Event-based criteria in GT-STAF information indices: theory, exploratory diversity analysis and QSPR applications

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 inciden...

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Bibliographic Details
Published in:SAR and QSAR in environmental research 2013-01, Vol.24 (1), p.3-34
Main Authors: Barigye, S.J., Marrero-Ponce, Y., López, Y. Martínez, Santiago, O. Martínez, Torrens, F., Domenech, R. García, Galvez, J.
Format: Article
Language:English
Subjects:
Algorithms
Chemistry, Organic - methods
Cluster Analysis
Computational Biology - methods
Computer Graphics
conditional and joint entropy
Entropy
Ethylenes - chemistry
event
GT-STAF
Hydrophobic and Hydrophilic Interactions
Information Theory
Linear Models
magnitude criterion
Models, Theoretical
Molecular Structure
QSPR
Quantitative Structure-Activity Relationship
Shannon's, mutual
Software
TOMOCOMD-CARDD
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Summary: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.
ISSN:1062-936X
1029-046X
DOI:10.1080/1062936X.2012.728994