Modeling the Octanol-Water Partition Coefficient of Substituted Phenols: the Use of Structure Information
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CONTRIBUTORS:
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CONFERENCE TITLE:
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CONF. LOCATION:
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None
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YEAR:
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2006
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PUB TYPE:
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Conference Paper
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SUBJECT(S):
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chemistry - computational; chemistry - organic; chemistry - physical; informatics - applied; mathematics - statistics; medicine - informatics; research - evaluation
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DISCIPLINE:
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Chemistry
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HTTP:
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http://lori.academicdirect.org/works/?id=87
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LANGUAGE:
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English
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PUB ID:
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103-436-057
(Last edited on
2007/07/08 07:16:12 GMT-6)
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SPONSOR(S):
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ABSTRACT:
Aim: The paper presents the abilities in estimation and prediction of octanol-water partition coefficient of some para-substituted phenols through integration of complex structure information by the use of an original molecular descriptors family on structure-property relationships.
Material and Method: The measured octanol-water partition coefficient of thirty para-substituted phenols, express in logarithmical scale was taken from a previous study [T.W. Schultz, Relative toxicity of para-substituted phenols: Log KOW and pKa-dependent structure-activity relationships. Bull. Environ. Contam. Toxicol., 1987, 38, 994-9]. All para-substituted phenols were used in order to generate and calculate the molecular descriptors family [L. Jäntschi, Molecular Descriptors Family on Structure Activity Relationships 1. The review of Methodology, Leonardo Electronic Journal of Practices and Technologies, 2005, 6, 76-98]. Based on the generated descriptors, the structure-property relationships models were build. The obtained models (bi-, and four-varied) were validated through the assessment of the cross-validation leave-one-out score, and analyzed through the squared correlation coefficient and the model stability. The comparison between the bi and four-varied models was performed by applying the Steiger’s Z test.
Results: The characteristics of the bi-varied model are: the squared correlation coefficient (r2) equal with 0.8943, the leave-one-out scores (r2cv-loo) equal with 0.8659, and the model stability (r2- r2cv-loo) equal with 0.02838. The multiple linear regression analysis shows that best results are obtained in four-varied model (Ŷ= 8.69∙10-2+5.56∙10-3∙isDDkGg-0.42∙IMmrKQg+9.41∙10-3∙lPMDKQg-7.8∙10-2∙lFMMKQg): r2 = 0.9781, proving to be a stable model (r2cv-loo = 0.01) and having best prediction ability (r2cv-loo= 0.9680). The correlation coefficient obtained by the four-varied model is statistically significant higher comparing with the correlation coefficient obtained by the bi-varied model (Steiger’s Z parameter = 4.3501, p-value = 6.81∙10-6).
Conclusion: The four-varied model indicates that the octanol-water partition coefficient of studied para-substituted phenols is like to be of geometry nature, is strongly dependent on the partial change of compounds and group electronegativity and it is in relation with elastic force.
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