Simulating lipophilicity of organic molecules with a back-propagation neural network

Journal of Pharmaceutical Sciences

Volumn 87, Issue 9, 1998, Pages 1086-1090

  Devillers, James ^a   Domine, Daniel ^a   Guillon, Cécile ^a   Karcher, Walter ^b  

^a CTIS   (France)

^b JOINT RESEARCH CENTRE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HALOGEN; NITROGEN; PHOSPHORUS; SULFUR;

ARTICLE; CHEMICAL REACTION; COMPUTER SIMULATION; HYDROGEN BOND; HYDROPHOBICITY; LIPOPHILICITY; MOLECULAR DYNAMICS; PHYSICAL CHEMISTRY; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 0031691050     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js980101j     Document Type: Article

References (21)

1. 50) of benzene derivatives using theoretical molecular descriptors: A hierarchical QSAR approach. SAR QSAR Environ. Res. 1997, 7, 117-131.
2. Fujita, T.; Iwasa, J.; Hansch, C. A new substituent constant, π, derived from partition coefficients. J. Am. Chem. Soc. 1964, 86, 5175-5180.
3. oct from structures. Chem. Rev. 1993, 93, 1281-1306.
4. Rekker, R. F.; Mannhold, R. Calculation of Drug Lipophilicity. The Hydrophobic Fragmental Constant Approach; VCH: Weinheim, 1992; p 112.
5. Hansch, C.; Leo, A. Exploring QSAR. Fundamentals and Applications in Chemistry and Biology; ACS Professional Reference Book, American Chemical Society: Washington, DC, 1995; p 557.
6. Klopman, G.; Li, J.-Y.; Wang, S.; Dimayuga, M. Computer automated log P calculations based on an extended group contribution approach. J. Chem. Inf. Comput. Sci. 1994, 34, 752-781.
7. Meylan, W. M.; Howard, P. H. Atom/fragment contribution method for estimating octanol-water partition coefficients. J. Pharm. Sci. 1995, 84, 83-92.
8. Klopman, G.; Iroff, L. D. Calculation of partition coefficients by the charge density method. J. Comput. Chem. 1981, 2, 157-160.
9. Devillers, J.; Lipnick, R. L. In Practical Applications of Quantitative Structure-Activity Relationships (QSAR) in Environmental Chemistry and Toxicology; Karcher, W., Devillers, J., Eds.; Kluwer Academic Publishers: Dordrecht, 1990; pp 129-143.
10. Devillers, J.; Zakarya, D.; Chastrette, M.; Doré, J. C. The stochastic regression analysis as a tool in ecotoxicological QSAR studies. Biomed. Environ. Sci. 1989, 2, 385-393.
11. Devillers, J. In Neural Networks in QSAR and Drug Design; Devillers, J., Ed.; Academic Press: London, 1996, pp 1-46.
12. Domine, D.; Devillers, J.; Karcher, W. In Neural Networks in QSAR and Drug Design, Devillers, J., Ed.; Academic Press: London, 1996; pp 47-63.
13. Moreau, G.; Broto, P. The autocorrelation of a topological structure: A new molecular descriptor. Nouv. J. Chim. 1980, 4, 359-360.
14. Moreau, G.; Broto, P. Autocorrelation of molecular structures, application to SAR studies. Nouv. J. Chim. 1980, 4, 757-764.
15. Broto, P.; Devillers, J. In Practical Applications of Quantitative Structure-Activity Relationships (QSAR) in Environmental Chemistry and Toxicology; Karcher, W., Devillers, J., Eds.; Kluwer Academic Publishers: Dordrecht, 1990; pp 105-127.
16. Devillers, J.; Domine, D.; Chastrette, M. A new method of computing the octanol/water partition coefficient. In Proceedings of QSAR92, (July 19-23, 1992, Duluth, MN, p 12.
17. Devillers, J.; Domine, D.; Karcher, W. Estimating n-octanol/water partition coefficients from the autocorrelation method. SAR QSAR Environ. Res. 1995, 3, 301-306.
18. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; J. Wiley & Sons: New York, 1979; p 339.
19. Hansen, L. K.; Salamon, P. Neural network ensembles. IEEE Trans. Pattern Anal. Machine Intell. 1990, 12, 993-1001.
20. Schaper, K. J.; Samitier, M. L. R. Calculation of octanol/water partition coefficients (log P) using artificial neural networks and connection matrices. Quant. Struct. Act. Relat. 1997, 16, 224-230.
21. The model has been implemented in AUTOLOGP (Version 4.0), a user-friendly software running on IBM and compatible PC under Windows 3.1 and Windows 95.