Skip to main content

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