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SMILES with "Ignored invalid Cis/Trans specification" #269

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egonw opened this issue Mar 8, 2025 · 0 comments
Open

SMILES with "Ignored invalid Cis/Trans specification" #269

egonw opened this issue Mar 8, 2025 · 0 comments
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@egonw
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egonw commented Mar 8, 2025

In the 1M IUPAC names project, I found three IUPAC names that parse with OPSIN, but the returning SMILES cannot be parsed with the CDK (2.10) without the warning "Ignored invalid Cis/Trans specification":

Image

The CDK warning is:

org.openscience.cdk.smiles.SmilesParser WARN: Ignored invalid Cis/Trans specification: 
org.openscience.cdk.smiles.SmilesParser WARN: CN\1CCC2=C(\C(=C/C(/C(=C1)\C(=O)[O-])=C\OC)\C1=CC=C(C=C1)C)C=C(C(=C2)OC)OC
org.openscience.cdk.smiles.SmilesParser WARN:                    ^      ^                                              
org.openscience.cdk.smiles.SmilesParser WARN: Ignored invalid Cis/Trans specification: 
org.openscience.cdk.smiles.SmilesParser WARN: COC=1C(=CC2=C(\C(=C/C(/C(=C/N(CC2)C)\C(=O)OC)=C\OC)\C2=CC=C(C=C2)OC)C1)OC
org.openscience.cdk.smiles.SmilesParser WARN:                       ^             ^                                   
org.openscience.cdk.smiles.SmilesParser WARN: Ignored invalid Cis/Trans specification: 
org.openscience.cdk.smiles.SmilesParser WARN: CN\1CCC2=C(\C(=C/C(/C(=C1)\C(=O)OC)=C\OC)\C1=CC=C(C=C1)F)C=C(C(=C2)OC)OC
org.openscience.cdk.smiles.SmilesParser WARN:                    ^      ^                                            

These are the IUPAC names:

  • (4E,6E,7Z)-3-methyl-10,11-dimethoxy-6-(methoxymethylidene)-8-(4-methylphenyl)-1,2,3,6-tetrahydro-3-benzazecin-5-carboxylate
  • Methyl (4E,6E,7Z)-10,11-dimethoxy-6-(methoxymethylidene)-8-(4-methoxyphenyl)-3-methyl-1,2,3,6-tetrahydro-3-benzazecin-5-carboxylate
  • Methyl (4E,6E,7Z)-3-methyl-10,11-dimethoxy-6-(methoxymethylidene)-8-(4-fluorophenyl)-1,2,3,6-tetrahydro-3-benzazecin-5-carboxylate
@dan2097 dan2097 self-assigned this Mar 8, 2025
@dan2097 dan2097 added the bug Something isn't working label Mar 8, 2025
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