注册
ISSN 1000-6818CN 11-1892/O6CODEN WHXUEU
物理化学学报 >> 2017,Vol.33>> Issue(5)>> 918-926     doi: 10.3866/PKU.WHXB201701163         English Abstract
Developing a Support Vector Machine Based QSPR Model to PredictGas-to-Benzene Solvation Enthalpy of Organic Compounds
GOLMOHAMMADI Hassan1, DASHTBOZORGI Zahra2, KHOOSHECHIN Sajad2
1 Young Researchers and Elite Club, Yadegar-e-Imam Khomeini (RAH) Shahr-e-Rey Branch, Islamic Azad University, Tehran, Iran;
2 Young Researchers and Elite Club, Central Tehran Branch, Islamic Azad University, Tehran, Iran
Full text: PDF (1991KB) HTML 输出: BibTeX | EndNote (RIS) Supporting Info

The purpose of this paper is to present a novel way to building quantitative structure-propertyrelationship (QSPR) models for predicting the gas-to-benzene solvation enthalpy (ΔHSolv) of 158 organiccompounds based on molecular descriptors calculated from the structure alone. Different kinds of descriptorswere calculated for each compounds using dragon package. The variable selection technique of enhancedreplacement method (ERM) was employed to select optimal subset of descriptors. Our investigation revealsthat the dependence of physico-chemical properties on solvation enthalpy is a nonlinear observable fact andthat ERM method is unable to model the solvation enthalpy accurately. The standard error value of predictionset for support vector machine (SVM) is 1.681 kJ·mol-1 while it is 4.624 kJ·mol-1 for ERM. The resultsestablished that the calculated ΔHSolv values by SVM were in good agreement with the experimental ones, andthe performances of the SVM models were superior to those obtained by ERM one. This indicates that SVMcan be used as an alternative modeling tool for QSPR studies.



关键词: Quantitative structure-property relationship   Gas-to-benzene solvation enthalpy   Descriptor   Enhanced replacement method   Support vector machine  
收稿日期 2016-12-13 修回日期 2017-01-16 网出版日期 2017-01-16
通讯作者: GOLMOHAMMADI Hassan Email: hassan.gol@gmail.com


引用文本: GOLMOHAMMADI Hassan, DASHTBOZORGI Zahra, KHOOSHECHIN Sajad. Developing a Support Vector Machine Based QSPR Model to PredictGas-to-Benzene Solvation Enthalpy of Organic Compounds[J]. 物理化学学报, 2017,33(5): 918-926.
GOLMOHAMMADI Hassan, DASHTBOZORGI Zahra, KHOOSHECHIN Sajad. Developing a Support Vector Machine Based QSPR Model to PredictGas-to-Benzene Solvation Enthalpy of Organic Compounds[J]. Acta Phys. -Chim. Sin., 2017, 33(5): 918-926.    doi: 10.3866/PKU.WHXB201701163

(1) Duffy, E. M.; Jorgensen, W. L. J. Am. Chem. Soc. 2000, 122, 2878. doi: 10.1021/ja993663t
(2) Cornell, W. E.; Cieplak, P.; Bayly, C. I.; Merz, K. M.; Ferguson, D. M.; Spellmayer, D. C.; Fox, T.; Caldwell, J.W.; Kollman, P.A. J. Am. Chem. Soc. 1995, 117, 5179. doi: 10.1021/ja00124a002
(3) Graziano, G. Can. J. Chem. 2000, 78, 1233. doi: 10.1139/v00-125
(4) Graziano, G. Biophys. Chem. 1999, 82, 69. doi: 10.1016/S0301-4622(99)00063-0
(5) Graziano, G. J. Phys. Chem. B 2000, 104, 9249. doi: 10.1021/jp001461
(6) Garde, S.; Garcia, A. E.; Pratt, L. R.; Hummer, G. Biophys.Chem. 1999, 78, 21. doi: 10.1016/S0301-4622(99)00018-6
(7) Mintz, C.; Burton, K.; Acree, W. E., Jr.; Abraham, M. H. FluidPhase Equilibr. 2007, 258, 191. doi: 10.1016/j.fluid.2007.06.016
(8) Chickos, J. S.; Acr
(9) ee, W. E., Jr. J. Phys. Chem. Ref. Data 2003, 32, 519.doi: 10.1063/1.1529214
(10) Chickos, J. S.; Acree, W. E., Jr. J. Phys. Chem. Ref. Data 2002, 31, 537. doi: 10.1063/1.1475333
(11) Borges does Santos, R. M.; Muralha, V. S. F.; Correia, C. F.; Simões, J. A. M. J. Am. Chem. Soc. 2001, 123, 12670.doi: 10.1021/ja010703w
(12) Laarhoven, L. J. J.; Mulder, P.; Wayner, D. D. M. Acc. Chem.Res. 1999, 32, 342. doi: 10.1021/ar9703443
(13) Hansch, C.; Leo, A. Exploring QSAR: Fundamentals andApplications in Chemistry and Biology, American ChemicalSociety, Washington DC, 1995. doi: 10.1021/jm950902o
(14) Bao, L.; Sun, Z. R. FEBS Lett. 2002, 521, 109. doi: 10.1016/S0014-5793(02)02835-1
(15) Belousov, A. I.; Verzakov, S. A.; Von Frese, J. Chemom. Intell.Lab. Syst. 2002, 64, 15. doi: 10.1016/S0169-7439(02)00046-1
(16) Cai, Y. D.; Liu, X. J.; Xu, X. B.; Chou, K. C. Comput. Chem.2002, 26, 293. doi: 10.1016/S0097-8485(01)00113-9
(17) Morris, C.W.; Autret, A.; Boddy, L. Ecol. Model. 2001, 146, 57.doi: 10.1016/S0304-3800(01)00296-4
(18) Song, M. H.; Breneman, C. M.; Bi, J. B.; Sukumar, N.; Bennett, K. P.; Cramer, S.; Tugcu, N. J. Chem. Inf. Comput. Sci. 2002, 42, 1347. doi: 10.1021/ci025580t
(19) Liu, H. X.; Zhang, R. S.; Luan, F.; Yao, X. J.; Liu, M. C.; Hu, Z.D.; Fan, B. T. J. Chem. Inf. Comput. Sci. 2003, 43, 900.doi: 10.1021/ci0256438
(20) Liu, H. X.; Zhang, R. S.; Yao, X. J.; Liu, M. C.; Hu, Z. D.; Fan, B. T. J. Chem. Inf. Comput. Sci. 2003, 43, 1288. doi: 10.1021/ci0340355
(21) Golmohammadi, H.; Dashtbozorgi, Z.; Acree, W. E., Jr. Struct.Chem. 2013, 24, 1799. doi: 10.1007/s11224-013-0222-4
(22) Golmohammadi, H.; Dashtbozorgi, Z.; Acree, W. E., Jr. Phys.Chem. Liq. 2013, 51, 182. doi: 10.1080/00319104.2012.708932
(23) Dashtbozorgi, Z.; Golmohammadi, H.; Acree, W. E., Jr.Thermochim. Acta 2012, 539, 7. doi: 10.1016/j.tca.2012.03.017
(24) Golmohammadi, H.; Dashtbozorgi, Z.; Acree, W. E., Jr. Mol.Inf. 2012, 31, 867. doi: 10.1002/minf.201200091
(25) Dashtbozorgi, Z.; Golmohammadi, H.; Acree, W. E., Jr. Eur. J.Pharm. Sci. 2012, 47, 421. doi: 10.1016/j.ejps.2012.06.021
(26) Mintz, C.; Clark, M.; Burton, K.; Acree, W. E., Jr.; Abraham, M.H. QSAR Comb. Sci. 2007, 26, 881. doi: 10.1002/qsar.200630152
(27) Toubaei, A.; Golmohammadi, H.; Dashtbozorgi, Z.; Acree, W.E., Jr. J. Mol. Liq. 2012, 175, 24. doi: 10.1016/j.molliq.2012.08.006
(28) Todeschini, R.; Consonni, V. Molecular Descriptors forChemoinformatics.Wiley VCH:Weinheim, 2009. doi: 10.1002/9783527628766.ch22
(29) Hyperchem, re. 4. for Windows, Autodesk, Sansalito, CA, 1995.
(30) Todeschini, R.; Consonni, V.; Pavan, M. Dragon Software, Milano, 2002.
(31) Mercader, A. G.; Duchowicz, P. R.; Fernández, F. M.; Castro, E.A. J. Chem. Inf. Model. 2011, 51, 1575. doi: 10.1021/ci200079b
(32) MATLAB 7.0, The Mathworks Inc., Natick, MA, USA, 2005, http://www.mathworks.com.
(33) Baghban, A.; Ahmadi, M. A.; Pouladi, B.; Amanna, B.J. Supercrit. Fluids 2015, 101, 184. doi: 10.1016/j.supflu.2015.03.004
(34) Vapnik, V. N.; Lerner, A. Autom. Remote Control 1963, 24, 774.
(35) Vapnik, V. N.; Chervonenkis, A. Y. Autom. Remote Control 1964, 25, 821.
(36) Rojas, C.; Duchowicz, P. R.; Tripaldi, P.; Pis Diez, R.Chemometr. Intell. Lab. Syst. 2015, 140, 126. doi: 10.1016/j.chemolab.2014.09.020
(37) Mercader, G.; Duchowicz, P. R.; Fernández, F. M.; Castro, E. A.Chemometr. Intell. Lab. Syst. 2008, 92, 138. doi: 10.1016/j.chemolab.2008.02.005
(38) Gramatica, P. QSAR Comb. Sci. 2007, 26, 694. doi: 10.1002/qsar.200610151
(39) Cao, D. S.; Liang, Y. Z.; Xu, Q. S.; Li, H. D.; Chen, X.J. Comput. Chem. 2010, 31, 592. doi: 10.1002/jcc.21351
(40) Yan, J.; Huang, J. H.; He, M.; Lu, H. B.; Yang, R.; Kong, B.; Xu, Q. S.; Liang, Y. Z. J. Sep. Sci. 2013, 36, 2464. doi: 10.1002/jssc.201300254
(41) Cao, D. S.; Liang, Y. Z.; Xu, Q. S.; Yun, Y. H.; Li, H. D.J. Comput. Aided Mol. Des. 2011, 25, 67. doi: 10.1007/s10822-010-9401-1
(42) Eriksson, L.; Jaworska, J.; Worth, A. P.; Cronin, M. T.; McDowell, R. M.; Gramatica, P. Health Perspect. 2003, 111, 1361. doi: 10.1289/ehp.5758
(43) Golbraikh, A.; Shen, M.; Xiao, Z.; Xiao, Y.; Lee, K. H.; Tropsha, A. J. Comput. Aided Mol. Des. 2003, 17, 241.doi: 10.1023/A:1025386326946
(44) Golbraikh, A.; Tropsha, A. J. Mol. Graph. Model. 2002, 20, 269.doi: 10.1016/S1093-3263(01)00123-1
(45) Agrawal, V. K.; Khadikar, P.V. Bioorg. Med. Chem. 2001, 911, 3035. doi: 10.1016/S0968-0896(01)00211-5
(46) Pourbasheer, E.; Riahi, S.; Ganjali, M. R.; Norouzi, P.J. Enzyme. Inhib. Med. Chem. 2010, 256, 844. doi: 10.3109/14756361003757893
(47) Antipin, I. S.; Arslanov, N. A.; Palyulin, V. A.; Konovalov, A. I.; Zefirov, N. S. Dokl. Akad. Nauk. SSSR 1991, 316, 925.
(48) Sarkar, R.; Roy, A. B.; Sarkar, P. K. Math. Biosci. 1978, 39, 299.doi: 10.1016/0025-5564(78)90060-3
(49) Geary, R.C. Incorp. Statist. 1954, 5, 15. doi: 10.2307/2986645
(50) Moreau, G.; Broto, P. Nouv. J. Chim. 1980, 4, 757.
(51) Todeschini, R.; Consonni, V. Handbook of MolecularDescriptors, In: Methods and Principles in MedicinalChemistry; Mannhold, R., Kubinyi, H., Timmerman, H. Eds.; Wiley-VCH:Weinheim, 2000. doi: 10.1002/9783527613106
(52) Ma, S.; Lv, M.; Deng, F.; Zhang, X.; Zhai, H.; Lv, W. J. Hazard.Mater. 2015, 283, 591. doi: 10.1016/j.jhazmat.2014.10.011

版权所有 © 2006-2016 物理化学学报编辑部
地址:北京大学化学学院 邮政编码:100871
服务热线:(010)62751724 传真:(010)62756388 Email:whxb@pku.edu.cn
^ Top