[Supporting Information]
Role of Breast Cancer Resistance Protein (BCRP) as Active Efflux Transporter on Blood-Brain Barrier (BBB) Permeability
Prabha Garg*, Rahul Dhakne, Vilas Belekar
Department of Pharmacoinformatics, National Institute of Pharmaceutical Education and Research (NIPER), Sector-67, S.A.S. Nagar, Punjab-160062, India
* Corresponding author: Tel: +91 1722292016
E-mail:
Table S1.Y-Scrambling Test Result
No. of Permutation / Models / Sensitivity / Specificity / Accuracy1 / Training / 0.92 / 0.73 / 0.86
Test / 0.70 / 0.21 / 0.52
2 / Training / 0.82 / 0.30 / 0.64
Test / 0.61 / 0.7 / 0.42
3 / Training / 0.80 / 0.38 / 0.66
Test / 0.73 / 0.14 / 0.52
4 / Training / 0.71 / 0.23 / 0.55
Test / 0.73 / 0 / 0.48
5 / Training / 0.76 / 0.23 / 0.58
Test / 0.92 / 0.29 / 0.70
Table S2. The detail information of BCRP Substrates and non-substrates molecules (n=249).
Comp. Id / Simile notation of compounds / Actual / Predicted / Dataset / Leverage Valuess1 / c1ccc(OC)c(c12)C(=O)c3c(C2=O)c(O)c4c(c3O)[C@@H](C[C@](C4)(O)C(=O)C)O[C@@H]5C[C@H](N)[C@@H](O)[C@@H](O5)C / 1 / 1 / Test / 0.017603
s2 / c1ccc(OC)c(c12)C(=O)c3c(C2=O)c(O)c4c(c3O)[C@H](C[C@@](C4)(O)C(=O)CO)O[C@H]5C[C@@H](N)[C@H](O)[C@H](O5)C / 1 / 1 / Training / 0.013262
s3 / N[C@@H](C1)[C@@H](O)[C@H](C)O[C@H]1O[C@H]2C[C@](O)(C(=O)CO)Cc(c23)c(O)c4c(c3O)C(=O)c5c(C4=O)cccc5OC / 1 / 1 / Training / 0.040368
s4 / OCCNCCNc1ccc(NCCNCCO)c(c12)C(=O)c3c(C2=O)c(O)ccc3O / 1 / 1 / Training / 0.018663
s5 / N1CCN=C1N/N=C\c2c(cccc3)c3c(c(c24)cccc4)/C=N\NC5=NCCN5 / 1 / 1 / Training / 0.468251
s6 / C1OC(=O)[C@](O)(CC)c(c12)cc-3n(c2=O)Cc4c3nc5c(c4)c(c(O)cc5)CN(C)C / 1 / 1 / Training / 0.010225
s7 / c1c(O)ccc(n2)c1c(CC)c(c2-3)Cn4c3cc5c(c4=O)COC(=O)[C@@]5(O)CC / 1 / 1 / Training / 0.014483
s8 / C1OC(=O)[C@](O)(CC)c(c12)cc-3n(c2=O)Cc4c3nc5c(c4)c(N)ccc5 / 1 / 1 / Training / 0.006494
s9 / Nc1nc(N)nc(c12)ncc(n2)CN(C)c3ccc(cc3)C(=O)N[C@@H](C(=O)O)CCC(=O)O / 1 / 1 / Training / 0.064149
s10 / n1c(N)nc(N)c(c12)nc(c(n2)C)CN(C)c3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](C(=O)O)CCC(=O)O / 1 / 1 / Training / 0.061584
s11 / n1c(N)nc(N)c(c12)nc(c(n2)C)CN(C)c3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@H](C(=O)O)CCC(=O)O / 1 / 1 / Training / 0.054314
s12 / COc(c1)c(OC)cc(c12)nc(nc2N)N3CCN(CC3)C(=O)c4ccco4 / 1 / 1 / Training / 0.010344
s13 / OCC1OC(C(O)C(O)C1O)N2C3C(Nc4c5ccc(c4)O)C5=C(C(=O)N(C6=O)NC(CO)CO)C6=C3c(c27)ccc(c7)O / 1 / 1 / Training / 0.009325
s14 / OC1C(O)C(O)C(CO)OC1n2c(cc(O)cc3)c3c(c24)c5c(C(=O)N(C5=O)NC(CO)CO)c6c4[nH]c7c6ccc(O)c7 / 1 / 1 / Training / 0.011308
s15 / CN1CC[C@H]([C@@H](O)C1)c(c(O)cc2O)c(c23)oc(cc3=O)-c4ccccc4Cl / 1 / 1 / Training / 0.016688
s16 / C1COCCN1CCCOc(c(c2)NC(=O)C=C)cc(c23)ncnc3Nc4cc(Cl)c(F)cc4 / 1 / 1 / Test / 0.021251
s17 / C1=CC(N)=C[C@H](C1=2)Oc3c(ccc(c3)N)C2c4c(C(=O)OC)cccc4 / 1 / 1 / Training / 0.013173
S18 / Cc1cc(C)c(n12)C=[C]3=[N+]([B]2(F)F)=C(C=C3)CCC(=O)NCCN(C)C / 1 / 1 / Remove / 0.07525
s19 / CN1CCN(CC1)c(cc2)nc(c23)nc([nH]3)-c(cc4)cc(c45)[nH]c(n5)-c6ccccc6 / 1 / 1 / Training / 0.0719
s20 / O=S(=O)(O)Oc(cc1)cc(CC2)c1[C@H](CC3)[C@H]2[C@@H]([C@@]34C)CCC4=O / 1 / 1 / Training / 0.005935
s21 / o1c(=O)cc(C)c(c12)ccc(c2)OS(=O)(=O)O / 1 / 1 / Test / 0.184029
s22 / Cc1cc(=O)oc(c12)cc(cc2)O[C@H]3O[C@H](C(=O)O)[C@@H](O)[C@@H](O)[C@H]3O / 1 / 1 / Training / 0.010028
s23 / O[N@H+](=O)c(cc1)cc([N@@H+](=O)O)c1SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@H]([NH4+])C(=O)O / 1 / 1 / Training / 0.005857
s24 / c1ccncc1Cc2c(C)c(O)c(C)c(c23)sc(n3)NC / 1 / 1 / Training / 0.009477
s25 / O[C@@H]1[C@H](O)[C@H](C(=O)O)O[C@H]([C@H]1O)Oc(c(C)c(c23)sc(n3)NC)c(C)c2Cc4cccnc4 / 1 / 1 / Test / 0.006766
s26 / O=S(=O)(O)O[C@@H](CC1)C[C@H]([C@@]12C)CC[C@@H]3[C@@H]2CC[C@]4(C)[C@@H]3CC[C@H]4[C@@H](C)CCC(=O)NCCS(=O)(=O)O / 1 / 1 / Training / 0.080133
s27 / COC(=O)[C@H]1C(=O)c(c2c13)c(C)c([nH]2)cc4c(CC)c(C=O)c(n4)cc5[nH]c(c(C)c5C=C)cc6nc3[C@H]([C@@H]6C)CCC(=O)OCC / 1 / 1 / Training / 0.172916
S28 / O=C(O)CCc1c(C)c(nc12)cc3[nH]c(c(c3C)C=C)cc4nc(c(c4C)C=C)cc5[nH]c(c2)c(c5C)CCC(=O)O / 1 / 0 / Remove / 0.084858
s29 / c1c(O)cc(O)c(c12)c(=O)c(co2)-c3ccc(O)cc3 / 1 / 1 / Test / 0.009382
S30 / FC(F)(F)c(n1)cc(n1C)C(=O)Cc2ccc(cc2)S(=O)(=O)N3CCCC3 / 0 / 0 / Remove / 0.567066
s31 / COc1cc(cc(OC)c1O)C2c(cc3c(c4)OCO3)c4C(C(C25)COC5=O)OC(O6)C(O)C(O)C(C67)OC(C)OC7 / 1 / 1 / Training / 0.037743
s32 / CO[C@H](C1(C)C)[C@@H](OC(=O)N)[C@H](O)[C@@H](O1)Oc(c2C)ccc(c23)c(O)c(c(=O)o3)NC(=O)c4ccc(O)c(c4)CC=C(C)C / 1 / 1 / Training / 0.126718
S33 / O[C@H](C)c1c(C)c(nc12)cc3[nH]c(c(c3C)CCC(=O)O)cc4nc(cc5c([C@@H](O)C)c(C)c([nH]5)c2)c(C)c4CCC(=O)O / 0 / 0 / Remove / 0.057903
s34 / Oc(c1)cc(O)c(c12)c(=O)c(O)c(o2)-c3ccc(O)c(O)c3 / 1 / 1 / Test / 0.006184
s35 / F[C@]12[C@H](O)C[C@](C)([C@](O)([C@H](C)C3)C(=O)CO)[C@H]3[C@@H]1CCC([C@@]24C)=CC(=O)C=C4 / 0 / 0 / Training / 0.501446
s36 / C1CC(=O)C=C([C@@]12C)CC[C@@H]3[C@@H]4[C@](C=O)(C[C@H](O)[C@H]23)[C@@H](CC4)C(=O)CO / 0 / 0 / Training / 0.054375
s37 / C1CC(=O)C=C([C@@]12C)CC[C@H]3[C@H]2[C@H](O)C[C@@]4(C=O)[C@H]3CC[C@H]4C(=O)CO / 0 / 0 / Training / 0.047555
s38 / C1OC(=O)C=C1C2CCC(O)(C23C)C4C(CC3O)C5(C)C(CC4)CC(CC5)OC6CC(O)C(C(O6)C)OC7CC(O)C(C(O7)C)OC8CC(O)C(O)C(O8)C / 0 / 0 / Training / 0.049541
s39 / C1CC=C(OC)C(=N2)C=1C(=O)c(c23)cccc3C(=O)Nc4ccc(cc4)CCN(C5)CCc(c56)cc(OC)c(c6)OC / 0 / 0 / Training / 0.06284
s40 / c1cccc(c12)nc-3c(c2CC)Cn4c3cc5c(c4=O)COC(=O)[C@@]5(O)CC / 0 / 0 / Test / 0.014931
s41 / c1cc(C)cc(c12)c(CC)c3c(n2)-c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Training / 0.010775
s42 / c1cc(Br)cc(c12)c(CC)c3c(n2)-c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Training / 0.011061
s43 / c1cc(Cl)cc(c12)c(CC)c3c(n2)-c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Training / 0.161651
s44 / c1c(Br)ccc(c12)c(CC)c3c(n2)-c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Test / 0.014504
s45 / c1c(Cl)ccc(c12)c(CC)c3c(n2)-c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Training / 0.163482
s46 / c1c(F)ccc(c12)c(CC)c3c(n2)-c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Training / 0.016094
s47 / c1c(O)ccc(c12)c(CC)c3c(n2)-c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Training / 0.016268
s48 / c1c(Cl)c(Cl)cc(c12)c(CC)c3c(n2)c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Training / 0.680862
s49 / c1cc(N)cc(c12)c(CC)c3c(n2)-c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 1 / 0 / Training / 0.014578
s50 / c1c(F)c(OC)cc(c12)c(CC)c3c(n2)c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Training / 0.515327
s51 / c1c(F)c(O)cc(c12)c(CC)c3c(n2)c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Test / 0.514551
s52 / c1c(F)c(C)cc(c12)c(CC)c3c(n2)c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Training / 0.012119
s53 / c1c(F)c(F)cc(c12)c(CC)c3c(n2)c4n(C3)c(=O)c5c(c4)[C@@](O)(CC)C(=O)OC5 / 0 / 0 / Training / 0.018812
s54 / C1COCCC1CCCOc(c2)c(OC)cc(c23)ncnc3Nc4ccc(F)c(Cl)c4 / 1 / 1 / Test / 0.020721
s55 / O1COc(c12)cc3c(c2)c(C4CCC4)c5c(n3)-c6n(C5)c(=O)c7c(c6)C(O)(C(=O)C7)CC / 0 / 0 / Training / 0.035026
s56 / Fc1cccc(F)c1C(=O)n2c(N)nc(n2)Nc3ccc(cc3)S(=O)(=O)N / 1 / 1 / Training / 0.018627
s57 / CCC(O)(CC12)CN(C1)CCc3c([nH]c4c3cccc4)C(C2)(C(=O)OC)c(c5)c(OC)cc(c5C678)N(C)C6C(O)(C(=O)OC)C(OC(=O)C)C9(CC)C8N(CC7)CC=C9 / 0 / 0 / Training / 0.498921
s58 / c1ccccc1C(=O)NC(c2ccccc2)C(O)C(=O)OC(C3)C(C)=C(C(C)(C)C34O)C(OC(=O)C)C(=O)C5(C)C(C6(OC(=O)C)C(OC6)CC5O)C4OC(=O)c7ccccc7 / 0 / 0 / Training / 0.276583
s59 / c1ccncc1-c2ccnc(n2)Nc3cc(ccc3C)NC(=O)c4ccc(cc4)CN5CCN(C)CC5 / 1 / 1 / Training / 0.034937
s60 / CC#CC(=O)Nc(c1)ccc(c12)ncnc2Nc3cccc(Br)c3 / 1 / 1 / Training / 0.027073
s61 / Cc1[nH]cnc1CSCCN/C(=N\C)NC#N / 1 / 1 / Training / 0.007929
s62 / CC[C@@H](C)C(=O)O[C@H]1C[C@@H](O)C=C([C@H]12)C=C[C@@H](C)[C@@H]2CC[C@H](O)C[C@@H](O)CC(=O)O / 1 / 1 / Training / 0.018484
s63 / O=C(C)[C@@H]1CC[C@H]([C@]12C)[C@@H]3[C@H](CC2)[C@]4(C)C(CC3)=CC(=O)CC4 / 1 / 1 / Training / 0.065196
s64 / O[C@H]1CC[C@H]([C@]12C)[C@@H]3[C@H](CC2)[C@]4(C)C(CC3)=CC(=O)CC4 / 1 / 1 / Test / 0.030337
s65 / O[C@H]1CC[C@H]([C@@]12C)[C@H]3[C@H](CC2)c4c(CC3)cc(O)cc4 / 1 / 1 / Training / 0.006721
s66 / C1C(N)=CC=C(C1=2)c3c(cc(N)cc3)N(CC)C2c4ccccc4 / 1 / 1 / Training / 0.005373
s67 / n1cn(C)c(c12)c(=O)n(c(=O)n2C)CCCCC(=O)C / 0 / 0 / Training / 0.024006
s68 / Cn1cnc(c12)n(C)c(=O)n(c2=O)CCCC[C@H](C)O / 0 / 0 / Test / 0.020042
s69 / Cn1cnc(c12)n(C)c(=O)n(c2=O)CCCCC(=O)O / 0 / 0 / Test / 0.024417
s70 / Cn1cnc(c12)n(C)c(=O)n(c2=O)CCCC(=O)O / 0 / 0 / Training / 0.036563
s71 / c1cc(OC)cc(c12)[nH]c3c2C[C@H]4N([C@@H]3C=C(C)C)C(=O)[C@H]5N(C4=O)CCC5 / 0 / 0 / Test / 0.580517
s72 / CCC1(O)C(=O)OCc(c12)c(=O)n3c(c2)c4c(C3)c(CN5CCN(C)CC5)c6c(n4)cc7c(c6)OCCO7 / 1 / 1 / Test / 0.003456
s73 / O[C@@H]1CC[C@@H]([C@]12C)[C@H]3[C@H](CC2)c4c(CC3)cc(O)cc4 / 1 / 1 / Training / 0.015117
s74 / Cn1c(N)nc(c12)ncc(c2)-c3ccccc3 / 1 / 1 / Training / 0.018193
s75 / C1[C@@H](O)[C@@H](CO)O[C@H]1n2cnc(c23)c(N)nc(n3)Cl / 1 / 1 / Training / 0.037615
s76 / COc1ccc(cc1)C[C@H](N)C(=O)N[C@H]2[C@H](CO)O[C@H]([C@@H]2O)n(cn3)c(c34)ncnc4N(C)C / 1 / 1 / Training / 0.019469
s77 / CC(=O)OCOC(=O)c(cc1)cc(C(O2)=O)c1C23c4c(cc(OCOC(=O)C)c(c4)CCC(=O)OCOC(=O)C)Oc5c3cc(c(c5)OCOC(=O)C)CCC(=O)OCOC(=O)C / 1 / 1 / Training / 0.049513
s78 / CCC1(O)C(=O)OCc(c2=O)c1cc3n2Cc(c-34)c(CC)c5c(n4)ccc(c5)OC(=O)N6CCC(CC6)N7CCCCC7 / 1 / 1 / Training / 0.008562
S79 / CC[C@@]1(O)C(=O)OCc(c2=O)c1cc(n23)-c4c(C3)c(CC)c5c(n4)ccc(O)c5 / 1 / 1 / Remove / 0.014155
s80 / n1cnc(N)c(c12)ncn2CCOCP(=O)(O)O / 1 / 1 / Training / 0.031074
s81 / C1CC(=O)c(c(=O)o2)c1c(c(c3)OC)c2c(c34)[C@H]5[C@@H](O4)OC=C5 / 1 / 1 / Training / 0.007545
s82 / CCOC(=O)C1=C(C)NC(C)=C([C@@H]1c2c(C(F)(F)F)cccc2)C(=O)OCCNC(=O)c3ccc(cc3)NNN / 1 / 1 / Training / 0.015676
s83 / c12c3c4ccc1c5c(cccc5)cc2ccc3ccc4 / 1 / 1 / Training / 0.023317
s84 / OCCN(CCO)c(n1)nc(N2CCCCC2)c(c13)nc(N(CCO)CCO)nc3N4CCCCC4 / 1 / 1 / Test / 0.048697
s85 / C1CC1n2cc(C(=O)O)c(=O)c(c23)cc(F)c(c3)N4CCN(CC)CC4 / 1 / 1 / Training / 0.011512
s86 / O=C(O)C(C)(C)c1ccc(cc1)[C@@H](O)CCCN2CCC(CC2)C(O)(c3ccccc3)c4ccccc4 / 1 / 0 / Test / 0.022737
s87 / [nH]1c(N)nc(=O)c(c12)nc(cn2)CNc3ccc(cc3)C(=O)N[C@H](C(=O)O)CCC(=O)O / 1 / 1 / Training / 0.046257
S88 / Clc(c1)ccc(OC)c1C(=O)NCCc(cc2)ccc2S(=O)(=O)NC(=O)NC3CCCCC3 / 1 / 0 / Remove / 0.089683
s89 / C1CC1n2cc(C(=O)O)c(=O)c(c23)c(C)c(F)c(c3)N4CCN[C@@H](C4)C / 1 / 1 / Training / 0.001783
s90 / Nc1nc(=O)n(cc1)[C@H]2CS[C@@H](O2)CO / 1 / 1 / Training / 0.010065
S91 / [O-][N+](=O)=[c](cc1)oc1C=NN2C(=O)NC(=O)C2 / 1 / 1 / Remove / 0.008812
s92 / C1CN(C)CCN1c(c(c2n34)OC[C@H]3C)c(F)cc2c(=O)c(c4)C(=O)O / 1 / 1 / Training / 0.053356
s93 / CCCN(CCC)S(=O)(=O)c1ccc(cc1)C(=O)O / 1 / 1 / Test / 0.008517
s94 / n1c(=O)[nH]c(=O)c(-c12)nc3c(cc(C)c(c3)C)n2C[C@@H](O)[C@H](O)[C@@H](O)CO / 1 / 1 / Training / 0.031811
s95 / c1cc(O)c(C(=O)O)cc1/N=N/c2ccc(cc2)S(=O)(=O)Nc3ncccc3 / 1 / 1 / Training / 0.023803
s96 / O=C1C=C(C)C(=O)c(c12)cccc2 / 1 / 1 / Test / 0.007629
s97 / c1ccccc1[S@@](=O)c(c2)ccc(c23)nc([nH]3)NC(=O)OC / 1 / 1 / Training / 0.021619
s98 / COc1cc(cc(OC)c1O)C2c(cc3c(c4)OCO3)c4C(C(C25)COC5=O)OC(O6)C(O)C(O)C(C67)OC(OC7)c8cccs8 / 1 / 1 / Training / 0.015644
s99 / CC[C@@]1(O)C(=O)OCc(c2=O)c1cc(n23)c4c(C3)c(c5c(n4)cccc5)/C=N/OCc6ccc(N)cc6 / 1 / 1 / Training / 0.10869
s100 / CC[C@]1(O)C(=O)OC[C@H](C2=O)C1=C[C@H](N23)c4c(C3)c(c5c(n4)cccc5)/C=N\OCCN(C)C / 1 / 1 / Training / 0.115352
s101 / S=C=NCCc1ccccc1 / 1 / 0 / Training / 0.060925
s102 / c1cc(O)ccc1-c(c2=O)coc(c23)cc(O)cc3 / 1 / 1 / Training / 0.007498
s103 / O=S(=O)(O)O[C@H](CC1)CC(=CC2)[C@]1(C)[C@H](CC3)[C@H]2[C@@H]([C@]34C)CCC4=O / 1 / 1 / Test / 0.042207
s104 / CC1=C(F)CC(C2=C13)=NC4=C([C@H]2[C@H](N)CC3)Cn5c4cc6c(c5=O)COC(=O)[C@]6(O)CC / 1 / 1 / Training / 0.005444
s105 / CC[C@]1(O)C(=O)OCc(c2=O)c1cc(n23)c4c(C3)c(/C=N/OC(C)(C)C)c5c(n4)cccc5 / 1 / 1 / Training / 0.113553
s106 / c1ccc(F)cc1COc(cc2)c(Cl)cc2Nc3ncnc(c34)ccc(c4)c(cc5)oc5CNCCS(=O)(=O)C / 1 / 1 / Test / 0.029486
s107 / c1ccccc1C[C@@H](C(=O)O)NC(=O)c(cc2Cl)c(O)c(c23)C(=O)O[C@@H](C3)C / 1 / 1 / Test / 0.003465
S108 / O=C(C1)c(c2c13)c(C)c(n2)cc4[nH]c(c(C)c4CC)cc5[nH]c(c(C)c5CC)cc6nc3c(c6C)CCC(=O)O / 1 / 0 / Remove / 0.087122
s109 / Oc1ccc(cc1)/C=C\c2cc(O)cc(O)c2 / 1 / 1 / Training / 0.018779
s110 / CC(C)c1nc(N(C)S(=O)(=O)C)nc(c2ccc(F)cc2)c1/C=C/[C@@H](O)C[C@@H](O)CC(=O)O / 1 / 1 / Training / 0.007253
s111 / CC(C)c1nc(N(C)S(=O)(=O)C)nc(c2ccc(F)cc2)c1/C=C/[C@@H](O)C[C@@H](O)CC(=O)O / 1 / 1 / Test / 0.007253
s112 / c1c(Cl)cc(Cl)c(c12)NC(=O)C\2=N/NC(=S)Nc3ccc(cc3)OC / 1 / 1 / Training / 0.055673
s113 / c1ccc(OC)c(c12)C(=O)c3c(C2=O)c(O)c4c(c3O)[C@@H](C[C@@](C4)(O)C(=O)C)O[C@@H]5C[C@H](N)[C@@H](O)[C@@H](O5)C / 1 / 1 / Test / 0.029689
s114 / c1cccc(c12)c(CC[Si](C)(C)C)c3c(n2)-c4n(C3)c(=O)c5c(c4)[C@](O)(CC)C(=O)OC5 / 1 / 1 / Training / 0.007418
s115 / C1CNCCN1c(c(F)c2)cc(c23)n4c(S[C@@H]4C)c(c3=O)C(=O)O / 1 / 1 / Training / 0.021919
s116 / Oc1c(O)ccc(c1)C(O2)=C(C(=O)[C@H]([C@@H]23)C(O)=CC(=C3)O)O[C@@H]4[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O4)C(=O)O / 1 / 1 / Training / 0.010892
s117 / CC[C@]1(O)CC(=O)OCc(c2=O)c1cc(n23)-c4c(C3)cc5c(n4)cccc5 / 1 / 1 / Training / 0.013114
s118 / Fc(c1)c(F)cc(c12)cc3c(n2)-c4n(C3)c(=O)c5c(c4)[C@](O)(CC)CC(=O)OC5 / 1 / 1 / Test / 0.02196
S119 / CC(=O)Nc1ccc(O)cc1 / 1 / 1 / Remove / 0.048748
s120 / Cc1nccc(c12)c3c([nH]2)cc(cc3)OS(=O)(=O)O / 1 / 1 / Training / 0.034156
s121 / FC(F)(F)c1ccc(cc1)NC(=O)c2cnoc2C / 1 / 1 / Training / 0.041088
s122 / O=C(O)C[C@@H](O)C[C@H](O)/C=C/c(c1c2ccc(F)cc2)c(C3CC3)nc(c14)cccc4 / 1 / 1 / Training / 0.032749
S123 / c1ccccc1[C@]2(NC(=O)NC2=O)c3ccc(O)cc3 / 1 / 1 / Remove / 0.029673
S124 / OC(=O)CC[C@H]1[C@H](C)c(nc12)cc3[nH]c(c(c3C)C=C)cc4[nH]c(c(c4C)CC)cc5nc(c(c5C)C(=O)O)c2CC(=O)O / 1 / 0 / Remove / 0.094149
s125 / c1cc(N)ccc1S(=O)(=O)N(CC(C)C)C[C@@H](O)[C@@H](Cc2ccccc2)NC(=O)O[C@@H]3CCOC3 / 0 / 0 / Training / 0.026166
s126 / COc(c1)c(O)ccc1/C=C\C(=O)CC(=O)/C=C\c2cc(OC)c(O)cc2 / 0 / 1 / Training / 0.016505
s127 / c1cc(O)ccc1\C=C\C(=O)CC(=O)/C=C/c2ccc(O)cc2 / 0 / 0 / Test / 0.082628
s128 / c1cc(O)ccc1\C=C\C(=O)CC(=O)/C=C/c2cc(OC)c(O)cc2 / 0 / 0 / Test / 0.032435
s129 / CCCC[C@H](CC)COC(=O)c1c(cccc1)C(=O)OC[C@@H](CC)CCCC / 0 / 0 / Training / 0.034708
s130 / O=C(O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)NC[C@@H](CN2)N(C=O)c(c23)c(=O)nc([nH]3)N / 0 / 1 / Training / 0.01485
s131 / c1ccncc1CN(C[C@@H]2C(=O)NC(C)(C)C)CCN2C[C@@H](O)C[C@H](Cc3ccccc3)C(=O)N[C@@H]([C@@H](O)C4)c(c45)cccc5 / 0 / 0 / Training / 0.055378
s132 / Cc1c(O)cccc1C(=O)N[C@@H](CSc2ccccc2)[C@H](O)CN([C@@H](C3)C(=O)NC(C)(C)C)C[C@H]([C@H]34)CCCC4 / 0 / 0 / Test / 0.113254
s133 / C1=C(C)C(=O)[C@H](O)[C@](CO)([C@@]2(C)[C@H](O)[C@H]3O)[C@@H]1O[C@H]3[C@]24OC4 / 0 / 0 / Training / 0.316552
S134 / COC(=O)C1=C(C)NC(C)=C(C(=O)OCC)[C@H]1c2cc([N+]([O-])=O)ccc2 / 0 / 1 / Remove / 0.011263
s135 / CCCC[C@@H](CC)COC(=O)c1ccccc1C(=O)OC[C@H](CC)CCCC / 0 / 0 / Training / 0.028093
s136 / O=C(O)[C@@H](CC)[C@@H]1O[C@@H]([C@@H](C)CC1)[C@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]([C@H](C)C[C@H]2C)O[C@@]23O[C@@]4([C@H](O)C=C3)O[C@](C)(CC4)[C@H](CC5)O[C@@H](C)[C@@]5(O)CC / 0 / 0 / Training / 0.139186
s137 / CO[C@H](C1)[C@@H](O)CC[C@@H]1C[C@H](C)[C@H](OC(=O)[C@@H]2N(C(=O)C3=O)CCCC2)CC(=O)[C@@H](C)/C=C(\C)[C@@H](O)[C@H](OC)C(=O)[C@H](C)C[C@@H](C)/C=C\C=C\C=C(/C)[C@@H](OC)C[C@H](O4)CC[C@@H](C)[C@@]34O / 0 / 0 / Test / 0.214721
s138 / O[C@]12C(=O)C(=O)N3[C@H](CCCC3)C(=O)O[C@H](C(\C)=C\[C@H](C[C@@H]4OC)CC[C@H]4O)[C@@H](C)[C@@H](O)CC(=O)[C@@H](CC=C)\C=C(C)\C[C@@H](C)C[C@@H](OC)[C@H](O1)[C@@H](OC)C[C@@H]2C / 0 / 0 / Training / 0.138446
s139 / OC/C=C(C)/C=C\C=C(C)\C=C\C(C1(C)C)=C(C)CCC1 / 0 / 1 / Training / 0.01527
S140 / OCCC(SC1)=[C](C)=[N+]=1Cc2c(N)nc(C)nc2 / 0 / 1 / Remove / 0.003488
s141 / Oc1c(CO)c(CO)cnc1C / 0 / 0 / Test / 0.127089
s142 / Cc1c(C)c(O)c(C)c(c12)CC[C@](O2)(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C / 0 / 0 / Training / 0.058953
s143 / c1cccc(c12)C(=O)C(C)=C(C2=O)C/C=C(\C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)C / 0 / 0 / Training / 0.081701
s144 / C1/C=C(\C)C[C@H](C)/C=C/C=C(CO[C@H]2[C@@H](O)C(=C3)C)\[C@]2(O)[C@H]3C(=O)O[C@@H](C4)C[C@@H]1O[C@]45O[C@@H](/C(C)=C/C(C)C)[C@@H](C)/C(C5)=N\OC / 0 / 0 / Test / 0.220158
s145 / c1ccccc1Sc(c2)ccc(c23)nc([nH]3)NC(=O)OC / 0 / 1 / Training / 0.069889
s146 / C1=CC=N/C1=c(c2)\[nH]c(\c2OC)=C/c3cc(c([nH]3)C)CCCCC / 0 / 0 / Training / 0.026187
s147 / C1C[C@@H](O)CC([C@]12C)=CC[C@@H]3[C@@H]2CC[C@@]4(C)[C@H]3CC[C@H]4[C@@H](C)CC[C@@H](CC)C(C)C / 0 / 0 / Training / 0.058839
s148 / c1ccccc1C(=O)C[C@H]2N(C)[C@H](CCC2)C[C@H](O)c3ccccc3 / 0 / 0 / Training / 0.049991
s149 / O=c1nc(N)ccn1[C@H]2O[C@H](CO)[C@@H](O)[C@H]2O / 0 / 0 / Training / 0.017962
s150 / O=C1C=C(C)C(=O)c(c12)cccc2O / 1 / 1 / Training / 0.015675
s151 / NNNc(cc1)c(I)cc1C(=O)N(CC2)CCN2c(n3)nc(N)c(c34)cc(OC)c(c4)OC / 1 / 1 / Training / 0.051386
s152 / c1ccccc1-c(cc2=O)oc(c23)c4c(cc3)cccc4 / 1 / 1 / Training / 0.04845
s153 / Nc1nc(N)nc(c12)nc(O)c(n2)CN(C)c3ccc(cc3)C(=O)N[C@@H](C(=O)O)CCC(=O)O / 1 / 1 / Test / 0.052534
s154 / C1CNCCN1c(c(F)c2)cc(c23)n(C4CC4)cc(c3=O)C(=O)O / 1 / 1 / Test / 0.021026
s155 / c1c(O)ccc(c12)c3c(o2)c4c(oc3=O)cc(O)cc4 / 1 / 1 / Training / 0.00522
s156 / CCn1cc(C(=O)O)c(=O)c(c12)cc(F)c(c2)N3CCNCC3 / 1 / 1 / Training / 0.042624
s157 / O=C(O)C[C@@H](O)C[C@@H](O)/C=C/c1c(C(C)C)nc(C(C)C)c(COC)c1-c2ccc(F)cc2 / 1 / 1 / Training / 0.004081
s158 / c1ccnc(c12)ccc3c2nc(N)n3C / 1 / 1 / Training / 0.012338
s159 / OC[C@@H](O)[C@H]1C(O)=C(C(=O)O1)O / 0 / 0 / Training / 0.043675
s160 / CCCSc(c1)ccc(c12)nc([nH]2)NC(=O)OC / 0 / 0 / Training / 0.016624
s161 / C1=CCN(CC2)C3C1(CC)C(OC(=O)C)C(O)(C(=O)OC)C4N(C=O)c(c5C234)cc(OC)c(c5)C6(C(=O)OC)CC(C7)CC(O)(CC)CN7CCc(c68)c9c([nH]8)cccc9 / 0 / 0 / Training / 0.503002
s162 / c1cccc(c12)ccc(n2)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@H](Cc3ccccc3)[C@H](O)CN([C@@H](C4)C(=O)NC(C)(C)C)C[C@@H]([C@@H]45)CCCC5 / 0 / 0 / Test / 0.097251
S163 / CC(=O)OCOC(=O)c(cc1)cc(C(O2)=O)c1C23c4c(cc(OCOC(=O)C)c(c4)CCC(=O)OCOC(=O)C)Oc5c3cc(c(c5)OCOC(=O)C)CCC(=O)OCOC(=O)C / 1 / 1 / Remove / 0.026533
s164 / O1COc(c12)cc3c(c2)cc4c(n3)-c5n(C4)c(=O)c6c(c5)[C@@](O)(C(=O)C6)CC / 0 / 0 / Training / 0.015164
s165 / c1cccc(c12)c3c4c(c2)ccc5c4c(cc3)ccc5OS(=O)(=O)O / 1 / 1 / Training / 0.02086
s166 / c1cccc(c12)c3c4c(c2)ccc5c4c(cc3)ccc5OS(=O)(=O)O / 1 / 1 / Test / 0.023553
s167 / COC(=O)Nc(n1)[nH]c(c12)ccc(c2)S(=O)(=O)CCC / 1 / 1 / Test / 0.005469
s168 / Cc1c(C)c(O)c(C)c(c12)CC[C@@](O2)(C)COc3ccc(cc3)C[C@H]4C(=O)NC(S4)=O / 1 / 1 / Training / 0.018655
s169 / C1NCCc(c12)sc(c2)C(=O)NCC(=O)c3cc(OCC(=O)O)c(cc3)OCC(=O)O / 1 / 1 / Test / 0.043553
s170 / O=c1c(F)cn(c(=O)[nH]1)[C@H]2O[C@H]([C@@H](C2)O)COP(=O)(O)O / 0 / 0 / Test / 0.55377
s171 / CC(C)c1ccccc1C(=O)NC(=O)Nc2ccc(c(c2)C)Oc3ncc(Br)cn3 / 0 / 0 / Training / 0.109693
S172 / O[C@@H]1[C@@H](C(=O)O)O[C@H]([C@H](O)[C@H]1O)Oc(ccc2cc3)c4ccc5cc(c6c3c5c24)cccc6 / 1 / 1 / Remove / 0.064398
s173 / CC[C@]1(O)C(=O)OCc(c2=O)c1cc(n23)-c4c(C3)c(c5c(n4)cccc5)/C=N\OCCN / 1 / 1 / Test / 0.115154
s174 / CC[C@]1(O)C(=O)OCc(c2=O)c1cc3n2Cc(c-3nc(c45)cccc4)c5/C=N\OCCN6CCOCC6 / 1 / 1 / Training / 0.122328
s175 / O1COc(c12)cc(cc2)Oc3ncccc3C(=O)NCc4c(F)cc(cc4)O[C@@H](C)C(=O)O / 1 / 1 / Test / 0.028225
S176 / Clc(n1)nc(N)c(c12)ncn2[C@@H]3O[C@@H]([C@@H](O)C3)CO / 1 / 1 / External / 0.040077
S177 / c1ccnc(c12)ccc3c2nc(N)n3C / 1 / 1 / External / 0.010713
S178 / Oc1ccc(cc1O)/C=C/C(=O)O[C@@H](C[C@]2(O)C(=O)O)[C@H](O)[C@@H](C2)OC(=O)/C=C/c3ccc(O)c(c3)O / 1 / 1 / External / 0.004836
S179 / c1cccc(c12)c3c([nH]2)c(C)c(N)nc3C / 1 / 1 / External / 0.006549
S180 / O[C@@H]1[C@@H](C(=O)O)O[C@H]([C@H](O)[C@H]1O)Oc(cc2)cc(c23)oc(=O)cc3C / 1 / 1 / External / 0.014062
S181 / S=c1nc[nH]c(c12)nc[nH]2 / 1 / 0 / External / 2.359937
S182 / CC[C@@]1(O)C(=O)OCc(c2=O)c1cc(n23)-c4c(C3)c(CC)c5c(n4)ccc(O)c5 / 1 / 1 / External / 0.016399
S183 / [O]C(=O)CC[C@@H](C(=O)O)NC(=O)c(cc1)ccc1N(C)Cc(n2)cnc(c23)nc(N)nc3N / 1 / 1 / External / 0.059021
S184 / CC[C@@]1(O)C(=O)OCc(c2=O)c1cc(n23)-c4c(C3)cc5c(n4)cccc5N / 1 / 1 / External / 0.007171
S185 / FC(F)(F)c(cc1)ccc1NC(=O)/C(C#N)=C(\O)C / 1 / 1 / External / 0.04858
S186 / O[C@H]1[C@H](O)[C@@H](C(=O)O)O[C@H]([C@@H]1O)Oc2ccc(cc2)NC(=O)C / 1 / 1 / External / 0.00695
S187 / OS(=O)(=O)Oc(cc1)ccc1NC(=O)C / 1 / 0 / External / 0.085477
S188 / OCCOCn1cnc(c12)c(=O)nc([nH]2)N / 1 / 1 / External / 0.009464
S189 / C1=CO[C@H]2Oc3cc(OC)c(c4c3[C@@H]12)c5c(c(o4)=O)C(=O)CC5 / 1 / 1 / External / 0.009064
S190 / c1cccc(C(=O)NC)c1Sc(cc2)cc(c23)[nH]nc3/C=C/c4ncccc4 / 1 / 1 / External / 0.066556