A new efficient approach for variable selection based on multiregression: Prediction of gas chromatographic retention times and response factors

Journal of Chemical Information and Computer Sciences

Volumn 39, Issue 3, 1999, Pages 610-621

  Lučić, Bono ^a   Trinajstić, Nenad ^a   Sild, Sulev ^b,c   Karelson, Mati ^c   Katritzky, Alan R ^b  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b University of Florida   (United States)

^c UNIVERSITY OF TARTU   (Estonia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040888006     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci980161a     Document Type: Article

References (48)

1. Georgakopoulos, C. G.; Kiburis, J. C.; Jurs, P. C. Prediction of Gas Chromatographic Relative Retention Times of Stimulants and Narcotics. Anal. Chem. 1991, 63, 2012-2024.
2. Georgakopoulos, C. G.; Tsika, O. G.; Kiburis J. C., Jurs, P. C. Prediction of Gas Chromatographic Relative Retention Times of Anabolic Steroids. Anal. Chem. 1991, 63, 2025-2028.
3. Needham, M. D.; Jurs, P. C. Quantitative Structure-Retention Relationship Studies of Polychlorinated Dibenzodioxins on Gas Chromatographic Stationary Phases of Varying Polarity. Anal. Chim. Acta 1992, 258, 183-198.
4. Needham, M. D.; Adams, K. C.; Jurs, P. C. Quantitative Structure-Retention Relationship Studies of Polychlorinated Dibenzofurans on Gas Chromatographic Stationary Phases of Varying Polarity. Anal. Chim. Acta 1992, 258, 199-218.
5. Woloszyn, T. F.; Jurs, P. C. Prediction of Gas Chromatographic Retention Behavior of Hydrocarbons from Naphthas. Anal. Chem. 1993, 65, 582-587.
6. Egolf, L. M.; Jurs, P. C. Quantitative Structure-Retention Relationship and Structure-Odor Intensity Relationships for a Diverse Group of Odor-Active Compounds. Anal. Chem. 1993, 65, 3119-3126.
7. Sutter, J. M.; Peterson, T. A.; Jurs, P. C. Prediction of Gas Chromatographic Relative Retention Times of Alkylbenzenes. Anal. Chim. Acta 1997, 342, 113-122.
8. Katritzky, A. R.; Ignatchenko, E. S.; Barcock, R. A.; Lobanov, V. S.; Karelson, M. Prediction of Gas Chromatographic Retention Times and Response Factors Using a General Quantitative Structure-Property Relationship Treatment. Anal. Chem. 1994, 66, 1799-1807.
9. Katritzky, A. R.; Lobanov, V. S.; Karelson, M. QSPR-The Correlation and Quantitative Prediction of Chemical and Physical Properties from Structure. Chem. Soc. Rev. 1995, 24, 279-287.
10. Karelson, M.; Lobanov, V. S.; Katritzky, A. R. Quantum-Chemical Descriptors in QSAR/QSPR Studies. Chem. Rev. 1996, 96, 1027-1043.
11. Katritzky, A. R.; Mu, L.; Karelson, M. A QSPR Study of the Solubility of Gases and Vapors in Water J. Chem. Inf. Comput. Sci. 1996, 36, 1162-1168.
12. Katritzky, A. R.; Rachwal, P.; Law, K. W.; Karelson, M.; Lobanov, V. S. Prediction of Polymer Glass Transition Temperatures Using a General Quantitative Structure-Property Relationship Treatment J. Chem. Inf. Comput. Sci. 1996, 36, 879-884.
13. Huibers, P. D. T.; Lobanov, V. S.; Katritzky, A. R.; Shah, D. O.; Karelson, M. Prediction of Critical Micelle Concentration Using a Quantitative Structure-Property Relationship Approach. 1. Nonionic Surfactants. Langmuir 1996, 12, 1462-1410.
14. Huibers, P. D. T.; Lobanov V. S.; Katritzky, A. R.; Shah, D. O.; Karelson, M. Prediction of Critical Micelle Concentration Using a Quantitative Structure-Property Relationship Approach. 2. Anionic Surfactants. J. Colloid Interface Sci. 1997, 187, 113-120.
15. Katritzky, A. R.; Maran, U.; Karelson, M.; Lobanov, V. S. Prediction of Melting Points for the Substituted Benzenes: A QSPR Approach. J. Chem. Inf. Comput. Sci. 1997, 37, 913-919.
16. Katritzky, A. R.; Lobanov, V. S.; Karelson, M. Normal Boiling Points for Organic Compounds: Correlation and Prediction by a Quantitative Structure-Property Relationship J. Chem. Inf. Comput. Sci. 1998, 38, 28-41.
17. Huibers, P. D. T.; Katritzky, A. R. Correlation of Aqueous Solubility of Hydrocarbons and Halogenated Hydrocarbons with Molecular Structure. J. Chem. Inf. Comput. Sci. 1998, 38, 283-292.
18. Katritzky, A. R.; Sild, S.; Lobanov, V. S.; Karelson, M. Quantitative Structure-Property (QSAR) Correlation of Glass Transition Temperatures of High Molecular Weight Polymers. J. Chem. Inf. Comput. Sci. 1998, 38, 300-304.
19. Karelson, M.; Maran, U.; Wang, Y.; Katritzky, A. R. QSPR and QSAR Models Derived with CODESSA Multipurpose Statistical Analysis Software J. Chem. Inf. Comput. Sci., submitted for publication.
20. Höskuldsson, A. Dimension of Linear Models. Chemom. Intell. Lab. Syst. 1996, 32, 37-55.
21. Hoffmann, R.; Minkin, V. I.; Carpenter, B. K. Ockham's Razor and Chemistry. Bull. Soc. Chim. Fr. 1996, 133, 117-130.
22. Kubinyi, H. Evolutionary Variable Selection in Regression and PLS Analyses. J. Chemom. 1996, 10, 119-133.
23. So, S.-S.; Karplus, M. Evolutionary Optimization in Quantitative Structure-Activity Relationship: An Application of Genetic Neural Network. J. Med. Chem. 1996, 39, 1521-1530.
24. Wessel, M. D.; Sutter, J. M.; Jurs, P. C. Prediction of Reduced Ion Mobility Constants of Organic Compounds from Molecular Structure. Anal. Chem. 1996, 68, 4237-4243.
25. Tetko, I. V.; Alessandro Villa, A. E. P.; Livingston, D. J. Neural Network Studies. 2. Variable Selection. J. Chem. Inf. Comput. Sci. 1996, 36, 794-803.
26. Lučić, B.; Nikolić, S., Trinajstić, N.; Juretić, D. The Structure-Property Models Can be Improved Using the Orthogonalized Descriptors. J. Chem. Inf. Comput. Sci. 1995, 35, 532-538.
27. Lučić, B.; Nikolić, S.; Trinajstić, N.; Juretić, D.; Jurić, A. A Novel QSPR Approach to Physicochemical Properties of the α-Amino Acids. Croat. Chem. Acta 1995, 68, 435-450.
28. Amić, D.; Davidović-Amić, D.; Bešlo, D.; Lučić, B.; Trinajstić, N. The Use of the Ordered Orthogonalized Multivariate Linear Regression in a Structure-Activity Study of Coumarin and Flavonoid Derivatives as Inhibitors of Aldose Reductase, J. Chem. Inf. Comput. Sci. 1997, 37, 581-586.
29. Lučić, B.; Trinajstić, N. New Developments in QSPR/QSAR Modeling Based on Topological Indices. SAR QSAR Environ. Res. 1997, 7, 45-62.
30. Press: W. H.; Teukolsky, S. A.; Wetterling, W. T.; Flannery, B. P. Numerical Recipes in FORTRAN: The Art of Scientific Computing, 2nd ed.; Cambridge University Press: Cambridge U.K., 1992.
31. Katritzky, A. R.; Mu, L.; Lobanov, V. S.; Karelson, M. Correlation of Boiling Points with Molecular Structure. 1. A Training Set of 398 Diverse Organic and a Test Set of 9 Simple Inorganics. J. Phys. Chem. 1996, 100, 10400-10407.
32. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. AM1: A New General Purpose Quantum Mechanical Molecular Model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
33. Stewart, J. J. P. MOPAC Program Package 6.0. QCPE 1990, 455.
34. Szabo, A.; Ostlund, N. Modern Quantum Chemistry; McGraw-Hill: New York, 1989; pp 15-21.
35. Andrea, T. A.; Kalayeh, H. Applications of Neural Networks in Quantitative Structure-Activity Relationships of Dihydrofolate Reductase Inhibitors. J. Med. Chem. 1991, 34, 2824-2836.
36. Randić, M. On Characterization of Molecular Branching. J. Am. Chem. Soc. 1975, 97, 6609-6615.
37. Kier, L. B.; Hall, L. H. Molecular Connectivity in Structure-Actvity Analysis; Wiley: New York, 1986.
38. oct) Using a Combination of Semiempirical Self-Consistent Reaction Field Calculations and Neural Networks. J. Chem. Inf. Comput. Sci. 1995, 35, 905-911.
39. Sternberg, J. C.; Gallway, W. S.; Jones, D. T. L. The Mechanism of Response of Flame Ionization Detectors. In Gas Chromatography; Brenner, N., Callen, J. E., Weiss, M. D., Eds.; Academic Press: New York, 1962; pp 231-267.
40. Lučić, B. Quantitative Structure-Activity-Property Relationships: The Use of Non-Orthogonalized and Ordered Orthogonalized Descriptors (in Croatian), Doctoral Thesis, Faculty of Science, University of Zagreb, Zagreb, Croatia, 1997.
41. Lučić, B.; Trinajstić, N. Multivariate Regression Outperforms Several Robust Architectures of Neural Networks in QSAR Modeling. J. Chem. Inf. Comput. Sci. 1999, 39, 121-132.
42. Aoyama, T.; Suzuki, Y.; Ichikawa, H. Neural Networks Applied to Quantitative Structure-Activity Relationship Analysis. J. Med. Chem. 1990, 33, 2583-2590.
43. Peterson, K. L. Quantitative Structure-Activity Relationships in Carboquinones and Benzodiazepines Using Counter-Propagation Neural Networks. J. Chem. Inf. Comput. Sci. 1995, 35, 896-904.
44. Lučić, B.; D. Amić, Trinajstić, N.; Katritzky, A. R. Multivariate Regression Outperforms Several Neural Network and Partial Least-Squares Models. Manuscript in preparation.
45. Medven, Z.; Güsten, H.; Sabljić, A. Comparative QSAR Study on Hydroxyl Radical Reactivity with Unsaturated Hydrocarbons-PLS versus MLR. J. Chemom. 1996, 10, 135-147.
46. 2 Carbon Atoms in Acyclic Alkenes Using Neural Networks. J. Chem. Inf. Comput. Sci. 1996, 36, 644-653.
47. Nefati, H.; Cense, J.-M.; Legendre, J.-J. Prediction of the Impact Sensitivity by Neural Networks. J. Chem. Inf. Comput. Sci. 1996, 36, 804-810.
48. Charlton, M. H.; Docherty, R.; Hutchings, M. G. Quantitative Structure-Sublimation Enthalpy Relationship Studied by Neural Networks, Theoretical Crystal Packing Calculations and Multilinear Regression Analysis. J. Chem. Soc., Perkin Trans. 2 1995, 2023-2030.