Tautomer distribution prediction fails on phthalocyanine

Greetings!

 

Attempts to predict tautomer distribution fails with the following SMILES string (phthalocyanine):

N1C2=NC3=NC(=NC4=C5C=CC=CC5=C(N4)N=C4N=C(N=C1C1=CC=CC=C21)C1=CC=CC=C41)C1=CC=CC=C31

No distribution is calculated either via GUI or cxcalc.

 

Any assistance would greatly appreciated. :)

Hi,

testing these problems I found the following results, see screenshots.

1) Pasting the SMILES into MarvinSketch produces the attached formula. There are several wrong double bonds, and what is the meaning of the wedge bonds ?

2) Calculating tautomers here produces 26 formulas. But no % distribution is shown.

Something goes wrong here.

Best regards, Hans-Ulrich

Hi Hans-Ulrich,

So I'm not quite sure about the incorrect bonds you speak of - they all appear to be correct from what I can tell.  I don't think there are any wedge bonds in this SMILES string from what I can see?

Thank you for all of your help,

Kind regards,

Trevor

Hi Trevor,

I mean the three "zig-zag"-bonds in the attached screenshot image "Pasting SMILES to MarvinSketch".

What is the meaning of these bonds I have called "wedge bonds" ?

And two rings are in wrong positions, too.

Kind regards, Hans-Ulrich

Hi,

There are  many bugs  with this structure. The Wedge bond , the graphic representation of the  rings, and the  tautomer generation.

 

The tautomer generation problem will be fixed in the upcoming release of 5.10.1.

I attached 2 figures to show the "way"  for generating the right structures.

Thank you for dealing with this problem.

Jozsi

We have registered the 2D clean issue as a bug.

The tautomer generation issue is fixed.

Miklos

Hi,

I usually clean 3D first and then 2D that also solves issues, and 4 tautomers are created. No Problem.

Tobias