Estimation of Molecular Linear Free Energy Relation Descriptors Using a Group Contribution Approach

Abstract

Additive models for the estimation of Abraham's molecular descriptors R 2 , π 2 H , ΣR 2 H , Σβ 2 H , Σβ 2 O , and log L 16 have been developed. For five of the six descriptors, one set of 81 atom and functional group fragments is capable of reproducing experimentally derived results with correlation coefficients ranging from 0.95 to 0.99. However, one descriptor, ΣR 2 H , required an entirely separate set of 51 fragments to be developed, resulting in a correlation coefficient of 0.97. Of particular importance is the speed of calculation (approximately 700 molecules/min), allowing so-called "high-throughput screening". Several applications of this model for molecules containing intramolecular interactions are discussed.

Characterization of the sorption of gaseous and organic solutes onto polydimethyl siloxane solid-phase microextraction surfaces using the Abraham model

“…Solute descriptors used in the present study are all based on experimental data. There is also commercial software [56] and several published estimation schemes [57][58][59][60] for calculating the numerical values of solute descriptors from molecular structural information if one is unable to find the necessary partition, solubility, and/or chromatographic data.…”

Commentary on “Measurement and Correlation of the Solubility of Telmisartan (Form A) in Nine Different Solvents from 277.85 to 338.35 K”

“…Correctly calculated, the McGowan volume for telmisartan is V = 3.9785. The E solute descriptor can be estimated by the PharmaAlgorithm software [3], which is based on molecular structure considerations using fragment group values [4,5], or calculated using a measured value (liquid solute) or an estimated value (solid solute) for the solute's refractive index. The refractive index of solid solutes can be estimated using the (free) ACD software [6].…”

Prediction of Cytochrome P450 3A4, 2D6, and 2C9 Inhibitors and Substrates by Using Support Vector Machines

“…These descriptors can be divided into 18 classes including 47 constitutional descriptors, 70 geometrical descriptors, 266 topological descriptors, 150 RDF descriptors, 38 21 molecular walk counts, 39 160 3D-MoRSE descriptors, 40 64 BCUT descriptors, 41 99 WHIM descriptors, 42 21 Galvez topological charge indices, 43 197 GETAWAY descriptors, 44 96 2D autocorrelations, 121 functional groups, 14 charge descriptors, 120 atom-centered descriptors, 4 aromaticity indices, 45 3 empirical descriptors, 41 Randic molecular profiles, 46 and 3 molecular properties. Moreover, an additional set of 105 electrotopological state descriptors 47 and 5 linear solvation energy relationship descriptors 48 were computed by using our own developed code. Our code has been tested on a number of compounds used in earlier studies to ensure the accuracy of the computed descriptors.…”