Abstract
AbstractThe KOWWIN and ALOGPS octanol-water partition coefficient (K~ow~) estimation software programs were compared for their capacity to accurately predict log K~ow~ values of 1545 organic compounds on the publicly available Domestic Substances List (DSL) from Environment Canada for which experimental data is available. Approximately equivalent log K~ow~ error statistics were observed between KOWWIN and ALOGPS against available experimental data. Substantial predictive differences were observed between the two programs for 6529 compounds not having experimental K~ow~ data on the Canadian DSL. Predictive differences of up to 40 log K~ow~ units were found between KOWWIN and ALOGPS, and in some cases, the discrepancies were sufficiently large that strongly opposing hydrophobicity classifications were obtained.
Highlights
Octanol-water partition coefficients (Kow) are widely used in environmental and biological chemistry to predict and understand the partitioning behavior of neutral organic compounds and their salts into a range of organic materials
Naming formalisms that all refer to the same structure; (2) failure to properly specify geometrical isomerism or stereochemistry (i.e., R/S), both of which could have been designated using the SMILES notation [5, 6] in this database; and (3) while the compound name suggests the log Kow value was determined/estimated for a salt, the SMILES formula indicates the molecular form, thereby making direct comparisons between experimental and estimated data invalid, and the use of the estimated data subject to significant uncertainty
From an initial sample of 1771 experimental log Kow values in the Canadian Domestic Substances List (DSL) listing, the removal of duplicate entries, errors, salts, and organosilicon compounds resulted in a reduced set of 1545 compounds (Appendix Table 1)
Summary
Octanol-water partition coefficients (Kow) are widely used in environmental and biological chemistry to predict and understand the partitioning behavior of neutral organic compounds and their salts into a range of organic materials. Comparison between experimentally obtained log Kow values and corresponding KOWWIN and ALOGPS estimates and errors. 3,4-dihydro-, 1,1-dioxide 1H-imidazole, 1-methylpropanedioic acid, dimethyl ester 2-pyrrolidinone, 1-ethyl2-oxazolidinone, 3-[[(5-nitro-2furanyl)methylene]amino]2-naphthacenecarboxamide, 4-(dimethylamino)1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12apentahydroxy-6-methyl-1,11-dioxo1H-purine-2,6-dione, 3,7-dihydro-1,3-dimethyl1H-imidazole-1-ethanol, 2-methyl-5-nitro5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8oxo-7-[(2-thienylacetyl)amino]2-propenal methane, dimethoxy6H-purine-6-thione, 1,7-dihydroformic acid, methyl ester ethanol, 2-chloro2-propen-1-amine oxirane, methylphenol, 4-aminoethanol, 2-(1-methylethoxy)thymidine, 3-azido-3-deoxy- 0.73 0.76 0.03 acetic acid ethyl ester 0.84 0.67 -0.17 propanoic acid, methyl ester 0.94 1.04 0.10 acetic acid, chloro-, ethyl ester
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