Prediction of Partition Coefficients (LOG P oct) Using Autocorrelation Descriptors

Abstract A backpropagation neural network model, implemented in AUTOLOGP (Version 4.0), was developed for estimating the n-octanol/water partition coefficient of organic molecules from their structure described by means of a modified autocorrelation method. The advantages of the autocorrelation method, which allows the description of any kind of molecules by means of computerized molecular descriptors presenting a physicochemical meaning, were emphasized through the simulation performances obtained with AUTOLOGP (Version 4.0) and from a comparative study involving two regression models derived from various topological indices.

[1]  Patrick Camilleri,et al.  A surface area approach to determination of partition coefficients , 1988 .

[2]  J. Devillers,et al.  Estimating n-Octanol/Water Partition Coefficients from the Autocorrelation Method , 1995 .

[3]  M. Harnisch,et al.  Relationship between log Pow, shake-flask values and capacity factors derived from reversed-phase high-performance liquid chromatography for n-alkylbenzenes and some oecd reference substances , 1983 .

[4]  Joop L. M. Hermens,et al.  Modeling octanol/water partition coefficients by molecular topology: chlorinated benzenes and biphenyls , 1993 .

[5]  A. Leo,et al.  Substituent constants for correlation analysis in chemistry and biology , 1979 .

[6]  J. Devillers,et al.  Practical applications of quantitative structure-activity relationships (QSAR) in environmental chemistry and toxicology , 1990 .

[7]  Gilles Klopman,et al.  Calculation of partition coefficients by the charge density method , 1981 .

[8]  Shaomeng Wang,et al.  Computer Automated log P Calculations Based on an Extended Group Contribution Approach , 1994, J. Chem. Inf. Comput. Sci..

[9]  W. Meylan,et al.  Atom/fragment contribution method for estimating octanol-water partition coefficients. , 1995, Journal of pharmaceutical sciences.

[10]  L. Burkhard,et al.  Evaluation of reverse phase liquid chromatography/mass spectrometry for estimation of n-octanol/water partition coefficients for organic chemicals , 1985 .

[11]  M Chastrette,et al.  Trends in structure-odor relationships. , 1997, SAR and QSAR in environmental research.

[12]  A. Ghose,et al.  Atomic Physicochemical Parameters for Three‐Dimensional Structure‐Directed Quantitative Structure‐Activity Relationships I. Partition Coefficients as a Measure of Hydrophobicity , 1986 .

[13]  P. Broto,et al.  Molecular structures: perception, autocorrelation descriptor and sar studies: system of atomic contributions for the calculation of the n-octanol/water partition coefficients , 1984 .

[14]  C. Eadsforth.  Application of reverse-phase h.p.l.c. for the determination of partition coefficients† , 1986 .

[15]  O. Hutzinger,et al.  Reversed-phase thin-layer chromatography of polynuclear aromatic hydrocarbons and chlorinated biphenyls , 1982 .

[16]  Subhash C. Basak,et al.  A Comparative Study of Topological and Geometrical Parameters in Estimating Normal Boiling Point and Octanol/Water Partition Coefficient , 1996, J. Chem. Inf. Comput. Sci..

[17]  S. Hirono,et al.  Simple Method of Calculating Octanol/Water Partition Coefficient. , 1992 .

[18]  A. Hopfinger,et al.  Application of SCAP to drug design. 1. Prediction of octanol-water partition coefficients using solvent-dependent conformational analyses. , 1976, Journal of medicinal chemistry.

[19]  J. Devillers,et al.  Strengths and Weaknesses of the Backpropagation Neural Network in QSAR and QSPR Studies , 1996 .

[20]  H. Govers,et al.  Determination of n-octanol/water partition coefficients of tetrachlorobenzyltoluenes individually and in a mixture by the slow stirring method , 1994 .

[21]  J. Devillers,et al.  A predictive correlation for the acute toxicity of organic pollutants to , 1988 .

[22]  J. Devillers,et al.  Use of a Backpropagation Neural Network and Auto-correlation Descriptors for Predicting the Biodegradation of Organic Chemicals , 1996 .

[23]  Utilisation des descripteurs moléculaires d'autocorrélation dans les études quantitatives du type structure-écotoxicité , 1987 .

[24]  D. Mackay,et al.  Linear solvation energy relationships. 44. Parameter estimation rules that allow accurate prediction of octanol/water partition coefficients and other solubility and toxicity properties of polychlorinated biphenyls and polycyclic aromatic hydrocarbons. , 1988, Environmental science & technology.

[25]  A. D. Re,et al.  Relationships of Pesticide Octanol/Water Partition Coefficients to Their Physicochemical Properties , 1993 .

[26]  J. Devillers,et al.  Comparison of BCF models based on log P , 1996 .

[27]  Michele M. Miller,et al.  Generator Columns and High Pressure Liquid Chromatography for Determining Aqueous Solubilities and Octanol-Water Partition Coefficients of Hydrophobic Substances. , 1981, Journal of research of the National Bureau of Standards.

[28]  Luhua Lai,et al.  A New Atom-Additive Method for Calculating Partition Coefficients , 1997, J. Chem. Inf. Comput. Sci..

[29]  Gerald J. Niemi,et al.  Prediction of octanol/water partition coefficient ( K OW ) with algorithmically derived variables , 1992 .

[30]  Yoshihiro Kudo,et al.  Automatic log P estimation based on combined additive modeling methods , 1990, J. Comput. Aided Mol. Des..

[31]  D Zakarya,et al.  Quantitative structure-biodegradability relationships (QSBRs) using modified autocorrelation method (MAM). , 1993, SAR and QSAR in environmental research.

[32]  N. Bodor,et al.  A new method for the estimation of partition coefficient , 1989 .

[33]  S. Petrocelli,et al.  An evaluation of using partition coefficients and water solubility to estimate bioconcentration factors for organic chemicals in fish , 1980 .

[34]  J. Devillers,et al.  A predictive structure-toxicity model with Daphnia magna , 1987 .

[35]  Katsuichiro Komatsu,et al.  van der Waals Volume and the Related Parameters for Hydrophobicity in Structure-Activity Studies , 1976 .

[36]  N. Bodor,et al.  An extended version of a novel method for the estimation of partition coefficients. , 1992, Journal of pharmaceutical sciences.

[37]  Sujit Banerjee,et al.  Water solubility and octanol/water partition coefficients of organics. Limitations of the solubility-partition coefficient correlation , 1980 .

[38]  A. Leo.  CALCULATING LOG POCT FROM STRUCTURES , 1993 .

[39]  Octanol-water partition coefficients of chlorinated dioxins and dibenzofurans by reversed-phase HPLC using several C18 columns , 1984 .

[40]  Lars Kai Hansen,et al.  Neural Network Ensembles , 1990, IEEE Trans. Pattern Anal. Mach. Intell..

[41]  J Devillers,et al.  Nonlinear dependence of fish bioconcentration on n-octanol/water partition coefficient. , 1993, SAR and QSAR in environmental research.

[42]  Gerald J. Niemi,et al.  Optimal characterization of structure for prediction of properties , 1990 .

[43]  Raimund Mannhold,et al.  Calculation of Drug Lipophilicity: The Hydrophobic Fragmental Constant Approach , 1992 .

[44]  A. Kock,et al.  A simple procedure for determining octanol-water patition coefficients using reverse phase high performance liquid chromatography (RPHPLC) , 1987 .

[45]  Geoffrey E. Hinton,et al.  Learning representations by back-propagating errors , 1986, Nature.

[46]  H. Wiener.  Correlation of Heats of Isomerization, and Differences in Heats of Vaporization of Isomers, Among the Paraffin Hydrocarbons , 1947 .

[47]  Joop L. M. Hermens,et al.  Determination of octanol/water partition coefficients for hydrophobic organic chemicals with the “slow‐stirring” method , 1989 .

[48]  Yadu B. Tewari,et al.  Aqueous solubility and octanol/water partition coefficient of organic compounds at 25.0.degree.C , 1982 .

[49]  S. Unger.  Molecular Connectivity in Structure–activity Analysis , 1987 .

[50]  Russell C. Eberhart,et al.  Neural network PC tools: a practical guide , 1990 .

[51]  J. Devillers,et al.  AUTOLOGP Versus Neural Network Estimation of n -Octanol/Water Partition Coefficients , 1996 .

[52]  Gilles Klopman,et al.  A computer automated structure evaluation (CASE) approach to calculation of partition coefficient , 1991 .

[53]  A. Andren,et al.  Generator column determination of octanol/water partition coefficients for selected polychlorinated biphenyl congeners. , 1984, Environmental science & technology.

[54]  J. Devillers,et al.  Estimating the n-Octanol/Water Partition Coefficients of Polycyclic Aromatic Compounds with Autologp (2.11) , 1996 .

[55]  J Devillers,et al.  A General QSAR Model for Predicting the Toxicity of Organic Chemicals to Luminescent Bacteria (Microtox® test). , 1995, SAR and QSAR in environmental research.

[56]  D. Brooke,et al.  Octanol: Water partition coefficients (P): Measurement, estimation, and interpretation, particularly for chemicals with P > 105 , 1986 .

[57]  István Lukovits,et al.  Correlation between components of the Wiener index and partition coefficients of hydrocarbons , 1992 .

[58]  J. Devillers,et al.  A new approach in ecotoxicological QSAR studies , 1986 .

[59]  H. Wiener.  Structural determination of paraffin boiling points. , 1947, Journal of the American Chemical Society.

[60]  J. Devillers,et al.  QSAR for organic chemical sorption in soils and sediments , 1994 .