---------- Forwarded message ----------
From: Markus Sitzmann <markus.sitzm...@gmail.com>
Date: Thu, May 8, 2014 at 3:27 PM
Subject: Re: [Rdkit-discuss] Tautomeric InChIs
To: Edward Pyzer-Knapp <e.o.pyzerkn...@gmail.com>
Hi Edward,
since your InChI is a Standard InChI ("1S/"): tautomeric forms are
purposely *not* preserved by Standard InChI - that's why we created
Standard InChI (with non-standard InChI's it is another story, those
you can make tautomer-sensitive or insensitive).And actually many
people complain that Standard InChI falls short in some cases
regarding tautomer normalization :-).
Best,
Markus
On Thu, May 8, 2014 at 3:16 PM, Edward Pyzer-Knapp
<e.o.pyzerkn...@gmail.com> wrote:
> Hi all,
>
> I have been playing around with RDKIT for a while now - great work guys!
>
> I have recently hit an issue when using InChIs:
>
> When generating both inchi and smiles from a rdkit Mol, I get two different
> structures, even if I use the smiles as an input for the inchi generation.
>
> An example:
>
> smiles = "[H]N1C(=O)C(=C2C(=O)c3c(Cl)sc(F)c3N2[H])c2sc(F)c(Cl)c21" (I should
> add this smiles was generated by RDKIT, from a Mol file)
>
> mol = MolFromSmiles(smiles)
> inchi = MolToInchi(mol)
>
> print inchi
> InChI=1S/C12H2Cl2F2N2O2S2/c13-3-6-8(21-10(3)15)2(12(20)18-6)4-7(19)1-5(17-4)11(16)22-9(1)14/h17H,(H,18,20)
>
> when comparing the smiles and the inchi, the C=O has changed to an OH and a
> C-N-H has changed to a C=N. I realise that these are tautomers of each
> other, but surely the tautomeric form should be preserved when interchanging
> smiles to inchi? Since at the moment, going Smiles->Inchi->Smiles does NOT
> result in the original smiles...
>
> There is a layer in the INCHI standard which would allow description of
> this, is there a way to turn that on?
>
> Many Thanks,
>
> Ed Pyzer-Knapp
>
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