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Novel 2D TOMOCOMD-CARDD molecular descriptors: Atom-based stochastic and non-stochastic bilinear indices and their QSPR applications

Abstract:

Novel atom-based molecular descriptors (MDs) based on a bilinear map similar to use defined in linear algebra are presented. These MDs, called "local (atom, group and atom-type) and total (global) bilinear indices", are proposed here as a new molecular parametrization easily calculated from the 2D molecular information. The proposed non-stochastic and stochastic molecular fingerprints try to match molecular structure provided by the molecular topology by using the kth non-stochatic (Marrero-Ponce, J Chem Inf Comput Sci 44, 2010, 2004; Marrero-Ponce, Molecules 8, 687, 2003) and stochastic (Marrero-Ponce, et al. J Mol Struc (Theochem) 717, 67, 2005; Marrero-Ponce, Castillo-Garit, J Comput-Aided Mol Design 19, 369, 2005) graph-theoretic electronic-density matrices, M k and S k , respectively. That is to say, the kth non-stochastic and stochastic bilinear indices are calculated using M k and S k as matrix operators of bilinear transformations. Moreover, chemical information is codified by using different pair combinations of atomic weightings (atomic mass, polarizability, van der Waals volume, and electronegativity). The pbkp_rediction ability in Quantitative Structure-Property Relationships (QSPR) of the new MDs was tested by analysing regressions of these MDs for six selected properties of octane isomers. It was clearly demonstrated that pbkp_rediction ability was higher than those showed by other 2D/3D well-known sets of MDs. The obtained results suggest that with the present method it is possible to obtain a good estimation of these physicochemical properties for octanes. The approach described in the present report appears to be a prominent method to find quantitative models for description of physicochemical and biological properties. © 2008 Springer Science+Business Media, LLC.