Re: [Rdkit-discuss] SMARTS pattern matching of canonical forms of aromatic molecules

[Jason B. <jas...@gm...>]

Start with your benzene molecule

m = Chem.MolFromSmiles('c1ccccc1')


make a pattern using Peter's example, with three aromatic atoms connected
by three aromatic bonds

patt = Chem.MolFromSmarts('a:a:a')


and it's a match:

m.HasSubstructMatch(patt)

>True


Kekulize your mol, and the pattern doesn't match

Chem.rdmolops.Kekulize(m)
m.HasSubstructMatch(patt)
>False


but if you change the smarts pattern to match aromatic atoms connected by
kekulized bonds, it matches

patt2 = Chem.MolFromSmarts('[a]=[a]-[a]')
m.HasSubstructMatch(patt2)
>True

Your original SMARTS query doesn't match, because C in a smarts string is
specifically an aliphatic carbon.  Change it to c and it will match.  It
would work, if you had removed the aromatic flags when kekulizing


m = Chem.MolFromSmiles('c1ccccc1')
Chem.rdmolops.Kekulize(m, clearAromaticFlags = True)
patt = Chem.MolFromSmarts('[C]=[C]-[C]')
m.HasSubstructMatch(patt)
>True



So when you kekulize, without using the clearAromaticFlags option, then
aromatic atoms will still only match 'a', not 'A', but the bonds will only
match '=' or '-', but not ':'  (they will also match '@' or '~', but that's
beside the point here)

As Peter mentions, by default if you read in a kekulized SMILES string, the
mol you create will not be kekulized, but it sounds like you are
intentionally kekulizing before doing substructure matching.



Jason Biggs


On Fri, Sep 8, 2017 at 5:19 PM, James T. Metz via Rdkit-discuss <
rdk...@li...> wrote:

> Hello,
>
>     Suppose I read in the SMILES of an aromatic molecule e.g., for
> benzene
>
>     c1ccccc1
>
>     I then want to convert the molecule to a Kekule representation and
> then perform various SMARTS pattern recognition e.g.
>
>     [C]=[C]-[C]
>
>     I have tried various Kekule commands in RDkit, but I can not figure
> out how to (or if it is possible) to recognize a SMARTS pattern for
> a portion of a molecule which is aromatic, but is currently being
> stored as a Kekule structure.
>
>     Also, is it possible to generate and store more than one Kekule
> form in RDkit?
>
>     Thank you.
>
>     Regards,
>     Jim Metz
>
>
>
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