含氯苯酚类化合物结构表征与毒性预测
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摘要
将有机化合物中的不同非氢原子及非氢原子之间的关系参数化得到新的结构描述符,运用该描述符对部分含氯苯酚类化合物分子结构进行了参数化表征。采用偏最小二乘回归(PLS)方法构建了化合物结构与毒性(-lg IC50)之间的关系模型,模型的建模相关系数(R2)为0.948,"留一法"交互检验的相关系数(Q2)为0.922,标准偏差(SD)为0.184。结果表明结构描述符能较好地表征化合物分子结构特征,所建模型稳定性好、预测能力强,对于酚类化合物QSAR研究具有一定的参考价值。
New structural descriptors were obtained through parameterization of the different non-hydrogen atoms and the relationship between them in organic molecules. Then the molecular structures of some chlorinated phenolic compounds were characterized by the structural descriptors. The partial least squares regression(PLS) method was used to construct a model of relationship between the structures and toxicity(-lg IC50) of chlorinated phenolic compounds. The modeling correlation coefficient(R2) was 0.948, the "leave one out" cross validation correlation coefficient(Q2) was 0.922 and the standard deviation(SD) was 0.184, respectively. The results showed that the structural descriptors could well characterize the molecular structures of the compounds, the stability of the model was good,and the predictive power was strong. This study shows a certain reference value for QSAR study of phenolic compounds.
New structural descriptors were obtained through parameterization of the different non-hydrogen atoms and the relationship between them in organic molecules. Then the molecular structures of some chlorinated phenolic compounds were characterized by the structural descriptors. The partial least squares regression(PLS) method was used to construct a model of relationship between the structures and toxicity(-lg IC50) of chlorinated phenolic compounds. The modeling correlation coefficient(R2) was 0.948, the "leave one out" cross validation correlation coefficient(Q2) was 0.922 and the standard deviation(SD) was 0.184, respectively. The results showed that the structural descriptors could well characterize the molecular structures of the compounds, the stability of the model was good,and the predictive power was strong. This study shows a certain reference value for QSAR study of phenolic compounds.
引文
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[2]于艳军,张勇,韩伟,等.N-取代氟乙酰胺结构与急性毒性的Co MFA和Co MSIA研究[J].生态毒理学报,2015,10(2):183-189Yu Y J,Zhang Y,Han W,et al.Co MFA and Co MSIA studies of N-substitued fluoroacetamide structures with acute toxicity[J].Asian Journal of Ecotoxicology,2015,10(2):183-189(in Chinese)
[3]堵锡华,王晓辉,冯长君.1-取代-2-氨基苯并咪唑化合物毒性和热力学性质的密度泛函理论研究[J].生态毒理学报,2014,9(6):1204-1209Du X H,Wang X H,Feng C J.Density functional theory study on the toxicity and thermodynamic property of 1-replaced-2-amino benzimidazole compounds[J].Asian Journal of Ecotoxicology,2014,9(6):1204-1209(in Chinese)
[4]顾云兰,费正皓,张玉莹.氯酚化合物对发光细菌毒性的构效关系研究[J].分析科学学报,2012,28(3):333-337Gu Y L,Fei Z H,Zhang Y Y.A quantitative structure-activity relationship study on the toxicity of chlorophenols to microtox[J].Journal of Analytical Science,2012,28(3):333-337(in Chinese)
[5]仝建波,李云飞,刘淑玲,等.氯苯与氯酚类化合物毒性的预测[J].计算机与应用化学,2010,27(3):392-396Tong J B,Li Y F,Liu S L,et al.Forecast toxicity of chlorinated benzenes and chlorinated phenols[J].Chemical Research and Application,2010,27(3):392-396(in Chinese)
[6]Liao L M,Huang X,Lei G D.Structural characterization and octanol/water partition coefficient(log P)prediction for oxygen-containing organic compounds[J].Chinese Journal of Structural Chemistry,2017,36(8):1243-1250
[7]廖立敏.酚类化合物结构与醇/水分配系数(log Kow)关系研究[J].生态毒理学报,2017,12(3):709-715Liao L M.Study on the relationship between structure and alcohol/water partition coefficients(log Kow)of phenolic compounds[J].Asian Journal of Ecotoxicology,2017,12(3):709-715(in Chinese)
[8]廖立敏,李建凤,雷光东.饮用水中挥发性有机物结构与色谱保留时间的关系[J].环境化学,2017,36(4):710-715Liao L M,Li J F,Lei G D.Relationship between structure and gas chromatography retention time of volatile organic compounds in drinking water[J].Environmental Chemistry,2017,36(4):710-715(in Chinese)
[9]廖立敏,杨欢,雷光东.醛酮类化合物离子迁移谱QSSR研究[J].计算机与应用化学,2016,33(12):1319-1321Liao L M,Yang H,Lei G D.QSSR research on ion mobility spectrometry for aliphatic aldehydes and ketones[J].Computers and Applied Chemistry,2016,33(12):1319-1321(in Chinese)
[10]Ertürka M D,Sacana M T,Novicb M,et al.Quantitative structure-activity relationships(QSARs)using the novel marine algal toxicity data of phenols[J].Journal of Molecular Graphics and Modelling,2012,38:90-100
[11]王晓荣,堵锡华.mB对气相色谱保留指数的QSPR研究[J].南京工业大学学报,2002,24(3):31-37Wang X R,Du X H.The conectivity index for QSPR study of gas chromatography retention index[J].Journal of Nanjing University of Technology,2002,24(3):31-37(in Chinese)
[12]梅虎,周原,孙立力,等.氨基酸结构描述子矢量VHSE及其在肽QSAR中的应用[J].化学通报,2005,68(7):534-540Mei H,Zhou Y,Sun L L,et al.A new set of descriptors of amino acids and its application in peptide QSAR[J].Chemistry,2005,68(7):534-540(in Chinese)
[13]顾云兰,陈鑫,简美玲.苯胺类化合物结构与毒性的密度泛函理论研究[J].化学研究与应用,2015,27(8):1139-1144Gu Y L,Chen X,Jian M L.Study on the structure-toxicity relationship of aniline compounds by density functional theory[J].Chemical Research and Application,2015,27(8):1139-1144(in Chinese)
[14]Andersson P M,Sj9strom M,Lundstedt T.Preprocessing peptide sequences for multivariate sequence-property analysis[J].Chemometrics and Intelligent Laboratory Systems,1998,42:41-50