TY - JOUR

T1 - Novel 2D TOMOCOMD-CARDD molecular descriptors

T2 - Atom-based stochastic and non-stochastic bilinear indices and their QSPR applications

AU - Marrero-Ponce, Yovani

AU - Torrens, Francisco

AU - García-Domenech, Ramón

AU - Ortega-Broche, Sadiel E.

AU - Zaldivar, Vicente Romero

N1 - Funding Information:
Acknowledgements Yovani Marrero-Ponce (M-P. Y) acknowledges the Valencia University (Spain) for kind hospitality during the second semester of 2007. M-P. Y thanks are given to the international relationships of the Valencia University for partial financial support as well as the program ‘Estades Temporals per an Investigadors Convidats’ for a fellowship to work at Valencia University (2007-2008). M-P. Y also thanks support from Spanish MEC (Project Reference: SAF2006-04698). F. T. acknowledges financial support from the Spanish MEC DGI (Project No. CTQ2004-07768-C02-01/BQU) and Generalitat Valenci-ana (DGEUI INF01-051 and INFRA03-047, and OCYT GRUPOS03-173. R.G.D. acknowledges financial support from Spanish Ministry of Health (Project FIS No. SAF2005/PI052128). Finally, but not less, M-P. Y thanks are given to the projects entitle “Strengthening postgraduate education and research in Pharmaceutical Sciences”. This project is funded by the Flemish Interuniversity Council (VLIR) of Belgium.

PY - 2008/10

Y1 - 2008/10

N2 - 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 prediction 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 prediction 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.

AB - 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 prediction 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 prediction 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.

KW - Genetic algorithm

KW - Non-stochastic and stochastic atom-based bilinear indices

KW - Octane isomers

KW - Physicochemical properties

KW - QSPR model

KW - TOMOCOMD-CARDD software

UR - http://www.scopus.com/inward/record.url?scp=51849153313&partnerID=8YFLogxK

U2 - 10.1007/s10910-008-9389-0

DO - 10.1007/s10910-008-9389-0

M3 - Artículo

AN - SCOPUS:51849153313

SN - 0259-9791

VL - 44

SP - 650

EP - 673

JO - Journal of Mathematical Chemistry

JF - Journal of Mathematical Chemistry

IS - 3

ER -