From: STOUT: SMILES to IUPAC names using neural machine translation
No. | IUPAC names | BLEU Score | IUPAC names translated into SMILES using OPSIN | Tanimoto similarity Index | ||
---|---|---|---|---|---|---|
Original | Predicted | Original | Predicted | |||
1 | butyl3-methyl-12-methylidene-2,4,7,10-tetraoxatridecan-13-oate | butyl2-({2-[2-(1-methoxyethoxy)ethoxy]ethoxy}methyl)prop-2-enoate | 0.00 | O=C(OCCCC)C(=C)COCCOCCOC(OC)C | O=C(OCCCC)C(=C)COCCOCCOC(OC)C | 1.0 |
2 | ethyl3-[1,10-diiodo-9-(iodosulfanyl)-1,10-dithia-2,9-diazadecan-2-yl]propanoate | ethyl3-({6-[bis(iodosulfanyl)amino]hexyl}(iodosulfanyl)amino}propanoate | 0.10 | O=C(OCC)CCN(SI)CCCCCCN(SI)SI | O=C(OCC)CCN(SI)CCCCCCN(SI)SI | 1.0 |
3 | N,Ndimethyl-1-(prop-2-enamido)cyclopentane-1-carboxamide | N-[1-(dimethylcarbamoyl)cyclopentyl]prop-2-enamide | 0.24 | O=C(C=C)NC1(C(=O)N(C)C)CCCC1 | O=C(C=C)NC1(C(=O)N(C)C)CCCC1 | 1.0 |
4 | 6-[4-(2-cyanoethyl)phenyl]-N-[1-(hydroxycarbamoyl)ethyl]hexanamide | 2-{6-[4-(3-cyanopropyl)phenyl]hexanamido}-N-hydroxypropanamide | 0.32 | N#CCCC1=CC=C(C=C1)CCCCCC(=O)NC(C(=O)NO)C | N#CCCCC1=CC=C(C=C1)CCCCCC(=O)NC(C(=O)NO)C | 1.0 |
5 | 12-aminochrysene-6-carboxylicacid | 6-aminotetraphene-11-carboxylicacid | 0.41 | O=C(O)C1=CC=2C=3C=CC=CC3C(N)=CC2C=4C=CC=CC41 | O=C(O)C1=CC=CC2=CC=3C(N)=CC=4C=CC=CC4C3C=C21 | 1.0 |
6 | 1,3-bis[(6-bromopyridin-2-yl)methyl]-1,3-diazinane | 2-bromo-6-({3-[(6-bromopyridin-2-yl)methyl]-1,3-diazinan-1-yl}methyl)pyridine | 0.50 | BrC=1N=C(C=CC1)CN2CN(CC3=NC(Br)=CC=C3)CCC2 | BrC=1N=C(C=CC1)CN2CN(CC3=NC(Br)=CC=C3)CCC2 | 1.0 |
7 | 2,3,7-trifluoro-5-methylocta-1,3,5-triene | 2,5-difluoro-3-methylocta-1,3,5-triene | 0.61 | FC(=C)C(F)=CC(=CC(F)C)C | FC(=C)C(=CC(F)=CCC)C | 1.0 |
8 | tert-butyl4-acetyl-2-[(acetyloxy)methyl]piperazine-1-carboxylate | tert-butyl2-[(acetyloxy)methyl]-4-acetylpiperazine-1-carboxylate | 0.72 | O=C(OC(C)(C)C)N1CCN(C(=O)C)CC1COC(=O)C | O=C(OC(C)(C)C)N1CCN(C(=O)C)CC1COC(=O)C | 1.0 |
9 | N-[(3-cyanophenyl)methyl]pyrimido[4,5-b]indolizine-10-carboxamide | N-[(3-cyanophenyl)methyl]-5H-pyrimido[4,5-b]indolizine-10-carboxamide | 0.83 | N#CC1=CC=CC(=C1)CNC(=O)C=2C=3N=CN=CC3N4C=CC=CC24 | N#CC1=CC=CC(=C1)CNC(=O)C=2C=3N=CN=CC3N4C=CC=CC24 | 1.0 |
10 | (5-benzylhexa-3,5-dien-2-ylidene)aminomethanesulfonate | (6-benzylhexa-3,5-dien-2-ylidene)aminomethanesulfonate | 0.92 | O=S(=O)([O-])CN=C(C=CC(=C)CC=1C=CC=CC1)C | O=S(=O)([O-])CN=C(C=CC=CCC=1C=CC=CC1)C | 1.0 |