title: Generalized Molecular Descriptors Derived From Event-Based Discrete Derivative.
abstract: In the present study, a generalized approach for molecular structure characterization is introduced, based on the relation frequency matrix (F) representation of the molecular graph and the subsequent calculation of the corresponding discrete derivative (finite difference) over a pair of elements (atoms). In earlier publications (22- 24), an unique event, named connected subgraphs, (based on the Kier-Hall's subgraphs) was systematically employed for the computation of the matrix F. The present report is a generalization of this notion, in which eleven additional events are introduced, classified in three categories, namely, topological (terminal paths, vertex path incidence, quantum subgraphs, walks of length k, Sach's subgraphs), fingerprints (MACCs, E-state and substructure fingerprints) and atomic contributions (Ghose and Crippen atom-types for hydrophobicity and refractivity) for F generation. The events are intended to capture diverse information by the generation or search of different kinds of substructures from the graph representation of a molecule. The discrete derivative over duplex atom relations are calculated for each event, and the resulting derivatives, local vertex invariants (LOVIs) are finally obtained. These LOVIs are subsequently employed as the basis for the calculation of global and local indices over groups of atoms (heteroatoms, halogens, methyl carbons, etc.), by using norms, means, statistics and classical algorithms as aggregator (fusion) operators. These indices were implemented in our house software DIVATI (Derivative Type Indices, a new module of TOMOCOMDCARDD system). DIVATI provides a friendly and cross-platform graphical user interface, developed in the Java programming language and is freely available at: http: //www.tomocomd.com. Factor analysis shows that the presented events are rather orthogonal and collect diverse information about the chemical structure. Finally, QSPR models were built to describe the logP and logK of 34 furylethylenes derivatives using the eleven events. Generally, the equations obtained according to these events showed high correlations, with the Sach's sub-graphs and Multiplicity events showing the best behavior in the description of logK (Q2 LOO value of 99.06%) and logP (Q2 LOO value of 98.1 %), respectively. These results show that these new eventbased indices constitute a powerful approach for chemoinformatics studies.
authors.forename: Oscar
authors.initials: O
authors.lastname: Martínez-Santiago
authors.forename: Reisel Millán
authors.initials: RM
authors.lastname: Cabrera
authors.affiliation: Computer-Aided Molecular "Biosilico" Discovery and Bioinformatic Research International Network (CAMD-BIR IN), Cumbayá, Quito, Ecuador. ymarrero@usfq.edu.ec.
authors.forename: Yovani
authors.initials: Y
authors.lastname: Marrero-Ponce
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Barigye
authors.forename: Huong
authors.initials: H
authors.lastname: Le-Thi-Thu
authors.forename: F Javier
authors.initials: FJ
authors.lastname: Torres
authors.forename: Cesar H
authors.initials: CH
authors.lastname: Zambrano
authors.forename: Ivan
authors.initials: I
authors.lastname: Yaber-Goenaga
authors.forename: Maykel
authors.initials: M
authors.lastname: Cruz-Monteagudo
authors.forename: Yoan Martínez
authors.initials: YM
authors.lastname: López
authors.forename: Facundo Pérez
authors.initials: FP
authors.lastname: Giménez
authors.forename: Francisco
authors.initials: F
authors.lastname: Torrens
mesh_terms: D000465:Algorithms; D005663:Furans / Q000737:chemistry*; D008956:Models, Chemical; D012984:Software
chemical_list: D005663:Furans