CORAL: QSPR model of water solubility based on local and global SMILES attributes

Chemosphere

Volumn 90, Issue 2, 2013, Pages 877-880

  Toropov, Andrey A ^a   Toropova, Alla P ^a   Benfenati, Emilio ^a   Gini, Giuseppina ^b   Leszczynska, Danuta ^c   Leszczynski, Jerzy ^d  

^a MARIO NEGRI INSTITUTE FOR PHARMACOLOGICAL RESEARCH   (Italy)

^b POLITECNICO DI MILANO   (Italy)

^c Jackson State University   (United States)

^d JACKSON STATE UNIVERSITY   (United States)

Author keywords

CORAL software; Monte Carlo technique; QSPR; Water solubility

Indexed keywords

SOLUBILITY; STRUCTURAL OPTIMIZATION;

CORAL SOFTWARES; MONTE CARLO TECHNIQUES; QSPR; QUANTITATIVE STRUCTURE-PROPERTY RELATIONSHIP; REPRODUCIBILITIES; STATISTICAL CHARACTERISTICS; STATISTICAL QUALITY; WATER SOLUBILITIES;

MONTE CARLO METHODS;

WATER;

AQUEOUS SOLUTION; CALIBRATION; CHEMICAL PROPERTY; CHEMICAL SUBSTANCE; MOLECULAR ANALYSIS; MONTE CARLO ANALYSIS; NUMERICAL MODEL; QUANTITATIVE ANALYSIS; SOFTWARE; SOLIDIFICATION; SOLUBILITY;

ARTICLE; CALIBRATION; CHEMICAL STRUCTURE; CORAL SOFTWARE; DATA ANALYSIS SOFTWARE; MODEL; MONTE CARLO METHOD; QUANTITATIVE STRUCTURE PROPERTY RELATION; REPRODUCIBILITY; SIMPLIFIED MOLECULAR INPUT LINE ENTRY SYSTEM; SOLUBILITY;

EID: 84869885324     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2012.07.035     Document Type: Article

References (26)

1. Bhhatarai B., Gramatica P. Prediction of aqueous solubility, vapor pressure and critical micelle concentration for aquatic partitioning of perfluorinated chemicals environ. Sci. Technol. 2011, 45:8120-8128.
2. Duchowicz P.R., Talevi A., Bruno-Blanch L.E., Castro E.A. New QSPR study for the prediction of aqueous solubility of drug-like compounds. Bioorg. Med. Chem. 2008, 16:7944-7955.
3. Furtula B., Gutman I. Relation between second and third geometric-arithmetic indices of trees. J. Chemom. 2011, 25:87-91.
4. García J., Duchowicz P.R., Rozas M.F., Caram J.A., Mirífico M.V., Fernández F.M., Castro E.A. A comparative QSAR on 1,2,5-thiadiazolidin-3-one 1,1-dioxide compounds as selective inhibitors of human serine proteinases. J. Mol. Graph. Model. 2011, 31:10-19.
5. Garro C., Martinez J.C., Duchowicz P.R., Estrada M.R., Zamarbide G.N., Castro E.A. QSAR study and molecular design of open-chain enaminones as anticonvulsant agents. Int. J. Mol. Sci. 2011, 12:9354-9368.
6. 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.
7. Ibezim E., Duchowicz P.R., Ortiz E.V., Castro E.A. QSAR on aryl-piperazine derivatives with activity on malaria. Chemom. Intell. Lab. 2012, 110:81-88.
8. Liu R.F., So S.S. Development of quantitative structure-property relationship models for early ADME evaluation in drug discovery. 1. Aqueous solubility. J. Chem. Inf. Comput. Sci. 2001, 41:1633-1639.
9. Marino D.J.G., Peruzzo P.J., Castro E.A., Toropov A.A. QSAR carcinogenic study of methylated polycyclic aromatic hydrocarbons based on topological descriptors derived from distance matrices and correlation weights of local graph invariants. Internet Electron. J. Mol. Des. 2002, 1:115-133.
10. Melagraki G., Afantitis A. Ligand and structure based virtual screening strategies for hit-finding and optimization of Hepatitis C virus (HCV) inhibitors. Curr. Med. Chem. 2011, 18:2612-2619.
11. Mullen L.M.A., Duchowicz P.R., Castro E.A. QSAR treatment on a new class of triphenylmethyl-containing compounds as potent anticancer agents. Chemom. Intell. Lab. 2011, 107:269-275.
12. Ojha K., Mitra I., Das R.N., Roy K. Further exploring rm2 metrics for validation of QSPR models. Chemom. Intell. Lab. Syst. 2011, 107:194-205.
13. Peruzzo P.J., Marino D.J.G., Castro E.A., Toropov A.A. QSPR modeling of lipophilicity by means of correlation weights of local graph invariants. Internet Electron. J. Mol. Des. 2003, 2:334-347.
14. Puzyn T., Gajewicz A., Rybacka A., Haranczyk M. Global versus local QSPR models for persistent organic pollutants: balancing between predictivity and economy. Struct. Chem. 2011, 22:873-884.
15. Roy K., Saha A. QSPR with TAU indices: water solubility of diverse functional acyclic compounds. Internet Electron. J. Mol. Des. 2003, 2:475-491.
16. Roy P.P., Leonard J.T., Roy K. Exploring the impact of size of training sets for the development of predictive QSAR models. Chemom. Intell. Lab. 2008, 90:31-42.
17. Tetko I.V., Tanchuk V.Yu., Kasheva T.N., Villa A.E.P. Estimation of aqueous solubility of chemical compounds using E-state indices. J. Chem. Inf. Comput. Sci. 2001, 41:1488-1493.
18. Toropov A.A., Toropova A.P. QSAR modeling of mutagenicity based on graphs of atomic orbitals. Internet Electron. J. Mol. Des. 2002, 1:108-114.
19. Toropov A.A., Toropova A.P., Benfenati E. SMILES-based optimal descriptors: QSAR modelling of carcinogenicity by balance of correlations with ideal slopes. Eur. J. Med. Chem. 2010, 45:3581-3587.
20. Toropov A.A., Toropova A.P., Benfenati E., Gini G., Leszczynska D., Leszczynski J. CORAL: quantitative structure-activity relationship models for estimating toxicity of organic compounds in rats. J. Comput. Chem. 2011, 32:2727-2733.
21. Toropova A.P., Toropov A.A., Diaza R.G., Benfenati E., Gini G. Analysis of the co-evolutions of correlations as a tool for QSAR-modeling of carcinogenicity: an unexpected good prediction based on a model that seems untrustworthy. Cent. Eur. J. Chem. 2011, 9:165-174.
22. Toropova A.P., Toropov A.A., Benfenati E., Gini G. Co-evolutions of correlations for QSAR of toxicity of organometallic and inorganic substances: An unexpected good prediction based on a model that seems untrustworthy. Chemom. Intell. Lab. Sys. 2011, 105:215-219.
23. Toropova A.P., Toropov A.A., Benfenati E., Gini G., Leszczynska D., Leszczynski J. CORAL: QSPR models for solubility of [C 60] and [C 70] fullerene derivatives. Mol. Divers. 2011, 15:249-256.
24. Toropova A.P., Toropov A.A., Benfenati E., Gini G., Leszczynska D., Leszczynski J. CORAL: quantitative structure-activity relationship models for estimating toxicity of organic compounds in rats. J. Comput. Chem. 2011, 32:2727-2733.
25. Weininger D. SMILES. 3. Depict. Graphical depiction of chemical structures. J. Chem. Inf. Comput. Sci. 1990, 30:237-243.
26. Yan A., Gasteiger J. Prediction of aqueous solubility of organic compounds based on a 3D structure representation. J. Chem. Inf. Comput. Sci. 2003, 43:429-434.