Prediction of aqueous solubility and the octanol-water partition coefficient for lipophilic organic compounds using molecular descriptors and physicochemical properties

M. St J. Warne, D. W. Connell, D. W. Hawker, G. Schüürmann

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The utility of thirty-nine molecular descriptors and physicochemical properties to model the solubility (S) and octanol-water partition coefficient (Kow) of thirty-one lipophilic organic compounds was assessed using least squares linear regression analysis. The modelling of Kow when all the compounds were treated together or in groups of structurally related compounds was adequate however, utility for prediction was greatly improved by separate treatment of ionizing and non-ionizing compounds. The log Kow values of the ionizing compounds could best be predicted by multi-parametric linear regression (MLR) equations utilising pKa and molecular weight. The linear regression equations for log S were not as significant as those for log Kow. Several novel molecular descriptors that yielded high correlation coefficients in linear regression equations were the approximate sigma electron density, radius of gyration and the first and second principle moments of inertia. Other useful properties were the sum of all absolute valency charges, density at 20°C, liquid density and pKa.

Original languageEnglish
Pages (from-to)877-888
Number of pages12
JournalChemosphere
Volume21
Issue number7
DOIs
Publication statusPublished - 1990
Externally publishedYes

Fingerprint

Octanols
physicochemical property
Organic compounds
partition coefficient
Linear regression
Solubility
Linear Models
organic compound
solubility
Water
prediction
inertia
Density of liquids
water
electron density
regression analysis
Charge density
Least-Squares Analysis
Regression analysis
Carrier concentration

ASJC Scopus subject areas

  • Environmental Engineering
  • Environmental Chemistry
  • Chemistry(all)
  • Pollution
  • Health, Toxicology and Mutagenesis

Cite this

Prediction of aqueous solubility and the octanol-water partition coefficient for lipophilic organic compounds using molecular descriptors and physicochemical properties. / Warne, M. St J.; Connell, D. W.; Hawker, D. W.; Schüürmann, G.

In: Chemosphere, Vol. 21, No. 7, 1990, p. 877-888.

Research output: Contribution to journalArticle

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