Ebert, R-U

Kühne, R

Schüürmann, G

Thalheim, Torsten

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Thalheim Torsten

Ebert R-U

Kühne R

Schüürmann G

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Journal of Cheminformatics

A Branch-and-Bound approach for tautomer enumeration

Torsten Thalheim

R-U Ebert

R Kühne

G Schüürmann

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Springer - Publisher Connector

ORAL PRESENTATION Open Access
A Branch-and-Bound approach for
tautomer enumeration
Torsten Thalheim*, R-U Ebert, R Kühne, G Schüürmann
From 5th German Conference on Cheminformatics: 23. CIC-Workshop
Goslar, Germany. 8-10 November 2009
For molecules with mobile H atoms, the result of quan-
titative structure-activity relationships (QSARs) depends
on the position of the respective hydrogen atoms. Thus
to obtain reliable results, tautomerism needs to be taken
into account.
In the last years, many approaches were introduced to
achieve this. In this work we present a further develop-
ment of our previous algorithm based on InChI-layers.
While the InChI ansatz supports only heteroatom-tauto-
merism, we suggest an extension regarding carbon
atoms too. Whereas with other tautomer generating
algorithms the hydrogen shifts are based on pattern-
rules, we try to overcome the rule constriction and
evolve a more common solution. The advantage of our
approach is quite simple. Due to the avoidance of a rule
system with its necessity for exceptions to the rules, we
can apply our solution to any kind of tautomerism
definition.
We set up a Branch-and-Bound approach, which is
optimized to generate a complete enumeration of all
tautomers, with regard to a certain definition, from any
structure. With few and easy decisions like symmetry
detection, we avoid a lot of calculation overhead. Deci-
sions with significant influence on the algorithm effi-
ciency are made as early as possible.
We have set up several kinds of tautomer definitions
and derived a stable definition covering the major kinds
of protropic tautomerism. Furthermore we analyzed,
what expenditure of time for large databases (case study:
more than 70,000 entries) is needed to investigate which
structures have tautomers and which not for more than
99% of the database entries.
This study has been financially supported by the EU
project OSIRIS (IP, contract no. 037017).
Published: 4 May 2010
doi:10.1186/1758-2946-2-S1-O8
Cite this article as: Thalheim et al.: A Branch-and-Bound approach for
tautomer enumeration. Journal of Cheminformatics 2010 2(Suppl 1):O8.
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Thalheim et al. Journal of Cheminformatics 2010, 2(Suppl 1):O8
http://www.jcheminf.com/content/2/S1/O8
© 2010 Thalheim et al; licensee BioMed Central Ltd.


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A Branch-and-Bound approach for tautomer enumeration

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