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On the similarity of chemical structures
Author(s) -
Barysz M.,
Trinajstić N.,
Knop J. V.
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560240849
Subject(s) - similarity (geometry) , structural similarity , chemical similarity , index (typography) , mathematics , simple (philosophy) , topological index , quantitative structure–activity relationship , computational chemistry , chemistry , biological system , computer science , artificial intelligence , stereochemistry , biology , philosophy , epistemology , world wide web , image (mathematics)
A novel criterion for structural similarity is proposed. This similarity criterion is expressed as a numerical index. The derivation of the similarity index is based on the information theoretical concept of the gain of information, while chemical structures are represented by simple molecular graphs. The similarity index is applied to N ‐substituted 2‐amino‐tetralins, with or without hydroxyl groups at the 5 and 6 or 6 and 7 positions, which exhibit dopaminergic agonistic potency. The similarity index classifies these structures into three groups. This classification roughly follows the biological activities of aminotetralins.