WHIM-3D-QSPR APPROACH FOR PREDICTING AQUEOUS SOLUBILITY OF CHLORINATED HYDROCARBONS

https://doi.org/10.22146/ijc.21650

Oman Zuas(1*)

(1) Analytical Chemistry and Standard Division, Research Centre for Chemistry, Indonesian Institute of Sciences, Kawasan PUSPIPTEK, Serpong, 15314, Tangerang, Banten
(*) Corresponding Author

Abstract


The weighted holistic invariant molecular-three dimensional-quantitative structure property relationship (WHIM-3D-QSPR) approach has been applied to the study of the aqueous solubility (- log Sw) of chlorinated hydrocarbon compounds (CHC's). The obtained QSPR model is predictive and only requires four WHIM-3D descriptors in the calculation. The correlation equation of the model that is based on a training set of 50 CHC's compound has statistical parameters: standard coefficient correlation (R2) = 0.948; cross-validated correlation coefficients (Q2) = 0.935; Standard Error of Validation (SEV) = 0.35; and average absolute error (AAE) = 0.31. The application of the best model to a testing set of 50 CHC's demonstrates a reliable result with good predictability. Besides, it was possible to construct new model by applying WHIM-3D-QSPR approach without require any experimental physicochemical properties in the calculation of aqueous solubility.


Keywords


WHIM-3D; QSPR; aqueous solubility; - Log Sw; chlorinated hydrocarbons; CHC's

Full Text:

Full Text Pdf


References

[1] Butina, D., and Gola, J.M.R., 2003, J. Chem. Inf. Comput. Sci., 43, 837-841

[2] Cal, K., 2006, Yakugaku Zasshi, 126, 307-309.

[3] Loftsson, T., and Hreinsdóttir, D., 2006, AAPS Pharm.Sci.Tech. 7, E1-E4.

[4] Johnson, S.R., and Zheng, W., 2006, The AAPS Pharm.Sci.Tech., 8, E27-E40.

[5] Wang, Y.L., Hu, L.D., and Wu, L.Y., 2006, Int. J. Mol. Sci., 7, 47-58.

[6] Cheng, A.J., and Merz, K.M.J., 2003, J. Med. Chem., 46, 3572-3580.

[7] Erös, D., Kéria, G., Kövesdi, I., Szántai-Kis, C., Mészáros, G., and Örfi, L., 2004, Mini-Rev. Med. Chem., 4, 167-177.

[8] Delaney, J.S., 2005, Drug Discov. Today, 10, 289-295.

[9] Ghasemi, J., and Saaidpour, S., 2007, Chem. Pharm. Bull., 55, 669-674.

[10] Huuskonen, J., Salo, M., and Taskinen, J., 1997, J. Pharm. Sci., 86, 450-454.

[11] Huuskonen, J., Salo, M., and Taskinen, J., 1998, J. Chem. Inf. Comput. Sci., 38, 450-456.

[12] William, L.J., and Erin, M.D., 2000, Med. Chem. Lett., 10, 1155-1158.

[13] William L. J., and Erin, M.D., 2002, Adv. Drug Del. Rev., 54, 355-366.

[14] Huuskonen, J., 2000, J. Chem. Inf. Comput. Sci., 40, 773-777.

[15] Catana, C., Gao, H., Orrenius, C., and Stouten, P. F. W., 2005, J. Chem. Inf. Model, 45, 170-176.

[16] Delgado, E.J., 2002, Fluid. Phase. Equilibr., 199, 101-107.

[17] Hypercube, I. 2002, HyperChem Release 7.0 for Windows, Hypercube. Inc., Gainesville, Florida, USA.

[18] Telete, Srl., 2006, DRAGON for Windows (Software for Molecular Descriptor Calculations) Version 5.4, Talete, Srl., Milano, Italy, http://www.telete.mi.it.

[19] Todeschini, R., 2007, Milano Chemometric and QSAR Research Group, University of Milano, Milano Italy, http://michem.disat.unimib.it/chm/ index.htm. Accessed on 30 September 2007.

[20] Gramatica, P., 2006, QSAR & Combinatorial Sciences, 25, 327-332.

[21] Todeschini, R., and Gramatica, P., 2006, Quantitative Structure-Activity Relationships, 16, 113 – 119.

[22] Todeschini, R., Bettiol, C., Giurin, G., Gramatica, P., Miana, P., and Argese, E., 1996, Chemosphere, 33, 71-79.

[23] Chiorboli, C., Gramatica, P., Piazza, R., Pino, A., and Todeschini, R., 1997, SAR and QSAR in Environmental Research, 7, 133-150.

[24] Todeschini, R., Vighi, M., Finizio, A., and Gramatica, P, 1997, SAR and QSAR in Environmental Research, 7, 173 – 193.

[25] Foundation, A.S., 2004, SPSS Release 12.0 for Windows, SPSS, Inc., Chicago, Illinois, USA, http://www.spss.com/.

[26] Hawkins, D.M., Basak, S.C., and Mills, D., 2003, J. Chem. Inf. Comput. Sci., 43, 579-586.

[27] Kohavi, R., 1995., A study of cross-validation and bootstrap for accuracy estimation and model selection. In Proceedings of the Fourteenth International Conference on Artificial Intelligence (IJCAI), San Mateo, 1137-1143.

[28] Wold, S., 1991, Quant. Struct.-Act. Relat., 10, 191-193.

[29] Ribeiro, F.A.D., and Ferreira, M.M.C., 2003, Journal of Molecular Structure: THEOCHEM., 663, 109-126.



DOI: https://doi.org/10.22146/ijc.21650

Article Metrics

Abstract views : 1321 | views : 905


Copyright (c) 2010 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 

Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web Analytics View The Statistics of Indones. J. Chem.