Comparison of predictive ability of water solubility QSPR models generated by MLR, PLS and ANN methods

Mini-Reviews in Medicinal Chemistry

Volumn 4, Issue 2, 2004, Pages 167-177

  Erös, Daniel ^a   Kéri, György ^a,b   Kövesdi, István ^b   Szántai Kis, Csaba ^a   Mészáros, György ^a   Örfi, Laszlo ^a,b  

^a SEMMELWEIS UNIVERSITY   (Hungary)

^b Vichem Chemie Ltd   (Hungary)

Author keywords

ADME; ANN; External validation; MLR; PLS; QSPR; Virtual screening; Water solubility

Indexed keywords

2,4 DINITROTOLUENE; ANTHRACENE DERIVATIVE; BENZ[A]ANTHRACENE DERIVATIVE; BENZO[E]PYRENE; BENZONITRILE; BIPHENYL DERIVATIVE; BROMOBENZENE; BUTYRALDEHYDE; CARBAZOLE DERIVATIVE; GALLIC ACID; HEPTANE; HEXACHLOROBUTADIENE; INDOLE; ISOPENTYL ALCOHOL; MALATHION; NAPHTHALENE DERIVATIVE; NAPHTHALENESULFONIC ACID DERIVATIVE; NITROBENZENE DERIVATIVE; NITROBENZOIC ACID DERIVATIVE; PARA XYLENE; PENTOBARBITAL; PHENOBARBITAL; PHENOLPHTHALEIN; PROCAINE; PYRENE; TETRACHLOROETHANE; TETRAHYDROFURAN; TRICHLOROFLUOROMETHANE; UNINDEXED DRUG; WATER;

ANALYTIC METHOD; ANALYTICAL ERROR; AQUEOUS SOLUTION; ARTIFICIAL NEURAL NETWORK; CALCULATION; COMBINATORIAL LIBRARY; CONTROLLED STUDY; CORRELATION COEFFICIENT; DATA BASE; DRUG RESEARCH; DRUG SCREENING; DRUG SOLUBILITY; LINEAR REGRESSION ANALYSIS; MATHEMATICAL COMPUTING; PREDICTION; PROCESS OPTIMIZATION; REGRESSION ANALYSIS; RELIABILITY; REVIEW; SCIENTIFIC LITERATURE; SCORING SYSTEM; STATISTICAL ANALYSIS; VALIDATION PROCESS;

CHEMISTRY, PHYSICAL; LEAST-SQUARES ANALYSIS; LINEAR MODELS; MODELS, CHEMICAL; MODELS, MOLECULAR; MODELS, STATISTICAL; NEURAL NETWORKS (COMPUTER); QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REPRODUCIBILITY OF RESULTS; SOLUBILITY; WATER;

EID: 17044455173     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/1389557043487466     Document Type: Review

References (66)

1. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Deliv. Rew. 1997, 23, 3.
2. Yalkowsky, S. H.; Banerjee, S. Aqueous solubility: methods of estimation for organic compounds. Dekker: New York, 1992.
3. Yalkowsky, S. H.; Valvani, S. C. J. Pharm. Sci. 1980, 69. 912.
4. Ran, Y.; Jain, N.; Yalkowsky, S. H. J. Chem. Inf. Comput. Sci. 2001, 41, 1208.
5. Ran, Y.; He, Y; Yang, G.; Johnson, J. L. H.; Yalkowsky, S. H. Chemosphere 2002, 48, 487.
6. Isnard, P.; Lambert, S. Chemosphere 1989, 18, 1837.
7. Warne, M.; Connel, D. W.; Hawker, D. W.; Schhhrmann, G. Chemosphere 1990, 21, 877.
8. Miller, M.; Ghogbane, S.; Waski, S. P.; Tewari, T. B.; Nartire, D. E. J. Chem. Eng. Data 1984, 29, 184.
9. Yaws, C.; Pan, X.; Lin, X. Chem. Eng. 1993, Feb, 108.
10. Ruelle. P.; Kesselring, U. Chemosphere 1997, 2, 275.
11. Wakita, K.; Yoshimota; Miyamoto; Watanable Chem. Pharm. Bull. 1986, 34, 4663.
12. Suzuki, T. J. Comput.-Aid. Mol. Design 1991, 5, 149.
13. Klopman, G.; Wang, S.; Balthasar, D. M. J. Chem Inf. Conput. Sci. 1992, 32, 474.
14. Klopman, G.; Zhu, H. J. Chem. Inf. Comput. Sci. 2001, 41, 439.
15. Kühne, R.; Ebert, R. U.; Kleint, F.; Schmidt, G.; Schüürmann, G. Chemosphere 1995, 30, 2061.
16. Medir, M.; Giralt, F. AIChE J. 1982, 28, 341.
17. Nirmalakhandan, N. N.; Speece, R. E. Environ. Sci. Technol. 1988, 22, 328.
18. Nirmalakhandan, N. N.; Speece, R. E. Environ. Sci. Technol. 1989, 23, 708.
19. Patil, G. S. Chemosphere 1991, 22, 723.
20. Makino, M. Environ. Intl. 1998, 24, 653.
21. Huibers, P. D. T.; Katritzky, A. R. J. Chem. Inf. Comput. Sci. 1998, 38, 283.
22. Katritzky, A. R. J. Chem. Inf. Comput. Sci. 1998, 38, 720.
23. Huuskonen, J.; Marja Salo, M.; Taskinen, J. J. Chem. Inf. Comput. Sci. 1998, 38, 450.
24. Sutter, J. M.; Jurs, P. C. J. Chem. Inf. Comput. Sci. 1996, 36, 100.
25. Mitchell, B. E.; Jurs, P. C.; J. Chem. Inf. Comput. Sci. 1998, 38, 489.
26. Engkvist, O.; Wrede, P. J. Chem. Inf. Comput. Sci. 2002, 42, 1247.
27. McElroy, N. R.; Jurs, P. C. J. Chem. Inf. Comput. Sci. 2001, 41, 1237.
28. McFarland, J. W. J. Chem. Inf. Comput. Sci. 2001, 41, 1355.
29. Yaffe, D.; Cohen, Y.; Espinosa, G.; Arenas, A.; Giralt, F. J. Chem. Inf. Comput. Sci. 2001, 41, 1177.
30. Liu, R.; So. S.-S. J. Chem. Inf. Comput. Sci. 2001, 41, 1633.
31. Yin, C.; Liu, X.; Guo, W.; Lin, T.; Wang, X.; Wang L. Water Research 2002, 36, 2975.
32. Jorgensen, W. L.; Duffy, E. M. Bioorg. Med. Chem. Lett. 2000. 10, 1155.
33. Collette, T. W. Vibrational Spectroscopy 1997, 15, 113.
34. Huuskonen, J. J. Chem. Inf. Comput. Sci. 2000, 40, 773.
35. Chen, X. Q.; Cho, S. J.; Li, Y.; Venkatesh, S. J. Pharm. Sc. 2002, 91, 1838.
36. Bergstrom, C. A. S.; Norinder, U.; Luthman, K.; Artursson, P. Pharm. Res. 2002, 19, 182.
37. Delgado, E. J. Fluid Phase Equilibria, 2002, 199, 101.
38. Jorgensen, W. L.; Duffy, E. M. Adv. Drug Del. Rev. 2002, 54, 355.
39. Huuskonen, J.; Rantanen, J.; Livingstone, D. Eur. J. Med. Chem. 2000, 35, 1081.
40. Wanchana, S.; Yamashita, F.; Hashida, M. Pharmazine 2002, 2, 127.
41. Abraham, M. H.; Joelle, J. J. Pharm. Sci. 1999, 88, 868.
42. Bruneau, P. J. Chem. Inf. Comput. Sci. 2001, 41, 1605.
43. Isis™/Base, Ver. 2.3, MDL Information Systems, Inc., 1990-2000.
44. Ruskino, A.; Skell, J. M.; Balducci, R.; McGarity, C. M.; Pearlman, R. S. Univ. of Texas, Austin, TX and Tripos, St. Louis, MO USA 1988, CONCORD 6.0, 1992, TRIPOS Associates Inc., St. Louis, Missouri.
45. 3DNET, Vichem Ltd., Budapest, Hungary 1999.
46. Connolly, M. L. J. Am. Chem. Soc. 1985, 107, 1118.
47. De Bruijn, J; Hermkens, J. J. Quant. Struct-Act. Relat. 1990, 9, 11.
48. Bodor, N.; Buchwald, P. J. Phys. Chem. 1997, 101, 3404.
49. Iwase, K; Komatau, K.; Hirono, S.; Nakagawa, S.; Moriguchi, I. Chem. Pharm. Bull. 1985, 33, 2114.
50. Meyer, A. Y. J. Chem. Soc. Rev. 1986, 15, 449.
51. Todeschini, R.; Grammatica, P. Quant. Struct.-Act. Relat. 1997, 16, 120.
52. Breindl, A.; Beck, B.; Clark, T.; Glen, R. C. J. Mol. Model. 1997, 3, 142.
53. Miller, K. J. J. Am. Chem. Soc. 1990, 112, 8533.
54. Mortier, W. J.; Genechten, K.; Gasteiger, J. J. Am. Chem. Soc. 1985, 107, 829.
55. Fedors, R. F.; Van Krevelen, D. V.; Hoftyzer, P. J. C R C Handbook of Solubility, Parameters and Other Cohesion Parameters, CRC Press: New York, 1986.
56. Andrews, P. R.; Craik, D. J., Martin, J. L. J. Med. Chem. 1984, 27, 1648.
57. Wiener, H. J. Am. Chem. Soc. 1947, 69, 2636.
58. Randic, M. J. Am. Chem. Soc. 1975, 97, 6609.
59. Katritzky, A. R.; Lobanov, V. S.; Karelson, M. J. Chem. Inf. Comput. Sci. 1998, 38, 28.
60. Bodor, N.; Huang, M. J.; Harget, A. J. Mol. Struct. (Theochem.) 1994, 309, 259.
61. Gaillard, P.; Carrupt, P.; Testa, B.; Boudon, A. J. Comput.-Aided Mol. Des. 1994, 8, 83.
62. Cronce, T. D.; Famini, G. R.; De Soto, J. A.; Wilson, L. Y. J. Chem. Soc. Perkin Trans. 1998, 2, 1293.
63. Eros, D.; Kövesdi, I.; Orfi, L.; Takács-Novák, K.; Acsády, Gy.; Kéri, Gy. Curr. Med. Chem. 2002, 9, 1819.
64. 3DNET4W, Vichem Ltd., Budapest, Hungary 2002.
65. Snee, R. D. Technometrics 1997, 415.
66. http://146.107.217.178/lab/alogps/start.html.