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Table 5 Predicted IUPAC name strings with a Tanimoto similarity index of 1.0 but a low BLEU score

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