CID
int64 19
167M
| SID
int64 842k
144M
| SMILES
stringlengths 2
594
| target
int64 0
2
| PAIN_flag
stringclasses 2
values |
|---|---|---|---|---|
50,897,788
| 109,967,258
|
CNCC1=NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CN3
| 1
|
No
|
65,628
| 144,206,324
|
CN1C2=C(C=C(C=C2)N(CCCl)CCCl)N=C1CCCC(=O)O
| 1
|
No
|
14,708
| 144,206,325
|
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@@H]4[C@@]3(CC5=NON=C5C4)C
| 2
|
No
|
3,085,168
| 144,206,326
|
CC1=NC=C(C(=N1)N)CN(C=O)/C(=C(\CCO)/SS/C(=C(/C)\N(CC2=CN=C(N=C2N)C)C=O)/CCO)/C
| 0
|
No
|
2,449
| 144,206,327
|
CC1=C(C(=O)C(=C(C1=O)C)C(CCCCCC(=O)O)C2=CC=CC=C2)C
| 2
|
PAIN
|
54,158
| 144,206,328
|
CC1=CC(=C(C(=C1NC(=O)CN(CC(=O)O)CC(=O)O)C)Br)C
| 0
|
No
|
92,140
| 144,206,329
|
CCCC(=O)OC[C@H]([C@H]([C@H](CN1C2=C(C=C(C(=C2)C)C)N=C3C1=NC(=O)NC3=O)OC(=O)CCC)OC(=O)CCC)OC(=O)CCC
| 1
|
No
|
6,505
| 144,206,330
|
CCCCOC(=O)CC(CC(=O)OCCCC)(C(=O)OCCCC)OC(=O)C
| 2
|
No
|
54,708,862
| 144,206,333
|
C1=CC=C(C(=C1)C(=O)O)[O-].C1=CC=C(C(=C1)C(=O)O)[O-].O.O.O.O.[Mg+2]
| 0
|
No
|
44,072
| 144,206,456
|
C1=CC(=C(C=C1C(F)(F)F)Cl)OC2=CC(=C(C=C2)[N+](=O)[O-])C(=O)[O-].[Na+]
| 0
|
No
|
71,992
| 144,206,457
|
C[C@H](CSC(=O)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O
| 0
|
No
|
71,884
| 144,206,458
|
CCC(C)(C)OC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N
| 0
|
No
|
148,121
| 144,206,459
|
C#CCC(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
| 1
|
No
|
56,840,936
| 144,206,460
|
C/C=C\1/C(=O)NC(C(=O)O[C@H]\2CC(=O)N[C@@H](C(=O)N[C@H](CSSCC/C=C2)C(=O)N1)C(C)C)C(C)C
| 1
|
No
|
11,243,969
| 144,206,461
|
C1[C@@H]2C[C@@H]2N([C@@H]1C#N)C(=O)[C@H](C34CC5CC(C3)CC(C5)(C4)O)N
| 0
|
No
|
5,281,042
| 144,206,462
|
C[N+]1(CCC2=CC(=C(C=C2[C@H]1CC3=CC(=C(C(=C3)OC)OC)OC)OC)OC)CCCOC(=O)CC/C=C/CCC(=O)OCCC[N+]4(CCC5=CC(=C(C=C5[C@H]4CC6=CC(=C(C(=C6)OC)OC)OC)OC)OC)C
| 0
|
No
|
54,686,904
| 144,206,463
|
CC(C)(C)NCC(=O)NC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C
| 0
|
No
|
13,649,426
| 144,206,465
|
CCC1(CC2=CC=CC=C2C1)C3=CN=CN3.Cl
| 2
|
No
|
23,663,404
| 144,206,467
|
CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C3=CC=CC(=C3O2)CCCC(=O)[O-])O)O.[Na+]
| 0
|
No
|
20,054,849
| 144,206,468
|
CC1=NC=C(C(=N1)N)CN(/C(=C(\SS/C(=C(\N(C=O)CC2=CN=C(N=C2N)C)/C)/CCOC(=O)C3=CC=CC=C3)/CCOC(=O)C4=CC=CC=C4)/C)C=O
| 2
|
No
|
115,305
| 144,206,470
|
CCCC(=O)N1CCCN(CC1)C2=NC3=CC(=C(C=C3C(=N2)N)OC)OC.Cl
| 0
|
No
|
443,867
| 144,206,471
|
CC(C)(C)C1=CC=C(C=C1)CN(C)CC2=CC=CC3=CC=CC=C32.Cl
| 2
|
No
|
5,485,221
| 144,206,472
|
CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N/OC)/C3=CSC(=N3)N)SC1)C(=O)OCOC(=O)C(C)(C)C.Cl
| 2
|
No
|
60,196,336
| 144,206,473
|
CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSC[C@H](C(=O)[O-])N)OC)SC2)C(=O)O.[Na+]
| 0
|
No
|
6,918,222
| 144,206,474
|
CO/N=C(\C1=NSC(=N1)N)/C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=C5C=CC=NN5C=C4)C(=O)[O-].Cl
| 0
|
No
|
60,196,337
| 144,206,475
|
CO/N=C(\C1=NSC(=N1)N)/C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=C5C=CC=NN5C=C4)C(=O)[O-].OS(=O)(=O)O
| 0
|
No
|
441,348
| 144,206,478
|
CCN(CC)CCOC(=O)C1=C(C=C(C=C1)N)Cl.Cl
| 0
|
No
|
214,348
| 144,206,479
|
C1=CC=C(C(=C1)C2=NN(C(=N2)C3=CC=CC=C3O)C4=CC=C(C=C4)C(=O)O)O
| 1
|
No
|
5,362,115
| 144,206,480
|
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N(CC(=O)O)C2CC3=CC=CC=C3C2.Cl
| 2
|
No
|
91,670
| 144,206,482
|
CCCCC(=O)OCC(=O)[C@H]1[C@@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2C[C@@H](C4=CC(=O)C=C[C@@]43C)F)F)O)C)C
| 2
|
No
|
3,307
| 144,206,484
|
CCC1=CC2=C(S1)N3C(=NN=C3CN=C2C4=CC=CC=C4Cl)C
| 0
|
No
|
14,257,662
| 144,206,485
|
C1C[C@H](N(C1)C(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=CC=C4)N)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N
| 0
|
No
|
214,356
| 144,206,487
|
C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)OP(=O)(O)O
| 0
|
No
|
636,398
| 144,206,491
|
CCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)O)C)C(=O)COC(=O)CC
| 0
|
No
|
47,462
| 144,206,494
|
C1=CC=C(C(=C1)C(=O)[O-])NC2=C(C=CC(=C2)Cl)C(=O)[O-].[Na+].[Na+]
| 0
|
No
|
171,808
| 144,206,497
|
C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC[C@H](O3)CNC)N)N)N)O.OS(=O)(=O)O
| 0
|
No
|
26,383
| 144,206,498
|
CCCCC1=CC2=C(C=C1OCC3=CC=CC=C3)NC=C(C2=O)C(=O)OC
| 0
|
No
|
217,048
| 144,206,499
|
CCN(CC)C1=CC(=C(C=C1)N=NC2=CC=C(C=C2)S(=O)(=O)N(C)C)S(=O)(=O)NCC[N+]3=CC=CC=C3.[Cl-]
| 0
|
PAIN
|
3,083,870
| 144,206,500
|
CC(CN1C2=CC=CC=C2S(=O)(=O)C3=CC=CC=C31)CN(C)C.Cl
| 0
|
PAIN
|
20,055,528
| 144,206,501
|
CC1=C(N=C(N=C1N)C(CC(=O)N)NCC(C(=O)N)N)C(=O)NC(C(C2=CN=CN2)O[C@H]3[C@H]([C@H]([C@@H]([C@@H](O3)CO)O)O)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)OC(=O)N)O)C(=O)NC(C)C(C(C)C(=O)NC(C(C)O)C(=O)NCCC5=NC(=CS5)C6=NC(=CS6)C(=O)NCCCN[C@@H](C)C7=CC=CC=C7)O.OS(=O)(=O)O
| 1
|
No
|
40,703
| 144,206,502
|
CC1(C2CCC(C1C2)CCOCC[N+]3(CCOCC3)CC4=CC(=C(C=C4Br)OC)OC)C.[Br-]
| 1
|
No
|
51,051,629
| 144,206,503
|
C1=C(NC=N1)C[C@@H](C(=O)O)[N-]C(=O)CCN.[Zn]
| 0
|
No
|
80,278
| 144,206,504
|
C(C(COP(=O)([O-])[O-])O)O.[K+].[K+]
| 0
|
No
|
4,887
| 144,206,505
|
C1=CC=C(C=C1)CCCCOC2=CC=C(C=C2)C(=O)NC3=CC=CC4=C3OC(=CC4=O)C5=NNN=N5
| 0
|
No
|
443,984
| 144,206,509
|
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)S(=O)(=O)[O-])C(=O)[O-])C.[Na+].[Na+]
| 0
|
No
|
5,282,199
| 144,206,513
|
CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CCC(=O)C)/C)/C)/C)C
| 0
|
No
|
60,936
| 144,206,514
|
C1=CC(=CC=C1SC(P(=O)(O)[O-])P(=O)(O)[O-])Cl.[Na+].[Na+]
| 0
|
No
|
54,682,461
| 144,206,515
|
CCC[C@]1(CC(=C(C(=O)O1)[C@H](CC)C2=CC(=CC=C2)NS(=O)(=O)C3=NC=C(C=C3)C(F)(F)F)O)CCC4=CC=CC=C4
| 2
|
No
|
4,659,569
| 144,206,516
|
CC1=CC=C(C=C1)C(=O)C2=CC(=C(C(=C2)O)O)[N+](=O)[O-]
| 2
|
PAIN
|
9,938,056
| 144,206,517
|
CC1=C(C(=C(C2=C1O[C@](CC2)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)OC(=O)CCC(=O)OCCO)C
| 2
|
No
|
54,693,468
| 144,206,518
|
C1=CC=C(C(=C1)C(=O)O)[O-].C1=CC=C(C(=C1)C(=O)O)[O-].[Zn+2]
| 0
|
No
|
3,033,690
| 144,206,519
|
C[C@H](CSC(=O)C1=CC=CC=C1)C(=O)N2C[C@H](C[C@H]2C(=O)[O-])SC3=CC=CC=C3.C[C@H](CSC(=O)C1=CC=CC=C1)C(=O)N2C[C@H](C[C@H]2C(=O)[O-])SC3=CC=CC=C3.[Ca+2]
| 0
|
No
|
5,380
| 144,206,520
|
CCCCOC(=O)C(=O)NC1=CC=CC(=C1)C2=NNN=N2
| 0
|
No
|
37,497
| 144,206,521
|
CCCN(CC)C(CC)C(=O)NC1=C(C=CC=C1C)C
| 0
|
No
|
2,733,516
| 124,891,692
|
CCSC(=NC1=CC=C(C=C1)C(F)(F)F)N.Cl
| 2
|
No
|
4,619,591
| 124,896,725
|
CCN(CC1=CC(=CC=C1)S(=O)(=O)[O-])C2=CC=C(C=C2)C(=C3C=CC(=[N+](CC)CC4=CC(=CC=C4)S(=O)(=O)[O-])C=C3)C5=CC=CC=C5S(=O)(=O)[O-]
| 1
|
PAIN
|
55,283
| 144,204,405
|
CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OC[C@H]5CO[C@](O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl
| 0
|
PAIN
|
337,359
| 144,205,232
|
C1COC2=C([C@]13C(=O)NC(=O)N3)C=C(C=C2)F
| 0
|
No
|
60,490
| 144,205,233
|
CC(C1=CC2=CC=CC=C2S1)N(C(=O)N)O
| 0
|
No
|
123,631
| 144,205,236
|
COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
| 0
|
No
|
5,281,078
| 144,205,239
|
CC1=C2COC(=O)C2=C(C(=C1OC)C/C=C(\C)/CCC(=O)OCCN3CCOCC3)O
| 1
|
No
|
10,885,665
| 144,205,241
|
CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@@H]2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
| 2
|
No
|
65,940
| 144,205,308
|
C1=CC=C(C=C1)S(=O)(=O)NCCC2=CC=C(S2)OCC(=O)O
| 0
|
No
|
5,284,442
| 144,205,309
|
C1=CC=C(C=C1)/C(=C\CCCCC(=O)O)/C2=CN=CC=C2
| 0
|
No
|
60,712
| 144,205,310
|
C1=CSC(=C1)C(=O)C2=C(N(C3=C2C=C(C=C3)Cl)C(=O)N)O
| 2
|
No
|
19,592
| 144,205,311
|
CC(C)(C(=O)O)OC1=CC=C(C=C1)C2CCCC3=CC=CC=C23
| 0
|
No
|
4,744
| 144,206,523
|
CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=CC=CC=C42
| 2
|
PAIN
|
44,246,357
| 85,267,297
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC=C(C=C3)OC
| 0
|
No
|
44,246,358
| 85,267,298
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC=CC=C3C
| 0
|
No
|
44,246,359
| 85,267,299
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC=C(C=C3)Cl
| 2
|
No
|
44,246,360
| 85,267,300
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=C(C=C(C=C3)Cl)Cl
| 1
|
No
|
44,246,361
| 85,267,301
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC=C(C=C3)C
| 2
|
No
|
44,246,362
| 85,267,302
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC=CC=C3OC
| 2
|
No
|
44,246,363
| 85,267,303
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC=CC=C3Cl
| 1
|
No
|
44,246,364
| 85,267,304
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC(=CC=C3)Cl
| 2
|
No
|
44,246,365
| 85,267,305
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC(=CC=C3)OC
| 2
|
No
|
44,246,366
| 85,267,306
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC=CC(=C3)C
| 2
|
No
|
44,246,367
| 85,267,307
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=C(C=CC(=C3)OC)OC
| 2
|
No
|
44,246,368
| 85,267,308
|
C1=CC=C(C=C1)CCC2=CNC(=O)C3=CN=CN=C23
| 2
|
No
|
44,246,369
| 85,267,309
|
C1=CC=C(C=C1)C#CC2=CNC(=O)C3=CN=CN=C23
| 0
|
No
|
44,246,370
| 85,267,310
|
C1=CC=C(C=C1)C#CC2=CN=C(C3=CN=CN=C23)Cl
| 1
|
No
|
44,246,371
| 85,267,311
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=C(C(=CC=C3)OC)OC
| 0
|
No
|
44,246,372
| 85,267,312
|
COC1=CC=CC(=C1OC)CCN2C(=CC(=O)NC2=S)N
| 2
|
No
|
44,246,373
| 85,267,313
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=C(C=C(C=C3)OC)OC
| 1
|
No
|
44,246,374
| 85,267,314
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=C(C=CC=C3Cl)Cl
| 1
|
No
|
44,246,375
| 85,267,315
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC(=C(C=C3)OCC)OCC
| 2
|
No
|
44,246,376
| 85,267,316
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC=CS3
| 0
|
No
|
44,246,377
| 85,267,317
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC(=CC(=C3)OC)OC
| 2
|
No
|
44,246,378
| 85,267,318
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=C(C=CC=C3OC)OC
| 0
|
No
|
44,246,379
| 85,267,319
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC(=C(C=C3)Cl)Cl
| 2
|
No
|
44,246,380
| 85,267,320
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC=CC=N3
| 0
|
No
|
44,246,381
| 85,267,321
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCCC3=CC=CC=C3
| 1
|
No
|
44,246,382
| 85,267,322
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC(C)C
| 2
|
No
|
44,246,383
| 85,267,323
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC
| 0
|
No
|
44,246,384
| 85,267,324
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=C(C=CC=C3C)C
| 2
|
No
|
44,246,385
| 85,267,325
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC(C)(C)C
| 1
|
No
|
44,246,386
| 85,267,326
|
CC(C)N1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC(=C(C=C3)OC)OC
| 2
|
No
|
44,246,387
| 85,267,327
|
CN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC(=C(C=C3)OC)OC
| 0
|
No
|
44,246,388
| 85,267,328
|
COC1=C(C=C(C=C1)CCN2C3=C(CN(CN3)C4=CC=CC=C4)C(=O)NC2=S)OC
| 2
|
No
|
44,246,389
| 85,267,329
|
CCCN1CC2=C(NC1)N(C(=S)NC2=O)CCC3=CC(=C(C=C3)C)C
| 2
|
No
|
End of preview. Expand
in Data Studio
Dataset Purpose
The dataset TDP1_inhibitors_PAIN_flagged is a part of the study "Leveraging of the IUPAC Names and Machine Learning for Assisting Drug Discovery and Development, demonstrated on the Case of Human Tyrosyl-DNA Phosphodiesterase 1 (TDP1) Inhibitors" https://doi.org/10.48550/arXiv.2503.05591
Info
The isomers had been removed.
Samples were PAIN flagged but were not removed from the raw data: PubChem AID 686978 bioassay on "qHTS for Inhibitors of Human Tyrosyl-DNA Phosphodiesterase 1 (TDP1): qHTS in Cells in Absence of CPT", https://pubchem.ncbi.nlm.nih.gov/bioassay/686978
Used:
from rdkit import Chem
from rdkit.Chem.FilterCatalog import FilterCatalog, FilterCatalogParams
Source code: https://github.com/articlesmli/IUPAC_ML_model_TDP1/blob/main/IUPAC_ML_model/PAINs_entire_data.ipynb
Dataset Details
Dataset: 410,564 samples
PAINs: 21,761 samples
Before applying the PAIN filter: Inactive 236,226; Inconclusive 112,867; Active 61,471
Samples that are not PAINs: Inactive 227,158; Inconclusive 105,950; Active 55,695
The dataset contains 5 columns:
Column 1: CID (PubChem Compounds` identifiers)
Column 2: SID (PubChem Substances` identifiers)
Column 3: SMILES
Column 4: target: "1": The molecule is a TDP1 inhibitor; "0": The molecule is not a TDP1 inhibitor; "2": The molecule is inconclusive regarding TDP1 inhibition.
Column 5: PAIN flag
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