caa a22 4500 467939055 CHVBK 20180406153006.0 cr unu---uuuuu 170328e20061001xx s 000 0 eng 10.1007/s10822-006-9089-4 doi (NATIONALLICENCE)springer-10.1007/s10822-006-9089-4 Bond-based global and local (bond, group and bond-type) quadratic indices and their applications to computer-aided molecular design. 1. QSPR studies of diverse sets of organic chemicals [Elektronische Daten] [Yovani Marrero-Ponce, Francisco Torrens, Ysaias Alvarado, Richard Rotondo] The concept of atom-based quadratic indices is extended to a series of molecular descriptors (MDs) (both total and local) based on adjacency between edges. The kth edge-adjacency matrix (E k ) denotes the matrix of bond-based quadratic indices (non-stochastic) with respect to the canonical basis set. The kth "stochastic” edge-adjacency matrix, ES k , is here proposed as a new molecular representation easily calculated from E k . Then, the kth stochastic bond-based quadratic indices are calculated using ES k as operators of quadratic transformations. The study of six representative physicochemical properties of octane isomers was used to compare the ability of both series of MDs to produce significant quantitative structure-property relationship (QSPR) models. Moreover, the general performance of the new MDs in this QSPR study has been evaluated with respect to other 2D/3D well-known sets of indices and the obtained results shown a quite satisfactory behavior of the present method. The novel bond-level MDs were also used for the description and prediction of the boiling point of 28 alkyl-alcohols and to the modeling of the specific rate constant (logk) of 34 derivatives of 2-furylethylenes. These models were statistically significant and showed very good stability to data variation in leave-one-out (LOO) cross-validation experiment. The comparison with other approaches (edge- and vertices-based connectivity indices, total and local spectral moments, and quantum chemical descriptors as well as E-state/biomolecular encounter parameters) expose a good behavior of our method in this QSPR studies. The approach described in this report appears to be a very promising structural invariant, useful for QSPR/QSAR studies, similarity/diversity analysis, and computer-aided "rational” molecular (drug) design. Springer Science+Business Media, LLC, 2006 TOMOCOMD-CARDD software nationallicence Non-stochastic and stochastic bond-based quadratic indices nationallicence Edge-adjacency matrix nationallicence Stochastic matrix nationallicence QSPR study nationallicence QSPR model nationallicence Physicochemical property nationallicence Octane isomers nationallicence Alkyl-alcohol nationallicence 2-Furylethylene nationallicence Marrero-Ponce Yovani Unit of Computer-Aided Molecular ‘Biosilico' Discovery and Bioinformatic Research (CAMD-BIR Unit), Faculty of Chemistry-Pharmacy, Central University of Las Villas, 54830, Santa Clara, Villa Clara, Cuba aut Torrens Francisco Institut Universitari de Ciència Molecular, Universitat de València, Edifici d'Instituts de Paterna, P.O. Box 22085, E-46071, València, Spain aut Alvarado Ysaias Laboratorio de Electrónica Molecular, Departamento de Química, Modulo II, grano de Oro, Facultad Experimental de Ciencias, La Universidad del Zulia (LUZ), Maracaibo, Venezuela aut Rotondo Richard Mediscovery, Inc. Suite 1050, 601 Carlson Parkway, 55305, Minnetonka, MN, USA aut Journal of Computer-Aided Molecular Design Kluwer Academic Publishers 20/10-11(2006-10-01), 685-701 0920-654X 20:10-11<685 2006 20 10822 https://doi.org/10.1007/s10822-006-9089-4 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10822-006-9089-4 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Marrero-Ponce Yovani Unit of Computer-Aided Molecular ‘Biosilico' Discovery and Bioinformatic Research (CAMD-BIR Unit), Faculty of Chemistry-Pharmacy, Central University of Las Villas, 54830, Santa Clara, Villa Clara, Cuba aut NATIONALLICENCE 700 1- Torrens Francisco Institut Universitari de Ciència Molecular, Universitat de València, Edifici d'Instituts de Paterna, P.O. Box 22085, E-46071, València, Spain aut NATIONALLICENCE 700 1- Alvarado Ysaias Laboratorio de Electrónica Molecular, Departamento de Química, Modulo II, grano de Oro, Facultad Experimental de Ciencias, La Universidad del Zulia (LUZ), Maracaibo, Venezuela aut NATIONALLICENCE 700 1- Rotondo Richard Mediscovery, Inc. Suite 1050, 601 Carlson Parkway, 55305, Minnetonka, MN, USA aut NATIONALLICENCE 773 0- Journal of Computer-Aided Molecular Design Kluwer Academic Publishers 20/10-11(2006-10-01), 685-701 0920-654X 20:10-11<685 2006 20 10822 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer