Dear RdKiters, Why is it that the stable tautomer of the following structure is lost during inchi/smiles conversion?
[image: image.png] mol = Chem.MolFromSmiles(*"Cc1ccc([nH]nc2)c2c1"*) inchi = Chem.MolToInchi(mol) mol = Chem.MolFromInchi(inchi) smiles = Chem.MolToSmiles(mol) print(smiles) *==> Cc1ccc2n[nH]cc2c1* The H has shifted on the wrong Nitrogen… Interestingly, if you remove the methyl, the shift no longer happens: mol = Chem.MolFromSmiles(*"c1([nH]nc2)c2cccc1"*) inchi = Chem.MolToInchi(mol) mol = Chem.MolFromInchi(inchi) smiles = Chem.MolToSmiles(mol)print(smiles) ==> *c1([nH]nc2)c2cccc1* Same issue for any secondary amides: if you pass the smiles of a secondary amide, you end-up with the following unstable tautomer: [image: image.png] Thanks, Alexis
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