Derify/ChemBERTa_augmented_pubchem_13m
Fill-Mask
•
Updated
•
1.84k
Datasets:
smiles
stringlengths 3
806
| canonical_smiles
stringlengths 3
806
|
|---|---|
O=C(c1ccc2[nH]ccc2c1)N(Cc1ccsc1)C1CC1 | c1c(C(N(C2CC2)Cc2ccsc2)=O)ccc2[nH]ccc12 |
CC(C)([NH3+])C(CC(=O)[O-])c1ccccc1OC(F)F | CC(C)([NH3+])C(CC(=O)[O-])c1ccccc1OC(F)F |
COc1ccc(C)cc1C(SC)C(=O)Oc1ccc(C)cc1 | COc1ccc(C)cc1C(SC)C(=O)Oc1ccc(C)cc1 |
CC1SCCN(C(=O)Cc2csc(N)n2)C1C | c1sc(nc1CC(=O)N1CCSC(C1C)C)N |
CCn1ccnc1S(=O)(=O)Cc1cccc(C#N)c1 | c1(cc(C#N)ccc1)CS(=O)(c1nccn1CC)=O |
CNC(=O)Oc1nc(C#N)cc2c1[nH]c1ccc(S(=O)(=O)Nc3ccn[nH]3)cc12 | CNC(=O)Oc1nc(C#N)cc2c1[nH]c1ccc(S(=O)(=O)Nc3ccn[nH]3)cc12 |
Cc1ccc(Oc2ccc(c3ccc(Oc4ccc(c5ccc(Oc6ccc(C)cc6)cc5)cc4)cc3)cc2)cc1 | Cc1ccc(Oc2ccc(-c3ccc(Oc4ccc(-c5ccc(Oc6ccc(C)cc6)cc5)cc4)cc3)cc2)cc1 |
O=C(NCCCCc1ccccc1)c1cccnc1NCc1ccncc1 | C(c1cccnc1NCc1ccncc1)(=O)NCCCCc1ccccc1 |
CNC(=O)C(CC(C)C)NC(=O)c1cc(Br)cc(Br)c1 | c1c(cc(cc1Br)C(NC(C(NC)=O)CC(C)C)=O)Br |
C#CCN(C)C(=S)NC1N=C(c2ccccc2)c2cc(Cl)ccc2N(C)C1=O | N1(C(=O)C(NC(N(C)CC#C)=S)N=C(c2ccccc2)c2c1ccc(Cl)c2)C |
CCCN(Cc1nc2c([nH]1)CCc1cc(c3ccc4cc(c5c[nH+]c(CN(CCC)C(=O)CNC(=O)OC)[nH]5)ccc4c3)ccc1-2)C(=O)CNC(=O)OC | CCCN(Cc1nc2c([nH]1)CCc1cc(-c3ccc4cc(-c5c[nH+]c(CN(CCC)C(=O)CNC(=O)OC)[nH]5)ccc4c3)ccc1-2)C(=O)CNC(=O)OC |
COc1ccc(Nc2ccc(C(=O)[O-])c(N)c2)c(OC)c1 | COc1ccc(Nc2ccc(C(=O)[O-])c(N)c2)c(OC)c1 |
C[NH+]=C(NCC[NH+]1CCCCC1C)NCc1c(C)nn(C)c1C | C[NH+]=C(NCC[NH+]1CCCCC1C)NCc1c(C)nn(C)c1C |
CCCCOc1cc(c2ccc(CO)cc2)c(OCCCC)c(C#N)c1C#N | CCCCOc1cc(-c2ccc(CO)cc2)c(OCCCC)c(C#N)c1C#N |
COc1ccc2c(c1)CCC1C2CCC2(C)C(NC(C)=O)=CCC12 | COc1ccc2c(c1)CCC1C2CCC2(C)C(NC(C)=O)=CCC12 |
CC1(C)C(=O)NCCN1S(=O)(=O)CC#N | CC1(C)C(=O)NCCN1S(=O)(=O)CC#N |
CCN(CC)c1ccc(N=Nc2c(Br)cc([N+](=O)[O-])cc2S(C)(=O)=O)c(NC(C)=O)c1 | N(CC)(CC)c1ccc(c(NC(C)=O)c1)N=Nc1c(S(=O)(=O)C)cc([N+]([O-])=O)cc1Br |
CCCCS(=O)(=O)NCCc1cnc[nH]1 | CCCCS(=O)(=O)NCCc1cnc[nH]1 |
O=C1SC(=Cc2cc(Cl)c(OCc3ccc(F)cc3)c(Cl)c2)C(=O)N1Cc1ccc(Cl)cc1 | O=C1SC(=Cc2cc(Cl)c(OCc3ccc(F)cc3)c(Cl)c2)C(=O)N1Cc1ccc(Cl)cc1 |
CCC(C)(O)C[NH2+]CC(O)COCc1cccs1 | C(OCc1cccs1)C(O)C[NH2+]CC(O)(CC)C |
CCC(CC)(CC)NS(=O)(=O)c1cc(C(=O)[O-])oc1C | CCC(CC)(CC)NS(=O)(=O)c1cc(C(=O)[O-])oc1C |
CCC(CC)CNC(NCC1CCCOC1c1ccccc1)=[NH+]C | CCC(CC)CNC(NCC1CCCOC1c1ccccc1)=[NH+]C |
CCCCC(CO)Nc1nc(N)nc2ccn(Cc3cc(CCC(=O)[O-])ccc3C)c12 | CCCCC(CO)Nc1nc(N)nc2ccn(Cc3cc(CCC(=O)[O-])ccc3C)c12 |
CN(CC(CC[NH+]1CCC2(CC1)NC(=O)Cc1ccccc12)(c1ccc(Cl)c(Cl)c1)N(C)C(=O)CC(c1ccccc1)c1ccccc1)C(=O)CC(F)(F)F | [NH+]1(CCC(c2ccc(c(Cl)c2)Cl)(N(C)C(CC(c2ccccc2)c2ccccc2)=O)CN(C(=O)CC(F)(F)F)C)CCC2(NC(=O)Cc3ccccc32)CC1 |
CCCc1ccc(Oc2ccnc(C(N)=[NH2+])c2)cc1 | CCCc1ccc(Oc2ccnc(C(N)=[NH2+])c2)cc1 |
CC(COC(=O)c1cc(N=Cc2cc(O)ccc2O)ccc1O)Cc1ccccc1 | CC(COC(=O)c1cc(N=Cc2cc(O)ccc2O)ccc1O)Cc1ccccc1 |
Cc1cccc(C(=O)Nc2ccccc2)c1NC(=O)CNC(=O)C1CC[NH+](CC(=O)Nc2cccc(C(=O)Nc3cccc(F)c3)c2C)CC1 | Cc1cccc(C(=O)Nc2ccccc2)c1NC(=O)CNC(=O)C1CC[NH+](CC(=O)Nc2cccc(C(=O)Nc3cccc(F)c3)c2C)CC1 |
CCc1cc(I)c2sc(C(=O)[O-])cc2c1 | C(C)c1cc(c2c(c1)cc(C([O-])=O)s2)I |
FC(F)(F)Oc1ccccc1C[NH2+]CCOC1CCCC1 | FC(F)(F)Oc1ccccc1C[NH2+]CCOC1CCCC1 |
CCC=CCC=CCC=CCC=CCC=CCC=CCCS(=O)(=O)c1ccc(C)cc1 | CCC=CCC=CCC=CCC=CCC=CCC=CCCS(=O)(=O)c1ccc(C)cc1 |
COc1cccc(n2nnn(C)c2=O)c1COc1ccc(c2cc(C(F)(F)F)n(C)n2)cc1C | COc1cccc(-n2nnn(C)c2=O)c1COc1ccc(-c2cc(C(F)(F)F)n(C)n2)cc1C |
CCOC(=O)C(C)(Cc1ccc(O)cc1)OC | c1c(ccc(c1)CC(C(OCC)=O)(OC)C)O |
Cc1cccn2c1[nH+]cc2c1nc(NCCCc2ccccc2)ncc1C#N | Cc1cccn2c(-c3nc(NCCCc4ccccc4)ncc3C#N)c[nH+]c12 |
CC1CN(C(=O)NC2CCC[NH2+]C2)CCCO1 | CC1CN(C(=O)NC2CCC[NH2+]C2)CCCO1 |
Cc1cc(=O)nc(n2nc(C(C)(C)C)cc2NC(=O)c2ccc(=O)oc2)[nH]1 | Cc1cc(=O)nc(-n2nc(C(C)(C)C)cc2NC(=O)c2ccc(=O)oc2)[nH]1 |
CC1(C)c2ccccc2N(CCOCCN2CCNC(=O)CC(=O)NCC[NH2+]CC2)C12C=Cc1ccccc1O2 | CC1(C)c2ccccc2N(CCOCCN2CCNC(=O)CC(=O)NCC[NH2+]CC2)C12C=Cc1ccccc1O2 |
Cc1cc(Nc2nc(N3CCN(C(=O)C(NC(=O)OC(C)(C)C)c4ccc(F)cc4)CC3)nn3cccc23)n[nH]1 | Cc1cc(Nc2nc(N3CCN(C(=O)C(NC(=O)OC(C)(C)C)c4ccc(F)cc4)CC3)nn3cccc23)n[nH]1 |
COC(=O)C=Cc1ccc(OC(C)=O)cc1Cl | O(c1ccc(c(Cl)c1)C=CC(OC)=O)C(C)=O |
CCc1ccc(C[NH2+]Cc2ccccc2)cc1 | CCc1ccc(C[NH2+]Cc2ccccc2)cc1 |
CCONC(=O)c1ccc2cc(C(O)(c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)cn3)C(C)C)ccc2c1 | CCONC(=O)c1ccc2cc(C(O)(c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)cn3)C(C)C)ccc2c1 |
Clc1nc(NCCc2ncon2)nc(n2cncn2)n1 | Clc1nc(NCCc2ncon2)nc(-n2cncn2)n1 |
CC(C)Nc1cc(c2ccc3cc(C#N)cnn32)[nH+]cc1C(=O)NC1CC1CO | CC(C)Nc1cc(-c2ccc3cc(C#N)cnn23)[nH+]cc1C(=O)NC1CC1CO |
COc1ccc2cc(C([NH3+])CCC3CCCO3)ccc2c1 | COc1ccc2cc(C([NH3+])CCC3CCCO3)ccc2c1 |
Cc1cccc(C(=O)Nc2cc3c(cc2N2CCCCC2)n(C)c(=O)n3C)c1 | Cc1cccc(C(=O)Nc2cc3c(cc2N2CCCCC2)n(C)c(=O)n3C)c1 |
CCC(C)C(NC(=O)Nc1cccc(C(F)(F)F)c1)C(=O)NC1CC[NH+](Cc2ccccc2)CC1 | CCC(C)C(NC(=O)Nc1cccc(C(F)(F)F)c1)C(=O)NC1CC[NH+](Cc2ccccc2)CC1 |
CC1[NH2+]C2SCCN2C1C(=O)NC12CC(NC(=O)COc3ccc(Cl)c(F)c3)(C1)C2 | CC1[NH2+]C2SCCN2C1C(=O)NC12CC(NC(=O)COc3ccc(Cl)c(F)c3)(C1)C2 |
C=CCOC12Oc3ccc(OC(=O)NCC)cc3C3C(CCCCO)C(CCCCO)C=C(C(=NOCC)CC1N(CCOCCO)C(=O)OCCCl)C32 | C=CCOC12Oc3ccc(OC(=O)NCC)cc3C3C(CCCCO)C(CCCCO)C=C(C(=NOCC)CC1N(CCOCCO)C(=O)OCCCl)C32 |
CC1=NC(C)(c2cc([N+](=O)[O-])ccc2F)CC(C)(C(F)(F)F)O1 | CC1=NC(C)(c2cc([N+](=O)[O-])ccc2F)CC(C)(C(F)(F)F)O1 |
Cc1ccc(C(=O)NC2CCCN(S(=O)(=O)c3ccccc3)C2)cc1 | Cc1ccc(C(=O)NC2CCCN(S(=O)(=O)c3ccccc3)C2)cc1 |
CC(Cl)c1ccc(C2=CCCCC2)cc1 | CC(Cl)c1ccc(C2=CCCCC2)cc1 |
O=C(Cn1cc(S(=O)(=O)Cc2cccc(Cl)c2)c2ccccc21)NCc1ccccc1 | O=C(Cn1cc(S(=O)(=O)Cc2cccc(Cl)c2)c2ccccc21)NCc1ccccc1 |
CC(C)C1=CC2=CCC3C(C)(COCC4CO4)CCCC3(C)C2CC1 | C1CC2C(CCCC2(C)C2CCC(C(C)C)=CC2=1)(C)COCC1CO1 |
COc1ccc(C(=O)Nc2cccc(NC(=O)C(C)NC(=O)C3CC[NH+](CC(=O)Nc4ccc(C(=O)NCC(C)C)cc4C)CC3)c2)cc1 | COc1ccc(C(=O)Nc2cccc(NC(=O)C(C)NC(=O)C3CC[NH+](CC(=O)Nc4ccc(C(=O)NCC(C)C)cc4C)CC3)c2)cc1 |
COP(OC1CC(n2cc(C)c(=O)[nH]c2=O)OC1CO[Si](OC1CCCCCCCCCCC1)(O[Si](C)(C)C)O[Si](C)(C)C)N(C(C)C)C(C)C | COP(OC1CC(n2cc(C)c(=O)[nH]c2=O)OC1CO[Si](OC1CCCCCCCCCCC1)(O[Si](C)(C)C)O[Si](C)(C)C)N(C(C)C)C(C)C |
CCCCCCCCC=CCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCC)COP(=O)([O-])OCC[N+](C)(C)C | C(CC=CCCCCCCCCCCCCCC(=O)OC(COP([O-])(OCC[N+](C)(C)C)=O)COC(=O)CCCCCCCCCCCC)CCCCCC |
CC(=O)Oc1cccc(OC(=O)C(C)O)c1 | c1(cc(OC(=O)C)ccc1)OC(C(O)C)=O |
CC([NH3+])Cc1ccccc1N1CCC[NH+](C)CC1C | C1CC[NH+](CC(N1c1ccccc1CC(C)[NH3+])C)C |
COc1ccccc1c1nnc2ccc(OCCNC(=O)CC3CCCCC3)nn21 | C(Oc1nn2c(nnc2cc1)-c1c(cccc1)OC)CNC(CC1CCCCC1)=O |
COc1ccccc1CC(C)[NH+](C)CCC1C[NH2+]C1 | COc1ccccc1CC(C)[NH+](C)CCC1C[NH2+]C1 |
O=C(Nc1ccccc1C(=O)NCC(F)(F)F)c1cnccn1 | O=C(Nc1ccccc1C(=O)NCC(F)(F)F)c1cnccn1 |
Cc1ccc(C(=O)Nc2ccccc2)cc1NC(=O)C(C)[NH+]1CCC(C(=O)NCC(=O)Nc2ccccc2C(N)=O)CC1 | Cc1ccc(C(=O)Nc2ccccc2)cc1NC(=O)C(C)[NH+]1CCC(C(=O)NCC(=O)Nc2ccccc2C(N)=O)CC1 |
COc1cc2c(cc1OC)C(c1cccs1)N(C(=O)CCNC(=O)c1ccccc1)CC2 | c1(ccccc1)C(NCCC(=O)N1CCc2c(cc(c(OC)c2)OC)C1c1sccc1)=O |
CN1C(=O)C(=C2SC(=S)N(c3cccc(Cl)c3)C2=O)c2ccccc21 | CN1C(=O)C(=C2SC(=S)N(c3cccc(Cl)c3)C2=O)c2ccccc21 |
CC(OC(=O)CCCn1c(=O)oc2ccccc21)C(=O)Nc1nc(c2ccccc2)cs1 | CC(OC(=O)CCCn1c(=O)oc2ccccc21)C(=O)Nc1nc(-c2ccccc2)cs1 |
CC(=O)N1CCC(C(=O)N2CCCC2c2nc(N)ncc2c2cccc(F)c2)CC1 | CC(=O)N1CCC(C(=O)N2CCCC2c2nc(N)ncc2-c2cccc(F)c2)CC1 |
CC(C)n1ncc2c(C(=O)N3CCN(c4ccccc4)CC3)cc(c3ccccc3)nc21 | CC(C)n1ncc2c(C(=O)N3CCN(c4ccccc4)CC3)cc(-c3ccccc3)nc21 |
CCN(CC)C(=O)c1cc(NC2CC[NH+](C)C2)cc[nH+]1 | C1C(Nc2cc[nH+]c(c2)C(=O)N(CC)CC)CC[NH+]1C |
C=CCNC(=O)Nc1ccc(NC(=O)CNC(=O)c2ccc(C)c(C)c2)cc1 | Cc1cc(C(=O)NCC(Nc2ccc(NC(=O)NCC=C)cc2)=O)ccc1C |
Cc1c(C(=O)N2CC(=O)Nc3ccccc32)oc2ccc(F)cc12 | Cc1c(C(=O)N2CC(=O)Nc3ccccc32)oc2ccc(F)cc12 |
CCC(C)(C)Oc1cc(Oc2cc(C(=O)[O-])cc(C(C)(CC)OC)c2)ncn1 | CCC(C)(C)Oc1cc(Oc2cc(C(=O)[O-])cc(C(C)(CC)OC)c2)ncn1 |
Cc1c(C(=O)N2CCN(C(=O)C(C)(C)C)CC2)cnn1c1ccccc1F | Cc1c(C(=O)N2CCN(C(=O)C(C)(C)C)CC2)cnn1-c1ccccc1F |
CC(C[NH3+])SCC(=O)N1CCc2sccc2C1 | C1c2sccc2CN(C1)C(CSC(C[NH3+])C)=O |
COc1ccc(F)cc1c1ncnc(Nc2cc(F)c(F)c(CS(C)(=O)=NC#N)c2)n1 | COc1ccc(F)cc1-c1ncnc(Nc2cc(F)c(F)c(CS(C)(=O)=NC#N)c2)n1 |
CN(Cc1cccc(C#N)c1)C(=O)CCS(=O)(=O)c1ccc2c(c1)CCC2 | CN(Cc1cccc(C#N)c1)C(=O)CCS(=O)(=O)c1ccc2c(c1)CCC2 |
O=C([O-])Cc1cccc2c1C(=C=C1C=CC=CC=C1)c1ccccc1-2 | O=C([O-])Cc1cccc2c1C(=C=C1C=CC=CC=C1)c1ccccc1-2 |
CCCN1C(=CC=C2C(=O)CCCC2=O)C(C)(C)c2ccc([N+](=O)[O-])cc21 | CCCN1C(=CC=C2C(=O)CCCC2=O)C(C)(C)c2ccc([N+](=O)[O-])cc21 |
O=C1c2ccccc2NC(c2c(Cl)cccc2Cl)N1C1CC1 | O=C1c2ccccc2NC(c2c(Cl)cccc2Cl)N1C1CC1 |
CCOC(=O)c1ccc(N(CC(=O)NC(C)(C)C)S(C)(=O)=O)cc1 | CCOC(=O)c1ccc(N(CC(=O)NC(C)(C)C)S(C)(=O)=O)cc1 |
CNc1nc(C)cc(C(=O)N2CCCC3(CCCCC3)CC2)n1 | CNc1nc(C)cc(C(=O)N2CCCC3(CCCCC3)CC2)n1 |
CCCC(CC[NH3+])CCC(=O)NCC(C)OCC | CCCC(CC[NH3+])CCC(=O)NCC(C)OCC |
CN(Cc1ccccc1N1CCOCC1)C(=O)c1cn(Cc2ccccc2)c2ccccc12 | CN(Cc1ccccc1N1CCOCC1)C(=O)c1cn(Cc2ccccc2)c2ccccc12 |
COC(=O)c1ccc(C[NH+]2CCC3(CC2)CN(C(=O)c2ccc(Cl)c(Cl)c2)c2ccc(OC)cc23)cc1 | COC(=O)c1ccc(C[NH+]2CCC3(CC2)CN(C(=O)c2ccc(Cl)c(Cl)c2)c2ccc(OC)cc23)cc1 |
NC1=NC(C[NH+]2CCN(c3cccc(Cl)c3)CC2)CO1 | NC1=NC(C[NH+]2CCN(c3cccc(Cl)c3)CC2)CO1 |
O=C(COc1ccc(Oc2ccccn2)cc1)Nc1ccc(Cl)cc1 | O=C(COc1ccc(Oc2ccccn2)cc1)Nc1ccc(Cl)cc1 |
CC#CCNc1ncnc2[nH]ncc12 | CC#CCNc1ncnc2[nH]ncc12 |
CC1([NH3+])C(c2cnn3c(N)ccnc23)OC(CO)C1O | C(O)C1OC(C([NH3+])(C)C1O)c1c2nccc(n2nc1)N |
Cc1cc(F)cc2[nH]c(C(=O)N3CCCC(COc4ccccc4)C3)cc12 | Cc1cc(F)cc2[nH]c(C(=O)N3CCCC(COc4ccccc4)C3)cc12 |
CCCNC(c1cncc(OC)c1)C(F)(F)F | O(c1cncc(C(NCCC)C(F)(F)F)c1)C |
Cc1cccc(C[NH+]2CCN(C(=O)CCn3cc(C)cn3)CC2)c1 | c1c(cnn1CCC(N1CC[NH+](CC1)Cc1cc(ccc1)C)=O)C |
COc1cccc(N2CCN(c3nc4ccc(Cl)cc4s3)CC2)c1 | COc1cccc(N2CCN(c3nc4ccc(Cl)cc4s3)CC2)c1 |
CCC(CC)C1(O)CCN(C(=O)Nc2cc(Oc3ccc(F)cc3)cc(Oc3ccc(CC(=O)[O-])cc3)c2)CC1 | CCC(CC)C1(O)CCN(C(=O)Nc2cc(Oc3ccc(F)cc3)cc(Oc3ccc(CC(=O)[O-])cc3)c2)CC1 |
[NH3+]CC1(COc2ccccc2O)CCCC1 | [NH3+]CC1(COc2ccccc2O)CCCC1 |
Cc1ccc(C2[NH2+]C3(CC3)C(=O)N2C2CC[NH+](C)C2)s1 | Cc1ccc(C2[NH2+]C3(CC3)C(=O)N2C2CC[NH+](C)C2)s1 |
CC(CCNC(=O)c1ccnc(N)c1F)S(C)=O | n1c(N)c(c(C(NCCC(S(=O)C)C)=O)cc1)F |
CC(Cl)CCN(C)C(=O)c1ccc(F)cc1[N+](=O)[O-] | CC(Cl)CCN(C)C(=O)c1ccc(F)cc1[N+](=O)[O-] |
NC(=O)OC(=O)CC(C(=O)OC(N)=O)S(=O)(=O)[O-] | NC(=O)OC(=O)CC(C(=O)OC(N)=O)S(=O)(=O)[O-] |
COc1ccc2nc(C)n(c3ccc(OCCC[NH+]4CCCC4)cc3)c(=O)c2c1 | COc1ccc2nc(C)n(-c3ccc(OCCC[NH+]4CCCC4)cc3)c(=O)c2c1 |
CCn1cc(N)c(C(=O)N(C)C(C)c2ccc(C)cc2)n1 | CN(C(c1ccc(cc1)C)C)C(c1nn(cc1N)CC)=O |
CC(C)([NH3+])CNC(=O)C1=CCCSC1 | CC(C)([NH3+])CNC(=O)C1=CCCSC1 |
CS(=O)(=O)C1CCN(C2CCOCC2)C1 | S(C)(=O)(C1CCN(C1)C1CCOCC1)=O |
End of preview. Expand
in Dataset Viewer.
PubChem 10M - Augmented SMILES Dataset
This dataset is derived from the original PubChem 10M and has been canonicalized using RDKit (2024.9.4) to ensure structural consistency.
To enhance molecular diversity, 33% of the dataset was randomly sampled and augmented using RDKit’s Chem.MolToRandomSmilesVect function, following an approach similar to NVIDIA’s molmim method for SMILES augmentation.
Dataset Overview:
- Source: PubChem 10M
- Canonicalization: RDKit (2024.9.4)
- Augmentation: Random SMILES generation for 33% of the original dataset
- Total Entries: 13M SMILES
- Downloads last month
- 57
Size of downloaded dataset files:
436 MB
Size of the auto-converted Parquet files:
436 MB
Number of rows:
13,298,008
Models trained or fine-tuned on Derify/augmented_canonical_pubchem_13m