title: A correlation for 1,9-decadiene/water partition coefficients.
abstract: An important series of papers by Xiang, Anderson, and coworkers has established the strong correlation between phospholipid bilayer membrane permeability and the 1,9-decadiene/water partition coefficient over a wide range of compounds, elevating the importance of K(decadiene/w) as a predictor of molecular bioavailability. On the basis of a 58-point dataset developed by these authors, this research note develops an optimal correlation predicting log(10) K(decadiene/w) in terms of the octanol/water partition coefficient and four of the Abraham solvation parameters, namely A (hydrogen bond acidity), S (polarity/polarizability), E (excess molar refraction), and V (McGowan characteristic volume). The fitted dataset is described to within a root-mean-square error of 0.42, and the probable error in making a prediction for a compound not present therein is 0.49. It is shown that this correlation error for K(decadiene/w) is the dominant source of uncertainty in applying a comprehensive new model of phospholipid bilayer membrane permeability developed in a companion paper (Nitsche and Kasting, submitted for publication), which superposes the effects of molecular size and lipid density upon the decadiene lipophilicity scale. Thus, more experimental studies to augment the limited existing database on K(decadiene/w) are called for.
authors.affiliation: Department of Chemical and Biological Engineering, University at Buffalo, State University of New York, Buffalo, New York 14260-4200, USA.
authors.forename: Johannes M
authors.initials: JM
authors.lastname: Nitsche
authors.forename: Gerald B
authors.initials: GB
authors.lastname: Kasting
mesh_terms: D003198:Computer Simulation; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D008055:Lipids / Q000737:chemistry*; D008567:Membranes, Artificial; D008956:Models, Chemical; D015233:Models, Statistical; D008970:Molecular Weight; D015999:Multivariate Analysis; D000442:Octanols / Q000737:chemistry; D010539:Permeability; D012044:Regression Analysis; D035501:Uncertainty; D014867:Water / Q000737:chemistry*
chemical_list: D008055:Lipids; D008567:Membranes, Artificial; D000442:Octanols; D014867:Water; C457799:1,9-decadiene