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Table 6 Predicted IUPAC name strings with a BLEU score of 1.0 but a low Tanimoto similarity index

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

4-[(4-amino-2,3,6-trimethylphenyl)methyl]-2,3,5-trimethylaniline

4-[(4-amino-2,3,5-trimethylphenyl)methyl]-2,3,6-trimethylaniline

1.0

NC=1C=C(C(=C(C1C)C)CC=2C(=CC(N)=C(C2C)C)C)C

NC1=C(C=C(C(=C1C)C)CC2=CC(=C(N)C(=C2C)C)C)C

0.97

2

3-[(3-amino-2,6-diethylphenyl)methyl]-2,4-diethylaniline

3-[(3-amino-2,4-diethylphenyl)methyl]-2,6-diethylaniline

1.0

NC1=CC=C(C(=C1CC)CC=2C(=CC=C(N)C2CC)CC)CC

NC=1C(=CC=C(C1CC)CC2=CC=C(C(N)=C2CC)CC)CC

0.92

3

2-{4-[(dimethylamino)methyl]-6-[(2,6-dimethylphenoxy)methyl]-6-hydroxycyclohexa-2,4-dien-1-yl}acetonitrile

2-{4-[(2,6-dimethylphenoxy)methyl]-6-[(dimethylamino)methyl]-6-hydroxycyclohexa-2,4-dien-1-yl}acetonitrile

1.0

N#CCC1C=CC(=CC1(O)COC=2C(=CC=CC2C)C)CN(C)C

N#CCC1C=CC(=CC1(O)CN(C)C)COC=2C(=CC=CC2C)C

0.93

4

4-[4-(3-hydroxycyclohepta-1,3,6-trien-1-yl)phenyl]-N-(7-methylcyclohepta-1,4,6-trien-1-yl)butanamide

4-[4-(3-hydroxycyclohepta-1,4,6-trien-1-yl)phenyl]-N-(7-methylcyclohepta-1,3,6-trien-1-yl)butanamide

1.0

O=C(NC1=CCC=CC=C1C)CCCC=2C=CC(=CC2)C=3C=CCC=C(O)C3

O=C(NC1=CC=CCC=C1C)CCCC=2C=CC(=CC2)C=3C=CC=CC(O)C3

0.95

5

(but-1-en-2-yl)(prop-1-en-1-yl)amine

(but-1-en-1-yl)(prop-1-en-2-yl)amine

1.0

C=C(NC=CC)CC

C=C(NC=CCC)C

0.97