Prediction of Aqueous Solubility of Heteroatom-Containing Organic Compounds from Molecular Structure

Journal of Chemical Information and Computer Sciences

Volumn 41, Issue 3-6, 2001, Pages 1237-1247

  McElroy, Nathan R ^a   Jurs, Peter C ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

QUANTITATIVE STRUCTURE-PROPERTY RELATIONSHIPS (QSPR);

ALCOHOLS; COMPUTATIONAL METHODS; NEURAL NETWORKS; SOLUBILITY;

MOLECULAR STRUCTURE;

EID: 0035470268     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci010035y     Document Type: Article

References (53)

1. Sutter, J. M.; Jurs, P. C. Prediction of Aqueous Solubility for a Diverse Set of Heteroatom-Containing Organic Compounds Using a Quantitative Structure-Property Relationship. J. Chem. Inf. Comput. Sci. 1996, 36, 100-107.
2. Mitchell, B. E.; Jurs, P. C. Prediction of Aqueous Solubility of Organic Compounds from Molecular Structure. J. Chem. Inf. Comput. Sci. 1998, 38, 489-496.
3. Bakken, G. A.; Jurs, P. C. Prediction of Hydroxyl Radical Rate Constants from Molecular Structure. J. Chem. Inf. Comput. Sci. 1999, 39, 1064-1075.
4. Bakken, G. A.; Jurs, P. C. Prediction of Methyl Radical Addition Rate Constants from Molecular Structure. J. Chem. Inf. Comput. Sci. 1999, 39, 508-514.
5. Goll, E. S.; Jurs, P. C. Prediction of the Normal Boiling Points of Organic Compounds form Molecular Structures with a Computational Neural Network Model. J. Chem. Inf. Comput. Sci. 1999, 39, 974-983.
6. Goll, E. S.; Jurs, P. C. Prediction of Vapor Pressures of Hydrocarbons and Halohydrocarbons from Molecular Structure with a Computational Neural Network Model. J. Chem. Inf. Comput. Sci. 1999, 39, 1081-1089.
7. Johnson, S. R.; Jurs, P. C. Prediction of the Clearing Temperatures of a Series of Liquid Crystals from Molecular Structure. Chem. Mater. 1999, 11, 1007-1023.
8. McClelland, H. E.; Jurs, P. C. Quantitative Structure-Property Relationships for the Prediction of Vapor Pressure of Organic Compounds from Molecular Structure. J. Chem. Inf. Comput. Sci. 2000, 40, 967-975.
9. Kauffman, G. W.; Jurs, P. C. Prediction of Inhibition of the Sodium Ion-Proton Anitporter by Benzoylguanidine Derivatives from Molecular Structure. J. Chem. Inf. Comput. Sci. 2000, 40, 753-761.
10. Patankar, S. J.; Jurs, P. C. Prediction of IC50 Values for ACAT Inhibitors from Molecular Structure. J. Chem. Inf. Comput. Sci. 2000, 40, 706-723.
11. Klopman, G.; Wang, S.; Balthasar, D. M. Estimation of Aqueous Solubility of Organic Molecules by the Group Contribution Approach. Application to the Study of Biodegradation. J. Chem. Inf. Comput. Sci. 1992, 32, 474-482.
12. Kühne, R.; Ebert, R.-U.; Kleint, F.; Schmidt, G.; Schüürmann, G. Group Contribution Methods to Estimate Water Solubility of Organic Chemicals. Chemosphere 1995, 30, 2061-2077.
13. Ruelle, P.; Kesserling, U. W. Prediction of the aqueous solubility of proton-acceptor oxygen-containing compounds by the mobile order solubility model. J. Chem. Soc., Faraday Trans. 1997, 93, 2049-2052.
14. Ruelle, P.; Kesserling, U. W. Solubility Prediction of n-fatty Alcohols and Sterols in Complexing and Noncomplexing Solvents According to the Mobile Order Theory. Can. J. Chem. 1998, 76, 553-565.
15. Makino, M. Predictions of Aqueous Solubility Coefficients of Polychlorinated Biphenyls by Use of Computer-Calculated Molecular Properties. Environ. Int. 1998, 24, 653-663.
16. Huibers, P. D. T.; Katritzky, A. R. Correlation of the Aqueous Solubility of Hydrocarbons and Halogenated Hydrocarbons with Molecular Structure. J. Chem. Inf. Comput. Sci. 1998, 35, 283-292.
17. Abraham, M. H.; Le, J. The Correlation and Prediction of the Solubility of Compounds in Water Using an Amended Solvation Energy Relationship. J. Pharm. Sci. 1999, 88, 868-880.
18. Bodor, N.; Huang, M.-J. A New Method for the Estimation of the Aqueous Solubility of Organic Compounds. J. Pharm. Sci. 1992, 81, 954-960.
19. Huuskonen, J.; Salo, M.; Taskinen, J. Neural Network Modeling for Estimation of the Aqueous Solubility of Structurally Related Drugs. J. Pharm. Sci. 1997, 86, 450-454.
20. Huuskonen, J.; Salo, M.; Taskinen, J. Aqueous Solubility Prediction of Drugs Based on Molecular Topology and Neural Network Modeling. J. Chem. Inf. Comput. Sci. 1998, 38, 450-456.
21. Huuskonen, J. Estimation of Aqueous Solubility for a Diverse Set of Organic Compounds Based on Molecular Topology. J. Chem. Inf. Comput. Sci. 2000, 40, 773-777.
22. Handbook of Physical Properties of Organic Chemicals; Howard, P. H., Meylan, W. M., Eds.; CRC Press: 1997.
23. Jurs, P. C.; Chow, J. T.; Yuan, M. In Computer-Assisted Drug Design; Olson, E. C., Christoffersen, R. E., Eds.; The American Chemical Society: Washington, DC, 1979; pp 103-129.
24. Stuper, A. J.; Brugger, W. E.; Jurs, P. C. Computer-Assisted Studies of Chemical Structure and Biological Function; Wiley: New York, 1979.
25. Sutter, J. M.; Dixon, S. L.; Jurs, P. C. Automated Descriptor Selection for Quantitative Structure-Activity Relationships Using Generalized Simulated Annealing. J. Chem. Inf. Comput. Sci. 1995, 35, 77-84.
26. Luke, B. T. Evolutionary Programming Applied to the Development of Quantitative Structure-Activity Relationships and Quantitative Structure-Property Relationships. J. Chem. Inf. Comput. Sci. 1994, 34, 1279-1287.
27. Xu, L.; Ball, J. W.; Dixon, S. L.; Jurs, P. C. Quantitative Structure-Activity Relationships For Toxicity Of Phenols Using Regression Analysis And Computational Neural Networks. Environ. Toxicol. Chem. 1994, 13, 841-851.
28. Stewart, J. P. P. MOPAC 6.0, Quantum Chemistry Program Exchange; Program 455; Indiana University: Bloomington, IN, 1990.
29. Stewart, J. J. P. MOPAC: A semiempirical molecular orbital program. J. Cumput.-Aided Mol. Des. 1990, 4, 1-105.
30. Dewar, M. J. S.; Zoebisch, E. G.; Healey, E. F.; Stewart, J. P. P. AMI: A New General Purpose Quantum Mechanical Molecular Model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
31. Alemán, C.; Luque, F. J.; Orozco, M. Suitability of the PM3-Derived Molecular Electrostatic Potentials. J. Comput. Chem. 1993, 14, 799-808.
32. Kier, L. B. A Shape Index from Molecular Graphs. Quant. Struct.-Act. Relat. 1985, 4, 109-116.
33. Kier, L. B. Distinguishing Atom Differences in a Molecular Graph Shape Index. Quant. Struct.-Act. Relat. 1986, 5, 7-12.
34. Kier, L. B. Shape Indexes of Orders One to Three from Molecular Graphs. Quant. Struct.-Act. Relat. 1986, 5, 1-7.
35. Randic, M.; Brissey, G. M.; Spencer, R. B.; Wilkins, R. B. Search for All Self-Avoiding Paths on Molecular Graphs. Comput. Chem. 1979, 3, 5-13.
36. Randic, M. On Molecular Identification Numbers. J. Chem. Inf. Comput. Sci. 1984, 24, 164-175.
37. Kier, L. B.; Hall, L. H. Molecular Connectivity in Chemistry and Drug Research; Academic Press: New York, 1976.
38. Kier, L. B.; Hall, L. H. Molecular Connectivity in Structure-Activity Analysis; John Wiley & Sons: New York, 1986; pp 18-20.
39. Cao, C. Distance-Edge Topological Index: Research on Structure-Property Relationship of Alkanes. Huaxue Tongao 1996, 54, 533-538.
40. Pearlman, R. S. In Physical Chemical Properties of Drugs; Yalkowsky, S. H., Sinkula, A. A., Valvani, S. C., Eds.; Marcel Dekker: New York, 1980; Chapter 10.
41. Goldstein, H. Classical Mechanics; Addison-Wesley: Reading, MA, 1950; pp 144-156.
42. Stouch, T. R.; Jurs, P. C. A Simple Method for the Representation, Quantification, and Comparison of the Volumes and Shapes of Chemical Compounds. J. Chem. Inf. Comput. Sci. 1986, 26, 4-12.
43. Rohrbaugh, R. H.; Jurs, P. C. Molecular Shape and the Prediction of High-Performance Liquid Chromatographic Retention Indexes of Polycyclic Aromatic Hydrocarbons. Anal. Chem. 1987, 59, 1048-1054.
44. Dixon, S. L.; Jurs, P. C. Atomic Charge Calculations for Quantitative Structure-Property Relationships. J. Comput. Chem. 1992, 13, 492-504.
45. Miller, K. J.; Savchik, J. A. A New Empirical Method To Calculate Average Molecular Polarizabilities. J. Am. Chem. Soc. 1979, 101, 7206-7213.
46. Abraham, R. J.; Smith, P. E. Charge Calculations in Molecular Mechanics IV: A General Method for Conjugated Systems. J. Comput. Chem. 1988, 9, 288-297.
47. Stanton, D. T.; Jurs, P. C. Development and Use of Charged Partial Surface Area Structural Descriptors in Computer-Assisted Quantitative Structure-Property Relationship Studies. Anal. Chem. 1990, 62, 2323-2329.
48. Topliss, J. G.; Edwards, R. P. Chance Factors in Studies of Quantitative-Structure Property Relationships. J. Med. Chem. 1979, 22, 1238-1244.
49. Belsley, D. A.; Kuh, E.; Welsch, R. E. Regression Diagnostics; John Wiley & Sons: New York, 1980.
50. Draper, N. R.; Smith, H. Applied Regression Analysis; John Wiley & Sons: New York, 1981.
51. Livingstone, D. J.; Manallack, D. T. Statistics Using Neural Networks: Chance Effects. J. Med. Chem. 1993, 36, 1295-1297.
52. Wessel, M. D.; Jurs. P. C. Prediction of Reduced Ion Mobility Constants from Structural Information Using Multiple Linear Regression Analysis and Computational Neural Networks. Anal. Chem. 1994, 66, 2480-2487.
53. Katritzky, A. R.; Mu, L.; Lobanov, V. S.; Karelson, M. Correlation of Boiling Points with Molecular Structure. 1. A Training Set of 298 Diverse Organics and a Test Set of 9 Simple Organics. J. Phys. Chem. 1996, 100, 10400-10407.