Machine Learning Classification of Chirality and Optical Rotation Using a Simple One-Hot Encoded Cartesian Coordinate Molecular Representation.

Journal: Journal of chemical information and modeling
PMID:

Abstract

Absolute stereochemical configurations and optical rotations were computed for 121,416 molecular structures from the QM9 quantum chemistry data set using density functional theory. A representation for the molecules was developed using Cartesian coordinate geometries and encoded atom types to serve as input for various machine learning algorithms. Classifiers were developed and trained to predict the chirality and signs of optical rotations using a variety of machine learning methods. These methods are compared, and the results demonstrate that machine learning is a viable tool for making predictions of the stereochemical properties of molecules.

Authors

  • Yilin Zhou
    Center for Integrated Research Computing, University of Rochester, Rochester, New York 14627, United States.
  • Haoran Zhu
    Center for Integrated Research Computing, University of Rochester, Rochester, New York 14627, United States.
  • Yijie Yuan
    Center for Integrated Research Computing, University of Rochester, Rochester, New York 14627, United States.
  • Ziyu Song
    Center for Integrated Research Computing, University of Rochester, Rochester, New York 14627, United States.
  • Brendan C Mort
    Center for Integrated Research Computing, University of Rochester, Rochester, New York 14627, United States.