Bug with Substructure Matcher of Aromatised Molecules

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1

Hi,

If I provide a list of aromatised  molecules (below) which can exist in two possible tautomers (2-pyridinone and 2-hydroxypyridine cpds), then the substructure searcher doesnt find all of them when using 2-hydroxy pyridine as the query molecule (Oc1ccccn1), even when tautomer or resonance is selected.

Oc1cc(Cl)ccn1
Clc1cc[nH]c(=O)c1
Fc1c[nH]c(=O)cc1Cl
Oc1ncc(F)c(Cl)c1Br

 

So I then decided to to De-aromatise them with the Dearomatiser node, but this only processed the 2-hydroxypyridines to the kekule form, and not the 2-pyridinones.

I think there is some bug here in processing some aromatised tautomer forms.

Thanks

Simon.

2

Simon,

That is actually not a bug but a known limitation of Indigo's [de]aromatisation algorithms. They do not handle the 2-pyridinone well yet (as well as all other structures that have the double bond going from an aromatic cycle). Improving the algorithms is considered for this summer.

 

Best regards,

Dmitry

3

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