TY - JOUR

T1 - Event-based criteria in GT-STAF information indices

T2 - Theory, exploratory diversity analysis and QSPR applications

AU - Barigye, S. J.

AU - Marrero-Ponce, Y.

AU - López, Y. Martínez

AU - Santiago, O. Martínez

AU - Torrens, F.

AU - Domenech, R. García

AU - Galvez, J.

N1 - Funding Information:
Y. Marrero-Ponce thanks the ‘Estades Temporals per an Investigadors Convidats’ program for a fellowship to work at Valencia University in 2012. The authors acknowledge the partial financial support from Spanish Ministry of Science and Innovation (MICINN, project reference: SAF2009-10399). Finally, this work was also partially supported by VLIR (Vlaamse InterUniversitaire Raad, Flemish Interuniversity Council, Belgium) under the IUC Program VLIR-UCLV.

PY - 2013/1

Y1 - 2013/1

N2 - Versatile event-based approaches for the definition of novel information theory-based indices (IFIs) are presented. An event in this context is the criterion followed in the "discovery" of molecular substructures, which in turn serve as basis for the construction of the generalized incidence and relations frequency matrices, Q and F, respectively. From the resultant F, Shannon's, mutual, conditional and joint entropy-based IFIs are computed. In previous reports, an event named connected subgraphs was presented. The present study is an extension of this notion, in which we introduce other events, namely: terminal paths, vertex path incidence, quantum subgraphs, walks of length k, Sach's subgraphs, MACCs, E-state and substructure fingerprints and, finally, Ghose and Crippen atom-types for hydrophobicity and refractivity. Moreover, we define magnitude-based IFIs, introducing the use of the magnitude criterion in the definition of mutual, conditional and joint entropy-based IFIs. We also discuss the use of information-theoretic parameters as a measure of the dissimilarity of codified structural information of molecules. Finally, a comparison of the statistics for QSPR models obtained with the proposed IFIs and DRAGON's molecular descriptors for two physicochemical properties log P and log K of 34 derivatives of 2-furylethylenes demonstrates similar to better predictive ability than the latter.

AB - Versatile event-based approaches for the definition of novel information theory-based indices (IFIs) are presented. An event in this context is the criterion followed in the "discovery" of molecular substructures, which in turn serve as basis for the construction of the generalized incidence and relations frequency matrices, Q and F, respectively. From the resultant F, Shannon's, mutual, conditional and joint entropy-based IFIs are computed. In previous reports, an event named connected subgraphs was presented. The present study is an extension of this notion, in which we introduce other events, namely: terminal paths, vertex path incidence, quantum subgraphs, walks of length k, Sach's subgraphs, MACCs, E-state and substructure fingerprints and, finally, Ghose and Crippen atom-types for hydrophobicity and refractivity. Moreover, we define magnitude-based IFIs, introducing the use of the magnitude criterion in the definition of mutual, conditional and joint entropy-based IFIs. We also discuss the use of information-theoretic parameters as a measure of the dissimilarity of codified structural information of molecules. Finally, a comparison of the statistics for QSPR models obtained with the proposed IFIs and DRAGON's molecular descriptors for two physicochemical properties log P and log K of 34 derivatives of 2-furylethylenes demonstrates similar to better predictive ability than the latter.

KW - GT-STAF

KW - QSPR

KW - Shannon's, mutual

KW - TOMOCOMD-CARDD

KW - cluster analysis

KW - conditional and joint entropy

KW - event

KW - magnitude criterion

UR - http://www.scopus.com/inward/record.url?scp=84871224613&partnerID=8YFLogxK

U2 - 10.1080/1062936X.2012.728994

DO - 10.1080/1062936X.2012.728994

M3 - Artículo

C2 - 23066866

AN - SCOPUS:84871224613

SN - 1062-936X

VL - 24

SP - 3

EP - 34

JO - SAR and QSAR in Environmental Research

JF - SAR and QSAR in Environmental Research

IS - 1

ER -