Table 8 Examples of OPSIN retranslation errors
From: STOUT V2.0: SMILES to IUPAC name conversion using transformer models
Original compound (reference | original structure) | STOUT-generated compound (AIN | OPSIN-translated structure) | Problems identified by OPSIN with generated names |
|---|---|---|
tert-butyl 12-(2-aminoquinolin-8-yl)-13-fluoro-16-methoxy-8-methyl-9-oxa-2,5,11,15,17-pentazatricyclo[8.7.1.014,18]octadeca-1(17),10,12,14(18),15-pentaene-5-carboxylate | tert-butyl 15-(2-aminoquinolin-8-yl)-14-fluoro-17-methoxy-11-methyl-10-oxa-2,5,8,16,18-pentazatricyclo[7.7.1.013,17]heptadeca-1(16),9(17),13(17),14-tetraene-5-carboxylate | Could not find the atom with locant 18 |
tert-butyl (8S)-12-chloro-13-fluoro-16-methoxy-6,8-dimethyl-9-oxa-2,5,11,15,17-pentazatricyclo[8.7.1.014,18]octadeca-1(17),10,12,14(18),15-pentaene-5-carboxylate | tert-butyl (3S)-16-chloro-15-fluoro-13-methoxy-3,5-dimethyl-2-oxa-6,9,11,12,14-pentazatricyclo[8.6.1.015,17]heptadeca-1(16),10,12,14-tetraene-6-carboxylate | Atom is in unphysical valency state! Element: C valency: 5 |
N'-[[methyl-[1-(6-spiro[1,2-dihydrofluorene-9,9'-6,7-dihydroxanthene]-3'-ylpyridin-3-yl)ethyl]amino]-phenylmethyl]benzenecarboximidamide | N'-[[methyl-[1-(6-spiro[1,2-dihydrotriphenylene-9,9'-6,7-dihydroxanthene]-3'-ylpyridin-3-yl)ethyl]amino]-phenylmethyl]benzenecarboximidamide | Failed to assign all double bonds! (Check that indicated hydrogens have been appropriately specified) |
(7S,10S,13S)-N-[(1S)-1-cyclopropylethyl]-10-(2-morpholin-4-ylethyl)-9,12-dioxo-13-(2-oxopyrrolidin-1-yl)-2-oxa-8,11-diazabicyclo[13.3.1]nonadeca-1(18),15(19),16-triene-7-carboxamide | (7S,10S,13S)-N-[(1S)-1-cyclopropylethyl]-13-(2-morpholin-4-ylethyl)-9,12-dioxo-16-(2-oxopyrrolidin-1-yl)-2-oxa-8,11-diazabicyclo[16.3.1]docosa-1(21),18(22),19-triene-7-carboxamide | Could not find atom that: < stereoChemistry locant = "10" type = "RorS" value = "S" stereoGroup = "Abs" > 10S < /stereoChemistry > appeared to be referring to |
(4R,6R)-6-[(1R)-1-[[2-[amino(methanimidoyl)amino]acetyl]amino]ethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[3-(1,2,4-triazol-4-yl)azetidine-1-carbonyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid | 4R,6R)-4-[(1R)-1-[[2-[amino(methanimidoyl)amino]acetyl]amino]ethyl]-6-methyl-2-oxo-3-[(3S,5S)-5-[3-(1,2,4-triazol-4-yl)azetidine-1-carbonyl]piperidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-3-ene-8-carboxylic acid | Suffix: imido does not apply to the group it was associated with (type: standardGroup) according to suffixApplicability.xml |