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 |
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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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