title: CORAL: QSPR model of water solubility based on local and global SMILES attributes.
abstract: Water solubility is an important characteristic of a chemical in many aspects. However experimental definition of the endpoint for all substances is impossible. In this study quantitative structure-property relationships (QSPRs) for negative logarithm of water solubility-logS (mol L(-1)) are built up for five random splits into the sub-training set (≈55%), the calibration set (≈25%), and the test set (≈20%). Simplified molecular input-line entry system (SMILES) is used as the representation of the molecular structure. Optimal SMILES-based descriptors are calculated by means of the Monte Carlo method using the CORAL software (http://www.insilico.eu/coral). These one-variable models for water solubility are characterized by the following average values of the statistical characteristics: n(sub_train)=725-763; n(calib)=312-343; n(test)=231-261; r(sub_train)(2)=0.9211±0.0028; r(calib)(2)=0.9555±0.0045; r(test)(2)=0.9365±0.0073; s(sub_train)=0.561±0.0086; s(calib)=0.453±0.0209; s(test)=0.520±0.0205. Thus, the reproducibility of statistical quality of suggested models for water solubility confirmed for five various splits.
authors.affiliation: Istituto di Ricerche Farmacologiche Mario Negri, 20156, Via La Masa 19, Milano, Italy. andrey.toropov@marionegri.it
authors.forename: Andrey A
authors.initials: AA
authors.lastname: Toropov
authors.forename: Alla P
authors.initials: AP
authors.lastname: Toropova
authors.forename: Emilio
authors.initials: E
authors.lastname: Benfenati
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Gini
authors.forename: Danuta
authors.initials: D
authors.lastname: Leszczynska
authors.forename: Jerzy
authors.initials: J
authors.lastname: Leszczynski
mesh_terms: D002138:Calibration; D004784:Environmental Monitoring / Q000379:methods*; D004785:Environmental Pollutants / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009010:Monte Carlo Method; D021281:Quantitative Structure-Activity Relationship; D015203:Reproducibility of Results; D012984:Software; D012995:Solubility
chemical_list: D004785:Environmental Pollutants