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Research Article

Representation of Molecular Configurations by CAST Coding Method

Hiroko Satoh,*^§^†^‡ Hiroyuki Koshino,*^§ Kimito Funatsu,^# and Tadashi Nakata^§

RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan, PRESTO, Japan Science and Technology Corporation, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan, and Department of Knowledge-Based Information Engineering, Toyohashi University of Technology, 1-1 Tempaku, Toyohashi, Aichi 441-8580, Japan

J. Chem. Inf. Comput. Sci., 2001, 41 (5), pp 1106–1112

DOI: 10.1021/ci000136g

Publication Date (Web): August 31, 2001

Corresponding authors phone: +81-3-4212-2579; e-mail: hsatoh@nii.ac.jp (Satoh) and phone: +81-48-462-1111 (ext. 3112); e-mail: koshino@postman.riken.go.jp (Koshino).

RIKEN (The Institute of Physical and Chemical Research).

†

PRESTO, Japan Science and Technology Corporation.

‡

Present address: National Institute of Informatics, 2-1-2 Hitotsubashi, Chiyoda-ku, Tokyo 101-8430, Japan.

Toyohashi University of Technology.

Abstract

A configurational CAST (CAnonical representation of STereochemistry) coding method, which represents relative and absolute configuration, is described. The configurational CAST codes are constructed by canonical rotation of the dihedral angles of the input structure before the CAST codes are assigned. Using the configurational CAST, configurational differences can be distinguished independently of conformational differences. Representation of enantiomers is also achieved by a mirror image conversion method. The CAST representation shows the distinctive characteristics of several diastereomers and conformers that were examined. The method clearly represents the differences in configurations. Applications to organic molecules having complex stereochemistry are also demonstrated.

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