Variable connectivity index as a tool for modeling structure-property relationships

Molecules

Volumn 9, Issue 12, 2004, Pages 1177-1193

  Randić, Milan ^a,b   Pompe, Matevž ^c   Mills, Denise ^d   Basak, Subhash C ^d  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^b University of Ljubljana ^*  (United States)

^c UNIVERSITY OF LJUBLJANA   (Slovenia)

^d Natural Resources Research Institute   (United States)

Author keywords

Aliphatic alcohols; Flexible molecular descriptors; Normal boiling points; Variable connectivity index

Indexed keywords

ALKANOL; CARBON; OXYGEN;

ANALYTICAL ERROR; ARTICLE; DATA ANALYSIS; MOLECULAR WEIGHT; STATISTICAL ANALYSIS; STATISTICAL MODEL; STRUCTURE ACTIVITY RELATION; TEMPERATURE DEPENDENCE;

EID: 12344308328     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/91201177     Document Type: Article

References (51)

1. Todeschini, R.; Consonni, V. Handbook of Molecular Descriptors (Methods and Principles in Medicinal Chemistry, vol. 11; Mannhold, R.; Kubinyi, H.; Timmerman, H., Eds.; Wiley-VCH: New York, 2000
2. Devillers, J; Balaban, A. T., Eds. Topological Indices and Related Descriptors in QSAR and QSPR; Gordon and Breach: Amsterdam, 1999
3. Lučić, B.; Miličević, A.; Nikolić, S.; Trinajstić, N. On variable Wiener index. Ind. J. Chem. A 2003, 42, 1279-1282
4. Estrada, E. Three-dimensional generalized graph matrix, Harary descriptors and a generalized interatomic Lennard-Jones potential. J. Phys. Chem. A 2004, 108, 5468-5473
5. Estrada, E. Generalized Graph Matrix, Graph Geometry, Quantum Chemistry and the Optimal Description of Physicochemical Properties. J. Phys. Chem. A 2003, 107, 7482-7489
6. Estrada, E.; Gutierrez, Y. The Balaban J index in the multidimensional space of generalized topological indices. Generalizations and QSPR Match 2001, 44, 155-167
7. Estrada, E. Generalization of topological indices. Chem. Phys. Lett. 2001, 336, 248-252
8. Kier, L. B.; Hall, H. L. Molecular Connectivity. VII. Specific treatment of heteroatoms. J. Pharm. Sci. 1976, 65, 1806-1809
9. Kier, L. B.; Hall, L. H. Molecular Connectivity in Chemistry and Drug Research; Academic: New York, 1976
10. Randić, M. On characterization of molecular branching. J. Am. Chem. Soc. 1975, 97, 6609-6615
11. Kier, L. B.; Murray, W. J.; Randić, M.; Hall, L. H. Molecular connectivity V: Connectivity series concept applied to density. J. Pharm. Sci. 1976, 65, 1226-1230
12. Barysz, M.; Jashari, G.; Lall, R. S.; Srivastave, V. K.; Trinajstić, N. On the distance matrix of molecules containing heteroatoms. In Applications of Chemical Topology and Graph Theory. King., R. B. Ed.; Elsevier: Amsterdam, 1983; pp. 222-227
13. Balaban, A. T. Chemical graphs. 48. Topological index J for heteroatom-containing molecules taking into account periodicities of elements properties. Math. Chem. (MATCH) 1986, 21, 115-122
14. Ivanciuc, O; Ivanciuc, T.; Cabrol-Bass, D.; Balaban, T. Comparison of weighted schemes for molecular graph descriptors: Application in quantitative structure - retention relationship for alkylphenols in gas-liquid chromatography. J. Chem. Inf. Comput. Sci. 2000, 40, 732-743
15. Ivanciuc, O; Ivanciuc, T.; Balaban, T. Design of topological indices. Part 10. Parameters based on electronegativity and covalent radius for the computation of molecular graph descriptors for heteroatom-containing molecules. J. Chem. Inf. Comput. Sci. 1998, 38, 395-401
16. Balaban, A. T. Highly discriminating distance-based topological index. Chem. Phys. Lett. 1982, 80, 399-404
17. Antipin, I. S., Arslanov, N. A., Palyulin, V. A., Konovalov, A. I., Zefirov, N. S. Solvation topological index. Topological description of dispersion interaction (in Russian). Dokl. Akad. Nauk. SSSR, 1991, 316, 925-927
18. Antipin, I. S., Arslanov, N. A., Palyulin, V. A., Konovalov, A. I., Zefirov, N. S. Prognosis of enthalpy[y of nonspecific salvation of organic nonelectrolytes (in Russian). Dokl. Akad. Nauk. SSSR, 1993, 316, 173-176; [Chem. Abstr. 1993, 120, 133743]
19. Antipin, I. S., Arslanov, N. A., Palyulin, V. A., Konovalov, A. I., Zefirov, N. S. Prognosis of enthalpy[y of nonspecific salvation of organic nonelectrolytes (in Russian). Dokl. Akad. Nauk. SSSR, 1993, 316, 173-176; [Chem. Abstr. 1993, 120, 133743]
20. Zefirov, N. S.; Palyulin, V. A. QSAR for boiling points of "small" sufides. Are the "High-Quality Structure-Property- Activity Regressions" the real high quality QSAR models?" J. Chem. Inf. Comput. Sci. 2001, 41, 1022-1027
21. Katrizky, A. R.; Lobanov, V. S.; Karelson, M. CODESSA (COmprehensive Descriptors for Structural and Statistical Analysis), University of Florida, Gainesville. FL. 1995
22. Randić, M. Resolution of ambiguities in structure-property studies by use of orthogonal descriptors. J. Chem. Inf. Comput. Sci. 1991, 31, 311-320
23. Randić, M. Orthogonal molecular descriptors. New J. Chem. 1991, 15, 517-525
24. Randić, M. Correlation of enthalpy of°Ctanes with orthogonal connectivity indices. J. Mol. Struct. (Theochem) 1991, 233, 45-59
25. Randić, M. Fitting of nonlinear regressions by orthogonalized power series. J. Comput. Chem. 1992, 14, 363-370
26. Wu, L.; Zhang, W-J. Comparison of different methods for variable selection. Anal. Chim. Acta 2001, 446, 477-483
27. Lučić, B.; Amić, D.; Trinajstić, N. Nonlinear multivariate regressions outperforms several concisely designed neural networks on three QSRP data set. J. Chem. Inf. Comput. Sci. 2000, 40, 403-413
28. Randić, M. Retro-regression - another important multivariate regression improvement. J. Chem. Inf. Comput. Sci. 2001, 41, 602-606
29. Randić, M.; Zupan, J. M. On the structural interpretation of topological indices. In: "Topology in Chemistry. Discrete Mathematics of Molecules"; Rouvray, D. H.; King, R. B., Eds.; Horwood Publishing Series in Chemical Science, Horwood Publ. Ltd.: Chichester, U.K. 2002; pp. 249-291.
30. Randić, M.; Zupan, J. On intereptation of well-known topological indices. J. Chem. Inf. Comput. Sci. 2001, 41, 550-560
31. Randić, M.; Balaban, A. T.; Basak, S. C. On structural interpretation of several distance related topological indices. J. Chem. Inf. Comput. Sci. 2001, 41, 593-601
32. Randić, M.; Basak, N. Novel graphical matrix and novel distance based molecular descriptors. Croat. Chem. Acta (in press)
33. Randić, M. Novel graph theoretical approach to heteroatoms in quantitative structure-activity relationships. Chemometrics Intel. Lab. Systems 1991, 10, 213-227
34. Randić, M. On computation of optimal parameters for multivariate analysis of structure-property relationship. J. Comput. Chem. 1991, 12, 970-980
35. Randić, M.; Dobrowolski, J. Cz. Optimal molecular connectivity descriptors for nitrogencontaining molecules. Int. J. Quantum Chem. 1998, 70, 1209-1215
36. Randić, M. High quality structure-property regressions: boiling points of smaller alkanes. New J. Chem. 2000, 24, 165-171
37. Randić, M.; Basak. S. C. Construction of high quality structure-property-activity regressions: the boiling points of sulfides. J. Chem. Inf. Comput. Sci. 2000, 40, 899-905
38. f versus the traditional descriptors: A comparative study of 1chif against descriptors of CODESSA. J. Chem. Inf. Comput. Sci. 2001, 41, 631-638.
39. f in QSAR: Toxicity of aliphatic ethers. J. Chem. Inf. Comput. Sci. 2001, 41, 614-618
40. f against descriptors of CODESSA. J. Chem. Inf. Comput. Sci. 2001, 41, 631-638
41. Randić, M.; Plavšić, D.; Lerš, N. Variable connectivity index for cycle-containing structures. . J. Chem. Inf. Comput. Sci. 2001, 41, 657-662
42. Randić, M.; Mills, D.; Basak, S. C. On use of variable connectivity index for characterization of amino acids. Int. J. Quantum Chem. Int. J. Quantum Chem. 2000, 80, 1199-1209
43. Liu, D.; Zhong, C. Modeling of the heat capacity of polymers with the variable connectivity index. Polymer J. 2002, 34, 954-961
44. Zhong, C.; He, J.; Xia, Z; Li, Y. Estimation of activity for Efavirenz analogous with the K 103N mutant of HIV reverse transcriptase using variable connectivity indices. Bioorg. Med. Chem. Lett. (submitted)
45. Randić, M.; Pompe, M. On characterization of the CC double bond in alkenes. SAR & QSAR in Environ. Res. 1999, 10, 451-471
46. Randić, M.; Basak. S. C. Optimal molecular descriptors based on weighted path numbers. J. Chem. Inf. Comput. Sci. 1999, 39, 261-266
47. Randić, M.; Basak. S. C. A new descriptor for structure-property and structure-activity correlations. J. Chem. Inf. Comput. Sci. 2001, 41, 650-656
48. Randić, M.; Pompe, M. The variable molecular descriptors based on distance related matrices, J. Chem. Inf. Comput. Sci. 2001, 41, 575-581
49. Krenkel, G.; Castro, E. A.; Toropov, A. A. Improved molecular descriptors based on the optimization of correlation weights of local graph invariants. J. Mol. Struct. - Theochem. 2001, 542, 107-113
50. Randić, M.; Pompe, M. (to be published)
51. Cammarata, A. Molecular topology and aqueous solubility of aliphatic alcohols, J. Pharm. Sci. 1979, 68, 839-842