European Journal of Chemistry 2010, 1(4), 266-275 | doi: https://doi.org/10.5155/eurjchem.1.4.266-275.59 | Get rights and content






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


Majid Safdari (1) , Hassan Golmohammadi (2,*)

(1) Department of Chemistry, Esfahan University of Technology, Esfahan, IR-84156-8311, Iran
(2) Department of Chemistry, Mazandaran University, Babolsar, IR-47415, Iran
(*) Corresponding Author

Received: 12 Apr 2010 | Revised: 24 Jul 2010 | Accepted: 28 Jul 2010 | Published: 22 Dec 2010 | Issue Date: December 2010

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.

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Keywords


Quantitative Structure-Property Relationship; n-Octanol–water partition coefficient; Artificial neural network; Partial least squares; Genetic algorithm

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DOI: 10.5155/eurjchem.1.4.266-275.59

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Mazandaran University

Citations

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[1]. Don Mackay, Jan C. Myland, Keith B. Oldham, J. Mark Parnis
Pitfalls in the application of statistics to chemical data: the determination of the partition ratio $$K_{\mathrm{ow} }$$ K ow as a case in point
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DOI: 10.1007/s10910-018-0862-0
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[2]. Jayshree Annamalai, Vasudevan Namasivayam
Endocrine disrupting chemicals in the atmosphere: Their effects on humans and wildlife
Environment International  76, 78, 2015
DOI: 10.1016/j.envint.2014.12.006
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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

How to cite


Safdari, M.; Golmohammadi, H. Eur. J. Chem. 2010, 1(4), 266-275. doi:10.5155/eurjchem.1.4.266-275.59
Safdari, M.; Golmohammadi, H. Prediction of n-octanol-water partition coefficient for polychlorinated biphenyls from theoretical molecular descriptors. Eur. J. Chem. 2010, 1(4), 266-275. doi:10.5155/eurjchem.1.4.266-275.59
Safdari, M., & Golmohammadi, H. (2010). Prediction of n-octanol-water partition coefficient for polychlorinated biphenyls from theoretical molecular descriptors. European Journal of Chemistry, 1(4), 266-275. doi:10.5155/eurjchem.1.4.266-275.59
Safdari, Majid, & Hassan Golmohammadi. "Prediction of n-octanol-water partition coefficient for polychlorinated biphenyls from theoretical molecular descriptors." European Journal of Chemistry [Online], 1.4 (2010): 266-275. Web. 6 Aug. 2020
Safdari, Majid, AND Golmohammadi, Hassan. "Prediction of n-octanol-water partition coefficient for polychlorinated biphenyls from theoretical molecular descriptors" European Journal of Chemistry [Online], Volume 1 Number 4 (22 December 2010)

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DOI Link: https://doi.org/10.5155/eurjchem.1.4.266-275.59

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