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ligand_id
stringlengths
12
15
raw_mol
unknown
xtb_global_min_mol
unknown
xtb_global_min_energy
float64
-1,858,015.73
-244,584.43
crest_local_min_mol
unknown
crest_local_min_energy
float64
-1,858,014.42
-244,584.7
SMILES
stringlengths
37
352
00G_3FUJ_A_710
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-456,278.146127
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-456,280.830218
[H]c1c(OC([H])([H])C([H])([H])n2c([H])c([H])c([H])c2[H])c([H])c2c([H])c([H])n([H])c2c1[H]
02Z_3RZB_A_458
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-677,769.438203
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-677,769.719462
[H]c1c([H])c([H])c(N([H])C2=[S+]/C(=C(/[O-])N([H])[H])C(N([H])[H])=N2)c([H])c1[H]
03K_4EK5_A_300
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-572,300.591956
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-572,300.972592
[H]c1c([H])c(C(=O)N([H])c2nn([H])c(C3([H])C([H])([H])C3([H])[H])c2[H])c([H])c([H])c1C(=O)N([H])[H]
03X_3U6H_A_1
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102, 85, 28, 193, 22 ]
-1,139,777.719796
null
null
[H]c1nc2c([H])c(OC([H])([H])[H])c(OC([H])([H])[H])c([H])c2c(Oc2c([H])c([H])c(N([H])C(=O)c3c(C([H])([H])[H])n(C([H])([H])[H])n(-c4c([H])c([H])c([H])c([H])c4[H])c3=O)c([H])c2F)c1[H]
03Z_3RAK_A_497
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-1,167,221.592179
null
null
[H]c1c([H])c([H])c(/C([O-])=C2\[S+]=C(N([H])c3c([H])c([H])c(S(=O)(=O)N([H])[H])c([H])c3[H])N=C2N([H])[H])c([H])c1[H]
044_3U6I_A_1
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-1,164,475.751108
null
null
[H]O[C@]([H])(C([H])([H])[H])C([H])([H])n1c(C([H])([H])[H])c(C(=O)N([H])c2c([H])c([H])c(Oc3c([H])c([H])nc4c([H])c(OC([H])([H])[H])c([H])c([H])c34)c(F)c2[H])c(=O)n1-c1c([H])c([H])c([H])c([H])c1[H]
04Z_3RAL_A_499
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-1,239,133.353156
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-1,239,135.419597
[H]c1c([H])c(OC([H])([H])[H])c([H])c(/C([O-])=C2\[S+]=C(N([H])c3c([H])c([H])c(S(=O)(=O)N([H])[H])c([H])c3[H])N=C2N([H])[H])c1[H]
06F_3UVR_A_361
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-1,045,363.954971
null
null
[H]c1c([H])c(N([H])C(=O)N([H])c2c([H])c(C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])nn2-c2c([H])c([H])c(C([H])([H])[H])c([H])c2[H])c([H])c(N([H])c2c([H])c([H])c3c(c2[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C3=O)c1[H]
06R_4UI3_A_2115
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-666,451.152731
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-666,451.810881
[H]c1c([H])c(C(F)(F)F)c([H])c([H])c1-c1nc2c([H])c([H])c([H])c([H])c2c(=O)n1[H]
06Z_3RJC_A_450
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-850,399.560808
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-850,399.753108
[H]c1c([H])c([H])c(C(=O)c2sc(N([H])c3c([H])c([H])c([H])c(F)c3[H])nc2N([H])[H])c([H])c1[H]
07M_3TFQ_D_302
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-869,289.710345
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-869,294.882602
[H]c1nc(C#N)c(C([H])([H])Sc2c3c(c(C#N)c(=O)n2[H])C([H])([H])C([H])([H])OC3([H])[H])c([H])c1[H]
07V_3TXZ_A_402
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-291,799.994676
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-291,800.838019
[H]C([H])=C(C([H])([H])[H])[C@@]1([H])C([H])([H])C(=O)C(C([H])([H])[H])=C([H])C1([H])[H]
085_3TZM_A_1
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-811,738.30232
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-811,738.797587
[H]c1nc(-c2nc(-c3c([H])c([H])c(C(=O)N([H])[H])c([H])c3[H])n([H])c2-c2c([H])c([H])c3c(c2[H])OC([H])([H])O3)c([H])c([H])c1[H]
08C_4BU9_B_2165
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-526,726.6591
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-526,726.892125
[H]c1c([H])c(-c2nc3c([H])c([H])c([H])c([H])c3c(=O)n2[H])c([H])c([H])c1OC([H])([H])[H]
08W_3UA8_A_264
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-1,244,323.522059
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-1,244,330.382599
[H]c1c(-n2c([H])nc(C(=O)N([H])C([H])([H])[H])c2[H])c(C(F)(F)F)c([H])c2c1c(=O)n(N([H])S(=O)(=O)C([H])([H])[H])c(=O)n2[H]
08Z_3RK7_A_467
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-904,098.757834
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-904,099.347553
[H]c1nc([H])c(/C([O-])=C2\[S+]=C(N([H])c3c([H])c([H])c(C(=O)N([H])[H])c([H])c3[H])N=C2N([H])[H])c([H])c1[H]
09K_4FKI_A_301
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-749,913.830692
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-749,915.077267
[H]c1c([H])c(C([H])([H])C(=O)N([H])c2nn([H])c(C3([H])C([H])([H])C3([H])[H])c2[H])c([H])c([H])c1OC(F)(F)F
09L_4TKG_C_1202
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-924,917.521665
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-924,925.347357
[H]c1c([H])c(C([H])([H])c2nn([H])c(=O)c3c([H])c([H])c([H])c([H])c23)c([H])c(C(=O)N2C([H])([H])C([H])([H])N(C(=O)C3([H])C([H])([H])C3([H])[H])C([H])([H])C2([H])[H])c1F
09L_4TVJ_B_601
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-924,922.065021
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-924,925.342155
[H]c1c([H])c(C([H])([H])c2nn([H])c(=O)c3c([H])c([H])c([H])c([H])c23)c([H])c(C(=O)N2C([H])([H])C([H])([H])N(C(=O)C3([H])C([H])([H])C3([H])[H])C([H])([H])C2([H])[H])c1F
09Z_3RK9_A_483
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-727,126.542727
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-727,127.195056
[H]c1nc([H])c(/C([O-])=C2\[S+]=C(N([H])C([H])(C([H])([H])[H])C([H])([H])[H])N=C2N([H])[H])c([H])c1[H]
0A1_3QTC_A_811
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-420,277.075433
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-420,277.075351
[H]c1c([H])c(C([H])([H])[C@@]([H])(C(=O)[O-])[N+]([H])([H])[H])c([H])c([H])c1OC([H])([H])[H]
0A9_3QGO_A_407
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-373,060.841832
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-373,062.603349
[H]c1c([H])c([H])c(C([H])([H])[C@@]([H])(C(=O)OC([H])([H])[H])N([H])[H])c([H])c1[H]
0B1_3VV7_A_509
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-708,065.188258
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-708,070.988661
[H]c1c([H])c(OC([H])([H])[H])c([H])c(-c2c([H])c([H])c([H])c([C@]3([H])C([H])([H])[C@]3([H])c3nc(N([H])[H])n(C([H])([H])[H])c(=O)c3[H])c2[H])c1[H]
0CE_3L8P_A_2207
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-912,596.06624
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-912,600.74022
[H]C1=NC(=O)c2c3c(c4c(c21)c1c([H])c([C@@]2([H])OC([H])([H])C([H])([H])C([H])([H])C2([H])[H])c([H])c([H])c1n4C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])c1nn(C([H])([H])[H])c([H])c1-3
0CK_3UZP_B_295
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-696,838.783406
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-696,839.644751
[H]c1nc(N([H])[H])nc(-c2c(-c3c([H])c([H])c(F)c([H])c3[H])nc([H])n2C2([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C2([H])[H])c1[H]
0CO_3CS6_A_1
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186, 205, 65, 227, 37, 14, 66, 193, 202, 121, 64, 168, 198, 205, 65, 229, 80, 0, 66, 123, 20, 162, 64, 152, 110, 216, 65, 172, 28, 1, 66, 186, 73, 180, 64, 92, 143, 203, 65, 51, 51, 254, 65, 145, 237, 140, 64, 51, 51, 218, 65, 207, 119, 10, 66, 219, 249, 110, 64, 166, 155, 191, 65, 18, 131, 6, 66, 102, 102, 174, 64, 59, 223, 187, 65, 119, 62, 6, 66, 211, 77, 150, 64, 147, 24, 191, 65, 244, 125, 12, 66, 96, 229, 30, 65, 4, 86, 186, 65, 47, 93, 4, 66, 2, 43, 53, 65, 250, 126, 177, 65, 188, 244, 3, 66, 238, 124, 43, 65, 57, 180, 181, 65, 223, 79, 10, 66, 45, 178, 15, 65, 150, 67, 223, 65, 135, 150, 11, 66, 35, 219, 35, 65, 221, 36, 219, 65, 14, 45, 16, 66, 27, 47, 43, 65, 123, 20, 225, 65, 207, 247, 9, 66, 22 ]
null
null
null
null
[H]OC(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[C@@]1([H])C([H])([H])O[C@](C([H])([H])[H])([C@@]2([H])C([H])([H])C([H])([H])[C@@]3([H])/C(=C([H])/C([H])=C4\C(=C([H])[H])[C@@]([H])(O[H])C([H])([H])[C@]([H])(O[H])C4([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]23C([H])([H])[H])C1([H])[H]
0DF_3UWK_B_801
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-465,644.546925
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-465,645.703564
[H]c1nc2c(c([H])c1-c1c([H])c([H])c([H])c([H])c1[H])n(C([H])([H])[H])c(=O)n2[H]
0DJ_3UWO_A_800
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-571,587.806598
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-571,588.584171
[H]c1nc2c(c([H])c1-c1c([H])c([H])c([H])c(C(=O)N([H])[H])c1[H])n(C([H])([H])[H])c(=O)n2[H]
0DN_3UXM_D_803
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-564,622.793685
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-564,622.90386
[H]O[C@@]1([H])C([H])([H])[C@]([H])(n2c([H])c(C([H])([H])[H])c(=O)n([H])c2=O)O[C@]1([H])C([H])([H])F
0E0_5C5P_B_1202
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-566,154.160951
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-566,156.405477
[H]OC([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])OC([H])([H])c2c(n([H])c(=O)c3c([H])c([H])c([H])c([H])c23)C1([H])[H]
0E1_5C5R_A_1202
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-455,675.140449
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-455,675.206047
[H]c1c2c(n([H])c(=O)c1C#N)C([H])([H])[C@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])OC2([H])[H]
0F5_3VBQ_A_555
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-1,003,595.85422
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-1,003,598.267853
[H]c1nc([H])c(N([H])[C@]2([H])C([H])([H])C([H])([H])[C@@]([H])([N+]([H])([H])[H])C([H])([H])C2([H])[H])nc1-c1c([H])c([H])c([H])c(C([H])([H])[C@@]2([H])SC([O-])=NC2=O)c1[H]
0FK_3VBV_A_1
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-405,561.881914
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-405,576.993221
[H]Oc1c([H])c([H])c([H])c2c([H])c([H])c(C(=O)N([H])[H])nc12
0G1_3V5L_A_701
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-1,055,197.634622
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-1,055,200.404686
[H]OC(c1c([H])c([H])c2c(-c3c([H])c([H])c(OC([H])([H])[H])c([H])c3[H])c(-c3nn([H])c4c([H])c([H])sc34)n([H])c2c1[H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])[H]
0G2_3V8W_A_701
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-983,284.59393
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-983,287.958711
[H]OC(c1c([H])c([H])c2c([H])c(-c3nn([H])c4c([H])c(-c5c([H])c([H])c([H])c([H])c5[H])sc34)n([H])c2c1[H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])[H]
0H5_3VEY_A_504
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-535,123.261305
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-535,124.287977
[H]c1nc(N([H])c2nn(C([H])([H])[H])c([H])c2[H])c2c([H])c(OC([H])([H])[H])c([H])c([H])c2n1
0H9_4FPE_A_701
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-718,154.508914
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-718,175.498375
[H]c1c([H])c(C([H])([H])[N+]([H])([H])C([H])([H])C([H])([H])S(=O)(=O)[O-])c([H])c([H])c1OC([H])([H])[H]
0HD_3V8S_A_501
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-573,687.18364
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-573,692.177356
[H]c1c([H])c([H])c(C([H])([H])C([H])([H])N([H])C(=O)N([H])c2c([H])c([H])c3c(c([H])nn3[H])c2[H])c([H])c1[H]
0HY_4D8A_A_305
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-629,009.676928
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-629,011.337621
[H]N([H])c1nc2c(c(=O)c([C@]([H])(C([H])([H])[H])C([H])([H])C(=O)OC([H])([H])[H])nn2[H])c(=O)n1[H]
0J9_4GKH_L_302
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-633,765.233637
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-633,766.680089
[H]c1nc(N([H])[H])c2c(-c3c([H])c([H])c([H])c4c([H])c([H])c([H])c([H])c34)nn(C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])c2n1
0J9_4K11_A_601
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-633,766.332903
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-633,766.6844
[H]c1nc(N([H])[H])c2c(-c3c([H])c([H])c([H])c4c([H])c([H])c([H])c([H])c34)nn(C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])c2n1
0JF_4DCE_A_1501
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-1,019,409.478402
null
null
[H]c1nc(N([H])c2c([H])c(OC([H])([H])[H])c(OC([H])([H])[H])c(OC([H])([H])[H])c2[H])nc(N2C([H])([H])C([H])([H])C([H])([H])[C@]([H])(C(=O)N([H])C([H])([H])c3c([H])c([H])c(C([H])([H])[H])c([H])c3[H])C2([H])[H])c1[H]
0JJ_4DEG_A_1401
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-1,032,865.541603
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-1,032,866.97516
[H]c1nc2c([H])c(OC([H])([H])[H])c([H])nc2c(N([H])C([H])([H])c2nnc3c([H])c([H])c(-c4snc(C([H])([H])[H])c4[H])nn23)c1[H]
0JK_4DEH_A_1401
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-728,076.455271
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-728,077.118924
[H]c1nc2c([H])c([H])c(C([H])([H])n3nnc4c3C(=O)N(c3c([H])c([H])c([H])c([H])c3[H])C([H])([H])C4([H])[H])c([H])c2c([H])c1[H]
0JN_4GKI_I_302
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-658,452.704836
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-658,453.321329
[H]c1nc(N([H])[H])c2c(C([H])([H])c3c([H])c([H])c([H])c4c([H])c([H])c([H])c([H])c34)nn(C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])c2n1
0KF_3VO3_A_2001
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-916,736.038932
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-916,735.142362
[H]c1c([H])c(Oc2nn3c([H])c(N([H])C(=O)C4([H])C([H])([H])C4([H])[H])nc3c([H])c2[H])c([H])c(N([H])C(=O)c2c([H])c(C([H])([H])[H])nn2C([H])([H])[H])c1[H]
0N5_4E1K_A_505
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-812,494.986965
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-812,500.881775
[H]Oc1c(OC([H])([H])[H])c([H])c2c(N([H])c3c([H])c([H])c(N([H])C(=O)c4c([H])c([H])c([H])c([H])c4[H])c([H])c3[H])nc([H])nc2c1[H]
0NH_4E4L_A_1201
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-882,411.44326
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-882,411.972163
[H]c1nc2c(c([H])c([H])n2[H])c2c1nc([H])n2C1(C([H])([H])[H])C([H])([H])C([H])([H])N(S(=O)(=O)C([H])([H])[H])C([H])([H])C1([H])[H]
0NH_4E4M_E_1201
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-882,411.511721
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-882,411.965792
[H]c1nc2c(c([H])c([H])n2[H])c2c1nc([H])n2C1(C([H])([H])[H])C([H])([H])C([H])([H])N(S(=O)(=O)C([H])([H])[H])C([H])([H])C1([H])[H]
0NJ_4E5D_A_601
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-733,003.850343
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-733,004.591128
[H]c1c([H])c([H])c(-c2nc3c([H])c([H])c(OC([H])([H])[H])c([H])c3s2)c(F)c1[H]
0NL_4E4N_B_1201
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-705,830.716812
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-705,834.571267
[H]c1nc2c(c([H])c([H])n2[H])c2c1nc([H])n2[C@]1([H])C([H])([H])C([H])([H])[C@@]([H])(N([H])C(=O)OC(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1([H])[H]
0NS_4E96_A_201
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-931,293.634702
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-931,293.572289
[H]c1c([H])c([H])c(S(=O)(=O)N([H])c2c([H])c([H])c3c(c2[H])C([H])([H])N(C([H])([H])[H])C(=O)N3[H])c(OC([H])([H])[H])c1[H]
0NU_4E6D_B_1201
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-642,448.930046
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-642,453.758411
[H]c1nc2c(c([H])c([H])n2[H])c2c1nc([H])n2[C@@]1([H])C([H])([H])N(C(=O)C([H])([H])C#N)C([H])([H])C([H])([H])C1([H])[H]
0NX_3VQ4_A_305
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-371,509.009036
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-371,510.973746
[H]OC([H])([H])c1noc(-c2c([H])c([H])c([H])c([H])c2[H])c1[H]
0O4_4EE0_A_202
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-732,742.412183
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-732,756.28975
[H]c1nc(-c2c([H])c([H])c(C(=O)N([H])C([H])([H])C([H])([H])N3C([H])([H])C([H])([H])OC([H])([H])C3([H])[H])c([H])c2[H])c2c([H])c([H])c([H])c([H])c2c1[H]
0O5_4EDZ_D_202
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-757,445.911036
[H]c1c([H])c(-c2nc(C([H])([H])[H])c([H])c3c([H])c([H])c([H])c([H])c23)c([H])c([H])c1C(=O)N([H])C([H])([H])C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H]
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LigBoundConf 2.0

LigBoundConf is a set of high-quality drug-like bound ligand structures in the Protein Data Bank (PDB). The original set contains three sets of structures: "raw” structures taken directly from the PDB, "bound” structures, obtained by performing a local minimization of the ligand in the presence of the protein pocket with an empirical force field, and “global minimum” structures, obtained by finding the lowest energy conformation of the ligand with an empirical force field and implicit water solvation model.

LigBoundConf 2.0 is a neutral subset of LigBoundConf in which we have recalculated the "bound" and "global minimum" structures in vaccuo without an implicit solvent. To obtain the "bound” structures we sought to relieve any artificial high-energy artifacts from the deposited PDB structures. We did this by running a local minimization with the semi-empirical quantum chemistry method GFN2-xTB using the “crude” convergence criteria. This ensured that artifacts were removed without significantly altering the bound pose of the ligand. We then performed single point energy (SPE) density fucntional theory (DFT) calculations at the ωB97M-D3(BJ)/def2-TZVPPD level of theory.

To obtain the "global minimum” structures, we used the CREST enumeration method with 50 conformers, which uses the same GFN2-xTB energy function to search for low energy gas phase structures. We took the lowest energy structure as the ``global minimum” conformation and performed a SPE DFT calculation at the same ωB97M-D3(BJ)/def2-TZVPPD level of theory.

The LigBoundConf 2.0 neutral dataset ended up with 3132 ligands.

This dataset is used to validate the StrainRelief method presented here [pre-print] [code].

Datasets

  • SMILES.csv (mapping from ligand ids to SMILE strings)
  • ligboundconf_2_raw.sdf
  • ligboundconf_2_crest_local_min.sdf
  • ligboundconf_2_xtb_global_min.sdf
  • ligboundconf_2_molecules_and_energies.parquet (all structures for the sdfs above as RDKit.Mol binary objects with their corresponding DFT energies)
  • strain_releif_output_mace_from_ligboundconf_xtb.parquet (the output from the StrainRelief tool when run on the xtb structures)

license: apache-2.0

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