Deriving a quantitative chirality measure from molecular similarity indices.
A versatile new method has been developed as a continuous symmetry measure for chiral compounds. The application of principal component analysis (PCA) to the complete N x N pairwise similarity matrices (electrostatic potential and shape indices) of a series of dihydropyridine calcium channel antagonists allowed to single out a chirality component and to compute a chirality score in terms of the between-enantiomers difference on the component value. The possibility to have chirality defined continuously at the series level could be of importance in eudismic analyses where the relative potency of two enantiomers is studied as well as in QSAR studies dealing with chiral molecules in order to improve the power of the generated models.
Benigni
R
R
Laboratorio di Tossicologia Comparata ed Ecotossicologia and Laboratorio di Chimica del Farmaco, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161 Rome, Italy.
Cotta-Ramusino
M
M
Gallo
G
G
Giorgi
F
F
Giuliani
A
A
Varì
M R
MR
D002121:Calcium Channel Blockers / Q000737:chemistry; D004095:Dihydropyridines / Q000737:chemistry; D021281:Quantitative Structure-Activity Relationship; D013237:Stereoisomerism
D002121:Calcium Channel Blockers; D004095:Dihydropyridines