On the similarity of chemical structures
Maria Barysz, Nenad Trinajstić, J. V. Knop · International Journal of Quantum Chemistry · 2009
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.