European Journal of Chemistry

Prediction of n-octanol-water partition coefficient for polychlorinated biphenyls from theoretical molecular descriptors



Main Article Content

Majid Safdari
Hassan Golmohammadi

Abstract

A quantitative structure-property relationship (QSPR) study was performed to develop models that relate the structures of 133 polychlorinated biphenyls to their n-octanol-water partition coefficients (log Kow). Molecular descriptors were derived solely from 3D structures of the molecules. The genetic algorithm-partial least squares (GA-PLS) method was applied as a variable selection tool.  The partial least square (PLS) method was used to select the best descriptors and the selected descriptors were used as input neurons in neural network model. These descriptors are: Balabane index (J), XY Shadow (SXY), Kier shape index (order 3) (3к), Wiener index (W) and Maximum valency of C atom (VmaxC). The use of descriptors calculated only from molecular structure eliminates the need for experimental determination of properties for use in the correlation and allows for the estimation of log Kow for molecules not yet synthesized. The root mean square errors for ANN predicted partition coefficients of training, test and external validation sets were 0.063, 0.112 and 0.126, respectively, while these values are 0.230, 0.164 and 0.297 for the PLS model, respectively. Comparison between these values and other statistical parameters for these two models revealed the superiority of the ANN over the PLS model.

1_4_266_275_800


icon graph This Abstract was viewed 1295 times | icon graph Article PDF downloaded 604 times

How to Cite
(1)
Safdari, M.; Golmohammadi, H. Prediction of N-Octanol-Water Partition Coefficient for Polychlorinated Biphenyls from Theoretical Molecular Descriptors. Eur. J. Chem. 2010, 1, 266-275.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Wania, F.; Mackay, D. Ambio. 1993, 22, 10-18.

[2]. Giesy, J. P.; Kannan, K. Crit. Rev. Toxicol. 1998, 28, 511- 569.
doi:10.1080/10408449891344263
PMid:9861526

[3]. King, C. M.; King, R. B.; Bhattacharyya, N. K.; Newton, M. G. Organomet. Chem. 2000, 600, 63-70.
doi:10.1016/S0022-328X(00)00031-0

[4]. Sanchez, E.; Fernandez, S. M.; Lopez-Aparicio, P.; Recio, M. N.; Perez-Albarsanz, M. A. Chem. Biol. Interact. 2000, 125, 117-131.
doi:10.1016/S0009-2797(00)00142-3

[5]. Leo, A. J. Chem. Rev. 1993, 93, 1281-1306.
doi:10.1021/cr00020a001

[6]. Klopman, G.; Li, J. Y.; Wang, S. J. Chem. Inf. Comput. Sci. 1994, 34, 752-781.
doi:10.1021/ci00020a009

[7]. Platts, J. A.; Butina, D.; Abraham, M. H.; Hersey, A. J. Chem. Inf. Comput. Sci. 1999, 39, 835-845.
doi:10.1021/ci980339t

[8]. Woodrow, B. N.; Dorsey, J. G. Environ. Sci. Technol. 1997, 31, 2812-2820.
doi:10.1021/es9700313

[9]. Platts, J. A.; Abraham, M. H.; Butina, D.; Hersey, A. J. Chem. Inf. Comput. Sci. 2000, 40, 71-80.
doi:10.1021/ci990427t

[10]. Khadikar, P. V.; Singh, S.; Shrivastava, A. Bioorg. Med. Chem. Lett. 2002, 12, 1125-1128.
doi:10.1016/S0960-894X(02)00086-0

[11]. Chen, J. W.; Xue, X. Y.; Schramm, K. W.; Xie, Q.; Yang, F. L.; Kettrup, A. Chemosphere 2002, 48, 535-544.
doi:10.1016/S0045-6535(02)00041-3

[12]. Niu, J. F.; Yang, Z. F.; Shen, Z. Y.; Long, X. X.; Yu, G. Chemosphere 2006, 64, 658-665.
doi:10.1016/j.chemosphere.2005.10.051
PMid:16343592

[13]. Lu, W.; Chen, Y.; Liu, M.; Chen, X.; Hu, Z. Chemosphere 2007, 69,469-478.
doi:10.1016/j.chemosphere.2007.04.044
PMid:17568650

[14]. Padmanabhan, J.; Parthasarathi, R.; Subramaniana, V.; Chattaraj, P. K. Bioorganic & Medicinal Chemistry 2006, 14, 1021-1028.
doi:10.1016/j.bmc.2005.09.017

[15]. Puzyn, T.; Falandysz, J. Phys. Chem. Ref. Data 2007, 36, 203-214.
doi:10.1063/1.2432888

[16]. Li, L.; Xie, S.; Cai, H.; Bai, X.; Xue, Z. Chemosphere 2008, 72, 1602-1606.
doi:10.1016/j.chemosphere.2008.04.020
PMid:18508108

[17]. Vegas, J. M.; Zufiria, P. J. Neural Networks 2004, 17, 233-245.
doi:10.1016/j.neunet.2003.05.001
PMid:15036341

[18]. Schweitzer, R. C.; Morris, J. B. Anal. Chem. Act. 1999, 384, 285-303.
doi:10.1016/S0003-2670(98)00781-8

[19]. Tong, C. S.; Cheng, K. C. Chemom. Intell. Lab. Syst. 1999, 49, 135-150.
doi:10.1016/S0169-7439(99)00031-3

[20]. Golmohammadi, H.; Fatemi, M. H. Electrophoresis 2005, 26, 3438-3444.
doi:10.1002/elps.200500203
PMid:16110463

[21]. Baher, E.; Fatemi, M. H.; Konoz, E.; Golmohammadi, H. Microchim Acta 2007, 158, 117-122.
doi:10.1007/s00604-006-0675-x

[22]. Konoz, E.; Golmohammadi, H. Anal. Chem. Act. 2008, 619, 157-164.
doi:10.1016/j.aca.2008.04.065
PMid:18558108

[23]. Lui, F.; Liang, Y.; Cao, C. Chemom. Intell. Lab. Syst. 2006, 81, 120-126.
doi:10.1016/j.chemolab.2005.10.004

[24]. Hyperchem, Rel. 4. for Windows, Autodesk, Sansalito, CA, 1995.

[25]. Stewart, J. J. P. Semiempirical Molecular Orbital Program; QCPE, 445 (1983), Version 6, 1990.

[26]. Katritzky, A. R.; Labadov, V. S.; Carelson, M. CODESSA Training Manual, University of Florida, Gainesville, 1995.

[27]. Katritzky, A. R.; Labadov, V. S.; Carelson, M. CODESSA Version 1 Reference Manual, University of Florida, Gainesville, Florida, 1994.

[28]. Goldberg, D. E. Genetic Algorithms in Search, Optimization and Machine learning, Addison-Wesley, New York, 1989.

[29]. Hoskuldsson, A. Prediction Methods in Science and Technology Vol. 1: Basic Theory, Thur Publishing, Denmark, 1996.

[30]. Hasegawa, K.; Kimura, T.; Funatsu, K. Quant. Struct. Acta. Relat. 1999, 18, 262-272.

[31]. Leardi, R.; Boggia, R. Terrile, M. J. Chemom. 1992, 6, 267-281.

[32]. Leardi, R.; Gonzalez, A. L. Chemom. Intell. Lab. Sys. 1998, 41, 195-207.
doi:10.1016/S0169-7439(98)00051-3

[33]. Lorber, A.; Wangen, L.; Kowalsky, B. R. J. Chemom. 1987, 1, 19-31.
doi:10.1002/cem.1180010105

[34]. Khayamian, T.; Ensafi, A. A.; Hemmateenejad, B. Talanta 1999, 49, 587-596.
doi:10.1016/S0039-9140(99)00052-1

[35]. Shamsipur, M.; Hemmateenejad, B.; Akhond, M.; Sharghi, H. Talanta 2001, 54, 1113-1120.
doi:10.1016/S0039-9140(01)00374-5

[36]. Hoskuldsson, A. Chemom. Intell. Lab. Syst. 2001, 55, 23-38.
doi:10.1016/S0169-7439(00)00113-1

[37]. MATLAB 7. 0, The Mathworks Inc., Natick, MA, USA, http://www.mathworks.com.

[38]. Zupan, J.; Gasteiger, J. Neural Network in Chemistry and Drug Design; Wiley-VCH. Weinheim, 1999.

[39]. Beal, T. M.; Hagan, H. B.; Demuth, M., Neural Network Design; PWS, Boston, 1996.

[40]. Zupan, J.; Gasteiger, J. Neural Networks for Chemists: an Introduction; VCH. Weinheim, 1993.

[41]. Blank, T. B.; Brown, S. T. Anal. Chem. 1993, 65, 3081-3089.
doi:10.1021/ac00069a023

[42]. Jalali-Heravi, M.; Fatemi, M. H. J. Chromatogr. A 2001, 915, 177-183.
doi:10.1016/S0021-9673(00)01274-7

[43]. Golbraikh, A.; Tropsha, A. J. Mol. Graphics Modell. 2002, 20, 269-276.
doi:10.1016/S1093-3263(01)00123-1

[44]. Roy, P. P.; Roy, K. QSAR Comb. Sci. 2008, 27, 302-313.
doi:10.1002/qsar.200710043

[45]. Maldonado, A. G.; Doucet, J. P.; Petitjean, M.; Fan, B. T. Mol. Divers. 2006, 10, 39-79.
doi:10.1007/s11030-006-8697-1
PMid:16404528

[46]. Sannigrahi, A. B. Adv. Quant. Chem. 1992, 23, 301-351.
doi:10.1016/S0065-3276(08)60032-5

[47]. Wiener, H. J. Am. Chem. Soc. 1947, 69, 17-20.
doi:10.1021/ja01193a005
PMid:20291038

[48]. Kier, L. B. Computational Chemical Graph Theory Rouvray, D. H. (editor), Nova Science Publishers, New York, 1990, pp. 151-174.

[49]. Kowalski, B. R. (Ed.), Chemometrics, Reidel, Dordrecht, 1984.

[50]. Stankevich, M. I.; Stankevich, I. V.; Zefirov, N. S.; Russ. Chem. Rev. 1988, 57, 191-208.
doi:10.1070/RC1988v057n03ABEH003344

[51]. El-Basil, S.; Randic, M. Adv. Quant. Chem. 1992, 24, 239-290.
doi:10.1016/S0065-3276(08)60103-3

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).