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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