QSPR modeling of the water solubility of diverse functional aliphatic compounds by optimization of correlation weights of local graph invariants

Journal of Molecular Modeling

Volumn 11, Issue 2, 2005, Pages 89-96

  Roy, Kunal ^a   Toropov, Andrey A ^b  

^a JADAVPUR UNIVERSITY   (India)

^b S YU YUNUSOV INSTITUTE OF THE CHEMISTRY OF PLANT SUBSTANCES   (Uzbekistan)

Author keywords

Flexible descriptors; Nearest neighbouring codes; Optimization of correlation weights; QSAR; QSPR; Water solubility

Indexed keywords

2 BUTANOL; 2 METHYL 2 BUTANOL; 2,3 DIMETHYL 2 BUTANOL; 3 METHYL 2 BUTANOL; 3,3 DIMETHYL 1 BUTANOL; ACETIC ACID; ALIPHATIC COMPOUND; BUTANOL; CHLOROFORM; CYCLOHEXANE; CYCLOPENTANE; DECANOL; HEXANOL; ISOPENTYL ALCOHOL; METHYL IODIDE; MYRISTYL ALCOHOL; NONANOL; OCTANOL; PENTANOL; PINACOLYL ALCOHOL; UNCLASSIFIED DRUG; WATER;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CONTROLLED STUDY; CORRELATION ANALYSIS; PREDICTION; PRIORITY JOURNAL; PROCESS OPTIMIZATION; QUANTITATIVE STRUCTURE PROPERTY RELATION; SOLUBILITY; STATISTICAL ANALYSIS;

ALCOHOLS; ESTERS; ETHERS; MODELS, CHEMICAL; ORGANIC CHEMICALS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REGRESSION ANALYSIS; SOLUBILITY; WATER;

EID: 33646249822     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-004-0224-7     Document Type: Article

References (58)

1. Harary F (1971) Graph theory. Addison-Wesley, Reading, MA
2. Balaban AT (ed) (1976) Chemical application of graph theory. Academic Press, London
3. Trinajstic N (1992) Chemical graph theory, 2nd edn. CRC Press, Boca Raton
4. Devillers J, Balaban AT (eds) (1999) Topological indices and related descriptors in QSAR and QSPR. Gordon and Breach Science Publishers, The Netherlands
5. Ivanciuc O (1998) Structural similarity measures for database searching. In: Schleyer PvR, Allinger NL, Clark T, Gasteiger J, Kollman PA, Schaefer HF, Schniener PR (eds) Encyclopedia of computational chemistry. Wiley, Chichester
6. Boncher D, Rouvray DH (eds) (1991) Chemical graph theory. Introduction and Fundamentals. Academic Press, New York
7. Balaban AT (ed) (1997) From chemical topology to three-dimensional geometry. NewYork
8. Kier LB, Hall LH (1976) Molecular connectivity in chemistry and drug research. Academic Press, New York
9. Kier LB, Hall LH (1986) Molecular connectivity in structure-activity analysis. Research Studies Press, Letchworth
10. Todeschini R, Consonni V (2000) Handbook of molecular descriptors. Wiley-VCH, Weinheim, Germany
11. Kier LB (1989) Quant Struct-Act Relat 8:218-223
12. Randic M (1991) J Comput Chem 12:970-980
13. Randic M (1991) Chemom Intell Lab Syst 10:213-227
14. Randic M (1991) J Chem Inf Comput Sci 31:311-320
15. Randic M (1992) J Chem Inf Comput Sci 32:686-692
16. Estrada E (1995) J Chem Inf Comput Sci 35:1022-1025
17. Amic D, Beslo D, Lucic D, Nikolic S, Trinajstic N (1998) J Chem Inf Comput Sci 38:819-822
18. Randic M, Basak SC (1999) J Chem Inf Comput Sci 39:261-266
19. Sinha DK, Basak SC, Mohanty RK, Basumallick IN (1999) Some aspects in mathematical chemistry. Visva-Bharati University Press, Santiniketan
20. Toropov AA, Toropova AP (1998) Russ J Coord Chem 24:81-85
21. Toropov AA, Toropova AP, Voropaeva NL, Ruban IN, Rashidova SS (1998) J Coord Chem 24:525-529
22. Toropov AA, Voropaeva NL, Ruban IN, Rashidova SS (1999) Polym Sci Ser A 41:975-985
23. Krenkel G, Castro EA, Toropov AA (2001) J Mol Struct (THEOCHEM) 542:107-113
24. Mercader A, Castro EA, Toropov AA (2001) J Mol Model 7:1-5
25. Mercader A, Castro EA, Toropov AA (2000) Chem Phys Lett 330:612-623
26. Krenkel G, Castro EA, Toropov AA (2001) J Mol Sci 2:57-65, http://www.mdpi.org/ijms
27. Marino DJG, Perruzo PJ, Castro EA, Toropov AA (2002) Internet Electron J Mol Des 1:115-133, http://www.biochempress.com
28. Duchowicz P, Castro EA, Toropov AA (2002) Computers and Chemistry 26:327-332
29. Toropov AA, Duchowicz P, Castro EA (2003) Int J Mol Sci 4:272-283, http://www.mdpi.org/ijms
30. Perruzo PJ, Marino DJG, Castro EA, Toropov AA (2003) Internet Electron J Mol Des 2:334-347, http://www.biochempress.com
31. Toropov AA, Schultz TW (2003) J Chem Inf Comput Sci 43:560-567
32. Toropov AA, Roy K (2004) J Chem Inf Comput Sci 44:179-186
33. Kubinyi H (1995) Quantitative structure-activity relationships. In: Wolff ME (ed) Burger's medicinal chemistry and drug discovery, 5th edn, vol 1. John Wiley New York, pp 497-571
34. Ghose AK, Crippen GM (1987) J Chem Inf Comput Sci 27:21-35
35. Ghose AK, Viswanadhan VN, Wendoloski JJ (1998) J Phys Chem 102:3762-3772
36. Bodor N, Gabanyi Z, Wong C-K (1989) J Am Chem Soc 111:3783-3786
37. Klopman G, Wang S (1991) J Comput Chem 12:1025-1032
38. Moriguchi I, Hirono S, Liu Q, Nakagome I, Matsushita Y (1992) Chem Pharm Bull (Tokyo) 40:127-130
39. Saxena AK (1995) Quant Struct-Act Relat 14:142-150
40. Benet LZ, Kroetz DL, Sheiner LB (1996) In: Hardman JG, Limbard LE, Molinoff PB, Ruddon RW, Goodman Gilman A (eds) Goodman and Gilman's The pharmacological basis of therapeutics. Mc-Graw Hill, New York, pp 3-27
41. Ferreira MM (2001) Chemosphere 44:125-146
42. Khadikar PV, Mandloi F, Bajaj AV, Joshi S (2003) Bioorg Med Chem Lett 13:419-422
43. Katritzky AR, Wang Y, Sild S, Tamm T (1998) J Chem Inf Comput Sci 38:720-725
44. Yin C, Liu X, Guo W, Lin T, Wang X, Wang L (2002) Water Res 36:2975-2982
45. Chen XQ, Cho SJ, Li Y, Venkatesh S (2002) J Pharm Sci 91:1838-1852
46. Roy K, Saha A (2003) Internet Electron J Mol Des 2:475-491, http://www.biochempress.com
47. Yang F, Wang ZD Huang YP (2004) J Comput Chem 25:881-887
48. Wanchana S, Yamashita F, Hashida M (2002) Pharmazie 57:127-129
49. Gao H, Shanmugasundaram V, Lee P (2002) Pharm Res 19:497-503
50. Puri S, Chickos JS, Welsh WJ (2003) J Chem Inf Comput Sci 43:55-62
51. Liu R, So SS (2001) J Chem Inf Comput Sci 41:1633-1639
52. Butina D, Gola JM (2003) 43:837-841
53. Hansch C, Quinlan JE, Lawrence GL (1968) J Org Chem 33:347-350
54. The program for optimization of correlation weights was developed in PASCAL by Toropov AA
55. The GW-BASIC programs RRR98, KRPRES1 and KRPRES2 were developed by Kunal Roy (1998) and standardized using known data sets.
56. Snedecor GW, Cochran WG (1967) Statistical Methods. Oxford& IBH Publishing Co. Pvt. Ltd., New Delhi, pp 381-418
57. Kier LB, Hall LH (1992) Atom description in QSAR models: Development and use of an atom level index. In: Testa B (ed) Advances in drug research, vol 22. Academic Press, New York, pp 1-38
58. Wold S, Eriksson L (1995) Validation tools. In: Van de Waterbeemd H (ed) Chemometric methods in molecular design. VCH, Weinheim, pp 309-318