Details zur Publikation

Kategorie Textpublikation
Referenztyp Zeitschriften
DOI 10.1021/ci1001179
Titel (primär) Tautomer identification and tautomer structure generation based on the InChI code
Autor Thalheim, T.; Vollmer, A.; Ebert, R.-U.; Kühne, R. ORCID logo ; Schüürmann, G.
Quelle Journal of Chemical Information and Modeling
Erscheinungsjahr 2010
Department OEC
Band/Volume 50
Heft 7
Seite von 1223
Seite bis 1232
Sprache englisch
Abstract An algorithm is introduced that enables a fast generation of all possible prototropic tautomers resulting from the mobile H atoms and associated heteroatoms as defined in the InChI code. The InChI-derived set of possible tautomers comprises (1,3)-shifts for open-chain molecules and (1,n)-shifts (with n being an odd number >3) for ring systems. In addition, our algorithm includes also, as extension to the InChI scope, those larger (1,n)-shifts that can be constructed from joining separate but conjugated InChI sequences of tautomer-active heteroatoms. The developed algorithm is described in detail, with all major steps illustrated through explicit examples. Application to 72500 organic compounds taken from EINECS (European Inventory of Existing Commercial Chemical Substances) shows that around 11% of the substances occur in different heteroatom-prototropic tautomeric forms. Additional QSAR (quantitative structure-activity relationship) predictions of their soil sorption coefficient and water solubility reveal variations across tautomers up to more than two and 4 orders of magnitude, respectively. For a small subset of nine compounds, analysis of quantum chemically predicted tautomer energies supports the view that among all tautomers of a given compound, those restricted to H atom exchanges between heteroatoms usually include the thermodynamically most stable structures.
dauerhafte UFZ-Verlinkung
Thalheim, T., Vollmer, A., Ebert, R.-U., Kühne, R., Schüürmann, G. (2010):
Tautomer identification and tautomer structure generation based on the InChI code
J. Chem Inf. Model. 50 (7), 1223 - 1232 10.1021/ci1001179