Overall Connectivities/Topological Complexities: A New Powerful Tool for QSPR/QSAR

Journal of Chemical Information and Computer Sciences

Volumn 40, Issue 4, 2000, Pages 934-941

  Bonchev, Danail ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001186084     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci990120u     Document Type: Article

References (68)

1. Harary, F. Graph Theory; Addison-Wesley: Reading, MA, 1969.
2. Chemical Applications of Graph Theory; Balaban A. T., Ed.; Academic Press: London, 1976.
3. Trinajstić, N. Chemical Graph Theory, 2nd ed.; CRC Press: Boca Raton, FL, 1992.
4. Morgan, H. L. The Generation of a Unique Machine Description for Chemical Structures - A Technique Developed at Chemical Abstract Service. J. Chem. Doc. 1965, 5, 107-113.
5. Razinger, M. Extended Connectivity in Chemical Graphs. Theor. Chim. Acta 1982, 61, 581-586. Razinger, M. Discrimination and Ordering of Chemical Structures by the Number of Walks. Theor. Chim. Acta 1986, 70, 365-378. Razinger, M.; Chretien, J. R.; Dubois, J.-E. Structural Selectivity of Topological Indexes in Alkane Series. J. Chem. Inf. Comput. Sci. 1985, 25, 23-27.
6. Razinger, M. Extended Connectivity in Chemical Graphs. Theor. Chim. Acta 1982, 61, 581-586. Razinger, M. Discrimination and Ordering of Chemical Structures by the Number of Walks. Theor. Chim. Acta 1986, 70, 365-378. Razinger, M.; Chretien, J. R.; Dubois, J.-E. Structural Selectivity of Topological Indexes in Alkane Series. J. Chem. Inf. Comput. Sci. 1985, 25, 23-27.
7. Razinger, M. Extended Connectivity in Chemical Graphs. Theor. Chim. Acta 1982, 61, 581-586. Razinger, M. Discrimination and Ordering of Chemical Structures by the Number of Walks. Theor. Chim. Acta 1986, 70, 365-378. Razinger, M.; Chretien, J. R.; Dubois, J.-E. Structural Selectivity of Topological Indexes in Alkane Series. J. Chem. Inf. Comput. Sci. 1985, 25, 23-27.
8. Rücker, G.; Rücker, C. Counts of All Walks as Atomic and Molecular Descriptors. J. Chem. Inf. Comput. Sci. 1993, 33, 683-695.
9. Toropov, A. A.; Toropova, A. P.; Ismailov, T. T.; Voropaeva, N. L.; Ruban, I. N. Extended Molecular Connectivity: Prediction of the Boiling Points of Alkanes. J. Strukt. Khim. 1997, 38, 1154-1159.
10. Gutman, I.; Rušćić, B.; Trinajstić, N.; Wilcox, C. W., Jr. Graph Theory and Molecular Orbitals. 12. Acyclic Polyenes. J. Chem. Phys. 1975, 62, 3399-3405.
11. Randić, M. On Characterization of Molecular Branching. J. Am. Chem. Soc. 1975, 97, 6609-6615.
12. Kier, L. B.; Hall, L. H.; Murray, W. J.; Randić, M. Molecular Connectivity I: Relationship to Nonspecific Local Anesthesia. J. Pharm. Sci. 1975, 64, 1971-1974.
13. Kier, L. B.; Hall, L. H. Molecular Connectivity in Chemistry and Drug Research; Academic Press: New York, 1976.
14. Kier, L. B.; Hall, L. H. Molecular Connectivity in Structure-Activity Analysis: Research Studies Press: Chichester, U.K., 1986.
15. Balaban, A. T. Highly Discriminating Distance-Based Topological Index. Chem. Phys. Lett. 89, 399-404.
16. Kier, L. B.; Hall, L. H.; Frazer, J. W. An Index of Electrotopological State for Atoms in Molecules. J. Math. Chem. 1991, 7, 229-241.
17. Toropov, A. A.; Toropova, A. P.; Ismailov, T. T.; Bonchev, D. 3D Weighting of Molecular Descriptors for QSPR/QSAR by the Method of Ideal Symmetry(MIS). 1. Application to Boiling Points of Alkanes. THEOCHEM 1998, 424, 237-247.
18. Estrada, E. Graph Theoretical Invariant of Randic Randić Revisited. J. Chem. Inf. Comput. Sci. 1995, 35, 1022-1025. Estrada, E.; Guevara, N.; Gutman, I. Extension of Edge Connectivity Index. Relationship to Line Graph Indices and QSPR Applications. J. Chem. Inf. Comput. Sci. 1998, 38, 428-431.
19. Estrada, E. Graph Theoretical Invariant of Randic Randić Revisited. J. Chem. Inf. Comput. Sci. 1995, 35, 1022-1025. Estrada, E.; Guevara, N.; Gutman, I. Extension of Edge Connectivity Index. Relationship to Line Graph Indices and QSPR Applications. J. Chem. Inf. Comput. Sci. 1998, 38, 428-431.
20. Randić, M. Augmented Valence - Novel Graph Theoretical Index with an Apparent Interpretation. Int. J. Quantum Chem., in press.
21. Bonchev, D.; Seitz, W. A. The Concept of Complexity in Chemistry. In Concepts in Chemistry: Contemporary Challeng; Rouvray, D. H., Ed.; Research Studies Press: Taunton, U.K., 1996; pp 353-381.
22. Kier, L. B.; Testa, B. Complexity and Emergence in Drug Research. Adv. Drug Res. 1995, 26, 1-43.
23. Bertz, S. H. The First General Index of Molecular Complexity. J. Am. Chem. Soc. 1981, 103, 3599-3601.
24. Bertz, S. H. A Mathematical Model of Molecular Complexity. In Chemical Applications of Topology and Graph Theory; King, R. B., Ed.; Elsevier: New York, 1983; pp 206-221.
25. Rashevsky, N. Life, Information Theory, and Topology. Bull. Math. Biophys. 1955, 17, 229-235.
26. Mowshovitz, A. Entropy and the Complexity of Graphs. 1. An Index of the Relative Complexity of a Graph. Bull. Math. Biophys. 1968, 30, 175-204.
27. Shannon, C., and Weaver, W. Mathematical Theory of Communications; University of Illinois Press: Urbana, IL, 1949.
28. Bonchev, D. Information-Theoretic Indices for Characterization of Chemical Structures; Research Studies Press: Chichester, U.K., 1983; 249 pp.
29. Bonchev, D. Kolmogorov's Information, Shannon's Entropy, and Topological Complexity of Molecules. Bulg. Chem. Commun. 1995, 28, 567-582.
30. Bonchev, D.; Polansky, O. E. On the Topological Complexity of Chemical Systems. In Graph Theory and Topology in Chemistry; King, R. B., Rouvray, D. H., Eds.; Elsevier: Amsterdam, 1987; pp 126-158.
31. Bertz, S. H.; Wright, W. F. The Graph Theory Approach to Synthetic Analysis: Definition and Application of Molecular Complexity and Synthetic Complexity. Graph Theory Notes N. Y. Acad. Sci. 1998, 32-48.
32. Minoli, D. Combinatorial Graph Complexity. Atti. Acad. Naz. Lincei Rend. 1976, 59, 651-661.
33. Bonchev, D. The Problems of Computing Molecular Complexity. In Computational Chemical Graph Theory; Rouvray, D. H., Ed.; Nova Publications: New York, 1990; pp 34-67.
34. Bonchev, D.; Trinajstić, N. Information Theory, Distance Matrix, and Molecular Branching. J. Chem. Phys. 1977, 67, 4517-4533.
35. Ruch, E.; Gutman, I. The Branching Extent of Graphs. J. Comb. Inf. Syst. Sci. 1979, 4, 285-295.
36. Bonchev, D.; Mekenyan, O.; Trinajstić, N. Topological Characterization of Cyclic Structures. Int. J. Quantum Chem. 1980, 17, 845-893.
37. Bertz, S. H. Branching in Graphs & Molecules. Discr. Appl. Math. 1988, 19, 65-83.
38. Bonchev, D. Topological order in molecules. 1. Molecular Branching Revisited. THEOCHEM 1995, 336, 137-156.
39. Randić, M. On Molecular Branching. Acta Chim. Slov. 1997, 44, 57-77.
40. Randić, M. On Characterization of Cyclic Structures. J. Chem. Inf. Comput. Sci. 1997, 37, 1063-1071.
41. Nikolić, S.; Trinajstić, N.; Jurić, A.; Mihalić, Z.; Krilov, G. Complexity of Some Interesting (Chemical) Graphs. Croat. Chem. Acta 1996, 69, 883-897.
42. Gutman, I.; Mallion, R. B.; Essam, J. W. Counting the Spanning Trees of a Labeled Molecular Graph. Mol. Phys. 1983, 50, 859-877.
43. Bonchev, D.; Kamensky, D.; Temkin, O. N. Complexity Index for the Linear Mechanisms of Chemical Reactions. J. Math. Chem. 1987, 1, 345-388.
44. Gordeeva, K.; Bonchev, D.; Kamenski, D.; Temkin, O. N. Enumeration, Coding, and Complexity of Linear Reaction Mechanisms, J. Chem. Inf. Comput. Sci. 1994, 34, 244-247.
45. Temkin, O. N.; Zeigarnik, A. V.; Bonchev, D. Chemical Reaction Networks. A Graph Theoretical Approach; CRC Press: Boca Raton, FL, 1996; 286 pp.
46. Kolmogorov, A. N. Three Approaches to the Quantitative Definition of Information. Probl. Inf. Transm. (Engl. Transl.) 1965, 1, 1-7.
47. Bonchev, D. Novel Indices for the Topological Complexity of Molecules. SAR QSAR Environ. Res. 1997, 7, 23-43.
48. Bonchev, D. Overall Connectivity and Molecular Complexity. In Topological Indices and Related Descriptors; Devillers, J., Balaban, A. T., Eds.; Gordon and Breach: Reading, U.K., 1999; pp 361-401.
49. Dubois, J.-E. Ordered Chromatic Graphs and Limited Environment Concept. In Chemical Applications of Graph Theory; Balaban A. T., Ed.; Academic Press: London, 1976.
50. Willet, P. Some Heuristics for Nearest-Neighbor Searching in Chemistry-Structure Files. J. Chem. Inf. Comput. Sci. 1983, 23, 3, 22-25.
51. Klopman, G. Artificial Intelligence Approach to Structure-Activity Studies. Computer Automated Structure Evaluation of Biological Activities of Organic Molecules. J. Am. Chem. Soc. 1984, 106, 7315-7321.
52. Gordon, M.; Kennedy, J. W. The Graph-Like State of Matter. Part 2. TCGI Schemes for the Thermodynamics of Alkanes and the Theory of Inductive Inference. J. Chem. Soc., Faraday Trans. 2 1973, 69, 484-504.
53. Panaye, A.; Doucet, J.-P.; Fan, B. T. Topological Approach of C-13 NMR Spectral Simulation. Application to Fuzzy Substructures. J. Chem. Inf. Comput. Sci. 1993, 33, 3, 258-265.
54. Bertz, S.; Herndon, W. C. Similarity of Graphs and Molecules. In Artificial Intelligence Applications in Chemistry; American Chenical Society: Washington, DC, 1986; pp 169-175.
55. Matula, D. W. On the Number of Subtrees in a Symmetric n-ary Trees. SIAM J. Appl. Math. 1970, 18, 688-703.
56. Bone, R. G. A.; Villar, H. O. Exhaustive Enumeration of Molecular Substructures. J. Comput. Chem. 1997, 18, 86-107.
57. Bertz, S. H.; Sommer, T. J. Rigorous Mathematical Approaches to Strategic Bonds and Synthetic Analysis Based on Conceptually simple new complexity indices. Chem. Commun. 1997, 2409-2410.
58. Bonchev, D.; Gordeeva, E. Partial Orderings Induced by Topological Complexity. MATCH, in press.
59. Bonchev, D. The Concept of Topological Complexity as Overall Connectivity. In Mathematical Chemistry Series. Volume 7, Complexity in Chemistry; Bonchev, D., Rouvray, D. H., Eds.; Gordon & Breach: Reading, U.K., in preparation.
60. Bonchev, D.; Mekenyan, O.; Trinajstić, N. Isomer Discrimination by Topological Information Approach. J. Comput. Chem. 1981, 2, 127-148.
61. Rücker, G.; Rücker, C. Walk Counts, Labirinthicity, and Complexity of Acyclic and Cyclic Graphs and Molecules. J. Chem. Inf. Comput. Sci. 2000, 40, 99-106.
62. Kier, L. B.; Hall, L. H. Derivation and Significance of Valence Molecular Connectivity. J. Pharm. Sci. 1981, 70, 583-589.
63. Needham, D. E.; Wei, I.-C.; Seybold, P. G. Molecular Modeling of the Physical Properties of the Alkanes. J. Am. Chem. Soc. 1988, 110, 4186-4194.
64. Selected Values of Properties of Hydrocarbons and Related Compounds; Research Project 44; American Petroleum Institute: Pittsburgh, PA, 1977.
65. Garbalena, M.; Herndon, W. C. Optimum Graph-Theoretical Models for Enthalpic Properties of Alkanes. J. Chem. Inf. Comput. Sci. 1992, 32, 37-42.
66. Mekenyan, O.; Karabunarliev, S.; Bonchev, D. The OASIS Concept for Predicting Biological Activity of Chemical Compounds. J. Math. Chem. 1990, 4, 207-215.
67. Bonchev, D.; Balaban, A. T.; Mekenyan, O. Generalization of the Graph Center Concept, and Derived Topological Indices. J. Chem. Inf. Comput. Sci. 1980, 20, 106-113.
68. Bonchev, D. Overall Distance of a Graph. A Concept Generalizing the Wiener Number. To be submitted for publication.