title: Prediction of retention characteristics of heterocyclic compounds.
abstract: The CORAL software ( http://www.insilico.eu/coral ) was used to build up quantitative structure-property relationships (QSPRs) for the retention characteristics of 93 derivatives of three groups of heterocyclic compounds: 2-phenyl-1,3-benzoxazoles, 4-benzylsulfanylpyridines, and benzoxazines. The QSPRs are one-variable models based on the optimal descriptors calculated from the molecular structure represented by simplified molecular input-line entry systems (SMILES). Each symbol (or two undivided symbols) of SMILES is characterized by correlation weight. The optimal descriptor is the sum of the correlation weights. The numerical data on the correlation weights were calculated with the Monte Carlo method by the manner which provides best correlation between endpoint and optimal descriptor for the calibration set. The predictive ability of the model is checked with the validation set (compounds invisible during building up of the model). The approach has been checked with three random splits into the training, calibration, and validation sets: all models have apparent predictive potential. The mechanistic interpretation of the molecular features extracted from SMILES as the promoters of increase or decrease of examined endpoints is suggested.
authors.affiliation: Faculty of Science, Department of Analytical Chemistry, Charles University in Prague, Hlavova 8, 128 43, Prague 2, Czech Republic.
authors.forename: Karel
authors.initials: K
authors.lastname: Nesměrák
authors.affiliation: Laboratory of Environmental Chemistry and Toxicology, IRCCS-Istituto di Ricerche Farmacologiche Mario Negri, Via La Masa 19, 20156, Milan, Italy. andrey.toropov@marionegri.it.
authors.forename: Andrey A
authors.initials: AA
authors.lastname: Toropov
authors.affiliation: Laboratory of Environmental Chemistry and Toxicology, IRCCS-Istituto di Ricerche Farmacologiche Mario Negri, Via La Masa 19, 20156, Milan, Italy.
authors.forename: Alla P
authors.initials: AP
authors.lastname: Toropova
authors.affiliation: Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ankara University, 06100, Ankara, Tandogan, Turkey.
authors.forename: Ilkay
authors.initials: I
authors.lastname: Yildiz
authors.affiliation: Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ankara University, 06100, Ankara, Tandogan, Turkey.
authors.forename: Ismail
authors.initials: I
authors.lastname: Yalcin
authors.affiliation: Faculty of Science, Department of Analytical Chemistry, Charles University in Prague, Hlavova 8, 128 43, Prague 2, Czech Republic.
authors.forename: Marketa
authors.initials: M
authors.lastname: Brozikova
authors.affiliation: Faculty of Pharmacy, Department of Inorganic and Organic Chemistry, Charles University in Prague, Heyrovskeho 1203, 500 05, Hradec Kralove, Czech Republic.
authors.forename: Vera
authors.initials: V
authors.lastname: Klimešová
authors.affiliation: Faculty of Pharmacy, Department of Inorganic and Organic Chemistry, Charles University in Prague, Heyrovskeho 1203, 500 05, Hradec Kralove, Czech Republic.
authors.forename: Karel
authors.initials: K
authors.lastname: Waisser
keywords: CORAL software; Monte Carlo method; QSPR; Retention factor; SMILES