Original scientific paper

https://doi.org/10.5562/cca3807

Automorphism Groups of Alkane Graphs

Kurt Varmuza orcid.org/0000-0002-3534-4001 ; Institute of Statistics and Mathematical Methods in Economics / Computational Statistics, Vienna University of Technology, Vienna, Austria
Matthias Dehmer ; Institute for Bioinformatics and Translational Research, UMIT, Eduard Wallnöfer Zentrum, Hall in Tyrol, Austria
Frank Emmert-Streib ; Predictive Society and Data Analytics Lab, Faculty of Information Technology and Communication Sciences, Tampere University, Tampere, Finland
Peter Filzmoser ; Institute of Statistics and Mathematical Methods in Economics / Computational Statistics, Vienna University of Technology, Vienna, Austria

Abstract

The complete set of 618047 isomers of the alkanes with 4 to 20 carbon atoms has been created. From all isomers the automorphism groups have been calculated and evaluated in terms of size, number of asymmetric carbon atoms, and numeric properties of atom and bond orbits. The presence of a symmetric bond is related to the number of atom and bond orbits. Molecular descriptors based on automorphism data have been studied, including the known symmetry index, an entropy measure and the root of an orbit polynomial. These descriptors are closely related to the presence of symmetric substructures. The prediction performance of QSPR models for three molecular properties of alkanes and using binary substructure descriptors, is improved by adding descriptors based on automorphism data.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

alkane isomers; automorphism groups; molecular descriptors; symmetry; orbit polynomial; QSPR models; PLS; repeated double cross validation

Hrčak ID:

269953

URI

https://hrcak.srce.hr/269953

Publication date:

28.6.2021.

Visits: 1.389 *