949 1.5577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.2874 3.0203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1904 4.0433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -5.1691 4.2338 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -5.5010 2.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8768 1.7525 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2594 1.2752 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -5.0578 -0.6426 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2215 0.8505 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 23 1 0\n 3 4 1 0\n 3 10 1 0\n 3 14 1 0\n 4 5 1 1\n 4 6 1 0\n 4 15 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 10 11 1 6\n 10 12 1 0\n 12 13 1 0\n 13 14 1 0\n 15 16 1 6\n 15 20 1 0\n 16 17 1 0\n 16 18 1 1\n 16 19 1 0\n 20 21 1 0\n 20 22 1 0\n 20 23 1 0\nM CHG 1 4 -1\nA 5\nR\nA 8\nPh\nA 9\nPh\nA 17\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7258629314657329, 0.31176627274676294, 0.8539269634817409, 0.48496975760607575 ], "category_id": 1, "smiles": "*B1OC(c2ccccc2)(c2ccccc2)[C@]2([H])CCC[N+]12*", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 5.7819 -5.6142 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5046 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -4.9055 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 3.1078 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5900 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2891 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5900 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -0.4961 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7819 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7819 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8055 -0.9685 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0828 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 1 0\n 3 4 1 0\n 3 5 1 0\n 3 8 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 1 0\n 8 9 1 6\nM CHG 1 3 1\nA 2\nR\nA 4\nH3B-\nA 11\nPh\nA 12\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4847423711855928, 0.5579626547967862, 0.6693346673336669, 0.7924059432313558 ], "category_id": 1, "smiles": "*[B-]12OC(c3ccccc3)(c3ccccc3)C3([H])CCCN13B([H])[H]B([H])([H])O2C([H])(C)c1ccccc1", "molfile": "\n RDKit 2D\n\n 23 25 0 0 0 0 0 0 0 0999 V2000\n -1.3505 1.0837 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7607 -1.8338 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.9140 1.9635 0.0000 B 0 0 0 0 0 4 0 0 0 0 0 0\n -2.5000 3.3443 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 3.1771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 2.7135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7062 4.1807 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8941 2.7397 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8667 1.4997 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.6949 1.5577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.2874 3.0203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1904 4.0433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -5.1691 4.2338 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -5.5010 2.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8768 1.7525 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2594 1.2752 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -5.0578 -0.6426 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2215 0.8505 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 23 1 0\n 3 4 1 0\n 3 10 1 0\n 3 14 1 0\n 4 5 1 1\n 4 6 1 0\n 4 15 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 10 11 1 6\n 10 12 1 0\n 12 13 1 0\n 13 14 1 0\n 15 16 1 6\n 15 20 1 0\n 16 17 1 0\n 16 18 1 1\n 16 19 1 0\n 20 21 1 0\n 20 22 1 0\n 20 23 1 0\nM CHG 1 4 -1\nA 5\nR\nA 8\nPh\nA 9\nPh\nA 17\nPh\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.8244122061030515, 0.549921064428318, 0.9714857428714357, 0.692813939437251 ], "category_id": 1, "smiles": "CC(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 9.7371 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5287 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3203 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3203 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0115 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8031 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8031 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0115 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5287 -0.4961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 2 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7153576788394197, 0.8109634594662822, 0.9154577288644322, 0.9705580990866491 ], "category_id": 1, "smiles": "*B123OC([CH]CCC)(c4ccccc4)CCCN1BN2BN3=C(C)c1ccccc1", "molfile": "\n RDKit 2D\n\n 20 22 0 0 0 0 0 0 0 0999 V2000\n 1.0777 1.3515 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3946 0.6200 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4115 2.8138 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8739 2.4801 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5401 1.0177 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3382 -0.2524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8371 -0.1963 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8042 -1.6541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7286 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0777 -1.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4885 -1.8610 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0777 -2.8515 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 2.3768 -3.6015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3768 -5.1015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6758 -5.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3846 -1.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5574 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5574 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3846 1.6852 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0509 3.1476 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 1 0\n 1 9 1 0\n 1 19 1 0\n 3 4 1 0\n 3 20 1 0\n 4 5 1 0\n 5 6 2 3\n 6 7 1 0\n 6 8 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 6\n 10 16 1 0\n 12 13 1 0\n 13 14 1 0\n 14 15 1 0\n 16 17 1 0\n 17 18 1 0\n 18 19 1 0\n 19 20 1 0\nA 2\nR\nA 7\nPh\nA 11\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7153576788394197, 0.8109634594662822, 0.9154577288644322, 0.9705580990866491 ], "category_id": 1, "smiles": "*B123OC([CH]CCC)(c4ccccc4)CCCN1BN2BN3=C(C)c1ccccc1", "molfile": "\n RDKit 2D\n\n 20 22 0 0 0 0 0 0 0 0999 V2000\n 1.0777 1.3515 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3946 0.6200 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4115 2.8138 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8739 2.4801 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5401 1.0177 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3382 -0.2524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8371 -0.1963 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8042 -1.6541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7286 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0777 -1.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4885 -1.8610 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0777 -2.8515 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 2.3768 -3.6015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3768 -5.1015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6758 -5.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3846 -1.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5574 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5574 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3846 1.6852 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0509 3.1476 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 1 0\n 1 9 1 0\n 1 19 1 0\n 3 4 1 0\n 3 20 1 0\n 4 5 1 0\n 5 6 2 3\n 6 7 1 0\n 6 8 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 6\n 10 16 1 0\n 12 13 1 0\n 13 14 1 0\n 14 15 1 0\n 16 17 1 0\n 17 18 1 0\n 18 19 1 0\n 19 20 1 0\nA 2\nR\nA 7\nPh\nA 11\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7258629314657329, 0.31176627274676294, 0.8539269634817409, 0.48496975760607575 ], "category_id": 1, "smiles": "*B1OC(c2ccccc2)(c2ccccc2)[C@]2([H])CCC[N+]12*", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 5.7819 -5.6142 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5046 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -4.9055 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 3.1078 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5900 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2891 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5900 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7582 -0.4961 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7819 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7819 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8055 -0.9685 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0828 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 1 0\n 3 4 1 0\n 3 5 1 0\n 3 8 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 1 0\n 8 9 1 6\nM CHG 1 3 1\nA 2\nR\nA 4\nH3B-\nA 11\nPh\nA 12\nPh\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7153576788394197, 0.8109634594662822, 0.9154577288644322, 0.9705580990866491 ], "category_id": 1, "smiles": "*B123OC([CH]CCC)(c4ccccc4)CCCN1BN2BN3=C(C)c1ccccc1", "molfile": "\n RDKit 2D\n\n 20 22 0 0 0 0 0 0 0 0999 V2000\n 1.0777 1.3515 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3946 0.6200 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4115 2.8138 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8739 2.4801 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5401 1.0177 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3382 -0.2524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8371 -0.1963 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8042 -1.6541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7286 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0777 -1.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4885 -1.8610 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0777 -2.8515 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 2.3768 -3.6015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3768 -5.1015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6758 -5.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3846 -1.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5574 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5574 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3846 1.6852 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0509 3.1476 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 1 0\n 1 9 1 0\n 1 19 1 0\n 3 4 1 0\n 3 20 1 0\n 4 5 1 0\n 5 6 2 3\n 6 7 1 0\n 6 8 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 6\n 10 16 1 0\n 12 13 1 0\n 13 14 1 0\n 14 15 1 0\n 16 17 1 0\n 17 18 1 0\n 18 19 1 0\n 19 20 1 0\nA 2\nR\nA 7\nPh\nA 11\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.2926463231615808, 0.8023032852233167, 0.4932466233116558, 0.9662280119651662 ], "category_id": 1, "smiles": "*[B-]12(c3ccccc3)N3B(O1C([H])(C)c1ccccc1)N21CCCC31", "molfile": "\n RDKit 2D\n\n 15 18 0 0 0 0 0 0 0 0999 V2000\n -1.4958 2.1766 0.0000 B 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0692 2.6401 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5328 4.0667 0.0000 B 0 0 0 0 0 5 0 0 0 0 0 0\n 0.8938 4.5302 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 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0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3076 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3076 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2146 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8297 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4592 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6594 -0.8110 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 1 0\n 3 4 1 0\n 3 8 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 2 0\nM RAD 1 2 2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5757878939469735, 0.06146464536616134, 0.6998499249624812, 0.42793309698327425 ], "category_id": 1, "smiles": "C[Si](C)N1C(=O)CCC1=O.Cl", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 6.4592 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4134 -4.5906 0.0000 Si 0 0 0 0 0 3 0 0 0 0 0 0\n 3.3834 -4.5906 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2146 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8297 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3076 -5.6142 0.0000 C 0 0 0 0 0 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"category": "[Mol]", "bbox": [ 0.863431715857929, 0.07886029971507494, 0.9459729864932466, 0.4024194706048677 ], "category_id": 1, "smiles": "O=C1CCC(=O)N1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 0.3274 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5720 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3203 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9750 -3.9606 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5720 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3203 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3274 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 7 1 0\n 2 3 2 0\n 2 4 1 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.15057528764382191, 0.5149113687278423, 0.20060030015007504, 0.6169658742414685 ], "category_id": 1, "smiles": "[Cl].[Si]", "molfile": "\n RDKit 2D\n\n 2 0 0 0 0 0 0 0 0 0999 V2000\n 3.1560 -5.9291 0.0000 Cl 0 0 0 0 0 15 0 0 0 0 0 0\n 8.7465 -1.5984 0.0000 Si 0 0 0 0 0 15 0 0 0 0 0 0\nM END\n" } 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1 0\n 6 9 1 0\nM CHG 1 5 -1\nM ISO 2 3 1 4 2\nA 3\nR1\nA 4\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Txt]", "bbox": [ 0.7248624312156078, 0.7352563238140809, 0.8309154577288644, 0.832671988167997 ], "category_id": 2, "text": [ "(CHa)zst" ] }, { "category": "[Mol]", "bbox": [ 0.8849424712356178, 0.6911873327968332, 0.9794897448724362, 0.8744215586053897 ], "category_id": 1, "smiles": "[1*]C([2*])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.7037 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4961 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2569 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7037 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" } ] } ], "Corey\u2013Nicolaou macrolactonization.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.13956978489244623, 0.04600966536626179, 0.3626813406703352, 0.23679641108502736 ], "category_id": 1, "smiles": 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"conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.32216108054027015, 0.4024312064035698, 0.5297648824412207, 0.6337064576446456 ], "category_id": 1, "smiles": "OCCCC([Os])(OP(c1ccccc1)(c1ccccc1)c1ccccc1)Sc1ccccn1", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 0.2600 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2600 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9069 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4671 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1140 -3.0945 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7609 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2344 -5.1417 0.0000 Os 0 0 0 0 0 1 0 0 0 0 0 0\n 7.0209 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3211 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9406 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2472 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2007 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0209 -8.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4671 -0.3386 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9069 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 10 1 0\n 8 9 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 14 15 2 0\nA 9\nPPh3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.32216108054027015, 0.4024312064035698, 0.5297648824412207, 0.6337064576446456 ], "category_id": 1, "smiles": "OCCCC([Os])(OP(c1ccccc1)(c1ccccc1)c1ccccc1)Sc1ccccn1", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 0.2600 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2600 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9069 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4671 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1140 -3.0945 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7609 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2344 -5.1417 0.0000 Os 0 0 0 0 0 1 0 0 0 0 0 0\n 7.0209 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3211 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9406 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2472 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2007 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0209 -8.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4671 -0.3386 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9069 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 10 1 0\n 8 9 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 14 15 2 0\nA 9\nPPh3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6603301650825413, 0.5024255457995788, 0.7648824412206103, 0.5557967576244424 ], "category_id": 1, "smiles": "*=O", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.0280 -3.1732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1122 -3.1732 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\nA 2\nPh3\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.8179089544772387, 0.4245158457793754, 0.9979989994997499, 0.6018064229907042 ], "category_id": 1, "smiles": "CCC1(SC2=CC=CC=N2)=O[H]O=1", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n -1.8481 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5490 -3.1471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -4.6471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -5.9462 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n 0.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 11 2 0\n 3 13 2 0\n 4 5 1 0\n 5 6 1 0\n 5 10 2 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 11 12 1 1\n 12 13 1 6\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0, 0.353967692217774, 0.13706853426713356, 0.4637774268919188 ], "category_id": 1, "smiles": "[H]Sc1ccccn1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 14.6917 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3473 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0028 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5389 -7.4252 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1944 -5.5354 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0028 -1.5197 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3473 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6917 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 8 1 0\n 2 3 1 0\n 3 4 1 0\n 3 6 2 0\n 4 5 1 0\n 6 7 1 0\n 7 8 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.07603801900950476, 0.4668447379163363, 0.21460730365182593, 0.7011873001818296 ], "category_id": 1, "smiles": "O=C(CCCO)OP(c1ccccc1)(c1ccccc1)c1ccccc1", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 0.8564 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7699 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4828 -8.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5416 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1402 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4257 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7388 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6247 -5.2205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 4 1 0\n 2 3 1 0\n 4 5 1 0\n 5 6 1 0\n 5 8 2 0\n 6 7 1 0\nA 7\nPPh3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3231615807903952, 0.7238854017625188, 0.46973486743371684, 0.9171259963008184 ], "category_id": 1, "smiles": "[H]1[N+]=C2(=CC=C2)SC2(CCCO2)O1", "molfile": "\n RDKit 2D\n\n 13 15 0 0 0 0 0 0 0 0999 V2000\n -1.5653 5.3313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0674 5.2528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.1459 3.7548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.6094 2.3282 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8615 1.5254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3250 2.9520 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n 1.3213 4.0667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.6438 3.8333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 2 0\n 2 3 2 0\n 3 4 1 0\n 3 12 2 0\n 3 13 1 0\n 4 5 1 0\n 5 6 1 0\n 5 9 1 0\n 5 10 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 10 11 1 0\n 11 12 1 0\nM CHG 1 12 1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2991495747873937, 0.7238854017625188, 0.46973486743371684, 0.9171259963008184 ], "category_id": 1, "smiles": "[H]1OC2(CCCO2)SC2=[N+]1C=CC=C2", "molfile": "\n RDKit 2D\n\n 14 16 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8615 1.5254 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3250 2.9520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7923 3.2638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2558 4.6904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2521 5.8051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7849 5.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3213 4.0667 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n -0.1459 3.7548 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n -0.6094 2.3282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 2 11 1 0\n 2 12 1 0\n 3 4 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 12 13 1 0\n 13 14 1 0\nM CHG 1 9 1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5707853926963482, 0.7441296545236741, 0.6678339169584793, 0.8809317262126923 ], "category_id": 1, "smiles": "O=C1CCCCO1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 1.1736 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6923 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9368 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5936 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5936 -5.7717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9368 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6923 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 7 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7113556778389195, 0.7545585120066933, 0.8204102051025512, 0.8919740459005953 ], "category_id": 1, "smiles": "S=c1cccc[nH]1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 3.2171 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4596 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4596 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2171 -6.0079 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9746 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7321 -6.0079 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9746 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 7 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\nM END\n" } ] } ], "Corey\u2013Seebach reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.011005502751375688, 0.23387490846872713, 0.2621310655327664, 0.8562527640631911 ], "category_id": 1, "smiles": "[CH2]CCC.[H]C1([H])SCCCS1", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 0.3684 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7192 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2979 -7.8976 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6487 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9818 -7.0315 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9818 -4.1969 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2979 -3.2520 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7192 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7885 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 8 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 8 1 0\nA 9\nBu\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3356678339169585, 0.48321262080315525, 0.46773386693346675, 0.9065068766267192 ], "category_id": 1, "smiles": "C1CSCSC1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 1.1438 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1455 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9581 -7.3465 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8645 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9581 -0.3386 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1455 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.38319159579789897, 0.17588939397234848, 0.6078039019509754, 0.39236864809216204 ], "category_id": 1, "smiles": "ClCCCCI", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 18.7429 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0717 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4944 -5.6929 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 25.7317 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 32.4029 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 39.7095 -1.6772 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 4 1 0\n 2 3 1 0\n 4 5 1 0\n 5 6 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.3356678339169585, 0.48321262080315525, 0.46773386693346675, 0.9065068766267192 ], "category_id": 1, "smiles": "C1CSCSC1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 1.1438 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1455 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9581 -7.3465 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8645 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9581 -0.3386 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1455 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6943471735867934, 0.2937932734483184, 0.9874937468734367, 0.8794469698617425 ], "category_id": 1, "smiles": "ClCCCCC1SCCCS1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 0.4560 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8240 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7120 -5.1417 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2319 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1199 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6399 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5279 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.0478 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.0878 -7.7402 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7120 -0.0236 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8240 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 10 11 1 0\nM END\n" } ] } ], "Corey\u2013Winter olefin synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1410812379248261, 0.04202101050525263, 0.27952050510199633, 0.1345672836418209 ], "category_id": 1, "smiles": "S=C(n1ccnc1)n1ccnc1", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 0.7777 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4442 -7.8189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8884 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8884 -4.4331 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 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N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2891 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7615 -3.8031 0.0000 S 0 0 0 0 0 2 0 0 0 0 0 0\n 7.3619 -3.8031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2891 -4.9843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8807 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5364 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8807 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5364 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2891 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3774 -2.2283 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8652 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1456 0.1339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4899 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9778 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3443 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 19 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 19 1 0\n 5 6 1 0\n 5 8 1 0\n 5 14 1 0\n 6 7 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 1 0\n 14 15 1 0\n 14 18 1 0\n 15 16 2 0\n 16 17 1 0\n 17 18 2 0\nM CHG 1 6 -1\nM RAD 1 6 2\nA 10\nR\nA 12\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3471549562419879, 0.05902951475737869, 0.4813670702229086, 0.21660830415207605 ], "category_id": 1, "smiles": "*C(O)C(*)OC([S-][H])(n1ccnc1)n1ccnc1", "molfile": "\n RDKit 2D\n\n 19 20 0 0 0 0 0 0 0 0999 V2000\n 0.4481 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3443 -0.4961 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8807 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8807 -2.6220 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2891 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7615 -3.8031 0.0000 S 0 0 0 0 0 2 0 0 0 0 0 0\n 7.3619 -3.8031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2891 -4.9843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8807 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5364 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8807 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5364 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2891 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3774 -2.2283 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8652 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1456 0.1339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4899 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9778 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3443 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 19 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 19 1 0\n 5 6 1 0\n 5 8 1 0\n 5 14 1 0\n 6 7 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 1 0\n 14 15 1 0\n 14 18 1 0\n 15 16 2 0\n 16 17 1 0\n 17 18 2 0\nM CHG 1 6 -1\nM RAD 1 6 2\nA 10\nR\nA 12\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.548473127213369, 0.1055527763881941, 0.6847988177924145, 0.18859429714857429 ], "category_id": 1, "smiles": "*C(=S)OC(*)C(*)O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 4.4482 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8534 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1666 -6.9528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4482 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8534 -1.6772 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1666 -2.3071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1320 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8619 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4912 -0.5748 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\nA 2\nR\nA 5\nR\nA 8\nImd\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.548473127213369, 0.1055527763881941, 0.6847988177924145, 0.18859429714857429 ], "category_id": 1, "smiles": "*C(=S)OC(*)C(*)O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 4.4482 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8534 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1666 -6.9528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4482 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8534 -1.6772 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1666 -2.3071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1320 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8619 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4912 -0.5748 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\nA 2\nR\nA 5\nR\nA 8\nImd\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7397518093436577, 0.10005002501250625, 0.878719470670359, 0.176088044022011 ], "category_id": 1, "smiles": "*C1OC(*)([S-][H])OC1*", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 4.7769 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0472 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9160 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0997 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3753 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3753 -2.4646 0.0000 S 0 0 0 0 0 2 0 0 0 0 0 0\n 16.2415 -1.5197 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9160 -6.4803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7769 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0472 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 9 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 8 1 0\n 6 7 1 0\n 8 9 1 0\n 9 10 1 0\nM CHG 1 6 -1\nM RAD 1 6 2\nA 2\nR\nA 5\nImd\nA 10\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7397518093436577, 0.10005002501250625, 0.878719470670359, 0.176088044022011 ], "category_id": 1, "smiles": "*C1OC(*)([S-][H])OC1*", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 4.7769 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0472 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9160 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0997 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3753 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3753 -2.4646 0.0000 S 0 0 0 0 0 2 0 0 0 0 0 0\n 16.2415 -1.5197 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9160 -6.4803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7769 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0472 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 9 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 8 1 0\n 6 7 1 0\n 8 9 1 0\n 9 10 1 0\nM CHG 1 6 -1\nM RAD 1 6 2\nA 2\nR\nA 5\nImd\nA 10\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.2287946667470027, 0.28414207103551775, 0.34821174454105025, 0.3586793396698349 ], "category_id": 1, "smiles": "*C1OC(=[Si])OC1[Rf]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 4.8699 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0192 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8393 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7398 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9468 -3.8819 0.0000 Si 0 0 0 0 0 2 0 0 0 0 0 0\n 7.8393 -6.6378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8699 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0192 -7.2677 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\nM RAD 1 5 3\nA 2\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2287946667470027, 0.28414207103551775, 0.34821174454105025, 0.3586793396698349 ], "category_id": 1, "smiles": "*C1OC(=[Si])OC1[Rf]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 4.8699 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0192 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8393 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7398 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9468 -3.8819 0.0000 Si 0 0 0 0 0 2 0 0 0 0 0 0\n 7.8393 -6.6378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8699 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0192 -7.2677 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\nM RAD 1 5 3\nA 2\nR\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.3920684589521385, 0.29514757378689344, 0.4797818877743151, 0.3246623311655828 ], "category_id": 2, "text": [ "#(OMe)3" ] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5500583096619626, 0.27013506753376687, 0.7482061157361566, 0.36068034017008505 ], "category_id": 1, "smiles": "*C1OC(SP(OC)(OC)OC)OC1*", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 4.0756 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7933 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6840 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3143 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0857 -4.8268 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0420 -2.3858 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6840 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0756 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7933 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 1 0\n 3 4 1 0\n 4 5 1 0\n 4 7 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 1 0\nA 2\nR\nA 6\nP(OMe)3\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5500583096619626, 0.27013506753376687, 0.7482061157361566, 0.36068034017008505 ], "category_id": 1, "smiles": "*C1OC(SP(OC)(OC)OC)OC1*", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 4.0756 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7933 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6840 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3143 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0857 -4.8268 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0420 -2.3858 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6840 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0756 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7933 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 1 0\n 3 4 1 0\n 4 5 1 0\n 4 7 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 1 0\nA 2\nR\nA 6\nP(OMe)3\nA 9\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.19180707627981977, 0.4527263631815908, 0.3656487514755793, 0.5262631315657829 ], "category_id": 1, "smiles": "*C1OC2(*=[SH]2)OC1[Rf]", "molfile": "\n RDKit 2D\n\n 9 10 0 0 0 0 0 0 0 0999 V2000\n 4.9036 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1015 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0559 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9824 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7844 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7844 -2.8583 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0559 -6.8740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9036 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1015 -7.4252 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 5 6 2 0\n 7 8 1 0\n 8 9 1 0\nA 2\nR\nA 5\nP(OMe)3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.19180707627981977, 0.4527263631815908, 0.3656487514755793, 0.5262631315657829 ], "category_id": 1, "smiles": "*C1OC2(*=[SH]2)OC1[Rf]", "molfile": "\n RDKit 2D\n\n 9 10 0 0 0 0 0 0 0 0999 V2000\n 4.9036 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1015 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0559 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9824 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7844 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7844 -2.8583 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0559 -6.8740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9036 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1015 -7.4252 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 5 6 2 0\n 7 8 1 0\n 8 9 1 0\nA 2\nR\nA 5\nP(OMe)3\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.29325875298980714, 0.4317158579289645, 0.38202897011104603, 0.45822911455727866 ], "category_id": 2, "text": [ ":P(OMe)3" ] } ], "conditions": [], "products": [ { "category": "[Txt]", "bbox": [ 0.46498685158744196, 0.47723861930965483, 0.5748928346899282, 0.5062531265632816 ], "category_id": 2, "text": [ "s-P(OMe)3" ] }, { "category": "[Mol]", "bbox": [ 0.611880425157111, 0.45222611305652827, 0.78994925354912, 0.5247623811905953 ], "category_id": 1, "smiles": "*C1OC(P(OC)(OC)OC)OC1[1*]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 5.1057 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0058 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3879 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3937 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0406 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3879 -6.6378 0.0000 O 0 0 0 0 0 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1 2 1 0\n 1 4 1 0\n 2 3 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM ISO 4 5 1 6 2 8 4 10 3\nA 2\n(AcO)2Pb\nA 3\nOAc\nA 5\nR1\nA 6\nR2\nA 8\nR4\nA 10\nR3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Txt]", "bbox": [ 0.07403701850925462, 0.7799569427570929, 0.15907953976988495, 0.8573572500535982 ], "category_id": 2, "text": [ "HOAc" ] }, { "category": "[Mol]", "bbox": [ 0.19109554777388693, 0.6608795469163153, 0.36368184092046024, 0.9724653993663499 ], "category_id": 1, "smiles": "[1*]C1([2*])O[Pb](OC(C)=O)(OC(C)=O)OC1([3*])[4*]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.4726 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7299 -1.9134 0.0000 Pb 0 0 0 0 0 4 0 0 0 0 0 0\n 7.2925 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6463 -3.4094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4276 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2990 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8231 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8585 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0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8585 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0739 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3761 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6398 -3.4094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 11 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM ISO 4 6 2 7 1 9 4 10 3\nA 1\nAcO\nA 3\nOAc\nA 6\nR2\nA 7\nR1\nA 9\nR4\nA 10\nR3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.49524762381190596, 0.7204182448367041, 0.6143071535767884, 0.9178882596059935 ], "category_id": 1, "smiles": "[1*]C([2*])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.6063 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8688 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1570 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6063 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.6543271635817909, 0.7184336215726912, 0.7728864432216108, 0.9159036363419806 ], "category_id": 1, "smiles": "[3*]C([4*])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.6182 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2473 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1764 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6182 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 3 3 4\nA 2\nR3\nA 3\nR4\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.8104052026013007, 0.7640799566449892, 0.9439719859929965, 0.8623188082136307 ], "category_id": 2, "text": [ "Pb(OAc)2" ] } ] } ], "Criegee mechanism of ozonolysis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.060030015007503754, 0.04095372118636088, 0.17708854427213608, 0.30359171575106647 ], "category_id": 1, "smiles": "CC(C)=C(C)C.O=O[O-]", "molfile": "\n RDKit 2D\n\n 9 7 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 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0.5212606303151576, 0.5243856908427512, 0.6678339169584793, 0.6828587858682346 ], "category_id": 1, "smiles": "CC1(C)OOC(C)(C)O1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 1.9463 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9307 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7785 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3043 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6779 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6623 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.7003 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3804 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2282 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 9 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\nM END\n" } ] } ], "Curtius rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.13506753376688344, 0.10935210370458542, 0.21560780390195097, 0.18225350617430902 ], "category_id": 1, "smiles": "*C(=O)Cl", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1495 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9196 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2138 -3.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1495 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8553 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 6 1 0\n 4 5 1 0\n 6 7 2 0\n 6 12 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\n 11 12 2 0\nM CHG 1 3 -1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8159079539769885, 0.0999187159998703, 0.886943471735868, 0.1587361161983755 ], "category_id": 2, "text": [ "aryl" ] }, { "category": "[Txt]", "bbox": [ 0.7838919459729865, 0.1877904946096853, 0.9174587293646823, 0.2430646779287625 ], "category_id": 2, "text": [ "migration" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.058029014507253625, 0.435815676169647, 0.344672336168084, 0.6739198504672103 ], "category_id": 1, "smiles": "[H]C(=O)Oc1ccc(O)cc1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 5.9186 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7080 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1522 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9186 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3399 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5505 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1063 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3169 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.7382 -5.4567 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1063 -7.6614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3399 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.058029014507253625, 0.435815676169647, 0.344672336168084, 0.6739198504672103 ], "category_id": 1, "smiles": "[H]C(=O)Oc1ccc(O)cc1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 5.9186 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7080 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9 11 1 0\n 11 12 1 0\n 12 13 1 0\n 14 15 1 0\nA 15\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.10605302651325663, 0.6322488634917134, 0.2836418209104552, 0.9283791004091997 ], "category_id": 1, "smiles": "*CN1(CO[H])CN2CN([H])CN(C2)C1", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.9095 -3.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1700 -4.5883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.5796 -5.1013 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2395 -4.0753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.1700 -4.5883 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 12 1 0\n 2 3 1 0\n 2 10 1 0\n 3 4 1 0\n 4 5 1 0\n 4 8 1 0\n 4 14 1 0\n 5 6 1 0\n 6 7 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 12 13 1 0\n 14 15 1 0\nA 15\nAr\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3811905952976488, 0.750052497885896, 0.44072036018009003, 0.9154098929529595 ], "category_id": 1, "smiles": "C=O", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 2.0300 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9070 -1.2047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.45672836418209106, 0.6354911653557735, 0.6353176588294147, 0.9359444714253399 ], "category_id": 1, "smiles": "*CN1CN2CN([H])CN(C1)C2", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 1.8205 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8205 -6.2441 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3490 -6.8740 0.0000 C 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7764 -6.2441 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3049 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4289 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5627 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0342 -7.8976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5057 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0342 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3490 -2.7795 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3490 -0.1024 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 9 1 0\n 3 4 1 0\n 4 5 1 0\n 4 7 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\nA 6\nAr\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7703851925962981, 0.6960141334848948, 0.9054527263631816, 0.9154098929529595 ], "category_id": 1, "smiles": "*C[NH3+]", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 5.8620 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9889 -3.1732 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0023 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0 0 0 0 0 0 0 0 0 0 0\n 2.7969 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7197 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6913 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2646 -7.2677 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 2.7969 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1102 -2.1496 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.7323 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1795 -2.1496 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 20.6268 -0.4961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6630 -0.4961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 1 0\n 2 3 1 0\n 3 4 1 0\n 3 6 1 0\n 4 5 1 0\n 7 8 1 0\n 7 11 2 0\n 8 9 1 0\n 9 10 2 0\nM CHG 1 5 1\nM RAD 1 5 2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.11167066786982008, 0.23261630815407705, 0.40201440433135227, 0.3551775887943972 ], "category_id": 1, "smiles": "O=NON=O.[NH2+]CC1CCC1", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 0.6992 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7969 -6.7165 0.0000 C 0 0 0 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0 0 0 0 0 0 0 0 0 0 0 0\n 2.4989 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4346 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4346 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4989 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3460 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8006 -1.6772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3217 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7784 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6033 -2.6220 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9514 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 12 1 0\n 2 13 1 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 13 14 1 0\n 14 15 1 0\n 14 16 1 0\n 14 17 1 0\nM ISO 2 15 1 17 2\nA 1\nOAc\nA 3\nAcO\nA 15\nR1\nA 17\nR2\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.871935967983992, 0.20005002501250624, 0.9654827413706853, 0.2981697991853069 ], "category_id": 2, "text": [ "@OAc" ] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.2926463231615808, 0.6582598442078181, 0.4287143571785893, 0.8725991567212178 ], "category_id": 1, "smiles": "[1*]C([2*])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 6.0731 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5621 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4892 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0731 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5282641320660331, 0.5830029300364468, 0.7198599299649825, 0.9459508325591367 ], "category_id": 1, "smiles": "CC(=O)OI1OC(=O)c2ccccc21", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 6.5354 -2.1496 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0866 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8740 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5354 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2441 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4094 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4409 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4724 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4724 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4409 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4094 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 11 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\nA 2\nOAc\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.8119059529764883, 0.7201800900450225, 0.9139569784892446, 0.808773672550561 ], "category_id": 2, "text": [ "AcOH" ] } ] } ], "Di-\u03c0-methane rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03651825912956478, 0.1587698611210367, 0.16808404202101052, 0.7109361559086421 ], "category_id": 1, "smiles": "*C([1*])(C=C)/C([2*])=C(/[3*])[4*]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3847 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8420 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1924 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8356 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8891 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8356 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5771 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0280 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\nM ISO 4 4 1 7 2 9 4 10 3\nA 4\nR1\nA 5\nR\nA 7\nR2\nA 9\nR4\nA 10\nR3\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.21360680340170085, 0.29284218828991215, 0.2571285642821411, 0.40398109107463787 ], "category_id": 2, "text": [ "hv" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.32216108054027015, 0.15700575155302518, 0.4627313656828414, 0.7109361559086421 ], "category_id": 1, "smiles": "[1*]C1([1*])C(I)C1C([3*])[4*]", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 4.2036 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3946 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5857 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3946 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4329 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2419 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6240 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3311 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3311 -6.4803 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 8 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\nM ISO 4 1 4 3 3 6 1 7 1\nA 1\nR4\nA 3\nR3\nA 6\nR1\nA 7\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.32216108054027015, 0.15700575155302518, 0.4627313656828414, 0.7109361559086421 ], "category_id": 1, "smiles": "[1*]C1([1*])C(I)C1C([3*])[4*]", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 4.2036 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3946 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5857 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3946 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4329 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2419 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6240 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3311 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3311 -6.4803 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 8 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\nM ISO 4 1 4 3 3 6 1 7 1\nA 1\nR4\nA 3\nR3\nA 6\nR1\nA 7\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5657828914457229, 0.11643123148876025, 0.6998499249624812, 0.6703616358443771 ], "category_id": 1, "smiles": "*C([1*])C([2*])(C=C)C([3*])[4*]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5647 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9820 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7919 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9516 -2.3858 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7919 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3071 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0067 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 8 1 0\n 6 7 2 0\n 8 9 1 0\n 8 10 1 0\nM ISO 4 3 1 5 2 9 4 10 3\nA 1\nR\nA 3\nR1\nA 5\nR2\nA 9\nR4\nA 10\nR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5657828914457229, 0.11643123148876025, 0.6998499249624812, 0.6703616358443771 ], "category_id": 1, "smiles": "*C([1*])C([2*])(C=C)C([3*])[4*]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5647 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9820 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7919 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9516 -2.3858 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7919 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3071 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0067 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 8 1 0\n 6 7 2 0\n 8 9 1 0\n 8 10 1 0\nM ISO 4 3 1 5 2 9 4 10 3\nA 1\nR\nA 3\nR1\nA 5\nR2\nA 9\nR4\nA 10\nR3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8159079539769885, 0.13054410803285238, 0.9459729864932466, 0.6350794444841468 ], "category_id": 1, "smiles": "*C1([1*])C([3*])([4*])C1([2*])C=C", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 0.5751 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5751 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8038 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4379 -1.5984 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1044 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1044 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4050 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1044 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4050 -1.3622 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1044 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 8 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 8 10 1 0\nM ISO 4 4 2 6 4 7 3 9 1\nA 4\nR2\nA 6\nR4\nA 7\nR3\nA 9\nR1\nA 10\nR\nM END\n" } ] } ], "Dieckmann condensation.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04502251125562781, 0.16220272298311317, 0.17158579289644824, 0.8851062167720497 ], "category_id": 1, "smiles": "[H]C(CCCC(=O)OCC)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 3.3014 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8708 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3301 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3301 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8708 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3756 -4.6693 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5765 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0621 -1.9921 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7870 -4.1969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 2 0\nA 1\nCO2Et\nA 8\nOEt\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.208104052026013, 0.3624529982709072, 0.29364682341170584, 0.47259064967919395 ], "category_id": 2, "text": [ "enolate" ] }, { "category": "[Txt]", "bbox": [ 0.19909954977488745, 0.5446807487827998, 0.3021510755377689, 0.6588234056968425 ], "category_id": 2, "text": [ "formation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3381690845422711, 0.23028781658096314, 0.46673336668334164, 0.8590736809846365 ], "category_id": 1, "smiles": "*C(=CCCCC(=O)OCC)OCC", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 5.8952 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2292 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2544 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1787 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3845 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3845 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1787 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2292 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8952 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6389 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 3\n 8 9 1 0\n 8 10 1 0\nA 1\nOEt\nA 9\nOEt\nA 10\nOo\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3381690845422711, 0.23028781658096314, 0.46673336668334164, 0.8590736809846365 ], "category_id": 1, "smiles": "*C(=CCCCC(=O)OCC)OCC", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 5.8952 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2292 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2544 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1787 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3845 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3845 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1787 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2292 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8952 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6389 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 3\n 8 9 1 0\n 8 10 1 0\nA 1\nOEt\nA 9\nOEt\nA 10\nOo\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4942471235617809, 0.3624529982709072, 0.6018009004502252, 0.4826031634435836 ], "category_id": 2, "text": [ "5-exo-trig" ] }, { "category": "[Txt]", "bbox": [ 0.4842421210605303, 0.5546932625471895, 0.6108054027013506, 0.6748434277198659 ], "category_id": 2, "text": [ "ring closure" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6368184092046023, 0.2282853138280852, 0.7668834417208604, 0.7789735708695188 ], "category_id": 1, "smiles": "CCOC(=O)C1CCCC1(O)OCC", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 6.6216 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3152 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5056 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5712 -5.7717 0.0000 C 0 0 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0\n 2 4 1 0\n 2 8 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\nA 1\nOEt\nA 5\nCO2Et\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.848424212106053, 0.36045049551802927, 0.9759879939969985, 0.7669585543522512 ], "category_id": 1, "smiles": "CCOC(=O)C1CCCC1=O", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 4.7043 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4684 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6844 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6246 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2342 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6860 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6661 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\nA 2\nCO2Et\nM END\n" } ] } ], "Diels\u2013Alder reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05002501250625312, 0.09414118824117941, 0.24212106053026514, 0.3425693238776251 ], "category_id": 1, "smiles": "C=C(C=COC)O[Si](C)(C)C", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 9.7192 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7192 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6063 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6063 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4934 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7192 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\nA 2\nOMe\nA 5\nMe3SiO\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.22011005502751377, 0.14208346003066893, 0.39419709854927465, 0.3303658365130278 ], "category_id": 1, "smiles": "CCOC(=O)/C=C\\OOC(C)=O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 16.1538 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4827 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1405 -5.6929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3422 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -2.3071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3422 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3422 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -5.6929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3422 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 1 0\nA 9\nAcO\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4222111055527764, 0.1499285590507672, 0.5867933966983492, 0.21617606188715272 ], "category_id": 2, "text": [ "hydroquinone" ] }, { "category": "[Txt]", "bbox": [ 0.39719859929964985, 0.2597599453321432, 0.615807903951976, 0.3242640928307291 ], "category_id": 2, "text": [ "180 %C, 1.5 h, 62%" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6258129064532266, 0.044455561113890284, 0.896448224112056, 0.43060876843650586 ], "category_id": 1, "smiles": "[H]C1(C(=O)OCC)=C(OC(C)=O)C=C(O[Si](C)(C)C)C=C1OC", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 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0 0 0 0 0 0 0 0 0 0 0 0\n 7.8241 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6903 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3136 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 22.5833 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1378 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1378 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0479 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\nA 1\nOMe\nA 5\nMe3SiO\nA 7\nCO2Et\nA 10\nAcO\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.19409704852426213, 0.6894970360997493, 0.5172586293146574, 0.9387968494050947 ], "category_id": 1, "smiles": "C=C(C=COC)O[Si](C)(C)C.CCOC(=O)C=COC(C)=O", "molfile": "\n RDKit 2D\n\n 10 8 0 0 0 0 0 0 0 0999 V2000\n 10.3136 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3136 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8241 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8241 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6903 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3136 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 22.5833 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1378 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1378 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0479 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\nA 1\nOMe\nA 5\nMe3SiO\nA 7\nCO2Et\nA 10\nAcO\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.624312156078039, 0.6528865740059573, 0.8994497248624312, 0.901314709642403 ], "category_id": 1, "smiles": "CCO[C@@H]1[C@@H](OC(C)=O)CC(O[Si](C)(C)C)=C[C@H]1OC", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 9.0945 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0945 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9724 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6988 -2.4646 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9724 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6988 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0945 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2165 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3386 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2165 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 10 1 0\n 3 5 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\n 2 1 1 6\n 3 4 1 1\n 5 6 1 6\nA 1\nOMe\nA 4\nEtO\nA 6\nAcO\nA 9\nOSiMe3\nM END\n" } ] } ], "Dienone\u2013phenol rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.06453226613306653, 0.35008754377188595, 0.15457728864432216, 0.9280098382524596 ], "category_id": 1, "smiles": "*C1(*)C=CC(=O)C=C1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 2.1895 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0948 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1816 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9685 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9685 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1895 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1895 -0.3386 0.0000 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"molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 0.4849 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4849 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5459 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6069 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6679 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7289 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7289 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7899 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8509 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9119 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9119 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8509 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7899 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6069 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5459 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3661830915457729, 0.1116039191143689, 0.5767883941970986, 0.30202810610326086 ], "category_id": 1, "smiles": "O/C(=N\\c1ccccc1)c1ccccc1", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 0.4849 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4849 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5459 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6069 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6679 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7289 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7289 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7899 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8509 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9119 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9119 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8509 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7899 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6069 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5459 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5892946473236619, 0.14229499687082037, 0.6658329164582291, 0.19460933395568078 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6888444222111055, 0.04394404315128275, 0.9409704852426213, 0.319466218464881 ], "category_id": 1, "smiles": "[H]N(=CC1=CC=CC=C1)C1=CC=CC=C1.[H]OC(=C)C(=O)O", "molfile": "\n RDKit 2D\n\n 20 20 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -8.2500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 4.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 5.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 6.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 15 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 1 0\n 5 7 2 3\n 7 8 1 0\n 8 9 1 0\n 8 13 2 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 14 15 1 0\n 16 17 2 0\n 17 18 1 0\n 17 19 1 0\n 19 20 1 0\nA 18\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6888444222111055, 0.04394404315128275, 0.9409704852426213, 0.319466218464881 ], "category_id": 1, "smiles": "[H]N(=CC1=CC=CC=C1)C1=CC=CC=C1.[H]OC(=C)C(=O)O", "molfile": "\n RDKit 2D\n\n 20 20 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -8.2500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 4.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 5.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 6.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 15 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 1 0\n 5 7 2 3\n 7 8 1 0\n 8 9 1 0\n 8 13 2 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 14 15 1 0\n 16 17 2 0\n 17 18 1 0\n 17 19 1 0\n 19 20 1 0\nA 18\nCO2H\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.128064032016008, 0.4150270742065593, 0.3401700850425213, 0.6368398634463676 ], "category_id": 1, "smiles": "O=C(O)C(=O)CC(Nc1ccccc1)c1ccccc1", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 0.3134 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3134 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1935 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9691 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7448 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5205 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5205 -2.4646 0.0000 C 0 0 0 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1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 17 1 0\n 5 6 1 0\n 6 7 1 0\n 6 11 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\n 11 12 2 0\n 11 16 1 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 2 0\n 17 18 2 0\nA 9\nCO2H\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4447223611805903, 0.41711964768995374, 0.656328164082041, 0.6431175838965508 ], "category_id": 1, "smiles": "[H]N1=C2C=CC=CC2([H])C(O)(C(=O)O)CC1C1=CC=CC=C1", "molfile": "\n RDKit 2D\n\n 20 22 0 0 0 0 0 0 0 0999 V2000\n -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6491 -3.5623 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5190 -1.9364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.9559 -1.1509 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 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0 0 0 0 0 0 0\n 3.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 11 1 0\n 7 8 1 0\n 7 12 2 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\n 15 16 1 0\n 15 20 2 0\n 16 17 2 0\n 17 18 1 0\n 18 19 2 0\n 19 20 1 0\nA 3\nCO2H\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6573286643321661, 0.47710675421392706, 0.7023511755877939, 0.5322111892766467 ], "category_id": 2, "text": [ "H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7138569284642321, 0.40177410881172804, 0.9239619809904952, 0.652882926819058 ], "category_id": 1, "smiles": "[H]C1C(c2ccccc2)Nc2ccccc2C1(O)C(=O)O", "molfile": "\n RDKit 2D\n\n 19 21 0 0 0 0 0 0 0 0999 V2000\n 6.6657 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4247 -2.7795 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0919 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0177 -0.8110 0.0000 R 0 0 0 0 0 0 0 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4\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7138569284642321, 0.40177410881172804, 0.9239619809904952, 0.652882926819058 ], "category_id": 1, "smiles": "[H]C1C(c2ccccc2)Nc2ccccc2C1(O)C(=O)O", "molfile": "\n RDKit 2D\n\n 19 21 0 0 0 0 0 0 0 0999 V2000\n 6.6657 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4247 -2.7795 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0919 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0177 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1661 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5180 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9442 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3703 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3703 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9442 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5180 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0919 -5.9291 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6657 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2396 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8134 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3873 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3873 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8134 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2396 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\n 14 15 2 0\n 14 19 1 0\n 15 16 1 0\n 16 17 2 0\n 17 18 1 0\n 18 19 2 0\nA 4\nCO2H\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.14107053526763383, 0.796572972678808, 0.21460730365182593, 0.8474922607747388 ], "category_id": 2, "text": [ "Hzo" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.23911955977988994, 0.7310056701991163, 0.4487243621810905, 0.9597937043835726 ], "category_id": 1, "smiles": "O=C(O)C1=CC(c2ccccc2)Nc2ccccc21", "molfile": "\n RDKit 2D\n\n 17 19 0 0 0 0 0 0 0 0999 V2000\n 0.4026 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4026 -4.6693 0.0000 C 0 0 0 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0\nA 15\nCO2H\nM END\n" } ] } ], "Doebner\u2013von Miller reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05302651325662831, 0.02119173993776549, 0.23411705852926462, 0.18860648544611286 ], "category_id": 1, "smiles": "CC(C)c1ccc(N)cc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 0.4794 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9963 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9963 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6331 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3897 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3860 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3860 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2212 -9.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3897 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6331 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 2 0\n 4 10 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.2546273136568284, 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0\n 3 20 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 19 1 0\n 7 8 1 0\n 8 9 1 0\n 8 17 1 0\n 8 18 1 0\n 9 10 1 0\n 9 16 1 0\n 10 11 2 0\n 10 12 1 0\n 12 13 1 0\n 13 14 1 0\n 13 15 1 0\n 15 16 1 0\n 19 20 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.15657828914457228, 0.2500625312656328, 0.27613806903451726, 0.2917396198099049 ], "category_id": 2, "text": [ "irreversible" ] }, { "category": "[Txt]", "bbox": [ 0.14357178589294647, 0.3171697077352235, 0.2896448224112056, 0.3595531876107545 ], "category_id": 2, "text": [ "fragmentation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.33166583291645824, 0.21827492135898455, 0.5342671335667833, 0.37933214488600225 ], "category_id": 1, "smiles": "CC(C)=Nc1ccc(C(C)C)cc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.5628 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9549 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3470 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3470 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7391 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1312 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5233 -7.8189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9154 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9154 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.3075 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1312 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7391 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9549 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 13 1 0\n 3 4 2 0\n 3 12 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 11 1 0\n 7 8 2 3\n 8 9 1 0\n 8 10 1 0\n 11 12 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5797898949474737, 0.21474296470269033, 0.673336668334167, 0.37156184024215494 ], "category_id": 1, "smiles": "CC1CCCC(=O)C1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 8.0226 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4821 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4821 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0085 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0085 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6017 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6017 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0085 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.33166583291645824, 0.21827492135898455, 0.5342671335667833, 0.37933214488600225 ], "category_id": 1, "smiles": "CC(C)=Nc1ccc(C(C)C)cc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.5628 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9549 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3470 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3470 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7391 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1312 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5233 -7.8189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9154 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9154 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.3075 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1312 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7391 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9549 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 13 1 0\n 3 4 2 0\n 3 12 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 11 1 0\n 7 8 2 3\n 8 9 1 0\n 8 10 1 0\n 11 12 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5797898949474737, 0.21474296470269033, 0.673336668334167, 0.37156184024215494 ], "category_id": 1, "smiles": "CC1CCCC(=O)C1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 8.0226 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4821 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4821 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0085 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0085 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6017 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6017 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0085 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6973486743371686, 0.25076892259689165, 0.8359179589794897, 0.29385879380368146 ], "category_id": 2, "text": [ "condensation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.05902951475737869, 0.4944739318811948, 0.34667333666833416, 0.6625950687208011 ], "category_id": 1, "smiles": "CC(/C=C1/CCCC(C)C1)=N\\c1ccc(C(C)C)cc1", "molfile": "\n RDKit 2D\n\n 20 21 0 0 0 0 0 0 0 0999 V2000\n 21.3839 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.3839 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.0927 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.0927 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6107 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3196 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3196 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0284 -7.8189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7373 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4462 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1550 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1550 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8639 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8639 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5728 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4462 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7373 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.3839 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.6750 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.6750 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 20 1 0\n 3 4 1 0\n 4 5 2 0\n 4 18 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 2 0\n 9 17 1 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 12 16 1 0\n 13 14 1 0\n 13 15 1 0\n 16 17 2 0\n 18 19 1 0\n 19 20 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05902951475737869, 0.4944739318811948, 0.34667333666833416, 0.6625950687208011 ], "category_id": 1, "smiles": "CC(/C=C1/CCCC(C)C1)=N\\c1ccc(C(C)C)cc1", "molfile": "\n RDKit 2D\n\n 20 21 0 0 0 0 0 0 0 0999 V2000\n 21.3839 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.3839 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.0927 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.0927 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6107 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3196 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3196 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0284 -7.8189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7373 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4462 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1550 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1550 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8639 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8639 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5728 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4462 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7373 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.3839 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.6750 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.6750 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 20 1 0\n 3 4 1 0\n 4 5 2 0\n 4 18 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 2 0\n 9 17 1 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 12 16 1 0\n 13 14 1 0\n 13 15 1 0\n 16 17 2 0\n 18 19 1 0\n 19 20 1 0\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.4032016008004002, 0.4019366674862855, 0.5862931465732867, 0.5700578043258917 ], "category_id": 1, "smiles": "CC(C)c1ccc(N)cc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 0.4835 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9010 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1975 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1975 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4941 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7907 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0873 -7.4252 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7907 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4941 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9010 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 1 0\n 3 4 2 0\n 3 9 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.40670335167583793, 0.5997262402387634, 0.59879939969985, 0.6442288941080709 ], "category_id": 2, "text": [ "conjugate addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6383191595797899, 0.42666036408034524, 0.9229614807403702, 0.7360597671717214 ], "category_id": 1, "smiles": "C/C(CC1(Nc2ccc(C(C)C)cc2)CCCC(C)C1)=N\\c1ccc(C(C)C)cc1", "molfile": "\n RDKit 2D\n\n 30 32 0 0 0 0 0 0 0 0999 V2000\n 11.4350 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4350 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2098 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2098 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2098 -4.3543 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9847 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9847 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7595 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5343 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2070 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9818 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2070 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5343 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7595 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9847 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7595 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7595 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5343 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2070 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9818 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7567 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7567 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5315 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5315 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3063 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9818 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2070 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4350 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6602 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6602 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 30 1 0\n 3 4 1 0\n 4 5 1 0\n 4 15 1 0\n 4 28 1 0\n 5 6 1 0\n 6 7 2 0\n 6 14 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 13 1 0\n 10 11 1 0\n 10 12 1 0\n 13 14 2 0\n 15 16 1 0\n 16 17 1 0\n 16 18 2 0\n 18 19 1 0\n 19 20 2 0\n 19 27 1 0\n 20 21 1 0\n 21 22 2 0\n 22 23 1 0\n 22 26 1 0\n 23 24 1 0\n 23 25 1 0\n 26 27 2 0\n 28 29 1 0\n 29 30 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6383191595797899, 0.42666036408034524, 0.9229614807403702, 0.7360597671717214 ], "category_id": 1, "smiles": "C/C(CC1(Nc2ccc(C(C)C)cc2)CCCC(C)C1)=N\\c1ccc(C(C)C)cc1", "molfile": "\n RDKit 2D\n\n 30 32 0 0 0 0 0 0 0 0999 V2000\n 11.4350 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4350 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2098 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2098 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2098 -4.3543 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9847 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9847 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7595 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5343 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2070 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9818 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2070 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5343 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7595 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9847 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7595 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7595 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5343 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2070 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9818 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7567 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7567 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5315 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5315 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3063 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9818 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2070 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4350 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6602 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6602 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 30 1 0\n 3 4 1 0\n 4 5 1 0\n 4 15 1 0\n 4 28 1 0\n 5 6 1 0\n 6 7 2 0\n 6 14 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 13 1 0\n 10 11 1 0\n 10 12 1 0\n 13 14 2 0\n 15 16 1 0\n 16 17 1 0\n 16 18 2 0\n 18 19 1 0\n 19 20 2 0\n 19 27 1 0\n 20 21 1 0\n 21 22 2 0\n 22 23 1 0\n 22 26 1 0\n 23 24 1 0\n 23 25 1 0\n 26 27 2 0\n 28 29 1 0\n 29 30 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2016008004002001, 0.8187075529290068, 0.31765882941470736, 0.8660357721233498 ], "category_id": 2, "text": [ "cyclization" ] }, { "category": "[Txt]", "bbox": [ 0.17708854427213608, 0.8829891640735622, 0.34217108554277137, 0.9274918179428697 ], "category_id": 2, "text": [ "rearomatization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.36668334167083544, 0.7523067677906748, 0.6008004002001001, 0.9981309510687547 ], "category_id": 1, "smiles": "CC1=CC2(CCCC(C)C2)Nc2ccc(C(C)C)cc21", "molfile": "\n RDKit 2D\n\n 20 22 0 0 0 0 0 0 0 0999 V2000\n 11.4417 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4417 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8525 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8525 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2634 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6743 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0852 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4961 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4961 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0129 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0129 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3178 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0852 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6743 -2.1496 0.0000 C 0 0 0 0 0 0 0 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"bbox": [ 0.6043021510755378, 0.03611011281814192, 0.8404202101050525, 0.31054697023602057 ], "category_id": 1, "smiles": "C[NH2]1=CC=CC=C1OCC1=CC=CC=C1", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 N 0 0 0 0 0 6 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 15 2 0\n 3 4 1 0\n 3 12 2 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.030015007503751877, 0.6427600081629262, 0.23461730865432717, 0.8461803103717923 ], "category_id": 1, "smiles": "COc1ccc(CO)cc1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 8.9690 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9157 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0222 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.0755 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.0755 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9379 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 20.9912 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0222 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9690 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 9 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 8 1 0\n 6 7 1 0\n 8 9 2 0\nA 2\nH3CO\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.24762381190595298, 0.6030388840629701, 0.40220110055027514, 0.88710510489902 ], "category_id": 1, "smiles": "Cc1cc(Cl)nc2ccccc12", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 6.2058 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2058 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1372 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1372 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4480 -7.8189 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2058 -7.8189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3778 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3778 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5498 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6184 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6184 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5498 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 8 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4532266133066533, 0.6584077237174545, 0.6258129064532266, 0.7306279493537382 ], "category_id": 2, "text": [ "KOH, 18-crown-6" ] }, { "category": "[Txt]", "bbox": [ 0.43271635817908954, 0.7655343917446088, 0.6468234117058529, 0.88710510489902 ], "category_id": 2, "text": [ "toluene, reflux (~HzO)", "90-93%" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6533266633316658, 0.5272076471448721, 0.9684842421210605, 0.9232152177171618 ], "category_id": 1, "smiles": "COc1ccc(COc2cc(C)c3ccccc3n2)cc1", "molfile": "\n RDKit 2D\n\n 20 22 0 0 0 0 0 0 0 0999 V2000\n 14.2200 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2200 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7072 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7072 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0432 -5.0630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5304 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0177 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0177 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5049 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9921 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3281 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9921 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5049 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2200 -5.0630 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.7328 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.7328 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.2455 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.7583 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.7583 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.2455 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 16 1 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 7 13 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 14 15 1 0\n 15 16 2 0\n 15 20 1 0\n 16 17 1 0\n 17 18 2 0\n 18 19 1 0\n 19 20 2 0\nA 11\nH3CO\nM END\n" } ] } ], "D\u00f6tz reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03601800900450225, 0.09342799742117049, 0.25812906453226614, 0.27029932078338637 ], "category_id": 1, "smiles": "*OC(=*)/C(*)=C/[2*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 11.3720 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9681 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9681 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3720 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8794 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1799 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5839 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\nM ISO 1 7 2\nA 2\nR\nA 4\nOR\nA 5\n(OC)5Cr\nA 7\nR2\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.27163581790895447, 0.12266882104153681, 0.3366683341670835, 0.1718789876221533 ], "category_id": 2, "text": [ "CO" ] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.37168584292146073, 0.08415651676105433, 0.5917958979489745, 0.2624542217632881 ], "category_id": 1, "smiles": "*OC(=*)/C(*)=C/[2*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 11.5911 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1946 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1946 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5911 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2619 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5238 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.9204 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\nM ISO 1 7 2\nA 2\nR\nA 4\nOR\nA 5\n(OC)4Cr\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.37168584292146073, 0.08415651676105433, 0.5917958979489745, 0.2624542217632881 ], "category_id": 1, "smiles": "*OC(=*)/C(*)=C/[2*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 11.5911 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1946 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1946 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5911 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2619 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5238 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.9204 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\nM ISO 1 7 2\nA 2\nR\nA 4\nOR\nA 5\n(OC)4Cr\nA 7\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.03601800900450225, 0.09342799742117049, 0.25812906453226614, 0.27029932078338637 ], "category_id": 1, "smiles": "*OC(=*)/C(*)=C/[2*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 11.3720 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9681 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9681 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3720 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8794 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1799 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5839 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\nM ISO 1 7 2\nA 2\nR\nA 4\nOR\nA 5\n(OC)5Cr\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.37168584292146073, 0.08415651676105433, 0.5917958979489745, 0.2624542217632881 ], "category_id": 1, "smiles": "*OC(=*)/C(*)=C/[2*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 11.5911 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1946 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1946 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5911 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2619 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5238 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.9204 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\nM ISO 1 7 2\nA 2\nR\nA 4\nOR\nA 5\n(OC)4Cr\nA 7\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6238119059529765, 0.12052924858151, 0.7138569284642321, 0.17045260598213546 ], "category_id": 2, "text": [ "alkyne" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7503751875937968, 0.05990802888075054, 0.9699849924962481, 0.2731520840634221 ], "category_id": 1, "smiles": "*OC(OC(OC)(OC)OC[Cr])=C(*)C(=[2*])[3*].[1*]C#C[5*]", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 5.9130 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2463 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2318 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6665 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4636 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0868 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7970 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6230 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4636 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9418 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1012 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1012 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 2 3\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 2 0\nM ISO 4 2 1 4 5 11 3 12 2\nA 2\nR1\nA 4\nR5\nA 6\nOR\nA 7\n(OC)4Cr\nA 9\nR\nA 11\nR3\nA 12\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7503751875937968, 0.05990802888075054, 0.9699849924962481, 0.2731520840634221 ], "category_id": 1, "smiles": "*OC(OC(OC)(OC)OC[Cr])=C(*)C(=[2*])[3*].[1*]C#C[5*]", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 5.9130 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2463 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2318 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6665 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4636 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0868 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7970 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6230 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4636 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9418 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1012 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1012 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 2 3\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 2 0\nM ISO 4 2 1 4 5 11 3 12 2\nA 2\nR1\nA 4\nR5\nA 6\nOR\nA 7\n(OC)4Cr\nA 9\nR\nA 11\nR3\nA 12\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5972986493246624, 0.19470109386243925, 0.7423711855927964, 0.24105849716302 ], "category_id": 2, "text": [ "coordination" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.37168584292146073, 0.08415651676105433, 0.5917958979489745, 0.2624542217632881 ], "category_id": 1, "smiles": "*OC(=*)/C(*)=C/[2*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 11.5911 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1946 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1946 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5911 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2619 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5238 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.9204 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\nM ISO 1 7 2\nA 2\nR\nA 4\nOR\nA 5\n(OC)4Cr\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.22811405702851426, 0.3216490598240297, 0.4837418709354677, 0.6839499963885686 ], "category_id": 1, "smiles": "*OC12=C([5*])C([1*])=CC34=C(*3)C=14(*)(=C[2*])=C([2*])=C2[1*]", "molfile": "\n RDKit 2D\n\n 18 21 0 0 0 0 0 0 0 0999 V2000\n -2.4821 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.0938 -2.7479 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7811 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2300 -0.9373 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0311 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.4800 1.1382 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0311 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3301 3.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 4.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 -0.9841 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9821 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5179 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 15 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 2 0\n 5 15 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 12 13 2 0\n 12 14 1 0\n 12 15 1 0\n 13 14 1 0\n 13 15 1 0\n 15 16 1 0\n 15 17 2 0\n 17 18 1 0\nM ISO 5 2 2 4 1 8 5 10 1 18 2\nA 2\nR2\nA 4\nR1\nA 6\nOR\nA 8\nR5\nA 10\nR1\nA 14\nOR\nA 16\nR\nA 18\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5157578789394698, 0.4428914992255486, 0.6658329164582291, 0.4921016658061651 ], "category_id": 2, "text": [ "CO insertion" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6753376688344173, 0.29668738112371695, 0.9294647323661831, 0.6625542717883006 ], "category_id": 1, "smiles": "*C(=C[2*])C12C([5*])C34([1*])C5C([1*])C13(=O)C5([1*])C24[5*]", "molfile": "\n RDKit 2D\n\n 18 22 0 0 0 0 0 0 0 0999 V2000\n 2.5095 -1.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5702 -2.7938 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0607 -2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9497 -2.9107 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0607 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5607 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 2.1213 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8367 -1.1726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1213 -1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6213 -1.0607 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1213 1.0607 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3624 -2.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6919 -3.5230 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 -2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1213 -3.1820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 3\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 13 1 0\n 5 17 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 13 1 0\n 8 17 1 0\n 10 11 1 0\n 10 15 1 0\n 11 12 1 0\n 11 13 1 0\n 11 17 1 0\n 13 14 1 0\n 15 16 1 0\n 15 17 1 0\n 17 18 2 0\nM ISO 6 2 2 7 5 9 1 12 1 14 5 16 1\nA 2\nR2\nA 4\nR\nA 7\nR5\nA 9\nR1\nA 12\nR1\nA 14\nR5\nA 16\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6753376688344173, 0.29668738112371695, 0.9294647323661831, 0.6625542717883006 ], "category_id": 1, "smiles": "*C(=C[2*])C12C([5*])C34([1*])C5C([1*])C13(=O)C5([1*])C24[5*]", "molfile": "\n RDKit 2D\n\n 18 22 0 0 0 0 0 0 0 0999 V2000\n 2.5095 -1.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5702 -2.7938 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0607 -2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9497 -2.9107 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0607 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5607 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 2.1213 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8367 -1.1726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1213 -1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6213 -1.0607 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1213 1.0607 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3624 -2.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6919 -3.5230 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 -2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1213 -3.1820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 3\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 13 1 0\n 5 17 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 13 1 0\n 8 17 1 0\n 10 11 1 0\n 10 15 1 0\n 11 12 1 0\n 11 13 1 0\n 11 17 1 0\n 13 14 1 0\n 15 16 1 0\n 15 17 1 0\n 17 18 2 0\nM ISO 6 2 2 7 5 9 1 12 1 14 5 16 1\nA 2\nR2\nA 4\nR\nA 7\nR5\nA 9\nR1\nA 12\nR1\nA 14\nR5\nA 16\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.08854427213606804, 0.7902154285698999, 0.23561780890445222, 0.8451311217105879 ], "category_id": 2, "text": [ "electrocyclic" ] }, { "category": "[Txt]", "bbox": [ 0.08854427213606804, 0.867240037130865, 0.22911455727863933, 0.9157370128914725 ], "category_id": 2, "text": [ "ring closure" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.28264132066033015, 0.7203227282090243, 0.5062531265632816, 0.9677999427521248 ], "category_id": 1, "smiles": "*.*C1C(=O)C([1*])=C([5*])C(COOC([Cr])(OOC)OOC)=C1[1*]", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 4.1727 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9383 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5798 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7479 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0177 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7479 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0177 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5798 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5798 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5135 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3454 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5135 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3454 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9252 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 2 0\n 3 12 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 8 10 1 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\nM ISO 3 5 1 11 1 13 5\nA 2\nCr((COO)3\nA 5\nR1\nA 7\nRa\nA 11\nR1\nA 13\nR5\nA 14\n.\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.28264132066033015, 0.7203227282090243, 0.5062531265632816, 0.9677999427521248 ], "category_id": 1, "smiles": "*.*C1C(=O)C([1*])=C([5*])C(COOC([Cr])(OOC)OOC)=C1[1*]", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 4.1727 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9383 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5798 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7479 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0177 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7479 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0177 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5798 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5798 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5135 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3454 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5135 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3454 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9252 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 2 0\n 3 12 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 8 10 1 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\nM ISO 3 5 1 11 1 13 5\nA 2\nCr((COO)3\nA 5\nR1\nA 7\nRa\nA 11\nR1\nA 13\nR5\nA 14\n.\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5017508754377189, 0.8051924357900876, 0.6838419209604802, 0.8586817472907577 ], "category_id": 2, "text": [ "tautomerization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7073536768384192, 0.7074852934488635, 0.9309654827413707, 0.953536126351946 ], "category_id": 1, "smiles": "*C.*Oc1c(*)c([2*])c(O)c([1*])c1[5*]", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 4.7833 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8365 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4117 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1418 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5798 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5798 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8496 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0177 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8496 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0177 -6.0079 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5798 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5798 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4117 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1418 -6.0079 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 1 0\n 3 5 2 0\n 3 13 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 2 0\n 13 14 1 0\nM ISO 3 4 1 8 2 14 5\nA 2\nCr(CcO)3\nA 4\nR1\nA 8\nR2\nA 10\nR\nA 12\nOR\nA 14\nR5\nM END\n" } ] } ], "Eglinton coupling.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05152576288144072, 0.27304495869333845, 0.18259129564782392, 0.37183509450198354 ], "category_id": 1, "smiles": "*C#C[H]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 13.4154 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4252 -3.5669 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 22.8346 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 32.5394 -3.5669 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\nA 2\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.20260130065032517, 0.20718486815424172, 0.3021510755377689, 0.3046029187433223 ], "category_id": 2, "text": [ "pyridine" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3391695847923962, 0.16190605590861276, 0.4122061030515258, 0.4966948494823544 ], "category_id": 1, "smiles": "[H]N1=CC=CC=C1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4830 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 1 0\n 2 3 1 0\n 3 4 1 0\n 3 10 2 0\n 4 5 1 0\n 4 7 1 0\n 4 12 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 12 13 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3006503251625813, 0.11113890278472568, 0.4212106053026513, 0.4490011672502918 ], "category_id": 1, "smiles": "OOC12CCCCC1=C(O)CCC2", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 7.4830 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6746 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9286 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9286 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9286 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6746 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1825 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4365 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4365 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1825 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1825 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6746 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4830 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 1 0\n 2 3 1 0\n 3 4 1 0\n 3 10 2 0\n 4 5 1 0\n 4 7 1 0\n 4 12 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 12 13 1 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5127563781890946, 0.13892362848090714, 0.631815907953977, 0.38898615974654 ], "category_id": 1, "smiles": "O=C1CCCC23CCCCC12O3", "molfile": "\n RDKit 2D\n\n 12 14 0 0 0 0 0 0 0 0999 V2000\n 0.5863 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5863 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9313 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9313 -7.7402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2763 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6213 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2763 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6213 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9664 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9664 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6213 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9313 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 12 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 11 1 0\n 6 7 1 0\n 7 8 1 0\n 7 12 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5127563781890946, 0.13892362848090714, 0.631815907953977, 0.38898615974654 ], "category_id": 1, "smiles": "O=C1CCCC23CCCCC12O3", "molfile": "\n RDKit 2D\n\n 12 14 0 0 0 0 0 0 0 0999 V2000\n 0.5863 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5863 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9313 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9313 -7.7402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2763 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6213 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2763 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6213 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9664 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9664 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6213 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9313 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 12 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 11 1 0\n 6 7 1 0\n 7 8 1 0\n 7 12 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6468234117058529, 0.1933816908454227, 0.7883941970985493, 0.26451058862764715 ], "category_id": 2, "text": [ "HzNNHSOzAr" ] }, { "category": "[Txt]", "bbox": [ 0.7028514257128564, 0.28451559112889774, 0.7448724362181091, 0.36120143405035854 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.8044022011005503, 0.10447056861764216, 0.950975487743872, 0.4301075537768885 ], "category_id": 1, "smiles": "*S(=O)(=O)N/N=C1/CCCC23CCCCC12O3", "molfile": "\n RDKit 2D\n\n 14 16 0 0 0 0 0 0 0 0999 V2000\n 0.4724 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2047 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0157 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7480 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0157 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2047 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2047 -5.8504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -6.8740 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9843 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4724 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7480 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7480 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 14 1 0\n 4 5 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 2 0\n 6 10 1 0\n 7 8 1 0\n 8 9 1 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\nA 9\nSO2Ar\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.8044022011005503, 0.10447056861764216, 0.950975487743872, 0.4301075537768885 ], "category_id": 1, "smiles": "*S(=O)(=O)N/N=C1/CCCC23CCCCC12O3", "molfile": "\n RDKit 2D\n\n 14 16 0 0 0 0 0 0 0 0999 V2000\n 0.4724 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2047 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0157 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7480 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0157 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2047 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2047 -5.8504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -6.8740 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9843 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4724 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7480 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7480 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 14 1 0\n 4 5 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 2 0\n 6 10 1 0\n 7 8 1 0\n 8 9 1 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\nA 9\nSO2Ar\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.12406203101550775, 0.6968409204602302, 0.18159079539769885, 0.7846406536601633 ], "category_id": 1, "smiles": "O", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 7.6772 -5.4567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.20060030015007504, 0.6390486910121728, 0.36418209104552274, 0.9724653993663498 ], "category_id": 1, "smiles": "*N/N=C1/CCCC23CCCCC12O3.CC", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 0.4312 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0697 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8808 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5193 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8808 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0697 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0697 -5.7717 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8808 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8643 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4312 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5193 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2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -3.8971 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -5.1962 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -6.4952 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5000 0.0000 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 3 11 1 0\n 4 5 1 0\n 4 8 1 0\n 5 6 2 3\n 6 7 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 14 1 0\n 12 13 2 0\n 14 15 1 0\nM CHG 1 16 -1\nA 7\nSO2Ar\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4112056028014007, 0.5712539603134901, 0.5612806403201601, 0.9491262297815575 ], "category_id": 1, "smiles": "*S(=O)(=O)N=NC1=C2CCCCC2(O=O)CCC1.[I-]", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -3.8971 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -5.1962 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -6.4952 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 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0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 3 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5967983991995998, 0.7933802128336896, 0.7153576788394197, 0.929020191914139 ], "category_id": 1, "smiles": "*N([H])(C)C", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\nA 4\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7493746873436719, 0.7865603256173542, 0.8389194597298649, 0.863094615489563 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.864432216108054, 0.7941379780799491, 0.9559779889944973, 0.929020191914139 ], "category_id": 1, "smiles": "*N(C)(C)C", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\nA 1\n*\nM END\n" } ] } ], "Evans aldol reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.054527263631815905, 0.04557850990874338, 0.21210605302651325, 0.354719707550655 ], "category_id": 1, "smiles": "*C(=O)CC", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 7.5537 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5537 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9298 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1468 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9298 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 2 0\nA 2\nMe\nA 4\nRc\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.3356678339169585, 0.08323032244205314, 0.45722861430715356, 0.306168686126124 ], 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0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6678 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0625 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6678 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6613 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2666 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6613 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 3 1 0\n 1 6 1 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\n 1 2 1 6\n 6 8 1 6\nA 2\nMe\nA 4\nRc\nA 7\nR\nM END\n" } ] } ], "Favorskii rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2546273136568284, 0.0700393960656477, 0.37018509254627313, 0.25024492552622046 ], "category_id": 1, "smiles": "O=C1CCCCCC1Cl", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 2.0514 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6155 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3006 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7877 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9856 -2.3858 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5166 -2.7008 0.0000 C 0 0 0 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0\n 6 8 2 0\n 8 9 1 0\nM CHG 1 5 -1\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.5657828914457229, 0.4574448055537616, 0.6363181590795398, 0.5150813918994508 ], "category_id": 1, "smiles": "[Cl-]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 8.7146 -5.2205 0.0000 Cl 0 0 0 0 0 15 0 0 0 0 0 0\nM CHG 1 1 -1\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.656328164082041, 0.3910532946998664, 0.8224112056028015, 0.6084672533203144 ], "category_id": 1, "smiles": "O=C1C2CCCCC12.[O-]", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 1.4938 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3515 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4938 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5482 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5482 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6026 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6571 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6026 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8204 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] }, { "category": "[Txt]", "bbox": [ 0.30965482741370687, 0.2613718919761388, 0.5492746373186593, 0.3484958559681851 ], "category_id": 2, "text": [ "reflux; 4.5 h, 83%" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6038019009504753, 0.02010553015201068, 0.8784392196098049, 0.4300349504735617 ], "category_id": 1, "smiles": "*CC1=OC(OC)C(OS(=O)(=O)c2ccc(C)cc2)C(OC(=O)c2ccccc2)C1OC(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 12 2 0\n 4 5 1 0\n 4 6 1 1\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 6\n 10 11 1 0\n 10 12 1 0\nA 2\nHgCl\nA 5\nBzO\nA 7\nBzO\nA 9\nTsO\nA 11\nOMe\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6038019009504753, 0.02010553015201068, 0.8784392196098049, 0.4300349504735617 ], "category_id": 1, "smiles": "*CC1=OC(OC)C(OS(=O)(=O)c2ccc(C)cc2)C(OC(=O)c2ccccc2)C1OC(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 12 2 0\n 4 5 1 0\n 4 6 1 1\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 6\n 10 11 1 0\n 10 12 1 0\nA 2\nHgCl\nA 5\nBzO\nA 7\nBzO\nA 9\nTsO\nA 11\nOMe\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.03901950975487744, 0.5506681313856258, 0.3036518259129565, 0.9773521601671857 ], "category_id": 1, "smiles": "*CC1O[C@@H](OC)[C@H](O)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 6.1535 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2523 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2523 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4500 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5488 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5488 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4610 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0105 -6.7165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2634 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7471 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1645 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8570 -3.3307 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 11 1 0\n 4 5 1 0\n 5 6 1 6\n 7 8 1 0\n 7 9 1 0\n 9 10 1 1\n 11 12 1 0\n 7 5 1 6\n 11 9 1 1\nA 2\nHgCl\nA 6\nOMe\nA 10\nBzO\nA 12\nBzO\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03901950975487744, 0.5506681313856258, 0.3036518259129565, 0.9773521601671857 ], "category_id": 1, "smiles": "*CC1O[C@@H](OC)[C@H](O)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 6.1535 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2523 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2523 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4500 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5488 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5488 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4610 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0105 -6.7165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2634 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7471 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1645 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8570 -3.3307 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 11 1 0\n 4 5 1 0\n 5 6 1 6\n 7 8 1 0\n 7 9 1 0\n 9 10 1 1\n 11 12 1 0\n 7 5 1 6\n 11 9 1 1\nA 2\nHgCl\nA 6\nOMe\nA 10\nBzO\nA 12\nBzO\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3416708354177089, 0.5182758883629419, 0.5872936468234117, 0.9427259693498341 ], "category_id": 1, "smiles": "*CC[C@H](OC(=O)c1ccccc1)[C@H](OC(=O)c1ccccc1)C(O)C=O.CC", "molfile": "\n RDKit 2D\n\n 13 11 0 0 0 0 0 0 0 0999 V2000\n 6.3027 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4210 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4210 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2862 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0497 -3.1732 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4044 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7447 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5392 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3525 -6.3228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6740 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5889 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8773 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6055 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 6\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 2 0\n 12 13 1 0\n 6 4 1 6\nA 2\nHgCl\nA 5\nBzO\nA 7\nBzO\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3416708354177089, 0.5182758883629419, 0.5872936468234117, 0.9427259693498341 ], "category_id": 1, "smiles": "*CC[C@H](OC(=O)c1ccccc1)[C@H](OC(=O)c1ccccc1)C(O)C=O.CC", "molfile": "\n RDKit 2D\n\n 13 11 0 0 0 0 0 0 0 0999 V2000\n 6.3027 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4210 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4210 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2862 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0497 -3.1732 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4044 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7447 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5392 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3525 -6.3228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6740 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5889 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8773 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6055 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 6\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 2 0\n 12 13 1 0\n 6 4 1 6\nA 2\nHgCl\nA 5\nBzO\nA 7\nBzO\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7398699349674838, 0.5707736615376365, 0.9864932466233116, 0.8946960917644752 ], "category_id": 1, "smiles": "C[C@@H]1[C@H](OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)C(=O)C[C@@H]1O", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 13.0292 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5516 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5966 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7610 -4.1181 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9847 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0296 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9398 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3279 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7605 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3724 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3724 -7.2677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2 1 1 1\n 2 3 1 0\n 3 4 1 1\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 7 9 1 0\n 9 10 1 0\n 10 11 1 0\n 5 3 1 1\n 10 2 1 1\nA 4\nBzO\nA 6\nBzO\nM END\n" } ] } ], "Ferrier glycal allylic rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03601800900450225, 0.17731921123220734, 0.18309154577288644, 0.30087674671847947 ], "category_id": 1, "smiles": "CC(=O)OCC1OC=C[C@H](OC(C)=O)[C@H]1OC(C)=O", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 7.3773 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6469 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9303 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.6729 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 21.4294 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.5651 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8225 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7286 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5391 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2695 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 1\n 9 10 1 0\n 9 7 1 1\nA 1\nAcO\nA 8\nAcO\nA 10\nAcO\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.19409704852426213, 0.06319354868381857, 0.35317658829414705, 0.16505777641295896 ], "category_id": 2, "text": [ "HOCHZCCH6", "HSPh\"" ] }, { "category": "[Txt]", "bbox": [ 0.192096048024012, 0.18769427146387904, 0.31915957978989495, 0.2376831980346609 ], "category_id": 2, "text": [ "Lewis acid" ] }, { "category": "[Mol]", "bbox": [ 0.192096048024012, 0.28201300084271275, 0.3186593296648324, 0.4055705363289849 ], "category_id": 1, "smiles": "*.C=C1CCCCC1", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 19.2308 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2683 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7511 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.8080 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.2308 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.8080 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7511 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 2 0\n 3 4 1 0\n 3 8 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nA 1\n,\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3791895947973987, 0.17731921123220734, 0.5927963981990996, 0.3197404925942462 ], "category_id": 1, "smiles": "CC(=O)OCC1C[CH]C(OC(C)=O)O1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 5.5381 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7470 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0887 -3.1732 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 10.8546 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.9496 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.6079 -3.2520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 19.9370 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.0383 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 6 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\nM RAD 1 3 2\nA 1\nAcO\nA 8\nOAc\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3791895947973987, 0.17731921123220734, 0.5927963981990996, 0.3197404925942462 ], "category_id": 1, "smiles": "CC(=O)OCC1C[CH]C(OC(C)=O)O1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 5.5381 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7470 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0887 -3.1732 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 10.8546 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.9496 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.6079 -3.2520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 19.9370 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.0383 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 6 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\nM RAD 1 3 2\nA 1\nAcO\nA 8\nOAc\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6488244122061031, 0.12827347195521382, 0.7673836918459229, 0.3621839208147214 ], "category_id": 1, "smiles": "*[C@@H]1C=C[C@H](OOC(C)=O)C(COC(C)=O)O1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 4.2287 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5696 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2287 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5696 -2.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7778 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7778 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5696 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2287 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0205 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0205 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0205 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 1 0\n 5 6 1 0\n 7 8 2 0\n 9 10 1 0\n 10 11 1 0\n 5 7 1 1\n 9 8 1 1\nA 2\nOAc\nA 6\nR\nA 11\nAcO\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.135567783891946, 0.6951290355220043, 0.2836418209104552, 0.8573572500535982 ], "category_id": 1, "smiles": "CC(=O)OCC1OC=CC(OC(C)=O)C1OC(C)=O", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 4.6299 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8981 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3025 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.7068 -4.3543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4771 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0727 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6684 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1278 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5322 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5280 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 9 10 1 0\nA 1\nAcO\nA 8\nAcO\nA 10\nOAc\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.3151575787893947, 0.7234246543356544, 0.40570285142571283, 0.8592436246411749 ], "category_id": 1, "smiles": "C=C1CCCCC1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 1.0857 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5403 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5403 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0936 -8.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6469 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6469 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0936 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4352176088044022, 0.7130495941039827, 0.6438219109554777, 0.7743567682002246 ], "category_id": 2, "text": [ "SnBr4, C8H,4, EtOAc" ] }, { "category": "[Txt]", "bbox": [ 0.46823411705852924, 0.8017091997200864, 0.6098049024512256, 0.8583004373473866 ], "category_id": 2, "text": [ "rt; 5 min, 94%" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6613306653326664, 0.6328786741319741, 0.886943471735868, 0.9469600429634902 ], "category_id": 1, "smiles": "[H]C1(CC2=CCCCC2)C=CC(OC(C)=O)C(COC(C)=O)O1", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 2.5540 -2.2283 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2567 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1081 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8108 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6199 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3226 -2.8583 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6199 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1098 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1098 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7060 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1959 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1959 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7060 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6621 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9594 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0017 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4915 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 1 0\n 3 4 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 14 1 0\n 7 8 1 0\n 8 9 1 0\n 8 13 2 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 14 15 1 0\n 15 16 1 0\n 16 17 1 0\nA 1\nAcO\nA 17\nOAc\nM END\n" } ] } ], "Fiesselmann thiophene synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05002501250625312, 0.035714108010393875, 0.29064532266133064, 0.12295857186435603 ], "category_id": 1, "smiles": "COC(C#CC(=O)OC)OC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 8.3780 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1260 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.8740 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.6220 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.3858 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 21.3858 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 3 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\nA 1\nMeO2C\nA 5\nOCH3\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.11255627813906953, 0.13877481969753047, 0.2771385692846423, 0.21836626040640825 ], "category_id": 1, "smiles": "COC(=O)CS", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 11.7172 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.0178 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0865 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4558 -4.8268 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7172 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 2 0\n 3 4 1 0\nA 2\nOMe\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4337168584292146, 0.06581599904772585, 0.8244122061030515, 0.22908049280952641 ], "category_id": 1, "smiles": "COC(=O)CSC(C)=C=C([O-])OC.[H]SCC(=O)OC", "molfile": "\n RDKit 2D\n\n 17 15 0 0 0 0 0 0 0 0999 V2000\n 8.4976 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6563 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4976 -4.5118 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5663 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6007 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4763 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5663 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3944 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7120 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6776 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6776 -1.0472 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 19.8920 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.6301 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9607 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.2226 -6.4803 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2913 -6.4803 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 19.8920 -4.5118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\n 12 13 1 0\n 12 14 1 0\n 12 17 2 0\n 14 15 1 0\n 15 16 1 0\nM CHG 1 11 -1\nA 6\nH3CO\nA 10\nOMe\nA 13\nOMe\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4337168584292146, 0.06581599904772585, 0.8244122061030515, 0.22908049280952641 ], "category_id": 1, "smiles": "COC(=O)CSC(C)=C=C([O-])OC.[H]SCC(=O)OC", "molfile": "\n RDKit 2D\n\n 17 15 0 0 0 0 0 0 0 0999 V2000\n 8.4976 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6563 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4976 -4.5118 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5663 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6007 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4763 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5663 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3944 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7120 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6776 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6776 -1.0472 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 19.8920 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.6301 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9607 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.2226 -6.4803 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2913 -6.4803 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 19.8920 -4.5118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\n 12 13 1 0\n 12 14 1 0\n 12 17 2 0\n 14 15 1 0\n 15 16 1 0\nM CHG 1 11 -1\nA 6\nH3CO\nA 10\nOMe\nA 13\nOMe\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.006003001500750375, 0.2826516548251172, 0.26863431715857927, 0.4316305053827602 ], "category_id": 1, "smiles": "COC(CS/C(=C/C(=O)OC)C(OC)OC)OC", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 8.1936 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3238 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1936 -5.7717 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9333 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8031 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5841 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7142 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8333 -1.8346 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5841 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 6 2 0\n 3 4 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\nA 1\nMeO2C\nA 5\nMeO2C\nA 8\nOMe\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.006003001500750375, 0.2826516548251172, 0.26863431715857927, 0.4316305053827602 ], "category_id": 1, "smiles": "COC(CS/C(=C/C(=O)OC)C(OC)OC)OC", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 8.1936 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3238 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1936 -5.7717 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9333 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8031 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5841 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7142 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8333 -1.8346 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5841 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 6 2 0\n 3 4 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\nA 1\nMeO2C\nA 5\nMeO2C\nA 8\nOMe\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.18659329664832416, 0.39591639737236634, 0.35117558779389696, 0.4780588457962723 ], "category_id": 1, "smiles": "COC(=O)CS", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 11.3960 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8149 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9772 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3956 -4.9055 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3960 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 2 0\n 3 4 1 0\nA 2\nOMe\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4547273636818409, 0.28163125173910597, 0.7238619309654828, 0.44948755938795715 ], "category_id": 1, "smiles": "COC(CSC(/C=C(\\[O-])OC)(SCC(OC)OC)C(=O)OC)OC.[H-]", "molfile": "\n RDKit 2D\n\n 13 11 0 0 0 0 0 0 0 0999 V2000\n 5.8129 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2338 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2338 -3.4094 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6547 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6547 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7171 -5.3780 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2004 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2628 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5924 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6258 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4342 -3.5669 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8507 -1.2047 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 14.9843 -5.8504 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 9 1 0\n 6 7 1 0\n 7 8 1 0\n 9 10 2 0\n 10 11 1 0\n 10 12 1 0\nM CHG 2 12 -1 13 -1\nA 1\nMeO2C\nA 5\nCO2Me\nA 8\nMeO2C\nA 11\nOMe\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.01950975487743872, 0.5760175420533526, 0.2866433216608304, 0.7653023145084401 ], "category_id": 1, "smiles": "[H]C(SC(CC(=O)OC)(SCC(OC)OC)C(=O)OC)C(=O)OC", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 3.4060 -2.3858 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8819 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8819 0.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3578 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6067 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3578 -4.1181 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6067 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6067 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9037 -5.8504 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4496 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7466 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0826 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2179 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9209 -4.2756 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6502 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 12 1 0\n 9 10 1 0\n 10 11 1 0\n 12 13 1 0\n 13 14 1 0\n 13 15 2 0\nA 1\nMeO\nA 8\nCO2Me\nA 11\nMeO2C\nA 14\nOMe\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.31915957978989495, 0.6331601148699828, 0.4112056028014007, 0.6693844244233822 ], "category_id": 2, "text": [ "NaOMe" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3891945972986493, 0.5571400849621444, 0.6568284142071036, 0.7530574774763051 ], "category_id": 1, "smiles": "COC(CSC(CC(=O)OC)(S/C=C(\\[O-])OC)C(=O)OC)OC", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 3.8552 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5074 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9480 -5.9291 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6002 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6002 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3886 -4.2756 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3886 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1769 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6175 0.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6349 -1.8346 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 9.2524 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0234 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5655 -4.4331 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3626 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 11 1 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 8 10 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 2 0\nM CHG 1 10 -1\nA 1\nMeO2C\nA 5\nCO2Me\nA 9\nOMe\nA 13\nOMe\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3891945972986493, 0.5571400849621444, 0.6568284142071036, 0.7530574774763051 ], "category_id": 1, "smiles": "COC(CSC(CC(=O)OC)(S/C=C(\\[O-])OC)C(=O)OC)OC", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 3.8552 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5074 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9480 -5.9291 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6002 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6002 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3886 -4.2756 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3886 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1769 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6175 0.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6349 -1.8346 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 9.2524 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0234 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5655 -4.4331 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3626 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 11 1 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 8 10 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 2 0\nM CHG 1 10 -1\nA 1\nMeO2C\nA 5\nCO2Me\nA 9\nOMe\nA 13\nOMe\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7328664332166083, 0.5739767358813301, 0.9579789894947474, 0.7510166713042826 ], "category_id": 1, "smiles": "COOC1(OC)CC(SCC(=O)OC)(C(OC)OC)SC1C(=O)OC", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 6.2351 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2351 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8041 -2.8583 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3152 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1908 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1551 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7684 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3016 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9950 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8127 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2351 -6.2441 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0750 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9950 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 11 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 11 12 1 0\n 12 13 1 0\nA 1\nCO2Me\nA 5\nMeO2C\nA 8\nOMe\nA 10\nOMe\nA 13\nCO2Me\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7328664332166083, 0.5739767358813301, 0.9579789894947474, 0.7510166713042826 ], "category_id": 1, "smiles": "COOC1(OC)CC(SCC(=O)OC)(C(OC)OC)SC1C(=O)OC", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 6.2351 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2351 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8041 -2.8583 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3152 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1908 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1551 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7684 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3016 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9950 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8127 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2351 -6.2441 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0750 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9950 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 11 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 11 12 1 0\n 12 13 1 0\nA 1\nCO2Me\nA 5\nMeO2C\nA 8\nOMe\nA 10\nOMe\nA 13\nCO2Me\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.03601800900450225, 0.817342871895014, 0.2656328164082041, 0.9923420011459441 ], "category_id": 1, "smiles": "*=C1(SCC(=O)OC)SC([H])(C(=O)OC)C(=O)C1[H].[I-]", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 2.3907 1.0037 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 -1.0037 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5241 0.5932 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.3442 2.2172 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n -0.2294 3.2209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5413 4.6881 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3907 0.0000 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 9 1 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\n 5 11 1 0\n 7 8 1 1\n 7 9 1 0\n 9 10 2 0\n 11 12 1 0\n 12 13 1 0\nM CHG 1 14 -1\nA 1\nCO2Me\nA 6\nMeO2C\nA 13\nCO2Me\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03601800900450225, 0.817342871895014, 0.2656328164082041, 0.9923420011459441 ], "category_id": 1, "smiles": "*=C1(SCC(=O)OC)SC([H])(C(=O)OC)C(=O)C1[H].[I-]", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 2.3907 1.0037 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 -1.0037 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5241 0.5932 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.3442 2.2172 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n -0.2294 3.2209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5413 4.6881 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3907 0.0000 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 9 1 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\n 5 11 1 0\n 7 8 1 1\n 7 9 1 0\n 9 10 2 0\n 11 12 1 0\n 12 13 1 0\nM CHG 1 14 -1\nA 1\nCO2Me\nA 6\nMeO2C\nA 13\nCO2Me\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.2366183091545773, 0.8887710879158018, 0.31615807903951976, 0.9300974128992576 ], "category_id": 2, "text": [ "OMe" ] } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.35417708854427216, 0.8545875845344247, 0.4607303651825913, 0.8948935064318694 ], "category_id": 2, "text": [ "HOMe" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.46823411705852924, 0.8244856934970929, 0.5507753876938469, 0.8586691968784698 ], "category_id": 1, "smiles": "[CH3].[Os]", "molfile": "\n RDKit 2D\n\n 2 0 0 0 0 0 0 0 0 0999 V2000\n 4.5472 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.2943 -4.6693 0.0000 Os 0 0 0 0 0 15 0 0 0 0 0 0\nA 1\nMe\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.51975987993997, 0.8285673058411378, 0.7018509254627313, 0.9765257533127696 ], "category_id": 1, "smiles": "[H]C1(C(=O)OC)S=C(C(OC)OC)C=C1=O", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 1.0037 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 -1.0037 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 S 0 0 0 0 0 3 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 8 9 2 0\nA 2\nCO2Me\nA 6\nMeO2C\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.51975987993997, 0.8285673058411378, 0.7018509254627313, 0.9765257533127696 ], "category_id": 1, "smiles": "[H]C1(C(=O)OC)S=C(C(OC)OC)C=C1=O", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 1.0037 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 -1.0037 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 S 0 0 0 0 0 3 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 8 9 2 0\nA 2\nCO2Me\nA 6\nMeO2C\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7923961980990495, 0.8198938796100422, 0.9859929964982491, 0.9673421255386683 ], "category_id": 1, "smiles": "COC(OC)c1cc(O)c(C(=O)OC)s1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 7.5591 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5591 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7743 -3.6457 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5092 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2493 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6089 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3438 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3386 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 7 8 1 0\nA 2\nCO2Me\nA 5\nMeO2C\nM END\n" } ] } ], "Fischer indole synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04452226113056528, 0.07680165494081594, 0.2016008004002001, 0.41936141745461397 ], "category_id": 1, "smiles": "[1*]C([1*])([H])/C([2*])=N\\Nc1ccccc1.[H]", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 5.9953 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9953 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1438 -1.2835 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9953 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8468 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 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2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 5.9687 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9687 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8395 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7103 -2.3858 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8395 -5.7717 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 5.9687 -6.8740 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0979 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3162 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4454 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4454 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3162 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0979 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\nM CHG 1 5 1\nM ISO 2 2 1 4 2\nA 2\nR1\nA 4\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.04452226113056528, 0.07680165494081594, 0.2016008004002001, 0.41936141745461397 ], "category_id": 1, "smiles": "[1*]C([1*])([H])/C([2*])=N\\Nc1ccccc1.[H]", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 5.9953 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9953 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1438 -1.2835 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9953 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8468 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6983 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8468 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9953 -6.6378 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1438 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2923 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4408 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4408 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2923 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1438 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2575 -8.1339 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 2 0\n 9 14 1 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\nM ISO 3 2 1 4 1 6 2\nA 2\nR1\nA 4\nR1\nA 6\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2706353176588294, 0.07680165494081594, 0.423711855927964, 0.4071706785751194 ], "category_id": 1, "smiles": "[1*]/C=C(\\[2*])[NH2+]Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 5.9687 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9687 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8395 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7103 -2.3858 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8395 -5.7717 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 5.9687 -6.8740 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0979 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3162 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4454 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4454 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3162 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0979 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\nM CHG 1 5 1\nM ISO 2 2 1 4 2\nA 2\nR1\nA 4\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.42821410705352675, 0.15116516210573294, 0.5957978989494748, 0.22918589093449834 ], "category_id": 2, "text": [ "[3,3]-sigmatropic" ] }, { "category": "[Txt]", "bbox": [ 0.43921960980490243, 0.2669771814609316, 0.5867933966983492, 0.3279308758584045 ], "category_id": 2, "text": [ "rearrangement" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.608304152076038, 0.05607739884567513, 0.7613806903451726, 0.448619190765401 ], "category_id": 1, "smiles": "[1*]C(C([2*])=[NH2+])C1([H])C=CC=CC1=N.[H]", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 2.4701 -8.2126 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 0.3743 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3743 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8713 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4432 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0151 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4432 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4432 -0.9685 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0151 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0151 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5870 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0840 -1.8346 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5870 -4.6693 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 1.8713 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 14 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 14 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 2 0\nM CHG 1 13 1\nM ISO 2 10 1 12 2\nA 10\nR1\nA 12\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.608304152076038, 0.05607739884567513, 0.7613806903451726, 0.448619190765401 ], "category_id": 1, "smiles": "[1*]C(C([2*])=[NH2+])C1([H])C=CC=CC1=N.[H]", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 2.4701 -8.2126 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 0.3743 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3743 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8713 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4432 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0151 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4432 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4432 -0.9685 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0151 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0151 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5870 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0840 -1.8346 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5870 -4.6693 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 1.8713 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 14 2 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 14 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 2 0\nM CHG 1 13 1\nM ISO 2 10 1 12 2\nA 10\nR1\nA 12\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.76088044022011, 0.19017552652011566, 0.9109554777388694, 0.2535673686934875 ], "category_id": 2, "text": [ "tautomerization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.04452226113056528, 0.6619571211565564, 0.20110055027513757, 1.003297809782405 ], "category_id": 1, "smiles": "[1*]C(C([2*])=N)c1ccccc1N", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 0.4443 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4443 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3105 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1766 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0427 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0427 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9089 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7750 -2.2283 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9089 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1766 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0427 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3105 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 12 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 2 0\n 10 11 1 0\n 10 12 2 0\nM ISO 2 6 1 8 2\nA 6\nR1\nA 8\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04452226113056528, 0.6619571211565564, 0.20110055027513757, 1.003297809782405 ], "category_id": 1, "smiles": "[1*]C(C([2*])=N)c1ccccc1N", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 0.4443 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4443 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3105 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1766 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0427 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0427 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9089 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7750 -2.2283 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9089 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1766 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0427 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3105 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 12 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 2 0\n 10 11 1 0\n 10 12 2 0\nM ISO 2 6 1 8 2\nA 6\nR1\nA 8\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.288144072036018, 0.6729287861481015, 0.4487243621810905, 0.9935452186788093 ], "category_id": 1, "smiles": "[1*]C1([H])C2=C(C=CC=C2)N([H])([H])C1([2*])N", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 1.2135 -2.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9635 -4.0247 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5838 -2.1155 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2135 -2.7256 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.9635 -4.0247 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5838 -2.1155 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -3.6073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0037 -4.7220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0037 -4.7220 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 13 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 1 0\n 13 14 1 0\n 13 15 1 0\nM ISO 2 3 1 14 2\nA 3\nR1\nA 14\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.288144072036018, 0.6729287861481015, 0.4487243621810905, 0.9935452186788093 ], "category_id": 1, "smiles": "[1*]C1([H])C2=C(C=CC=C2)N([H])([H])C1([2*])N", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 1.2135 -2.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9635 -4.0247 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5838 -2.1155 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2135 -2.7256 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.9635 -4.0247 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5838 -2.1155 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -3.6073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0037 -4.7220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0037 -4.7220 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 13 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 1 0\n 13 14 1 0\n 13 15 1 0\nM ISO 2 3 1 14 2\nA 3\nR1\nA 14\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5027513756878439, 0.6668334167083543, 0.6678339169584793, 0.9594111498162244 ], "category_id": 1, "smiles": "[1*]C1([H])c2ccccc2NC1([2*])N.[I-]", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 7.1725 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9332 -0.1024 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3250 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7817 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6082 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4347 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4347 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6082 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7817 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1725 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6940 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8674 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4327 -6.4016 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8017 -8.2913 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 11 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 1 0\nM CHG 1 14 -1\nM ISO 2 3 1 12 2\nA 3\nR1\nA 12\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5027513756878439, 0.6668334167083543, 0.6678339169584793, 0.9594111498162244 ], "category_id": 1, "smiles": "[1*]C1([H])c2ccccc2NC1([2*])N.[I-]", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 7.1725 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9332 -0.1024 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3250 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7817 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6082 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4347 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4347 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6082 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7817 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1725 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6940 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8674 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4327 -6.4016 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8017 -8.2913 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 11 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 1 0\nM CHG 1 14 -1\nM ISO 2 3 1 12 2\nA 3\nR1\nA 12\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7143571785892946, 0.735101554433524, 0.7633816908454227, 0.8131222832622893 ], "category_id": 2, "text": [ "NH3" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7748874437218609, 0.660738047268607, 0.9264632316158079, 0.9618492975921233 ], "category_id": 1, "smiles": "[1*]c1c([2*])[nH]c2ccccc12", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 0.6702 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6702 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6809 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6917 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8939 -6.5591 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2343 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5323 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8939 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5641 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6917 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6809 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 2 0\nM ISO 2 7 2 9 1\nA 7\nR2\nA 9\nR1\nM END\n" } ] } ], "Fischer oxazole synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04552276138069034, 0.1399799073090264, 0.18959479739869936, 0.35050087026984567 ], "category_id": 1, "smiles": "[1*]C(O)C#N", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 5.1774 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1180 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1774 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0014 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8254 -4.6693 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 3 0\nM ISO 1 2 1\nA 2\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.2786393196598299, 0.24689369478127493, 0.4137068534267134, 0.48496975760607575 ], "category_id": 1, "smiles": "[1*]C(O)C(=N)Cl", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 5.0197 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3622 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0197 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -7.6614 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9409 -3.2520 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\nM ISO 1 2 1\nA 2\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.34217108554277137, 0.08707411557018178, 0.4367183591795898, 0.2590179387214268 ], "category_id": 1, "smiles": "[2*]C([H])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.8705 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8705 -0.8110 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5276 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3097 -6.7165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 1 3 2\nA 3\nR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.2786393196598299, 0.24689369478127493, 0.4137068534267134, 0.48496975760607575 ], "category_id": 1, "smiles": "[1*]C(O)C(=N)Cl", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 5.0197 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3622 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0197 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4803 -7.6614 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9409 -3.2520 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\nM ISO 1 2 1\nA 2\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5242621310655328, 0.10470937948312999, 0.6873436718359179, 0.4541080457584164 ], "category_id": 1, "smiles": "[2*]C(/N=C(/Cl)C([7*])O)O[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 3.7206 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7206 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1030 -6.0866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4191 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4191 -8.1339 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0368 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0368 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7353 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4191 -1.9134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4191 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\nM ISO 2 2 7 8 2\nA 2\nR7\nA 8\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5242621310655328, 0.10470937948312999, 0.6873436718359179, 0.4541080457584164 ], "category_id": 1, "smiles": "[2*]C(/N=C(/Cl)C([7*])O)O[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 3.7206 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7206 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1030 -6.0866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4191 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4191 -8.1339 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0368 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0368 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7353 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4191 -1.9134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4191 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\nM ISO 2 2 7 8 2\nA 2\nR7\nA 8\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6988494247123562, 0.21052096296081924, 0.7518759379689844, 0.2832664266017306 ], "category_id": 2, "text": [ "HCI" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7873936968484242, 0.09038072755385956, 0.9649824912456229, 0.4353705778509089 ], "category_id": 1, "smiles": "[2*]/C(=N/C(Cl)=C(\\[7*])O)O[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 4.6310 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6310 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8499 -6.0866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4122 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4122 -8.0551 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1043 -5.0630 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1043 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8854 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4122 -1.9134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4122 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\nM ISO 2 2 7 8 2\nA 2\nR7\nA 8\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7873936968484242, 0.09038072755385956, 0.9649824912456229, 0.4353705778509089 ], "category_id": 1, "smiles": "[2*]/C(=N/C(Cl)=C(\\[7*])O)O[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 4.6310 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6310 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8499 -6.0866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4122 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4122 -8.0551 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1043 -5.0630 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1043 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8854 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4122 -1.9134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4122 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\nM ISO 2 2 7 8 2\nA 2\nR7\nA 8\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.11255627813906953, 0.7153303924689617, 0.1645822911455728, 0.7891780601044324 ], "category_id": 2, "text": [ "SN2" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.208104052026013, 0.6227452569259836, 0.3456728364182091, 0.9412822113536107 ], "category_id": 1, "smiles": "[1*]C1=C(Cl)[N+](C)C([2*])([H])O1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 9.1762 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1454 -4.4331 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 5.4154 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4154 -7.9764 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5351 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4291 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1368 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3180 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4240 -1.5984 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8667 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 1 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\nM CHG 1 2 1\nM RAD 1 2 2\nM ISO 2 6 1 10 2\nA 6\nR1\nA 10\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.208104052026013, 0.6227452569259836, 0.3456728364182091, 0.9412822113536107 ], "category_id": 1, "smiles": "[1*]C1=C(Cl)[N+](C)C([2*])([H])O1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 9.1762 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1454 -4.4331 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 5.4154 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4154 -7.9764 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5351 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4291 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1368 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3180 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4240 -1.5984 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8667 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 1 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\nM CHG 1 2 1\nM RAD 1 2 2\nM ISO 2 6 1 10 2\nA 6\nR1\nA 10\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3551775887943972, 0.7274546364091136, 0.4992496248124062, 0.795791284071788 ], "category_id": 2, "text": [ "isomerization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5292646323161581, 0.6062121970075948, 0.6458229114557279, 0.9192381314624254 ], "category_id": 1, "smiles": "[1*]C1([H])OC([2*])=NC1Cl", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 3.3500 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4173 -3.8031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4173 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3500 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4116 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1847 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7645 -4.0394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4116 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1847 -7.9764 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 1 0\nM ISO 2 3 1 6 2\nA 3\nR1\nA 6\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5292646323161581, 0.6062121970075948, 0.6458229114557279, 0.9192381314624254 ], "category_id": 1, "smiles": "[1*]C1([H])OC([2*])=NC1Cl", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 3.3500 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4173 -3.8031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4173 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3500 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4116 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1847 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7645 -4.0394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4116 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1847 -7.9764 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 1 0\nM ISO 2 3 1 6 2\nA 3\nR1\nA 6\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6728364182091046, 0.7175348004580803, 0.7908954477238619, 0.7858714481207546 ], "category_id": 2, "text": [ "elimination" ] }, { "category": "[Txt]", "bbox": [ 0.6878439219609805, 0.8156309559738546, 0.7678839419709855, 0.8828653996419696 ], "category_id": 2, "text": [ "HCI" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.8184092046023012, 0.6491981527954059, 0.9324662331165583, 0.9203403354569847 ], "category_id": 1, "smiles": "[1*]c1cnc([2*])o1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 4.0268 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6839 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0268 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5893 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4679 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2000 -4.8268 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5893 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\nM ISO 2 2 1 5 2\nA 2\nR1\nA 5\nR2\nM END\n" } ] } ], "Fleming\u2013Kumada oxidation.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.07653826913456728, 0.04573539945247814, 0.20910455227613806, 0.18463550149333768 ], "category_id": 1, "smiles": "*C([1*])[Si](C)(C)c1ccccc1.[H]", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 0.6001 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0861 -4.3543 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 6.0008 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0008 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0582 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1156 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1156 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0582 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9147 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9721 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8573 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2289 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3440 -6.4803 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 1 0\n 2 12 1 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 9 10 1 0\n 9 11 1 0\nM ISO 1 10 1\nA 10\nR1\nA 11\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2691345672836418, 0.07114395470385489, 0.32566283141570784, 0.10445739381121551 ], "category_id": 2, "text": [ "ipso" ] }, { "category": "[Txt]", "bbox": [ 0.24062031015507754, 0.12026716152318327, 0.3536768384192096, 0.1513220623859771 ], "category_id": 2, "text": [ "substitution" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.42471235617808906, 0.04234759208562792, 0.5582791395697849, 0.18011842500420405 ], "category_id": 1, "smiles": "*C([7*])[Si](C)(C)C1([H])=CC=CC=C1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 3.6132 -0.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 0.9642 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7981 1.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5377 3.4056 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2077 1.4153 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6849 2.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 1 0\n 2 13 1 0\n 3 4 1 0\n 3 5 1 0\n 3 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 10 11 1 0\n 10 12 1 0\nM ISO 1 11 7\nA 11\nR7\nA 12\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.42471235617808906, 0.04234759208562792, 0.5582791395697849, 0.18011842500420405 ], "category_id": 1, "smiles": "*C([7*])[Si](C)(C)C1([H])=CC=CC=C1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 3.6132 -0.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 0.9642 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7981 1.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5377 3.4056 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2077 1.4153 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6849 2.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 1 0\n 2 13 1 0\n 3 4 1 0\n 3 5 1 0\n 3 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 10 11 1 0\n 10 12 1 0\nM ISO 1 11 7\nA 11\nR7\nA 12\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6678339169584793, 0.05476955243074543, 0.7548774387193596, 0.15922694624196096 ], "category_id": 1, "smiles": "*C([1*])[Si](*)(C)C", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 8.9408 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0979 -2.6220 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 0.9686 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0979 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0036 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9686 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1527 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 7 1 0\n 4 5 1 0\n 4 6 1 0\nM ISO 1 5 1\nA 3\nX\nA 5\nR1\nA 6\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7783891945972986, 0.06098053260330419, 0.8824412206103052, 0.14228790940770977 ], "category_id": 1, "smiles": "*C(=O)OO[H]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 9.0605 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0605 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6628 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6049 -4.8268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1519 -0.8110 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5715 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 4 5 1 0\nA 2\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.08254127063531766, 0.354590504396991, 0.1455727863931966, 0.38903321262663504 ], "category_id": 1, "smiles": "[H][I-]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 1.6256 -2.6220 0.0000 I 0 0 0 0 0 1 0 0 0 0 0 0\n 13.0048 -2.6220 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nM CHG 1 1 -1\nM RAD 1 1 2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.1645822911455728, 0.3167599888004968, 0.33016508254127064, 0.44775520698537247 ], "category_id": 1, "smiles": "*C(=O)OO[Si](C)(C)C(*)*", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 0.6726 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3631 -4.0394 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 6.6142 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7442 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9863 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9863 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1162 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2510 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4931 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0089 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4663 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 1 0\n 2 11 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 1 0\n 8 10 1 0\nA 6\nAr\nA 9\nR\nA 10\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1645822911455728, 0.3167599888004968, 0.33016508254127064, 0.44775520698537247 ], "category_id": 1, "smiles": "*C(=O)OO[Si](C)(C)C(*)*", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 0.6726 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3631 -4.0394 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 6.6142 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7442 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9863 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9863 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1162 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2510 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4931 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0089 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4663 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 1 0\n 2 11 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 1 0\n 8 10 1 0\nA 6\nAr\nA 9\nR\nA 10\nR\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.3501750875437719, 0.34047464036844843, 0.4547273636818409, 0.38903321262663504 ], "category_id": 1, "smiles": "*", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 8.1568 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nArCO2\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.49074537268634316, 0.3303112182678977, 0.5907953976988495, 0.4528369180356478 ], "category_id": 1, "smiles": "*C([1*])O[Si](C)C", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.4381 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7745 -2.7795 0.0000 Si 0 0 0 0 0 3 0 0 0 0 0 0\n 5.0379 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0379 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7745 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2283 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7745 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\nM RAD 1 2 2\nM ISO 1 6 1\nA 5\nR\nA 6\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.49074537268634316, 0.3303112182678977, 0.5907953976988495, 0.4528369180356478 ], "category_id": 1, "smiles": "*C([1*])O[Si](C)C", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.4381 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7745 -2.7795 0.0000 Si 0 0 0 0 0 3 0 0 0 0 0 0\n 5.0379 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0379 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7745 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2283 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7745 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\nM RAD 1 2 2\nM ISO 1 6 1\nA 5\nR\nA 6\nR1\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.575287643821911, 0.2794941077651442, 0.6913456728364182, 0.35797831176384126 ], "category_id": 1, "smiles": "*C(=O)OO[H]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 10.3382 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2642 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6741 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2716 -4.9055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2716 -0.8898 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3382 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 4 5 1 0\nA 2\nAr\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7603801900950475, 0.30038558652738734, 0.888944472236118, 0.44831984154651416 ], "category_id": 1, "smiles": "*C(=O)OO[Si](C)(C)OC(*)*", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 4.5409 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6937 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4650 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5409 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6937 -3.5669 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 2.6937 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5409 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4650 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5430 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4650 -3.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4618 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6937 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 11 1 0\n 5 12 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\nA 2\nR\nA 3\nR\nA 9\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7603801900950475, 0.30038558652738734, 0.888944472236118, 0.44831984154651416 ], "category_id": 1, "smiles": "*C(=O)OO[Si](C)(C)OC(*)*", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 4.5409 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6937 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4650 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5409 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6937 -3.5669 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 2.6937 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5409 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4650 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5430 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4650 -3.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4618 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6937 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 11 1 0\n 5 12 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\nA 2\nR\nA 3\nR\nA 9\nAr\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.057028514257128564, 0.5719748104365476, 0.15957978989494748, 0.6188394790113092 ], "category_id": 2, "text": [ "ArCOz" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.17508754377188596, 0.6041589804216249, 0.29664832416208103, 0.7170858926499659 ], "category_id": 1, "smiles": "*C([7*])O[Si](C)OC", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 0.6712 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1096 -1.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1781 -1.8346 0.0000 Si 0 0 0 0 0 3 0 0 0 0 0 0\n 7.7672 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7672 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1781 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3563 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1781 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 8 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\nM RAD 1 3 2\nM ISO 1 7 7\nA 6\nR\nA 7\nR7\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2726363181590795, 0.53301502571777, 0.3891945972986493, 0.6120638642776088 ], "category_id": 1, "smiles": "*C(=O)OO[H]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 10.2074 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2642 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5432 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8790 -4.9843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8790 -0.8898 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2074 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 4 5 1 0\nA 2\nAr\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.47223611805902954, 0.5606821192137136, 0.6053026513256629, 0.7086163742328404 ], "category_id": 1, "smiles": "*C(=O)OO[Si](C)(OC)OC(*)*", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 0.5595 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7174 -5.7717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7174 -3.4882 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 2.7174 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7155 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6337 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8716 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6337 -3.5669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7155 -4.6693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7155 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7174 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6337 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3996 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 9 1 0\n 3 13 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\nA 7\nAr\nA 11\nR\nA 12\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.47223611805902954, 0.5606821192137136, 0.6053026513256629, 0.7086163742328404 ], "category_id": 1, "smiles": "*C(=O)OO[Si](C)(OC)OC(*)*", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 0.5595 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7174 -5.7717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7174 -3.4882 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 2.7174 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7155 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6337 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8716 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6337 -3.5669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7155 -4.6693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7155 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7174 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6337 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3996 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 9 1 0\n 3 13 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\nA 7\nAr\nA 11\nR\nA 12\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6738369184592297, 0.5956894620044992, 0.8014007003501751, 0.707487105110557 ], "category_id": 1, "smiles": "*C(*)O[Si](=O)(OC)OC", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 0.5028 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1176 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8330 -1.6772 0.0000 Si 0 0 0 0 0 5 0 0 0 0 0 0\n 8.2467 -3.2520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2467 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8330 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8615 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1176 -3.2520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1176 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9393 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 8 1 0\n 3 10 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 8 9 1 0\nM RAD 1 3 2\nA 6\nR\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6738369184592297, 0.5956894620044992, 0.8014007003501751, 0.707487105110557 ], "category_id": 1, "smiles": "*C(*)O[Si](=O)(OC)OC", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 0.5028 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1176 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8330 -1.6772 0.0000 Si 0 0 0 0 0 5 0 0 0 0 0 0\n 8.2467 -3.2520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2467 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8330 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8615 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1176 -3.2520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1176 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9393 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 8 1 0\n 3 10 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 8 9 1 0\nM RAD 1 3 2\nA 6\nR\nA 7\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7643821910955477, 0.5093003741498183, 0.8629314657328664, 0.5883492127096571 ], "category_id": 1, "smiles": "*C(=O)O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 7.7631 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7556 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2143 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7631 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nA 2\nAr\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.054527263631815905, 0.7978286348932299, 0.21560780390195097, 0.9773824253362922 ], "category_id": 1, "smiles": "*C(=O)O[Si](OC)(OC)OC(*)[1*].O", "molfile": "\n RDKit 2D\n\n 14 12 0 0 0 0 0 0 0 0999 V2000\n 5.1817 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5873 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"category": "[Txt]", "bbox": [ 0.23711855927963982, 0.8480811108348416, 0.3401700850425213, 0.8859116264313359 ], "category_id": 2, "text": [ "hydrolysis" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.36668334167083544, 0.7966993657709465, 0.4932466233116558, 0.9903690202425515 ], "category_id": 1, "smiles": "*C(*)O[Si](OC)(OC)OC(*)(O)O", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 0.3503 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8097 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3275 -4.7480 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 3.3275 -3.0945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7869 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4214 -3.0945 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9112 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6041 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8097 -5.6929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8097 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7869 -5.6929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7869 -7.3465 0.0000 C 0 0 0 0 0 0 0 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1.8097 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7869 -5.6929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7869 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3275 -8.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2463 -8.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 9 1 0\n 3 11 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 9 10 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 1 0\nA 6\nAr\nA 13\nR\nA 14\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5707853926963482, 0.8384823232954327, 0.6518259129564783, 0.935599467811806 ], "category_id": 1, "smiles": "*C(*)O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 4.2555 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1904 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3207 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2555 -2.3071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\nA 2\nR\nA 3\nR\nM END\n" } ] } ], "Friedel\u2013Crafts acylation reaction.png": [ { "reactants": [ { 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4.2033 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0046 -7.6614 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2033 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0046 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0046 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8060 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8060 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7275 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8476 -5.0630 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2818 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3303 -3.0945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 13 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 12 1 0\nA 10\nCOOH\nA 11\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.16258129064532267, 0.6677726187037182, 0.3566783391695848, 0.8988163095632324 ], "category_id": 1, "smiles": "" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.16258129064532267, 0.6677726187037182, 0.3566783391695848, 0.8988163095632324 ], "category_id": 1, "smiles": "" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.43921960980490243, 0.6048460850143382, 0.632816408204102, 0.948594015317518 ], "category_id": 1, "smiles": "*C1=Cc2ccccc2NC1([1*])O.O", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 1.9264 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3350 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3350 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0101 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6852 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3603 -3.5669 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9517 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9568 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8781 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9517 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6268 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3603 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6852 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0101 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 2 0\n 2 14 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 13 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\n 13 14 2 0\nM ISO 1 8 1\nA 8\nR1\nA 11\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.43921960980490243, 0.6048460850143382, 0.632816408204102, 0.948594015317518 ], "category_id": 1, "smiles": "*C1=Cc2ccccc2NC1([1*])O.O", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 1.9264 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3350 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3350 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0101 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6852 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3603 -3.5669 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9517 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9568 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8781 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9517 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6268 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3603 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6852 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0101 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 2 0\n 2 14 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 13 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\n 13 14 2 0\nM ISO 1 8 1\nA 8\nR1\nA 11\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7563781890945472, 0.6593198007454432, 0.935967983991996, 0.8518562097950384 ], "category_id": 1, "smiles": "*c1cc2ccccc2nc1[7*]", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 0.6812 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6812 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6787 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5399 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4010 -7.5039 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 12.3985 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2597 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.3985 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2597 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5373 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5399 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6787 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 12 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 11 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\n 11 12 2 0\nM ISO 1 7 7\nA 7\nR7\nA 9\nR\nM END\n" } ] } ], "Fries rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.09304652326163082, 0.09814864142027724, 0.1890945472736368, 0.3211481281766424 ], "category_id": 1, "smiles": "*C(=O)Oc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 2.0587 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7253 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7253 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0587 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0587 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7253 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4409 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7253 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3921 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3921 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 10 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 9 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 2 0\nA 7\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2651325662831416, 0.15443977399955386, 0.40070035017508754, 0.19918400758820967 ], "category_id": 2, "text": [ "complexation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4332166083041521, 0.050517683083966224, 0.5487743871935968, 0.32692157767195285 ], "category_id": 1, "smiles": "*O=C(*)OC1=CC=CC=C1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 3.8971 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 10 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 3\n 8 9 1 0\n 10 11 1 0\nA 7\nR\nA 9\nCl3Al\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4332166083041521, 0.050517683083966224, 0.5487743871935968, 0.32692157767195285 ], "category_id": 1, "smiles": "*O=C(*)OC1=CC=CC=C1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 3.8971 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 10 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 3\n 8 9 1 0\n 10 11 1 0\nA 7\nR\nA 9\nCl3Al\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5897948974487244, 0.14217119382201923, 0.6998499249624812, 0.18908047097141642 ], "category_id": 2, "text": [ "C-0 bond" ] }, { "category": "[Txt]", "bbox": [ 0.5727863931965983, 0.21145258776574435, 0.7138569284642321, 0.2547534589805725 ], "category_id": 2, "text": [ "fragmentation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7478739369684843, 0.061342900887673274, 0.8514257128564282, 0.27135212627959 ], "category_id": 1, "smiles": "*Oc1ccccc1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 2.1842 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3920 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3920 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1842 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1842 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9204 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9204 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9204 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 8 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 7 1 0\n 5 6 1 0\n 7 8 2 0\nA 6\nAlCl3\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.8979489744872436, 0.09814864142027724, 0.9299649824912456, 0.2525884154198311 ], "category_id": 1, "smiles": "*C#*", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 1.6505 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6505 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6505 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\nA 2\nR\nA 3\nOa\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.14057028514257128, 0.4041414646717298, 0.24412206103051526, 0.6141506900636465 ], "category_id": 1, "smiles": "*Oc1ccccc1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 2.1842 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3920 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3920 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1842 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1842 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9204 -1.3622 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9764 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9764 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 8 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 7 1 0\n 5 6 1 0\n 7 8 2 0\nA 6\nAlCl3\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.25662831415707854, 0.4690927714939721, 0.2891445722861431, 0.6249759078673536 ], "category_id": 1, "smiles": "*", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 1.5358 -1.5197 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\n189\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3871935967983992, 0.4207401319707473, 0.5102551275637819, 0.6249759078673536 ], "category_id": 1, "smiles": "*C(=O)C1([H])C=CC=CC1=O.[H]", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 2.2783 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4142 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4142 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2783 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2783 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1424 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1424 -3.3307 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0065 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8706 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0065 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1424 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5901 -1.0472 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 11 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 11 1 0\n 8 9 1 0\n 8 10 2 0\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3871935967983992, 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9088 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2158 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 12 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 10 11 1 0\n 10 12 2 0\nA 9\nR\nA 11\nCO2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6413206603301651, 0.6974689488695344, 0.7338669334667334, 0.779163701299348 ], "category_id": 1, "smiles": "*N", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 10.0984 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 18.7795 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nA 2\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7923961980990495, 0.614753012034348, 0.9439719859929965, 0.8506466096754349 ], "category_id": 1, "smiles": "OC(=O)c1ccccc1C(O)=O", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 0.6221 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6221 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2143 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3.9940 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9940 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3380 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7793 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7793 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3380 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 12 1 0\n 4 5 1 0\n 4 9 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 2 0\n 9 11 1 0\n 11 12 2 0\n 11 16 1 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 2 0\nA 2\nOMe\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.021010505252626314, 0.514335130143034, 0.18859429714857429, 0.957966509242147 ], "category_id": 1, "smiles": "COC(=O)c1ccccc1C(=O)NCC(C)=O", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 10.1501 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4861 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4861 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9054 -4.4331 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2414 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6607 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6607 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2414 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9054 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2414 0.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9967 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3328 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3328 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9967 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2414 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9054 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 16 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 15 2 0\n 6 7 2 0\n 6 14 1 0\n 7 8 1 0\n 7 11 1 0\n 8 9 1 0\n 8 10 2 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\nA 9\nOMe\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.2466233116558279, 0.5157214782027189, 0.4197098549274637, 0.9926252107342652 ], "category_id": 1, "smiles": "*C(=O)C1NC(=O)c2ccccc2C1(O)OC", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 5.7480 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7480 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9606 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0945 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5433 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5433 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0472 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6299 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6299 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0472 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9606 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9606 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3780 -5.6142 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3780 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7953 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2913 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7953 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 14 1 0\n 5 6 2 0\n 5 10 1 0\n 6 7 1 0\n 6 11 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 2 0\n 11 13 1 0\n 13 14 1 0\n 14 15 1 0\n 15 16 1 0\n 15 17 2 0\nA 2\nMe\nA 16\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2466233116558279, 0.5157214782027189, 0.4197098549274637, 0.9926252107342652 ], "category_id": 1, "smiles": "*C(=O)C1NC(=O)c2ccccc2C1(O)OC", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 5.7480 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7480 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9606 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0945 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5433 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5433 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0472 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6299 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6299 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0472 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9606 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9606 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3780 -5.6142 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3780 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7953 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2913 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7953 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 14 1 0\n 5 6 2 0\n 5 10 1 0\n 6 7 1 0\n 6 11 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 2 0\n 11 13 1 0\n 13 14 1 0\n 14 15 1 0\n 15 16 1 0\n 15 17 2 0\nA 2\nMe\nA 16\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.511255627813907, 0.5489938316351523, 0.6868434217108554, 0.957966509242147 ], "category_id": 1, "smiles": "*C(=O)C1NC(=O)c2ccccc2C1=O", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 0.3750 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1560 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7180 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4991 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2801 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 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3.9370 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7180 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4991 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2801 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0611 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2801 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4991 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7180 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7180 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1560 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3750 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7180 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 1 0\n 3 12 2 0\n 4 5 1 0\n 4 15 2 0\n 5 6 1 0\n 5 9 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 10 11 2 0\n 10 12 1 0\n 12 13 1 0\n 13 14 2 0\nA 7\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.775887943971986, 0.5392893952173591, 0.9489744872436218, 0.9510347689437234 ], "category_id": 1, "smiles": "*C(=O)c1nc(O)c2ccccc2c1O", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 0.3682 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1169 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8657 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6145 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6145 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3633 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1120 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8608 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1120 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3633 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6145 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6145 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8657 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1169 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3682 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 3 13 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 10 2 0\n 7 8 1 0\n 7 9 2 0\n 10 11 1 0\n 11 12 1 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6.2011 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2696 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3381 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4066 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4066 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3381 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2696 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1326 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2011 -2.2283 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0640 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9955 -3.3307 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0640 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 1 0\n 3 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\n 12 14 1 0\nM RAD 1 2 2\nA 13\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.00400200100050025, 0.4475756900189225, 0.23311655827913957, 0.6595852273963069 ], "category_id": 1, "smiles": 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3 4 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 2 0\n 11 16 1 0\n 11 17 2 0\n 14 15 1 0\n 15 16 1 0\n 15 17 2 0\nA 12\nR\nA 16\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.00400200100050025, 0.4475756900189225, 0.23311655827913957, 0.6595852273963069 ], "category_id": 1, "smiles": "*C12(=O)=O=C(*1)C[Si](C)(NC1=CC=CC=C1)C2", "molfile": "\n RDKit 2D\n\n 17 19 0 0 0 0 0 0 0 0999 V2000\n -3.3991 -0.7258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2500 0.2384 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n -3.3991 1.2026 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1386 2.6798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7291 3.1928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.4686 4.6700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6176 5.6342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.0272 5.1212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.2877 3.6440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -1.0607 0.0000 C 0 0 0 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0.4487837215709304, 0.7688844422211105, 0.6493169592042398 ], "category_id": 1, "smiles": "*C(=O)C(SC)C1([H])C=CC=CC1=N.[Ni]", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 4.7169 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7517 -0.8110 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7517 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7169 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7169 -1.9921 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7169 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7517 -7.9764 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7747 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8324 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8324 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7747 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7864 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7864 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7287 -3.0945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9249 -0.1024 0.0000 Ni 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 12 1 0\n 4 5 1 0\n 4 6 1 0\n 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"*C(O)(C[1*])C([H])(C#N)C(=O)O[2*]", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 4.7351 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8691 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3550 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8472 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9875 -4.2756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8503 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2335 -6.4016 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8472 -7.8189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4671 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.3362 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3393 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 2 0\nM ISO 1 2 1\nA 2\nR1\nA 4\nR\nA 7\nNC\nA 10\nOR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.057028514257128564, 0.43347496280543063, 0.1265632816408204, 0.4986291750062468 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.17108554277138568, 0.4135297958051808, 0.3366683341670835, 0.5657779039070882 ], "category_id": 1, "smiles": "*C(O)(C[1*])/C(C#N)=C(\\O)O[2*]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 4.2112 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4796 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5770 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9671 -1.5984 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1868 -4.3543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9427 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5770 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6743 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0401 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0401 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\nM ISO 1 2 1\nA 2\nR1\nA 4\nR\nA 7\nNC\nA 9\nOR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.17108554277138568, 0.4135297958051808, 0.3366683341670835, 0.5657779039070882 ], "category_id": 1, "smiles": "*C(O)(C[1*])/C(C#N)=C(\\O)O[2*]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 4.2112 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4796 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5770 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9671 -1.5984 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1868 -4.3543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9427 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5770 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6743 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0401 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0401 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\nM ISO 1 2 1\nA 2\nR1\nA 4\nR\nA 7\nNC\nA 9\nOR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.43721860930465234, 0.3749691396046977, 0.5737868934467234, 0.5637833872070631 ], "category_id": 1, "smiles": "*/C(=C(/C#N)C(=O)O[2*])C([H])[Rf]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 3.0870 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9693 -8.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2047 -8.0551 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 3.0870 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2047 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9693 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8515 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9693 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8515 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0870 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\nA 5\nR\nA 7\nCN\nA 9\nOR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.43721860930465234, 0.3749691396046977, 0.5737868934467234, 0.5637833872070631 ], "category_id": 1, "smiles": "*/C(=C(/C#N)C(=O)O[2*])C([H])[Rf]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 3.0870 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9693 -8.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2047 -8.0551 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 3.0870 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2047 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9693 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8515 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9693 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8515 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0870 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\nA 5\nR\nA 7\nCN\nA 9\nOR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6688344172086043, 0.32311170540404793, 0.8049024512256128, 0.5225633754065467 ], "category_id": 1, "smiles": "*/C=C(*)/C(C#N)=C(\\O)O[2*].C[S-]", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 2.8455 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0671 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8455 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0671 -3.7244 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5528 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3313 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5528 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3313 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8455 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3313 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1849 -7.8976 0.0000 S 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 7 9 1 0\n 10 11 1 0\nM CHG 1 11 -1\nA 2\nR\nA 4\nR\nA 6\nCN\nA 8\nOR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7453726863431716, 0.4873269137061053, 0.8449224612306153, 0.6256134049078378 ], "category_id": 1, "smiles": "S1SSSSSSS1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 1.1220 -2.5433 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1969 -5.5354 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2913 -7.6614 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2835 -7.6614 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3780 -5.5354 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3780 -2.5433 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2835 -0.3386 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2913 -0.3386 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 8 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6688344172086043, 0.32311170540404793, 0.8049024512256128, 0.5225633754065467 ], "category_id": 1, "smiles": "*/C=C(*)/C(C#N)=C(\\O)O[2*].C[S-]", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 2.8455 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0671 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8455 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0671 -3.7244 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5528 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3313 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5528 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3313 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8455 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3313 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1849 -7.8976 0.0000 S 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 7 9 1 0\n 10 11 1 0\nM CHG 1 11 -1\nA 2\nR\nA 4\nR\nA 6\nCN\nA 8\nOR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.03901950975487744, 0.7193556898090122, 0.20210105052526264, 0.9281151044116275 ], "category_id": 1, "smiles": "*/C(=C(/C#N)C(=O)O[2*])C([1*])SS[S-]", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 2.7835 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0643 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7835 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0643 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5028 -7.0315 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3858 -7.0315 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5144 -7.0315 0.0000 S 0 0 0 0 0 1 0 0 0 0 0 0\n 4.5028 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5028 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2220 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7835 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2220 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2688 -4.1181 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 8 9 1 0\n 8 12 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 3 0\nM CHG 1 7 -1\nM ISO 1 4 1\nA 2\nR\nA 4\nR1\nA 10\nOR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03901950975487744, 0.7193556898090122, 0.20210105052526264, 0.9281151044116275 ], "category_id": 1, "smiles": "*/C(=C(/C#N)C(=O)O[2*])C([1*])SS[S-]", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 2.7835 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0643 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7835 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0643 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5028 -7.0315 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3858 -7.0315 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5144 -7.0315 0.0000 S 0 0 0 0 0 1 0 0 0 0 0 0\n 4.5028 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5028 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2220 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7835 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2220 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2688 -4.1181 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 8 9 1 0\n 8 12 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 3 0\nM CHG 1 7 -1\nM ISO 1 4 1\nA 2\nR\nA 4\nR1\nA 10\nOR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.2061030515257629, 0.7286634344091287, 0.27613806903451726, 0.7944824855099534 ], "category_id": 1, "smiles": "[H][Br-]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nM CHG 1 2 -1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.34317158579289647, 0.6947566505087039, 0.542271135567784, 0.9281151044116275 ], "category_id": 1, "smiles": "*C1=C(C(=O)O)C(=N)S(SSSSSSS)C1(*)[H]", "molfile": "\n RDKit 2D\n\n 17 17 0 0 0 0 0 0 0 0999 V2000\n 2.8646 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1638 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5808 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4760 -6.1654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6856 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3712 -4.4331 0.0000 S 0 0 0 0 0 3 0 0 0 0 0 0\n 6.8930 -5.2992 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8930 -7.1102 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2358 -8.2126 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9367 -7.8189 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7424 -6.2441 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9367 -4.6693 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2358 -4.3543 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6398 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1616 -1.9134 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1179 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6703 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 16 2 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 14 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 14 15 2 0\n 14 16 1 0\n 16 17 1 0\nM RAD 1 6 2\nA 2\nR\nA 5\nR\nA 17\nHO2C\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.34317158579289647, 0.6947566505087039, 0.542271135567784, 0.9281151044116275 ], "category_id": 1, "smiles": "*C1=C(C(=O)O)C(=N)S(SSSSSSS)C1(*)[H]", "molfile": "\n RDKit 2D\n\n 17 17 0 0 0 0 0 0 0 0999 V2000\n 2.8646 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1638 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5808 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4760 -6.1654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6856 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3712 -4.4331 0.0000 S 0 0 0 0 0 3 0 0 0 0 0 0\n 6.8930 -5.2992 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8930 -7.1102 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2358 -8.2126 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9367 -7.8189 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7424 -6.2441 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9367 -4.6693 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2358 -4.3543 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6398 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1616 -1.9134 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1179 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6703 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 16 2 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 14 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 14 15 2 0\n 14 16 1 0\n 16 17 1 0\nM RAD 1 6 2\nA 2\nR\nA 5\nR\nA 17\nHO2C\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6028014007003502, 0.7346469845092037, 0.776888444222111, 0.8762576702109778 ], "category_id": 1, "smiles": "*c1c([1*])sc(N)c1C(=O)O[2*]", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 10.6597 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8617 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7607 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8431 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8068 -7.6614 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3666 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5412 -6.4803 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5225 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7245 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 8 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\nM ISO 1 7 1\nA 1\nCO2R2\nA 7\nR1\nA 9\nR\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.8039019509754878, 0.7798560297097701, 0.8394197098549274, 0.8277244305103698 ], "category_id": 2, "text": [ "S7" ] }, { "category": "[Idt]", "bbox": [ 0.8849424712356178, 0.7745373185097034, 0.9079539769884942, 0.8150924914102116 ], "category_id": 3, "text": [] } ] } ], "Glaser coupling.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.07803901950975488, 0.2064379152192919, 0.17158579289644824, 0.25629461927225294 ], "category_id": 1, "smiles": "*C", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 4.4882 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0\n 5 8 1 0\nA 1\n*\nA 2\nGu-\nA 3\n*\nA 4\nX\nA 5\nGu-\nA 6\n*\nA 7\n*\nA 8\nX\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2621310655327664, 0.08023813308523421, 0.3966983491745873, 0.398074621422861 ], "category_id": 1, "smiles": "**1(*)**(*)(*)*1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3301 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6082 0.6850 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0927 -4.1969 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3301 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6082 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8325 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7757 -4.1969 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 8 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nA 1\n*\nA 2\nGu-\nA 3\n*\nA 4\nX\nA 5\nGu-\nA 6\n*\nA 7\n*\nA 8\nX\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5767883941970986, 0.0895862650951644, 0.7418709354677339, 0.40196967642699855 ], "category_id": 1, "smiles": "*[Cu](*)(*)C#*", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 8.2143 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4331 -6.4803 0.0000 Cu 0 0 0 0 0 4 0 0 0 0 0 0\n 8.2143 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1344 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0051 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7115 -6.4803 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 3 0\nM RAD 1 2 2\nA 1\n*\nA 3\n*\nA 4\n*\nA 6\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5767883941970986, 0.0895862650951644, 0.7418709354677339, 0.40196967642699855 ], "category_id": 1, "smiles": "*[Cu](*)(*)C#*", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 8.2143 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4331 -6.4803 0.0000 Cu 0 0 0 0 0 4 0 0 0 0 0 0\n 8.2143 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1344 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0051 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7115 -6.4803 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 3 0\nM RAD 1 2 2\nA 1\n*\nA 3\n*\nA 4\n*\nA 6\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.2621310655327664, 0.08023813308523421, 0.3966983491745873, 0.398074621422861 ], "category_id": 1, "smiles": "**1(*)**(*)(*)*1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3301 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6082 0.6850 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0927 -4.1969 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3301 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6082 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8325 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7757 -4.1969 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 8 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nA 1\n*\nA 2\nGu-\nA 3\n*\nA 4\nX\nA 5\nGu-\nA 6\n*\nA 7\n*\nA 8\nX\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.07803901950975488, 0.2064379152192919, 0.17158579289644824, 0.25629461927225294 ], "category_id": 1, "smiles": "*C", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 4.4882 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 30.0000 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nA 1\nR\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.12556278139069535, 0.2905711033086637, 0.18409204602301152, 0.35522901637734755 ], "category_id": 2, "text": [ "Cu" ] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5767883941970986, 0.0895862650951644, 0.7418709354677339, 0.40196967642699855 ], "category_id": 1, "smiles": "*[Cu](*)(*)C#*", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 8.2143 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4331 -6.4803 0.0000 Cu 0 0 0 0 0 4 0 0 0 0 0 0\n 8.2143 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1344 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0051 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3.5260 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0260 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 1\n 2 10 1 0\n 2 13 1 0\n 4 5 1 0\n 4 6 3 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 10 11 3 0\n 11 12 1 0\n 13 14 3 0\n 14 15 1 0\nA 1\n*\nA 3\n*\nA 5\nR\nA 8\n*\nA 9\n*\nA 12\nR\nA 15\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.542271135567784, 0.657485284698424, 0.6133066533266633, 0.7198061647646253 ], "category_id": 2, "text": [ "Cu+2" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6513256628314157, 0.7018889117455924, 0.8604302151075538, 0.7610937478084837 ], "category_id": 1, "smiles": "*C#C*", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 13.4252 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4646 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 32.0472 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 51.1024 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\nA 2\nR\nA 4\nR\nM END\n" } ] } ], 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END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.43121560780390195, 0.04037467952726363, 0.624312156078039, 0.4389118387318659 ], "category_id": 1, "smiles": "CCOC(OCC)/C(=C(\\O)OCC)C(Nc1ccccc1)OCC", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 6.0507 -1.8346 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0426 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0426 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7289 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3564 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7693 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7693 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0830 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3968 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3968 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0830 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7289 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3160 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7289 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 12 13 1 0\n 12 14 1 0\nA 1\nEtO2C\nA 4\nOEt\nA 13\nOEt\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.14007003501750875, 0.07163249593546774, 0.3051525762881441, 0.37379138788144073 ], "category_id": 1, "smiles": "CCOC=C(OCC)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 4.9155 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1499 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2725 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2834 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2725 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1499 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1608 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 6 2 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\nA 1\nEtO\nA 4\nOEt\nA 7\nOEt\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.14007003501750875, 0.07163249593546774, 0.3051525762881441, 0.37379138788144073 ], "category_id": 1, "smiles": "CCOC=C(OCC)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 4.9155 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1499 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2725 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2834 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2725 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1499 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1608 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 6 2 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\nA 1\nEtO\nA 4\nOEt\nA 7\nOEt\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.43121560780390195, 0.04037467952726363, 0.624312156078039, 0.4389118387318659 ], "category_id": 1, "smiles": "CCOC(OCC)/C(=C(\\O)OCC)C(Nc1ccccc1)OCC", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 6.0507 -1.8346 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0426 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0426 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7289 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3564 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7693 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7693 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0830 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3968 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3968 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0830 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7289 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3160 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7289 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 12 13 1 0\n 12 14 1 0\nA 1\nEtO2C\nA 4\nOEt\nA 13\nOEt\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7573786893446723, 0.10549513037768883, 0.9479739869934968, 0.45454074693596797 ], "category_id": 1, "smiles": "CCOC(=O)C(=CNc1ccccc1)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 4.5675 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4614 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5754 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0210 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8034 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0210 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1272 -6.7953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2333 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3395 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4456 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4456 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3395 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2333 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\nA 1\nEtO\nA 5\nCO2Et\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.018509254627313655, 0.7228370044397199, 0.12406203101550775, 0.8035863634942471 ], "category_id": 2, "text": [ "cyclization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.1375687843921961, 0.622551510130065, 0.3306653326663332, 0.922105584042021 ], "category_id": 1, "smiles": "[H]C12C=CC=CC1=NC=C(C(=O)OCC)C2=O", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 9.5145 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6289 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2681 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2681 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -1.4409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7751 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5286 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5286 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7751 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2681 -7.8976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5145 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 2 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 11 1 0\n 7 8 1 0\n 7 12 2 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 12 13 1 0\nA 2\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1375687843921961, 0.622551510130065, 0.3306653326663332, 0.922105584042021 ], "category_id": 1, "smiles": "[H]C12C=CC=CC1=NC=C(C(=O)OCC)C2=O", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 9.5145 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6289 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2681 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2681 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -1.4409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7751 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5286 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5286 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7751 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2681 -7.8976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5145 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 2 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 11 1 0\n 7 8 1 0\n 7 12 2 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 12 13 1 0\nA 2\nCO2Et\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.34517258629314657, 0.7410707306778389, 0.49674837418709356, 0.8153080446473236 ], "category_id": 2, "text": [ "tautomerization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5067533766883442, 0.6069226019259629, 0.6983491745872936, 0.9064766758379189 ], "category_id": 1, "smiles": "CCOC(=O)c1cnc2ccccc2c1O.[I-]", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 9.3824 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6289 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3824 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1359 -7.8976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7751 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5286 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5286 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7751 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1359 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1359 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5933 -5.1417 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 11 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 10 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 1 0\nM CHG 1 13 -1\nA 2\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5067533766883442, 0.6069226019259629, 0.6983491745872936, 0.9064766758379189 ], "category_id": 1, "smiles": "CCOC(=O)c1cnc2ccccc2c1O.[I-]", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 9.3824 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6289 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3824 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1359 -7.8976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7751 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5286 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5286 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7751 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1359 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1359 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5933 -5.1417 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 11 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 10 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 1 0\nM CHG 1 13 -1\nA 2\nCO2Et\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7873936968484242, 0.5847816486368184, 0.9774887443721861, 0.9286176291270635 ], "category_id": 1, "smiles": "CCOC(=O)c1c[nH]c2ccccc2c1=O", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 8.1416 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9509 -2.2283 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2193 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2193 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2970 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2970 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3746 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4523 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4523 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3746 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2193 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1416 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 12 2 0\n 3 4 2 0\n 3 5 1 0\n 5 6 2 0\n 5 10 1 0\n 6 7 1 0\n 6 11 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 1 0\nA 2\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7873936968484242, 0.5847816486368184, 0.9774887443721861, 0.9286176291270635 ], "category_id": 1, "smiles": "CCOC(=O)c1c[nH]c2ccccc2c1=O", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 8.1416 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9509 -2.2283 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2193 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2193 -0.0236 0.0000 O 0 0 0 0 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7.1359 -7.8976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0216 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7751 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5286 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5286 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7751 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1359 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1359 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5933 -5.1417 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 11 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 10 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 1 0\nM CHG 1 13 -1\nA 2\nCO2Et\nM END\n" } ] } ], "Grignard reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.25962981490745374, 0.18568745911417248, 0.3631815907953977, 0.3344426059183438 ], "category_id": 1, "smiles": "[1*]C([2*])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.8154 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1248 -6.9528 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1248 -2.8583 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0650 -4.9843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.2831415707853927, 0.3385461961750106, 0.3691845922961481, 0.45549851849001427 ], "category_id": 2, "text": [ "R-MgX", "68" ] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5062531265632816, 0.21236079578250663, 0.6258129064532266, 0.38060799630584524 ], "category_id": 1, "smiles": "*[Mg]O=C(*)(*)[2*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.3481 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 2 3\n 5 6 1 0\nM ISO 1 3 2\nA 2\nR\nA 3\nR2\nA 4\nR\nA 6\nMgX\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5062531265632816, 0.21236079578250663, 0.6258129064532266, 0.38060799630584524 ], "category_id": 1, "smiles": "*[Mg]O=C(*)(*)[2*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.3481 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 2 3\n 5 6 1 0\nM ISO 1 3 2\nA 2\nR\nA 3\nR2\nA 4\nR\nA 6\nMgX\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7673836918459229, 0.22364566898834032, 0.894447223611806, 0.38471158656251203 ], "category_id": 1, "smiles": "*[Mg]OC(*)(*)[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 5.0814 -4.5906 0.0000 C 0 0 0 0 0 0 0 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0.28414207103551775, 0.7854583595770251 ], "category_id": 2, "text": [ "NH3" ] } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.3021510755377689, 0.6276756685769481, 0.3796898449224612, 0.7278734358543693 ], "category_id": 1, "smiles": "C[I-].O", "molfile": "\n RDKit 2D\n\n 3 1 0 0 0 0 0 0 0 0999 V2000\n 1.2563 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7459 -5.6929 0.0000 I 0 0 0 0 0 1 0 0 0 0 0 0\n 11.0272 -5.6929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nM CHG 1 2 -1\nM RAD 1 2 2\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3871935967983992, 0.5770009357010111, 0.5282641320660331, 0.8925663177011648 ], "category_id": 1, "smiles": "*C(=O)C/C(*)=C(/C#N)C(N)=O.[I-]", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 2.9168 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9168 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1343 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9168 -7.3465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6993 -1.9921 0.0000 C 0 0 0 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1967 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8506 -8.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3461 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3167 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1877 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6220 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6015 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7305 -5.2992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2644 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6603 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3142 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2350 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 14 1 0\n 2 18 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 13 2 0\n 6 7 1 0\n 6 12 1 0\n 7 10 1 0\n 10 11 1 0\n 11 12 1 0\n 14 15 2 0\n 14 16 1 0\n 16 17 1 0\n 17 18 1 0\n 18 19 2 0\n 7 8 1 6\n 7 9 1 1\nA 8\nCO2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.23911955977988994, 0.44232166334423495, 0.35567783891945975, 0.5079997285074699 ], "category_id": 2, "text": [ "catalytic", "asymmetric" ] }, { "category": "[Txt]", "bbox": [ 0.22961480740370185, 0.5287754429978808, 0.3661830915457729, 0.5656355816099005 ], "category_id": 2, "text": [ "enamine aldol" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3871935967983992, 0.35787843670579006, 0.5877938969484743, 0.6527595456019467 ], "category_id": 1, "smiles": "[H][N+]12(CCCC1C(O)=O)[H]1[N+]345C6CC[CH]37*[CH]3(C(O)=O)CCC[N+]16378C4(=C)CCC1(C)C34=O=C13(=O=4)[CH]258[O-]", "molfile": "\n RDKit 2D\n\n 32 44 0 0 0 0 0 0 0 0999 V2000\n -3.8757 4.6471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.7610 3.6434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.8452 2.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7107 1.1128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4589 0.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 N 0 0 0 0 0 7 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 5 0 0 0 0 0 0\n 1.6378 2.0523 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7114 0.4093 0.0000 H 0 0 0 0 0 3 0 0 0 0 0 0\n -0.2358 0.6787 0.0000 N 0 0 0 0 0 5 0 0 0 0 0 0\n -1.7354 0.6435 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1795 1.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7813 2.5496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0894 -0.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2365 -1.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.2006 -0.8208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.9224 1.7131 0.0000 N 0 0 0 0 0 5 0 0 0 0 0 0\n -1.4958 2.1766 0.0000 C 0 0 0 0 0 5 0 0 0 0 0 0\n -0.0692 2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.4958 3.6766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.9224 4.1401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.8041 2.9266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5052 2.1544 0.0000 C 0 0 0 0 0 6 0 0 0 0 0 0\n -1.9521 2.5499 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n -1.2746 3.4420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3570 4.6286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8434 4.8300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3570 4.6286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.9585 0.3201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 6\n 2 3 1 0\n 2 28 1 0\n 2 30 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 20 1 0\n 5 32 2 0\n 6 7 1 0\n 6 11 1 0\n 6 12 1 0\n 6 21 1 0\n 6 25 1 0\n 6 26 1 6\n 7 8 1 6\n 7 9 1 0\n 7 22 1 6\n 9 10 1 0\n 10 11 1 0\n 12 13 1 0\n 12 20 1 0\n 13 14 1 0\n 13 15 1 0\n 13 19 1 0\n 13 26 1 0\n 15 16 1 6\n 15 17 1 0\n 17 18 1 0\n 18 19 1 0\n 20 21 1 0\n 20 25 1 0\n 20 26 1 6\n 21 22 1 6\n 21 23 1 0\n 23 24 1 0\n 24 25 1 0\n 26 27 1 6\n 26 28 1 0\n 28 29 2 0\n 28 30 1 0\n 28 31 2 0\n 29 30 2 0\n 30 31 2 0\nM CHG 4 6 1 13 1 20 1 27 -1\nA 8\nCO2\nA 16\nCO2\nA 22\nCO2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3871935967983992, 0.35787843670579006, 0.5877938969484743, 0.6527595456019467 ], "category_id": 1, "smiles": "[H][N+]12(CCCC1C(O)=O)[H]1[N+]345C6CC[CH]37*[CH]3(C(O)=O)CCC[N+]16378C4(=C)CCC1(C)C34=O=C13(=O=4)[CH]258[O-]", "molfile": "\n RDKit 2D\n\n 32 44 0 0 0 0 0 0 0 0999 V2000\n -3.8757 4.6471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.7610 3.6434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.8452 2.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7107 1.1128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4589 0.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 N 0 0 0 0 0 7 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 5 0 0 0 0 0 0\n 1.6378 2.0523 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7114 0.4093 0.0000 H 0 0 0 0 0 3 0 0 0 0 0 0\n -0.2358 0.6787 0.0000 N 0 0 0 0 0 5 0 0 0 0 0 0\n -1.7354 0.6435 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1795 1.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7813 2.5496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0894 -0.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2365 -1.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.2006 -0.8208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.9224 1.7131 0.0000 N 0 0 0 0 0 5 0 0 0 0 0 0\n -1.4958 2.1766 0.0000 C 0 0 0 0 0 5 0 0 0 0 0 0\n -0.0692 2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.4958 3.6766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.9224 4.1401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.8041 2.9266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5052 2.1544 0.0000 C 0 0 0 0 0 6 0 0 0 0 0 0\n -1.9521 2.5499 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n -1.2746 3.4420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3570 4.6286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8434 4.8300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3570 4.6286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.9585 0.3201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 6\n 2 3 1 0\n 2 28 1 0\n 2 30 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 20 1 0\n 5 32 2 0\n 6 7 1 0\n 6 11 1 0\n 6 12 1 0\n 6 21 1 0\n 6 25 1 0\n 6 26 1 6\n 7 8 1 6\n 7 9 1 0\n 7 22 1 6\n 9 10 1 0\n 10 11 1 0\n 12 13 1 0\n 12 20 1 0\n 13 14 1 0\n 13 15 1 0\n 13 19 1 0\n 13 26 1 0\n 15 16 1 6\n 15 17 1 0\n 17 18 1 0\n 18 19 1 0\n 20 21 1 0\n 20 25 1 0\n 20 26 1 6\n 21 22 1 6\n 21 23 1 0\n 23 24 1 0\n 24 25 1 0\n 26 27 1 6\n 26 28 1 0\n 28 29 2 0\n 28 30 1 0\n 28 31 2 0\n 29 30 2 0\n 30 31 2 0\nM CHG 4 6 1 13 1 20 1 27 -1\nA 8\nCO2\nA 16\nCO2\nA 22\nCO2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6053026513256629, 0.3940683909794093, 0.8034017008504252, 0.6071870105907226 ], "category_id": 1, "smiles": "CC12CCC(=N3CCCC3C(O)=O)CC1(O)CCC2=O.O", "molfile": "\n RDKit 2D\n\n 19 20 0 0 0 0 0 0 0 0999 V2000\n -2.2418 -1.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2135 -2.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6401 -3.1891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -3.6073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2135 -2.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2418 -1.4558 0.0000 O 0 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4.3037 0.0000 0.0000 O 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 6\n 2 3 1 0\n 2 7 1 0\n 2 18 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 1\n 7 9 1 0\n 9 10 1 0\n 10 11 2 3\n 10 17 1 0\n 11 12 1 0\n 11 16 1 0\n 12 13 1 6\n 12 14 1 0\n 14 15 1 0\n 15 16 1 0\n 17 18 1 0\nA 13\nCO2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8194097048524263, 0.4543849814354413, 0.9239619809904952, 0.4979469634314645 ], "category_id": 2, "text": [ "hydrolysis" ] }, { "category": "[Txt]", "bbox": [ 0.8019009504752376, 0.5153717562298737, 0.9439719859929965, 0.5549126321954947 ], "category_id": 2, "text": [ "of iminium salt" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.08754377188594298, 0.751276643346799, 0.2696348174087044, 0.9684163689885144 ], "category_id": 1, "smiles": "C[C@]12CCC(O)(N3CCC[C@H]3C(O)=O)C[C@@]1(O)CCC2=O", "molfile": "\n RDKit 2D\n\n 19 21 0 0 0 0 0 0 0 0999 V2000\n 8.2325 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2325 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5506 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8687 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8687 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1868 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1868 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1868 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6916 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5049 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3541 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4163 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5506 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2325 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2325 -6.0079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0915 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2422 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0915 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7111 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 14 1 0\n 2 18 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 13 1 0\n 7 8 1 0\n 7 12 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 13 14 1 0\n 14 16 1 0\n 16 17 1 0\n 17 18 1 0\n 18 19 2 0\n 2 1 1 1\n 8 9 1 6\n 14 15 1 1\nA 9\nCO2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.08754377188594298, 0.751276643346799, 0.2696348174087044, 0.9684163689885144 ], "category_id": 1, "smiles": "C[C@]12CCC(O)(N3CCC[C@H]3C(O)=O)C[C@@]1(O)CCC2=O", "molfile": "\n RDKit 2D\n\n 19 21 0 0 0 0 0 0 0 0999 V2000\n 8.2325 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2325 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5506 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8687 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8687 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1868 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1868 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1868 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6916 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5049 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3541 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4163 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5506 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2325 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2325 -6.0079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0915 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2422 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0915 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7111 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 14 1 0\n 2 18 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 13 1 0\n 7 8 1 0\n 7 12 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 13 14 1 0\n 14 16 1 0\n 16 17 1 0\n 17 18 1 0\n 18 19 2 0\n 2 1 1 1\n 8 9 1 6\n 14 15 1 1\nA 9\nCO2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3371685842921461, 0.7224587167955838, 0.4807403701850925, 0.9080997785324824 ], "category_id": 1, "smiles": "[H]C1C(=O)CC[C@]2(C)C(=O)CC[C@]12O", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 6.6107 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6107 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6511 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3040 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8753 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6511 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6107 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6107 -6.9528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7336 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7336 -8.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8565 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9794 -5.8504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8565 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7336 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 7 1 0\n 2 14 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 2 0\n 11 13 1 0\n 13 14 1 0\n 2 1 1 1\n 7 8 1 1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3371685842921461, 0.7224587167955838, 0.4807403701850925, 0.9080997785324824 ], "category_id": 1, "smiles": "[H]C1C(=O)CC[C@]2(C)C(=O)CC[C@]12O", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 6.6107 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6107 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6511 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3040 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8753 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6511 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6107 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6107 -6.9528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7336 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7336 -8.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8565 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9794 -5.8504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8565 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7336 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 7 1 0\n 2 14 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 2 0\n 11 13 1 0\n 13 14 1 0\n 2 1 1 1\n 7 8 1 1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5287643821910956, 0.7372027722403917, 0.6768384192096047, 0.9067594098556816 ], "category_id": 1, "smiles": "C[C@]12CCC([O-])=C[C@@]1(O)CCC2=O", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 7.5931 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5931 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0929 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6854 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6854 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -7.3465 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 5.0929 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5931 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5931 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0006 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2970 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0006 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6488 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 8 1 0\n 2 12 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 2 0\n 2 1 1 1\n 8 9 1 1\nM CHG 1 6 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5287643821910956, 0.7372027722403917, 0.6768384192096047, 0.9067594098556816 ], "category_id": 1, "smiles": "C[C@]12CCC([O-])=C[C@@]1(O)CCC2=O", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 7.5931 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5931 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0929 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6854 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6854 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -7.3465 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 5.0929 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5931 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5931 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0006 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2970 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0006 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6488 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 8 1 0\n 2 12 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 2 0\n 2 1 1 1\n 8 9 1 1\nM CHG 1 6 -1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6998499249624812, 0.798189547034824, 0.7613806903451726, 0.8390707916772456 ], "category_id": 2, "text": [ "ElcB" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7703851925962981, 0.7606592240844041, 0.9119559779889945, 0.9080997785324824 ], "category_id": 1, "smiles": "C[C@]12CCC(=O)C=C1CCC2=O", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 8.3522 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3522 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8986 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6116 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.3246 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8986 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3522 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1114 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8705 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5278 -7.7402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8705 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1114 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 2 7 1 0\n 2 12 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 3\n 8 9 1 0\n 9 10 2 0\n 9 11 1 0\n 11 12 1 0\n 2 1 1 1\nM END\n" } ] } ], "Haller\u2013Bauer reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.021010505252626314, 0.0, 0.18359179589794897, 0.9972190640774934 ], "category_id": 1, "smiles": "*C(*)([2*])C(=O)C([3*])([4*])[5*].N", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 2.8148 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8148 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0947 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0947 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6132 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3334 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1317 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3334 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1317 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6132 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1934 -7.8976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 10 2 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\nM ISO 4 2 2 7 5 8 3 9 4\nA 2\nR2\nA 3\nR\nA 4\nR\nA 7\nR5\nA 8\nR3\nA 9\nR4\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.263631815907954, 0.0, 0.42471235617808906, 0.812324343990177 ], "category_id": 1, "smiles": "*C([1*])([2*])C(N)O.[3*]C([4*])[5*]", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 3.6370 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6370 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3399 -4.1181 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3399 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8383 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0825 -1.9921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4984 -1.9921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0396 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0396 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3367 -4.1181 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3367 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM ISO 5 2 2 4 1 9 3 10 5 11 4\nA 2\nR2\nA 3\nR\nA 4\nR1\nA 9\nR3\nA 10\nR5\nA 11\nR4\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.263631815907954, 0.0, 0.42471235617808906, 0.812324343990177 ], "category_id": 1, "smiles": "*C([1*])([2*])C(N)O.[3*]C([4*])[5*]", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 3.6370 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6370 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3399 -4.1181 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3399 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8383 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0825 -1.9921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4984 -1.9921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0396 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0396 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3367 -4.1181 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3367 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM ISO 5 2 2 4 1 9 3 10 5 11 4\nA 2\nR2\nA 3\nR\nA 4\nR1\nA 9\nR3\nA 10\nR5\nA 11\nR4\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.021010505252626314, 0.0, 0.18359179589794897, 0.9972190640774934 ], "category_id": 1, "smiles": "*C(*)([2*])C(=O)C([3*])([4*])[5*].N", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 2.8148 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8148 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0947 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0947 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6132 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3334 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1317 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3334 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1317 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6132 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1934 -7.8976 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 10 2 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\nM ISO 4 2 2 7 5 8 3 9 4\nA 2\nR2\nA 3\nR\nA 4\nR\nA 7\nR5\nA 8\nR3\nA 9\nR4\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.263631815907954, 0.0, 0.42471235617808906, 0.812324343990177 ], "category_id": 1, "smiles": "*C([1*])([2*])C(N)O.[3*]C([4*])[5*]", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 3.6370 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6370 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3399 -4.1181 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3399 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8383 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0825 -1.9921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4984 -1.9921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0396 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0396 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3367 -4.1181 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3367 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM ISO 5 2 2 4 1 9 3 10 5 11 4\nA 2\nR2\nA 3\nR\nA 4\nR1\nA 9\nR3\nA 10\nR5\nA 11\nR4\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.512256128064032, 0.10002501250625313, 0.6618309154577289, 0.806262222020101 ], "category_id": 1, "smiles": "*C(*)([2*])C(N)=O", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 4.1462 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1462 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6180 -3.1732 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6180 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6744 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2026 -4.7480 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6744 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 2 0\nM ISO 1 2 2\nA 2\nR2\nA 3\nR\nA 4\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 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0.12779037602424906, 0.8554277138569285, 0.16089970072144086 ], "category_id": 2, "text": [ "condensation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.17158579289644824, 0.22769921546138924, 0.32716358179089544, 0.36884949443362797 ], "category_id": 1, "smiles": "*C(O)C([H])(C([1*])=O)C(=O)OCC.[Ni]", "molfile": "\n RDKit 2D\n\n 10 8 0 0 0 0 0 0 0 0999 V2000\n 5.3050 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7072 -4.1969 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5061 -2.1496 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3050 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4069 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1029 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1029 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0009 -4.1969 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1029 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5107 -0.1024 0.0000 Ni 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 7 1 0\n 4 5 1 0\n 4 6 2 0\n 7 8 1 0\n 7 9 1 0\nM ISO 1 5 1\nA 2\nCO2Et\nA 5\nR1\nA 8\nR\nM 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4.1804 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3064 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\nM ISO 1 4 1\nA 2\nCO2Et\nA 4\nR1\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.18509254627313657, 0.386275454800571, 0.31115557778889447, 0.49315467838448845 ], "category_id": 1, "smiles": "I.[1*]C(=O)CC(=O)OCC", "molfile": "\n RDKit 2D\n\n 6 4 0 0 0 0 0 0 0 0999 V2000\n 4.2095 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0158 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2095 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0158 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4032 -7.4252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4126 -3.4094 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 2 0\nM ISO 1 4 1\nA 2\nCO2Et\nA 4\nR1\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.2941470735367684, 0.4188039141521981, 0.34967483741870936, 0.45481756557721376 ], "category_id": 2, "text": [ ":NH3" ] } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3751875937968984, 0.4083483379320322, 0.471735867933967, 0.44145766262922403 ], "category_id": 2, "text": [ "enamine" ] }, { "category": "[Txt]", "bbox": [ 0.3751875937968984, 0.4583027576506023, 0.4752376188094047, 0.4908312170022293 ], "category_id": 2, "text": [ "formation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.503751875937969, 0.386275454800571, 0.6498249124562281, 0.5129041001336906 ], "category_id": 1, "smiles": "[1*]C(N)([O-])CC(=O)OCC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 5.5373 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9865 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5373 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0930 -6.0079 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8751 -5.2992 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 4.7919 -7.4252 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\nM CHG 1 5 -1\nM ISO 1 4 1\nA 2\nCO2Et\nA 4\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.503751875937969, 0.386275454800571, 0.6498249124562281, 0.5129041001336906 ], "category_id": 1, "smiles": "[1*]C(N)([O-])CC(=O)OCC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 5.5373 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9865 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5373 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0930 -6.0079 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8751 -5.2992 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 4.7919 -7.4252 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\nM CHG 1 5 -1\nM ISO 1 4 1\nA 2\nCO2Et\nA 4\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6753376688344173, 0.40776747258646745, 0.7488744372186094, 0.4478471814304365 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.08854427213606804, 0.5924826524760638, 0.24012006003001501, 0.7196921631547482 ], "category_id": 1, "smiles": "[1*]C(=[NH2+])C([H])C(=O)OCC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 5.6782 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0805 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2759 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6782 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0805 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2759 -6.0866 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\nM CHG 1 6 1\nM ISO 1 5 1\nA 2\nCO2Et\nA 5\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.08854427213606804, 0.5924826524760638, 0.24012006003001501, 0.7196921631547482 ], "category_id": 1, "smiles": "[1*]C(=[NH2+])C([H])C(=O)OCC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 5.6782 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0805 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2759 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6782 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0805 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2759 -6.0866 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\nM CHG 1 6 1\nM ISO 1 5 1\nA 2\nCO2Et\nA 5\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.29664832416208103, 0.5675054426167788, 0.5642821410705353, 0.730147739374914 ], "category_id": 1, "smiles": "*/C=C(\\C(OCC)OCC)C(=O)[Rf].CCOC(=O)C=C(N)[Rf]", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 19.1852 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0128 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0128 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1852 -8.3701 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 12.8405 -8.3701 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -7.1102 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 3.1724 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3447 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1724 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3447 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3447 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 6 7 1 0\n 7 8 2 0\n 7 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\nA 1\nCO2Et\nA 10\nEtO2C\nA 12\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.29664832416208103, 0.5675054426167788, 0.5642821410705353, 0.730147739374914 ], "category_id": 1, "smiles": "*/C=C(\\C(OCC)OCC)C(=O)[Rf].CCOC(=O)C=C(N)[Rf]", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 19.1852 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0128 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0128 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1852 -8.3701 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 12.8405 -8.3701 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -7.1102 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 3.1724 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3447 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1724 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3447 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3447 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 6 7 1 0\n 7 8 2 0\n 7 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\nA 1\nCO2Et\nA 10\nEtO2C\nA 12\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5777888944472236, 0.6058425554240534, 0.6688344172086043, 0.6435988028857634 ], "category_id": 2, "text": [ "Michael" ] }, { "category": "[Txt]", "bbox": [ 0.5777888944472236, 0.6604438979071416, 0.6678339169584793, 0.6952958186410279 ], "category_id": 2, "text": [ "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6973486743371686, 0.5558881357054835, 0.9249624812406203, 0.7493162957785513 ], "category_id": 1, "smiles": "*C(/C(C(OCC)OCC)=C(\\[O-])[Rf])C([H])(C(=O)OCC)/C([Rf])=N/[H].CC.[H][NH2+]", "molfile": "\n RDKit 2D\n\n 18 15 0 0 0 0 0 0 0 0999 V2000\n 3.4430 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0570 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0570 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9177 -6.2441 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 3.6582 -5.9291 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 6.6709 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6709 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2848 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7912 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2848 -1.0472 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2848 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7912 -5.5354 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 7.7469 -6.4016 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7469 -8.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2975 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3418 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1962 -0.1811 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2595 -0.1811 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 6 1 0\n 3 4 1 0\n 3 5 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\n 11 12 1 0\n 11 13 2 0\n 13 14 1 0\n 15 16 1 0\n 17 18 1 0\nM CHG 2 4 -1 18 1\nM RAD 1 18 2\nA 1\nEtO2C\nA 7\nR\nA 9\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6973486743371686, 0.5558881357054835, 0.9249624812406203, 0.7493162957785513 ], "category_id": 1, "smiles": "*C(/C(C(OCC)OCC)=C(\\[O-])[Rf])C([H])(C(=O)OCC)/C([Rf])=N/[H].CC.[H][NH2+]", "molfile": "\n RDKit 2D\n\n 18 15 0 0 0 0 0 0 0 0999 V2000\n 3.4430 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0570 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0570 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9177 -6.2441 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 3.6582 -5.9291 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 6.6709 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6709 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2848 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7912 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2848 -1.0472 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2848 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7912 -5.5354 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 7.7469 -6.4016 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7469 -8.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2975 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3418 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1962 -0.1811 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2595 -0.1811 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 6 1 0\n 3 4 1 0\n 3 5 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\n 11 12 1 0\n 11 13 2 0\n 13 14 1 0\n 15 16 1 0\n 17 18 1 0\nM CHG 2 4 -1 18 1\nM RAD 1 18 2\nA 1\nEtO2C\nA 7\nR\nA 9\nCO2Et\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.0, 0.8474825391789972, 0.15407703851925963, 0.8858196519862719 ], "category_id": 2, "text": [ "tautomerization" ] }, { "category": "[Txt]", "bbox": [ 0.12356178089044523, 0.918348111337899, 0.20910455227613806, 0.9584278201818679 ], "category_id": 2, "text": [ "HzN-H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.16708354177088544, 0.7841682165124375, 0.39269634817408705, 0.9462296479250079 ], "category_id": 1, "smiles": "*C(/C(C(=O)OCC)=C(/[1*])N)C(C([1*])=O)C(=O)OCC.[H][I-]", "molfile": "\n RDKit 2D\n\n 14 12 0 0 0 0 0 0 0 0999 V2000\n 0.5072 -8.1339 0.0000 I 0 0 0 0 0 1 0 0 0 0 0 0\n 2.2823 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4378 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3397 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3397 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3397 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8182 -6.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2417 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2417 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0168 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9187 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0168 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9187 -6.3228 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5096 -7.4252 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 1 0\n 4 5 1 0\n 4 8 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\n 12 14 1 0\nM CHG 1 1 -1\nM RAD 1 1 2\nM ISO 2 6 1 13 1\nA 3\nCO2Et\nA 6\nR1\nA 9\nR\nA 11\nCO2Et\nA 13\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.16708354177088544, 0.7841682165124375, 0.39269634817408705, 0.9462296479250079 ], "category_id": 1, "smiles": "*C(/C(C(=O)OCC)=C(/[1*])N)C(C([1*])=O)C(=O)OCC.[H][I-]", "molfile": "\n RDKit 2D\n\n 14 12 0 0 0 0 0 0 0 0999 V2000\n 0.5072 -8.1339 0.0000 I 0 0 0 0 0 1 0 0 0 0 0 0\n 2.2823 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4378 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3397 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3397 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3397 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8182 -6.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2417 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2417 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0168 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9187 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0168 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9187 -6.3228 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5096 -7.4252 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 1 0\n 4 5 1 0\n 4 8 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\n 12 14 1 0\nM CHG 1 1 -1\nM RAD 1 1 2\nM ISO 2 6 1 13 1\nA 3\nCO2Et\nA 6\nR1\nA 9\nR\nA 11\nCO2Et\nA 13\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.46973486743371684, 0.8097262917172873, 0.6948474237118559, 0.9851476260778473 ], "category_id": 1, "smiles": "*C1C(C(=O)OCC)=C([1*])N([H])C(*)([O-])C1([H])C(OCC)OCC", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 3.8798 -1.9921 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6434 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6434 -0.9685 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6434 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7028 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6447 -5.0630 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.4070 -6.0866 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4070 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1705 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9341 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1705 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9341 -1.9921 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4070 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4070 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 13 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\nM CHG 1 6 -1\nM ISO 1 10 1\nA 1\nEtO2C\nA 5\nR\nA 10\nR1\nA 12\nCO2Et\nA 14\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.46973486743371684, 0.8097262917172873, 0.6948474237118559, 0.9851476260778473 ], "category_id": 1, "smiles": "*C1C(C(=O)OCC)=C([1*])N([H])C(*)([O-])C1([H])C(OCC)OCC", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 3.8798 -1.9921 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6434 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6434 -0.9685 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6434 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7028 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6447 -5.0630 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.4070 -6.0866 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4070 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1705 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9341 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1705 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9341 -1.9921 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4070 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4070 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 13 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\nM CHG 1 6 -1\nM ISO 1 10 1\nA 1\nEtO2C\nA 5\nR\nA 10\nR1\nA 12\nCO2Et\nA 14\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7508754377188595, 0.8091454263717225, 0.9769884942471235, 0.970625992438728 ], "category_id": 1, "smiles": "*C1=C(C(OCC)OCC)C(*)C(C(=O)OCC)=C(*)N1", "molfile": "\n RDKit 2D\n\n 11 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0.04763095833631101, 0.4797398699349675, 0.2760430539945297 ], "category_id": 1, "smiles": "CCOC(=O)CC(C)([NH2+])O", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 5.1998 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5917 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1998 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4718 -7.3465 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 2.4959 -5.2992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6957 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\nM CHG 1 4 1\nM RAD 1 4 2\nA 2\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3411705852926463, 0.04763095833631101, 0.4797398699349675, 0.2760430539945297 ], "category_id": 1, "smiles": "CCOC(=O)CC(C)([NH2+])O", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 5.1998 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5917 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1998 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4718 -7.3465 0.0000 N 0 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0\n 4 6 2 0\n 7 8 1 0\nM CHG 1 6 1\nA 2\nCO2Et\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8204102051025512, 0.06495130682224229, 0.9639819909954978, 0.2619702708497106 ], "category_id": 1, "smiles": "CCOC(=O)C=C(C)N", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 7.0738 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6799 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0738 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3435 -7.1102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8040 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 3 5 1 0\nA 2\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.24062031015507754, 0.39403792805493654, 0.34517258629314657, 0.5455909773068351 ], "category_id": 1, "smiles": "CC(=O)CCl", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 8.1513 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0552 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1513 -7.0315 0.0000 C 0 0 0 0 0 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"category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.1745872936468234, 0.7231245492876308, 0.35617808904452225, 0.9591142974084444 ], "category_id": 1, "smiles": "CCOC(=O)/C(C(C)=N)=C(\\C)*Cl", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 9.0880 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4588 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0880 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5906 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7173 -7.8189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7173 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3465 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3171 -2.3071 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7173 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\n 6 9 1 0\n 7 8 1 0\nA 2\nCO2Et\nA 7\nL\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1745872936468234, 0.7231245492876308, 0.35617808904452225, 0.9591142974084444 ], 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0.233391695847924, 0.8104052026013007, 0.2766649282087853 ], "category_id": 1, "smiles": "*[1*]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.7894 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 17.7411 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nM ISO 1 1 1\nA 1\nR1\nA 2\nX\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.4992496248124062, 0.2575112024097155, 0.5772886443221611, 0.3022032292742116 ], "category_id": 2, "text": [ "LnPd(0)" ] } ], "conditions": [ { "category": "[Idt]", "bbox": [ 0.6423211605802901, 0.3383824891168989, 0.6668334167083542, 0.3745617489595862 ], "category_id": 3, "text": [ "A" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6828414207103551, 0.4192537758240823, 0.7628814407203601, 0.536304322373953 ], "category_id": 1, "smiles": "*[1*]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6512 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nM ISO 1 2 1\nA 1\nLn(In)\nA 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"category": "[Mol]", "bbox": [ 0.47723861930965483, 0.04372678142349863, 0.7638819409704852, 0.24924265411394222 ], "category_id": 1, "smiles": "C=CCc1ccc(C(OC)OC)cc1N[Pd](C)(Cl)Cl", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 22.1898 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 24.8429 -4.8268 0.0000 Pd 0 0 0 0 0 4 0 0 0 0 0 0\n 27.9785 -7.5827 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 28.9432 -3.4094 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 17.8483 -6.3228 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1952 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.3009 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6477 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7534 -6.3228 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6477 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.3009 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1952 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.8483 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 20.5015 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.3958 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5005 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4908 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4908 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4811 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5005 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5102 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7026 -6.3228 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9815 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9815 -2.0709 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 17.3567 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.6356 -2.3858 0.0000 Pd 0 0 0 0 0 4 0 0 0 0 0 0\n 17.3567 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 21.7415 -4.0394 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 22.1069 -1.2047 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 2 0\n 2 8 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\n 13 14 1 0\n 13 15 1 0\n 13 16 1 0\nA 6\nMeO2C\nA 14\nEt3N\nM END\n" } ] }, { "reactants": [ { "category": 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0.888944472236118, 0.33229786033956576 ], "category_id": 1, "smiles": "[1*]C([2*])=N(O)O", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 2.5981 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 3\n 4 5 1 0\n 4 6 1 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7723861930965483, 0.11971673756341257, 0.888944472236118, 0.33229786033956576 ], "category_id": 1, "smiles": "[1*]C([2*])=N(O)O", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 2.5981 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 3\n 4 5 1 0\n 4 6 1 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6973486743371686, 0.15440102601636388, 0.7398699349674838, 0.2136999707907645 ], "category_id": 2, "text": [ "HB" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5392696348174087, 0.12642982565108057, 0.6558279139569785, 0.32894131629573176 ], "category_id": 1, "smiles": "*/[Ne](O)=C(\\[1*])[2*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.5384 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7187 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7187 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2791 -3.6457 0.0000 Ne 0 0 0 0 0 4 0 0 0 0 0 0\n 8.9978 -6.8740 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 8.9978 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 4 6 1 0\nM RAD 1 5 2\nM ISO 2 2 2 3 1\nA 2\nR2\nA 3\nR1\nA 6\nOe\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5392696348174087, 0.12642982565108057, 0.6558279139569785, 0.32894131629573176 ], "category_id": 1, "smiles": "*/[Ne](O)=C(\\[1*])[2*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.5384 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7187 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7187 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2791 -3.6457 0.0000 Ne 0 0 0 0 0 4 0 0 0 0 0 0\n 8.9978 -6.8740 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 8.9978 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 4 6 1 0\nM RAD 1 5 2\nM ISO 2 2 2 3 1\nA 2\nR2\nA 3\nR1\nA 6\nOe\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3291645822911456, 0.12307328160724658, 0.43621810905452724, 0.32558477225189775 ], "category_id": 1, "smiles": "[2*]C([10*])[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 3.5093 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 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[ { "category": "[Mol]", "bbox": [ 0.4942471235617809, 0.4318753336399744, 0.5877938969484743, 0.6153664080362329 ], "category_id": 1, "smiles": "[3*]C([H])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 6.3460 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6814 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7425 -6.5591 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3460 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 1 2 3\nA 2\nR3\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5392696348174087, 0.12642982565108057, 0.6558279139569785, 0.32894131629573176 ], "category_id": 1, "smiles": "*/[Ne](O)=C(\\[1*])[2*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.5384 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7187 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7187 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2791 -3.6457 0.0000 Ne 0 0 0 0 0 4 0 0 0 0 0 0\n 8.9978 -6.8740 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 8.9978 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 4 6 1 0\nM RAD 1 5 2\nM ISO 2 2 2 3 1\nA 2\nR2\nA 3\nR1\nA 6\nOe\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4197098549274637, 0.6869726809713582, 0.5617808904452226, 0.9118611319082359 ], "category_id": 1, "smiles": "[1*]C([2*])(C([3*])O)[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 5.6667 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6667 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6667 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1111 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0000 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6667 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6667 -6.7165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 3 3 2 4 1 6 3\nA 2\nNO2\nA 3\nR2\nA 4\nR1\nA 6\nR3\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6068034017008505, 0.7250135134681434, 0.6508254127063532, 0.7887878503009894 ], "category_id": 2, "text": [ "HB" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6823411705852926, 0.6377433683284595, 0.8184092046023012, 0.861512971250726 ], "category_id": 1, "smiles": "[1*]C([2*])(C([3*])O)[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 5.5667 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5667 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7103 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1410 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8853 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5981 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5981 -6.7165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 3 3 2 4 1 6 3\nA 2\nNO2\nA 3\nR2\nA 4\nR1\nA 6\nR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6823411705852926, 0.6377433683284595, 0.8184092046023012, 0.861512971250726 ], "category_id": 1, "smiles": 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5.6667 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6667 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6667 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1111 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0000 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6667 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6667 -6.7165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 3 3 2 4 1 6 3\nA 2\nNO2\nA 3\nR2\nA 4\nR1\nA 6\nR3\nM END\n" } ] } ], "Hetero-Diels\u2013Alder reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03901950975487744, 0.15919100133621186, 0.2466233116558279, 0.7941862177773236 ], "category_id": 1, "smiles": "CCOC(OCC)C(C=Cc1ccccc1)=NS(=O)(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 5.6226 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8089 -1.9921 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6226 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4363 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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"[Txt]", "bbox": [ 0.21160580290145073, 0.4440504343080632, 0.4197098549274637, 0.5425599163217973 ], "category_id": 2, "text": [ "oxidative addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4442221110555278, 0.27279548865341763, 0.6248124062031015, 0.5046716540088226 ], "category_id": 1, "smiles": "*c1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 3.3296 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9249 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3296 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9540 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3587 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1681 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9540 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\nA 6\nPd(I)W\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4442221110555278, 0.27279548865341763, 0.6248124062031015, 0.5046716540088226 ], "category_id": 1, "smiles": 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0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2452 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM ISO 1 8 2\nA 2\nRi\nA 8\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.10805402701350675, 0.47055468608340156, 0.24562281140570286, 0.6274062481112022 ], "category_id": 1, "smiles": "[2*]N([H])([H])CCCC([Rf])[Rf]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 3.8971 5.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 6.0000 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 2.5981 6.0000 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 3.8971 3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 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0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\nM CHG 1 6 1\nM ISO 2 2 1 7 2\nA 2\nR1\nA 7\nR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.38369184592296146, 0.5528374727209363, 0.5767883941970986, 0.6762616526772383 ], "category_id": 1, "smiles": "[1*]CCCC[N+]([2*])([H])Cl", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 6.5431 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9549 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9202 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5083 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0965 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 20.4735 -5.0630 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 24.0617 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 20.6846 -1.3622 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 24.0617 -3.2520 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\nM CHG 1 6 1\nM ISO 2 2 1 7 2\nA 2\nR1\nA 7\nR2\nM END\n" } ] }, { "reactants": 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0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7534 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4503 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4503 -4.5906 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1358 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 4 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nM ISO 2 3 7 8 2\nA 3\nR7\nA 8\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.33016508254127064, 0.7799722483349644, 0.46773386693346675, 0.9445378216100337 ], "category_id": 1, "smiles": "[2*]NCCCC([7*])Cl", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.0566 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0566 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0566 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5732 -6.2441 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7534 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4503 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4503 -4.5906 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1358 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 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0\n 7 8 1 0\nM CHG 1 4 1\nM ISO 2 3 1 5 2\nA 3\nR1\nA 5\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6928464232116058, 0.8022571697159633, 0.743871935967984, 0.8699690462197679 ], "category_id": 1, "smiles": "O", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 6.5256 -5.6929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7963981990995498, 0.7731153494485031, 0.8939469734867433, 0.9393951474451878 ], "category_id": 1, "smiles": "[1*]C1CCCN1[2*]", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 5.5118 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5669 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5748 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7717 -4.7480 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7717 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3701 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5827 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 7 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\nM ISO 2 3 1 5 2\nA 3\nR1\nA 5\nR2\nM END\n" } ] } ], "Horner\u2013Wadsworth\u2013Emmons reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.028514257128564282, 0.1618338408970567, 0.25362681340670334, 0.682431859204456 ], "category_id": 1, "smiles": "[H]C(C(=O)OCC)P(=O)(OCC)OCC", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 3.3194 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8422 -3.2520 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1867 -2.4646 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8422 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4978 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4978 -7.7402 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0205 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5433 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0205 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\n 2 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 2 0\nA 1\nEtO\nA 3\nEtO\nA 8\nOEt\nM END\n" }, { "category": "[Txt]", "bbox": [ 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2 3 1 0\n 2 4 2 0\n 2 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 9 10 1 0\n 9 11 1 0\n 9 12 2 0\nA 1\nEtO\nA 3\nEtO\nA 7\nOEt\nA 11\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3491745872936468, 0.09554046028862384, 0.575287643821911, 0.8520649213495637 ], "category_id": 1, "smiles": "*C([H])=O.CCO/C(O)=C/P(=O)(OCC)OCC", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 2.6513 -4.1969 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2969 -3.1732 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4684 -2.6220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2969 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0339 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6795 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3252 -4.1969 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6795 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5768 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5768 -5.0630 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2224 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8398 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 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11\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7183591795897949, 0.17548247808114584, 0.9449724862431216, 0.7662734876210036 ], "category_id": 1, "smiles": "*C([O-])C(C(=O)OCC)P(=O)(OCC)OCC", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 3.0532 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2844 -2.7008 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8184 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2844 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5156 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5156 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7468 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2844 -7.8189 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 9.7468 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9780 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7468 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\n 2 5 1 0\n 5 6 1 0\n 5 9 1 0\n 6 7 1 0\n 6 8 1 0\n 9 10 1 0\n 9 11 2 0\nM CHG 1 8 -1\nA 1\nEtO\nA 3\nEtO\nA 7\nR\nA 10\nOEt\nM 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"conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8734367183591796, 0.8417283418494963, 0.9639819909954978, 0.9570845690702494 ], "category_id": 1, "smiles": "*[C@@H]1O[C@@H]1[1*]", "molfile": "\n RDKit 2D\n\n 5 5 0 0 0 0 0 0 0 0999 V2000\n 3.4973 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5646 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -7.2677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2707 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2034 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 3 1 0\n 1 4 1 0\n 3 4 1 0\n 1 2 1 1\n 4 5 1 1\nM ISO 1 5 1\nA 2\nR\nA 5\nR1\nM END\n" } ] } ], "Japp\u2013Klingemann hydrazone synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03301650825412707, 0.11241217990337231, 0.24412206103051526, 0.42563835109043885 ], "category_id": 1, "smiles": "*OC(=O)C([H])(C)C(C)=O.[O-]", "molfile": "\n RDKit 2D\n\n 8 6 0 0 0 0 0 0 0 0999 V2000\n 4.6228 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6228 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 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0 0 0 0 0 0\n 8.4009 -3.8031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7255 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6754 -1.9134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8503 -4.9843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8503 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0501 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7255 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5257 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4009 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7756 -1.9134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9758 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 11 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 9 10 1 0\n 11 12 1 0\nM ISO 1 12 2\nA 7\nR\nA 10\nR\nA 12\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7273636818409205, 0.06216243715077878, 0.92096048024012, 0.49729949720623023 ], "category_id": 1, "smiles": "*/C=C/C(*)OC(=O)C[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 6.8846 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7839 -3.6457 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9063 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0071 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0071 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1079 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9063 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8846 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7839 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9063 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 10 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\nA 6\nR\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7273636818409205, 0.06216243715077878, 0.92096048024012, 0.49729949720623023 ], "category_id": 1, "smiles": "*/C=C/C(*)OC(=O)C[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 6.8846 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7839 -3.6457 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9063 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0071 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0071 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1079 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9063 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8846 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7839 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9063 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 10 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\nA 6\nR\nA 9\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.19259629814907453, 0.5775455524372356, 0.38819409704852426, 0.9652131150320923 ], "category_id": 1, "smiles": "*/C=C/C(*)OC(=C)O[2*]", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 7.7227 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4777 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4777 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2328 -4.1969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2328 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8980 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0803 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\nM ISO 1 5 1\nA 2\nR\nA 5\nR1\nA 7\nCO2R2\nM END\n" } ] } ], "Jones oxidation.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.15957978989494748, 0.20275340372889147, 0.3031515757878939, 0.8380474020794182 ], "category_id": 1, "smiles": "[1*]C([2*])O[H].[H]O[Cr](=O)=O", "molfile": "\n RDKit 2D\n\n 10 8 0 0 0 0 0 0 0 0999 V2000\n 3.1544 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3750 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0147 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1544 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4559 -3.7244 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7721 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7942 -1.9921 0.0000 Cr 0 0 0 0 0 5 0 0 0 0 0 0\n 8.2500 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2500 -4.9843 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5515 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 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"[Mol]", "bbox": [ 0.39919959979989994, 0.14192738261022403, 0.5257628814407204, 0.7727157497667754 ], "category_id": 1, "smiles": "[1*]C([2*])([H])O[Cr](=O)(O)O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 3.1817 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1615 -6.4016 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2727 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7474 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1817 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1615 -2.7795 0.0000 Cr 0 0 0 0 0 5 0 0 0 0 0 0\n 6.7170 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4342 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4646 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 2 0\nM ISO 2 3 1 4 2\nA 3\nR1\nA 4\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6358179089544772, 0.32665826156321404, 0.7263631815907954, 0.6690862323053419 ], "category_id": 1, "smiles": "[1*]C([2*])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.8287 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4055 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1594 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8287 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7613806903451726, 0.4415518570095859, 0.8479239619809905, 0.6488108919324527 ], "category_id": 1, "smiles": "O=[Cf]O", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 2.6575 -6.0079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5630 -1.9921 0.0000 Cf 0 0 0 0 0 3 0 0 0 0 0 0\n 12.9921 -5.2205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\nM END\n" } ] } ], "Julia\u2013Kocienski olefination.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05152576288144072, 0.2162702973108176, 0.2066033016508254, 0.5406757432770439 ], "category_id": 1, "smiles": "[1*]C([H])S(=O)(=O)c1nnnn1-c1ccccc1", "molfile": "\n RDKit 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3515 -2.1496 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1667 -0.0236 0.0000 K 0 0 0 0 0 1 0 0 0 0 0 0\n 1.0870 -2.6220 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8152 -4.9055 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8986 -5.8504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4421 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9783 -5.7717 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0617 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0545 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 3 1 0\n 1 12 1 0\n 3 4 1 0\n 4 5 1 0\n 4 9 1 0\n 4 11 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 11 12 1 0\n 1 2 1 1\n 12 13 1 6\nM ISO 2 2 2 13 1\nA 2\nR2\nA 10\nPh\nA 13\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.20410205102551277, 0.5986052871995844, 0.40070035017508754, 0.9642050755107284 ], "category_id": 1, "smiles": "[1*][C@H]([C@H]([2*])Oc1nnnn1-c1ccccc1)S(=O)O", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 2.7256 -3.1732 0.0000 N 0 0 0 0 0 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0.8419093716742542 ], "category_id": 1, "smiles": "[1*]/C=C/[2*]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 9.5653 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9042 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.0312 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 20.4970 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\nM ISO 2 2 1 4 2\nA 2\nR1\nA 4\nR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.6853426713356678, 0.6449489223376167, 0.8029014507253627, 0.9152867939761388 ], "category_id": 1, "smiles": "Oc1nnnn1-c1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 3.8050 -4.9055 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5129 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1504 -3.7244 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5043 -0.8110 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2475 -0.1811 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7518 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6719 -3.0945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 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"text": [ "coupling" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6468234117058529, 0.031380396080393134, 0.7593796898449224, 0.2362246482718484 ], "category_id": 1, "smiles": "*C(OO)C(*)S(*)(=O)=O", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.4915 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4915 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2903 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7686 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7686 -6.4016 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9698 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 1 0\nA 2\nSO2Ar\nA 3\nR\nA 5\nOO\nA 6\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.6993496748374187, 0.23709632594074817, 0.8184092046023012, 0.3617462325934209 ], "category_id": 1, "smiles": "CC(=O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.7920 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4882 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3164 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0.653758251674857 ], "category_id": 2, "text": [ "single electron", "transfer (SET)" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.678839419709855, 0.5003429819484906, 0.7658829414707353, 0.5831523604939726 ], "category_id": 1, "smiles": "*.*", "molfile": "\n RDKit 2D\n\n 2 0 0 0 0 0 0 0 0 0999 V2000\n 5.6640 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8136 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nSO2\nA 2\nAr\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.8049024512256128, 0.4820377509015947, 0.919959979989995, 0.6258645662700631 ], "category_id": 1, "smiles": "*CC([1*])OC(C)=O", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 4.8415 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4304 -3.3307 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2526 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2526 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5536 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\nM ISO 1 5 1\nA 2\nR\nA 4\nOAc\nA 5\nR1\nM 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0.8394197098549274, 0.9300800727160966 ], "category_id": 1, "smiles": "*/C=C/[1*]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 8.4689 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5022 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2432 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 20.2100 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\nM ISO 1 4 1\nA 2\nR\nA 4\nR1\nM END\n" } ] } ], "Kahne glycosidation.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.07553776888444222, 0.038711303217151646, 0.42021010505252626, 0.469530645472549 ], "category_id": 1, "smiles": "*CC1OC([SH](O)c2ccccc2)C(*)C(*)C1*.CC.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)F", "molfile": "\n RDKit 2D\n\n 30 28 0 0 0 0 0 0 0 0999 V2000\n 3.9257 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3554 -6.9528 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8265 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8265 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1819 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 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0.5717858929464732, 0.11613390965145495, 0.7973986993496749, 0.41833182508857425 ], "category_id": 1, "smiles": "*CC1OC([SH+](OS(=O)(=O)C(F)(F)F)c2ccccc2)C(*)C(*)C1*", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 3.9236 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9236 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4112 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6846 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9924 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7535 -3.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4973 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9677 -6.1654 0.0000 S 0 0 0 0 0 4 0 0 0 0 0 0\n 15.5489 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.7115 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1550 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8988 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6674 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3423 -6.0079 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 1 0\n 3 4 1 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 11 1 0\n 8 9 1 0\n 8 10 1 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\nM CHG 1 8 1\nM RAD 1 8 2\nA 2\nPivO\nA 5\nOPiv\nA 9\nOTf\nA 10\nPh\nA 12\nPvO\nA 14\nPivO\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5717858929464732, 0.11613390965145495, 0.7973986993496749, 0.41833182508857425 ], "category_id": 1, "smiles": "*CC1OC([SH+](OS(=O)(=O)C(F)(F)F)c2ccccc2)C(*)C(*)C1*", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 3.9236 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9236 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4112 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6846 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9924 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7535 -3.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4973 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9677 -6.1654 0.0000 S 0 0 0 0 0 4 0 0 0 0 0 0\n 15.5489 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.7115 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1550 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8988 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6674 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3423 -6.0079 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 1 0\n 3 4 1 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 11 1 0\n 8 9 1 0\n 8 10 1 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\nM CHG 1 8 1\nM RAD 1 8 2\nA 2\nPivO\nA 5\nOPiv\nA 9\nOTf\nA 10\nPh\nA 12\nPvO\nA 14\nPivO\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8379189594797398, 0.18481525406898205, 0.8834417208604303, 0.26348661221996766 ], "category_id": 2, "text": [ "Sn" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.01250625312656328, 0.5694307828071339, 0.11955977988994497, 0.678072182158495 ], "category_id": 1, "smiles": "O=S(=O)(OSc1ccccc1)C(F)(F)F", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 11.4704 -2.2283 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1419 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 17.4034 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\nA 2\nPh\nA 3\nOTf\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.14757378689344672, 0.509490700406383, 0.3076538269134567, 0.7954548435266322 ], "category_id": 1, "smiles": "*CC1O=CC(*)C(*)C1O", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 8 1 0\n 6 7 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 1 0\nA 2\nPivO\nA 7\nOPiv\nA 11\nPivO\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.01250625312656328, 0.5694307828071339, 0.11955977988994497, 0.678072182158495 ], "category_id": 1, "smiles": "O=S(=O)(OSc1ccccc1)C(F)(F)F", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 11.4704 -2.2283 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1419 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 17.4034 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\nA 2\nPh\nA 3\nOTf\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.14757378689344672, 0.509490700406383, 0.3076538269134567, 0.7954548435266322 ], "category_id": 1, "smiles": "*CC1O=CC(*)C(*)C1O", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 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0 0\n 5.2385 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0558 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 24 1 0\n 3 4 1 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 22 1 0\n 8 9 1 0\n 9 10 1 0\n 9 20 1 0\n 10 11 1 0\n 10 16 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\n 15 16 1 0\n 16 17 1 0\n 17 18 1 0\n 18 19 1 0\n 18 20 1 0\n 20 21 1 0\n 22 23 1 0\n 22 24 1 0\n 24 25 1 0\nA 2\nPvO\nA 5\nOPiv\nA 13\nPh\nA 19\nSPh\nA 21\nN3\nA 23\nPivO\nA 25\nPivO\nM END\n" } ] } ], "Knoevenagel condensation.png": [], "Knorr pyrazole synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.16108054027013508, 0.0937401608152319, 0.3311655827913957, 0.38880862156317775 ], "category_id": 1, "smiles": "[1*]C(=O)C([3*])C(=O)O[2*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 6.0945 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0945 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6760 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6760 -7.4252 0.0000 R 0 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0 0 0 0 0 0\n 7.4977 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 2 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\nM ISO 2 2 3 4 1\nA 2\nR3\nA 4\nR1\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.48024012006003003, 0.05858760050951994, 0.6473236618309155, 0.42609164006923583 ], "category_id": 1, "smiles": "*n1nc([1*])c([3*])c1O", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 4.6198 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9830 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3478 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9846 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6662 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4838 -2.3071 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4838 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3772 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4977 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 2 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\nM ISO 2 2 3 4 1\nA 2\nR3\nA 4\nR1\nA 7\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7963981990995498, 0.05858760050951994, 0.9439719859929965, 0.42609164006923583 ], "category_id": 1, "smiles": "*N1N=C([1*])C([3*])C1=O", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 4.7124 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0588 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4235 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0098 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6830 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5006 -2.3071 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5006 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3856 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5398 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 1 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\nM ISO 2 2 3 4 1\nA 2\nR3\nA 4\nR1\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7963981990995498, 0.05858760050951994, 0.9439719859929965, 0.42609164006923583 ], "category_id": 1, "smiles": "*N1N=C([1*])C([3*])C1=O", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 4.7124 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0588 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4235 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0098 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6830 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5006 -2.3071 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5006 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3856 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5398 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 1 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\nM ISO 2 2 3 4 1\nA 2\nR3\nA 4\nR1\nA 7\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.48024012006003003, 0.05858760050951994, 0.6473236618309155, 0.42609164006923583 ], "category_id": 1, "smiles": "*n1nc([1*])c([3*])c1O", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 4.6198 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9830 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3478 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9846 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6662 -3.6457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4838 -2.3071 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4838 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3772 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4977 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 2 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\nM ISO 2 2 3 4 1\nA 2\nR3\nA 4\nR1\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.060530265132566284, 0.5667018812920838, 0.15257628814407204, 0.9288797753509341 ], "category_id": 1, "smiles": "*C(=O)CC(=O)P", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.9400 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0936 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9400 -7.9764 0.0000 R 0 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1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\nA 3\nR\nA 8\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5797898949474737, 0.5709627976927761, 0.7028514257128564, 0.938466837252492 ], "category_id": 1, "smiles": "*C1=NNC(*)(O)C1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 1.5093 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8509 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8944 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7453 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0310 -5.2205 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0310 -2.8583 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8509 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1801 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 7 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\nA 3\nR\nA 8\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5797898949474737, 0.5709627976927761, 0.7028514257128564, 0.938466837252492 ], "category_id": 1, "smiles": "*C1=NNC(*)(O)C1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 1.5093 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8509 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8944 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7453 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0310 -5.2205 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0310 -2.8583 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8509 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1801 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 7 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\nA 3\nR\nA 8\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8259129564782391, 0.5730932558931223, 0.9309654827413707, 0.9427277536531844 ], "category_id": 1, "smiles": "*c1cc(*)[nH]n1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 0.4748 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8519 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0921 0.0551 0.0000 R 0 0 0 0 0 0 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0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.3886 2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.5377 3.4056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9791 2.9544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 10 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 10 11 1 0\nA 5\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.10055027513756878, 0.03778722694680674, 0.2321160580290145, 0.28155188705463846 ], "category_id": 1, "smiles": "*C1(CO[H])CCCCC1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 2.4422 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4383 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4383 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4422 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2524 -1.9921 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5693 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9489 -1.9134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0761 -0.0236 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4460 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4460 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 9 1 0\n 6 7 1 0\n 7 8 1 0\n 9 10 1 0\nA 5\nR\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.2381190595297649, 0.14299872158301374, 0.29064532266133064, 0.21338669334667335 ], "category_id": 2, "text": [ "H" ] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.47723861930965483, 0.02296870657550998, 0.615807903951976, 0.2689561447390362 ], "category_id": 1, "smiles": "*C1(CO([H])[H])CCCCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6491 -0.9642 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.3886 2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.5377 3.4056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9791 2.9544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 10 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 10 11 1 0\nA 5\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7423711855927964, 0.025191484631204495, 0.8629314657328664, 0.23857817797787784 ], "category_id": 1, "smiles": "*C1(C)CCCCC1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 5.1458 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8368 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5173 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5278 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5278 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8368 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1458 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1458 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 8 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nA 3\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7423711855927964, 0.025191484631204495, 0.8629314657328664, 0.23857817797787784 ], "category_id": 1, "smiles": "*C1(C)CCCCC1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 5.1458 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8368 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5173 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5278 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5278 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8368 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1458 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1458 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 8 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nA 3\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.47723861930965483, 0.02296870657550998, 0.615807903951976, 0.2689561447390362 ], "category_id": 1, "smiles": "*C1(CO([H])[H])CCCCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6491 -0.9642 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.3886 2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.5377 3.4056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9791 2.9544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 10 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 10 11 1 0\nA 5\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.29214607303651824, 0.35193985881829803, 0.407703851925963, 0.5460624756822856 ], "category_id": 1, "smiles": "*CC1CCCCC1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 4.2047 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1913 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6764 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1535 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1535 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6764 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2693 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2693 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 8 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nA 2\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.4347173586793397, 0.3415668945583903, 0.5187593796898449, 0.3926907898393642 ], "category_id": 1, "smiles": "O=Cl", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6048024012006002, 0.3163754099271858, 0.7488744372186094, 0.5423578455894614 ], "category_id": 1, "smiles": "*CC1(C#O)CCCCC1.O.O", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0586 0.4512 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3886 -2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 2.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 6 1 0\n 3 10 1 0\n 4 5 3 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\nA 2\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6048024012006002, 0.3163754099271858, 0.7488744372186094, 0.5423578455894614 ], "category_id": 1, "smiles": "*CC1(C#O)CCCCC1.O.O", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0586 0.4512 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3886 -2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 2.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 6 1 0\n 3 10 1 0\n 4 5 3 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\nA 2\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.29214607303651824, 0.35193985881829803, 0.407703851925963, 0.5460624756822856 ], "category_id": 1, "smiles": "*CC1CCCCC1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 4.2047 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1913 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6764 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1535 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1535 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6764 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2693 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2693 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 8 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nA 2\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.4347173586793397, 0.3415668945583903, 0.5187593796898449, 0.3926907898393642 ], "category_id": 1, "smiles": "O=Cl", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6048024012006002, 0.3163754099271858, 0.7488744372186094, 0.5423578455894614 ], "category_id": 1, "smiles": "*CC1(C#O)CCCCC1.O", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0586 0.4512 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3886 -2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 2.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 6 1 0\n 3 10 1 0\n 4 5 3 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\nA 2\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.40070035017508754, 0.6646106386526597, 0.5852926463231616, 0.9068934467233617 ], "category_id": 1, "smiles": "*CC1(C(=O)O)CCCCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.2833 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9761 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4369 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1230 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4302 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5018 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3960 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3960 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4369 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4779 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4779 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 7 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nA 2\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.40070035017508754, 0.6646106386526597, 0.5852926463231616, 0.9068934467233617 ], "category_id": 1, "smiles": "*CC1(C(=O)O)CCCCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.2833 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9761 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4369 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1230 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4302 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5018 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3960 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3960 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4369 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4779 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4779 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 7 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nA 2\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.04102051025512756, 0.6527558223556222, 0.19909954977488745, 0.9031888166305376 ], "category_id": 1, "smiles": "*CC1(C#O)CCCCC1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0586 0.4512 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3886 -2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 6 1 0\n 3 10 1 0\n 4 5 3 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\nA 2\nR\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.21660830415207605, 0.782417875604469, 0.29214607303651824, 0.8439147351453504 ], "category_id": 2, "text": [ ":OH2" ] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04102051025512756, 0.6527558223556222, 0.19909954977488745, 0.9031888166305376 ], "category_id": 1, "smiles": "*CC1(C#O)CCCCC1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0586 0.4512 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3886 -2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 6 1 0\n 3 10 1 0\n 4 5 3 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\nA 2\nR\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.21660830415207605, 0.782417875604469, 0.29214607303651824, 0.8439147351453504 ], "category_id": 2, "text": [ ":OH2" ] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.40070035017508754, 0.6646106386526597, 0.5852926463231616, 0.9068934467233617 ], "category_id": 1, "smiles": "*CC1(C(=O)O)CCCCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.2833 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9761 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4369 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1230 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4302 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5018 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3960 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3960 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4369 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4779 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4779 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 7 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nA 2\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.40070035017508754, 0.6646106386526597, 0.5852926463231616, 0.9068934467233617 ], "category_id": 1, "smiles": "*CC1(C(=O)O)CCCCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.2833 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9761 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4369 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1230 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4302 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5018 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3960 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3960 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4369 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4779 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4779 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 7 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nA 2\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7463731865932967, 0.6660924906897894, 0.9174587293646823, 0.9046706686676672 ], "category_id": 1, "smiles": "*CC1(C(=O)O)CCCCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.3528 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9220 -1.8346 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5263 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2027 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4658 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6160 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4308 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4308 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5263 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5380 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5380 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 7 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nA 2\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7463731865932967, 0.6660924906897894, 0.9174587293646823, 0.9046706686676672 ], "category_id": 1, "smiles": "*CC1(C(=O)O)CCCCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.3528 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9220 -1.8346 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5263 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2027 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4658 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6160 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4308 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4308 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5263 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5380 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5380 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 7 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nA 2\nR\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.6253126563281641, 0.7186982380078929, 0.7128564282141071, 0.7964954699572009 ], "category_id": 1, "smiles": "[H].[I-]", "molfile": "\n RDKit 2D\n\n 2 0 0 0 0 0 0 0 0 0999 V2000\n 2.7021 -6.0866 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 8.3637 -6.0866 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\nM CHG 1 1 -1\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.40070035017508754, 0.6646106386526597, 0.5852926463231616, 0.9068934467233617 ], "category_id": 1, "smiles": "*CC1(C(=O)O)CCCCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.2833 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9761 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4369 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1230 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4302 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5018 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3960 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3960 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4369 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4779 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4779 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 7 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nA 2\nR\nM END\n" } ] } ], "Koenig\u2013Knorr glycosidation.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.12906453226613307, 0.041733792066101075, 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0.05357224066578744, 0.5237618809404703, 0.48637955341307015 ], "category_id": 1, "smiles": "*CC(=O)OC(C*)(O[H])Oc1ccccc1C(C)=O", "molfile": "\n RDKit 2D\n\n 20 20 0 0 0 0 0 0 0 0999 V2000\n 10.8097 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7173 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8559 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0543 -4.1181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1005 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1929 -2.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6032 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0136 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3179 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3179 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0136 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6032 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1929 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8885 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1929 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6901 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5842 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1005 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5108 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8097 -2.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 20 2 0\n 4 5 1 0\n 5 6 1 0\n 5 16 1 0\n 5 18 1 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 1 0\n 13 15 2 0\n 16 17 1 0\n 18 19 1 0\nA 2\nR\nA 19\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.567783891945973, 0.17481468006730636, 0.6178089044522261, 0.25376324525899313 ], "category_id": 2, "text": [ "acyl" ] }, { "category": "[Txt]", "bbox": [ 0.5537768884442221, 0.29746691527581975, 0.6308154077038519, 0.3665469098185456 ], "category_id": 2, "text": [ "transfer" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6523261630815408, 0.08176815680567556, 0.8169084542271136, 0.46523261630815405 ], "category_id": 1, "smiles": "*CC(=O)Oc1ccccc1C(C)=O", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 7.7847 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8860 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0822 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2784 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4747 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4747 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2784 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0822 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8860 -1.6772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9745 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0188 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0188 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8860 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 14 2 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 13 2 0\n 11 12 1 0\nA 12\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6523261630815408, 0.08176815680567556, 0.8169084542271136, 0.46523261630815405 ], "category_id": 1, "smiles": "*CC(=O)Oc1ccccc1C(C)=O", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 7.7847 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8860 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0822 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2784 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4747 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4747 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2784 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0822 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8860 -1.6772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9745 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0188 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2023 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0188 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8860 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 14 2 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 13 2 0\n 11 12 1 0\nA 12\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8349174587293647, 0.22133794169812177, 0.9399699849924963, 0.29746691527581975 ], "category_id": 2, "text": [ "enolization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.04052026013006503, 0.5329028150438855, 0.2046023011505753, 0.9826276774751012 ], "category_id": 1, "smiles": "*/C=C(\\O[H])Oc1ccccc1C(C)=O", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 6.5712 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0298 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4073 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8659 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3245 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3245 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8659 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4073 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9487 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8146 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7070 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8146 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7070 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4918 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9487 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 2 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 13 2 0\n 11 12 1 0\n 13 14 1 0\nA 14\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04052026013006503, 0.5329028150438855, 0.2046023011505753, 0.9826276774751012 ], "category_id": 1, "smiles": "*/C=C(\\O[H])Oc1ccccc1C(C)=O", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 6.5712 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0298 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4073 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8659 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3245 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3245 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8659 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4073 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9487 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8146 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7070 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8146 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7070 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4918 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9487 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 2 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 13 2 0\n 11 12 1 0\n 13 14 1 0\nA 14\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.23011505752876438, 0.6626040292873709, 0.3266633316658329, 0.7443721860930466 ], "category_id": 2, "text": [ "6-exo-trig" ] }, { "category": "[Txt]", "bbox": [ 0.22161080540270134, 0.7852562644958843, 0.33366683341670833, 0.8599754422665878 ], "category_id": 2, "text": [ "ring closure" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3551775887943972, 0.6259493383055164, 0.49874937468734365, 0.9290554368093137 ], "category_id": 1, "smiles": "*C1([H])C(=O)Oc2ccccc2C1(C)O", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 6.0247 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3987 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6671 -7.8189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0734 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8538 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5285 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5285 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8538 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0734 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3987 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6184 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8380 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6184 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5209 -6.0079 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1551 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 13 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 2 0\n 11 13 1 0\n 13 14 1 0\n 13 15 1 0\nA 15\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3551775887943972, 0.6259493383055164, 0.49874937468734365, 0.9290554368093137 ], "category_id": 1, "smiles": "*C1([H])C(=O)Oc2ccccc2C1(C)O", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 6.0247 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3987 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6671 -7.8189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0734 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8538 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5285 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5285 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8538 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0734 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3987 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6184 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8380 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6184 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5209 -6.0079 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1551 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 13 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 2 0\n 11 13 1 0\n 13 14 1 0\n 13 15 1 0\nA 15\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5252626313156579, 0.8486970758106326, 0.5542771385692846, 0.9234162535813362 ], "category_id": 2, "text": [ ":B" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5672836418209104, 0.5963436263586338, 0.7228614307153577, 0.9346946200372913 ], "category_id": 1, "smiles": "*C1=C([O-])Oc2ccccc2C1(C)O.[OH-]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 13.0645 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9784 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9784 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0645 -1.0472 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.2009 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8349 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6746 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5144 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5144 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6746 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8349 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2009 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6579 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6411 -8.6063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6411 -9.0000 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 12 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 1 0\nM CHG 2 4 -1 15 -1\nA 1\n*\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5672836418209104, 0.5963436263586338, 0.7228614307153577, 0.9346946200372913 ], "category_id": 1, "smiles": "*C1=C([O-])Oc2ccccc2C1(C)O.[OH-]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 13.0645 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9784 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9784 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0645 -1.0472 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.2009 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8349 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6746 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5144 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5144 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6746 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8349 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2009 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6579 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6411 -8.6063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6411 -9.0000 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 12 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 1 0\nM CHG 2 4 -1 15 -1\nA 1\n*\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7338669334667334, 0.683750966392287, 0.7998999499749875, 0.7767974896539178 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.8159079539769885, 0.6597844376733821, 0.9589794897448725, 0.9530219655282186 ], "category_id": 1, "smiles": "*c1c(C)c2ccccc2oc1=O", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 7.9302 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9302 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3201 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8186 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3201 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8186 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9302 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2143 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2143 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6072 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6072 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 9 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\nA 4\nR\nM END\n" } ] } ], "Kr\u00f6hnke pyridine synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.061530765382691345, 0.029942005614594015, 0.23011505752876438, 0.22706020924400458 ], "category_id": 1, "smiles": "*C(=O)C[n+]1ccccc1.[H+].[H]", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 4.5293 -8.0551 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 10.1489 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3037 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4584 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4584 -4.8268 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 4.5293 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6840 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8388 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6840 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3037 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1489 -4.7480 0.0000 C 0 0 0 0 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"bbox": [ 0.4137068534267134, 0.04366542485461627, 0.5832916458229115, 0.18464236795666308 ], "category_id": 1, "smiles": "*/C(O)=C/[n+]1ccccc1.[H]", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 14.3886 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7725 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1564 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1564 -6.1654 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 6.4213 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9242 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1891 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9242 -3.2520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7725 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3886 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1891 -1.7559 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 1 10 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 9 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 9 10 2 0\nM CHG 1 4 1\nA 7\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6163081540770385, 0.09980668538198005, 0.7168584292146073, 0.14471969380387106 ], "category_id": 2, "text": [ "Michael" ] }, { "category": "[Txt]", "bbox": [ 0.6183091545772886, 0.16530482266390445, 0.7143571785892946, 0.202732329682147 ], "category_id": 2, "text": [ "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7328664332166083, 0.02245650421094551, 0.9414707353676839, 0.2956773054441159 ], "category_id": 1, "smiles": "*C(=O)C(C([7*])/C=C(/[2*])O[H])[n+]1ccccc1.Br", "molfile": "\n RDKit 2D\n\n 18 17 0 0 0 0 0 0 0 0999 V2000\n 9.2287 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9532 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6026 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6026 -2.4646 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 5.3271 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9766 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9766 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6260 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3271 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8277 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8769 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4514 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0762 -8.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3259 -5.6929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8253 -6.0866 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9532 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2287 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6272 -0.4173 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 17 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 16 1 0\n 5 6 1 0\n 5 9 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 9 11 1 0\n 11 12 2 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\n 16 17 2 0\nM CHG 1 4 1\nM ISO 2 10 7 13 2\nA 7\nR\nA 10\nR7\nA 13\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7328664332166083, 0.02245650421094551, 0.9414707353676839, 0.2956773054441159 ], "category_id": 1, "smiles": "*C(=O)C(C([7*])/C=C(/[2*])O[H])[n+]1ccccc1.Br", "molfile": "\n RDKit 2D\n\n 18 17 0 0 0 0 0 0 0 0999 V2000\n 9.2287 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9532 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6026 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6026 -2.4646 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 5.3271 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9766 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9766 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6260 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3271 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8277 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8769 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4514 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0762 -8.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3259 -5.6929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8253 -6.0866 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9532 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2287 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6272 -0.4173 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 17 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 16 1 0\n 5 6 1 0\n 5 9 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 9 11 1 0\n 11 12 2 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\n 16 17 2 0\nM CHG 1 4 1\nM ISO 2 10 7 13 2\nA 7\nR\nA 10\nR7\nA 13\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.16708354177088544, 0.32998585354417154, 0.3471735867933967, 0.6269107425555621 ], "category_id": 1, "smiles": "*C(=O)CC([1*])([H])C(C(*)=O)[n+]1ccccc1.Br", "molfile": "\n RDKit 2D\n\n 18 17 0 0 0 0 0 0 0 0999 V2000\n 7.2262 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9721 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7179 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7179 -3.0157 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 3.4638 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2097 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2097 -1.5197 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9555 -3.7244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4638 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4791 -6.2441 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8374 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1055 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6722 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{ "category": "[Mol]", "bbox": [ 0.46673336668334164, 0.3555613166733039, 0.6028014007003502, 0.5982163205082429 ], "category_id": 1, "smiles": "*C(=O)/C=C(/*)CC([2*])=O.N", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 3.4636 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7593 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3745 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6048 -5.2205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9035 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6628 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9035 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4190 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4190 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8797 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6628 -7.2677 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 4 2 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\nM ISO 1 3 2\nA 3\nR2\nA 6\nR\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.46673336668334164, 0.3555613166733039, 0.6028014007003502, 0.5982163205082429 ], "category_id": 1, "smiles": "*C(=O)/C=C(/*)CC([2*])=O.N", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 3.4636 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7593 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3745 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6048 -5.2205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9035 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6628 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9035 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4190 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4190 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8797 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6628 -7.2677 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 4 2 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\nM ISO 1 3 2\nA 3\nR2\nA 6\nR\nA 9\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6753376688344173, 0.352442357755117, 0.8514257128564282, 0.5982163205082429 ], "category_id": 1, "smiles": "*C(=O)/C=C(/[1*])CC([2*])(N)O", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 4.6498 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6498 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7476 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1293 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1293 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8906 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7066 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8748 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4521 -8.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9022 -6.0866 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4521 -4.8268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM ISO 2 6 1 9 2\nA 1\nR\nA 6\nR1\nA 9\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6753376688344173, 0.352442357755117, 0.8514257128564282, 0.5982163205082429 ], "category_id": 1, "smiles": "*C(=O)/C=C(/[1*])CC([2*])(N)O", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 4.6498 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6498 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7476 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1293 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1293 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8906 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7066 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8748 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4521 -8.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9022 -6.0866 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4521 -4.8268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM ISO 2 6 1 9 2\nA 1\nR\nA 6\nR1\nA 9\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.1295647823911956, 0.7011419648084097, 0.2851425712856428, 0.9437969686433488 ], "category_id": 1, "smiles": "*C(=O)/C=C(/[7*])C([H])C([2*])=N", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 4.6256 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8929 -7.3465 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8514 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4712 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5841 -5.2205 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1326 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9068 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1326 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5484 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5484 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9643 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 1 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\nM ISO 2 4 2 7 7\nA 4\nR2\nA 7\nR7\nA 10\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.2926463231615808, 0.8365047818577204, 0.3691845922961481, 0.897636376654183 ], "category_id": 1, "smiles": "CC(O)=O", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 6.5025 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nOAc\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1295647823911956, 0.7011419648084097, 0.2851425712856428, 0.9437969686433488 ], "category_id": 1, "smiles": "*C(=O)/C=C(/[7*])C([H])C([2*])=N", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 4.6256 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8929 -7.3465 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8514 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4712 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5841 -5.2205 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1326 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9068 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1326 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5484 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5484 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9643 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 1 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\nM ISO 2 4 2 7 7\nA 4\nR2\nA 7\nR7\nA 10\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.2926463231615808, 0.8365047818577204, 0.3691845922961481, 0.897636376654183 ], "category_id": 1, "smiles": "CC(O)=O", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 6.5025 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nOAc\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.45372686343171587, 0.6961516305393108, 0.616808404202101, 0.9119835876778426 ], "category_id": 1, "smiles": "*C1(O)C=C([1*])C=C([2*])N1[H]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 4.4428 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4428 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7397 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7397 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0367 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4428 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4428 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1459 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1452 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5528 -6.5591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1459 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 11 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM ISO 2 2 1 5 2\nA 2\nR1\nA 5\nR2\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45372686343171587, 0.6961516305393108, 0.616808404202101, 0.9119835876778426 ], "category_id": 1, "smiles": "*C1(O)C=C([1*])C=C([2*])N1[H]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 4.4428 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4428 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7397 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7397 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0367 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4428 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4428 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1459 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1452 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5528 -6.5591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1459 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 11 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM ISO 2 2 1 5 2\nA 2\nR1\nA 5\nR2\nA 9\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7208604302151076, 0.7329553457739161, 0.8749374687343672, 0.9138549630287548 ], "category_id": 1, "smiles": "*c1cc([1*])cc([2*])n1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 5.4431 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4431 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4333 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4333 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3398 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4431 -7.9764 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5366 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6300 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5366 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 9 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\nM ISO 2 2 1 5 2\nA 2\nR1\nA 5\nR2\nA 8\nR\nM END\n" } ] } ], "Kumada cross-coupling reaction.png": [ { "reactants": [ { "category": "[Txt]", "bbox": [ 0.07003501750875438, 0.04668464790578827, 0.15507753876938468, 0.09021492770983411 ], "category_id": 2, "text": [ "LnPd(Il)" ] }, { "category": "[Txt]", "bbox": [ 0.18309154577288644, 0.042268532563348844, 0.23561780890445222, 0.08642968598774314 ], "category_id": 2, "text": [ "RlM" ] } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.25662831415707854, 0.03091280739707602, 0.42171085542771386, 0.06497998289589449 ], "category_id": 2, "text": [ "transmetallation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.44772386193096547, 0.0037852417220909412, 0.5682841420710355, 0.10661764183889484 ], "category_id": 1, "smiles": "*[1*]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 8.7068 -5.1417 0.0000 R 0 0 0 0 0 0 0 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"category_id": 1, "smiles": "*[Rf+]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.6220 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8583 -4.7480 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\nM CHG 1 2 1\nM RAD 1 2 2\nA 1\nRi+\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.8389194597298649, 0.037852417220909415, 0.9239619809904952, 0.08390619150634919 ], "category_id": 2, "text": [ "LnPd(0)" ] } ] }, { "reactants": [ { "category": "[Txt]", "bbox": [ 0.4947473736868434, 0.21638965177953215, 0.5767883941970986, 0.2618125524446234 ], "category_id": 2, "text": [ "LzPd(0)" ] }, { "category": "[Mol]", "bbox": [ 0.8619309654827414, 0.17727548731792572, 0.9224612306153076, 0.21449703091848668 ], "category_id": 1, "smiles": "**", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.8470 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0292 -4.0394 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nA 1\nR\nA 2\nX\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6423211605802901, 0.3413026286085332, 0.7373686843421711, 0.40249736978233674 ], "category_id": 2, "text": [ "oxidative", "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7468734367183592, 0.512269379722974, 0.8504252126063031, 0.6151017798397779 ], "category_id": 1, "smiles": "*[Pd](*)(*)*", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.5276 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3961 -4.0394 0.0000 Pd 0 0 0 0 0 4 0 0 0 0 0 0\n 12.6923 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7977 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8946 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\nA 1\n*\nA 3\n*\nA 4\n*\nA 5\n*\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7468734367183592, 0.512269379722974, 0.8504252126063031, 0.6151017798397779 ], "category_id": 1, "smiles": "*[Pd](*)(*)*", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.5276 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3961 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"[Txt]", "bbox": [ 0.26413206603301653, 0.6277192522467477, 0.3796898449224612, 0.6908066142815967 ], "category_id": 2, "text": [ "reductive", "elimination" ] } ], "products": [ { "category": "[Txt]", "bbox": [ 0.4947473736868434, 0.21638965177953215, 0.5767883941970986, 0.2618125524446234 ], "category_id": 2, "text": [ "LzPd(0)" ] }, { "category": "[Mol]", "bbox": [ 0.05202601300650325, 0.25424206900044155, 0.11755877938969485, 0.2952488543230934 ], "category_id": 1, "smiles": "*[Rf]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.6805 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7617 -4.7480 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\nA 1\nR\nM END\n" } ] } ], "Lawesson\u2019s reagent.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2256128064032016, 0.20108121070844698, 0.32416208104052024, 0.3488844937932884 ], "category_id": 1, "smiles": "O=C1CCCN1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 1.8053 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 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"[Txt]", "bbox": [ 0.4062031015507754, 0.28701335203684314, 0.6133066533266633, 0.34029127966044875 ], "category_id": 2, "text": [ "Lawesson's reagent" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6963481740870435, 0.20194053212173096, 0.7938969484742371, 0.35146245803314025 ], "category_id": 1, "smiles": "S=C1CCCN1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 1.8528 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7058 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5291 -5.3780 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4406 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7932 -4.4331 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3818 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03551775887943972, 0.48723524133200613, 0.36668334167083544, 0.6960503447600088 ], "category_id": 1, "smiles": "COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1", "molfile": "\n RDKit 2D\n\n 22 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"molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\nM CHG 1 5 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4502251125562781, 0.4416912064279563, 0.6413206603301651, 0.7295638798780834 ], "category_id": 1, "smiles": "COc1ccc([PH](=S)(=S)[Sc])cc1.O=C1CCC[NH+]1", "molfile": "\n RDKit 2D\n\n 18 18 0 0 0 0 0 0 0 0999 V2000\n 0.5374 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5226 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3140 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2992 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0906 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9862 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7776 -1.3622 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7628 -2.9370 0.0000 Sc 0 0 0 0 0 1 0 0 0 0 0 0\n 9.7628 0.2913 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7628 -1.3622 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0906 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2992 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5236 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2697 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1654 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2697 -4.1181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8671 -6.0079 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 9.2254 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 3 12 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 11 1 0\n 7 8 1 0\n 7 9 2 0\n 7 10 2 0\n 11 12 2 0\n 13 14 1 0\n 13 18 1 0\n 14 15 1 0\n 15 16 2 0\n 15 17 1 0\n 17 18 1 0\nM CHG 1 17 1\nM RAD 2 8 2 17 2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.542271135567784, 0.5697300970072665, 0.6413206603301651, 0.7295638798780834 ], "category_id": 1, "smiles": "O=C1CCC[NH-]1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\nM CHG 1 5 -1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.03551775887943972, 0.48723524133200613, 0.36668334167083544, 0.6960503447600088 ], "category_id": 1, "smiles": "COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1", "molfile": "\n RDKit 2D\n\n 22 24 0 0 0 0 0 0 0 0999 V2000\n 0.4290 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9305 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5045 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7915 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3655 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6525 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2264 -2.6220 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2264 -5.2205 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8004 -5.2205 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 17.3744 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.8759 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.4499 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 22.7369 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 25.3109 -5.2205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 26.5979 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.4499 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.8759 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8004 -7.8189 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8004 -2.6220 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2264 -0.1024 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3655 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7915 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 3 22 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 21 1 0\n 7 8 1 0\n 7 19 1 0\n 7 20 2 0\n 8 9 1 0\n 9 10 1 0\n 9 18 2 0\n 9 19 1 0\n 10 11 2 0\n 10 17 1 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\n 13 16 1 0\n 14 15 1 0\n 16 17 2 0\n 21 22 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4502251125562781, 0.4416912064279563, 0.6413206603301651, 0.7295638798780834 ], "category_id": 1, "smiles": "COc1ccc([PH](=S)(=S)[Sc])cc1.O=C1CCC[NH+]1", "molfile": "\n RDKit 2D\n\n 18 18 0 0 0 0 0 0 0 0999 V2000\n 0.5374 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5226 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3140 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2992 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0906 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9862 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7776 -1.3622 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7628 -2.9370 0.0000 Sc 0 0 0 0 0 1 0 0 0 0 0 0\n 9.7628 0.2913 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7628 -1.3622 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0906 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2992 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5236 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2697 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1654 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2697 -4.1181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8671 -6.0079 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 9.2254 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 3 12 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 11 1 0\n 7 8 1 0\n 7 9 2 0\n 7 10 2 0\n 11 12 2 0\n 13 14 1 0\n 13 18 1 0\n 14 15 1 0\n 15 16 2 0\n 15 17 1 0\n 17 18 1 0\nM CHG 1 17 1\nM RAD 2 8 2 17 2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.542271135567784, 0.5697300970072665, 0.6413206603301651, 0.7295638798780834 ], "category_id": 1, "smiles": "O=C1CCC[NH-]1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\nM CHG 1 5 -1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7303651825912957, 0.4941098126382779, 0.9829914957478739, 0.7072215231327004 ], "category_id": 1, "smiles": "COc1ccc(P(=S)([S-])OC2=[NH+]CCC2)cc1", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 0.4804 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7616 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3240 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6052 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1676 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4488 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8511 -2.2283 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4135 -2.2283 0.0000 S 0 0 0 0 0 1 0 0 0 0 0 0\n 13.1323 -4.5118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.6946 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4135 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0149 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4172 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.0969 -5.0630 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 13.1323 -0.1024 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1676 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6052 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 3 17 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 16 1 0\n 7 8 1 0\n 7 9 1 0\n 7 15 2 0\n 9 10 1 0\n 10 11 1 0\n 10 14 2 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\n 16 17 2 0\nM CHG 2 8 -1 14 1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7303651825912957, 0.4941098126382779, 0.9829914957478739, 0.7072215231327004 ], "category_id": 1, "smiles": "COc1ccc(P(=S)([S-])OC2=[NH+]CCC2)cc1", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 0.4804 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7616 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3240 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6052 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1676 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4488 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8511 -2.2283 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4135 -2.2283 0.0000 S 0 0 0 0 0 1 0 0 0 0 0 0\n 13.1323 -4.5118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.6946 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4135 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0149 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4172 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.0969 -5.0630 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 13.1323 -0.1024 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1676 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6052 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 3 17 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 16 1 0\n 7 8 1 0\n 7 9 1 0\n 7 15 2 0\n 9 10 1 0\n 10 11 1 0\n 10 14 2 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\n 16 17 2 0\nM CHG 2 8 -1 14 1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.21410705352676337, 0.7871384145681088, 0.46323161580790395, 0.940097626132654 ], "category_id": 1, "smiles": "COc1ccc([PH](O)(S)SC2CCCN2)cc1", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 0.6665 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6659 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2205 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9978 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5523 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3296 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.8841 -4.0394 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 19.9944 -2.3858 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 21.7717 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 24.2154 -2.8583 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 27.3256 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 27.1035 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.5489 -8.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.8841 -0.5748 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 18.6614 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5523 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9978 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 3 17 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 16 1 0\n 7 8 1 0\n 7 14 1 0\n 7 15 1 0\n 8 9 1 0\n 9 10 1 0\n 9 13 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 16 17 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.21410705352676337, 0.7871384145681088, 0.46323161580790395, 0.940097626132654 ], "category_id": 1, "smiles": "COc1ccc([PH](O)(S)SC2CCCN2)cc1", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 0.6665 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6659 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2205 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9978 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5523 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3296 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.8841 -4.0394 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 19.9944 -2.3858 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 21.7717 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 24.2154 -2.8583 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 27.3256 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 27.1035 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 23.5489 -8.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.8841 -0.5748 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 18.6614 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5523 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9978 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 3 17 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 16 1 0\n 7 8 1 0\n 7 14 1 0\n 7 15 1 0\n 8 9 1 0\n 9 10 1 0\n 9 13 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 16 17 2 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5592796398199099, 0.7974502715275162, 0.655327663831916, 0.9478315188522096 ], "category_id": 1, "smiles": "S=C1CCCN1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 1.7060 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6824 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4121 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1417 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4685 -4.3543 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1181 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7003501750875438, 0.7768265576087012, 0.886943471735868, 0.9478315188522096 ], "category_id": 1, "smiles": "COc1ccc([PH](=O)(=O)[S-])cc1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 0.5901 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2130 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4588 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9341 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1799 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8027 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9010 -2.9370 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 16.5238 -5.6929 0.0000 S 0 0 0 0 0 1 0 0 0 0 0 0\n 16.5238 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.5238 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1799 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9341 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 3 12 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 11 1 0\n 7 8 1 0\n 7 9 2 0\n 7 10 2 0\n 11 12 2 0\nM CHG 1 8 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.21410705352676337, 0.7871384145681088, 0.46323161580790395, 0.940097626132654 ], "category_id": 1, "smiles": "COc1ccc([PH](O)(S)SC2CCCN2)cc1", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 0.6665 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6659 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2205 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9978 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5523 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3296 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.8841 -4.0394 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 19.9944 -2.3858 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 21.7717 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 24.2154 -2.8583 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 27.3256 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 27.1035 -7.5827 0.0000 C 0 0 0 0 0 0 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0.632816408204102, 0.3549970778269394 ], "category_id": 1, "smiles": "[1*]C([2*])(O)N([3*])[4*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 3.6510 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6510 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0318 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6510 -3.1732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0321 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0321 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4132 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 4 2 2 3 1 6 4 7 3\nA 2\nR2\nA 3\nR1\nA 6\nR4\nA 7\nR3\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.6483241620810405, 0.15322062325661212, 0.7198599299649825, 0.22767289793764198 ], "category_id": 1, "smiles": "[I-]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 10.5512 -4.0394 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\nM CHG 1 1 -1\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7413706853426714, 0.12300810599474495, 0.8449224612306153, 0.31831044972324346 ], "category_id": 1, "smiles": "[2*]C([7*])=N([3*])[4*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 3.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 3\n 4 5 1 0\n 4 6 1 0\nM ISO 4 2 2 3 7 5 3 6 4\nA 2\nR2\nA 3\nR7\nA 5\nR3\nA 6\nR4\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7413706853426714, 0.12300810599474495, 0.8449224612306153, 0.31831044972324346 ], "category_id": 1, "smiles": "[2*]C([7*])=N([3*])[4*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 3.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 3.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 3\n 4 5 1 0\n 4 6 1 0\nM ISO 4 2 2 3 7 5 3 6 4\nA 2\nR2\nA 3\nR7\nA 5\nR3\nA 6\nR4\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.49724862431215605, 0.06474110841828681, 0.632816408204102, 0.3549970778269394 ], "category_id": 1, "smiles": "[1*]C([2*])(O)N([3*])[4*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 3.6510 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6510 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0318 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6510 -3.1732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0321 -5.5354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0321 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4132 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 4 2 2 3 1 6 4 7 3\nA 2\nR2\nA 3\nR1\nA 6\nR4\nA 7\nR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.19259629814907453, 0.5578525508709048, 0.3266633316658329, 0.8729259451732339 ], "category_id": 1, "smiles": "[1*]C([2*])([2*])=N([3*])([4*])[H]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.2010 3.3481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8481 2.7990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 2 3\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 5 2 1 3 2 4 2 7 3 8 4\nA 2\nR1\nA 3\nR2\nA 4\nR2\nA 7\nR3\nA 8\nR4\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.3381690845422711, 0.6376999179201251, 0.4117058529264632, 0.7121521926011549 ], "category_id": 1, "smiles": "[Co]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 10.8661 -3.4094 0.0000 Co 0 0 0 0 0 15 0 0 0 0 0 0\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4512256128064032, 0.6107244560791723, 0.5847923961980991, 0.7995526889658422 ], "category_id": 1, "smiles": "[1*]C([2*])([H])N([3*])([4*])[H]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7990 -1.8481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3481 0.2010 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 4 3 1 4 2 7 3 8 4\nA 3\nR1\nA 4\nR2\nA 7\nR3\nA 8\nR4\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4512256128064032, 0.6107244560791723, 0.5847923961980991, 0.7995526889658422 ], "category_id": 1, "smiles": "[1*]C([2*])([H])N([3*])([4*])[H]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7990 -1.8481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3481 0.2010 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 4 3 1 4 2 7 3 8 4\nA 3\nR1\nA 4\nR2\nA 7\nR3\nA 8\nR4\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.6078039019509754, 0.6031713267637054, 0.6728364182091046, 0.7035200448120501 ], "category_id": 1, "smiles": "[H]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 8.1304 -5.8504 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7233616808404202, 0.5923811420273244, 0.8284142071035517, 0.7844464303349086 ], "category_id": 1, "smiles": "[1*]C([2*])N([3*])[4*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.7729 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1165 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6564 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3617 -4.2756 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2022 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2022 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 1 0\nM ISO 4 2 2 3 1 5 4 6 3\nA 2\nR2\nA 3\nR1\nA 5\nR4\nA 6\nR3\nM END\n" } ] } ], "Lossen rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.060530265132566284, 0.09838525820287192, 0.23611805902951477, 0.3510288842053085 ], "category_id": 1, "smiles": "[2*]C(=O)ON([H])C(=O)[Rf]", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 4.2423 -3.0945 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"[1*]C(=O)NCC([2*])=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 9.0044 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5604 -4.7480 0.0000 N 0 0 0 0 0 2 0 0 0 0 0 0\n 4.1163 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5436 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1163 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5771 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1498 -3.1732 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5771 -7.6614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\n 6 8 2 0\nM RAD 1 2 2\nM ISO 2 4 1 7 2\nA 4\nR1\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3071535767883942, 0.17733639132863332, 0.4827413706853427, 0.4372678142349863 ], "category_id": 1, "smiles": "[1*]C(=O)NCC([2*])=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 9.0044 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5604 -4.7480 0.0000 N 0 0 0 0 0 2 0 0 0 0 0 0\n 4.1163 -3.0945 0.0000 C 0 0 0 0 0 0 0 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0.6935850508424467 ], "category_id": 1, "smiles": "CCO[C@@H]([C@@H](O)C=C/C=C/CCOC(C)=O)P(=O)(OCC)OCC", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 19.8554 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.3982 -2.3071 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0\n 20.5841 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.3982 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 16.3944 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3906 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.3944 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.3982 -6.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3906 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5690 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5653 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5615 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7399 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7362 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9146 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\n 2 5 1 0\n 5 7 1 0\n 7 8 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 1 0\n 14 15 1 0\n 5 6 1 6\n 7 9 1 1\nA 1\nOEt\nA 3\nOEt\nA 6\nEtO\nA 15\nAcO\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.03451725862931466, 0.7477407979919509, 0.42671335667833915, 0.940222067981153 ], "category_id": 1, "smiles": "CCOC(OCC)[C@H]1[C@H](C=C/C=C/CCOC(C)=O)OP1(O)O", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 3.1398 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4423 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5354 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6286 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7218 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0243 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1175 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.2106 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 20.7224 -6.5591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 20.7224 -4.1969 0.0000 P 0 0 0 0 0 4 0 0 0 0 0 0\n 20.7224 -1.6772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 20.7224 -1.6772 0.0000 O 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"*C(*)(*)[3H].*C(*)(*)[3H].[2H]C#C", "molfile": "\n RDKit 2D\n\n 13 10 0 0 0 0 0 0 0 0999 V2000\n 3.2788 -5.3780 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 6.2063 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2063 -8.0551 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 6.2063 -2.8583 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 11.5930 -5.3780 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2063 -8.0551 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 6.2063 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2788 -5.3780 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 6.2063 -2.8583 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 11.5930 -5.3780 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6655 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4127 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8718 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 11 12 1 0\n 12 13 3 0\nM ISO 8 1 1 3 2 4 3 5 3 6 2 8 1 9 2 10 3\nM ISO 1 11 2\nA 1\n1*\nA 3\n2*\nA 4\n3*\nA 6\n2*\nA 8\n1*\nA 9\n2*\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6568284142071036, 0.2316259375793816, 0.8049024512256128, 0.297062861648893 ], "category_id": 2, "text": [ "homocoupling" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.04202101050525263, 0.607628580645463, 0.22611305652826413, 0.8756083649301286 ], "category_id": 1, "smiles": "*#C.*C(*)(O[Ti])C(*)([1*])O[Ti]", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 14.1803 -5.3780 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 10.6073 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6073 -8.0551 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 10.6073 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6073 -0.2598 0.0000 Ti 0 0 0 0 0 1 0 0 0 0 0 0\n 7.1460 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1460 -8.0551 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 3.5730 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1460 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1460 -0.2598 0.0000 Ti 0 0 0 0 0 1 0 0 0 0 0 0\n 0.0000 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5730 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 11 12 3 0\nM ISO 4 1 1 3 2 7 2 8 1\nA 1\n1*\nA 3\n2*\nA 7\n2*\nA 8\nR1\nA 11\nZ\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04202101050525263, 0.607628580645463, 0.22611305652826413, 0.8756083649301286 ], "category_id": 1, "smiles": "*#C.*C(*)(O[Ti])C(*)([1*])O[Ti]", "molfile": "\n RDKit 2D\n\n 12 10 0 0 0 0 0 0 0 0999 V2000\n 14.1803 -5.3780 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 10.6073 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6073 -8.0551 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 10.6073 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6073 -0.2598 0.0000 Ti 0 0 0 0 0 1 0 0 0 0 0 0\n 7.1460 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1460 -8.0551 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 3.5730 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1460 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1460 -0.2598 0.0000 Ti 0 0 0 0 0 1 0 0 0 0 0 0\n 0.0000 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5730 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 11 12 3 0\nM ISO 4 1 1 3 2 7 2 8 1\nA 1\n1*\nA 3\n2*\nA 7\n2*\nA 8\nR1\nA 11\nZ\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.27613806903451726, 0.6117833059832097, 0.4612306153076538, 0.877685727599002 ], "category_id": 1, "smiles": "*#C.*C(*)C(*)(*)O[Ti]", "molfile": "\n RDKit 2D\n\n 10 8 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -5.6929 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 4.7556 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7556 -9.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 9.6245 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3802 -5.6929 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 9.6245 -9.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 9.6245 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6245 -0.2598 0.0000 Ti 0 0 0 0 0 1 0 0 0 0 0 0\n 0.0000 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7556 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 8 1 0\n 9 10 3 0\nM ISO 4 1 1 3 2 5 1 6 2\nA 1\n1*\nA 3\n2*\nA 5\n1*\nA 6\n2*\nA 9\nZ\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.27613806903451726, 0.6117833059832097, 0.4612306153076538, 0.877685727599002 ], "category_id": 1, "smiles": "*.*.*.*C(*)C(*)(*)O[Ti]", "molfile": "\n RDKit 2D\n\n 11 7 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -5.6929 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 4.7556 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7556 -9.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 9.6245 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3802 -5.6929 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 9.6245 -9.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 9.6245 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6245 -0.2598 0.0000 Ti 0 0 0 0 0 1 0 0 0 0 0 0\n 0.0000 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7556 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 8 1 0\nM ISO 4 1 1 3 2 5 1 6 2\nA 1\n1*\nA 3\n2*\nA 5\n1*\nA 6\n2*\nA 9\nZ\nA 10\nZ\nA 11\nZ\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5322661330665333, 0.6689107793772276, 0.6373186593296648, 0.8558734195758316 ], "category_id": 1, "smiles": "[1*]/C([2*])=C(/[2*])[7*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.7601 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1093 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1093 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3367 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0792 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0792 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 4 6 1 0\nM ISO 4 2 2 3 1 5 2 6 7\nA 2\nR2\nA 3\nR1\nA 5\nR2\nA 6\nR7\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.6778389194597298, 0.6928004500692714, 0.8619309654827414, 0.8195195728705474 ], "category_id": 1, "smiles": "C#C[Ti]1=O=C1(=O)[Zr]", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8302 -1.1491 0.0000 Zr 0 0 0 0 0 1 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 Ti 0 0 0 0 0 4 0 0 0 0 0 0\n -1.1830 2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6830 2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8302 1.1491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 2 0\n 1 7 2 0\n 3 4 1 0\n 3 6 2 0\n 4 5 3 0\nM END\n" } ] } ], "Meerwein\u2013Ponndorf\u2013Verley reduction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0240120060030015, 0.06924808558125216, 0.21560780390195097, 0.4655010197406395 ], "category_id": 1, "smiles": "*.CC.[1*]C([2*])=O", "molfile": "\n RDKit 2D\n\n 7 4 0 0 0 0 0 0 0 0999 V2000\n 3.2111 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1677 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2545 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2111 -4.5118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9251 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9685 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9356 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 5 6 1 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nA 7\nAl(OiPr)3\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.19859929964982492, 0.2103090006541732, 0.33166583291645824, 0.27314522645938355 ], "category_id": 2, "text": [ "coordination" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.38819409704852426, 0.13977854311771268, 0.6003001500750376, 0.4334417208604302 ], "category_id": 1, "smiles": "CCC*[Al]1(*CCC)OC(C)(C)O1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 10.9025 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8098 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9025 -3.8031 0.0000 Al 0 0 0 0 0 4 0 0 0 0 0 0\n 13.8098 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.8625 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3035 -6.6378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2508 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5064 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2508 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8498 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 6 1 0\n 3 10 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM RAD 1 3 2\nA 1\nOiPr\nA 2\nPr\nA 4\nOi\nA 5\nPr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.38819409704852426, 0.13977854311771268, 0.6003001500750376, 0.4334417208604302 ], "category_id": 1, "smiles": "CCC*[Al]1(*CCC)OC(C)(C)O1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 10.9025 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8098 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9025 -3.8031 0.0000 Al 0 0 0 0 0 4 0 0 0 0 0 0\n 13.8098 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.8625 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3035 -6.6378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2508 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5064 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2508 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8498 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 6 1 0\n 3 10 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM RAD 1 3 2\nA 1\nOiPr\nA 2\nPr\nA 4\nOi\nA 5\nPr\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7298649324662331, 0.07565994535729403, 0.8814407203601801, 0.4655010197406395 ], "category_id": 1, "smiles": "*[Al](OC(C)C)(OC([H])(C)C)O=C([1*])[2*]", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 Al 0 0 0 0 0 4 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5490 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0490 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5490 0.9510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5490 -2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 4.6471 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7990 3.3481 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 9 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 9 10 2 3\n 10 11 1 0\n 10 12 1 0\nM ISO 2 11 2 12 1\nA 1\ni-PrO\nA 3\nOi-Pr\nA 11\nR2\nA 12\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7298649324662331, 0.07565994535729403, 0.8814407203601801, 0.4655010197406395 ], "category_id": 1, "smiles": "*[Al](OC(C)C)(OC([H])(C)C)O=C([1*])[2*]", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 Al 0 0 0 0 0 4 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5490 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0490 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5490 0.9510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5490 -2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 4.6471 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7990 3.3481 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 9 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 9 10 2 3\n 10 11 1 0\n 10 12 1 0\nM ISO 2 11 2 12 1\nA 1\ni-PrO\nA 3\nOi-Pr\nA 11\nR2\nA 12\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.10305152576288144, 0.7258225266479393, 0.19759879939969985, 0.8053295878708584 ], "category_id": 2, "text": [ "hydride" ] }, { "category": "[Txt]", "bbox": [ 0.10305152576288144, 0.8668834417208604, 0.19909954977488745, 0.9386962712125293 ], "category_id": 2, "text": [ "transfer" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.23711855927963982, 0.7309520144687728, 0.3141570785392696, 0.931002039481279 ], "category_id": 1, "smiles": "CC(C)=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 0.9296 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9581 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9865 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9581 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.40220110055027514, 0.69376322776773, 0.5942971485742872, 0.9669084542271135 ], "category_id": 1, "smiles": "*OC([1*])[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 4.8444 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7098 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9790 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8444 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8365 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nA 5\nAl(OiPr)2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.23711855927963982, 0.7309520144687728, 0.3141570785392696, 0.931002039481279 ], "category_id": 1, "smiles": "CC(C)=O", "molfile": "\n RDKit 2D\n\n 4 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0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 6\n 2 3 1 0\n 2 4 2 0\n 4 5 1 0\n 4 13 2 0\n 5 6 1 0\n 5 12 1 0\n 6 7 1 0\n 7 8 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\n 13 15 1 1\nA 8\nMe\nA 9\nPh\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5202601300650325, 0.17826239852599565, 0.7268634317158579, 0.8516981262908682 ], "category_id": 1, "smiles": "*[Li](OC)N1(C=C([H])C)C(C(OC=C([H])C)c2ccccc2)CO[Li]12**2.CC", "molfile": "\n RDKit 2D\n\n 24 24 0 0 0 0 0 0 0 0999 V2000\n 4.0742 1.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7752 2.1203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9681 2.8938 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4761 1.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.1771 2.1203 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0588 3.3338 0.0000 Li 0 0 0 0 0 3 0 0 0 0 0 0\n 0.6203 4.7683 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5506 3.1771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4322 4.3906 0.0000 R 0 0 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0\n 22 23 1 0\n 22 24 1 0\n 23 24 1 0\nA 7\nX\nA 9\nMe\nA 18\nPh\nA 23\nX\nA 24\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5202601300650325, 0.17826239852599565, 0.7268634317158579, 0.8516981262908682 ], "category_id": 1, "smiles": "*[Li](OC)N1(C=C([H])C)C(C(OC=C([H])C)c2ccccc2)CO[Li]12**2.CC", "molfile": "\n RDKit 2D\n\n 24 24 0 0 0 0 0 0 0 0999 V2000\n 4.0742 1.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7752 2.1203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9681 2.8938 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4761 1.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.1771 2.1203 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0588 3.3338 0.0000 Li 0 0 0 0 0 3 0 0 0 0 0 0\n 0.6203 4.7683 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5506 3.1771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4322 4.3906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0742 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3732 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.8943 9.3627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0511 7.8709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.4214 7.2608 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8376 6.9893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.9944 5.4975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7808 4.6158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5049 5.3884 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9376 3.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2367 2.3740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.9248 0.9068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 Li 0 0 0 0 0 4 0 0 0 0 0 0\n 0.8660 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 1\n 2 3 1 0\n 2 4 2 3\n 4 5 1 0\n 5 6 1 0\n 5 19 1 6\n 5 22 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 10 11 1 0\n 12 13 1 0\n 13 14 1 0\n 13 15 2 3\n 15 16 1 0\n 16 17 1 0\n 17 18 1 0\n 17 19 1 0\n 19 20 1 0\n 20 21 1 0\n 21 22 1 0\n 22 23 1 0\n 22 24 1 0\n 23 24 1 0\nA 7\nX\nA 9\nMe\nA 18\nPh\nA 23\nX\nA 24\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.28264132066033015, 0.19586856134337793, 0.49224612306153076, 0.8825089112212872 ], "category_id": 1, "smiles": "[H][CH](C)=C1=C([H])(C)=C(OCc2ccccc2)N1[Li]OC", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 3.3107 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5607 0.0000 0.0000 C 0 0 0 0 0 5 0 0 0 0 0 0\n 3.3107 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0607 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -1.0607 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -2.5607 0.0000 Li 0 0 0 0 0 2 0 0 0 0 0 0\n -1.2990 -3.3107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2990 -4.8107 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8107 1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.3107 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5607 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0607 2.1213 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 6\n 2 3 1 0\n 2 4 2 0\n 4 5 1 0\n 4 13 2 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"[Mol]", "bbox": [ 0.7713856928464232, 0.16725854676513174, 0.9774887443721861, 0.8715050594604232 ], "category_id": 1, "smiles": "*[C@]([H])(C)C1=N[C@H](COC)C(c2ccccc2)O1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 2.2337 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2491 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6245 -4.9055 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2491 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2797 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9905 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3257 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8334 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0365 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0518 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5441 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1687 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1073 -3.8819 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 5 13 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 2 1 1 6\n 2 3 1 1\n 9 13 1 1\nA 4\nR\nA 8\nPh\nA 12\nMe\nM END\n" } ] } ], "Meyer\u2013Schuster rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.11455727863931967, 0.15564206085912335, 0.2786393196598299, 0.5083355382187882 ], "category_id": 1, "smiles": "*C(*)(O)C#C[1*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 3.7886 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1576 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1576 -1.6772 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7886 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3144 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9453 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4711 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 3 0\n 6 7 1 0\nM ISO 1 7 1\nA 2\nR\nA 3\nR\nA 7\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3136568284142071, 0.20276305176142675, 0.3616808404202101, 0.3341306627617877 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.40970485242621313, 0.08567452891327891, 0.5722861430715358, 0.5111913558492308 ], "category_id": 1, "smiles": "*C(*)(O)C#C[1*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 3.0184 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9486 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9486 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0184 -1.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0019 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0716 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0551 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 3 0\n 6 7 1 0\nM ISO 1 7 1\nA 2\nR\nA 3\nR\nA 7\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.40970485242621313, 0.08567452891327891, 0.5722861430715358, 0.5111913558492308 ], "category_id": 1, "smiles": "*C(*)(O)C#C[1*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 3.0184 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9486 -5.2205 0.0000 R 0 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0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 14 15 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.30965482741370687, 0.14897342288165358, 0.35317658829414705, 0.24474205187700232 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3711855927963982, 0.018917260048463946, 0.5712856428214107, 0.4350969811146709 ], "category_id": 1, "smiles": "C[S-]O.[H]N(=C=NC1CCCCC1)C1CCCCC1", "molfile": "\n RDKit 2D\n\n 19 19 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.5000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -8.2500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 6.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 6.9462 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 6.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 16 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 15 1 0\n 5 6 2 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 14 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\n 15 16 1 0\n 17 18 1 0\n 18 19 1 0\nM CHG 1 18 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3711855927963982, 0.018917260048463946, 0.5712856428214107, 0.4350969811146709 ], "category_id": 1, "smiles": "C[S-]O.[H]N(=C=NC1CCCCC1)C1CCCCC1", "molfile": "\n RDKit 2D\n\n 19 19 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.5000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -8.2500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 6.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 6.9462 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 6.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 16 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 15 1 0\n 5 6 2 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 14 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\n 15 16 1 0\n 17 18 1 0\n 18 19 1 0\nM CHG 1 18 -1\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.4897448724362181, 0.3003115032693652, 0.567783891945973, 0.5024897200373236 ], "category_id": 1, "smiles": "C[Se](C)[O]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 4.9741 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9741 -4.6693 0.0000 Se 0 0 0 0 0 3 0 0 0 0 0 0\n 1.7054 -2.8583 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 8.2428 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\nM RAD 2 2 2 3 2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6368184092046023, 0.011823287530289968, 0.8374187093546773, 0.42563835109043885 ], "category_id": 1, "smiles": "C[Se](C)(C)O/C(=N/C1CCCCC1)NC1CCCCC1", "molfile": "\n RDKit 2D\n\n 20 21 0 0 0 0 0 0 0 0999 V2000\n 8.7354 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1144 -6.7953 0.0000 Se 0 0 0 0 0 4 0 0 0 0 0 0\n 5.6735 -5.7717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6735 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8724 -4.0394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9719 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8724 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9719 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2608 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3602 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2608 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3846 -4.0394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2852 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3846 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2852 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9962 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8968 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9962 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1144 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7354 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 19 1 0\n 2 20 1 0\n 3 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 1 0\n 6 7 1 0\n 6 11 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 12 13 1 0\n 13 14 1 0\n 13 18 1 0\n 14 15 1 0\n 15 16 1 0\n 16 17 1 0\n 17 18 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6368184092046023, 0.011823287530289968, 0.8374187093546773, 0.42563835109043885 ], "category_id": 1, "smiles": "C[Se](C)(C)O/C(=N/C1CCCCC1)NC1CCCCC1", "molfile": "\n RDKit 2D\n\n 20 21 0 0 0 0 0 0 0 0999 V2000\n 8.7354 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1144 -6.7953 0.0000 Se 0 0 0 0 0 4 0 0 0 0 0 0\n 5.6735 -5.7717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6735 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8724 -4.0394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9719 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8724 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9719 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2608 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3602 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2608 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3846 -4.0394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2852 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3846 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2852 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9962 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8968 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9962 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1144 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7354 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 19 1 0\n 2 20 1 0\n 3 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 1 0\n 6 7 1 0\n 6 11 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 12 13 1 0\n 13 14 1 0\n 13 18 1 0\n 14 15 1 0\n 15 16 1 0\n 16 17 1 0\n 17 18 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7998999499749875, 0.31449944830571314, 0.8914457228614308, 0.5426888976403096 ], "category_id": 1, "smiles": "[1*]C([2*])O[H]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 4.5421 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4892 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2227 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5421 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7015 -0.3386 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.0750375187593797, 0.6207225953402233, 0.3046523261630815, 0.8630999897111677 ], "category_id": 1, "smiles": "O=C(NC1CCCCC1)NC1CCCCC1", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 0.5309 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1853 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8398 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8398 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4942 -5.9291 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1486 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8031 -5.9291 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4575 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4575 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1119 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.7664 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.7664 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1119 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1486 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1853 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5309 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 16 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 15 1 0\n 5 6 1 0\n 6 7 1 0\n 6 14 2 0\n 7 8 1 0\n 8 9 1 0\n 8 13 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 15 16 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.32066033016508255, 0.5734294452190635, 0.45872936468234116, 0.8607353322051097 ], "category_id": 1, "smiles": "[1*]C([2*])O[Si](C)C([H])([H])[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 3.8236 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9578 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7784 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8236 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5132 -2.0709 0.0000 Si 0 0 0 0 0 3 0 0 0 0 0 0\n 4.8907 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9141 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6254 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6925 -0.9685 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3150 -3.4094 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM RAD 1 5 2\nM ISO 2 2 2 3 1\nA 2\nR2\nA 3\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0750375187593797, 0.6207225953402233, 0.3046523261630815, 0.8630999897111677 ], "category_id": 1, "smiles": "O=C(NC1CCCCC1)NC1CCCCC1", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 0.5309 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1853 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8398 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8398 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4942 -5.9291 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1486 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8031 -5.9291 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4575 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4575 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1119 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.7664 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.7664 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 19.1119 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1486 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1853 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5309 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 16 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 15 1 0\n 5 6 1 0\n 6 7 1 0\n 6 14 2 0\n 7 8 1 0\n 8 9 1 0\n 8 13 1 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 15 16 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.32066033016508255, 0.5734294452190635, 0.45872936468234116, 0.8607353322051097 ], "category_id": 1, "smiles": "[1*]C([2*])O[Si](C)C([H])([H])[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 3.8236 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9578 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7784 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8236 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5132 -2.0709 0.0000 Si 0 0 0 0 0 3 0 0 0 0 0 0\n 4.8907 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9141 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6254 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6925 -0.9685 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3150 -3.4094 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM RAD 1 5 2\nM ISO 2 2 2 3 1\nA 2\nR2\nA 3\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4932466233116558, 0.6041699927978174, 0.5342671335667833, 0.723585196853746 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5532766383191596, 0.5781587602311794, 0.6743371685842922, 0.8642823184641966 ], "category_id": 1, "smiles": "[1*]C([2*])([H])O[Si](C)C", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 3.9370 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7717 -6.3228 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7323 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0630 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6693 -2.1496 0.0000 Si 0 0 0 0 0 3 0 0 0 0 0 0\n 5.0394 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8976 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\nM RAD 1 6 2\nM ISO 2 3 1 4 2\nA 3\nR1\nA 4\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5532766383191596, 0.5781587602311794, 0.6743371685842922, 0.8642823184641966 ], "category_id": 1, "smiles": "[1*]C([2*])([H])O[Si](C)C", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 3.9370 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7717 -6.3228 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7323 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0630 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6693 -2.1496 0.0000 Si 0 0 0 0 0 3 0 0 0 0 0 0\n 5.0394 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8976 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\nM RAD 1 6 2\nM ISO 2 3 1 4 2\nA 3\nR1\nA 4\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7583791895947974, 0.6219049240932523, 0.8504252126063031, 0.8063482095657758 ], "category_id": 1, "smiles": "[1*]C([2*])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.5544 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0366 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9796 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5544 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.8819409704852427, 0.701120950546195, 0.968984492246123, 0.7909779357763989 ], "category_id": 2, "text": [ "(CH3)2S" ] } ] } ], "Morgan\u2013Walls reaction.png": [ { "reactants": [ { "category": "[Mol]", 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16 2 0\n 17 18 2 0\nM ISO 1 2 1\nA 2\nR1\nA 10\nR\nA 12\nPOCl2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.12706353176588295, 0.6066268428331814, 0.4227113556778389, 0.9404996615955038 ], "category_id": 1, "smiles": "*C1(OP(Cl)Cl)Nc2ccccc2C2C=CC([1*])=CC21[H]", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n 3.6901 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2724 -6.4803 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8353 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2529 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3981 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8157 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0882 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8157 -2.4646 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3981 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3981 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3622 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2529 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2170 -3.3307 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 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0.3931965982991496, 0.6327021417507837, 0.5532766383191596 ], "category_id": 1, "smiles": "COC(=O)C=CCN(C(C)=O)c1ccccc1*Br.[I-]", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 5.1626 -6.2441 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1626 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4748 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9856 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3971 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3971 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9856 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4748 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4748 -1.6772 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7727 0.1339 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7511 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7511 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3396 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3396 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2116 -3.3307 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 11 1 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\nM CHG 1 15 -1\nA 2\nAc\nA 9\nPdLn\nA 14\nCO2Me\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.42791449200536097, 0.3931965982991496, 0.6327021417507837, 0.5532766383191596 ], "category_id": 1, "smiles": "COC(=O)C=CCN(C(C)=O)c1ccccc1*Br.[I-]", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 5.1626 -6.2441 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1626 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4748 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9856 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3971 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3971 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9856 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4748 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4748 -1.6772 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7727 0.1339 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7511 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7511 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3396 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3396 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2116 -3.3307 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 11 1 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\nM CHG 1 15 -1\nA 2\nAc\nA 9\nPdLn\nA 14\nCO2Me\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6245513895221102, 0.4432216108054027, 0.7142096640375191, 0.47223611805902954 ], "category_id": 2, "text": [ "insertion" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.734586544609203, 0.3936968484242121, 0.961788762983478, 0.545272636318159 ], "category_id": 1, "smiles": "*C(C(OC)OC)C1([H])CN(C(C)=O)c2ccccc21", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 8.1589 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6252 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6066 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2265 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2079 -3.7244 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8464 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0980 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3497 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3497 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0980 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8464 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4781 -6.0866 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4781 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2265 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 14 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 1 0\n 12 14 1 0\nA 1\nMeO2C\nA 3\nPdBrL7\nA 13\nAc\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.734586544609203, 0.3936968484242121, 0.961788762983478, 0.545272636318159 ], "category_id": 1, "smiles": "*C(C(OC)OC)C1([H])CN(C(C)=O)c2ccccc21", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 8.1589 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6252 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6066 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2265 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2079 -3.7244 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8464 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0980 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3497 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3497 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0980 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8464 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4781 -6.0866 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4781 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2265 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 14 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 1 0\n 12 14 1 0\nA 1\nMeO2C\nA 3\nPdBrL7\nA 13\nAc\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.23993776873157738, 0.5712856428214107, 0.3474258137472097, 0.6038019009504753 ], "category_id": 2, "text": [ "B-hydride" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3932737950334984, 0.5992996498249125, 0.5007618400491307, 0.6333166583291646 ], "category_id": 1, "smiles": "*[H]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.1001 -3.5669 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1620 -3.5669 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nA 2\nPdBr\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5216481426351066, 0.567783891945973, 0.7488503610093817, 0.6838419209604802 ], "category_id": 1, "smiles": "COC(=O)C=C1CN(C(C)=O)c2ccccc21", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 7.1463 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1463 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8656 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7369 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4561 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4561 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7369 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8656 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2750 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0996 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5324 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2750 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 12 1 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 9 12 1 0\n 10 11 1 0\nA 2\nAc\nA 11\nCO2Me\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3932737950334984, 0.5992996498249125, 0.5007618400491307, 0.6333166583291646 ], "category_id": 1, "smiles": "*[H]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.1001 -3.5669 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1620 -3.5669 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nA 2\nPdBr\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5216481426351066, 0.567783891945973, 0.7488503610093817, 0.6838419209604802 ], "category_id": 1, "smiles": "COC(=O)C=C1CN(C(C)=O)c2ccccc21", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 7.1463 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1463 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8656 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7369 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4561 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4561 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7369 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8656 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2750 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0996 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5324 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2750 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 12 1 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 9 12 1 0\n 10 11 1 0\nA 2\nAc\nA 11\nCO2Me\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7356053886377872, 0.5942971485742872, 0.8181317549531067, 0.6213106553276638 ], "category_id": 2, "text": [ "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.10595977897275605, 0.6983491745872936, 0.33367141936132316, 0.8159079539769885 ], "category_id": 1, "smiles": "*C1(CC(=O)OC)c2ccccc2N(C(C)=O)C1[H]", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 7.0566 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0566 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9546 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7025 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6006 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6006 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7025 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9546 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3087 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5608 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1104 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5126 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3087 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5608 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 1 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 13 1 0\n 11 12 1 0\n 13 14 1 0\nA 2\nAc\nA 10\nPdBrL7\nA 12\nCO2Me\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.10595977897275605, 0.6983491745872936, 0.33367141936132316, 0.8159079539769885 ], "category_id": 1, "smiles": "*C1(CC(=O)OC)c2ccccc2N(C(C)=O)C1[H]", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 7.0566 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0566 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9546 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7025 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6006 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6006 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7025 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9546 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3087 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5608 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1104 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5126 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3087 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5608 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 13 1 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 13 1 0\n 11 12 1 0\n 13 14 1 0\nA 2\nAc\nA 10\nPdBrL7\nA 12\nCO2Me\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3387656395042441, 0.751375687843922, 0.44931021660562903, 0.7778889444722361 ], "category_id": 2, "text": [ "elimination" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4666305650915603, 0.6963481740870435, 0.6968893155515878, 0.8129064532266133 ], "category_id": 1, "smiles": "COC(=O)C=C1CN(C(C)=O)c2ccccc21.C[I-]", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.4437 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1522 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3189 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3189 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0274 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0274 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8886 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7498 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4583 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4583 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7498 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8886 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.2629 -3.6457 0.0000 I 0 0 0 0 0 1 0 0 0 0 0 0\n 19.0962 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 3 12 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 13 14 1 0\nM CHG 1 13 -1\nM RAD 1 13 2\nA 1\nCO2Me\nA 6\nAc\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4666305650915603, 0.6963481740870435, 0.6968893155515878, 0.8129064532266133 ], "category_id": 1, "smiles": "COC(=O)C=C1CN(C(C)=O)c2ccccc21.C[I-]", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 13.4437 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1522 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3189 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3189 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0274 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0274 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8886 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7498 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4583 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4583 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7498 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8886 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.2629 -3.6457 0.0000 I 0 0 0 0 0 1 0 0 0 0 0 0\n 19.0962 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 3 12 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 13 14 1 0\nM CHG 1 13 -1\nM RAD 1 13 2\nA 1\nCO2Me\nA 6\nAc\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7417184528092923, 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"bbox": [ 0.2103912919026358, 0.9364682341170585, 0.316860492889684, 0.966983491745873 ], "category_id": 1, "smiles": "*[H]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.6168 -3.2520 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9108 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nA 2\nPbBr\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.3515011898615465, 0.9364682341170585, 0.44370657444841594, 0.966983491745873 ], "category_id": 2, "text": [ "NaHCO3" ] } ], "conditions": [], "products": [ { "category": "[Txt]", "bbox": [ 0.5272517847923198, 0.9364682341170585, 0.586854160464495, 0.967983991995998 ], "category_id": 2, "text": [ "Pd(o)" ] }, { "category": "[Txt]", "bbox": [ 0.6225137014649418, 0.9369684842421211, 0.6800783890799487, 0.9649824912456229 ], "category_id": 2, "text": [ "NaBr" ] }, { "category": "[Txt]", "bbox": [ 0.7167567741089796, 0.9374687343671836, 0.7656612874810208, 0.967983991995998 ], "category_id": 2, "text": [ "HzO" ] }, { "category": "[Txt]", "bbox": [ 0.8064150486243885, 0.9354677338669335, 0.8675456903394401, 0.966983491745873 ], "category_id": 2, "text": [ "COz" ] } ] } ], "Mukaiyama Michael addition.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.013506753376688344, 0.2748596520482463, 0.20260130065032517, 0.7982880329053416 ], "category_id": 1, "smiles": "*/C=C/C(C)=O", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 16.2958 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6292 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9627 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2961 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6296 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6292 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 6 2 0\n 3 4 2 0\n 4 5 1 0\nA 5\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.2961480740370185, 0.20554721805347118, 0.551775887943972, 0.7982880329053416 ], "category_id": 1, "smiles": "[1*]/C=C(\\[2*])O[Si](C)(C)C", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2804 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9449 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6094 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9449 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2804 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6094 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3801 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6094 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6159 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\nM ISO 2 7 1 9 2\nA 5\nR\nA 7\nR1\nA 9\nR2\nM END\n" } ] } ], "Mukaiyama aldol reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.021010505252626314, 0.18362079590519897, 0.23461730865432717, 0.4663001790750448 ], "category_id": 1, "smiles": "**O=*", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 R 0 0 0 0 0 0 0 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0.4767383691845923, 0.6330085332521334 ], "category_id": 2, "text": [ "X-SiMe3" ] }, { "category": "[Mol]", "bbox": [ 0.4897448724362181, 0.22710993177748295, 0.6943471735867934, 0.8238775184693796 ], "category_id": 1, "smiles": "*C(O[Si](C)(C)C)C([1*])C([2*])=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 7.0583 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0583 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5748 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5417 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5417 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0252 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6394 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0252 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 2 0\nM ISO 2 5 1 7 2\nA 2\nMe3SiO\nA 3\nR\nA 5\nR1\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4897448724362181, 0.22710993177748295, 0.6943471735867934, 0.8238775184693796 ], "category_id": 1, "smiles": "*C(O[Si](C)(C)C)C([1*])C([2*])=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 7.0583 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0583 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5748 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5417 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5417 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0252 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6394 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0252 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 2 0\nM ISO 2 5 1 7 2\nA 2\nMe3SiO\nA 3\nR\nA 5\nR1\nA 7\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.799399699849925, 0.15221197555299387, 0.9639819909954978, 0.7417313729328433 ], "category_id": 1, "smiles": "*C(O)C(*)C([2*])=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 6.3469 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3469 -7.7402 0.0000 R 0 0 0 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"bbox": [ 0.46973486743371684, 0.8257516608771676, 0.6593296648324162, 0.9644156190244655 ], "category_id": 2, "text": [ "X=F, Cl; Br" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6418209104552276, 0.4596164904882348, 0.7718859429714857, 0.7260382527712455 ], "category_id": 1, "smiles": "[1*]C(=O)O[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 5.9560 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3824 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1722 -6.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5076 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9560 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 2 0\n 3 4 1 0\nM ISO 2 2 1 4 2\nA 2\nR1\nA 4\nR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.8124062031015508, 0.4159918744418938, 0.9159579789894947, 0.8101714408606171 ], "category_id": 1, "smiles": "[3*]N1C=CCC=C1=O", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 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"category_id": 2, "text": [ "reversible" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4627313656828414, 0.4257759073442538, 0.535767883941971, 0.6566739048194458 ], "category_id": 1, "smiles": "[H]C1C=CCC=C1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 2.9863 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5133 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5133 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9863 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9863 -7.8976 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5526 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5526 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 7 1 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.42471235617808906, 0.7167073841629956, 0.5287643821910956, 0.8875719022946376 ], "category_id": 1, "smiles": "Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 0.6999 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1741 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1741 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4112 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6999 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.42471235617808906, 0.7167073841629956, 0.5287643821910956, 0.8875719022946376 ], "category_id": 1, "smiles": "Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 0.6999 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1741 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1741 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4112 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6999 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.15307653826913456, 0.6077235293547051, 0.2586293146573287, 0.8035250312136677 ], "category_id": 1, "smiles": "C#C/C=C\\C=C=C", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 10.0000 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6929 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3071 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9921 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2992 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 3 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4612306153076538, 0.4257759073442538, 0.535767883941971, 0.6566739048194458 ], "category_id": 1, "smiles": "[H]C1C=CCC=C1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 3.0330 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5213 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5213 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0330 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0330 -7.8976 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6394 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6394 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 7 1 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.42471235617808906, 0.7167073841629956, 0.5287643821910956, 0.8875719022946376 ], "category_id": 1, "smiles": "Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 0.6999 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1741 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1741 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4112 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9370 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6999 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6078039019509754, 0.640049249001232, 0.6823411705852926, 0.885724718314836 ], "category_id": 1, "smiles": "Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 2.8238 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8238 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4853 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4853 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8238 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6034 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6034 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 7 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6078039019509754, 0.640049249001232, 0.6823411705852926, 0.885724718314836 ], "category_id": 1, "smiles": "Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 2.8238 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8238 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4853 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4853 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8238 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6034 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6034 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 7 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8074037018509255, 0.6326605130820258, 0.9089544772386193, 0.7850531914156523 ], "category_id": 1, "smiles": "Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 11.5160 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9051 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3917 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8783 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8783 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3917 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9051 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 7 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\nM END\n" } ] } ], "Nazarov cyclization.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.02301150575287644, 0.053057270045511, 0.208104052026013, 0.5269551593156434 ], "category_id": 1, "smiles": "C/C=C/C(=O)C1=CCCCC1.[H]", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 9.0299 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2535 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2535 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5512 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8488 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0724 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3701 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3701 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0724 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8488 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5512 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2913 -0.7323 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 11 2 0\n 5 6 1 0\n 5 10 2 0\n 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0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 3\n 3 4 1 0\n 4 5 1 0\n 4 11 2 3\n 5 6 1 0\n 5 10 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 11 12 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.416208104052026, 0.09164437553315537, 0.6018009004502252, 0.48354466564204346 ], "category_id": 1, "smiles": "[H]O=C(C=CC)C1=CCCCC1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 6.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 3\n 3 4 1 0\n 4 5 1 0\n 4 11 2 3\n 5 6 1 0\n 5 10 2 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 11 12 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7323661830915458, 0.07355666983582207, 0.9169584792396198, 0.4738978892701324 ], "category_id": 1, "smiles": "[H]C([H])(C)C/C(O)=C1/CCCCC1C", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 6.9116 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5494 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4497 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4374 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4374 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4497 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5494 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5617 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5617 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5739 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5739 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4366 -8.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7113 -2.8583 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6737 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 11 12 1 0\n 11 13 1 0\n 11 14 1 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.21860930465232617, 0.5848358175471099, 0.4047023511755878, 0.9285022257964425 ], "category_id": 1, "smiles": "CC1=CC(O)=C2CCCCC12", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 12.5146 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1553 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3341 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8722 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6155 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6155 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8722 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3341 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6934 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6934 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1553 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 1 0\n 3 8 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.21860930465232617, 0.5848358175471099, 0.4047023511755878, 0.9285022257964425 ], "category_id": 1, "smiles": "CC1=CC(O)=C2CCCCC12", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 12.5146 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1553 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3341 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8722 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6155 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6155 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8722 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3341 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6934 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6934 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1553 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 1 0\n 3 8 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.43121560780390195, 0.6861269694521764, 0.6288144072036018, 0.7681245686134206 ], "category_id": 2, "text": [ "tautomerization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6633316658329165, 0.5800124293611544, 0.8459229614807404, 0.9212671435175092 ], "category_id": 1, "smiles": "CC1=CC(=O)C2CCCCC12", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 12.8704 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2355 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2355 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6006 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6006 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1684 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8376 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5067 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5067 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8376 -8.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1684 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 11 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 6 11 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nM END\n" } ] } ], "Neber rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.07003501750875438, 0.2690527872631968, 0.14057028514257128, 0.390822367705592 ], "category_id": 1, "smiles": "CCO", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 3.3386 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nEtO\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.19609804902451225, 0.08349914087478522, 0.36068034017008505, 0.4383704895926224 ], "category_id": 1, "smiles": "[1*]C([H])C([2*])=NOS(=O)(=O)c1ccc(C)cc1", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 3.2243 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0182 -3.9606 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2243 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4304 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6364 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4304 -1.4409 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5516 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\nM ISO 2 3 1 5 2\nA 3\nR1\nA 5\nR2\nA 7\nOTs\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3791895947973987, 0.18091480522870132, 0.5587793896948474, 0.27253191813297956 ], "category_id": 2, "text": [ "deprotonation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5852926463231616, 0.10205450551362638, 0.7298649324662331, 0.45576614394153603 ], "category_id": 1, "smiles": "[1*]CC([2*])=NOS(=O)(=O)c1ccc(C)cc1", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 1.9414 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9414 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1814 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3467 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1814 -1.4409 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3467 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\nM ISO 2 2 1 4 2\nA 2\nR1\nA 4\nR2\nA 6\nOTs\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5852926463231616, 0.10205450551362638, 0.7298649324662331, 0.45576614394153603 ], "category_id": 1, "smiles": "[1*]CC([2*])=NOS(=O)(=O)c1ccc(C)cc1", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 1.9414 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9414 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1814 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3467 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1814 -1.4409 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3467 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\nM ISO 2 2 1 4 2\nA 2\nR1\nA 4\nR2\nA 6\nOTs\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7628814407203601, 0.16931770232942558, 0.9024512256128064, 0.2655736563934141 ], "category_id": 2, "text": [ "cyclization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.04752376188094047, 0.5879731169932793, 0.13006503251625812, 0.7167009591752398 ], "category_id": 1, "smiles": "*", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 3.7466 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nTsO\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.18509254627313657, 0.5218696304674076, 0.24362181090545273, 0.6216047154011789 ], "category_id": 1, "smiles": "[Pd]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 3.2111 -5.3780 0.0000 Pd 0 0 0 0 0 15 0 0 0 0 0 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.16908454227113556, 0.6134867433716858, 0.32266133066533265, 0.8280331470082868 ], "category_id": 1, "smiles": "[1*]C1N=C1[2*]", "molfile": "\n RDKit 2D\n\n 5 5 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5276 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4229 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1867 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.7143 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 3 4 2 0\n 4 5 1 0\nM ISO 2 1 1 5 2\nA 1\nR1\nA 5\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04752376188094047, 0.5879731169932793, 0.13006503251625812, 0.7167009591752398 ], "category_id": 1, "smiles": "*", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 3.7466 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nTsO\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.16908454227113556, 0.6134867433716858, 0.32266133066533265, 0.8280331470082868 ], "category_id": 1, "smiles": "[1*]C1N=C1[2*]", "molfile": "\n RDKit 2D\n\n 5 5 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -9.0000 0.0000 R 0 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0.3806903451725863, 0.5715715000357321 ], "category_id": 1, "smiles": "**[1*]", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 7.4373 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4373 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 21.5490 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\nM ISO 1 1 1\nA 1\nR1\nA 2\nPd(II)\nA 3\nLn\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.06453226613306653, 0.7348776429030842, 0.13956978489244623, 0.786838688360878 ], "category_id": 2, "text": [ "ZnXz" ] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.17508754377188596, 0.4664122413711494, 0.3806903451725863, 0.5715715000357321 ], "category_id": 1, "smiles": "**[1*]", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 7.4373 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4373 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 21.5490 -5.8504 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\nM ISO 1 1 1\nA 1\nR1\nA 2\nPd(II)\nA 3\nLn\nM END\n" } ], "conditions": [ { 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4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 14 1 0\n 7 8 1 0\n 7 9 1 0\n 7 15 1 0\n 9 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\n 12 14 2 0\n 15 16 1 0\nM ISO 1 4 2\nA 4\nR2\nA 13\nRi\nA 16\nCO2R3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6298149074537268, 0.5455116301606301, 0.9189594797398699, 0.8841652501643492 ], "category_id": 1, "smiles": "*OC(=O)c1c(C)n([2*])c2cc([Rf])c(O)cc12", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 13.2820 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0487 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7558 -5.9291 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4610 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6401 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7594 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8788 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9982 -6.3228 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 3.8788 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9982 -1.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7594 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6401 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7558 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3435 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 13 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 5 12 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 9 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 1 0\nM ISO 1 4 2\nA 4\nR2\nA 14\nCO2Ra\nM END\n" } ] } ], "Newman\u2212Kwart reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.048024012006003, 0.2122717307206658, 0.112056028014007, 0.44598505040301506 ], "category_id": 1, "smiles": "Oc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 2.9291 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3468 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3468 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9291 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9291 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5579 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5579 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.14807403701850924, 0.15545151997220477, 0.27463731865932967, 0.3184075960809987 ], "category_id": 1, "smiles": "*C(=S)Cl", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 6.3609 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8659 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8174 -6.7165 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3609 -0.7323 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nA 2\nNMe2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3401700850425213, 0.15866775831645727, 0.4752376188094047, 0.4920844666706344 ], "category_id": 1, "smiles": "*C(=S)Oc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 3.7822 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5013 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4126 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4126 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 0.1339 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 2 0\n 3 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\nA 2\nNMe2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3401700850425213, 0.15866775831645727, 0.4752376188094047, 0.4920844666706344 ], "category_id": 1, "smiles": "*C(=S)Oc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 3.7822 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5013 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4126 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4126 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 0.1339 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 2 0\n 3 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\nA 2\nNMe2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5092546273136568, 0.2894614509827261, 0.5302651325662832, 0.33877710559459795 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5782891445722862, 0.15973983776454145, 0.7138569284642321, 0.4931565461187185 ], "category_id": 1, "smiles": "*C(=O)Sc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 3.7822 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4325 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -2.7795 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4126 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4126 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 2 0\n 3 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\nA 2\nNMe2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5782891445722862, 0.15973983776454145, 0.7138569284642321, 0.4931565461187185 ], "category_id": 1, "smiles": "*C(=O)Sc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 3.7822 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4325 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -2.7795 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0630 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4126 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4126 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7822 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 2 0\n 3 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\nA 2\nNMe2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7593796898449224, 0.2530107497478643, 0.8659329664832416, 0.32055175497716704 ], "category_id": 2, "text": [ "hydrolysis" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.9069534767383692, 0.18975806231089823, 0.9709854927463731, 0.4288317792336683 ], "category_id": 1, "smiles": "Sc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 2.8288 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1556 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1556 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8288 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8288 -0.1811 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5019 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5019 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.17508754377188596, 0.608941126511809, 0.28564282141070535, 0.9455740732102386 ], "category_id": 1, "smiles": "*C(=S)Oc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 3.6825 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6825 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0087 -2.7795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0087 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6825 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6825 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0087 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3906 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3906 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3564 -2.7795 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 2 0\n 3 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\nA 2\nNMe2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3806903451725863, 0.7140049124240577, 0.5947973986993497, 0.8941142597021984 ], "category_id": 1, "smiles": "CN(C)C1=S[C@@]2(C=C[CH]CC2)O1", "molfile": "\n RDKit 2D\n\n 10 11 0 0 0 0 0 0 0 0999 V2000\n 22.3360 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.1041 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8906 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6710 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8600 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0367 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0796 -5.5354 0.0000 S 0 0 0 0 0 3 0 0 0 0 0 0\n 16.7017 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 22.1347 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 24.7507 -2.2283 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 3 4 1 0\n 3 7 1 0\n 3 8 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 2 0\n 9 10 1 0\n 3 2 1 1\nM RAD 2 7 2 10 2\nA 6\nMe2N\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3806903451725863, 0.7140049124240577, 0.5947973986993497, 0.8941142597021984 ], "category_id": 1, "smiles": "CN(C)C1=S[C@@]2(C=C[CH]CC2)O1", "molfile": "\n RDKit 2D\n\n 10 11 0 0 0 0 0 0 0 0999 V2000\n 22.3360 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.1041 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8906 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6710 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8600 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0367 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0796 -5.5354 0.0000 S 0 0 0 0 0 3 0 0 0 0 0 0\n 16.7017 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 22.1347 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 24.7507 -2.2283 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 3 4 1 0\n 3 7 1 0\n 3 8 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 2 0\n 9 10 1 0\n 3 2 1 1\nM RAD 2 7 2 10 2\nA 6\nMe2N\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7058529264632316, 0.5907157758943781, 0.8429214607303652, 0.928420802040892 ], "category_id": 1, "smiles": "*C(=O)Sc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 3.7609 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4020 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0514 -2.7795 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0514 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7609 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7609 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0514 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4103 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4103 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7609 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 2 0\n 3 4 1 0\n 4 5 2 0\n 4 9 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\nA 2\nNMe2\nM END\n" } ] } ], "Nicholas reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0735367683841921, 0.07091720463406306, 0.25212606303151575, 0.19158229908605098 ], "category_id": 1, "smiles": "O=C([Co])C(=O)C(=O)C(=O)[Co][Co]", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 12.9774 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.4679 -5.5354 0.0000 Co 0 0 0 0 0 2 0 0 0 0 0 0\n 18.4679 -1.0472 0.0000 Co 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\nM RAD 2 2 2 3 2\nA 1\n(CO)4Co\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.1025512756378189, 0.22016087408783758, 0.2541270635317659, 0.3789307352088743 ], "category_id": 1, "smiles": "[1*]C#CC([3*])([4*])O[2*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 5.8268 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0472 -4.1969 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7638 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3858 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2756 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2756 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 17.3228 -4.1969 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\nM ISO 3 2 1 6 4 7 3\nA 2\nR1\nA 5\nOR2\nA 6\nR4\nA 7\nR3\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.27463731865932967, 0.13548361482328466, 0.33166583291645824, 0.19264076482685785 ], "category_id": 2, "text": [ "CO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.35267633816908456, 0.09526191667262202, 0.5492746373186593, 0.35035216020708765 ], "category_id": 1, "smiles": "**1([Co]OOC([Co])(OOC)OOC)C([1*])=C1C([3*])([4*])O[2*]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 6.0505 -2.5433 0.0000 Co 0 0 0 0 0 2 0 0 0 0 0 0\n 6.0505 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6252 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1309 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4964 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0505 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7333 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8136 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6550 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1309 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9723 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 5 6 2 0\n 5 8 1 0\n 6 7 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM RAD 1 1 2\nM ISO 3 7 1 9 4 11 3\nA 2\nCo(COO)3\nA 3\nCo(COO)3\nA 4\n(CoO)3\nA 7\nR1\nA 9\nR4\nA 10\nOR2\nA 11\nR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.35267633816908456, 0.09526191667262202, 0.5492746373186593, 0.35035216020708765 ], "category_id": 1, "smiles": "**1([Co]OOC([Co])(OOC)OOC)C([1*])=C1C([3*])([4*])O[2*]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 6.0505 -2.5433 0.0000 Co 0 0 0 0 0 2 0 0 0 0 0 0\n 6.0505 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6252 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1309 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4964 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0505 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7333 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8136 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6550 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1309 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9723 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 5 6 2 0\n 5 8 1 0\n 6 7 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM RAD 1 1 2\nM ISO 3 7 1 9 4 11 3\nA 2\nCo(COO)3\nA 3\nCo(COO)3\nA 4\n(CoO)3\nA 7\nR1\nA 9\nR4\nA 10\nOR2\nA 11\nR3\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5532766383191596, 0.13865901204570538, 0.6113056528264132, 0.20005002501250624 ], "category_id": 2, "text": [ "CO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6248124062031015, 0.11537276574795334, 0.8219109554777388, 0.3101304620564251 ], "category_id": 1, "smiles": "[1*]C1234*567C189C521C683C7914C([3*])([4*])O[2*]", "molfile": "\n RDKit 2D\n\n 11 20 0 0 0 0 0 0 0 0999 V2000\n -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.1830 -2.0490 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9821 2.7990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4821 0.2010 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0311 2.2500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1651 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1651 2.2500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 1 0\n 1 9 1 0\n 1 10 1 0\n 1 11 1 0\n 3 4 1 0\n 3 8 1 0\n 3 9 1 0\n 3 10 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\n 9 10 1 0\n 9 11 1 0\n 10 11 1 0\nM ISO 3 2 1 5 4 7 3\nA 2\nR1\nA 5\nR4\nA 6\nOR2\nA 7\nR3\nA 11\n(CO)3Co\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6248124062031015, 0.11537276574795334, 0.8219109554777388, 0.3101304620564251 ], "category_id": 1, "smiles": "[1*]C1234*567C189C521C683C7914C([3*])([4*])O[2*]", "molfile": "\n RDKit 2D\n\n 11 20 0 0 0 0 0 0 0 0999 V2000\n -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.1830 -2.0490 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9821 2.7990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4821 0.2010 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0311 2.2500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1651 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1651 2.2500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 1 0\n 1 9 1 0\n 1 10 1 0\n 1 11 1 0\n 3 4 1 0\n 3 8 1 0\n 3 9 1 0\n 3 10 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\n 9 10 1 0\n 9 11 1 0\n 10 11 1 0\nM ISO 3 2 1 5 4 7 3\nA 2\nR1\nA 5\nR4\nA 6\nOR2\nA 7\nR3\nA 11\n(CO)3Co\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8394197098549274, 0.11431430000714643, 0.896448224112056, 0.18734843612282334 ], "category_id": 2, "text": [ "+H\"" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.08204102051025512, 0.4138601046555024, 0.2876438219109555, 0.6054424037415533 ], "category_id": 1, "smiles": "[1*]C12*3C1C32C([3*])([4*])O([2*])[H]", "molfile": "\n RDKit 2D\n\n 11 13 0 0 0 0 0 0 0 0999 V2000\n 0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1651 -0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4821 0.2010 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9821 2.7990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0311 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0311 3.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3301 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 1 0\nM ISO 4 2 1 7 4 8 3 11 2\nA 2\nR1\nA 4\nCo(CO)3Co\nA 7\nR4\nA 8\nR3\nA 11\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.08204102051025512, 0.4138601046555024, 0.2876438219109555, 0.6054424037415533 ], "category_id": 1, "smiles": "[1*]C12*3C1C32C([3*])([4*])O([2*])[H]", "molfile": "\n RDKit 2D\n\n 11 13 0 0 0 0 0 0 0 0999 V2000\n 0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1651 -0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4821 0.2010 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9821 2.7990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0311 2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0311 3.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3301 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 1 0\nM ISO 4 2 1 7 4 8 3 11 2\nA 2\nR1\nA 4\nCo(CO)3Co\nA 7\nR4\nA 8\nR3\nA 11\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.33016508254127064, 0.4498479398429373, 0.3736868434217109, 0.513355884291352 ], "category_id": 2, "text": [ "Sn1" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4177088544272136, 0.42232783058195766, 0.5967983991995998, 0.6170855268904294 ], "category_id": 1, "smiles": "[1*]C1*C1C([3*])([3*])[4*]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 8.3268 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9344 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4108 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4108 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4948 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1070 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0367 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2657 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 4 2 1 6 4 7 3 8 3\nA 2\nR1\nA 3\n(Co(CO)3CoO)3\nA 6\nR4\nA 7\nR3\nA 8\nR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4177088544272136, 0.42232783058195766, 0.5967983991995998, 0.6170855268904294 ], "category_id": 1, "smiles": "[1*]C12*3*1C32C([3*])([4*])[4*]", "molfile": "\n RDKit 2D\n\n 9 11 0 0 0 0 0 0 0 0999 V2000\n 8.3268 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9344 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4108 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4108 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4948 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1070 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0367 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2657 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3268 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 9 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 1 0\n 4 9 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 4 2 1 6 4 7 3 8 4\nA 2\nR1\nA 3\n(Co(CO)3Co\nA 6\nR4\nA 7\nR3\nA 8\nR4\nA 9\nCo(CO)3Co\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6268134067033517, 0.4530233370653581, 0.678839419709855, 0.5080635555873175 ], "category_id": 2, "text": [ "NuH" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7138569284642321, 0.4191524333595369, 0.8994497248624312, 0.6160270611496225 ], "category_id": 1, "smiles": "*C([3*])([4*])C1*C1[1*]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 14.4882 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9134 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1102 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0630 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3386 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1890 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1890 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8819 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 6 7 1 0\n 7 8 1 0\nM ISO 3 2 4 4 3 8 1\nA 2\nR4\nA 3\nNu\nA 4\nR3\nA 6\nCo((CO)3CoO)3\nA 8\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.29314657328664334, 0.8446556611639153, 0.3871935967983992, 0.9113390028347507 ], "category_id": 1, "smiles": "O=C=O", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 12.7559 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0157 -4.6693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 21.9685 -4.6693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 3 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.4352176088044022, 0.7853815796787282, 0.6193096548274137, 0.9811977417280069 ], "category_id": 1, "smiles": "*C1([3*])([4*])C23C4C25([1*])*C4315", "molfile": "\n RDKit 2D\n\n 10 14 0 0 0 0 0 0 0 0999 V2000\n -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5989 -0.0297 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.1946 -2.5607 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3149 -1.1118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6160 -2.7990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 1 6 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 3 7 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM ISO 3 2 1 8 4 10 3\nA 2\nR1\nA 4\nCo((CO)3Co)2\nA 8\nR4\nA 9\nNu\nA 10\nR3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7063531765882941, 0.7991416343092181, 0.8569284642321161, 0.9579114954302549 ], "category_id": 1, "smiles": "*C([3*])([4*])C#C[1*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 5.8268 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8898 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7638 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5433 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4331 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4331 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 17.4803 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 3 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\nM ISO 3 2 1 6 4 7 3\nA 2\nR1\nA 5\nNu\nA 6\nR4\nA 7\nR3\nM END\n" } ] } ], "Nicolaou dehydrogenation.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05202601300650325, 0.1453222747386058, 0.2416208104052026, 0.35351446975419704 ], "category_id": 1, "smiles": "[2*]C([2*])CC(=O)[Rf]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 9.0870 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6608 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2345 -7.1102 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 5.6608 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5133 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0885 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5133 -1.3622 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 4 2 0\n 5 6 1 0\n 5 7 1 0\nM ISO 2 6 2 7 2\nA 6\nR2\nA 7\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.26463231615807903, 0.1607820912001596, 0.46973486743371684, 0.24014248236946914 ], "category_id": 2, "text": [ "tautomerization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.48924462231115556, 0.12677049498474122, 0.6803401700850426, 0.3390853077234135 ], "category_id": 1, "smiles": "[2*]C([2*])/C=C(\\O)[Rf]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 5.4051 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0452 -7.2677 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 5.4051 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9111 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2710 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.6310 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2710 -1.3622 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 2 6 2 7 2\nA 6\nR2\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.48924462231115556, 0.12677049498474122, 0.6803401700850426, 0.3390853077234135 ], "category_id": 1, "smiles": "[2*]C([2*])/C=C(\\O)[Rf]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 5.4051 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0452 -7.2677 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 5.4051 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9111 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2710 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.6310 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2710 -1.3622 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 2 6 2 7 2\nA 6\nR2\nA 7\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.05202601300650325, 0.1453222747386058, 0.2416208104052026, 0.35351446975419704 ], "category_id": 1, "smiles": "[2*]C([2*])CC(=O)[Rf]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 9.0870 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6608 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2345 -7.1102 0.0000 Rf 0 0 0 0 0 1 0 0 0 0 0 0\n 5.6608 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5133 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0885 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5133 -1.3622 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 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7 1 0\n 6 8 2 0\nM RAD 1 3 2\nA 8\nX\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.017008504252126064, 0.5480056590139933, 0.27963981990995496, 0.9604078768944221 ], "category_id": 1, "smiles": "*=C(C)C/C=C(/C)S", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 3.0934 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3431 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3431 -1.1260 0.0000 S 0 0 0 0 0 1 0 0 0 0 0 0\n 7.7334 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9831 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2328 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4826 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2328 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 2 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\nM RAD 1 3 2\nA 8\nX\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.35417708854427216, 0.5759651314126665, 0.5722861430715358, 0.9827754548133605 ], "category_id": 1, "smiles": "*C1(C)SC(C)=CC1[H]", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 3.2773 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3841 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8421 -0.9685 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3637 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6512 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5876 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8421 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6614 -7.8976 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3841 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 8 1 0\n 7 9 1 0\nA 5\nX\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.35417708854427216, 0.5759651314126665, 0.5722861430715358, 0.9827754548133605 ], "category_id": 1, "smiles": "*C1(C)SC(C)=CC1[H]", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 3.2773 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3841 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8421 -0.9685 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3637 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6512 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5876 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8421 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6614 -7.8976 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3841 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\n 7 8 1 0\n 7 9 1 0\nA 5\nX\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6008004002001001, 0.615108392770809, 0.6928464232116058, 0.7353341240851033 ], "category_id": 2, "text": [ "HzX" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7443721860930466, 0.598332709331605, 0.968984492246123, 0.870937565218668 ], "category_id": 1, "smiles": "Cc1ccc(C)s1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 4.7308 -0.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0060 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8270 -1.9134 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1924 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1954 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8270 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0060 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\nM END\n" } ] } ], "Paal\u2013Knorr furan synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.030015007503751877, 0.2623606885409918, 0.21960980490245122, 0.8176908126194244 ], "category_id": 1, "smiles": "*C(=O)C([7*])C([2*])C([3*])=O", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 5.8513 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8513 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3938 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0532 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3938 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1919 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1919 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5324 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8729 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5324 -7.4252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 6 1 0\n 3 4 1 0\n 3 5 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\nM ISO 3 2 7 7 2 9 3\nA 2\nR7\nA 4\nR\nA 7\nR2\nA 9\nR3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.29664832416208103, 0.15085739591107028, 0.4637318659329665, 0.8854673238258474 ], "category_id": 1, "smiles": "*C1(C)[O+]=C([3*])C([2*])C1[1*]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 3.9097 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8150 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2841 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3293 -4.2756 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2676 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8480 -5.6142 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 6.4900 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3667 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8645 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0374 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 9 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\nM CHG 1 6 1\nM ISO 3 2 1 8 3 10 2\nA 2\nR1\nA 4\nR\nA 8\nR3\nA 10\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.29664832416208103, 0.15085739591107028, 0.4637318659329665, 0.8854673238258474 ], "category_id": 1, "smiles": "*C1(C)[O+]=C([3*])C([2*])C1[1*]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 3.9097 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8150 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2841 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3293 -4.2756 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2676 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8480 -5.6142 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 6.4900 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3667 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8645 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0374 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 9 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\nM CHG 1 6 1\nM ISO 3 2 1 8 3 10 2\nA 2\nR1\nA 4\nR\nA 8\nR3\nA 10\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5077538769384692, 0.18365248197869427, 0.6693346673336669, 0.8045727781923749 ], "category_id": 1, "smiles": "*C1=OC([3*])=C([2*])C1([1*])[H]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 1.0037 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 -1.0037 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 9 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\nM ISO 3 2 1 8 3 10 2\nA 2\nR1\nA 5\nR\nA 8\nR3\nA 10\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5077538769384692, 0.18365248197869427, 0.6693346673336669, 0.8045727781923749 ], "category_id": 1, "smiles": "*C1=OC([3*])=C([2*])C1([1*])[H]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 1.0037 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 -1.0037 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 9 1 0\n 4 5 1 0\n 4 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\nM ISO 3 2 1 8 3 10 2\nA 2\nR1\nA 5\nR\nA 8\nR3\nA 10\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7078539269634817, 0.17053444755164468, 0.8679339669834918, 0.6908831464912785 ], "category_id": 1, "smiles": "*c1oc([3*])c([2*])c1[1*]", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 7.7204 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4125 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9707 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2785 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1246 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4806 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3455 -7.6614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5665 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3162 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 2 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 1 0\nM ISO 3 2 2 4 1 9 3\nA 2\nR2\nA 4\nR1\nA 6\nR\nA 9\nR3\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.888944472236118, 0.29734211367979074, 0.9569784892446224, 0.511603342654934 ], "category_id": 1, "smiles": "*", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 2.8759 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nH3O\nM END\n" } ] } ], "Paal\u2013Knorr pyrrole synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.030515257628814407, 0.17015749253937312, 0.2226113056528264, 0.4449388487347122 ], "category_id": 1, "smiles": "*C(=O)CCC(*)=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 6.4654 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8031 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2677 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8031 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0008 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6630 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1984 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6630 -7.7402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 4 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\nA 3\nR\nA 7\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3646823411705853, 0.12876783219195806, 0.567783891945973, 0.4460885615221404 ], "category_id": 1, "smiles": "*C(=O)CCC(*)(O)N[2*]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 5.5390 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3465 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0386 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3465 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8469 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0394 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2319 -2.6220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8469 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8469 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2319 -5.2992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 4 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 10 1 0\n 8 9 1 0\nM ISO 1 9 2\nA 3\nR\nA 7\nR\nA 9\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3646823411705853, 0.12876783219195806, 0.567783891945973, 0.4460885615221404 ], "category_id": 1, "smiles": "*C(=O)CCC(*)(O)N[2*]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 5.5390 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3465 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0386 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3465 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8469 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0394 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2319 -2.6220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8469 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8469 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2319 -5.2992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 4 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 10 1 0\n 8 9 1 0\nM ISO 1 9 2\nA 3\nR\nA 7\nR\nA 9\nR2\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.16258129064532267, 0.08392903348225836, 0.263631815907954, 0.20005002501250624 ], "category_id": 1, "smiles": "[2*]N", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 8.1271 -3.0945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2981 -3.0945 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nM ISO 1 2 2\nA 2\nR2\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.030515257628814407, 0.17015749253937312, 0.2226113056528264, 0.4449388487347122 ], "category_id": 1, "smiles": "*C(=O)CCC(*)=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 6.4654 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8031 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2677 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8031 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0008 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6630 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1984 -3.4882 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6630 -7.7402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 4 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\nA 3\nR\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3646823411705853, 0.12876783219195806, 0.567783891945973, 0.4460885615221404 ], "category_id": 1, "smiles": "*C(=O)CCC(*)(O)N[2*]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 5.5390 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3465 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0386 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3465 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8469 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0394 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2319 -2.6220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8469 -5.2992 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8469 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2319 -5.2992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 1 0\n 2 3 1 0\n 2 4 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 10 1 0\n 8 9 1 0\nM ISO 1 9 2\nA 3\nR\nA 7\nR\nA 9\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6058029014507254, 0.20119973779993447, 0.6728364182091046, 0.2793802073450518 ], "category_id": 2, "text": [ "slow" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7088544272136068, 0.1851037587759397, 0.887943971985993, 0.44723827430956853 ], "category_id": 1, "smiles": "*C1(O)CCC(*)(O)N1[2*]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 6.2163 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2217 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7298 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7352 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7082 -4.7480 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7082 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1948 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9354 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5570 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3245 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM ISO 1 6 2\nA 3\nR\nA 6\nR2\nA 8\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7088544272136068, 0.1851037587759397, 0.887943971985993, 0.44723827430956853 ], "category_id": 1, "smiles": "*C1(O)CCC(*)(O)N1[2*]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 6.2163 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2217 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7298 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7352 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7082 -4.7480 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7082 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1948 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9354 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5570 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3245 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM ISO 1 6 2\nA 3\nR\nA 6\nR2\nA 8\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.04102051025512756, 0.5852038088009521, 0.21660830415207605, 0.9347164961791241 ], "category_id": 1, "smiles": "*C1(O)C([H])C([H])C([1*])=N1[2*]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 2.6401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5241 0.5932 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.3442 2.2172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\nM ISO 2 9 2 11 1\nA 6\nR\nA 9\nR2\nA 11\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04102051025512756, 0.5852038088009521, 0.21660830415207605, 0.9347164961791241 ], "category_id": 1, "smiles": "*C1(O)C([H])C([H])C([1*])=N1[2*]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 2.6401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5241 0.5932 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.3442 2.2172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\nM ISO 2 9 2 11 1\nA 6\nR\nA 9\nR2\nA 11\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3106553276638319, 0.6012997878249469, 0.4917458729364682, 0.9496627624156906 ], "category_id": 1, "smiles": "*C1=C([H])CC(*)([OH-])[N+]1[2*]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.2158 2.5838 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6933 1.9635 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 9 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\nM CHG 2 4 -1 5 1\nM ISO 1 6 2\nA 3\nR\nA 6\nR2\nA 8\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3106553276638319, 0.6012997878249469, 0.4917458729364682, 0.9496627624156906 ], "category_id": 1, "smiles": "*C1=C([H])CC(*)([OH-])[N+]1[2*]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.2158 2.5838 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6933 1.9635 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 9 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\nM CHG 2 4 -1 5 1\nM ISO 1 6 2\nA 3\nR\nA 6\nR2\nA 8\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5552776388194097, 0.5967009366752342, 0.7113556778389195, 0.9439141984785496 ], "category_id": 1, "smiles": "*C1=[N+]([2*])C([7*])=C([H])C1[H]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 4.2245 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9246 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5746 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 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0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 5.3618 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2303 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8551 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4992 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8803 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 9 1 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\nM CHG 1 5 1\nM ISO 2 6 2 8 7\nA 4\nR\nA 6\nR2\nA 8\nR7\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7823911955977989, 0.642689448172362, 0.9429714857428715, 0.9048239637059909 ], "category_id": 1, "smiles": "*c1ccc(*)n1[2*]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 8.3530 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3855 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3963 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5387 -3.6457 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8143 -4.5118 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8143 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 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"category_id": 2, "text": [ "THF", "-78 %CArt" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4687343671835918, 0.1989744872436218, 0.7448724362181091, 0.5337356178089044 ], "category_id": 1, "smiles": "CC.CCN(CC)C(=O)c1cccn1Cc1cc(OC)c(OC)cc1I", "molfile": "\n RDKit 2D\n\n 20 20 0 0 0 0 0 0 0 0999 V2000\n 19.1217 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 22.0769 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8243 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7365 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7365 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8243 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6487 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5609 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5609 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4730 0.0551 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6487 0.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4730 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5591 -3.3307 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5591 -1.0472 0.0000 C 0 0 0 0 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1 0\n 13 17 1 0\n 14 15 2 0\n 15 16 1 0\n 16 17 2 0\n 17 18 1 0\n 18 19 1 0\n 18 20 2 0\nA 3\nH3CO\nA 6\nH3CO\nA 19\nNEt2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7178589294647324, 0.20435217608804404, 0.8544272136068034, 0.28636193096548274 ], "category_id": 2, "text": [ "halogen-metal" ] }, { "category": "[Txt]", "bbox": [ 0.7383691845922962, 0.3213169084542271, 0.8349174587293647, 0.3952601300650325 ], "category_id": 2, "text": [ "exchange" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.8659329664832416, 0.22720735367683842, 0.9289644822411206, 0.4154264632316158 ], "category_id": 1, "smiles": "CC(C)(C)I", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 2.7764 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9154 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9255 -7.0315 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0444 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9766 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.025512756378189096, 0.6426338169084542, 0.25212606303151575, 0.9585730365182592 ], "category_id": 1, "smiles": "CCN(CC)C(=O)c1cccn1Cc1cc(OC)c(OC)cc1I", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 4.2468 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3702 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3702 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2468 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4936 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6170 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7404 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8638 -6.2441 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8638 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8638 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7404 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 17.1389 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 17.1389 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.6556 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.2906 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6170 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5887 -2.5433 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4936 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 18 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 16 1 0\n 7 8 1 0\n 8 9 1 0\n 8 15 1 0\n 9 10 1 0\n 9 13 2 0\n 10 11 1 0\n 10 12 2 0\n 13 14 1 0\n 14 15 2 0\n 16 17 1 0\n 16 18 2 0\nA 1\nH3CO\nA 4\nH3CO\nA 11\nEt2N\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2771385692846423, 0.6937218609304653, 0.38169084542271137, 0.7770760380190096 ], "category_id": 2, "text": [ "cyclization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4112056028014007, 0.5727238619309655, 0.6368184092046023, 0.9276513256628314 ], "category_id": 1, "smiles": "CCN(CC)C1(OO)c2cc(OC)c(OC)cc2Cn2cccc21", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n 3.7818 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6727 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6727 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7818 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5637 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4546 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4546 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4805 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2650 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5611 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5611 0.1339 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 13.3715 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3715 -6.4803 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4805 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.3974 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6130 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2624 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5637 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 18 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 14 1 0\n 7 8 1 0\n 7 18 2 0\n 8 9 1 0\n 8 10 1 0\n 8 12 1 0\n 10 11 1 0\n 12 13 1 0\n 12 17 2 0\n 13 14 1 0\n 13 15 1 0\n 15 16 2 0\n 16 17 1 0\nM RAD 1 11 2\nA 1\nH3CO\nA 4\nH3CO\nA 9\nEt2N\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4112056028014007, 0.5727238619309655, 0.6368184092046023, 0.9276513256628314 ], "category_id": 1, "smiles": "CCN(CC)C1(OO)c2cc(OC)c(OC)cc2Cn2cccc21", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n 3.7818 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6727 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6727 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7818 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5637 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4546 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4546 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4805 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2650 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5611 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5611 0.1339 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 13.3715 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3715 -6.4803 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4805 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.3974 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.6130 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2624 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5637 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 18 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 14 1 0\n 7 8 1 0\n 7 18 2 0\n 8 9 1 0\n 8 10 1 0\n 8 12 1 0\n 10 11 1 0\n 12 13 1 0\n 12 17 2 0\n 13 14 1 0\n 13 15 1 0\n 15 16 2 0\n 16 17 1 0\nM RAD 1 11 2\nA 1\nH3CO\nA 4\nH3CO\nA 9\nEt2N\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7233616808404202, 0.5821348174087044, 0.9479739869934968, 0.8994184592296148 ], "category_id": 1, "smiles": "COc1cc2c(cc1OC)C(=O)c1cccn1C2", "molfile": "\n RDKit 2D\n\n 16 18 0 0 0 0 0 0 0 0999 V2000\n 4.1764 -2.5433 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2646 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2646 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1764 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5020 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4411 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5293 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.7667 -6.2441 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 14.7667 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5293 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5293 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4411 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5020 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.8549 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.3465 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.1532 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 13 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 12 1 0\n 7 8 1 0\n 8 9 1 0\n 8 16 1 0\n 9 10 1 0\n 9 14 2 0\n 10 11 2 0\n 10 12 1 0\n 12 13 2 0\n 14 15 1 0\n 15 16 2 0\nA 1\nH3CO\nA 4\nH3CO\nM END\n" } ] } ], "Passerini reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04852426213106553, 0.20462397263613755, 0.17708854427213608, 0.375545173308676 ], "category_id": 1, "smiles": "[2*]C([3*])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.6501 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4899 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1934 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6501 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 2 3 3\nA 2\nR2\nA 3\nR3\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.21410705352676337, 0.25277078972699346, 0.35767883941970985, 0.3386326135390198 ], "category_id": 1, "smiles": "[4*]C(=O)O", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.3709 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6410 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nM ISO 1 1 4\nA 1\nR4\nA 2\nCO2H\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.45222611305652827, 0.07703490734536943, 0.6648324162081041, 0.3009176068178493 ], "category_id": 1, "smiles": "[2*]C1([3*])=O[H]OC([4*])=O1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 0.9642 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 9 2 0\n 4 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 1 0\nM ISO 3 2 3 3 2 6 4\nA 2\nR3\nA 3\nR2\nA 6\nR4\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5312656328164082, 0.3001151598663351, 0.6003001500750376, 0.5312198819024433 ], "category_id": 1, "smiles": "[7*]N=[Os]", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 1.2094 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2094 -4.0394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2094 -0.6535 0.0000 Os 0 0 0 0 0 2 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\nM ISO 1 1 7\nA 1\nR7\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45222611305652827, 0.07703490734536943, 0.6648324162081041, 0.3009176068178493 ], "category_id": 1, "smiles": "[2*]C1([3*])=O[H]OC([4*])=O1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 0.9642 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 9 2 0\n 4 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 1 0\nM ISO 3 2 3 3 2 6 4\nA 2\nR3\nA 3\nR2\nA 6\nR4\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7348674337168585, 0.1187621488241112, 0.9554777388694348, 0.5055415794539869 ], "category_id": 1, "smiles": "[1*]/N=C(\\OC([4*])=O)C([2*])([3*])O[H]", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 6.3517 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8675 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8675 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4134 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5472 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4134 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6089 -4.5906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7428 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0105 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6089 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3517 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2690 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\n 11 12 1 0\nM ISO 4 2 2 3 3 9 4 12 1\nA 2\nR2\nA 3\nR3\nA 9\nR4\nA 12\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7348674337168585, 0.1187621488241112, 0.9554777388694348, 0.5055415794539869 ], "category_id": 1, "smiles": "[1*]/N=C(\\OC([4*])=O)C([2*])([3*])O[H]", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 6.3517 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8675 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8675 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4134 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5472 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4134 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6089 -4.5906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7428 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0105 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6089 -1.3622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3517 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2690 -8.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\n 11 12 1 0\nM ISO 4 2 2 3 3 9 4 12 1\nA 2\nR2\nA 3\nR3\nA 9\nR4\nA 12\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.11105552776388194, 0.6764627801265253, 0.18259129564782392, 0.7430658771022093 ], "category_id": 2, "text": [ "acyl" ] }, { "category": "[Txt]", "bbox": [ 0.0865432716358179, 0.7799784368718654, 0.20710355177588793, 0.8441741929930067 ], "category_id": 2, "text": [ "transfer" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.2846423211605803, 0.566527547769071, 0.49674837418709356, 0.9500971905928896 ], "category_id": 1, "smiles": "[1*]N1=C23=N([1*])=C=14([O-])([O-]2)C([4*])(O[H])OC34([2*])[3*]", "molfile": "\n RDKit 2D\n\n 16 19 0 0 0 0 0 0 0 0999 V2000\n -0.0000 -1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3908 -1.6226 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3882 -2.5095 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0607 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 2.1213 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0607 2.1213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5095 1.7331 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5607 0.0000 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n -1.4213 -1.0607 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6213 -1.0607 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0607 -2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1213 -1.0607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0000 -1.0607 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4888 -0.8778 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 9 1 0\n 1 13 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 9 1 0\n 7 8 1 0\n 9 10 1 0\n 9 11 2 0\n 9 14 1 0\n 9 15 2 0\n 11 12 1 0\n 11 13 2 0\n 13 14 1 0\n 13 15 2 0\n 15 16 1 0\nM CHG 2 10 -1 14 -1\nM ISO 5 2 2 3 3 6 4 12 1 16 1\nA 2\nR2\nA 3\nR3\nA 6\nR4\nA 12\nR1\nA 16\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2846423211605803, 0.566527547769071, 0.49674837418709356, 0.9500971905928896 ], "category_id": 1, "smiles": 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5 7 1 0\n 5 9 1 0\n 7 8 1 0\n 9 10 1 0\n 9 11 2 0\n 9 14 1 0\n 9 15 2 0\n 11 12 1 0\n 11 13 2 0\n 13 14 1 0\n 13 15 2 0\n 15 16 1 0\nM CHG 2 10 -1 14 -1\nM ISO 5 2 2 3 3 6 4 12 1 16 1\nA 2\nR2\nA 3\nR3\nA 6\nR4\nA 12\nR1\nA 16\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6538269134567284, 0.6379453264538406, 0.9419709854927464, 0.8698524954414633 ], "category_id": 1, "smiles": "[1*]NC(=O)C([2*])([2*])OC([4*])=O", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 10.1349 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5382 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5757 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6296 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1243 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.7750 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1243 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4842 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8336 -3.1732 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8711 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4842 -7.6614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 1 0\n 8 11 2 0\n 9 10 1 0\nM ISO 4 2 2 3 2 6 4 10 1\nA 2\nR2\nA 3\nR2\nA 6\nR4\nA 10\nR1\nM END\n" } ] } ], "Patern\u00f3\u2013B\u00fcchi reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.13956978489244623, 0.08393707343182079, 0.25962981490745374, 0.2732618057280388 ], "category_id": 1, "smiles": "*C(*)=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.3498 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9471 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6603 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3498 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nA 2\nR\nA 3\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.3371685842921461, 0.08953287832727552, 0.4332166083041521, 0.2825881472204633 ], "category_id": 1, "smiles": "CC=C(C)C", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 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0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -2.2500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 6 2 0\n 3 4 1 0\n 3 5 2 0\n 3 6 2 0\n 5 6 1 0\n 6 7 1 0\nA 5\nCo(CO)3\nA 6\nCo(CO)3\nA 7\nOC\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.535767883941971, 0.12138391249300264, 0.5847923961980991, 0.1602890126510163 ], "category_id": 2, "text": [ "CO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5992996498249125, 0.09181603637291225, 0.7348674337168585, 0.2093094388501135 ], "category_id": 1, "smiles": "[H]C12*3C1C32C", "molfile": "\n RDKit 2D\n\n 6 8 0 0 0 0 0 0 0 0999 V2000\n 0.7037 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9409 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4301 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6004 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7707 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9409 -0.3386 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 3 4 1 0\n 3 5 1 0\n 4 5 1 0\n 5 6 1 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"molfile": "\n RDKit 2D\n\n 6 8 0 0 0 0 0 0 0 0999 V2000\n 0.7037 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9409 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4301 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6004 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7707 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9409 -0.3386 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 3 4 1 0\n 3 5 1 0\n 4 5 1 0\n 5 6 1 0\nA 3\nCo(CO)3\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7633816908454227, 0.08170071033182869, 0.848424212106053, 0.2295400909322806 ], "category_id": 1, "smiles": "CO[C@]12C=CC1C=CC2", "molfile": "\n RDKit 2D\n\n 9 10 0 0 0 0 0 0 0 0999 V2000\n 8.1391 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4027 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1220 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1049 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6315 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6486 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5430 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2092 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8584 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 1 0\n 3 6 1 0\n 3 9 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 3 2 1 1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.15657828914457228, 0.44118383579187487, 0.2066033016508254, 0.47853273194356805 ], "category_id": 2, "text": [ "CO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.23711855927963982, 0.3781575735358928, 0.4072036018009004, 0.5929137264081282 ], "category_id": 1, "smiles": "[H]C12C3C1(C)*321C=C[C@]2(OC)CC=CC2C1", "molfile": "\n RDKit 2D\n\n 16 20 0 0 0 0 0 0 0 0999 V2000\n 0.3883 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2328 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1743 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8246 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7954 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8340 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9018 -3.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8434 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8632 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2223 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0668 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7755 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8246 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2035 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2328 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2422 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 14 1 0\n 2 16 1 0\n 3 4 1 0\n 3 13 1 0\n 3 14 1 0\n 3 16 1 0\n 4 5 2 0\n 5 6 1 0\n 6 9 1 0\n 6 12 1 0\n 7 8 1 0\n 9 10 1 0\n 9 13 1 0\n 10 11 2 0\n 11 12 1 0\n 14 15 1 0\n 14 16 1 0\n 6 7 1 1\nA 3\nCo((CO))2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.23711855927963982, 0.3781575735358928, 0.4072036018009004, 0.5929137264081282 ], "category_id": 1, "smiles": "[H]C12C3C1(C)*321C=C[C@]2(OC)CC=CC2C1", "molfile": "\n RDKit 2D\n\n 16 20 0 0 0 0 0 0 0 0999 V2000\n 0.3883 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2328 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1743 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8246 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7954 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8340 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9018 -3.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8434 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8632 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2223 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0668 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7755 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8246 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2035 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2328 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2422 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 14 1 0\n 2 16 1 0\n 3 4 1 0\n 3 13 1 0\n 3 14 1 0\n 3 16 1 0\n 4 5 2 0\n 5 6 1 0\n 6 9 1 0\n 6 12 1 0\n 7 8 1 0\n 9 10 1 0\n 9 13 1 0\n 10 11 2 0\n 11 12 1 0\n 14 15 1 0\n 14 16 1 0\n 6 7 1 1\nA 3\nCo((CO))2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4412206103051526, 0.42873420374131055, 0.496248124062031, 0.46997360990880505 ], "category_id": 2, "text": [ "CO" ] }, { "category": "[Txt]", "bbox": [ 0.4227113556778389, 0.48397944596569, 0.5157578789394698, 0.5485619122279927 ], "category_id": 2, "text": [ "insertion", "toward CH" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5472736368184092, 0.4007225316275407, 0.7243621810905453, 0.5898013183954871 ], "category_id": 1, "smiles": "[H]C1C2([H])C3456*178*319%10*43%11C154(C)C7396C28%11%104[H]", "molfile": "\n RDKit 2D\n\n 13 26 0 0 0 0 0 0 0 0999 V2000\n -1.1830 -2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7477 -1.2135 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9807 1.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4480 0.6918 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3706 2.3740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1206 3.6731 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.1211 2.2172 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9097 0.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.6205 2.2621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4090 0.9861 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 11 1 0\n 2 12 1 0\n 2 13 1 0\n 3 4 1 0\n 3 10 1 0\n 3 11 1 0\n 3 12 1 0\n 3 13 1 0\n 4 5 1 0\n 4 6 1 0\n 4 10 1 0\n 4 11 1 0\n 4 13 1 0\n 6 7 1 0\n 6 8 1 0\n 6 12 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 1 0\n 11 12 1 0\n 11 13 1 0\n 12 13 1 0\nA 3\n(CO)3Co\nA 10\n(CO)3Co\nA 13\n(CO)3Co\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5472736368184092, 0.4007225316275407, 0.7243621810905453, 0.5898013183954871 ], "category_id": 1, "smiles": "[H]C1C2([H])C3456*178*319%10*43%11C154(C)C7396C28%11%104[H]", "molfile": "\n RDKit 2D\n\n 13 26 0 0 0 0 0 0 0 0999 V2000\n -1.1830 -2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7477 -1.2135 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9807 1.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4480 0.6918 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3706 2.3740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1206 3.6731 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.1211 2.2172 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9097 0.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.6205 2.2621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4090 0.9861 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 11 1 0\n 2 12 1 0\n 2 13 1 0\n 3 4 1 0\n 3 10 1 0\n 3 11 1 0\n 3 12 1 0\n 3 13 1 0\n 4 5 1 0\n 4 6 1 0\n 4 10 1 0\n 4 11 1 0\n 4 13 1 0\n 6 7 1 0\n 6 8 1 0\n 6 12 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 1 0\n 11 12 1 0\n 11 13 1 0\n 12 13 1 0\nA 3\n(CO)3Co\nA 10\n(CO)3Co\nA 13\n(CO)3Co\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7613806903451726, 0.43729332577607355, 0.8119059529764883, 0.47619842593408723 ], "category_id": 2, "text": [ "CO" ] }, { "category": "[Txt]", "bbox": [ 0.7493746873436719, 0.492538568000453, 0.8234117058529264, 0.5306655661553064 ], "category_id": 2, "text": [ "insertion" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.064032016008004, 0.7360844949896185, 0.2591295647823912, 0.9430596278302511 ], "category_id": 1, "smiles": "[H]C12*C1(C)*C(=O)C1C3C=CC[C@@]3(OC)C12", "molfile": "\n RDKit 2D\n\n 17 20 0 0 0 0 0 0 0 0999 V2000\n 2.6587 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8551 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9707 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8202 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8202 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6698 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8661 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9065 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1377 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2185 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9873 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2185 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2533 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8258 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2478 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7505 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2423 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 1 0\n 2 17 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 6 14 1 0\n 7 8 1 0\n 7 13 1 0\n 8 11 1 0\n 8 14 1 0\n 9 10 1 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\n 15 16 1 0\n 15 17 1 0\n 8 9 1 1\nA 3\n(CO)3Co\nA 17\n(CO)3Co\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.064032016008004, 0.7360844949896185, 0.2591295647823912, 0.9430596278302511 ], "category_id": 1, "smiles": "[H]C12*C1(C)*C(=O)C1C3C=CC[C@@]3(OC)C12", "molfile": "\n RDKit 2D\n\n 17 20 0 0 0 0 0 0 0 0999 V2000\n 2.6587 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8551 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9707 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8202 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8202 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6698 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8661 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9065 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1377 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2185 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9873 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2185 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2533 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8258 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2478 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7505 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2423 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 1 0\n 2 17 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 6 14 1 0\n 7 8 1 0\n 7 13 1 0\n 8 11 1 0\n 8 14 1 0\n 9 10 1 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\n 15 16 1 0\n 15 17 1 0\n 8 9 1 1\nA 3\n(CO)3Co\nA 17\n(CO)3Co\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.27463731865932967, 0.7843268191855554, 0.35417708854427216, 0.8232319193435691 ], "category_id": 2, "text": [ "reductive" ] }, { "category": "[Txt]", "bbox": [ 0.2691345672836418, 0.8387939594067746, 0.3601800900450225, 0.8753647535553075 ], "category_id": 2, "text": [ "elimination" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.39619809904952474, 0.746199821030702, 0.5402701350675337, 0.9103793436975197 ], "category_id": 1, "smiles": "[H]C([H])(C)C1C(C(=O)C(C)(C)C)C2C=CC[C@]21OC", "molfile": "\n RDKit 2D\n\n 19 20 0 0 0 0 0 0 0 0999 V2000\n 5.7705 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3735 -0.4961 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4196 -3.1732 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5872 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2587 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5793 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9303 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7165 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0371 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6862 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8695 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3048 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8470 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4196 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7480 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5951 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5647 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0304 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1294 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 19 1 0\n 4 5 1 0\n 4 12 1 0\n 5 8 1 0\n 5 11 1 0\n 6 7 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\n 13 18 2 0\n 14 15 1 0\n 14 16 1 0\n 14 17 1 0\n 5 6 1 1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.39619809904952474, 0.746199821030702, 0.5402701350675337, 0.9103793436975197 ], "category_id": 1, "smiles": "[H]C([H])(C)C1C(C(=O)C(C)(C)C)C2C=CC[C@]21OC", "molfile": "\n RDKit 2D\n\n 19 20 0 0 0 0 0 0 0 0999 V2000\n 5.7705 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3735 -0.4961 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4196 -3.1732 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5872 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2587 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5793 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9303 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7165 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0371 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6862 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8695 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3048 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8470 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4196 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7480 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5951 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5647 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0304 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1294 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 19 1 0\n 4 5 1 0\n 4 12 1 0\n 5 8 1 0\n 5 11 1 0\n 6 7 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 13 14 1 0\n 13 18 2 0\n 14 15 1 0\n 14 16 1 0\n 14 17 1 0\n 5 6 1 1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5802901450725363, 0.7757676971507924, 0.7478739369684843, 0.820119511330928 ], "category_id": 2, "text": [ "reductive elimination" ] }, { "category": "[Txt]", "bbox": [ 0.6133066533266633, 0.8403501634130951, 0.7218609304652326, 0.8862581815995512 ], "category_id": 2, "text": [ "Coz(CO)6" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7658829414707353, 0.7446436170243815, 0.9079539769884942, 0.8987078136501155 ], "category_id": 1, "smiles": "CO[C@@]12CC=CC1C1C(=O)C(C)=CC12", "molfile": "\n RDKit 2D\n\n 14 16 0 0 0 0 0 0 0 0999 V2000\n 0.5624 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1496 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5996 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5748 -7.8189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2992 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1114 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0236 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6108 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.2733 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5737 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9111 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.6108 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6490 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7368 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 14 2 3\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 13 1 0\n 6 7 1 0\n 6 10 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 13 1 0\n 11 12 1 0\n 13 14 1 0\n 10 11 1 1\nM END\n" } ] } ], "Payne rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04302151075537769, 0.38923760522795336, 0.1890945472736368, 0.8297700886642417 ], "category_id": 1, "smiles": "*C1O[C@@H]1CC[H]", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 3.6476 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7445 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4537 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4537 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1013 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.7488 -6.4803 0.0000 C 0 0 0 0 0 2 0 0 0 0 0 0\n 18.3964 -4.3543 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 4 3 1 1\nM RAD 1 6 3\nA 2\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.21010505252626313, 0.30173457769608786, 0.2606303151575788, 0.5551916229608017 ], "category_id": 1, "smiles": "O", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 5.8345 -5.8504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3611805902951476, 0.35604680168138375, 0.4842421210605303, 0.850891509102968 ], "category_id": 1, "smiles": "*C[CH]COO", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 3.1890 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4173 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4961 -5.5354 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 9.8031 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1102 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 0\nM RAD 1 3 2\nA 2\nR\nA 5\nO2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3611805902951476, 0.35604680168138375, 0.4842421210605303, 0.850891509102968 ], "category_id": 1, "smiles": "*C[CH]COO", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 3.1890 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4173 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4961 -5.5354 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 9.8031 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1102 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 0\nM RAD 1 3 2\nA 2\nR\nA 5\nO2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.21010505252626313, 0.30173457769608786, 0.2606303151575788, 0.5551916229608017 ], "category_id": 1, "smiles": "O", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 5.8345 -5.8504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3611805902951476, 0.35604680168138375, 0.4842421210605303, 0.850891509102968 ], "category_id": 1, "smiles": "*C[CH]COO", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 3.1890 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4173 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4961 -5.5354 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 9.8031 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1102 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 0\nM RAD 1 3 2\nA 2\nR\nA 5\nO2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5157578789394698, 0.374150876343149, 0.5637818909454727, 0.5672610060686453 ], "category_id": 2, "text": [ "SN2" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5977988994497249, 0.19914482127941802, 0.7038519259629815, 0.850891509102968 ], "category_id": 1, "smiles": "*[C@@H](O)[C@@H]1CO1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 8.5737 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5737 -7.7402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1020 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6303 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1586 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6303 -2.1496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 0\n 3 2 1 6\n 4 6 1 1\nA 5\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5977988994497249, 0.19914482127941802, 0.7038519259629815, 0.850891509102968 ], "category_id": 1, "smiles": "*[C@@H](O)[C@@H]1CO1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 8.5737 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5737 -7.7402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1020 -6.2441 0.0000 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"smiles": "*[C@@H](O)[C@@H]1CO1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 8.5737 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5737 -7.7402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1020 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6303 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1586 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6303 -2.1496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 0\n 3 2 1 6\n 4 6 1 1\nA 5\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7393696848424212, 0.3138039608039314, 0.7893946973486743, 0.5340702025220756 ], "category_id": 2, "text": [] }, { "category": "[Txt]", "bbox": [ 0.7303651825912957, 0.6185558842769802, 0.8074037018509255, 0.7784752104559067 ], "category_id": 2, "text": [ "workup" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.8359179589794897, 0.30173457769608786, 0.9384692346173087, 0.8358047802181634 ], "category_id": 1, "smiles": "*[C@@H](O)[C@@H]1CO1", "molfile": "\n RDKit 2D\n\n 6 6 0 0 0 0 0 0 0 0999 V2000\n 9.9557 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9557 -7.4252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0595 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1633 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3576 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1633 -0.4961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 1 0\n 3 2 1 6\n 4 6 1 1\nA 5\nR\nM END\n" } ] } ], "Pechmann coumarin synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04502251125562781, 0.17715013014066427, 0.14757378689344672, 0.4896832865676899 ], "category_id": 1, "smiles": "[H]Oc1ccccc1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 0.5943 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5943 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9713 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3484 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6512 -2.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6512 -0.2598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 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C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4510 -3.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1519 -4.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -4.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -5.7990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 1 0\n 1 11 1 0\n 3 4 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 2 3\n 14 15 1 0\nA 2\nEtO\nA 13\nR\nA 15\nAlCl3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.542271135567784, 0.17426964021967786, 0.7503751875937968, 0.5141674508960743 ], "category_id": 1, "smiles": "*C(=O)C([H])C(=O)Oc1ccccc1.[H]", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 0.5560 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5560 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7799 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0038 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2277 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4516 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4516 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2277 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6755 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6755 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7604 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6755 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0038 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7799 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2893 -2.7795 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 12 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 2 0\n 13 14 2 0\nA 10\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.542271135567784, 0.17426964021967786, 0.7503751875937968, 0.5141674508960743 ], "category_id": 1, "smiles": "*C(=O)C([H])C(=O)Oc1ccccc1.[H]", "molfile": "\n RDKit 2D\n\n 15 14 0 0 0 0 0 0 0 0999 V2000\n 0.5560 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5560 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7799 -0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0038 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2277 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4516 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4516 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2277 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6755 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6755 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7604 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6755 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0038 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7799 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2893 -2.7795 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 12 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 2 0\n 13 14 2 0\nA 10\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.799399699849925, 0.17426964021967786, 0.9499749874937469, 0.5444125950664317 ], "category_id": 1, "smiles": "*/C(O)=C/C(=O)Oc1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.5549 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5549 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5897 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6244 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5667 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6939 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6939 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6592 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6244 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6592 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7287 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6244 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5897 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 8 10 1 0\n 12 13 2 0\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.799399699849925, 0.17426964021967786, 0.9499749874937469, 0.5444125950664317 ], "category_id": 1, "smiles": "*/C(O)=C/C(=O)Oc1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.5549 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5549 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5897 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6244 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5667 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6939 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6939 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6592 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6244 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6592 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7287 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6244 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5897 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 8 10 1 0\n 12 13 2 0\nA 9\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.12306153076538269, 0.6927578259972318, 0.21010505252626313, 0.7791725236268242 ], "category_id": 2, "text": [ "Michael" ] }, { "category": "[Txt]", "bbox": [ 0.12306153076538269, 0.8238201174021136, 0.20910455227613806, 0.9030335902292399 ], "category_id": 2, "text": [ "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.23911955977988994, 0.6135443531701056, 0.41520760380190097, 0.9764860832143932 ], "category_id": 1, "smiles": "*C1(O)C=C(O[H])O=C2C=CC=CC21[H]", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0188 2.2694 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7605 4.0753 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4174 3.1497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 15 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 1 0\n 5 7 1 0\n 5 15 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 10 11 2 0\n 11 12 1 0\n 11 14 1 0\n 12 13 1 0\nA 8\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.23911955977988994, 0.6135443531701056, 0.41520760380190097, 0.9764860832143932 ], "category_id": 1, "smiles": "*C1(O)C=C(O[H])O=C2C=CC=CC21[H]", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0188 2.2694 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7605 4.0753 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4174 3.1497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -6.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 15 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 1 0\n 5 7 1 0\n 5 15 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 10 11 2 0\n 11 12 1 0\n 11 14 1 0\n 12 13 1 0\nA 8\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.49524762381190596, 0.5991419035651735, 0.6708354177088545, 0.9721653483329138 ], "category_id": 1, "smiles": "*C1(O)C=C(O[H])Oc2ccccc21", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 0.5332 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5332 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5594 0.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5855 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6117 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6379 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5574 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5835 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6379 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6117 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4387 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6781 -6.6378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5855 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5594 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 9 2 0\n 7 8 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 1 0\n 13 14 2 0\nA 11\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.49524762381190596, 0.5991419035651735, 0.6708354177088545, 0.9721653483329138 ], "category_id": 1, "smiles": "*C1(O)C=C(O[H])Oc2ccccc21", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 0.5332 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5332 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5594 0.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5855 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6117 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6379 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5574 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5835 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6379 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6117 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4387 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6781 -6.6378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5855 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5594 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 1 0\n 6 9 2 0\n 7 8 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 1 0\n 13 14 2 0\nA 11\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.743871935967984, 0.6409090074194764, 0.8934467233616809, 0.9836873080168594 ], "category_id": 1, "smiles": "*c1cc(=O)oc2ccccc12", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 0.4913 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4913 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6529 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8146 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9762 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2362 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2362 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9762 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9762 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8146 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6529 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2995 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 6 7 1 0\n 6 12 2 0\n 7 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 2 0\nA 9\nR\nM END\n" } ] } ], "Perkin reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03701850925462731, 0.1419796679368948, 0.19159579789894948, 0.24291308116217544 ], "category_id": 1, "smiles": "[H]CC(=O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 0.8096 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5337 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0958 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6580 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.3821 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.9442 -4.9843 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6580 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5337 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 2 0\n 3 4 1 0\n 4 5 1 0\n 4 7 2 0\n 5 6 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.21310655327663833, 0.14668989388740789, 0.28064032016008006, 0.1998481581860557 ], "category_id": 1, "smiles": "CC(O)=O", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 12.5303 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nOAc\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.30965482741370687, 0.12852187950685737, 0.3966983491745873, 0.1695681342184715 ], "category_id": 2, "text": [ "enolate" ] }, { "category": "[Txt]", "bbox": [ 0.30115057528764383, 0.19110059570653137, 0.4047023511755878, 0.22945529273213802 ], "category_id": 2, "text": [ "formation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.42171085542771386, 0.06325160562117588, 0.6018009004502252, 0.2758846628157671 ], "category_id": 1, "smiles": "*C([H])=O.C=C([O-])OC(C)=O", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 0.4465 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1434 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7510 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5372 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5372 -1.0472 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.2341 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1434 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3058 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6089 -5.2205 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2706 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3058 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 8 9 1 0\n 8 10 1 0\n 8 11 2 0\nM CHG 1 5 -1\nA 10\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.42171085542771386, 0.06325160562117588, 0.6018009004502252, 0.2758846628157671 ], "category_id": 1, "smiles": "*C([H])=O.C=C([O-])OC(C)=O", "molfile": "\n RDKit 2D\n\n 11 9 0 0 0 0 0 0 0 0999 V2000\n 0.4465 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1434 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7510 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5372 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5372 -1.0472 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.2341 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1434 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3058 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6089 -5.2205 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2706 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3058 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\n 8 9 1 0\n 8 10 1 0\n 8 11 2 0\nM CHG 1 5 -1\nA 10\nAr\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6498249124562281, 0.13121343719286485, 0.7178589294647324, 0.17293258132598086 ], "category_id": 2, "text": [ "aldol" ] }, { "category": "[Txt]", "bbox": [ 0.6118059029514757, 0.19446504281404076, 0.753376688344172, 0.23349262926114925 ], "category_id": 2, "text": [ "condensation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7583791895947974, 0.07267205752220207, 0.904952476238119, 0.24695041769118664 ], "category_id": 1, "smiles": "*C(O)CC(=O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 5.3440 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7488 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2832 -4.2756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2832 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2347 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1861 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1861 -4.2756 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1.6032 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3317 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3520 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 2 0\n 3 4 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\nM RAD 1 7 2\nA 8\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7583791895947974, 0.07267205752220207, 0.904952476238119, 0.24695041769118664 ], "category_id": 1, "smiles": "*C(O)CC(=O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 5.3440 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7488 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2832 -4.2756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2832 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2347 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1861 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1861 -4.2756 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1.6032 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3317 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3520 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 2 0\n 3 4 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\nM RAD 1 7 2\nA 8\nAr\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.1055527763881941, 0.4151727730666544, 0.25962981490745374, 0.45891058546427604 ], "category_id": 2, "text": [ "intramolecular" ] }, { "category": "[Txt]", "bbox": [ 0.11505752876438219, 0.48044304695233586, 0.25062531265632815, 0.5241808593499575 ], "category_id": 2, "text": [ "acyl transfer" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.29514757378689344, 0.33308026364342613, 0.4447223611805903, 0.5181248545564406 ], "category_id": 1, "smiles": "*C1CC(=O)OC(C)(=O)O1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 2 10 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 2 0\n 8 10 1 0\nA 6\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.29514757378689344, 0.33308026364342613, 0.4447223611805903, 0.5181248545564406 ], "category_id": 1, "smiles": "*C1CC(=O)OC(C)(=O)O1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6491 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 2 10 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 2 0\n 8 10 1 0\nA 6\nAr\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5637818909454727, 0.32837003769291306, 0.7378689344672336, 0.5376386477799949 ], "category_id": 1, "smiles": "*C(OC(C)=O)C([H])C(=O)[O-]", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 0.3514 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1962 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8652 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8652 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0205 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6222 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6222 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3791 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1360 -6.0866 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.3791 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1962 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\nM CHG 1 9 -1\nA 5\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5637818909454727, 0.32837003769291306, 0.7378689344672336, 0.5376386477799949 ], "category_id": 1, "smiles": "*C(OC(C)=O)C([H])C(=O)[O-]", "molfile": "\n RDKit 2D\n\n 11 10 0 0 0 0 0 0 0 0999 V2000\n 0.3514 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1962 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8652 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8652 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0205 -6.0866 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6222 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6222 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3791 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1360 -6.0866 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.3791 -3.0157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1962 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\nM CHG 1 9 -1\nA 5\nAr\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.07253626813406704, 0.6446280657987924, 0.12856428214107055, 0.6876929887749123 ], "category_id": 2, "text": [ "acyl" ] }, { "category": "[Txt]", "bbox": [ 0.054527263631815905, 0.709225450262972, 0.144072036018009, 0.7482530367100805 ], "category_id": 2, "text": [ "transfer" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.1790895447723862, 0.5605168881110586, 0.3856928464232116, 0.7751686135701554 ], "category_id": 1, "smiles": "*C(OC(C)=O)C([H])C(=O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 0.4094 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1496 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8898 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8898 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1496 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6299 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6299 -7.8189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3701 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1102 -5.7717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8504 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5906 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8504 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3701 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1496 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 14 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 13 2 0\n 9 10 1 0\n 10 11 1 0\n 10 12 2 0\nA 5\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1790895447723862, 0.5605168881110586, 0.3856928464232116, 0.7751686135701554 ], "category_id": 1, "smiles": "*C(OC(C)=O)C([H])C(=O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 0.4094 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1496 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8898 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8898 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1496 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6299 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6299 -7.8189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3701 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1102 -5.7717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8504 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5906 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8504 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3701 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1496 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 14 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 13 2 0\n 9 10 1 0\n 10 11 1 0\n 10 12 2 0\nA 5\nAr\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.3026513256628314, 0.7718041664626462, 0.36068034017008505, 0.8263082096042976 ], "category_id": 1, "smiles": "O", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 7.3850 -5.5354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4497248624312156, 0.6291516091042494, 0.4932466233116558, 0.6742352003448747 ], "category_id": 2, "text": [ "E2" ] }, { "category": "[Txt]", "bbox": [ 0.4122061030515258, 0.6937489935684291, 0.5297648824412207, 0.7341223588585413 ], "category_id": 2, "text": [ "elimination" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.551775887943972, 0.6022360322441745, 0.7488744372186094, 0.7031694454694553 ], "category_id": 1, "smiles": "*/C=C/C(=O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 25.3721 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.4528 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9461 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2331 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5201 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0134 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2690 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2331 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 21.4528 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 2 0\n 3 4 1 0\n 4 5 1 0\n 4 8 2 0\n 5 6 2 0\n 6 7 1 0\nA 7\nAr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.551775887943972, 0.6022360322441745, 0.7488744372186094, 0.7031694454694553 ], "category_id": 1, "smiles": "*/C=C/C(=O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 25.3721 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.4528 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.9461 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2331 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5201 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0134 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2690 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2331 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 21.4528 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 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C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9075 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0607 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5318 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.27613806903451726, 0.047184882763962634, 0.3981990995497749, 0.14849360163952946 ], "category_id": 1, "smiles": "*C([3*])([H])[Si][3*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 7.6917 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6809 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6701 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6809 -0.7323 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7240 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nM ISO 1 2 3\nA 2\nR3\nA 3\nSiR3\nA 5\nM\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4747373686843422, 0.047184882763962634, 0.5992996498249125, 0.15196307831335024 ], "category_id": 1, "smiles": "[1*]C([2*])(O)C([3*])([H])[Si][3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 9.4588 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4024 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4024 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7012 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8872 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8872 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5549 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.2164 -3.8031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\nM ISO 3 3 3 5 1 7 2\nA 2\nSiR3\nA 3\nR3\nA 5\nR1\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4747373686843422, 0.047184882763962634, 0.5992996498249125, 0.15196307831335024 ], "category_id": 1, "smiles": "[1*]C([2*])(O)C([3*])([H])[Si][3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 9.4588 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4024 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4024 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7012 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8872 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8872 -0.6535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5549 -3.8031 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.2164 -3.8031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 5 1 0\n 4 6 1 0\n 4 7 1 0\nM ISO 3 3 3 5 1 7 2\nA 2\nSiR3\nA 3\nR3\nA 5\nR1\nA 7\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.615807903951976, 0.05065435943778341, 0.6873436718359179, 0.08881860284981201 ], "category_id": 2, "text": [ "acid or" ] }, { "category": "[Txt]", "bbox": [ 0.6248124062031015, 0.10824767222320839, 0.6768384192096047, 0.14224854362665204 ], "category_id": 2, "text": [ "base" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7058529264632316, 0.043715406090141844, 0.7988994497248624, 0.15196307831335024 ], "category_id": 1, "smiles": "[1*]/C([2*])=C(/[3*])[H]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.7258 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0492 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0492 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4515 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2212 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2212 -1.0472 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 4 6 1 0\nM ISO 3 2 2 3 1 5 3\nA 2\nR2\nA 3\nR1\nA 5\nR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1040520260130065, 0.32474301666962513, 0.18659329664832416, 0.41703109619325796 ], "category_id": 1, "smiles": "[1*]C([2*])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.8718 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9573 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4927 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8718 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 1 3 2\nA 2\nR1\nA 3\nR2\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.11255627813906953, 0.47115493230486216, 0.15057528764382191, 0.5211153964078814 ], "category_id": 2, "text": [] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.31165582791395696, 0.35249883006019145, 0.43771885942971483, 0.48017557165679614 ], "category_id": 1, "smiles": "[1*][C@]([2*])(O)[C@]([3*])(C)[Si][3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 7.8221 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4293 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4293 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7147 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2858 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3217 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2145 -2.0709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9295 -4.9843 0.0000 C 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 4 1 0\n 1 8 1 0\n 4 7 1 0\n 1 3 1 1\n 4 5 1 6\n 4 6 1 1\nM RAD 1 8 2\nM ISO 3 3 3 5 1 6 2\nA 2\nSiR3\nA 3\nR3\nA 5\nR1\nA 6\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.31165582791395696, 0.35249883006019145, 0.43771885942971483, 0.48017557165679614 ], "category_id": 1, "smiles": "[1*][C@]([2*])(O)[C@]([3*])(C)[Si][3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 7.8221 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4293 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4293 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7147 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2858 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3217 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2145 -2.0709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9295 -4.9843 0.0000 C 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 4 1 0\n 1 8 1 0\n 4 7 1 0\n 1 3 1 1\n 4 5 1 6\n 4 6 1 1\nM RAD 1 8 2\nM ISO 3 3 3 5 1 6 2\nA 2\nSiR3\nA 3\nR3\nA 5\nR1\nA 6\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5217608804402201, 0.33306976068679506, 0.6353176588294147, 0.4732366183091546 ], "category_id": 1, "smiles": "[1*][C@]1([2*])O[Si]([3*])[C@]1([3*])[H]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 4.3727 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5171 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0341 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3727 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3176 -2.3858 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3176 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1732 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7454 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 4 1 0\n 1 6 1 0\n 4 5 1 0\n 5 6 1 0\n 6 8 1 0\n 1 2 1 6\n 1 3 1 1\n 6 7 1 6\nM ISO 3 2 1 3 2 8 3\nA 2\nR1\nA 3\nR2\nA 5\nSiR3\nA 8\nR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5217608804402201, 0.33306976068679506, 0.6353176588294147, 0.4732366183091546 ], "category_id": 1, "smiles": "[1*][C@]1([2*])O[Si]([3*])[C@]1([3*])[H]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 4.3727 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5171 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0341 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3727 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3176 -2.3858 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3176 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1732 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7454 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 4 1 0\n 1 6 1 0\n 4 5 1 0\n 5 6 1 0\n 6 8 1 0\n 1 2 1 6\n 1 3 1 1\n 6 7 1 6\nM ISO 3 2 1 3 2 8 3\nA 2\nR1\nA 3\nR2\nA 5\nSiR3\nA 8\nR3\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6803401700850426, 0.3733156901031161, 0.7348674337168585, 0.41147993351514467 ], "category_id": 2, "text": [ "syn-" ] }, { "category": "[Txt]", "bbox": [ 0.6533266633316658, 0.42674563087995615, 0.7588794397198599, 0.46282818828769223 ], "category_id": 2, "text": [ "elimination" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7803901950975488, 0.36013167874259716, 0.8724362181090545, 0.47046103697009795 ], "category_id": 1, "smiles": "[1*]/C([2*])=C(/[3*])[H]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.7340 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0036 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0036 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1948 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0162 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0162 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 4 6 1 0\nM ISO 3 2 2 3 1 5 3\nA 2\nR2\nA 3\nR1\nA 5\nR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5212606303151576, 0.33306976068679506, 0.6353176588294147, 0.4732366183091546 ], "category_id": 1, "smiles": "[1*][C@]1([2*])O[Si]([3*])[C@]1([3*])[H]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 4.3727 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5171 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0341 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3727 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3176 -2.3858 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3176 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1732 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7454 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 4 1 0\n 1 6 1 0\n 4 5 1 0\n 5 6 1 0\n 6 8 1 0\n 1 2 1 6\n 1 3 1 1\n 6 7 1 6\nM ISO 3 2 1 3 2 8 3\nA 2\nR1\nA 3\nR2\nA 5\nSiR3\nA 8\nR3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.31165582791395696, 0.35249883006019145, 0.43771885942971483, 0.48017557165679614 ], "category_id": 1, "smiles": "[1*][C@]([2*])(O)[C@]([3*])(C)[Si][3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 7.8221 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4293 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4293 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7147 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2858 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3217 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2145 -2.0709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9295 -4.9843 0.0000 C 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 4 1 0\n 1 8 1 0\n 4 7 1 0\n 1 3 1 1\n 4 5 1 6\n 4 6 1 1\nM RAD 1 8 2\nM ISO 3 3 3 5 1 6 2\nA 2\nSiR3\nA 3\nR3\nA 5\nR1\nA 6\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.07753876938469234, 0.7570398102276946, 0.20260130065032517, 0.8632057964466106 ], "category_id": 1, "smiles": "[1*]C([2*])([3*])O.[3*][Si]C([3*])[H]", "molfile": "\n RDKit 2D\n\n 9 7 0 0 0 0 0 0 0 0999 V2000\n 5.6299 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9665 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5354 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7106 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7717 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3406 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2598 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0512 -3.8819 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2598 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\nM ISO 4 2 2 3 1 5 3 9 3\nA 2\nR2\nA 3\nR1\nA 5\nR3\nA 7\nSiR3\nA 9\nR3\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.21560780390195097, 0.7688360309186851, 0.2941470735367684, 0.8083880650002421 ], "category_id": 2, "text": [ "rotation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3136568284142071, 0.7605092869015153, 0.43921960980490243, 0.8750020171376011 ], "category_id": 1, "smiles": "[1*][C@]([2*])(O)[C@@]([3*])([H])[Si][3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.2774 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7991 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5982 -6.9528 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5982 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7557 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5548 -6.9528 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5548 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2340 -3.8819 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 4 1 0\n 1 5 1 0\n 5 7 1 0\n 1 2 1 6\n 1 3 1 1\n 5 6 1 1\n 5 8 1 6\nM ISO 3 2 1 3 2 7 3\nA 2\nR1\nA 3\nR2\nA 6\nSiR3\nA 7\nR3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3136568284142071, 0.7605092869015153, 0.43921960980490243, 0.8750020171376011 ], "category_id": 1, "smiles": "[1*][C@]([2*])(O)[C@@]([3*])([H])[Si][3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.2774 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7991 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5982 -6.9528 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5982 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7557 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5548 -6.9528 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5548 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2340 -3.8819 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 4 1 0\n 1 5 1 0\n 5 7 1 0\n 1 2 1 6\n 1 3 1 1\n 5 6 1 1\n 5 8 1 6\nM ISO 3 2 1 3 2 7 3\nA 2\nR1\nA 3\nR2\nA 6\nSiR3\nA 7\nR3\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4577288644322161, 0.7646726589101003, 0.49524762381190596, 0.8139392276783554 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5237618809404703, 0.7313656828414208, 0.6528264132066033, 0.8632057964466106 ], "category_id": 1, "smiles": "[1*][C@]([2*])(O)[C@]([3*])(C)[Si][3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 8.0530 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6636 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6636 -1.9921 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0465 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6507 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0401 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5433 -1.9921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0594 -4.5118 0.0000 C 0 0 0 0 0 1 0 0 0 0 0 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 7 1 0\n 1 2 1 1\n 4 5 1 1\n 4 6 1 6\nM RAD 1 8 2\nM ISO 3 3 3 5 2 6 1\nA 2\nSiR3\nA 3\nR3\nA 5\nR2\nA 6\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5237618809404703, 0.7313656828414208, 0.6528264132066033, 0.8632057964466106 ], "category_id": 1, "smiles": "[1*][C@]([2*])(O)[C@]([3*])(C)[Si][3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 8.0530 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6636 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6636 -1.9921 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0465 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6507 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0401 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5433 -1.9921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0594 -4.5118 0.0000 C 0 0 0 0 0 1 0 0 0 0 0 0\n 1 3 1 0\n 1 4 1 0\n 1 8 1 0\n 4 7 1 0\n 1 2 1 1\n 4 5 1 1\n 4 6 1 6\nM RAD 1 8 2\nM ISO 3 3 3 5 2 6 1\nA 2\nSiR3\nA 3\nR3\nA 5\nR2\nA 6\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7023511755877939, 0.7716116122577418, 0.7863931965982992, 0.812551437008827 ], "category_id": 2, "text": [ "E2 anti-" ] }, { "category": "[Txt]", "bbox": [ 0.6923461730865432, 0.829898820377931, 0.7968984492246123, 0.865287482450903 ], "category_id": 2, "text": [ "elimination" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.8044022011005503, 0.763284868240572, 0.8959479739869936, 0.8729203311333086 ], "category_id": 1, "smiles": "[1*]/C([2*])=C(\\[3*])[H]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 4.1894 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5500 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5500 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4680 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1984 -7.4252 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1984 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\n 4 6 1 0\nM ISO 3 2 2 3 1 6 3\nA 2\nR2\nA 3\nR1\nA 6\nR3\nM END\n" } ] } ], "Pictet\u2013Gams isoquinoline synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05252626313156578, 0.09693584811575116, 0.24912456228114058, 0.44526576387235145 ], "category_id": 1, "smiles": "*C(=O)NCC(O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3784 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3784 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1757 -1.9134 0.0000 C 0 0 0 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0\n 7.4944 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2417 -3.9606 0.0000 P 0 0 0 0 0 5 0 0 0 0 0 0\n 13.2324 -7.2677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.2324 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6394 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 2 0\nM CHG 2 2 1 4 -1\nM RAD 1 4 2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4612306153076538, 0.10013153541627044, 0.7183591795897949, 0.45165713847339 ], "category_id": 1, "smiles": "*/C(=N/CC(O)c1ccccc1)O[P+](=O)=O", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 0.3698 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3698 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2188 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9446 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7936 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7936 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5194 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5194 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3684 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3684 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0942 -4.9843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9433 -6.0079 0.0000 P 0 0 0 0 0 5 0 0 0 0 0 0\n 12.9433 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6690 -4.9843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9446 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2188 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 16 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 15 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 12 13 2 0\n 12 14 2 0\n 15 16 2 0\nM CHG 1 12 1\nM RAD 1 12 2\nA 10\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4612306153076538, 0.10013153541627044, 0.7183591795897949, 0.45165713847339 ], "category_id": 1, "smiles": "*/C(=N/CC(O)c1ccccc1)O[P+](=O)O", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 0.3698 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3698 -2.9370 0.0000 C 0 0 0 0 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0\n 12 13 1 0\n 14 15 1 0\n 16 17 2 0\n 17 18 1 0\n 18 19 2 0\n 19 20 1 0\nM CHG 1 2 1\nA 4\nOPO2\nA 5\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.19409704852426213, 0.4942663024803136, 0.4347173586793397, 0.9267493171505881 ], "category_id": 1, "smiles": "*C1=NCC(O([H])[P-](=O)O[P-](=O)=O)C2=C1C=CC=C2", "molfile": "\n RDKit 2D\n\n 19 20 0 0 0 0 0 0 0 0999 V2000\n -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -3.8971 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 O 0 0 0 0 0 3 0 0 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12 13 1 0\n 12 14 1 0\n 14 15 1 0\n 14 19 2 0\n 15 16 1 0\n 16 17 2 0\n 16 18 2 0\nM CHG 2 14 -1 16 -1\nA 4\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5147573786893447, 0.546462528388795, 0.6828414207103551, 0.9001185896462608 ], "category_id": 1, "smiles": "*C1=NC([H])C(OP(=O)=O)c2ccccc21", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 5.7470 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7470 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9909 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2349 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3991 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3991 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2349 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9909 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7470 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7470 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5030 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5030 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3388 -1.9134 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 12 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 12 13 1 0\nA 2\nOPO2\nA 10\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5147573786893447, 0.546462528388795, 0.6828414207103551, 0.9001185896462608 ], "category_id": 1, "smiles": "*C1=NC([H])C(OP(=O)=O)c2ccccc21", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 5.7470 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7470 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9909 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2349 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3991 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3991 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2349 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9909 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7470 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7470 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5030 -4.9843 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5030 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3388 -1.9134 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 12 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 12 13 1 0\nA 2\nOPO2\nA 10\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7723861930965483, 0.5912021505960648, 0.9089544772386193, 0.854313738338818 ], "category_id": 1, "smiles": "*c1nccc2ccccc12", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 0.5201 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5201 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9473 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2879 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6284 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6284 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9689 -3.7244 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9689 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6284 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2879 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9473 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\nA 6\nR\nM END\n" } ] } ], "Pictet\u2013Spengler tetrahydroisoquinoline synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0830415207603802, 0.04770194337108942, 0.32516258129064535, 0.2663358504885826 ], "category_id": 1, "smiles": "[1*]c1ccc(CCN)cc1[1*]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 6.8093 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0157 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8093 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0157 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6029 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5710 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5710 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.3646 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1582 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1582 -5.6142 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6029 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 11 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 11 2 0\n 8 9 1 0\n 9 10 1 0\nM ISO 2 2 1 4 1\nA 2\nR1\nA 4\nR1\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.3261630815407704, 0.03577645752831706, 0.43121560780390195, 0.28720545071343423 ], "category_id": 1, "smiles": "[2*]C([H])=O[H]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 3\n 4 5 1 0\nM ISO 1 2 2\nA 2\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5027513756878439, 0.030807505093828583, 0.7973986993496749, 0.31602537483346743 ], "category_id": 1, "smiles": "[1*]Oc1cc(CCN([H])C([2*])O)ccc1[1*]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 5.6955 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4173 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6955 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4173 -5.4567 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8110 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9265 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9265 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0420 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1575 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1575 -4.1969 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0420 -5.4567 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4357 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4357 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5512 -4.1969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8110 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 15 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 15 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\n 12 14 1 0\nM ISO 2 4 1 13 2\nA 2\nR1O\nA 4\nR1\nA 13\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5027513756878439, 0.030807505093828583, 0.7973986993496749, 0.31602537483346743 ], "category_id": 1, "smiles": "[1*]Oc1cc(CCN([H])C([2*])O)ccc1[1*]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 5.6955 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4173 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6955 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4173 -5.4567 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8110 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9265 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9265 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0420 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1575 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1575 -4.1969 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0420 -5.4567 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4357 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.4357 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.5512 -4.1969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8110 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 15 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 1 0\n 7 15 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\n 12 14 1 0\nM ISO 2 4 1 13 2\nA 2\nR1O\nA 4\nR1\nA 13\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8139069534767384, 0.08347840089940649, 0.8839419709854928, 0.17590091618089226 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.10355177588794397, 0.3508080418748868, 0.40820410205102553, 0.6340383306407302 ], "category_id": 1, "smiles": "[1*]Oc1cc(CCN([H])C([2*])O)ccc1[1*]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 5.2073 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0236 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2073 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0236 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3911 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5748 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7585 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9423 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9423 -4.1969 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7585 -5.3780 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1260 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1260 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.3097 -4.1969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5748 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3911 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 15 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 14 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 1 0\n 14 15 2 0\nM ISO 2 2 1 12 2\nA 2\nR1\nA 4\nR1O\nA 12\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.10355177588794397, 0.3508080418748868, 0.40820410205102553, 0.6340383306407302 ], "category_id": 1, "smiles": "[1*]Oc1cc(CCN([H])C([2*])O)ccc1[1*]", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 5.2073 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0236 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2073 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0236 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3911 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5748 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7585 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9423 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.9423 -4.1969 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7585 -5.3780 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1260 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.1260 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.3097 -4.1969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5748 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3911 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 1 15 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 14 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 1 0\n 14 15 2 0\nM ISO 2 2 1 12 2\nA 2\nR1\nA 4\nR1O\nA 12\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.43271635817908954, 0.40347893768046467, 0.5147573786893447, 0.4819883861453827 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5532766383191596, 0.3527956228486822, 0.7963981990995498, 0.6340383306407302 ], "category_id": 1, "smiles": "*OC1=CC(CCN([H])=C[2*])=CC=C1O[1*]", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 6.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 3\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 14 2 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 2 0\n 13 14 1 0\nM ISO 1 2 2\nA 2\nR2\nA 10\nRfO\nA 12\nR1O\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5532766383191596, 0.3527956228486822, 0.7963981990995498, 0.6340383306407302 ], "category_id": 1, "smiles": "*OC1=CC(CCN([H])=C[2*])=CC=C1O[1*]", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 6.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 3\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 14 2 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 2 0\n 13 14 1 0\nM ISO 1 2 2\nA 2\nR2\nA 10\nRfO\nA 12\nR1O\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.03751875937968985, 0.6678272071952519, 0.2671335667833917, 0.9550326579086861 ], "category_id": 1, "smiles": "[1*]OC1=C=C2CCNC([2*])C2([H])C=C1O[1*]", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 11.6802 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4195 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4195 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4195 -6.6378 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2844 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1493 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8887 -5.4567 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1493 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8887 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2844 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6802 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6802 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8153 -4.1181 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8153 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 2 10 2 0\n 3 4 1 0\n 3 5 1 0\n 3 11 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\nM ISO 1 12 2\nA 7\nR1O\nA 9\nR1O\nA 12\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03751875937968985, 0.6678272071952519, 0.2671335667833917, 0.9550326579086861 ], "category_id": 1, "smiles": "[1*]OC1=C=C2CCNC([2*])C2([H])C=C1O[1*]", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 11.6802 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4195 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4195 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4195 -6.6378 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2844 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1493 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8887 -5.4567 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1493 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8887 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2844 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6802 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6802 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8153 -4.1181 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8153 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 2 10 2 0\n 3 4 1 0\n 3 5 1 0\n 3 11 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\nM ISO 1 12 2\nA 7\nR1O\nA 9\nR1O\nA 12\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.38519259629814906, 0.6797526930380242, 0.615807903951976, 0.9639767722907654 ], "category_id": 1, "smiles": "[1*]OC1=CC2CCNC([2*])C2([H])C=C1O[1*]", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 11.8386 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5472 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5472 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5472 -6.7165 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3832 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2192 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0551 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2192 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0551 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3832 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8386 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8386 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0026 -4.1181 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0026 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 2 10 1 0\n 3 4 1 0\n 3 5 1 0\n 3 11 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\nM ISO 1 12 2\nA 7\nR1O\nA 9\nR1O\nA 12\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.38519259629814906, 0.6797526930380242, 0.615807903951976, 0.9639767722907654 ], "category_id": 1, "smiles": "[1*]OC1=CC2CCNC([2*])C2([H])C=C1O[1*]", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 11.8386 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5472 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5472 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5472 -6.7165 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3832 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2192 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0551 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2192 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0551 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3832 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8386 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8386 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0026 -4.1181 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0026 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 1 0\n 2 3 1 0\n 2 10 1 0\n 3 4 1 0\n 3 5 1 0\n 3 11 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\nM ISO 1 12 2\nA 7\nR1O\nA 9\nR1O\nA 12\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7198599299649825, 0.6797526930380242, 0.9484742371185593, 0.9659643532645608 ], "category_id": 1, "smiles": "[1*]Oc1cc2c(cc1[1*])C([2*])NCC2", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 11.6197 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3707 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2467 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1227 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9986 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1227 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9986 -5.4567 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2467 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3707 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6197 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6197 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7437 -4.1181 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 13.7437 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 13 1 0\n 2 3 1 0\n 2 9 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\nM ISO 2 7 1 11 2\nA 5\nR1O\nA 7\nR1\nA 11\nR2\nM END\n" } ] } ], "Pinacol rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.17258629314657328, 0.10600309396842598, 0.34367183591795897, 0.3759412053531387 ], "category_id": 1, "smiles": "*C(*)(O)C([2*])([3*])O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.2904 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4449 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4764 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4449 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1043 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0728 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0728 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0413 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 2 6 3 8 2\nA 2\nR\nA 3\nR\nA 6\nR3\nA 8\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.38969484742371185, 0.07518824107062773, 0.4452226113056528, 0.2046106232413804 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4807403701850925, 0.04560598228874141, 0.6518259129564783, 0.3858019582804341 ], "category_id": 1, "smiles": "*C([1*])(O)C([2*])([3*])O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 4.1904 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7286 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1694 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6312 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2114 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6731 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2323 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6731 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 3 2 1 6 3 7 2\nA 2\nR1\nA 3\nR\nA 6\nR3\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4807403701850925, 0.04560598228874141, 0.6518259129564783, 0.3858019582804341 ], "category_id": 1, "smiles": "*C([1*])(O)C([2*])([3*])O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 4.1904 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7286 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1694 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6312 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2114 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6731 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2323 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6731 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 3 2 1 6 3 7 2\nA 2\nR1\nA 3\nR\nA 6\nR3\nA 7\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.17258629314657328, 0.10600309396842598, 0.34367183591795897, 0.3759412053531387 ], "category_id": 1, "smiles": "*C(*)(O)C([2*])([3*])O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.2904 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4449 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4764 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4449 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1043 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0728 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0728 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0413 -3.8819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 2 6 3 8 2\nA 2\nR\nA 3\nR\nA 6\nR3\nA 8\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4807403701850925, 0.04560598228874141, 0.6518259129564783, 0.3858019582804341 ], "category_id": 1, "smiles": "*C([1*])(O)C([2*])([3*])O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 4.1904 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7286 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1694 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6312 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2114 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6731 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2323 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6731 -2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 3 2 1 6 3 7 2\nA 2\nR1\nA 3\nR\nA 6\nR3\nA 7\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7018509254627313, 0.13435275863440035, 0.7978989494747374, 0.246518823182386 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.06753376688344172, 0.6027385226809338, 0.23611805902951477, 0.899793704615709 ], "category_id": 1, "smiles": "*C(*)(O)C([2*])([2*])[3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 4.7325 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4213 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3207 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9715 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2543 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0152 -6.4803 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7761 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7761 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 3 6 3 7 2 8 2\nA 2\nR\nA 3\nR\nA 6\nR3\nA 7\nR2\nA 8\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.06753376688344172, 0.6027385226809338, 0.23611805902951477, 0.899793704615709 ], "category_id": 1, "smiles": "*C(*)(O)C([2*])([2*])[3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 4.7325 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4213 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3207 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9715 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2543 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0152 -6.4803 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7761 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7761 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 3 6 3 7 2 8 2\nA 2\nR\nA 3\nR\nA 6\nR3\nA 7\nR2\nA 8\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2991495747873937, 0.6397163461582918, 0.376688344172086, 0.7358586871994223 ], "category_id": 2, "text": [ "alkyl" ] }, { "category": "[Txt]", "bbox": [ 0.27163581790895447, 0.7900928282995472, 0.4032016008004002, 0.8887003575725015 ], "category_id": 2, "text": [ "migration" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.46673336668334164, 0.5534347580444566, 0.6183091545772886, 0.9404693104408026 ], "category_id": 1, "smiles": "*C(O[H])C([1*])([2*])[3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.5481 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5481 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8281 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8281 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3441 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0640 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3441 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0640 -0.1811 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\nM ISO 3 2 1 3 2 4 3\nA 2\nR1\nA 3\nR2\nA 4\nR3\nA 6\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.46673336668334164, 0.5534347580444566, 0.6183091545772886, 0.9404693104408026 ], "category_id": 1, "smiles": "*C(O[H])C([1*])([2*])[3*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.5481 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5481 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8281 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8281 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3441 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0640 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3441 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0640 -0.1811 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\nM ISO 3 2 1 3 2 4 3\nA 2\nR1\nA 3\nR2\nA 4\nR3\nA 6\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7098549274637319, 0.6951830813743286, 0.76088044022011, 0.8246054635450812 ], "category_id": 1, "smiles": "[Pt]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 2.3905 -5.8504 0.0000 Pt 0 0 0 0 0 15 0 0 0 0 0 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.8019009504752376, 0.5743888580149594, 0.9534767383691846, 0.9108870516589163 ], "category_id": 1, "smiles": "*C(=O)C(*)([2*])[3*]", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 3.7962 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2360 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4448 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4448 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0933 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0 0 0 0 0 0 0 0 0\n 3.3644 -4.2756 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 3.9625 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0839 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6353 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6353 -6.5591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8502 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2707 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8877 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1587 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4297 -1.9134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7006 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0464 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7006 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1587 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 11 12 1 0\n 13 14 1 0\n 14 15 1 0\n 14 19 2 0\n 15 16 1 0\n 16 17 1 0\n 16 18 2 0\nM CHG 1 6 1\nM ISO 2 5 2 7 7\nA 5\nR2\nA 7\nR7\nA 8\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3871935967983992, 0.6059399460209146, 0.5287643821910956, 0.8834544517767866 ], "category_id": 1, "smiles": "*N([1*])(C(C)=O)C([2*])OC(C)=O", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 3.5490 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.3481 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9510 2.0490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7010 3.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.2010 3.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9510 4.6471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -1.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\nM ISO 2 4 1 7 2\nA 4\nR1\nA 5\nR\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3871935967983992, 0.6059399460209146, 0.5287643821910956, 0.8834544517767866 ], "category_id": 1, "smiles": "*N([1*])(C(C)=O)C([2*])OC(C)=O", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 3.5490 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.3481 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9510 2.0490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7010 3.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.2010 3.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9510 4.6471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -1.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 9 10 1 0\n 9 11 2 0\nM ISO 2 4 1 7 2\nA 4\nR1\nA 5\nR\nA 7\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5632816408204102, 0.6887949963005455, 0.6468234117058529, 0.7536814814592926 ], "category_id": 2, "text": [ "AczO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6848424212106053, 0.6428753298805091, 0.776888444222111, 0.8465190679171921 ], "category_id": 1, "smiles": "*N([1*])C(C)=O", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 8.5574 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9902 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5656 -3.4882 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1410 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5656 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9902 -7.7402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 6 2 0\n 3 4 1 0\n 3 5 1 0\nM ISO 1 5 1\nA 4\nR\nA 5\nR1\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.8194097048524263, 0.6648369094727005, 0.894447223611806, 0.8035941623506364 ], "category_id": 1, "smiles": "[2*]C([H])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.7152 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3885 -6.7953 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2979 -7.2677 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7152 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 1 2 2\nA 2\nR2\nM END\n" } ] } ], "Polonovski\u2013Potier rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.16108054027013508, 0.11870873517253983, 0.32416208104052024, 0.267352716605981 ], "category_id": 1, "smiles": "O=C(OC(=O)C(F)(F)F)C(F)(F)F", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 14.6352 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.0262 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2441 -6.5591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8530 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2835 -6.5591 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8530 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.6352 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\nA 2\nCF3\nA 5\nF3C\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.35467733866933465, 0.19715972537352267, 0.44372186093046523, 0.2559979680242598 ], "category_id": 2, "text": [ "acylation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5127563781890946, 0.09806373775122855, 0.6728364182091046, 0.3065782117064724 ], "category_id": 1, "smiles": "O=C([O-])C(F)(F)F.[H][IH]1([H])CCCCN1C", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 0.6224 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9876 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4773 -2.0709 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9711 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4773 -4.9055 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4773 -7.8189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4773 -7.0315 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9876 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6224 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7098 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5729 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3405 -2.1496 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 8.3405 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 9 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 2 0\nM CHG 1 12 -1\nA 11\nCF3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5127563781890946, 0.09806373775122855, 0.6728364182091046, 0.3065782117064724 ], "category_id": 1, "smiles": "O=C([O-])C(F)(F)F.[H][IH]1([H])CCCCN1C", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 0.6224 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9876 -0.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4773 -2.0709 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9711 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4773 -4.9055 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4773 -7.8189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4773 -7.0315 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9876 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6224 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7098 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.5729 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3405 -2.1496 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 8.3405 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 9 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 2 0\nM CHG 1 12 -1\nA 11\nCF3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8184092046023012, 0.06916074136139277, 0.9019509754877438, 0.28490096441409557 ], "category_id": 1, "smiles": "[H]C1C=[N+](C)CCC1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 7.5417 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1535 -1.0472 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 2.8281 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5656 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5656 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8281 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8281 -7.8189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1535 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\nM CHG 1 2 1\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.7348674337168585, 0.3458037068069638, 0.8254127063531765, 0.4273514466211434 ], "category_id": 2, "text": [ "CF3COz" ] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.26463231615807903, 0.5326409334698309, 0.3501750875437719, 0.674059165805813 ], "category_id": 1, "smiles": "C[N+]1C=CCCC1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 11.7456 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0936 -2.1496 0.0000 N 0 0 0 0 0 3 0 0 0 0 0 0\n 8.0936 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4416 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7896 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7896 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4416 0.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 2 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\nM CHG 1 2 1\nM RAD 1 2 2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.19859929964982492, 0.7236071596169602, 0.3631815907953977, 0.8660576418240079 ], "category_id": 1, "smiles": "C=C(OC(=O)C(F)(F)F)C(F)(F)F", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 15.3346 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.3346 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.8878 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7815 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2283 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4882 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2283 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\nA 3\nCF3\nA 6\nF3C\nM END\n" } ], "conditions": [], "products": [ { "category": "[Txt]", "bbox": [ 0.45972986493246626, 0.6565109179976986, 0.5467733866933466, 0.7463166567804026 ], "category_id": 2, "text": [ "CF3CO2" ] }, { "category": "[Mol]", "bbox": [ 0.5672836418209104, 0.5749631781835189, 0.6683341670835418, 0.8361223955631066 ], "category_id": 1, "smiles": "[H]C1(C(=O)C(F)(F)F)C=[N+](C)CCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 7.5245 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4378 -0.7323 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 3.4145 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3911 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3911 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4145 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3911 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4145 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4378 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3911 -7.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4378 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 11 1 0\n 8 9 1 0\n 8 10 2 0\nM CHG 1 2 1\nA 9\nCF3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5672836418209104, 0.5749631781835189, 0.6683341670835418, 0.8361223955631066 ], "category_id": 1, "smiles": "[H]C1(C(=O)C(F)(F)F)C=[N+](C)CCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 7.5245 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4378 -0.7323 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 3.4145 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3911 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3911 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4145 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3911 -5.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4145 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4378 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3911 -7.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4378 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 11 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 11 1 0\n 8 9 1 0\n 8 10 2 0\nM CHG 1 2 1\nA 9\nCF3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7628814407203601, 0.5718664285703223, 0.8589294647323662, 0.8330256459499099 ], "category_id": 1, "smiles": "CN1C=C(C(=O)C(F)(F)F)CCC1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 7.1527 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1091 -0.7323 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1091 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0053 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0053 -6.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1091 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9617 -7.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0218 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0218 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0053 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 1 0\n 3 4 2 0\n 4 5 1 0\n 4 8 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 1 0\n 9 10 1 0\nA 6\nCF3\nM END\n" } ] } ], "Pomeranz\u2013Fritsch reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.07403701850925462, 0.13073552805996094, 0.20860430215107553, 0.3313611182903412 ], "category_id": 1, "smiles": "[H]C(=O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 0.5201 -1.2047 0.0000 C 0 0 0 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0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\nA 1\nOEt\nA 3\nOEt\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.36368184092046024, 0.135668944213167, 0.5147573786893447, 0.18911428587289944 ], "category_id": 2, "text": [ "condensation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5557778889444722, 0.045222981404389, 0.7748874437218609, 0.35602819905637156 ], "category_id": 1, "smiles": "[H]N(CC(OCC)OCC)=C([OH2])C1=CC=CC=C1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 7.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 -3.8971 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 1.2990 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 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3.7500 1.2990 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 3\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 14 2 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\nA 1\nOEt\nA 3\nOEt\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.8304152076038019, 0.12251316780461746, 0.9109554777388694, 0.17513627343881558 ], "category_id": 2, "text": [ "imine" ] }, { "category": "[Txt]", "bbox": [ 0.8149074537268635, 0.2006255902303803, 0.9249624812406203, 0.2540709318901127 ], "category_id": 2, "text": [ "formation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.060030015007503754, 0.49005267121846985, 0.2786393196598299, 0.6939672055509876 ], "category_id": 1, "smiles": "CCOC(C/N=C\\c1ccccc1)OCC", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 14.5989 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2352 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2352 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0106 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0106 -7.1890 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6470 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2834 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9198 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5561 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5561 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9198 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2834 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\nA 1\nOEt\nA 3\nOEt\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.060030015007503754, 0.49005267121846985, 0.2786393196598299, 0.6939672055509876 ], "category_id": 1, "smiles": "CCOC(C/N=C\\c1ccccc1)OCC", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 14.5989 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2352 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2352 -0.1811 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0106 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0106 -7.1890 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6470 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2834 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9198 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5561 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5561 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9198 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2834 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 7 12 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\nA 1\nOEt\nA 3\nOEt\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.38469234617308656, 0.4218070810991192, 0.6038019009504753, 0.6602555285040793 ], "category_id": 1, "smiles": "CCOCC/N=C\\c1ccccc1.[H]OCC", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 10.4470 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4652 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4288 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4288 -7.5039 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4107 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3925 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4930 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4749 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4749 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4930 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3925 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4470 -1.5984 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4288 -0.4173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 12 13 1 0\nA 2\nOEt\nA 12\nOEt\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.38469234617308656, 0.4218070810991192, 0.6038019009504753, 0.6602555285040793 ], "category_id": 1, "smiles": "CCOCC/N=C\\c1ccccc1.[H]OCC", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 10.4470 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4652 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4288 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4288 -7.5039 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4107 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3925 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4930 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4749 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4749 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4930 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3925 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4470 -1.5984 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4288 -0.4173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\n 6 11 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 2 0\n 12 13 1 0\nA 2\nOEt\nA 12\nOEt\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6398199099549775, 0.48594149109079815, 0.7433716858429215, 0.5541870812101488 ], "category_id": 2, "text": [ "HOEt" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7738869434717359, 0.40865130469056965, 0.9609804902451226, 0.6495664601721328 ], "category_id": 1, "smiles": "CCO=CC/N=C\\c1ccccc1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 10.5019 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4823 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4823 -7.5039 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4627 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4431 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5245 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5049 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5049 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5245 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4431 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5019 -1.5984 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 2 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 5 10 1 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\nA 11\nOEt\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7738869434717359, 0.40865130469056965, 0.9609804902451226, 0.6495664601721328 ], "category_id": 1, "smiles": "CCO=CC/N=C\\c1ccccc1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 10.5019 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4823 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4823 -7.5039 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4627 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4431 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5245 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5049 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5049 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5245 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4431 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5019 -1.5984 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 2 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 5 6 2 0\n 5 10 1 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\nA 11\nOEt\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.2306153076538269, 0.7753685720788878, 0.37018509254627313, 0.9768163983348024 ], "category_id": 1, "smiles": "CCOC1CN=Cc2ccccc21", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 7.8110 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8110 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4145 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0179 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5326 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5326 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0179 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4145 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8110 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2076 -7.1102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2076 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 11 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 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0 0 0 0 0 0 0 0\n 5.4745 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2678 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3061 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3061 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0050 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6096 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6096 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0050 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3061 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7755 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4745 -5.3780 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4745 -7.2677 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1734 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0765 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\n 14 18 2 0\n 15 16 1 0\n 16 17 2 0\nA 7\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.030015007503751877, 0.3517241149692983, 0.24362181090545273, 0.5486674285562082 ], "category_id": 1, "smiles": "O=NNc1ccccc1/C=C(/C(=O)O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 0.3775 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3775 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0765 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7755 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4745 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2678 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3061 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3061 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0050 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6096 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6096 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0050 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3061 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7755 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4745 -5.3780 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4745 -7.2677 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1734 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0765 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\n 14 18 2 0\n 15 16 1 0\n 16 17 2 0\nA 7\nCO2H\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2736368184092046, 0.39166754758410816, 0.32416208104052024, 0.43993252866033683 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3661830915457729, 0.3367453277387446, 0.5787893946973487, 0.5725225341456086 ], "category_id": 1, "smiles": "[H]O=NN([H])C1=C(C=C(C(=O)O)C2=CC=CC=C2)C=CC=C1", "molfile": "\n RDKit 2D\n\n 20 21 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 3.8971 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 20 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 2 3\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 13 2 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 14 15 1 0\n 14 20 1 0\n 15 16 1 0\n 15 17 1 0\n 17 18 2 3\n 18 19 1 0\nA 7\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3661830915457729, 0.3367453277387446, 0.5787893946973487, 0.5725225341456086 ], "category_id": 1, "smiles": "[H]O=NN([H])C1=C(C=C(C(=O)O)C2=CC=CC=C2)C=CC=C1", "molfile": "\n RDKit 2D\n\n 20 21 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 3.8971 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 20 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 2 3\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 13 2 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 14 15 1 0\n 14 20 1 0\n 15 16 1 0\n 15 17 1 0\n 17 18 2 3\n 18 19 1 0\nA 7\nCO2H\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6118059029514757, 0.3944413970712478, 0.663831915957979, 0.4438159179423322 ], "category_id": 2, "text": [ "H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7013506753376688, 0.33951917722588415, 0.9139569784892446, 0.5458935790690687 ], "category_id": 1, "smiles": "O=C(O)/C(=C/c1ccccc1/N=N/[O-])c1ccccc1", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 0.3591 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3591 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9752 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5015 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1176 -5.0630 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1176 -7.0315 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7337 -7.9764 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 3.5015 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1176 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9133 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9009 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9009 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5170 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0433 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0433 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5170 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9009 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9752 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 8 1 0\n 5 6 2 0\n 6 7 1 0\n 8 9 1 0\n 8 18 2 0\n 9 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 12 17 1 0\n 13 14 1 0\n 14 15 2 0\n 15 16 1 0\n 16 17 2 0\nM CHG 1 7 -1\nA 11\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7013506753376688, 0.33951917722588415, 0.9139569784892446, 0.5458935790690687 ], "category_id": 1, "smiles": "O=C(O)/C(=C/c1ccccc1/N=N/[O-])c1ccccc1", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 0.3591 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3591 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9752 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5015 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1176 -5.0630 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1176 -7.0315 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7337 -7.9764 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 3.5015 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1176 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9133 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9009 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9009 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5170 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0433 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0433 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5170 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9009 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9752 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 18 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 8 1 0\n 5 6 2 0\n 6 7 1 0\n 8 9 1 0\n 8 18 2 0\n 9 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 12 17 1 0\n 13 14 1 0\n 14 15 2 0\n 15 16 1 0\n 16 17 2 0\nM CHG 1 7 -1\nA 11\nCO2H\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.04202101050525263, 0.6851408233234754, 0.12056028014007003, 0.727303335527997 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.1570785392696348, 0.641868771324098, 0.37018509254627313, 0.7877732543476398 ], "category_id": 1, "smiles": "N=Nc1ccccc1/C=C(/C(=O)O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 0.5149 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5149 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8319 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0202 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3372 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9117 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1989 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3276 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5159 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.8329 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.8329 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5159 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3276 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0202 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3372 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8319 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 16 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\n 14 16 2 0\nA 7\nCO2H\nA 15\nN2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1570785392696348, 0.641868771324098, 0.37018509254627313, 0.7877732543476398 ], "category_id": 1, "smiles": "N=Nc1ccccc1/C=C(/C(=O)O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 0.5149 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5149 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8319 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0202 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3372 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9117 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1989 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3276 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5159 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.8329 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.8329 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5159 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3276 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0202 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3372 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8319 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 16 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\n 14 16 2 0\nA 7\nCO2H\nA 15\nN2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4047023511755878, 0.681812203938908, 0.4752376188094047, 0.7212008666562899 ], "category_id": 2, "text": [ "Cu(o)" ] } ], "products": [ { "category": "[Txt]", "bbox": [ 0.512256128064032, 0.700674380451457, 0.576288144072036, 0.740617813066267 ], "category_id": 2, "text": [ "Cu(l)" ] }, { "category": "[Mol]", "bbox": [ 0.6088044022011005, 0.6357663024523909, 0.8214107053526764, 0.7888827941424956 ], "category_id": 1, "smiles": "[H]/C=C/C=C\\C=C(I)\\C(=C/c1ccccc1)C(=O)O", "molfile": "\n RDKit 2D\n\n 17 17 0 0 0 0 0 0 0 0999 V2000\n 0.4868 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4868 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6772 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7459 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9363 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4918 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7087 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7087 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7087 -5.0630 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8991 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9678 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9678 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8991 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7087 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5183 -7.9764 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7459 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6772 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 17 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 16 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 16 17 2 0\nA 7\nCO2H\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.8604302151075538, 0.6923528319900383, 0.9119559779889945, 0.7395082732714111 ], "category_id": 2, "text": [ "Nzt" ] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1570785392696348, 0.641868771324098, 0.37018509254627313, 0.7877732543476398 ], "category_id": 1, "smiles": "N=Nc1ccccc1/C=C(/C(=O)O)c1ccccc1", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 0.5149 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5149 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8319 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0202 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3372 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9117 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1989 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3276 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5159 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.8329 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.8329 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.5159 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.3276 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0202 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3372 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8319 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 16 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\n 14 16 2 0\nA 7\nCO2H\nA 15\nN2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.08604302151075538, 0.8521265624492779, 0.2016008004002001, 0.8898509154743761 ], "category_id": 2, "text": [ "6-exo-trig" ] }, { "category": "[Txt]", "bbox": [ 0.04402201100550275, 0.9048297027049298, 0.24262131065532766, 0.9419992858326002 ], "category_id": 2, "text": [ "radical cyclization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.25962981490745374, 0.8243880675778821, 0.471735867933967, 0.9775045592679867 ], "category_id": 1, "smiles": "[H]C12CC=CC=C1C(C(=O)O)=Cc1ccccc12", "molfile": "\n RDKit 2D\n\n 16 18 0 0 0 0 0 0 0 0999 V2000\n 7.0001 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0001 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7070 -6.1654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0519 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0519 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1037 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0001 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8277 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6552 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4828 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4828 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6552 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8277 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2243 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2243 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0519 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 16 1 0\n 2 3 1 0\n 2 4 1 0\n 2 13 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\n 15 16 2 0\nA 6\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.25962981490745374, 0.8243880675778821, 0.471735867933967, 0.9775045592679867 ], "category_id": 1, "smiles": "[H]C12CC=CC=C1C(C(=O)O)=Cc1ccccc12", "molfile": "\n RDKit 2D\n\n 16 18 0 0 0 0 0 0 0 0999 V2000\n 7.0001 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0001 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7070 -6.1654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0519 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0519 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1037 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0001 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8277 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6552 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4828 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4828 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6552 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8277 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2243 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2243 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0519 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 16 1 0\n 2 3 1 0\n 2 4 1 0\n 2 13 1 0\n 4 5 1 0\n 4 14 2 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 2 0\n 8 13 1 0\n 9 10 1 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 14 15 1 0\n 15 16 2 0\nA 6\nCO2H\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.48874437218609307, 0.8504622527569942, 0.5552776388194097, 0.8892961455769481 ], "category_id": 2, "text": [ "Cu(l)" ] }, { "category": "[Txt]", "bbox": [ 0.4932466233116558, 0.9048297027049298, 0.5632816408204102, 0.9481017547043072 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Txt]", "bbox": [ 0.5957978989494748, 0.877091207833534, 0.6658329164582291, 0.9181441802431998 ], "category_id": 2, "text": [ "Cu(o)" ] }, { "category": "[Mol]", "bbox": [ 0.6993496748374187, 0.8193951385010309, 0.9109554777388694, 0.9719568602937076 ], "category_id": 1, "smiles": "O=C(O)c1cc2ccccc2c2ccccc12", "molfile": "\n RDKit 2D\n\n 15 17 0 0 0 0 0 0 0 0999 V2000\n 0.4816 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4816 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6485 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8155 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8621 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0291 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0291 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0757 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8621 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8155 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6485 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0757 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0757 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0291 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8621 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 2 0\n 5 15 1 0\n 6 7 1 0\n 6 12 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 10 11 2 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\nA 8\nCO2H\nM END\n" } ] } ], "Pummerer rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.17658829414707353, 0.1111389027847257, 0.3031515757878939, 0.30403515934212316 ], "category_id": 1, "smiles": "CC(=O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.7942 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6331 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4720 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1785 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0173 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1785 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6331 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3411705852926463, 0.2644339411084853, 0.39869934967483744, 0.34874621218655305 ], "category_id": 2, "text": [ "acyl" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.45072536268134067, 0.13413315853328964, 0.6048024012006002, 0.5263129649115745 ], "category_id": 1, "smiles": "[2*]C[SiH]([7*])OC(C)(O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 9.1986 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0885 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9474 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8372 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0133 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0133 -6.8740 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 1.2688 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8372 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7404 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8063 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7404 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1986 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 4 5 1 0\n 4 10 1 0\n 4 11 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\nM ISO 2 7 7 9 2\nA 7\nR7\nA 9\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45072536268134067, 0.13413315853328964, 0.6048024012006002, 0.5263129649115745 ], "category_id": 1, "smiles": "[2*]C[SiH]([7*])OC(C)(O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 9.1986 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0885 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9474 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8372 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0133 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0133 -6.8740 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 1.2688 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8372 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7404 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8063 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7404 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1986 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 4 5 1 0\n 4 10 1 0\n 4 11 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\nM ISO 2 7 7 9 2\nA 7\nR7\nA 9\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.32566283141570784, 0.3909023477255869, 0.4137068534267134, 0.4637174909293727 ], "category_id": 2, "text": [ "transfer" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.17658829414707353, 0.1111389027847257, 0.3031515757878939, 0.30403515934212316 ], "category_id": 1, "smiles": "CC(=O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.7942 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6331 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4720 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1785 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0173 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1785 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6331 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45072536268134067, 0.13413315853328964, 0.6048024012006002, 0.5263129649115745 ], "category_id": 1, "smiles": "[2*]C[SiH]([7*])OC(C)(O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 9.1986 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0885 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9474 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8372 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0133 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0133 -6.8740 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 1.2688 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8372 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7404 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8063 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7404 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1986 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 4 5 1 0\n 4 10 1 0\n 4 11 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\nM ISO 2 7 7 9 2\nA 7\nR7\nA 9\nR2\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.6448224112056028, 0.24143968535992133, 0.7313656828414207, 0.357688422755439 ], "category_id": 1, "smiles": "CC", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 1.0367 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.7728 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7938969484742371, 0.0357688422755439, 0.9154577288644322, 0.4394457765281108 ], "category_id": 1, "smiles": "[1*][S+](OC(C)=O)C([2*])[H]", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 6.3424 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5907 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8390 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8390 -4.9055 0.0000 S 0 0 0 0 0 3 0 0 0 0 0 0\n 1.0269 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5907 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3424 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5907 -7.9764 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5907 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\nM CHG 1 4 1\nM ISO 2 5 1 7 2\nA 5\nR1\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7938969484742371, 0.0357688422755439, 0.9154577288644322, 0.4394457765281108 ], "category_id": 1, "smiles": "[1*][S+](OC(C)=O)C([2*])[H]", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 6.3424 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5907 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8390 -2.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8390 -4.9055 0.0000 S 0 0 0 0 0 3 0 0 0 0 0 0\n 1.0269 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5907 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3424 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5907 -7.9764 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5907 0.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 2 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\nM CHG 1 4 1\nM ISO 2 5 1 7 2\nA 5\nR1\nA 7\nR2\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7638819409704852, 0.47521461880365473, 0.8279139569784892, 0.5876309802410784 ], "category_id": 1, "smiles": "*", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 4.5295 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nAcO\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.45072536268134067, 0.13413315853328964, 0.6048024012006002, 0.5263129649115745 ], "category_id": 1, "smiles": "[2*]C[SiH]([7*])OC(C)(O)OC(C)=O", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 9.1986 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0885 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9474 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8372 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0133 -4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0133 -6.8740 0.0000 Si 0 0 0 0 0 4 0 0 0 0 0 0\n 1.2688 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8372 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7404 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8063 -1.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7404 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1986 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 12 2 0\n 3 4 1 0\n 4 5 1 0\n 4 10 1 0\n 4 11 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 8 9 1 0\nM ISO 2 7 7 9 2\nA 7\nR7\nA 9\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.27913956978489246, 0.6591686647921662, 0.4017008504252126, 0.8341805002117917 ], "category_id": 1, "smiles": "[1*]/[SH]=C/[2*]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 6.6379 -4.5906 0.0000 S 0 0 0 0 0 4 0 0 0 0 0 0\n 1.9773 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7337 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8294 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\nM ISO 2 2 1 4 2\nA 2\nR1\nA 4\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.1455727863931966, 0.6859952964988241, 0.24412206103051526, 0.766475191618798 ], "category_id": 2, "text": [ "HOAc" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.1025512756378189, 0.3295843323960831, 0.22311155577788894, 0.5735789350614005 ], "category_id": 1, "smiles": "[1*]S(O)C[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 7.4490 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3293 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5687 -5.6142 0.0000 S 0 0 0 0 0 3 0 0 0 0 0 0\n 1.3905 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5687 -2.3071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\nM RAD 1 3 2\nM ISO 2 2 2 4 1\nA 2\nR2\nA 4\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.27913956978489246, 0.6591686647921662, 0.4017008504252126, 0.8341805002117917 ], "category_id": 1, "smiles": "[1*]/[SH]=C/[2*]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 6.6379 -4.5906 0.0000 S 0 0 0 0 0 4 0 0 0 0 0 0\n 1.9773 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7337 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8294 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\nM ISO 2 2 1 4 2\nA 2\nR1\nA 4\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5352676338169085, 0.6336194917382062, 0.6593296648324162, 0.7792497781457779 ], "category_id": 1, "smiles": "[1*]SC[2*]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 13.1193 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1254 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9406 -2.1496 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5893 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\nM ISO 2 2 2 4 1\nA 2\nR2\nA 4\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5352676338169085, 0.6336194917382062, 0.6593296648324162, 0.7792497781457779 ], "category_id": 1, "smiles": "[1*]SC[2*]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 13.1193 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1254 -2.1496 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9406 -2.1496 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5893 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\nM ISO 2 2 2 4 1\nA 2\nR2\nA 4\nR1\nM 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"reactants": [ { "category": "[Mol]", "bbox": [ 0.011005502751375688, 0.08506928361299991, 0.2061030515257629, 0.839716154373483 ], "category_id": 1, "smiles": "[1*]C([2*])(C)C(=O)C([3*])([4*])[5*]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 1.4493 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5708 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5708 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8952 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0235 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5876 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5876 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1517 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1517 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0235 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 5 10 2 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\nM ISO 5 3 2 4 1 7 5 8 3 9 4\nA 3\nR2\nA 4\nR1\nA 7\nR5\nA 8\nR3\nA 9\nR4\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 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"products": [ { "category": "[Mol]", "bbox": [ 0.1360680340170085, 0.7147275295106117, 0.38369184592296146, 0.9357772809056462 ], "category_id": 1, "smiles": "*C(*)([1*])CC(=O)O[2*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 11.7378 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0426 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7378 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0426 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4331 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.9109 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 22.6062 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.9109 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\nM ISO 1 3 1\nA 2\nBrZnO\nA 3\nR1\nA 4\nR\nA 7\nOR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1360680340170085, 0.7147275295106117, 0.38369184592296146, 0.9357772809056462 ], "category_id": 1, "smiles": "*C(*)([1*])CC(=O)O[2*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 11.7378 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0426 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7378 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0426 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.4331 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.9109 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 22.6062 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 18.9109 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\nM ISO 1 3 1\nA 2\nBrZnO\nA 3\nR1\nA 4\nR\nA 7\nOR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.43771885942971483, 0.6877103376734408, 0.6283141570785392, 0.7761302382314546 ], "category_id": 2, "text": [ "HzO, hydrolysis" ] }, { "category": "[Txt]", "bbox": [ 0.4427213606803402, 0.8264804593825458, 0.6203101550775387, 0.9136723057661428 ], "category_id": 2, "text": [ "during workup" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6773386693346674, 0.6778859042781059, 0.8859429714857429, 0.9013917640219741 ], "category_id": 1, "smiles": "*C([1*])(O)CC(=O)O[2*]", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 7.1741 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1741 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5871 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5871 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7612 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3482 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 17.7559 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.3482 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\nM ISO 1 2 1\nA 2\nR1\nA 3\nR\nA 7\nOR2\nM END\n" } ] } ], "Regitz diazo synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04452226113056528, 0.19570111142527785, 0.18859429714857429, 0.3965795009305895 ], "category_id": 1, "smiles": "*OC(=O)C([H])C(*)=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 6.3569 -3.0945 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0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5178 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 9 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 9 10 1 0\n 9 11 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4182091045522761, 0.6765398711000333, 0.5597798899449725, 0.9259957489661862 ], "category_id": 1, "smiles": "[H]C(O)(Cl)c1ccccc1O", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 0.5178 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5890 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6602 -7.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6602 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7313 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8025 -4.9843 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7313 -1.4409 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8025 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5890 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5890 -1.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5178 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 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10 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6283141570785392, 0.6755692256608654, 0.7528764382191095, 0.9201718763311787 ], "category_id": 1, "smiles": "[H]C1=C2C=CC=CC2=O[H]O1", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 2 0\n 4 10 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\n 10 11 1 0\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8239119559779889, 0.6843050346133766, 0.9534767383691846, 0.9007589675478205 ], "category_id": 1, "smiles": "O=Cc1ccccc1O", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 0.5512 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5512 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0315 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0315 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4199 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7165 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4199 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0315 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 8 1 0\n 2 3 1 0\n 3 4 1 0\n 3 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\nA 6\nCHO\nM END\n" } ] } ], "Reissert indole synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.11505752876438219, 0.09495707853926963, 0.23311655827913957, 0.2838043021510755 ], "category_id": 1, "smiles": "Cc1ccccc1[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 9.1088 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3866 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3866 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1088 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4550 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6282 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6282 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4550 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 8 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\nA 4\nNO2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2651325662831416, 0.07788614307153575, 0.3046523261630815, 0.1557722861430715 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3291645822911456, 0.09709094547273636, 0.4462231115557779, 0.2859381690845423 ], "category_id": 1, "smiles": "Cc1ccccc1[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 9.0612 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2810 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2810 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0612 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3979 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6178 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6178 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3979 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 8 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\nA 4\nNO2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3291645822911456, 0.09709094547273636, 0.4462231115557779, 0.2859381690845423 ], "category_id": 1, "smiles": "Cc1ccccc1[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 9.0612 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2810 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2810 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0612 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3979 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6178 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6178 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3979 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 8 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\nA 4\nNO2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.11505752876438219, 0.09495707853926963, 0.23311655827913957, 0.2838043021510755 ], "category_id": 1, "smiles": "Cc1ccccc1[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 9.1088 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3866 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3866 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1088 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4550 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6282 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6282 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4550 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 8 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\nA 4\nNO2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3291645822911456, 0.09709094547273636, 0.4462231115557779, 0.2859381690845423 ], "category_id": 1, "smiles": "Cc1ccccc1[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 9.0612 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2810 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2810 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0612 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3979 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6178 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6178 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3979 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 8 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\nA 4\nNO2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.45672836418209106, 0.0832208104052026, 0.5707853926963482, 0.27420190095047525 ], "category_id": 1, "smiles": "CCOC(=O)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.5048 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3086 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0123 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2085 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0123 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4047 -7.5039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 4 5 1 0\n 4 6 2 0\nA 1\nEtO\nA 5\nOEt\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45672836418209106, 0.0832208104052026, 0.5707853926963482, 0.27420190095047525 ], "category_id": 1, "smiles": "CCOC(=O)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.5048 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3086 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0123 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2085 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0123 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4047 -7.5039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 4 5 1 0\n 4 6 2 0\nA 1\nEtO\nA 5\nOEt\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6118059029514757, 0.07788614307153575, 0.656328164082041, 0.1653746873436718 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6783391695847923, 0.0448112056028014, 0.8489244622311155, 0.2774027013506753 ], "category_id": 1, "smiles": "CCOC(=O)C(O)(Cc1ccccc1[N+](=O)[O-])OCC", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 9.8425 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8425 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7953 -3.5669 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0728 -0.8898 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.5049 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1673 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1673 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5049 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8297 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6152 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6152 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8297 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 6 7 2 0\n 6 12 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\nM RAD 1 4 2\nA 1\nCO2Et\nA 3\nOEt\nA 8\nNO2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6783391695847923, 0.0448112056028014, 0.8489244622311155, 0.2774027013506753 ], "category_id": 1, "smiles": "CCOC(=O)C(O)(Cc1ccccc1[N+](=O)[O-])OCC", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 9.8425 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8425 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7953 -3.5669 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0728 -0.8898 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.5049 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1673 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1673 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5049 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8297 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6152 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6152 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8297 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 6 7 2 0\n 6 12 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\nM RAD 1 4 2\nA 1\nCO2Et\nA 3\nOEt\nA 8\nNO2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3291645822911456, 0.09709094547273636, 0.4462231115557779, 0.2859381690845423 ], "category_id": 1, "smiles": "Cc1ccccc1[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 9.0612 -0.4961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2810 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2810 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0612 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3979 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6178 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6178 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3979 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 8 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\nA 4\nNO2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6783391695847923, 0.0448112056028014, 0.8489244622311155, 0.2774027013506753 ], "category_id": 1, "smiles": "CCOC(=O)C(O)(Cc1ccccc1[N+](=O)[O-])OCC", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 9.8425 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8425 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7953 -3.5669 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0728 -0.8898 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 7.5049 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1673 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1673 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5049 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8297 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6152 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6152 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8297 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\n 5 6 1 0\n 6 7 2 0\n 6 12 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\nM RAD 1 4 2\nA 1\nCO2Et\nA 3\nOEt\nA 8\nNO2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.45722861430715356, 0.0832208104052026, 0.5707853926963482, 0.27420190095047525 ], "category_id": 1, "smiles": "CCOC(=O)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 3.4748 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2547 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9353 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1554 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9353 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3756 -7.5039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 4 5 1 0\n 4 6 2 0\nA 1\nEtO\nA 5\nOEt\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.22311155577788894, 0.3904976488244122, 0.3876938469234617, 0.5804118059029515 ], "category_id": 1, "smiles": "CCOC(=O)C(=O)Cc1ccccc1[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 12.0654 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0654 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3035 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3961 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3961 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3035 -6.9528 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4888 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7268 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7268 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4888 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.9727 -0.4961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 11 2 0\n 3 4 1 0\n 4 5 2 0\n 4 10 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\nA 2\nCO2Et\nA 6\nNO2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4132066033016508, 0.4235725862931466, 0.5147573786893447, 0.491856328164082 ], "category_id": 2, "text": [ "hydrolysis" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5617808904452226, 0.39476538269134565, 0.7198599299649825, 0.5846795397698848 ], "category_id": 1, "smiles": "O=C(O)C(=O)Cc1ccccc1[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 0.7009 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5044 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4480 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3917 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1952 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1952 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1389 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4480 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3917 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5044 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7009 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 2 0\nA 6\nCO2H\nA 9\nNO2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5617808904452226, 0.39476538269134565, 0.7198599299649825, 0.5846795397698848 ], "category_id": 1, "smiles": "O=C(O)C(=O)Cc1ccccc1[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 0.7009 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5044 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4480 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3917 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1952 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1952 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1389 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4480 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3917 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5044 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7009 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 2 0\nA 6\nCO2H\nA 9\nNO2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7458729364682342, 0.416104052026013, 0.7933966983491746, 0.48225392696348174 ], "category_id": 2, "text": [ "[A]" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.02751375687843922, 0.6881720860430215, 0.20860430215107553, 0.9421022511255628 ], "category_id": 1, "smiles": "Nc1ccccc1CC(=O)C(=O)O.[H]", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 0.4776 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6268 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6566 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8059 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9551 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9551 -6.4016 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1043 -2.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6566 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8059 -7.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6268 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4776 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6565 -1.2047 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 2 0\nA 6\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.02751375687843922, 0.6881720860430215, 0.20860430215107553, 0.9421022511255628 ], "category_id": 1, "smiles": "Nc1ccccc1CC(=O)C(=O)O.[H]", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 0.4776 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6268 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6566 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8059 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9551 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9551 -6.4016 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1043 -2.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6566 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8059 -7.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6268 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4776 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6565 -1.2047 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 2 0\nA 6\nCO2H\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.271135567783892, 0.7404518259129564, 0.44372186093046523, 0.9335667833916957 ], "category_id": 1, "smiles": "O=C(O)C1(O)=[NH+]C2=CC=CC=C2C1", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n -1.2135 -2.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2135 -2.7256 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 0.0000 -3.6073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0037 -4.7220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0037 -4.7220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 9 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\nM CHG 1 8 1\nA 10\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.271135567783892, 0.7404518259129564, 0.44372186093046523, 0.9335667833916957 ], "category_id": 1, "smiles": "O=C(O)C1(O)=[NH+]C2=CC=CC=C2C1", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n -1.2135 -2.7256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2135 -2.7256 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 0.0000 -3.6073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0037 -4.7220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0037 -4.7220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 9 1 0\n 2 3 1 0\n 2 7 2 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 8 9 2 0\n 9 10 1 0\n 9 11 1 0\nM CHG 1 8 1\nA 10\nCO2H\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5147573786893447, 0.6881720860430215, 0.696848424212106, 0.9389014507253627 ], "category_id": 1, "smiles": "[H]C1C(C(=O)O)=[NH+]c2ccccc21", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 7.2008 -2.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9331 -0.0236 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7598 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7598 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6850 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4882 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4882 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6850 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2008 -6.4803 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.6654 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.2283 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 1 0\n 3 4 2 0\n 3 8 1 0\n 4 5 1 0\n 4 9 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 9 10 2 0\n 10 11 1 0\nM CHG 1 9 1\nA 11\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5147573786893447, 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0.9474737368684342, 0.919696648324162 ], "category_id": 1, "smiles": "O=C(O)c1cc2ccccc2[nH]1", "molfile": "\n RDKit 2D\n\n 10 11 0 0 0 0 0 0 0 0999 V2000\n 0.6474 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5608 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4742 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5494 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4917 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8906 -2.9370 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5494 -5.7717 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4742 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5608 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6474 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 10 1 0\n 2 3 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 1 0\n 9 10 2 0\nA 6\nCO2H\nM END\n" } ] } ], "Reissert reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.030015007503751877, 0.04192665194872885, 0.18509254627313657, 0.15639306679287746 ], "category_id": 1, "smiles": 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0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 14 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 13 2 0\n 5 6 1 0\n 5 9 2 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 9 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 1 0\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2531265632816408, 0.05723320742207431, 0.3996998499249625, 0.22294330798133596 ], "category_id": 1, "smiles": "*C(=O)N1=C([H])C=CC2=C1C=CC=C2", "molfile": "\n RDKit 2D\n\n 14 15 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 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0.20564024527233676 ], "category_id": 1, "smiles": "*C(=O)N1c2ccccc2C=CC1([H])C#N", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 0.4743 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4743 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5612 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6481 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6402 -4.2756 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6402 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7271 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6481 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7271 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9603 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0986 -3.0945 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7271 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6402 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6481 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5612 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 1 0\n 5 9 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 9 11 1 0\n 9 12 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\nA 7\nR\nA 10\nCN\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4867433716858429, 0.03726813506553676, 0.6398199099549775, 0.20564024527233676 ], "category_id": 1, "smiles": "*C(=O)N1c2ccccc2C=CC1([H])C#N", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 0.4743 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4743 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5612 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6481 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6402 -4.2756 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6402 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7271 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6481 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7271 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9603 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0986 -3.0945 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7271 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6402 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6481 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5612 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 1 0\n 5 9 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 9 11 1 0\n 9 12 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\nA 7\nR\nA 10\nCN\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.6753376688344173, 0.061226221893381824, 0.7163581790895448, 0.12045593655110988 ], "category_id": 1, "smiles": "c1ccccc1", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 2.7979 -5.9291 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nA 1\nPh\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.743871935967984, 0.042592154360613435, 0.9154577288644322, 0.22427431280510512 ], "category_id": 1, "smiles": "*C(=O)N1C2=C(C=CC=C2)C=CC1([H])C#N[H]", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8991 0.3349 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8991 2.2632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.3086 1.7502 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -7.4577 2.7144 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 17 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 16 2 0\n 5 6 1 0\n 5 9 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 9 11 1 0\n 9 14 1 0\n 11 12 3 0\n 12 13 1 0\n 14 15 2 0\n 15 16 1 0\n 16 17 1 0\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.743871935967984, 0.042592154360613435, 0.9154577288644322, 0.22427431280510512 ], "category_id": 1, "smiles": "*C(=O)N1C2=C(C=CC=C2)C=CC1([H])C#N[H]", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8991 0.3349 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8991 2.2632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.3086 1.7502 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -7.4577 2.7144 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 17 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 16 2 0\n 5 6 1 0\n 5 9 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 9 11 1 0\n 9 14 1 0\n 11 12 3 0\n 12 13 1 0\n 14 15 2 0\n 15 16 1 0\n 16 17 1 0\nA 7\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4867433716858429, 0.03726813506553676, 0.6398199099549775, 0.20564024527233676 ], "category_id": 1, "smiles": "*C(=O)N1c2ccccc2C=CC1([H])C#N", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 0.4743 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4743 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5612 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6481 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6402 -4.2756 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6402 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7271 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6481 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7271 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9603 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0986 -3.0945 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7271 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6402 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6481 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5612 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 14 1 0\n 5 6 1 0\n 5 9 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 9 11 1 0\n 9 12 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\nA 7\nR\nA 10\nCN\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.743871935967984, 0.042592154360613435, 0.9154577288644322, 0.22427431280510512 ], "category_id": 1, "smiles": "*C(=O)N1C2=C(C=CC=C2)C=CC1([H])C#N[H]", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8991 0.3349 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8991 2.2632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.3086 1.7502 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -7.4577 2.7144 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 17 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 16 2 0\n 5 6 1 0\n 5 9 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 1 0\n 9 11 1 0\n 9 14 1 0\n 11 12 3 0\n 12 13 1 0\n 14 15 2 0\n 15 16 1 0\n 16 17 1 0\nA 7\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.0735367683841921, 0.3240996745877929, 0.2621310655327664, 0.5011233161490924 ], "category_id": 1, "smiles": "*C1=OC(=N)C2([H])C=CC3=C(C=CC=C3)N12", "molfile": "\n RDKit 2D\n\n 16 18 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.6317 2.5126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2172 0.9872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.3319 1.9909 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -5.3740 -0.5046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.0037 -1.1147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6918 -2.5819 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 16 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 4 15 2 0\n 5 6 1 0\n 5 11 1 0\n 6 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0\n -4.8991 -2.2632 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8991 -0.3349 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5000 0.0000 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n -0.0000 3.5981 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n 0.0000 5.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 5.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2990 5.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 15 1 0\n 2 3 2 0\n 3 4 1 0\n 3 10 1 0\n 4 5 2 0\n 4 14 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 2 0\n 11 12 1 0\n 11 13 2 0\n 14 15 2 0\n 17 18 2 0\n 18 19 1 0\n 18 20 1 0\nA 12\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3486743371685843, 0.31345163599763953, 0.5382691345672836, 0.5383914512146293 ], "category_id": 1, "smiles": "*C(=O)N1=C2C=CCC=C2C=CC1([H])[H].[H].[H]=C(O)O", "molfile": "\n RDKit 2D\n\n 20 19 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8991 -2.2632 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.8991 -0.3349 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -5.2500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5000 0.0000 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n -0.0000 3.5981 0.0000 H 0 0 0 0 0 2 0 0 0 0 0 0\n 0.0000 5.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 5.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2990 5.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 15 1 0\n 2 3 2 0\n 3 4 1 0\n 3 10 1 0\n 4 5 2 0\n 4 14 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 2 0\n 11 12 1 0\n 11 13 2 0\n 14 15 2 0\n 17 18 2 0\n 18 19 1 0\n 18 20 1 0\nA 12\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6113056528264132, 0.30812761670256283, 0.7998999499749875, 0.4984613065015542 ], "category_id": 1, "smiles": "*C1([H])OC(=N)c2ccc3ccccc3[n+]21.[H][O-]", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 6.3591 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8803 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0039 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3398 -6.2441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1738 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1545 -3.9606 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7143 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7143 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9421 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1699 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5019 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7297 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7297 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5019 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1699 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9421 -3.9606 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 10.2163 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9885 -0.9685 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 16 1 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 2 0\n 7 16 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 10 15 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 2 0\n 17 18 1 0\nM CHG 2 16 1 18 -1\nA 3\nR\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.8179089544772387, 0.3626988144770988, 0.8574287143571786, 0.41926651948728855 ], "category_id": 2, "text": [] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6113056528264132, 0.30812761670256283, 0.7998999499749875, 0.4984613065015542 ], "category_id": 1, "smiles": "*C1([H])OC(=N)c2ccc3ccccc3[n+]21.[H][O-]", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 6.3591 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8803 -8.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0039 -7.6614 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3398 -6.2441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1738 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1545 -3.9606 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7143 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7143 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9421 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1699 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5019 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7297 -0.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7297 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5019 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1699 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9421 -3.9606 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 10.2163 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9885 -0.9685 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 16 1 0\n 4 5 1 0\n 5 6 2 0\n 5 7 1 0\n 7 8 2 0\n 7 16 1 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 10 15 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 2 0\n 17 18 1 0\nM CHG 2 16 1 18 -1\nA 3\nR\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.8179089544772387, 0.3626988144770988, 0.8574287143571786, 0.41926651948728855 ], "category_id": 2, "text": [] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.04102051025512756, 0.5696700645732047, 0.24062031015507754, 0.7540142326652347 ], "category_id": 1, "smiles": "*C1([H])OC(N)(O)C2=N1C1=C(C=CC=C1)C=C2", "molfile": "\n RDKit 2D\n\n 17 19 0 0 0 0 0 0 0 0999 V2000\n -2.9672 -2.9099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1240 -1.4182 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.4672 -2.9099 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1240 -4.4017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7537 -5.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5402 -5.8935 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5037 -6.3109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 17 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 8 17 2 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\n 11 16 2 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\n 15 16 1 0\n 16 17 1 0\nA 3\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04102051025512756, 0.5696700645732047, 0.24062031015507754, 0.7540142326652347 ], "category_id": 1, "smiles": "*C1([H])OC(N)(O)C2=N1C1=C(C=CC=C1)C=C2", "molfile": "\n RDKit 2D\n\n 17 19 0 0 0 0 0 0 0 0999 V2000\n -2.9672 -2.9099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1240 -1.4182 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.4672 -2.9099 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1240 -4.4017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7537 -5.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5402 -5.8935 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5037 -6.3109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 17 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 8 17 2 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\n 11 16 2 0\n 12 13 2 0\n 13 14 1 0\n 14 15 2 0\n 15 16 1 0\n 16 17 1 0\nA 3\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3021510755377689, 0.5690045621613202, 0.4977488744372186, 0.7526832278414657 ], "category_id": 1, "smiles": "*C1([H])OC(N)(O[H])C2=N1C1=C(C=CC=C1)C=C2", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n -2.9672 -2.9099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1240 -1.4182 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.4672 -2.9099 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1240 -4.4017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7537 -5.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5402 -5.8935 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5037 -6.3109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.0037 -6.3109 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 18 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 9 1 0\n 7 8 1 0\n 9 10 1 0\n 9 18 2 0\n 10 11 2 0\n 11 12 1 0\n 12 13 1 0\n 12 17 2 0\n 13 14 2 0\n 14 15 1 0\n 15 16 2 0\n 16 17 1 0\n 17 18 1 0\nA 3\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3021510755377689, 0.5690045621613202, 0.4977488744372186, 0.7526832278414657 ], "category_id": 1, "smiles": "*C1([H])OC(N)(O[H])C2=N1C1=C(C=CC=C1)C=C2", "molfile": "\n RDKit 2D\n\n 18 20 0 0 0 0 0 0 0 0999 V2000\n -2.9672 -2.9099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1240 -1.4182 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -4.4672 -2.9099 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1240 -4.4017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7537 -5.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5402 -5.8935 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5037 -6.3109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.0037 -6.3109 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 18 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 9 1 0\n 7 8 1 0\n 9 10 1 0\n 9 18 2 0\n 10 11 2 0\n 11 12 1 0\n 12 13 1 0\n 12 17 2 0\n 13 14 2 0\n 14 15 1 0\n 15 16 2 0\n 16 17 1 0\n 17 18 1 0\nA 3\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5872936468234117, 0.5889696345178577, 0.6633316658329165, 0.6861329866530071 ], "category_id": 1, "smiles": "*C([H])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.0005 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2796 -7.2677 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5575 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0005 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nA 3\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.6838419209604802, 0.5636805428662435, 0.8579289644822411, 0.7160805951878134 ], "category_id": 1, "smiles": "NC(=O)c1ccc2ccccc2n1", "molfile": "\n RDKit 2D\n\n 13 14 0 0 0 0 0 0 0 0999 V2000\n 0.4765 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4765 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8593 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0038 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2674 -4.8268 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5310 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7946 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7946 -7.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0582 -3.4882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5310 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2674 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0038 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8593 0.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 13 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 12 1 0\n 5 6 2 0\n 6 7 1 0\n 6 10 1 0\n 7 8 1 0\n 7 9 2 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5872936468234117, 0.5889696345178577, 0.6633316658329165, 0.6861329866530071 ], "category_id": 1, "smiles": "*C([H])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.0005 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 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1 0\n 10 12 1 0\n 12 13 2 0\n 12 14 1 0\n 14 15 1 0\nA 6\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4432216108054027, 0.6037727113053508, 0.5867933966983492, 0.9459105810450498 ], "category_id": 1, "smiles": "*C1(CCCC)CCC(=O)C([H])C1(C)O", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 2.2973 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4418 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4418 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3856 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4179 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4179 -8.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4179 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4179 -1.1260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1809 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3617 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3617 0.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3056 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2494 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3056 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3617 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 15 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\n 12 14 1 0\n 14 15 1 0\nA 6\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6388194097048524, 0.6024309941691167, 0.7123561780890445, 0.6963511937055047 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.76088044022011, 0.5836469542618392, 0.903951975987994, 0.8519903815086618 ], "category_id": 1, "smiles": "*C12CCCCC1=CC(=O)CC2", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 0.5581 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1251 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5806 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5806 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5806 -1.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1477 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4916 -1.7559 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"C/N=C/CCC=O.[H]OC(=CC(=O)O)CC(=O)O.[I-]", "molfile": "\n RDKit 2D\n\n 14 11 0 0 0 0 0 0 0 0999 V2000\n 7.5831 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1885 -5.8504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8810 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4865 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4865 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8810 -8.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8763 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2709 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5783 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5783 -0.4961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2709 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8858 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2803 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8952 -4.1181 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 12 1 0\n 10 11 1 0\n 12 13 1 0\nM CHG 1 14 -1\nA 6\nCHO\nA 7\nHO2C\nA 13\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6228114057028514, 0.0, 0.8564282141070535, 0.23215681915031589 ], "category_id": 1, "smiles": "C/N=C/CCC=O.[H]OC(=CC(=O)O)CC(=O)O.[I-]", "molfile": "\n RDKit 2D\n\n 14 11 0 0 0 0 0 0 0 0999 V2000\n 7.5831 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1885 -5.8504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8810 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4865 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4865 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8810 -8.2913 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8763 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2709 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5783 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5783 -0.4961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2709 0.2913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8858 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2803 -2.0709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8952 -4.1181 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 9 12 1 0\n 10 11 1 0\n 12 13 1 0\nM CHG 1 14 -1\nA 6\nCHO\nA 7\nHO2C\nA 13\nCO2H\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.03601800900450225, 0.2606961917172578, 0.2706353176588294, 0.4955971813067027 ], "category_id": 1, "smiles": "[H]C(=O)CCC([NH2+]C)C(C(=O)O)C(=O)CC(=O)O.[I-]", "molfile": "\n RDKit 2D\n\n 15 13 0 0 0 0 0 0 0 0999 V2000\n 6.7592 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3727 -4.3543 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 4.0728 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0728 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6863 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3727 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7592 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0590 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3727 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6863 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6863 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0728 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6326 -6.7165 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5529 -8.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3987 -3.8031 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 10 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 9 2 0\n 7 8 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 2 0\nM CHG 2 2 1 15 -1\nA 5\nHO2C\nA 8\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.03601800900450225, 0.2606961917172578, 0.2706353176588294, 0.4955971813067027 ], "category_id": 1, "smiles": "[H]C(=O)CCC([NH2+]C)C(C(=O)O)C(=O)CC(=O)O.[I-]", "molfile": "\n RDKit 2D\n\n 15 13 0 0 0 0 0 0 0 0999 V2000\n 6.7592 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3727 -4.3543 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 4.0728 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0728 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6863 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3727 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7592 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0590 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3727 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6863 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6863 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0728 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6326 -6.7165 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5529 -8.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3987 -3.8031 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 10 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 9 2 0\n 7 8 1 0\n 10 11 1 0\n 11 12 1 0\n 12 13 1 0\n 12 14 2 0\nM CHG 2 2 1 15 -1\nA 5\nHO2C\nA 8\nCO2H\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.327663831915958, 0.25026834404856746, 0.5622811405702851, 0.4670578087397608 ], "category_id": 1, "smiles": "C[NH+]1C(O)CCC1C(C(=O)O)C(=O)CC(=O)O", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 7.4871 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7089 -5.2205 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 5.0538 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8961 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2756 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9012 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3987 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3987 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9012 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8961 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3935 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8909 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8961 0.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 13 2 0\n 11 12 1 0\nM CHG 1 2 1\nA 9\nHO2C\nA 12\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.327663831915958, 0.25026834404856746, 0.5622811405702851, 0.4670578087397608 ], "category_id": 1, "smiles": "C[NH+]1C(O)CCC1C(C(=O)O)C(=O)CC(=O)O", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 7.4871 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7089 -5.2205 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 5.0538 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8961 -8.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2756 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9012 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3987 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3987 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9012 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8961 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3935 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8909 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8961 0.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 13 2 0\n 11 12 1 0\nM CHG 1 2 1\nA 9\nHO2C\nA 12\nCO2H\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5797898949474737, 0.32436094590505127, 0.662831415707854, 0.36826767293111573 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6928464232116058, 0.257403187190303, 0.927463731865933, 0.4489462838415092 ], "category_id": 1, "smiles": "[H]OC(=CC(=O)O)C(C(=O)O)C1CCC=[N+]1C", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 8.4671 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4562 -6.9528 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 5.0803 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0803 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3868 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7737 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7737 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4671 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4671 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1605 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3868 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8102 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7153 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 13 2 0\n 3 4 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 9 2 0\n 7 8 1 0\n 9 10 1 0\n 11 12 1 0\n 12 13 1 0\nM CHG 1 2 1\nA 5\nHO2C\nA 10\nCO2H\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6928464232116058, 0.257403187190303, 0.927463731865933, 0.4489462838415092 ], "category_id": 1, "smiles": "[H]OC(=CC(=O)O)C(C(=O)O)C1CCC=[N+]1C", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 8.4671 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4562 -6.9528 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 5.0803 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0803 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3868 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7737 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7737 -0.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4671 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4671 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1605 -2.7008 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3868 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8102 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7153 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 13 2 0\n 3 4 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 9 2 0\n 7 8 1 0\n 9 10 1 0\n 11 12 1 0\n 12 13 1 0\nM CHG 1 2 1\nA 5\nHO2C\nA 10\nCO2H\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.1775887943971986, 0.5559689309675414, 0.3441720860430215, 0.7447678571796186 ], "category_id": 1, "smiles": "CN1C2CCC1C(C(=O)O)C(=O)C2", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 0.6900 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4567 -1.3622 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1467 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1401 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4501 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2101 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4434 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6067 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9200 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3833 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6668 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 1 0\n 3 4 1 0\n 3 10 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\nA 5\nHO2C\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1775887943971986, 0.5559689309675414, 0.3441720860430215, 0.7447678571796186 ], "category_id": 1, "smiles": "CN1C2CCC1C(C(=O)O)C(=O)C2", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 0.6900 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4567 -1.3622 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1467 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1401 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4501 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2101 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4434 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6067 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9200 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3833 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6668 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 1 0\n 3 4 1 0\n 3 10 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 1 0\nA 5\nHO2C\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.36868434217108553, 0.6207313533309865, 0.545272636318159, 0.6591497394787929 ], "category_id": 2, "text": [ "decarboxylation" ] } ], "products": [ { "category": "[Txt]", "bbox": [ 0.5797898949474737, 0.6404893804927154, 0.6528264132066033, 0.68439610751878 ], "category_id": 2, "text": [ "COz" ] }, { "category": "[Mol]", "bbox": [ 0.7078539269634817, 0.5570665991431929, 0.8699349674837419, 0.7464143594430961 ], "category_id": 1, "smiles": "CN1C2C=C(O)C(C(=O)O)C1CC2", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 0.6670 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4822 -1.4409 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1491 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1501 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4090 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2251 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6332 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5947 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5938 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9634 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4447 -6.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 1 0\n 3 4 1 0\n 3 11 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nA 5\nHO2C\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.17858929464732365, 0.7612328798143927, 0.327663831915958, 0.9769246763299345 ], "category_id": 1, "smiles": "" } ], "conditions": [], "products": [ { "category": "[Txt]", "bbox": [ 0.40070035017508754, 0.8463021634273927, 0.47123561780890444, 0.890757724541283 ], "category_id": 2, "text": [ "COzt" ] }, { "category": "[Mol]", "bbox": [ 0.5052526263131566, 0.7683677229561283, 0.6653326663331666, 0.9604596536951603 ], "category_id": 1, "smiles": "CI.CN1C2C=C(O)CC1CC2", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 0.5771 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2985 -1.3622 0.0000 N 0 0 0 0 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2.9416 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 8 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\nM END\n" } ] } ], "Rupe rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.026013006503251626, 0.15555426899706634, 0.15957978989494748, 0.3955178312483547 ], "category_id": 1, "smiles": "C#CC1(O)CCCCC1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 12.6327 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3692 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2111 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0532 -0.4961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2111 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3687 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6316 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6316 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3687 -1.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 3 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 9 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.1905952976488244, 0.19293552743822182, 0.23611805902951477, 0.29302083229679937 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.26113056528264134, 0.10852623418399977, 0.39469734867433715, 0.4063704546667547 ], "category_id": 1, "smiles": "C#CC1(O)CCCCC1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 10.1948 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5611 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0124 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7770 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0124 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8036 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5097 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5097 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8036 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 3 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 9 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.26113056528264134, 0.10852623418399977, 0.39469734867433715, 0.4063704546667547 ], "category_id": 1, "smiles": "C#CC1(O)CCCCC1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 10.1948 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5611 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0124 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7770 -2.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0124 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8036 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5097 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5097 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8036 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 3 0\n 2 3 1 0\n 3 4 1 0\n 3 5 1 0\n 3 9 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4332166083041521, 0.19655306857768848, 0.5132566283141571, 0.2833740559248883 ], "category_id": 2, "text": [ "HzO" ] }, { "category": "[Txt]", "bbox": [ 0.4122061030515258, 0.32196116141253267, 0.5392696348174087, 0.3967236782948437 ], "category_id": 2, "text": [ "dehydration" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5577788894447223, 0.15796596309004413, 0.6863431715857929, 0.4172230780851547 ], "category_id": 1, "smiles": "[H]C1CCCCC1C#C", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 11.0745 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3528 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8188 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8188 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3528 -7.7402 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1910 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5631 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5631 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1910 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 3 0\n 2 3 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5577788894447223, 0.15796596309004413, 0.6863431715857929, 0.4172230780851547 ], "category_id": 1, "smiles": "[H]C1CCCCC1C#C", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 11.0745 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3528 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8188 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8188 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3528 -7.7402 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1910 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5631 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5631 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1910 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 3 0\n 2 3 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7003501750875438, 0.18208290401982186, 0.7693846923461731, 0.28819744411084386 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.783391695847924, 0.07355666983582207, 0.9429714857428715, 0.3991353723878214 ], "category_id": 1, 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0\n 6.1149 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9278 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6184 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6184 -6.9528 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4312 -2.2283 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3021 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6115 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 9 1 0\n 5 6 2 3\n 6 7 1 0\n 6 8 1 0\n 9 10 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.19409704852426213, 0.6535690991969765, 0.35267633816908456, 0.8983560496342203 ], "category_id": 1, "smiles": "[H]C([H])=CC1=CCCCC1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 0.6115 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3021 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1149 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1149 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9278 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6184 -3.7244 0.0000 C 0 0 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0 0\n 12.7975 -3.0157 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0367 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5423 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 5 7 2 3\n 7 8 1 0\n 7 9 1 0\n 10 11 1 0\nM CHG 1 6 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.42021010505252626, 0.594482593919021, 0.5792896448224112, 0.8742391087044427 ], "category_id": 1, "smiles": "[H]C([H])=C([O-])C1=CCCCC1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 0.5423 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0367 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4227 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4227 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9171 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9171 -0.2598 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 10.4115 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4115 -7.1890 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.7975 -3.0157 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0367 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5423 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 5 7 2 3\n 7 8 1 0\n 7 9 1 0\n 10 11 1 0\nM CHG 1 6 -1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.615807903951976, 0.6993912869635541, 0.7818909454727364, 0.7717421097528873 ], "category_id": 2, "text": [ "tautomerization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.8244122061030515, 0.6137761466628431, 0.9499749874937469, 0.8947385084947537 ], "category_id": 1, "smiles": "CC(=O)C1=CCCCC1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 10.2399 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7857 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3315 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9620 -2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5924 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5924 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9620 -8.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3315 -7.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7857 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 2 0\n 3 4 1 0\n 3 8 2 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nM END\n" } ] } ], "Saegusa oxidation.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.11155577788894447, 0.04754710101529638, 0.2786393196598299, 0.08335417708854427 ], "category_id": 1, "smiles": "*OC(C)=O", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 12.2638 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 21.8996 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nA 1\nAcO\nA 2\nPd(I)\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.408704352176088, 0.021719046142789702, 0.46973486743371684, 0.06574413967547153 ], "category_id": 1, "smiles": "*.[Ga]", "molfile": "\n RDKit 2D\n\n 2 0 0 0 0 0 0 0 0 0999 V2000\n 4.4783 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3071 -1.8346 0.0000 Ga 0 0 0 0 0 15 0 0 0 0 0 0\nA 1\nAcO\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05252626313156578, 0.08452817958274911, 0.2051025512756378, 0.22893048636994554 ], "category_id": 1, "smiles": "CC1C=C(O[Si](C)(C)C)CCC1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 4.3754 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5146 -1.0472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5146 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4592 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4592 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4038 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5146 -7.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4727 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4727 -4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 3 9 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 8 9 1 0\nA 1\nMe3Si\nA 6\nMe\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.45822911455727866, 0.07572316087621275, 0.689344672336168, 0.221299470157614 ], "category_id": 1, "smiles": "*C1C(=O[Si](C)(C)C)CCCC1C.CC(=O)OOC(C)=O", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 2.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.0490 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 3\n 5 8 1 0\n 6 7 1 0\n 8 9 1 0\n 9 10 1 0\n 11 12 1 0\nA 1\nMe\nA 4\nPd((I))\nA 7\nMe3Si\nA 11\nOAc\nA 12\nOAc\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45822911455727866, 0.07572316087621275, 0.689344672336168, 0.221299470157614 ], "category_id": 1, "smiles": "*C1C(=O[Si](C)(C)C)CCCC1C.CC(=O)OOC(C)=O", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 3.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 2.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 3.0490 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 2 3\n 5 8 1 0\n 6 7 1 0\n 8 9 1 0\n 9 10 1 0\n 11 12 1 0\nA 1\nMe\nA 4\nPd((I))\nA 7\nMe3Si\nA 11\nOAc\nA 12\nOAc\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.776888444222111, 0.081593173347237, 0.9164582291145573, 0.16612135292998612 ], "category_id": 1, "smiles": "CC(=O)O[Si](C)(C)C", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 6.7042 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3521 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9039 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7042 -0.7323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nA 2\nMe\nA 3\nOSiMe3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0720360180090045, 0.2576935474779643, 0.2511255627813907, 0.3979868455354437 ], "category_id": 1, "smiles": "*C1C(=O)CCCC1([H])C.CC(=O)OI", "molfile": "\n RDKit 2D\n\n 12 11 0 0 0 0 0 0 0 0999 V2000\n 5.7874 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6063 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8504 -5.8504 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4803 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4724 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4724 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4803 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6063 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6142 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4803 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0472 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4488 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 8 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 10 2 0\n 8 9 1 0\n 11 12 1 0\nA 1\nMe\nA 9\nPd(I)\nA 11\nOAc\nA 12\n(I)\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2691345672836418, 0.2858696073388807, 0.36418209104552274, 0.3210896821650262 ], "category_id": 2, "text": [ "B-hydride" ] }, { "category": "[Txt]", "bbox": [ 0.2666333166583292, 0.33693871583679164, 0.3691845922961481, 0.3657017769448104 ], "category_id": 2, "text": [ "elimination" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3966983491745873, 0.255932543736657, 0.5672836418209104, 0.3827248131107807 ], "category_id": 1, "smiles": "CC1=CC(=O)CCC1.[H][Pd-](C)(C)OC(C)=O", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 4.9416 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1654 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7179 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4942 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4942 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7179 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7179 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9416 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8298 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7714 -4.5118 0.0000 Pd 0 0 0 0 0 4 0 0 0 0 0 0\n 8.2772 -1.2047 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.3541 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8298 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 2 0\n 6 8 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 1 0\nM CHG 1 10 -1\nM RAD 1 10 2\nA 2\nMe\nA 12\nOAc\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3966983491745873, 0.255932543736657, 0.5672836418209104, 0.3827248131107807 ], "category_id": 1, "smiles": "CC1=CC(=O)CCC1.[H][Pd-](C)(C)OC(C)=O", "molfile": "\n RDKit 2D\n\n 13 12 0 0 0 0 0 0 0 0999 V2000\n 4.9416 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1654 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7179 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4942 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4942 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7179 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7179 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9416 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8298 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7714 -4.5118 0.0000 Pd 0 0 0 0 0 4 0 0 0 0 0 0\n 8.2772 -1.2047 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.3541 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8298 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 8 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 2 0\n 6 8 1 0\n 9 10 1 0\n 10 11 1 0\n 10 12 1 0\n 10 13 1 0\nM CHG 1 10 -1\nM RAD 1 10 2\nA 2\nMe\nA 12\nOAc\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.632816408204102, 0.24595352253591585, 0.7343671835917959, 0.37391979440424433 ], "category_id": 1, "smiles": "CC1=CC(=O)CCC1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 7.3356 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9149 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9149 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6408 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6408 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5135 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5135 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6408 -8.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 8 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\nA 1\nMe\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.7543771885942971, 0.2999576372693389, 0.8124062031015508, 0.33752571708389406 ], "category_id": 2, "text": [ "Pd(o)" ] }, { "category": "[Txt]", "bbox": [ 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5 1 0\n 4 6 1 0\n 5 6 1 0\nA 2\nt-Bu\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.8139853355718056, 0.4227113556778389, 0.9354266961208251, 0.560280140070035 ], "category_id": 1, "smiles": "CC(C)(C)O12O[Ti]13OO23", "molfile": "\n RDKit 2D\n\n 6 8 0 0 0 0 0 0 0 0999 V2000\n -0.4330 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 2.2500 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -0.7500 0.0000 Ti 0 0 0 0 0 4 0 0 0 0 0 0\n -1.7321 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 6 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 5 6 1 0\nA 2\nt-Bu\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7401358595622667, 0.7318659329664833, 0.8703297506013056, 0.8699349674837419 ], "category_id": 1, "smiles": "CC(C)(C)O[Ti+]123C[C+]1(CO2)CO3.[I-]", "molfile": "\n RDKit 2D\n\n 10 11 0 0 0 0 0 0 0 0999 V2000\n 4.6822 -5.4567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6822 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1214 -3.3307 0.0000 Ti 0 0 0 0 0 5 0 0 0 0 0 0\n 5.8357 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1429 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5822 -0.8898 0.0000 C 0 0 0 0 0 4 0 0 0 0 0 0\n 4.6822 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7822 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1429 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9500 -5.8504 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 6 1 0\n 3 8 1 0\n 3 9 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 9 1 0\n 7 8 1 0\nM CHG 3 3 1 6 1 10 -1\nM RAD 2 3 2 6 2\nA 2\nt-Bu\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7401358595622667, 0.7318659329664833, 0.8703297506013056, 0.8699349674837419 ], "category_id": 1, "smiles": "CC(C)(C)O[Ti+]123C[C+]1(CO2)CO3.[I-]", "molfile": "\n RDKit 2D\n\n 10 11 0 0 0 0 0 0 0 0999 V2000\n 4.6822 -5.4567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6822 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1214 -3.3307 0.0000 Ti 0 0 0 0 0 5 0 0 0 0 0 0\n 5.8357 -3.3307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1429 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5822 -0.8898 0.0000 C 0 0 0 0 0 4 0 0 0 0 0 0\n 4.6822 0.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7822 -0.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1429 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9500 -5.8504 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 6 1 0\n 3 8 1 0\n 3 9 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 9 1 0\n 7 8 1 0\nM CHG 3 3 1 6 1 10 -1\nM RAD 2 3 2 6 2\nA 2\nt-Bu\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.2073255659823349, 0.822911455727864, 0.3336902249319902, 0.9639819909954978 ], "category_id": 1, "smiles": "CC(C)(C)O[Ti+]1OCC2CO21", "molfile": "\n RDKit 2D\n\n 8 9 0 0 0 0 0 0 0 0999 V2000\n -2.3231 -2.6401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7903 -2.9520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8596 -1.2135 0.0000 Ti 0 0 0 0 0 3 0 0 0 0 0 0\n -2.7413 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8596 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 8 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 7 8 1 0\nM CHG 1 3 1\nA 2\nt-Bu\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2073255659823349, 0.822911455727864, 0.3336902249319902, 0.9639819909954978 ], "category_id": 1, "smiles": "CC(C)(C)O[Ti+]1OCC2CO21", "molfile": "\n RDKit 2D\n\n 8 9 0 0 0 0 0 0 0 0999 V2000\n -2.3231 -2.6401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7903 -2.9520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8596 -1.2135 0.0000 Ti 0 0 0 0 0 3 0 0 0 0 0 0\n -2.7413 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8596 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4330 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0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2691345672836418, 0.03431736049659542, 0.42471235617808906, 0.1884090380205239 ], "category_id": 1, "smiles": "[H]C(O)C([OH2])CO", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2990 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 2.2500 0.0000 O 0 0 0 0 0 3 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 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-0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6446 -3.1732 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 11.7774 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7774 -7.2677 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2609 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\nM CHG 1 2 -1\nA 5\nCHO\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3106553276638319, 0.3364447107509355, 0.42971485742871435, 0.380855412570059 ], "category_id": 2, "text": [ "dehydration" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.45372686343171587, 0.26108109554272596, 0.5317658829414708, 0.4259390038106844 ], "category_id": 1, "smiles": "[H].[H]C(=O)C=C", "molfile": "\n RDKit 2D\n\n 6 4 0 0 0 0 0 0 0 0999 V2000\n 0.5017 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5017 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6086 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7155 -6.0079 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6086 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0634 -0.8110 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 3 5 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.48874437218609307, 0.38220119141306275, 0.6038019009504753, 0.4925550565393696 ], "category_id": 1, "smiles": "Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 13.4304 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3226 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1037 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1037 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1068 -7.1102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3226 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4304 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45372686343171587, 0.26108109554272596, 0.5317658829414708, 0.4259390038106844 ], "category_id": 1, "smiles": "[H].[H]C(=O)C=C", "molfile": "\n RDKit 2D\n\n 6 4 0 0 0 0 0 0 0 0999 V2000\n 0.5017 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5017 -5.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6086 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7155 -6.0079 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6086 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0634 -0.8110 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 3 5 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.48874437218609307, 0.38220119141306275, 0.6038019009504753, 0.4925550565393696 ], "category_id": 1, "smiles": "Nc1ccccc1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 13.4304 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3226 -0.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1037 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1037 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1068 -7.1102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3226 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4304 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 7 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6148074037018509, 0.3350989319079318, 0.7163581790895448, 0.37883674430555336 ], "category_id": 2, "text": [ "conjugate" ] }, { "category": "[Txt]", "bbox": [ 0.6253126563281641, 0.39633186926460207, 0.7078539269634817, 0.43199500860420115 ], "category_id": 2, "text": [ "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7433716858429215, 0.27992199934477835, 0.9144572286143071, 0.4764057104233247 ], "category_id": 1, "smiles": "[H]O/C=C/CNc1ccccc1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 0.3682 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3682 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2090 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9578 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7065 -6.8740 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4553 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4553 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2041 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2041 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9529 0.1339 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9578 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2090 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 12 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 11 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 11 12 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7433716858429215, 0.27992199934477835, 0.9144572286143071, 0.4764057104233247 ], "category_id": 1, "smiles": "[H]O/C=C/CNc1ccccc1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 0.3682 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3682 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2090 -6.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9578 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7065 -6.8740 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4553 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4553 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2041 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2041 -0.8898 0.0000 O 0 0 0 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2477 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2710 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4755 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3624 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3857 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 10 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 2 0\n 10 11 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.19959979989994997, 0.5773391236486054, 0.3136568284142071, 0.7556548203466011 ], "category_id": 1, "smiles": "O=CCCNc1ccccc1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 0.4771 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4771 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3857 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3624 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2710 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2477 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2477 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 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"\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 8.2477 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2710 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2710 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3624 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3624 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3624 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3857 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4771 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4771 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3857 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2710 -6.6378 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.2477 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 12 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 10 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 1 0\nM CHG 1 11 1\nA 4\nY\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6708354177088545, 0.5746475659625978, 0.7853926963481741, 0.7529632626605938 ], "category_id": 1, "smiles": "[H]*12ccccc1=[NH+]CCC2O", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 8.2477 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2710 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2710 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3624 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3624 -1.1260 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3624 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3857 -6.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4771 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4771 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3857 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2710 -6.6378 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.2477 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 12 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 10 1 0\n 6 7 1 0\n 6 11 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\n 11 12 1 0\nM CHG 1 11 1\nA 4\nY\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8314157078539269, 0.5672457823260773, 0.9444722361180591, 0.7469072578670769 ], "category_id": 1, "smiles": "OC1CCNc2ccccc21", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 8.0455 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1172 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1172 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1890 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3272 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4654 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4654 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3272 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1890 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1172 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0455 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.8314157078539269, 0.5672457823260773, 0.9444722361180591, 0.7469072578670769 ], "category_id": 1, "smiles": "OC1CCNc2ccccc21", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 8.0455 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1172 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1172 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1890 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3272 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4654 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4654 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3272 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1890 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1172 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0455 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 11 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.12356178089044523, 0.8747562479524323, 0.1645822911455728, 0.9218585074575633 ], "category_id": 2, "text": [ "H" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.18509254627313657, 0.787953512578691, 0.32866433216608304, 0.9931847861367616 ], "category_id": 1, "smiles": "[H]C1CNc2ccccc2C1O", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 6.9690 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6001 -3.2520 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -1.2047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7069 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0017 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3707 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3707 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0017 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7069 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -7.1890 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9690 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 12 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 10 2 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.18509254627313657, 0.787953512578691, 0.32866433216608304, 0.9931847861367616 ], "category_id": 1, "smiles": "[H]C1CNc2ccccc2C1O", "molfile": "\n RDKit 2D\n\n 12 13 0 0 0 0 0 0 0 0999 V2000\n 6.9690 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6001 -3.2520 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -1.2047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7069 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0017 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3707 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3707 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0017 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7069 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -7.1890 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9690 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 12 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 10 2 0\n 6 7 2 0\n 7 8 1 0\n 8 9 2 0\n 9 10 1 0\n 10 11 1 0\n 11 12 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3371685842921461, 0.866008685472908, 0.4547273636818409, 0.9077278296060239 ], "category_id": 2, "text": [ "dehydration" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.471735867933967, 0.8498593393568631, 0.5862931465732867, 0.9783812188637205 ], "category_id": 1, "smiles": "C1=Cc2ccccc2NC1", "molfile": "\n RDKit 2D\n\n 10 11 0 0 0 0 0 0 0 0999 V2000\n 11.4173 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6581 -5.8504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9941 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3301 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6660 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6660 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3301 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9941 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6581 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4173 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 2 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.471735867933967, 0.8498593393568631, 0.5862931465732867, 0.9783812188637205 ], "category_id": 1, "smiles": "C1=Cc2ccccc2NC1", "molfile": "\n RDKit 2D\n\n 10 11 0 0 0 0 0 0 0 0999 V2000\n 11.4173 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6581 -5.8504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9941 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3301 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6660 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6660 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3301 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9941 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6581 0.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4173 -1.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\n 8 9 1 0\n 9 10 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6133066533266633, 0.8538966758858744, 0.7363681840920461, 0.8949429305974884 ], "category_id": 2, "text": [ "oxidation by" ] }, { "category": "[Txt]", "bbox": [ 0.6133066533266633, 0.9184940603500539, 0.7383691845922962, 0.9622318727476755 ], "category_id": 2, "text": [ "H2", "PhNO2" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7613806903451726, 0.860625570100893, 0.8734367183591796, 0.9669420986981886 ], "category_id": 1, "smiles": "c1ccc2ncccc2c1", "molfile": "\n RDKit 2D\n\n 10 11 0 0 0 0 0 0 0 0999 V2000\n 0.7785 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7785 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0039 -7.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1181 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3435 -7.4252 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4577 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.4577 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3435 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1181 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0039 0.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 10 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 9 1 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\nM END\n" } ] } ], "Smiles rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.05152576288144072, 0.08967759741939936, 0.3216608304152076, 0.49552621138155284 ], "category_id": 1, "smiles": "O=[N+]([O-])c1ccccc1Sc1ccccc1O", "molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 14.3839 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0873 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7907 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7907 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3733 -2.6220 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1975 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1975 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4941 -7.8189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9010 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6044 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6044 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9010 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0873 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 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"molfile": "\n RDKit 2D\n\n 15 16 0 0 0 0 0 0 0 0999 V2000\n 14.2588 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9822 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7056 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7056 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3091 -2.6220 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1523 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1523 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3091 -7.8189 0.0000 Os 0 0 0 0 0 1 0 0 0 0 0 0\n 2.8757 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5991 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5991 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8757 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9822 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9822 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.2588 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 13 1 0\n 5 6 1 0\n 6 7 2 0\n 6 12 1 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 13 14 1 0\n 13 15 2 0\nA 14\nNO2\nM 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0.04862326996831749, 0.753376688344172, 0.20529825097734053 ], "category_id": 1, "smiles": "[1*]C1=CN(Cc2ccccc2)=CS1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 1.2760 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\nM ISO 1 5 1\nA 2\nBn\nA 5\nR1\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7648824412206103, 0.12811845737683658, 0.8424212106053026, 0.2516061271376429 ], "category_id": 1, "smiles": "*C([H])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 4.2919 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2189 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4562 -0.6535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0472 -2.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nA 2\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.16008004002001, 0.29251141774591005, 0.3401700850425213, 0.4846891038111648 ], "category_id": 1, "smiles": "*C([H])(O)c1sc([1*])c[n+]1Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 7.2078 -1.9921 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.8095 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8052 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7755 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3729 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7204 -6.1654 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8942 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2968 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8688 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6994 -6.1654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2417 -3.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM CHG 1 1 1\nM ISO 1 5 1\nA 2\nBn\nA 5\nR1\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.16008004002001, 0.29251141774591005, 0.3401700850425213, 0.4846891038111648 ], "category_id": 1, "smiles": "*C([H])(O)c1sc([1*])c[n+]1Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 7.2078 -1.9921 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.8095 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8052 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7755 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3729 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7204 -6.1654 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8942 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2968 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8688 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6994 -6.1654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2417 -3.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM CHG 1 1 1\nM ISO 1 5 1\nA 2\nBn\nA 5\nR1\nA 9\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4382191095547774, 0.29559860948993016, 0.6183091545772886, 0.48623269968317495 ], "category_id": 1, "smiles": "*C(O)c1sc([1*])c[n+]1Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 7.3222 -2.0709 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.8095 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6908 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7755 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2585 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8348 -6.2441 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0086 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4112 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8688 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2417 -3.7244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\nM CHG 1 1 1\nM ISO 1 5 1\nA 2\nBn\nA 5\nR1\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4382191095547774, 0.29559860948993016, 0.6183091545772886, 0.48623269968317495 ], "category_id": 1, "smiles": "*C(O)c1sc([1*])c[n+]1Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 7.3222 -2.0709 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.8095 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6908 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7755 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2585 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8348 -6.2441 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0086 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4112 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8688 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2417 -3.7244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\nM CHG 1 1 1\nM ISO 1 5 1\nA 2\nBn\nA 5\nR1\nA 9\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.16008004002001, 0.29251141774591005, 0.3401700850425213, 0.4846891038111648 ], "category_id": 1, "smiles": "*C([H])(O)c1sc([1*])c[n+]1Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 7.2078 -1.9921 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.8095 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8052 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7755 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3729 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7204 -6.1654 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8942 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2968 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8688 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.6994 -6.1654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2417 -3.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\nM CHG 1 1 1\nM ISO 1 5 1\nA 2\nBn\nA 5\nR1\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4382191095547774, 0.29559860948993016, 0.6183091545772886, 0.48623269968317495 ], "category_id": 1, "smiles": "*C(O)c1sc([1*])c[n+]1Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 7.3222 -2.0709 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.8095 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6908 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7755 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2585 -5.2205 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8348 -6.2441 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0086 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.4112 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8688 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2417 -3.7244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\nM CHG 1 1 1\nM ISO 1 5 1\nA 2\nBn\nA 5\nR1\nA 9\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6298149074537268, 0.41754268337872646, 0.7313656828414207, 0.5217354047394067 ], "category_id": 1, "smiles": "C=CC(C)=O", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 1.5354 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0236 0.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0394 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1732 0.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0394 -6.9528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 3 5 2 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7648824412206103, 0.12811845737683658, 0.8424212106053026, 0.2516061271376429 ], "category_id": 1, "smiles": "*C([H])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 4.2919 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2189 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4562 -0.6535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0472 -2.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nA 2\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6298149074537268, 0.41754268337872646, 0.7313656828414207, 0.5217354047394067 ], "category_id": 1, "smiles": "C=CC(C)=O", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 1.5354 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0236 0.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0394 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.1732 0.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0394 -6.9528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 3 5 2 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7393696848424212, 0.32647052693013173, 0.8289144572286143, 0.37277840309043414 ], "category_id": 2, "text": [ "Michael" ] }, { "category": "[Txt]", "bbox": [ 0.7418709354677339, 0.4005631287866156, 0.8274137068534267, 0.4414684193948827 ], "category_id": 2, "text": [ "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.08454227113556778, 0.5580099077316436, 0.33016508254127064, 0.7625363607729791 ], "category_id": 1, "smiles": "*C(O)(C/C=C(/C)O)c1sc([1*])c[n+]1Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 6.8687 -1.9134 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.4762 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5304 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6535 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1691 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5534 -5.6929 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5994 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9376 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2069 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6683 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2759 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0296 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.3679 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9524 -6.8740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1216 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\n 13 15 1 0\nM CHG 1 1 1\nM ISO 1 5 1\nA 2\nBn\nA 5\nR1\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.08454227113556778, 0.5580099077316436, 0.33016508254127064, 0.7625363607729791 ], "category_id": 1, "smiles": "*C(O)(C/C=C(/C)O)c1sc([1*])c[n+]1Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 6.8687 -1.9134 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.4762 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5304 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6535 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1691 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5534 -5.6929 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5994 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9376 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2069 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6683 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2759 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0296 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.3679 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9524 -6.8740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1216 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\n 13 15 1 0\nM CHG 1 1 1\nM ISO 1 5 1\nA 2\nBn\nA 5\nR1\nA 9\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.3776888444222111, 0.6359614992681527, 0.5397698849424712, 0.68149757749245 ], "category_id": 2, "text": [ "tautomerization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5797898949474737, 0.582707441683805, 0.8234117058529264, 0.7710261380690346 ], "category_id": 1, "smiles": "*C(O)(CCC(C)=O)C1=N(Cc2ccccc2)C=C([1*])S1", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 5.3741 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0750 -3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0750 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2760 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 8 13 2 0\n 9 10 1 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\n 13 14 1 0\nM ISO 1 11 1\nA 6\nR\nA 11\nR1\nA 14\nBn\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5797898949474737, 0.582707441683805, 0.8234117058529264, 0.7710261380690346 ], "category_id": 1, "smiles": "*C(O)(CCC(C)=O)C1=N(Cc2ccccc2)C=C([1*])S1", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 5.3741 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0750 -3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0750 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2760 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7760 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 8 13 2 0\n 9 10 1 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\n 13 14 1 0\nM ISO 1 11 1\nA 6\nR\nA 11\nR1\nA 14\nBn\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.08454227113556778, 0.5580099077316436, 0.33016508254127064, 0.7625363607729791 ], "category_id": 1, "smiles": "*C(O)(C/C=C(/C)O)c1sc([1*])c[n+]1Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 6.8687 -1.9134 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 8.4762 -0.0236 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5304 -1.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6535 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1691 -4.8268 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5534 -5.6929 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5994 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9376 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2069 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6683 -2.7008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2759 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0296 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.3679 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.9524 -6.8740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 18.1216 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 7 2 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 8 11 1 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\n 13 15 1 0\nM CHG 1 1 1\nM ISO 1 5 1\nA 2\nBn\nA 5\nR1\nA 9\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.061030515257628815, 0.8034416513812462, 0.22011005502751377, 0.9662910158783096 ], "category_id": 1, "smiles": "*C(=O)CCC(C)=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 14.5276 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8110 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0945 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4961 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8976 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1811 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8976 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8110 -7.6614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\nA 6\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.2766383191595798, 0.8080724389972765, 0.5302651325662832, 0.9624320261982845 ], "category_id": 1, "smiles": "OCCCC1=CN(Cc2ccccc2)=CS1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 2.7760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5260 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.0890 3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.3025 4.0051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1458 5.4969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 11 2 0\n 4 5 2 0\n 5 6 1 0\n 5 10 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 10 11 1 0\nA 2\nPh\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5852926463231616, 0.7957236720211959, 0.6458229114557279, 0.8721316676856947 ], "category_id": 2, "text": [ "NH4" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7018509254627313, 0.8103878328052917, 0.9544772386193097, 0.9616602282622793 ], "category_id": 1, "smiles": "OCCCC1=CN(Cc2ccccc2)=CS1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 2.7760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5260 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.0890 3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.3025 4.0051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1458 5.4969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 11 2 0\n 4 5 2 0\n 5 6 1 0\n 5 10 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 10 11 1 0\nA 2\nPh\nM 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"[Mol]", "bbox": [ 0.061030515257628815, 0.8034416513812462, 0.22011005502751377, 0.9662910158783096 ], "category_id": 1, "smiles": "*C(=O)CCC(C)=O", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 14.5276 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8110 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0945 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.4961 -4.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8976 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1811 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8976 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8110 -7.6614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 8 2 0\n 3 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\nA 6\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.2766383191595798, 0.8080724389972765, 0.5302651325662832, 0.9624320261982845 ], "category_id": 1, "smiles": "OCCCC1=CN(Cc2ccccc2)=CS1", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 2.7760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5260 -1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.0890 3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.3025 4.0051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.1458 5.4969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 11 2 0\n 4 5 2 0\n 5 6 1 0\n 5 10 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 10 11 1 0\nA 2\nPh\nM END\n" } ] } ], "Stille coupling.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0415207603801901, 0.266445317691243, 0.12606303151575787, 0.38310515949119267 ], "category_id": 1, "smiles": "**", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.6917 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 16.0509 -4.3543 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\nA 1\nR\nA 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"isomerization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.021010505252626314, 0.6913175810367387, 0.1950975487743872, 0.8497445266909912 ], "category_id": 1, "smiles": "*[SnH]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.5665 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.2469 -3.9606 0.0000 Sn 0 0 0 0 0 2 0 0 0 0 0 0\n 1 2 1 0\nM RAD 1 2 3\nA 1\nX\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.28864432216108055, 0.6005821485256667, 0.4367183591795898, 0.9505616739255156 ], "category_id": 1, "smiles": "*[Pd]([1*])([1*])I", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0865 -4.0394 0.0000 Pd 0 0 0 0 0 4 0 0 0 0 0 0\n 12.0779 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0779 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0836 1.0000 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\nM ISO 2 3 1 4 1\nA 1\n*\nA 3\nR1\nA 4\nR1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.021010505252626314, 0.6913175810367387, 0.1950975487743872, 0.8497445266909912 ], "category_id": 1, "smiles": "*[SnH]", "molfile": "\n RDKit 2D\n\n 2 1 0 0 0 0 0 0 0 0999 V2000\n 3.5665 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.2469 -3.9606 0.0000 Sn 0 0 0 0 0 2 0 0 0 0 0 0\n 1 2 1 0\nM RAD 1 2 3\nA 1\nX\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.28864432216108055, 0.6005821485256667, 0.4367183591795898, 0.9505616739255156 ], "category_id": 1, "smiles": "*[Pd]([1*])([1*])I", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0865 -4.0394 0.0000 Pd 0 0 0 0 0 4 0 0 0 0 0 0\n 12.0779 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0779 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0836 1.0000 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 5 1 0\nM ISO 2 3 1 4 1\nA 1\n*\nA 3\nR1\nA 4\nR1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4777388694347174, 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0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 18 2 0\n 2 3 2 0\n 3 4 1 0\n 3 15 1 0\n 4 6 1 0\n 6 8 1 0\n 8 9 1 0\n 8 13 2 0\n 9 10 2 0\n 10 11 1 0\n 11 12 2 0\n 12 13 1 0\n 13 14 1 0\n 15 16 1 0\n 15 17 2 0\n 17 18 1 0\n 4 5 1 1\n 6 7 1 6\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.23711855927963982, 0.10477542366389588, 0.3061530765382691, 0.16604240868769937 ], "category_id": 2, "text": [ "Pd(o)" ] }, { "category": "[Txt]", "bbox": [ 0.21860930465232617, 0.1935681555824517, 0.3216608304152076, 0.28768845141612087 ], "category_id": 2, "text": [ "oxidative", "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.34317158579289647, 0.029301601533123424, 0.5202601300650325, 0.32675725346028545 ], "category_id": 1, "smiles": "*c1ccccc1[C@H](O)[C@@H](O)c1ccccc1Br", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 9.0810 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1651 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1654 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8311 -6.1654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7490 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7490 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4166 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4166 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -2.3071 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0810 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0808 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 18 2 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 17 2 0\n 6 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 15 2 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 1 0\n 17 18 1 0\n 6 7 1 6\n 8 9 1 1\nA 4\nBrPd\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.34317158579289647, 0.029301601533123424, 0.5202601300650325, 0.32675725346028545 ], "category_id": 1, "smiles": "*c1ccccc1[C@H](O)[C@@H](O)c1ccccc1Br", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 9.0810 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1651 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1654 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8311 -6.1654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7490 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7490 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4166 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4166 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -2.3071 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0810 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0808 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 18 2 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 17 2 0\n 6 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 15 2 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 1 0\n 17 18 1 0\n 6 7 1 6\n 8 9 1 1\nA 4\nBrPd\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5492746373186593, 0.09589615047204028, 0.7208604302151076, 0.16249069941095715 ], "category_id": 2, "text": [ "Me3Sn", "SnMe3" ] }, { "category": "[Txt]", "bbox": [ 0.5507753876938469, 0.1873526643481528, 0.7208604302151076, 0.24506794009521407 ], "category_id": 2, "text": [ "transmetalation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7393696848424212, 0.031965383490680094, 0.9279639819909955, 0.3303089627370277 ], "category_id": 1, "smiles": "*Cc1ccccc1[C@H](O)[C@@H](O)c1ccccc1Br", "molfile": "\n RDKit 2D\n\n 19 20 0 0 0 0 0 0 0 0999 V2000\n 6.1831 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1515 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0664 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0381 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0381 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5397 -6.1654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3598 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3598 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7698 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7698 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0916 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5016 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5016 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0916 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2682 -2.3071 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8930 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7763 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8930 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0381 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 19 2 0\n 4 5 1 0\n 4 16 2 0\n 5 7 1 0\n 7 9 1 0\n 9 10 1 0\n 9 14 2 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 1 0\n 16 17 1 0\n 17 18 2 0\n 18 19 1 0\n 5 6 1 6\n 7 8 1 1\nA 2\nMe3Sn\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7393696848424212, 0.031965383490680094, 0.9279639819909955, 0.3303089627370277 ], "category_id": 1, "smiles": "*Cc1ccccc1[C@H](O)[C@@H](O)c1ccccc1Br", "molfile": "\n RDKit 2D\n\n 19 20 0 0 0 0 0 0 0 0999 V2000\n 6.1831 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1515 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0664 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0381 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0381 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5397 -6.1654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3598 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3598 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7698 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7698 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0916 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5016 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5016 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0916 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2682 -2.3071 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8930 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7763 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8930 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0381 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 19 2 0\n 4 5 1 0\n 4 16 2 0\n 5 7 1 0\n 7 9 1 0\n 9 10 1 0\n 9 14 2 0\n 10 11 2 0\n 11 12 1 0\n 12 13 2 0\n 13 14 1 0\n 14 15 1 0\n 16 17 1 0\n 17 18 2 0\n 18 19 1 0\n 5 6 1 6\n 7 8 1 1\nA 2\nMe3Sn\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.10155077538769385, 0.4537308601038203, 0.20860430215107553, 0.510558208531696 ], "category_id": 2, "text": [ "reductive" ] }, { "category": "[Txt]", "bbox": [ 0.09504752376188094, 0.5336443188305204, 0.21560780390195097, 0.5886958126200251 ], "category_id": 2, "text": [ "elimination" ] } ], "products": [ { "category": "[Txt]", "bbox": [ 0.2381190595297649, 0.4865841709136859, 0.3046523261630815, 0.5514028652142317 ], "category_id": 2, "text": [ "Pd(o)" ] }, { "category": "[Mol]", "bbox": [ 0.34667333666833416, 0.36760191014282106, 0.5237618809404703, 0.6641696347507975 ], "category_id": 1, "smiles": "*c1ccccc1[C@H](O)[C@@H](O)c1ccccc1Br", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 9.1643 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2484 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1654 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8311 -6.1654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8324 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8324 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4166 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4166 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -2.3071 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1643 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1641 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 18 2 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 17 2 0\n 6 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 15 2 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 1 0\n 17 18 1 0\n 6 7 1 6\n 8 9 1 1\nA 4\nMe3Sn\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.34667333666833416, 0.36760191014282106, 0.5237618809404703, 0.6641696347507975 ], "category_id": 1, "smiles": "*c1ccccc1[C@H](O)[C@@H](O)c1ccccc1Br", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 9.1643 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2484 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1654 0.2126 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8311 -6.1654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8324 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8324 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4166 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4166 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -2.3071 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1643 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1641 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 18 2 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 17 2 0\n 6 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 15 2 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 1 0\n 17 18 1 0\n 6 7 1 6\n 8 9 1 1\nA 4\nMe3Sn\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5682841420710355, 0.43064474980499573, 0.6398199099549775, 0.49013588019042814 ], "category_id": 2, "text": [ "Pd(o)" ] }, { "category": "[Txt]", "bbox": [ 0.5532766383191596, 0.5167736997659949, 0.6578289144572286, 0.6117819229188496 ], "category_id": 2, "text": [ "oxidative", "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7068534267133567, 0.35783470963177993, 0.8839419709854928, 0.6535145069205709 ], "category_id": 1, "smiles": "*c1ccccc1[C@H](O)[C@@H](O)c1ccccc1*", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 9.1643 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1651 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1654 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9144 -6.2441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7490 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7490 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3332 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3332 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -2.2283 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1643 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0808 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 18 2 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 17 2 0\n 6 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 15 2 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 1 0\n 17 18 1 0\n 6 7 1 6\n 8 9 1 1\nA 4\nMe3Sn\nA 16\nPdBr\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7068534267133567, 0.35783470963177993, 0.8839419709854928, 0.6535145069205709 ], "category_id": 1, "smiles": "*c1ccccc1[C@H](O)[C@@H](O)c1ccccc1*", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 9.1643 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1651 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1654 0.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9144 -6.2441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7490 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7490 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3332 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3332 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -2.2283 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1643 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0808 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 18 2 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 17 2 0\n 6 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 15 2 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 15 16 1 0\n 17 18 1 0\n 6 7 1 6\n 8 9 1 1\nA 4\nMe3Sn\nA 16\nPdBr\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.07553776888444222, 0.7867036047984045, 0.25062531265632815, 0.8488585171413937 ], "category_id": 2, "text": [ "transmetallation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.29314657328664334, 0.6979108728798489, 0.4702351175587794, 0.9980303067645674 ], "category_id": 1, "smiles": "O[C@@H](c1ccccc1)[C@@H](O)c1ccccc1[Pd]", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 0.4139 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0695 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8078 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8078 -1.2835 0.0000 Pd 0 0 0 0 0 1 0 0 0 0 0 0\n 3.8078 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4634 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4634 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1189 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7745 -6.2441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1189 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7745 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7745 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1189 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4634 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4634 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0695 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4139 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 17 2 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 16 2 0\n 6 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 15 2 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 16 17 1 0\n 6 7 1 1\n 8 9 1 6\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.29314657328664334, 0.6979108728798489, 0.4702351175587794, 0.9980303067645674 ], "category_id": 1, "smiles": "O[C@@H](c1ccccc1)[C@@H](O)c1ccccc1[Pd]", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 0.4139 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0695 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8078 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8078 -1.2835 0.0000 Pd 0 0 0 0 0 1 0 0 0 0 0 0\n 3.8078 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4634 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4634 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1189 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7745 -6.2441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1189 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7745 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7745 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1189 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4634 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4634 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0695 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4139 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 17 2 0\n 2 3 2 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 16 2 0\n 6 8 1 0\n 8 10 1 0\n 10 11 1 0\n 10 15 2 0\n 11 12 2 0\n 12 13 1 0\n 13 14 2 0\n 14 15 1 0\n 16 17 1 0\n 6 7 1 1\n 8 9 1 6\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4912456228114057, 0.7716088403722502, 0.5947973986993497, 0.8266603341617547 ], "category_id": 2, "text": [ "reductive" ] }, { "category": "[Txt]", "bbox": [ 0.4837418709354677, 0.8541860810565071, 0.6028014007003502, 0.9065737928884549 ], "category_id": 2, "text": [ "elimination" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6273136568284142, 0.6916953816455499, 0.8044022011005503, 0.9891510335727118 ], "category_id": 1, "smiles": "O[C@H]1c2ccccc2-c2ccccc2[C@@H]1O", "molfile": "\n RDKit 2D\n\n 16 18 0 0 0 0 0 0 0 0999 V2000\n 0.4166 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8324 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9144 -0.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9144 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1648 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9144 -6.2441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4986 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8324 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0828 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4166 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 16 2 3\n 2 3 2 3\n 3 4 1 0\n 3 14 1 0\n 4 5 1 0\n 4 9 2 0\n 5 6 2 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 10 12 1 0\n 12 14 1 0\n 14 15 2 3\n 15 16 1 0\n 10 11 1 6\n 12 13 1 1\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.8449224612306153, 0.8062380058204869, 0.9129564782391195, 0.8772721913553315 ], "category_id": 2, "text": [ "Pd(o)" ] } ] } ], "Still\u2013Gennari phosphonate reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0720360180090045, 0.06596188356929623, 0.37718859429714857, 0.32877876341571094 ], "category_id": 1, "smiles": "*.[H]C(C(=O)OC)P(=O)(OO)C(=O)O", "molfile": "\n RDKit 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10\nOCH3\nA 11\nOCH3\nA 13\nCF3\nA 14\nCF3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.352176088044022, 0.5988102242775174, 0.6223111555777889, 0.9739684370778898 ], "category_id": 1, "smiles": "FC(F)F.FC(F)F.[H][C@]1(Cc2ccccc2)O[P-](O)(OC)(OC)[C@@]1([H])C(=O)O", "molfile": "\n RDKit 2D\n\n 14 12 0 0 0 0 0 0 0 0999 V2000\n 1.8585 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0654 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6462 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5554 -6.0866 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5301 -3.4094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6209 -3.4094 0.0000 P 0 0 0 0 0 5 0 0 0 0 0 0\n 8.5955 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0147 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6209 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6209 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6663 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7117 -5.5354 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4287 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8479 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 5 1 0\n 3 10 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 6 10 1 0\n 10 12 1 0\n 3 2 1 1\n 3 4 1 6\n 10 11 1 1\nM CHG 1 6 -1\nM RAD 1 6 2\nA 1\nPh\nA 7\nOCH3\nA 8\nOCH3\nA 11\nCO2H\nA 13\nCF3\nA 14\nCF3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.352176088044022, 0.5988102242775174, 0.6223111555777889, 0.9739684370778898 ], "category_id": 1, "smiles": "FC(F)F.FC(F)F.[H][C@]1(Cc2ccccc2)O[P-](O)(OC)(OC)[C@@]1([H])C(=O)O", "molfile": "\n RDKit 2D\n\n 14 12 0 0 0 0 0 0 0 0999 V2000\n 1.8585 -8.1339 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0654 -7.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6462 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5554 -6.0866 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5301 -3.4094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6209 -3.4094 0.0000 P 0 0 0 0 0 5 0 0 0 0 0 0\n 8.5955 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0147 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6209 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6209 -5.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6663 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7117 -5.5354 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4287 -3.9606 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8479 -1.9134 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 5 1 0\n 3 10 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 6 10 1 0\n 10 12 1 0\n 3 2 1 1\n 3 4 1 6\n 10 11 1 1\nM CHG 1 6 -1\nM RAD 1 6 2\nA 1\nPh\nA 7\nOCH3\nA 8\nOCH3\nA 11\nCO2H\nA 13\nCF3\nA 14\nCF3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7348674337168585, 0.711151557231475, 0.9809904952476238, 0.8502899053854593 ], "category_id": 1, "smiles": "*/C=C\\Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 3.9519 -5.2992 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1619 -5.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.9847 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 18.9125 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 21.4530 -5.6142 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 4 5 1 0\nA 1\nPh\nA 5\nCO2H3\nM END\n" } ] } ], "Stobbe condensation.png": [ { "reactants": [ { "category": "[Txt]", "bbox": [ 0.03501750875437719, 0.055023582518174616, 0.10155077538769385, 0.16638083285257563 ], "category_id": 2, "text": [ "t-Buo" ] }, { "category": "[Mol]", "bbox": [ 0.11855927963981991, 0.13100852980517763, 0.24012006003001501, 0.4152970394824131 ], "category_id": 1, "smiles": "[H]C(CC(=O)OCC)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 3.1759 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6460 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1759 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9704 -2.0709 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7342 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6750 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3517 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 2 0\nA 2\nCO2Et\nA 6\nOEt\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2651325662831416, 0.1781716005350416, 0.34817408704352176, 0.2502262919278893 ], "category_id": 2, "text": [ "enolate" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3736868434217109, 0.12969844450712587, 0.4452226113056528, 0.32490115391684055 ], "category_id": 1, "smiles": "*C(*)=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 4.8351 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8351 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0836 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5865 -7.2677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nA 2\nR\nA 3\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3736868434217109, 0.12969844450712587, 0.4452226113056528, 0.32490115391684055 ], "category_id": 1, "smiles": "*C(*)=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 4.8351 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8351 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0836 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5865 -7.2677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nA 2\nR\nA 3\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2571285642821411, 0.28690868027333905, 0.3551775887943972, 0.36158354226229034 ], "category_id": 2, "text": [ "formation" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.11855927963981991, 0.13100852980517763, 0.24012006003001501, 0.4152970394824131 ], "category_id": 1, "smiles": "[H]C(CC(=O)OCC)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 3.1759 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6460 -7.3465 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1759 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9704 -2.0709 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7342 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6750 -4.7480 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3517 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 2 0\nA 2\nCO2Et\nA 6\nOEt\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45722861430715356, 0.08384545907531368, 0.5492746373186593, 0.4152970394824131 ], "category_id": 1, "smiles": "CCOC(=O)C/C=C(/O)OCC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 0.4599 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7597 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4599 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7597 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4844 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2771 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\nA 2\nCO2Et\nA 5\nOEt\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5802901450725363, 0.1781716005350416, 0.6413206603301651, 0.25546663312009643 ], "category_id": 2, "text": [ "aldol" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6688344172086043, 0.09170597086362435, 0.8129064532266133, 0.44673908663565576 ], "category_id": 1, "smiles": "*C([1*])(O)C(CC(=O)OCC)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 6.3389 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1694 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1694 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3345 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0852 -4.1181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3389 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2528 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3389 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\nM ISO 1 5 1\nA 1\nCO2Et\nA 4\nR\nA 5\nR1\nA 9\nEtO\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6688344172086043, 0.09170597086362435, 0.8129064532266133, 0.44673908663565576 ], "category_id": 1, "smiles": "*C([1*])(O)C(CC(=O)OCC)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 6.3389 -0.2598 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1694 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1694 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3345 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0852 -4.1181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3389 -4.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3380 -6.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2528 -6.6378 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3389 -8.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 7 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\nM ISO 1 5 1\nA 1\nCO2Et\nA 4\nR\nA 5\nR1\nA 9\nEtO\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.568784392196098, 0.29345910676359793, 0.6518259129564783, 0.3642037128583938 ], "category_id": 2, "text": [ "addition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.45722861430715356, 0.08384545907531368, 0.5492746373186593, 0.4152970394824131 ], "category_id": 1, "smiles": "CCOC(=O)C/C=C(/O)OCC", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 0.4599 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7597 -7.5827 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4599 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7597 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4844 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2771 -1.5197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 2 0\n 4 5 1 0\n 4 6 1 0\nA 2\nCO2Et\nA 5\nOEt\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.028514257128564282, 0.5790577017388852, 0.1745872936468234, 0.9537420969816932 ], "category_id": 1, "smiles": "*C1(*)OC(O)(OCC)CC1C(=O)OCC", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 4.9046 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1107 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8141 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8141 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0452 -0.9685 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1709 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8594 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8141 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9046 -7.0315 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 5.5479 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM RAD 1 9 2\nA 2\nCO2Et\nA 4\nR\nA 5\nR\nA 8\nEtO\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.22761380690345173, 0.6118098341901796, 0.3736868434217109, 0.9576723528758485 ], "category_id": 1, "smiles": "*C([1*])(CC(=O)OCC)OC(C)=O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 2.8082 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8082 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6164 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7572 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3694 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3001 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1429 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3001 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 6 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\nM ISO 1 3 1\nA 1\n*\nA 3\nR1\nA 5\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.22761380690345173, 0.6118098341901796, 0.3736868434217109, 0.9576723528758485 ], "category_id": 1, "smiles": "*C([1*])(CC(=O)OCC)OC(C)=O", "molfile": "\n RDKit 2D\n\n 9 8 0 0 0 0 0 0 0 0999 V2000\n 2.8082 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8082 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 -0.4173 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6164 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7572 1.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3694 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3001 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1429 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3001 -8.1339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 6 1 0\n 4 5 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\nM ISO 1 3 1\nA 1\n*\nA 3\nR1\nA 5\nCO2Et\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.36418209104552274, 0.7899814347252213, 0.439719859929965, 0.8882378320791043 ], "category_id": 2, "text": [ "eot-Bu" ] } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.45972986493246626, 0.6733838431986131, 0.5082541270635318, 0.7506788757836679 ], "category_id": 2, "text": [ "ring" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5447723861930965, 0.6380115401512152, 0.6953476738369184, 0.9065790262518293 ], "category_id": 1, "smiles": "*/C([1*])=C(/CC(O)=O)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 6.1371 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1371 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6846 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1163 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5896 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5896 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1579 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 2 0\n 3 4 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 1 6 1\nA 2\nCO2Et\nA 4\nCO2\nA 6\nR1\nA 7\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5447723861930965, 0.6380115401512152, 0.6953476738369184, 0.9065790262518293 ], "category_id": 1, "smiles": "*/C([1*])=C(/CC(O)=O)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 6.1371 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1371 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6846 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1163 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5896 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5896 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1579 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 2 0\n 3 4 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 1 6 1\nA 2\nCO2Et\nA 4\nCO2\nA 6\nR1\nA 7\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4442221110555278, 0.7899814347252213, 0.527263631815908, 0.8685865526083278 ], "category_id": 2, "text": [ "opening" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.028514257128564282, 0.5790577017388852, 0.1745872936468234, 0.9537420969816932 ], "category_id": 1, "smiles": "*C1(*)OC(O)(OCC)CC1C(=O)OCC", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 4.9046 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1107 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8141 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8141 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0452 -0.9685 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1709 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8594 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8141 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9046 -7.0315 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 5.5479 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 10 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 7 8 1 0\n 7 9 1 0\n 7 10 1 0\nM RAD 1 9 2\nA 2\nCO2Et\nA 4\nR\nA 5\nR\nA 8\nEtO\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5447723861930965, 0.6380115401512152, 0.6953476738369184, 0.9065790262518293 ], "category_id": 1, "smiles": "*/C([1*])=C(/CC(O)=O)C(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 6.1371 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1371 -0.3386 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6846 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1163 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5896 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5896 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1579 -3.2520 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 2 0\n 3 4 1 0\n 5 6 1 0\n 5 7 1 0\nM ISO 1 6 1\nA 2\nCO2Et\nA 4\nCO2\nA 6\nR1\nA 7\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7163581790895448, 0.6537325637278365, 0.759879939969985, 0.7637797287641858 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7848924462231116, 0.632771198959008, 0.951975987993997, 0.9000285997615703 ], "category_id": 1, "smiles": 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0.3489646377592941 ], "category_id": 2, "text": [ "NC" ] }, { "category": "[Mol]", "bbox": [ 0.45822911455727866, 0.11171475202195225, 0.5682841420710355, 0.3293857636935912 ], "category_id": 1, "smiles": "[1*]/C([H])=[NH+]/[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 3.6809 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9325 -7.5039 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9325 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4538 -4.3543 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 9.2942 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\n 4 5 1 0\nM CHG 1 4 1\nM ISO 2 3 1 5 2\nA 3\nR1\nA 5\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.45822911455727866, 0.11171475202195225, 0.5682841420710355, 0.3293857636935912 ], "category_id": 1, "smiles": "[1*]/C([H])=[NH+]/[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 3.6809 -4.3543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9325 -7.5039 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9325 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"category_id": 2, "text": [] } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5317658829414708, 0.6354402850776036, 0.6688344172086043, 0.9190609915347284 ], "category_id": 1, "smiles": "*O[Si](F)(F)(F)[O-]*", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 Si 0 0 0 0 0 5 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -0.7500 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 -0.7500 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 3 5 1 6\n 3 6 1 0\n 3 7 1 1\n 7 8 1 0\nM CHG 1 1 -1\nA 2\nR\nA 8\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5317658829414708, 0.6354402850776036, 0.6688344172086043, 0.9190609915347284 ], "category_id": 1, "smiles": "*O[Si](F)(F)(F)[O-]*", "molfile": 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0 0 0 0 0 0 0999 V2000\n 0.5996 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5996 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0981 -1.2835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6965 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0957 -0.3386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5948 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9939 -5.3780 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 11.3931 -7.8189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6965 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0981 -7.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 9 1 0\n 6 7 1 0\n 7 8 3 0\n 9 10 1 0\nM CHG 1 7 1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.24362181090545273, 0.8624451913713636, 0.40670335167583793, 0.9736754161797414 ], "category_id": 1, "smiles": "N#[N+]=CC1(O)CCCCC1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6491 0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.0586 -0.4512 0.0000 N 0 0 0 0 0 5 0 0 0 0 0 0\n -5.2077 -1.4153 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 9 1 0\n 6 7 2 0\n 7 8 3 0\n 9 10 1 0\nM CHG 1 7 1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.24362181090545273, 0.8624451913713636, 0.40670335167583793, 0.9736754161797414 ], "category_id": 1, "smiles": "N#[N+]=CC1(O)CCCCC1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6491 0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.0586 -0.4512 0.0000 N 0 0 0 0 0 5 0 0 0 0 0 0\n -5.2077 -1.4153 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 10 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 9 1 0\n 6 7 2 0\n 7 8 3 0\n 9 10 1 0\nM CHG 1 7 1\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.4352176088044022, 0.8854583413317176, 0.49524762381190596, 0.9232656591237279 ], "category_id": 2, "text": [ "Nz" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5242621310655328, 0.8564179378103185, 0.6583291645822912, 0.9731274840378283 ], "category_id": 1, "smiles": "[H]OC1CCCCCC1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 12.5510 1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3886 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9179 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1625 1.0000 0.0000 C 0 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0 0 0 0 0\n 7.5108 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 9 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6908454227113556, 0.8706641735000614, 0.7563781890945472, 0.9155946091369431 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7763881940970485, 0.8509386163911865, 0.8804402201100551, 0.9632647054833908 ], "category_id": 1, "smiles": "O=C1CCCCCC1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 0.6366 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0344 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6602 -1.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6042 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8322 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6386 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0472 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8645 -8.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 8 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 7 8 1 0\nM END\n" } ] } ], "Truce\u2212Smile rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.01950975487743872, 0.09743684627701978, 0.2986493246623312, 0.8403927991392957 ], "category_id": 1, "smiles": "*c1ccccc1*C[YH]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 0.9911 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1713 -7.0315 0.0000 Y 0 0 0 0 0 2 0 0 0 0 0 0\n 3.6039 -2.8583 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0365 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5592 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5592 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9918 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9918 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5592 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0365 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 2 0\n 4 10 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\nM RAD 1 2 2\nA 3\nX\nA 6\nZ\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.42021010505252626, 0.30753504606184373, 0.5417708854427213, 0.4765270763235499 ], "category_id": 2, "text": [ "base" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6873436718359179, 0.05480822603082363, 0.9624812406203102, 0.7977641788930995 ], "category_id": 1, "smiles": "*C*c1ccccc1*", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 1.0721 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0721 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4843 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8964 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3086 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3979 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8101 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.8101 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3086 -8.4488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8964 -7.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 3 4 1 0\n 4 5 2 0\n 4 10 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 0\n 8 9 1 0\n 9 10 2 0\nA 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0.7298649324662331, 0.35483364203910045, 0.8989494747373686, 0.4590098379879869 ], "category_id": 1, "smiles": "*C/C=C/[1*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 5.3993 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0247 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7739 -1.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1485 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.5231 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\n 3 4 1 0\n 4 5 1 0\nM ISO 1 2 1\nA 2\nR1\nA 5\nX\nM END\n" } ], "conditions": [ { "category": "[Idt]", "bbox": [ 0.7293646823411706, 0.5140064084381604, 0.7563781890945472, 0.5467928254373023 ], "category_id": 3, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5722861430715358, 0.604962274951909, 0.7198599299649825, 0.7567316568672917 ], "category_id": 1, "smiles": "**(C)C.*CCC", "molfile": "\n RDKit 2D\n\n 8 6 0 0 0 0 0 0 0 0999 V2000\n 3.7999 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8722 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8722 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2679 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 3.3957 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8722 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2679 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nM ISO 1 5 1\nA 1\n*\nA 2\nPd(11)\nA 5\n1*\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.5722861430715358, 0.604962274951909, 0.7198599299649825, 0.7567316568672917 ], "category_id": 1, "smiles": "**(C)C.*CCC", "molfile": "\n RDKit 2D\n\n 8 6 0 0 0 0 0 0 0 0999 V2000\n 3.7999 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8722 -5.1417 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8722 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2679 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 3.3957 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8722 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2679 -1.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\nM ISO 1 5 1\nA 1\n*\nA 2\nPd(11)\nA 5\n1*\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5137568784392196, 0.6298164942899682, 0.5662831415707854, 0.6673622298857597 ], "category_id": 2, "text": [] }, { "category": "[Txt]", "bbox": [ 0.5147573786893447, 0.6869283174497637, 0.5662831415707854, 0.7213011739811223 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3296648324162081, 0.6044334617745034, 0.47573786893446723, 0.7546164041576696 ], "category_id": 1, "smiles": "**(*)C.*/C=C/C", "molfile": "\n RDKit 2D\n\n 8 6 0 0 0 0 0 0 0 0999 V2000\n 4.1605 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0973 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7077 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9341 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 3.7526 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0157 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3604 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\nM ISO 1 5 1\nA 1\n*\nA 2\nPd(1)\nA 3\n*\nA 5\n1*\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3296648324162081, 0.6044334617745034, 0.47573786893446723, 0.7546164041576696 ], "category_id": 1, "smiles": "**(*)C.*/C=C/C", "molfile": "\n RDKit 2D\n\n 8 6 0 0 0 0 0 0 0 0999 V2000\n 4.1605 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0973 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7077 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9341 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 3.7526 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0157 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3604 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\nM ISO 1 5 1\nA 1\n*\nA 2\nPd(1)\nA 3\n*\nA 5\n1*\nM 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0.2242167872199383 ], "category_id": 2, "text": [ "LnPd(o)" ] } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3296648324162081, 0.6044334617745034, 0.47573786893446723, 0.7546164041576696 ], "category_id": 1, "smiles": "**(*)C.*/C=C/C", "molfile": "\n RDKit 2D\n\n 8 6 0 0 0 0 0 0 0 0999 V2000\n 4.1605 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0973 -4.9843 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7077 -9.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.9341 -1.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 1.0000 0.0000 R 0 0 0 0 0 1 0 0 0 0 0 0\n 3.7526 -0.8898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0157 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3604 -0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\nM ISO 1 5 1\nA 1\n*\nA 2\nPd(1)\nA 3\n*\nA 5\n1*\nM END\n" }, { "category": "[Txt]", "bbox": [ 0.12606303151575787, 0.5859250005653104, 0.18859429714857429, 0.62135548345148 ], "category_id": 2, "text": [ "NuO" ] } ], "conditions": [], 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0\n 12 13 1 0\nM CHG 2 2 1 5 -1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6263131565782891, 0.3386317767851601, 0.7298649324662331, 0.6306756089202057 ], "category_id": 1, "smiles": "[H]C([Cl-])(C1=CC=C(OC)C=C1)[N+](C)C", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 5.2500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 -1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 14 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 13 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 12 2 0\n 10 11 1 0\n 12 13 1 0\nM CHG 2 2 1 5 -1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.1615807903951976, 0.8017298534564468, 0.21560780390195097, 0.9192427287679295 ], "category_id": 1, "smiles": "[H]O[H]", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 3.5640 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4557 -7.4252 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4557 -0.7323 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.23411705852926462, 0.6508405401866731, 0.3371685842921461, 0.9366262902045392 ], "category_id": 1, "smiles": "[H]C(c1ccc(OC)cc1)=[N+](C)C", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.5512 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9291 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9291 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2677 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2677 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9291 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9291 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5512 -7.1890 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2677 -7.1890 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 4.6850 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2677 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5512 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5512 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 2 0\n 3 13 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 12 1 0\n 7 8 1 0\n 7 9 2 3\n 9 10 1 0\n 9 11 1 0\n 12 13 2 0\nM CHG 1 9 1\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.23411705852926462, 0.6508405401866731, 0.3371685842921461, 0.9366262902045392 ], "category_id": 1, "smiles": "[H]C(c1ccc(OC)cc1)=[N+](C)C", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.5512 0.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9291 -0.1024 0.0000 O 0 0 0 0 0 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0.8469271131916323 ], "category_id": 2, "text": [ "workup" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4942471235617809, 0.6508405401866731, 0.5992996498249125, 0.9706980706202946 ], "category_id": 1, "smiles": "[H]C(O)(c1ccc(OC)cc1)[N+]([H])(C)C", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 1.4369 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6583 -7.0315 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 2.6583 -8.4488 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6583 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0234 -5.6142 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2573 -5.6142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6583 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8438 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8438 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6583 -1.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6583 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4369 0.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4369 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.4369 -3.4882 0.0000 C 0 0 0 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0 0 0 0\n 4.0923 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8188 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1835 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0923 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 1 0\n 3 4 1 0\n 3 5 1 0\n 3 6 1 0\n 6 7 1 0\n 6 8 2 0\n 9 10 2 0\n 9 11 1 0\n 11 12 1 0\nA 1\nEtO2C\nA 4\nR\nA 7\nR\nA 12\nEtO2C\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.07953976988494248, 0.39183417692159545, 0.2651325662831416, 0.6286832331541218 ], "category_id": 1, "smiles": "*C1(*)C([H])(C(OCC)OCC)C(=O)C([H])(C(OCC)OCC)C1(*)O", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 4.1160 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0760 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0760 -0.0236 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7040 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4500 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0760 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1160 -6.9528 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0760 -8.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2320 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5840 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3100 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2320 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7220 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3880 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 12 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 12 1 0\n 12 13 1 0\n 12 14 1 0\nA 1\nEtO2C\nA 7\nEtO2C\nA 10\nIn14\nA 11\nR\nA 13\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.36218109054527264, 0.39342376790302186, 0.51975987993997, 0.6326572106076876 ], "category_id": 1, "smiles": "*C1=C(OCC)/C(=C/[H])C(C(OCC)OCC)=C1[1*]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 4.6805 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3375 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1057 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8886 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8211 -5.7717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3375 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6805 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3903 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1969 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3903 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1969 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 2 0\n 3 4 2 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\nM ISO 1 9 1\nA 1\nEtO\nA 7\nEtO2C\nA 9\nR1\nA 11\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5242621310655328, 0.3870654039773164, 0.6128064032016008, 0.6262988466819822 ], "category_id": 1, "smiles": "[H][O-]C(=CC(=O)OCC)CC(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -2.2500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 6 2 3\n 4 5 1 0\n 6 7 1 0\nM CHG 1 4 -1\nA 1\nCO2Et\nA 7\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.36218109054527264, 0.39342376790302186, 0.51975987993997, 0.6326572106076876 ], "category_id": 1, "smiles": "*C1=C(OCC)/C(=C/[H])C(C(OCC)OCC)=C1[1*]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 4.6805 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3375 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1057 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8886 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8211 -5.7717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3375 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6805 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3903 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1969 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3903 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1969 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 2 0\n 3 4 2 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\nM ISO 1 9 1\nA 1\nEtO\nA 7\nEtO2C\nA 9\nR1\nA 11\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5242621310655328, 0.3870654039773164, 0.6128064032016008, 0.6262988466819822 ], "category_id": 1, "smiles": "[H][O-]C(=CC(=O)OCC)CC(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -2.2500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 6 2 3\n 4 5 1 0\n 6 7 1 0\nM CHG 1 4 -1\nA 1\nCO2Et\nA 7\nCO2Et\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.07953976988494248, 0.39183417692159545, 0.2651325662831416, 0.6286832331541218 ], "category_id": 1, "smiles": "*C1(*)C([H])(C(OCC)OCC)C(=O)C([H])(C(OCC)OCC)C1(*)O", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 4.1160 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0760 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0760 -0.0236 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7040 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4500 -4.0394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0760 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1160 -6.9528 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0760 -8.0551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2320 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5840 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3100 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2320 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7220 -0.7323 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3880 -2.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 12 1 0\n 4 5 2 0\n 4 6 1 0\n 6 7 1 0\n 6 8 1 0\n 6 9 1 0\n 9 10 1 0\n 9 11 1 0\n 9 12 1 0\n 12 13 1 0\n 12 14 1 0\nA 1\nEtO2C\nA 7\nEtO2C\nA 10\nIn14\nA 11\nR\nA 13\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.36218109054527264, 0.39342376790302186, 0.51975987993997, 0.6326572106076876 ], "category_id": 1, "smiles": "*C1=C(OCC)/C(=C/[H])C(C(OCC)OCC)=C1[1*]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 4.6805 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3375 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1057 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8886 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8211 -5.7717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3375 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6805 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3903 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1969 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3903 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1969 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 2 0\n 3 4 2 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\nM ISO 1 9 1\nA 1\nEtO\nA 7\nEtO2C\nA 9\nR1\nA 11\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5242621310655328, 0.3870654039773164, 0.6128064032016008, 0.6262988466819822 ], "category_id": 1, "smiles": "[H][O-]C(=CC(=O)OCC)CC(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -2.2500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 6 2 3\n 4 5 1 0\n 6 7 1 0\nM CHG 1 4 -1\nA 1\nCO2Et\nA 7\nCO2Et\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6953476738369184, 0.39183417692159545, 0.9404702351175588, 0.6334520060984009 ], "category_id": 1, "smiles": "*C1(C(C(=O)CC(=O)OCC)C(=O)OCC)C([7*])=C(C(OCC)OCC)C(O)=C1C(OCC)OCC", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 4.6903 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4509 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0565 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0283 -3.8819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4509 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6903 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4792 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4933 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4792 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9863 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5075 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0145 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1554 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1837 -3.1732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5216 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0428 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 9 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 1 0\n 13 14 2 0\n 13 15 1 0\n 15 16 1 0\nM ISO 1 8 7\nA 1\nEtO2C\nA 6\nEtO2C\nA 8\nR7\nA 10\nR\nA 12\nCO2Et\nA 16\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6953476738369184, 0.39183417692159545, 0.9404702351175588, 0.6334520060984009 ], "category_id": 1, "smiles": "*C1(C(C(=O)CC(=O)OCC)C(=O)OCC)C([7*])=C(C(OCC)OCC)C(O)=C1C(OCC)OCC", "molfile": "\n RDKit 2D\n\n 16 16 0 0 0 0 0 0 0 0999 V2000\n 4.6903 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4509 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0565 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0283 -3.8819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4509 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6903 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4792 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4933 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4792 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9863 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5075 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0145 -0.1024 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.1554 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.1837 -3.1732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5216 -5.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.0428 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 9 1 0\n 3 4 1 0\n 3 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 1 0\n 9 11 1 0\n 11 12 1 0\n 11 13 1 0\n 13 14 2 0\n 13 15 1 0\n 15 16 1 0\nM ISO 1 8 7\nA 1\nEtO2C\nA 6\nEtO2C\nA 8\nR7\nA 10\nR\nA 12\nCO2Et\nA 16\nCO2Et\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.36218109054527264, 0.39342376790302186, 0.51975987993997, 0.6326572106076876 ], "category_id": 1, "smiles": "*C1=C(OCC)/C(=C/[H])C(C(OCC)OCC)=C1[1*]", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 4.6805 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3375 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1057 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8886 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8211 -5.7717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3375 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6805 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3903 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1969 -6.2441 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3903 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1969 -1.4409 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 2 0\n 3 4 2 0\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\nM ISO 1 9 1\nA 1\nEtO\nA 7\nEtO2C\nA 9\nR1\nA 11\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.5242621310655328, 0.3870654039773164, 0.6128064032016008, 0.6262988466819822 ], "category_id": 1, "smiles": "[H][O-]C(=CC(=O)OCC)CC(=O)OCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 -2.2500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8971 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1962 -0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 3 6 2 3\n 4 5 1 0\n 6 7 1 0\nM CHG 1 4 -1\nA 1\nCO2Et\nA 7\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.12206103051525763, 0.7256482830211292, 0.37018509254627313, 0.9640869302350819 ], "category_id": 1, "smiles": "*C1(C(C(=O)OCC)C(=CC(=O)OCC)O[H])C([1*])=C(C(OCC)OCC)C(=O[H])C1C(OCC)OCC", "molfile": "\n RDKit 2D\n\n 18 18 0 0 0 0 0 0 0 0999 V2000\n 2.7760 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 2.6401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.1459 3.7548 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6933 -1.9635 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.2158 -2.5838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7076 -2.7406 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6659 -3.7974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0558 -5.1677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9374 -6.3812 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1577 -3.6406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0393 -4.8541 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 10 1 0\n 3 4 2 3\n 3 6 1 0\n 4 5 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 1 0\n 12 13 1 0\n 12 14 1 0\n 14 15 1 0\n 14 17 2 3\n 15 16 1 0\n 17 18 1 0\nM ISO 1 9 1\nA 1\nEtO2C\nA 7\nEtO2C\nA 9\nR1\nA 11\nR\nA 13\nCO2Et\nA 18\nCO2Et\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4432216108054027, 0.7200847145861369, 0.6623311655827914, 0.9585233618000897 ], "category_id": 1, "smiles": "*[C@]12C(C(OCC)OCC)C(O)=C(C(OCC)OCC)[C@@]1([7*])C(C(=O)OCC)C(=O)C2C(=O)OCC", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 10.3495 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6595 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0395 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.2244 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6595 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3495 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5197 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8298 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1398 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9549 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5197 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8298 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 9 1 0\n 7 15 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\n 13 15 1 0\n 7 8 1 1\n 15 16 1 1\nM ISO 1 8 7\nA 1\nCO2Et\nA 6\nCO2Et\nA 8\nR7\nA 10\nEtO2C\nA 14\nEtO2C\nA 16\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4432216108054027, 0.7200847145861369, 0.6623311655827914, 0.9585233618000897 ], "category_id": 1, "smiles": "*[C@]12C(C(OCC)OCC)C(O)=C(C(OCC)OCC)[C@@]1([7*])C(C(=O)OCC)C(=O)C2C(=O)OCC", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 10.3495 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6595 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0395 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.2244 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6595 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3495 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5197 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8298 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1398 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9549 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5197 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8298 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 9 1 0\n 7 15 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\n 13 15 1 0\n 7 8 1 1\n 15 16 1 1\nM ISO 1 8 7\nA 1\nCO2Et\nA 6\nCO2Et\nA 8\nR7\nA 10\nEtO2C\nA 14\nEtO2C\nA 16\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.12206103051525763, 0.7256482830211292, 0.37018509254627313, 0.9640869302350819 ], "category_id": 1, "smiles": "*C1(C(C(=O)OCC)C(=CC(=O)OCC)O[H])C([1*])=C(C(OCC)OCC)C(=O[H])C1C(OCC)OCC", "molfile": "\n RDKit 2D\n\n 18 18 0 0 0 0 0 0 0 0999 V2000\n 2.0788 -2.4709 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 -1.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3907 1.0037 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 1.6317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6161 1.0216 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2458 -1.6317 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8578 -2.6401 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8173 -0.5402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9320 -1.5439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.3586 -1.0803 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1291 0.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5557 1.3906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 14 1 0\n 3 4 1 0\n 3 5 1 0\n 3 12 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 2 3\n 7 10 1 0\n 8 9 1 0\n 10 11 1 0\n 10 12 2 0\n 12 13 1 0\n 14 15 1 0\n 14 17 2 3\n 15 16 1 0\n 17 18 1 0\nM ISO 1 13 1\nA 1\nCO2Et\nA 4\nR\nA 6\nEtO2C\nA 11\nEtO2C\nA 13\nR1\nA 18\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4432216108054027, 0.7200847145861369, 0.6623311655827914, 0.9585233618000897 ], "category_id": 1, "smiles": "*[C@]12C(C(OCC)OCC)C(O)=C(C(OCC)OCC)[C@@]1([7*])C(C(=O)OCC)C(=O)C2C(=O)OCC", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 10.3495 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6595 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0395 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.2244 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6595 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3495 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5197 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8298 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1398 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9549 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5197 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8298 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 9 1 0\n 7 15 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\n 13 15 1 0\n 7 8 1 1\n 15 16 1 1\nM ISO 1 8 7\nA 1\nCO2Et\nA 6\nCO2Et\nA 8\nR7\nA 10\nEtO2C\nA 14\nEtO2C\nA 16\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7388694347173587, 0.7121367596790052, 0.9634817408704353, 0.9513702023836711 ], "category_id": 1, "smiles": "*[C@@]12C(C(=O)OCC)=C(O)C(C(=O)OCC)[C@]1([7*])C(C(OCC)OCC)=C(O)C2C(OCC)OCC", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 10.2267 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6389 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5231 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5231 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4072 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8195 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2317 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9983 -3.7244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4072 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8195 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5231 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5231 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6389 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2267 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9319 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0478 -3.7244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 2 3\n 3 5 1 0\n 3 11 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 9 11 1 0\n 11 13 1 0\n 13 14 1 0\n 13 15 1 0\n 15 16 1 0\n 3 4 1 1\n 11 12 1 1\nM ISO 1 12 7\nA 1\nCO2Et\nA 4\nR\nA 6\nEtO2C\nA 10\nEtO2C\nA 12\nR7\nA 14\nCO2Et\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7388694347173587, 0.7121367596790052, 0.9634817408704353, 0.9513702023836711 ], "category_id": 1, "smiles": "*[C@@]12C(C(=O)OCC)=C(O)C(C(=O)OCC)[C@]1([7*])C(C(OCC)OCC)=C(O)C2C(OCC)OCC", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 10.2267 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6389 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5231 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5231 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4072 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8195 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2317 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9983 -3.7244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4072 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8195 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5231 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5231 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6389 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.2267 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9319 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.0478 -3.7244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 2 3\n 3 5 1 0\n 3 11 1 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 9 2 0\n 9 10 1 0\n 9 11 1 0\n 11 13 1 0\n 13 14 1 0\n 13 15 1 0\n 15 16 1 0\n 3 4 1 1\n 11 12 1 1\nM ISO 1 12 7\nA 1\nCO2Et\nA 4\nR\nA 6\nEtO2C\nA 10\nEtO2C\nA 12\nR7\nA 14\nCO2Et\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4432216108054027, 0.7200847145861369, 0.6623311655827914, 0.9585233618000897 ], "category_id": 1, "smiles": "*[C@]12C(C(OCC)OCC)C(O)=C(C(OCC)OCC)[C@@]1([7*])C(C(=O)OCC)C(=O)C2C(=O)OCC", "molfile": "\n RDKit 2D\n\n 16 17 0 0 0 0 0 0 0 0999 V2000\n 10.3495 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6595 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.0395 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.2244 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6595 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3495 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5197 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8298 -7.7402 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1398 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9549 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5197 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8298 0.0551 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.5896 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 15 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 7 1 0\n 7 9 1 0\n 7 15 1 0\n 9 10 1 0\n 9 11 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 1 0\n 13 15 1 0\n 7 8 1 1\n 15 16 1 1\nM ISO 1 8 7\nA 1\nCO2Et\nA 6\nCO2Et\nA 8\nR7\nA 10\nEtO2C\nA 14\nEtO2C\nA 16\nR\nM END\n" } ] } ], "Wharton reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04202101050525263, 0.08747707186926797, 0.19159579789894948, 0.3556444889111222 ], "category_id": 1, "smiles": "[1*][C@H]1O[C@@H]1C([2*])=O", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 V2000\n 11.8805 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8805 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.2571 -5.5354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7541 -5.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2524 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2524 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1260 -5.5354 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 4 1 0\n 4 6 1 0\n 6 7 1 0\n 4 5 1 1\n 6 5 1 1\nM ISO 2 1 2 7 1\nA 1\nR2\nA 7\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3776888444222111, 0.08317492079373019, 0.599799899949975, 0.43164915791228947 ], "category_id": 1, "smiles": "[1*]C1O[C@@H]1C([2*])(O)NN.[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 4.3164 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7266 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3164 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7623 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0644 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0644 -1.5984 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7981 -4.3543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5032 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1074 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.3951 -1.5984 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 4 3 1 1\nM ISO 2 2 1 6 2\nA 2\nR1\nA 6\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3776888444222111, 0.08317492079373019, 0.599799899949975, 0.43164915791228947 ], "category_id": 1, "smiles": "[1*]C1O[C@@H]1C([2*])(O)NN.[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 4.3164 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7266 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3164 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7623 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0644 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0644 -1.5984 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7981 -4.3543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5032 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1074 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.3951 -1.5984 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 4 3 1 1\nM ISO 2 2 1 6 2\nA 2\nR1\nA 6\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.6288144072036018, 0.14770718692679674, 0.7143571785892946, 0.25382691345672836 ], "category_id": 2, "text": [ "HzO" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7633816908454227, 0.054493913623478406, 0.968984492246123, 0.31979322994830744 ], "category_id": 1, "smiles": "[1*]C1OC1/C([2*])=N/N([H])[H]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 5.5793 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2666 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5793 -7.4252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7177 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6817 -3.8031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.6817 -0.4961 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.8200 -5.6929 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 17.7840 -3.9606 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 17.7840 -0.5748 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 20.7480 -5.8504 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 2 0\n 7 8 1 0\n 8 9 1 0\n 8 10 1 0\n 4 3 1 1\nM ISO 2 2 1 6 2\nA 2\nR1\nA 6\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3776888444222111, 0.08317492079373019, 0.599799899949975, 0.43164915791228947 ], "category_id": 1, "smiles": "[1*]C1O[C@@H]1C([2*])(O)NN.[H]", "molfile": "\n RDKit 2D\n\n 10 9 0 0 0 0 0 0 0 0999 V2000\n 4.3164 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7266 -5.6929 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3164 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7623 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0644 -4.2756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.0644 -1.5984 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7981 -4.3543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5032 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.1074 -6.7165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.3951 -1.5984 0.0000 H 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 1 0\n 4 3 1 1\nM ISO 2 2 1 6 2\nA 2\nR1\nA 6\nR2\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.10855427713856929, 0.695514423878606, 0.2786393196598299, 0.7901617475404368 ], "category_id": 2, "text": [ "tautomerization" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.3181590795397699, 0.6023011505752877, 0.527263631815908, 0.8719026179756545 ], "category_id": 1, "smiles": "[1*]C1O[C@@H]1C([2*])([H])/N=N\\[H]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 5.6026 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2761 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6026 -7.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7541 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7304 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.7068 -2.3071 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7304 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.7068 -5.7717 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 17.8583 -7.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 21.0097 -5.7717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 2 0\n 9 10 1 0\n 4 3 1 1\nM ISO 2 2 1 7 2\nA 2\nR1\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3181590795397699, 0.6023011505752877, 0.527263631815908, 0.8719026179756545 ], "category_id": 1, "smiles": "[1*]C1O[C@@H]1C([2*])([H])/N=N\\[H]", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 5.6026 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2761 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6026 -7.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7541 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7304 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.7068 -2.3071 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.7304 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 14.7068 -5.7717 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 17.8583 -7.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 21.0097 -5.7717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 8 9 2 0\n 9 10 1 0\n 4 3 1 1\nM ISO 2 2 1 7 2\nA 2\nR1\nA 7\nR2\nM END\n" } ], "conditions": [], "products": [ { "category": "[Txt]", "bbox": [ 0.6858429214607303, 0.7428380857095214, 0.7383691845922962, 0.856128064032016 ], "category_id": 2, "text": [ "Nz^" ] }, { "category": "[Mol]", "bbox": [ 0.7838919459729865, 0.6797398699349675, 0.9204602301150575, 0.904885776221444 ], "category_id": 1, "smiles": "[1*][C@H](O)/C=C\\[2*]", "molfile": "\n RDKit 2D\n\n 6 5 0 0 0 0 0 0 0 0999 V2000\n 10.9127 -6.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3661 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3661 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6830 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5958 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.5958 -0.8110 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 5 2 0\n 2 3 1 0\n 5 6 1 0\n 2 4 1 1\nM ISO 2 3 1 6 2\nA 3\nR1\nA 6\nR2\nM END\n" } ] } ], "Willgerodt\u2013Kindler reaction.png": [], "Wittig reaction.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1645822911455728, 0.061743834880403164, 0.25062531265632815, 0.20169652727598367 ], "category_id": 1, "smiles": "*C(*)*", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.0251 -5.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.5346 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0251 -1.2835 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5953 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\nA 2\nX\nA 3\nR\nA 4\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.30665332666333167, 0.0749158529882225, 0.3626813406703352, 0.13418993447340954 ], "category_id": 2, "text": [ "SN2" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.4122061030515258, 0.03951605432345802, 0.5447723861930965, 0.23956607933596424 ], "category_id": 1, "smiles": "*C(*)([H])P(c1ccccc1)(c1ccccc1)c1ccccc1", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 7.1350 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2122 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1350 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1350 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8859 -5.0630 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nA 2\nPh3P\nA 3\nR\nA 4\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.4122061030515258, 0.03951605432345802, 0.5447723861930965, 0.23956607933596424 ], "category_id": 1, "smiles": "*C(*)([H])P(c1ccccc1)(c1ccccc1)c1ccccc1", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 7.1350 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2122 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1350 -7.8189 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1350 -2.3071 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.8859 -5.0630 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nA 2\nPh3P\nA 3\nR\nA 4\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7138569284642321, 0.08150186204213217, 0.8369184592296148, 0.23544982367727074 ], "category_id": 1, "smiles": "*C(=*)[7*]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.4649 -4.2756 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1770 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9299 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9299 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 2 4 1 0\nM ISO 1 4 7\nA 1\nPh3\nA 3\nR\nA 4\nR7\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7138569284642321, 0.08150186204213217, 0.8369184592296148, 0.23544982367727074 ], "category_id": 1, "smiles": "*C(=*)[7*]", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.4649 -4.2756 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1770 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9299 -7.4252 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9299 -1.2047 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 2 4 1 0\nM ISO 1 4 7\nA 1\nPh3\nA 3\nR\nA 4\nR7\nM END\n" } ], "conditions": [ { "category": "[Mol]", "bbox": [ 0.12156078039019509, 0.34329572193504154, 0.21160580290145073, 0.475015903013235 ], "category_id": 1, "smiles": "[2*]C([3*])=O", "molfile": "\n RDKit 2D\n\n 4 3 0 0 0 0 0 0 0 0999 V2000\n 5.9350 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4803 -7.0315 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9350 -0.8898 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5669 -7.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 2 0\nM ISO 2 2 2 3 3\nA 2\nR2\nA 3\nR3\nM END\n" } ], "products": [ { "category": "[Mol]", "bbox": [ 0.24512256128064033, 0.3087191744020158, 0.4702351175587794, 0.593564065983609 ], "category_id": 1, "smiles": "*C1([1*])OC2([2*])C([3*])C12([3*])P(c1ccccc1)(c1ccccc1)c1ccccc1", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n -0.0000 -1.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -2.3597 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0607 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 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"cycloaddition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6803401700850426, 0.28649139384507066, 0.8134067033516759, 0.528527226576251 ], "category_id": 1, "smiles": "[1*]C([3*])(C([2*])([3*])O)P(c1ccccc1)(c1ccccc1)c1ccccc1", "molfile": "\n RDKit 2D\n\n 8 7 0 0 0 0 0 0 0 0999 V2000\n 5.5834 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5834 -6.8740 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.7287 -2.6220 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9456 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5791 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3622 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0021 -3.4094 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5791 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\nM ISO 4 3 1 4 3 6 3 7 2\nA 2\nPPh3\nA 3\nR1\nA 4\nR3\nA 6\nR3\nA 7\nR2\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.25812906453226614, 0.7540980366726573, 0.39569784892446225, 0.9088692494395345 ], "category_id": 1, "smiles": "*C(*)([1*])C([2*])([3*])[3*].OP(c1ccccc1)(c1ccccc1)c1ccccc1", "molfile": "\n RDKit 2D\n\n 10 8 0 0 0 0 0 0 0 0999 V2000\n 5.2839 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0204 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8379 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2839 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7300 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7638 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1760 -5.0630 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.7638 -7.5039 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7300 -0.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2839 -0.5748 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\n 5 6 1 0\n 5 7 1 0\n 5 8 1 0\n 9 10 1 0\nM ISO 4 2 1 6 2 7 3 8 3\nA 2\nR1\nA 3\nR\nA 4\nR\nA 6\nR2\nA 7\nR3\nA 8\nR3\nA 10\nPh3P\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.4942471235617809, 0.8084326113674121, 0.5927963981990996, 0.8685299439843377 ], "category_id": 1, 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0.545272636318159, 0.12638080945234523, 0.6578289144572286, 0.19560446890111724 ], "category_id": 2, "text": [ "homolytic", "cleavage" ] } ], "products": [ { "category": "[Txt]", "bbox": [ 0.6953476738369184, 0.10097763167297935, 0.752376188094047, 0.15495938445413182 ], "category_id": 2, "text": [ "NzT" ] }, { "category": "[Txt]", "bbox": [ 0.7958979489744873, 0.10605826722885252, 0.8224112056028015, 0.15114890778722695 ], "category_id": 2, "text": [ "2" ] }, { "category": "[Mol]", "bbox": [ 0.8349174587293647, 0.07684461278258177, 0.9214607303651826, 0.17337668834417208 ], "category_id": 1, "smiles": "CCC", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 0.0000 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7448 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7448 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.2681340670335168, 0.2711789227947307, 0.384192096048024, 0.4610676766954906 ], 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0.6319040472617261, 0.47423711855927964, 0.7233554872674433 ], "category_id": 1, "smiles": "C/C=C\\CCCC", "molfile": "\n RDKit 2D\n\n 7 6 0 0 0 0 0 0 0 0999 V2000\n 0.8624 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1046 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8478 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.9524 -4.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8478 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1046 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3798 -2.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 3 4 1 0\n 4 5 1 0\n 5 6 2 0\n 6 7 1 0\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.5147573786893447, 0.6325391267062103, 0.6658329164582291, 0.6712789728197432 ], "category_id": 2, "text": [ "H abstraction" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.7113556778389195, 0.5830029300364468, 0.8019009504752376, 0.7716215250482383 ], "category_id": 1, "smiles": "O=C1CCC(=O)N1", "molfile": "\n RDKit 2D\n\n 7 7 0 0 0 0 0 0 0 0999 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C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8569 -4.5906 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6933 -1.2835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3865 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1609 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.1609 -1.2835 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9972 -4.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 11.9972 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.0784 -7.9764 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 15 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 12 2 0\n 5 6 1 0\n 5 7 1 0\n 5 11 1 0\n 7 8 1 0\n 8 9 1 0\n 8 10 2 0\n 12 13 1 0\n 12 14 1 0\n 14 15 2 0\n 15 16 1 0\nA 9\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7338669334667334, 0.045988511497127876, 0.9354677338669335, 0.19249476955226383 ], "category_id": 1, "smiles": "*C(=O)OC(=O)c1c(Cl)cc(Cl)cc1Cl", "molfile": "\n RDKit 2D\n\n 15 15 0 0 0 0 0 0 0 0999 V2000\n 12.2121 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9401 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.1001 -7.5039 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9401 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8101 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5381 -3.7244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2660 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9940 -3.7244 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2660 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8101 -0.1024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2121 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2121 -0.1024 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4842 -3.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 14.4842 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 16.7562 -7.5039 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 14 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 1 0\n 4 11 2 0\n 5 6 1 0\n 5 10 2 0\n 6 7 1 0\n 7 8 1 0\n 7 9 2 0\n 11 12 1 0\n 11 13 1 0\n 13 14 2 0\n 14 15 1 0\nA 8\nR\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7208604302151076, 0.17738425863177895, 0.783391695847924, 0.3435998787571125 ], "category_id": 1, "smiles": "CN(C)C1=CC=[Ni]C=C1", "molfile": "\n RDKit 2D\n\n 9 9 0 0 0 0 0 0 0 0999 V2000\n 0.4233 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4629 -7.4252 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4629 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4254 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4254 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4629 -0.5748 0.0000 Ni 0 0 0 0 0 3 0 0 0 0 0 0\n 0.5003 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5003 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4254 -8.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 9 1 0\n 3 4 1 0\n 3 8 2 0\n 4 5 2 0\n 5 6 1 0\n 6 7 2 0\n 7 8 1 0\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.1535767883941971, 0.40469890117472535, 0.43621810905452724, 0.6320135437176717 ], "category_id": 1, "smiles": "*C(O)(OC(=O)C1=C(Cl)C=C(Cl)C=C1Cl)n1=CC=C(N(C)C)C=C1", "molfile": "\n RDKit 2D\n\n 24 25 0 0 0 0 0 0 0 0999 V2000\n 3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.5000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.2990 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.2990 3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7010 3.7500 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.2990 6.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.2990 8.2500 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n -5.5981 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.8971 3.7500 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n -5.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 24 1 0\n 3 4 1 0\n 3 23 2 0\n 4 5 2 0\n 5 6 1 0\n 6 7 1 0\n 6 22 2 0\n 7 8 1 0\n 7 9 1 0\n 7 21 1 0\n 9 10 1 0\n 10 11 1 0\n 10 20 2 0\n 11 12 1 0\n 11 18 2 0\n 12 13 1 0\n 12 14 2 0\n 14 15 1 0\n 15 16 1 0\n 15 17 2 0\n 17 18 1 0\n 18 19 1 0\n 22 23 1 0\nA 8\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5142571285642822, 0.4500304339361799, 0.6683341670835418, 0.6024495006123751 ], "category_id": 1, "smiles": "O=C(O)c1c(Cl)cc(Cl)cc1Cl", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 9.9095 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9095 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2288 -7.8189 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6957 -7.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4819 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6355 -7.8189 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4819 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2680 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0542 -3.9606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2680 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6957 -2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6957 -0.1811 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 1 11 1 0\n 2 3 1 0\n 2 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 7 1 0\n 7 8 1 0\n 7 11 2 0\n 8 9 1 0\n 8 10 2 0\n 11 12 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.7398699349674838, 0.4428036678437741, 0.9089544772386193, 0.6162460540615136 ], "category_id": 1, "smiles": "*C(=O)[n+]1ccc(N(C)C)cc1.*O", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 0.9089 -6.7953 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 1.9189 -8.3701 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5033 -8.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.5033 -6.1654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6854 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.6854 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8675 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0496 -3.0157 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0\n 3.1308 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3129 -3.0157 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1308 0.0551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0496 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8675 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4221 -5.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 3 4 1 0\n 4 5 1 0\n 4 14 1 0\n 5 6 2 0\n 5 13 1 0\n 6 7 1 0\n 7 8 2 0\n 8 9 1 0\n 8 12 1 0\n 9 10 1 0\n 9 11 2 0\n 12 13 2 0\nM CHG 1 8 1\nM RAD 1 1 2\nA 2\nL\nA 10\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.34517258629314657, 0.7831186529225204, 0.5477738869434717, 0.967072698911032 ], "category_id": 1, "smiles": "*C(C)(O[1*])=[N+]1=CC=C(N(C)C)C=C1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 3.0000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 1.2990 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 N 0 0 0 0 0 5 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 1 0\n 2 4 1 0\n 2 6 2 0\n 4 5 1 0\n 6 7 1 0\n 6 14 2 0\n 7 8 2 0\n 8 9 1 0\n 9 10 1 0\n 9 13 2 0\n 10 11 1 0\n 10 12 1 0\n 13 14 1 0\nM CHG 1 6 1\nM ISO 1 5 1\nA 3\nR\nA 5\nR1\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.6383191595797899, 0.828450185683975, 0.743871935967984, 0.9191132512068843 ], "category_id": 1, "smiles": "*C(=O)O[1*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 5.4626 -4.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6995 -7.1102 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.1043 -7.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8675 -4.9055 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4626 -0.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 5 2 0\n 3 4 1 0\nM ISO 1 4 1\nA 2\nR\nA 4\nR1\nM END\n" } ] } ], "Zincke reaction.png": [], "[1,2]-Meisenheimer rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.0080040020010005, 0.14496378624094658, 0.21960980490245122, 0.9462181683727239 ], "category_id": 1, "smiles": "*N(*)([2*])[7*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 1.2990 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0000 0.0000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5981 1.5000 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0490 -0.5490 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5490 2.0490 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 1 5 1 0\nM ISO 2 3 7 4 2\nA 2\nOe\nA 3\nR7\nA 4\nR2\nA 5\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2831415707853927, 0.3162846245257016, 0.32416208104052024, 0.5561337981243587 ], "category_id": 2, "text": [] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.39419709854927465, 0.026357052043808466, 0.6718359179589795, 0.8434256654018709 ], "category_id": 1, "smiles": "*.[1*]N([2*])O", "molfile": "\n RDKit 2D\n\n 5 3 0 0 0 0 0 0 0 0999 V2000\n 6.2647 -4.6693 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5628 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2647 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6818 -6.7165 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 16.2313 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\nM RAD 1 4 2\nM ISO 2 2 2 3 1\nA 2\nR2\nA 3\nR1\nA 5\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.39419709854927465, 0.026357052043808466, 0.6718359179589795, 0.8434256654018709 ], "category_id": 1, "smiles": "*.[1*]N([2*])O", "molfile": "\n RDKit 2D\n\n 5 3 0 0 0 0 0 0 0 0999 V2000\n 6.2647 -4.6693 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5628 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2647 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6818 -6.7165 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0\n 16.2313 -2.7795 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\nM RAD 1 4 2\nM ISO 2 2 2 3 1\nA 2\nR2\nA 3\nR1\nA 5\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7588794397198599, 0.09488538735771047, 0.9904952476238119, 0.9172254111245346 ], "category_id": 1, "smiles": "*ON([1*])[2*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 6.6716 -4.6693 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1602 -6.7165 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6716 -0.6535 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9489 -6.7165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3433 -4.6693 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\nM ISO 2 2 2 3 1\nA 2\nR2\nA 3\nR1\nA 5\nR\nM END\n" } ] } ], "[1,2]-Wittig rearrangement.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.04052026013006503, 0.04103590256666795, 0.09304652326163082, 0.19931724103810147 ], "category_id": 1, "smiles": "[12*]", "molfile": "\n RDKit 2D\n\n 1 0 0 0 0 0 0 0 0 0999 V2000\n 2.1820 -6.1654 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\nM ISO 1 1 12\nA 1\nR12\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.09954977488744372, 0.18173042565238662, 0.2321160580290145, 0.4572572000285857 ], "category_id": 1, "smiles": "*C([H])O[7*]", "molfile": "\n RDKit 2D\n\n 5 4 0 0 0 0 0 0 0 0999 V2000\n 5.0159 -5.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5605 -7.2677 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0159 -1.7559 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 8.3598 -7.2677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8151 -5.3780 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 4 1 0\n 4 5 1 0\nM ISO 1 5 7\nA 2\nR\nA 5\nR7\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.2571285642821411, 0.16267804231786223, 0.4227113556778389, 0.2652677987345321 ], "category_id": 2, "text": [ "deprotonation" ] } 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"conditions": [ { "category": "[Txt]", "bbox": [ 0.40070035017508754, 0.3210280422925518, 0.51975987993997, 0.358732678132281 ], "category_id": 2, "text": [ "retro-aldol" ] }, { "category": "[Txt]", "bbox": [ 0.35167583791895946, 0.3721986195036129, 0.567783891945973, 0.40667142941422246 ], "category_id": 2, "text": [ "cyclobutane cleavage" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.5782891445722862, 0.26878018977178414, 0.7163581790895448, 0.44922380414763113 ], "category_id": 1, "smiles": "[H]O/C1=C/CC(C(=O)OC)C(=O)CCC1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 3.3911 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1085 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6304 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9130 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3913 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3913 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6304 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3911 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 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0 0 0 0 0\n 4.1085 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8693 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6302 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6302 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 12 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 11 2 0\n 9 10 1 0\n 11 12 1 0\nA 2\nCO2Me\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7703851925962981, 0.2714733780460505, 0.9084542271135568, 0.4481465288379246 ], "category_id": 1, "smiles": "COC(=O)C1CCC(=O)CCCC1=O", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.5876 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3184 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7274 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9301 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3986 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3986 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7274 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5876 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3184 0.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9163 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9163 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 11 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 2 0\n 8 10 1 0\n 10 11 1 0\nA 2\nCO2Me\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7703851925962981, 0.2714733780460505, 0.9084542271135568, 0.4481465288379246 ], "category_id": 1, "smiles": "COC(=O)C1CCC(=O)CCCC1=O", "molfile": "\n RDKit 2D\n\n 11 11 0 0 0 0 0 0 0 0999 V2000\n 3.5876 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3184 -7.9764 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7274 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9301 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3986 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3986 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7274 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5876 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3184 0.2126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9163 -2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9163 -4.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 11 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 2 0\n 8 10 1 0\n 10 11 1 0\nA 2\nCO2Me\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.5782891445722862, 0.26878018977178414, 0.7163581790895448, 0.44922380414763113 ], "category_id": 1, "smiles": "[H]O/C1=C/CC(C(=O)OC)C(=O)CCC1", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 3.3911 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1085 -7.8976 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6304 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9130 -7.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3913 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3913 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6304 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3911 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1085 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.8693 0.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6302 -3.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6302 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 1 0\n 1 12 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 9 1 0\n 8 11 2 0\n 9 10 1 0\n 11 12 1 0\nA 2\nCO2Me\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.19409704852426213, 0.5968105215774284, 0.2861430715357679, 0.744935876662079 ], "category_id": 1, "smiles": "O=C1C=C(O)CCC1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 0.4724 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4724 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5722 -2.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5722 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6194 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6194 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6194 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5722 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 8 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.3391695847923962, 0.6264355925943585, 0.44222111055527763, 0.7013062266189637 ], "category_id": 1, "smiles": "C=CC(=O)OC", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 0.9356 -3.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7950 -1.0472 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9356 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\nA 2\nCO2Me\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.527263631815908, 0.5925014203386023, 0.615807903951976, 0.7395495001135463 ], "category_id": 1, "smiles": "O=C1C=C(O)CCC1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 0.4601 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4601 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5050 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5050 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4988 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4988 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4988 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5050 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 8 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.615807903951976, 0.6226651290103857, 0.7173586793396698, 0.6969971253801376 ], "category_id": 1, "smiles": "C=CC(=O)OC", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 0.9308 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8866 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9308 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\nA 2\nCO2Me\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.527263631815908, 0.5925014203386023, 0.615807903951976, 0.7395495001135463 ], "category_id": 1, "smiles": "O=C1C=C(O)CCC1", "molfile": "\n RDKit 2D\n\n 8 8 0 0 0 0 0 0 0 0999 V2000\n 0.4601 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4601 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5050 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5050 -0.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4988 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4988 -5.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4988 -7.9764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5050 -6.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 8 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 2 0\n 6 7 1 0\n 6 8 1 0\nM END\n" }, { "category": "[Mol]", "bbox": [ 0.615807903951976, 0.6226651290103857, 0.7173586793396698, 0.6969971253801376 ], "category_id": 1, "smiles": "C=CC(=O)OC", "molfile": "\n RDKit 2D\n\n 3 2 0 0 0 0 0 0 0 0999 V2000\n 0.9308 -3.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8866 -1.1260 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9308 -8.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\nA 2\nCO2Me\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.7478739369684843, 0.6205105783909726, 0.8594297148574287, 0.658753851885555 ], "category_id": 2, "text": [ "hv, [2 + 2]" ] }, { "category": "[Txt]", "bbox": [ 0.7373686843421711, 0.6716811556020337, 0.8714357178589295, 0.7039994148932301 ], "category_id": 2, "text": [ "cycloaddition" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.14807403701850924, 0.8041860186959392, 0.3266633316658329, 0.9717023293553078 ], "category_id": 1, "smiles": "[H]OC12CCCC(=O)C1C(C(=O)OC)C2.[I-]", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3626 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3626 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0851 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0851 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7168 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7168 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7168 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4393 -8.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0851 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7113 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7113 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0711 -1.7559 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5132 -5.0630 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 9 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 1 0\n 6 9 1 0\n 6 10 1 0\n 7 8 1 0\n 10 11 1 0\n 11 12 1 0\nM CHG 1 13 -1\nA 12\nCO2Me\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.14807403701850924, 0.8041860186959392, 0.3266633316658329, 0.9717023293553078 ], "category_id": 1, "smiles": "[H]OC12CCCC(=O)C1C(C(=O)OC)C2.[I-]", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.3626 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3626 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0851 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0851 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7168 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7168 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7168 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4393 -8.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0851 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7113 -5.0630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7113 -3.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0711 -1.7559 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 11.5132 -5.0630 0.0000 I 0 0 0 0 0 15 0 0 0 0 0 0\n 1 2 1 0\n 1 9 1 0\n 2 3 1 0\n 3 4 2 0\n 3 5 1 0\n 5 6 1 0\n 5 11 1 0\n 6 7 1 0\n 6 9 1 0\n 6 10 1 0\n 7 8 1 0\n 10 11 1 0\n 11 12 1 0\nM CHG 1 13 -1\nA 12\nCO2Me\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.36718359179589793, 0.8461997557744947, 0.4822411205602801, 0.8822884786496641 ], "category_id": 2, "text": [ "retro-aldol" ] }, { "category": "[Txt]", "bbox": [ 0.3151575787893947, 0.8979089706404091, 0.5307653826913457, 0.9313045052413121 ], "category_id": 2, "text": [ "cyclobutane cleavage" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.536768384192096, 0.79610645387314, 0.7128564282141071, 0.9711636917004544 ], "category_id": 1, "smiles": "C=C.[H]O/C1=C/C(C(=O)OC)CC(=O)CCC1", "molfile": "\n RDKit 2D\n\n 14 13 0 0 0 0 0 0 0 0999 V2000\n 5.0547 -4.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6825 -5.7717 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7696 -6.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.9705 -6.3228 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0.8238361475258177, 0.47073536768384194, 0.9614276316240312 ], "category_id": 1, "smiles": "*C1=CC=CC(*)=C1O=CC=C", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 6.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 2 3\n 4 5 1 0\n 5 6 1 0\n 5 11 2 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\nA 7\nR\nA 12\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.32416208104052024, 0.8238361475258177, 0.47073536768384194, 0.9614276316240312 ], "category_id": 1, "smiles": "*C1=CC=CC(*)=C1O=CC=C", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 6.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 -2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5000 2.5981 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 2 3\n 4 5 1 0\n 5 6 1 0\n 5 11 2 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 9 10 2 0\n 10 11 1 0\n 11 12 1 0\nA 7\nR\nA 12\nR\nM END\n" } ], "conditions": [ { "category": "[Txt]", "bbox": [ 0.49524762381190596, 0.8535239366258472, 0.6613306653326664, 0.8883499969162664 ], "category_id": 2, "text": [ "[3,3]-sigmatropic" ] }, { "category": "[Txt]", "bbox": [ 0.5047523761880941, 0.907190324614362, 0.6528264132066033, 0.9368781137143916 ], "category_id": 2, "text": [ "rearrangement" ] } ], "products": [ { "category": "[Mol]", "bbox": [ 0.6768384192096047, 0.8124177671027295, 0.8039019509754878, 0.9854062305125166 ], "category_id": 1, "smiles": "*C1=CC([H])(CC=C)C=C(*)C1=O", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 8.4000 -1.5197 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2835 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2835 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2331 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7780 -7.2677 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2331 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2835 -8.8425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4000 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4472 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4472 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6614 -1.5197 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2331 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2331 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 12 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 9 1 0\n 6 7 1 0\n 7 8 2 0\n 9 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\nA 1\n*\nA 11\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.6768384192096047, 0.8124177671027295, 0.8039019509754878, 0.9854062305125166 ], "category_id": 1, "smiles": "*C1=CC([H])(CC=C)C=C(*)C1=O", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 8.4000 -1.5197 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2835 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2835 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2331 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7780 -7.2677 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2331 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2835 -8.8425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.4000 -7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4472 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4472 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6614 -1.5197 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2331 -1.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2331 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 12 1 0\n 3 4 1 0\n 4 5 1 0\n 4 6 1 0\n 4 9 1 0\n 6 7 1 0\n 7 8 2 0\n 9 10 2 0\n 10 11 1 0\n 10 12 1 0\n 12 13 2 0\nA 1\n*\nA 11\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.8419209604802401, 0.8044249008065677, 0.9694847423711856, 0.9785552022586637 ], "category_id": 1, "smiles": "*c1cc(CC=C)cc(*)c1O", "molfile": "\n RDKit 2D\n\n 12 12 0 0 0 0 0 0 0 0999 V2000\n 7.6704 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9659 -8.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3269 -7.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3269 -5.6929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9659 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9659 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6704 -1.6772 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3269 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3269 0.2913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6224 -2.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9834 -1.6772 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6224 -4.6693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 2 0\n 2 3 1 0\n 3 4 1 0\n 4 5 2 0\n 4 12 1 0\n 5 6 1 0\n 6 7 1 0\n 6 8 2 0\n 8 9 1 0\n 8 10 1 0\n 10 11 1 0\n 10 12 2 0\nA 7\nR\nA 11\nR\nM END\n" } ] } ], "van Leusen oxazole synthesis.png": [ { "reactants": [ { "category": "[Mol]", "bbox": [ 0.02451225612806403, 0.07611216170265712, 0.2576288144072036, 0.3487527409360558 ], "category_id": 1, "smiles": "[H]C(N=[C])S(=O)(=O)c1ccc(C)cc1", "molfile": "\n RDKit 2D\n\n 14 14 0 0 0 0 0 0 0 0999 V2000\n 0.4571 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8952 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3332 -8.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7712 -6.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.7712 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.0569 -2.6220 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4949 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 12.4949 -6.6378 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 14.7805 -2.1496 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 17.0662 -3.5669 0.0000 C 0 0 0 0 0 2 0 0 0 0 0 0\n 8.6855 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4283 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3332 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8952 -3.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 14 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 13 1 0\n 6 7 1 0\n 6 11 2 0\n 6 12 2 0\n 7 8 1 0\n 7 9 1 0\n 9 10 2 0\n 13 14 2 0\nM RAD 1 10 3\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.3626813406703352, 0.07611216170265712, 0.5957978989494748, 0.3419367264552208 ], "category_id": 1, "smiles": "[C]=NCS(=O)(=O)c1ccc(C)cc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.6299 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1496 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6693 -7.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1890 -6.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1890 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7087 -2.5433 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 13.3858 -3.6457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 15.7480 -2.0709 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 18.2677 -3.4094 0.0000 C 0 0 0 0 0 2 0 0 0 0 0 0\n 9.2913 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1260 -0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.6693 -2.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1496 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 13 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 12 1 0\n 6 7 1 0\n 6 10 2 0\n 6 11 2 0\n 7 8 1 0\n 8 9 2 0\n 12 13 2 0\nM RAD 1 9 3\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.3626813406703352, 0.07611216170265712, 0.5957978989494748, 0.3419367264552208 ], "category_id": 1, "smiles": "[C]=NCS(=O)(=O)c1ccc(C)cc1", "molfile": "\n RDKit 2D\n\n 13 13 0 0 0 0 0 0 0 0999 V2000\n 0.6299 -7.9764 0.0000 C 0 0 0 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6.1805 -1.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6932 -4.5118 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0602 -4.9055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 3 2 0\nA 2\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.7173586793396698, 0.08860818825085455, 0.9554777388694348, 0.38396881575370306 ], "category_id": 1, "smiles": "*C(O)C(/N=C\\Cl)S(=O)(=O)c1ccc(C)cc1", "molfile": "\n RDKit 2D\n\n 17 17 0 0 0 0 0 0 0 0999 V2000\n 0.4321 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7364 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0407 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2010 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2010 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3613 -2.3071 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8097 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8260 -1.8346 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.9863 -3.0945 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 17.8585 -4.7480 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8097 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5054 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8260 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6575 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2092 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0407 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7364 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 17 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 16 1 0\n 6 7 1 0\n 6 14 2 0\n 6 15 2 0\n 7 8 1 0\n 7 11 1 0\n 8 9 2 0\n 9 10 1 0\n 11 12 1 0\n 11 13 1 0\n 16 17 2 0\nM RAD 1 9 2\nA 12\nR\nM END\n" } ] }, { "reactants": [ { "category": "[Mol]", "bbox": [ 0.7173586793396698, 0.08860818825085455, 0.9554777388694348, 0.38396881575370306 ], "category_id": 1, "smiles": "*C(O)C(/N=C\\Cl)S(=O)(=O)c1ccc(C)cc1", "molfile": "\n RDKit 2D\n\n 17 17 0 0 0 0 0 0 0 0999 V2000\n 0.4321 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7364 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0407 -7.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2010 -6.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2010 -3.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.3613 -2.3071 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8097 -3.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8260 -1.8346 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 15.9863 -3.0945 0.0000 C 0 0 0 0 0 3 0 0 0 0 0 0\n 17.8585 -4.7480 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n 11.8097 -5.8504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.5054 -7.1890 0.0000 R 0 0 0 0 0 0 0 0 0 0 0 0\n 13.8260 -7.1890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.6575 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.2092 -0.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0407 -2.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7364 -3.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 3 2 0\n 2 17 1 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 5 16 1 0\n 6 7 1 0\n 6 14 2 0\n 6 15 2 0\n 7 8 1 0\n 7 11 1 0\n 8 9 2 0\n 9 10 1 0\n 11 12 1 0\n 11 13 1 0\n 16 17 2 0\nM RAD 1 9 2\nA 12\nR\nM END\n" } ], "conditions": [], "products": [ { "category": "[Mol]", "bbox": [ 0.15957978989494748, 0.6350253491311243, 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