Shannon's, mutual, conditional and joint entropy information indices: Generalization of global indices defined from local vertex invariants

Stephen J. Barigye, Yovani Marrero-Ponce, Oscar Martínez Santiago, Yoan Martínez López, Facundo Pérez-Giménez, Francisco Torrens

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

26 Citas (Scopus)


A new mathematical approach is proposed in the definition of molecular descriptors (MDs) based on the application of information theory concepts. This approach stems from a new matrix representation of a molecular graph (G) which is derived from the generalization of an incidence matrix whose row entries correspond to connected subgraphs of a given G, and the calculation of the Shannon's entropy, the negentropy and the standardized information content, plus for the first time, the mutual, conditional and joint entropy-based MDs associated with G. We also define strategies that generalize the definition of global or local invariants from atomic contributions (local vertex invariants, LOVIs), introducing related metrics (norms), means and statistical invariants. These invariants are applied to a vector whose components express the atomic information content calculated using the Shannon's, mutual, conditional and joint entropy-based atomic information indices. The novel information indices (IFIs) are implemented in the program TOMOCOMD-CARDD. A principal component analysis reveals that the novel IFIs are capable of capturing structural information not codified by IFIs implemented in the software DRAGON. A comparative study of the different parameters (e.g. subgraph orders and/or types, invariants and class of MDs) used in the definition of these IFIs reveals several interesting results. The mutual entropy-based indices give the best correlation results in modeling of a physicochemical property, namely the partition coefficient of the 34 derivatives of 2-furylethylenes, among the classes of indices investigated in this study. In a comparison with classical MDs it is demonstrated that the new IFIs give good results for various QSPR models.

Idioma originalInglés
Páginas (desde-hasta)164-183
Número de páginas20
PublicaciónCurrent Computer-Aided Drug Design
EstadoPublicada - 2013
Publicado de forma externa


Profundice en los temas de investigación de 'Shannon's, mutual, conditional and joint entropy information indices: Generalization of global indices defined from local vertex invariants'. En conjunto forman una huella única.

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