Algorithm for advanced canonical coding of planar chemical structures that considers stereochemical and symmetric information.
We describe a rigorous and fast algorithm for advanced canonical coding of planar chemical structures based on the algorithm of Faulon et al. (J. Chem. Inf. Comput. Sci. 2004, 44, 427-436). Our algorithm works well even for highly symmetric structures; moreover, an advantage of our algorithm includes providing a rigorous canonical numbering of atoms with a consideration of stereochemistry and recognizing symmetric moieties. The planar structural line notation with the canonical numbering is also fit for use with stereochemical line notation. These capabilities are usable for general purposes in chemical structural coding and are particularly essential for detecting equivalent atoms in NMR studies. This algorithm was implemented on a 13C NMR chemical shift prediction system CAST/CNMR. Applications of the algorithm to several organic compounds demonstrate the practical efficiency of the rigorous coding.
Koichi
Shungo
S
Graduate School of Information Science and Technology, University of Tokyo, Tokyo 113-8656, Japan.
Iwata
Satoru
S
Uno
Takeaki
T
Koshino
Hiroyuki
H
Satoh
Hiroko
H
D000465:Algorithms; D001185:Artificial Intelligence; D003198:Computer Simulation; D037741:Fullerenes / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008838:Microcomputers; D008958:Models, Molecular; D008968:Molecular Conformation; D012984:Software; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D037741:Fullerenes