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Exploring the role of octanol-water partition coefficient and Henry’s law constant in predicting the lipid-water partition coefficients of organic chemicals
Partition coefficients for storage lipid-water (logK(lw)) and phospholipid-water (logK(pw)) phases are key parameters to understand the bioaccumulation and toxicity of organic contaminants. However, the published experimental databases of these properties are dwarfs and current estimation approaches...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9440013/ https://www.ncbi.nlm.nih.gov/pubmed/36056200 http://dx.doi.org/10.1038/s41598-022-19452-6 |
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author | Khawar, Muhammad Irfan Mahmood, Azhar Nabi, Deedar |
author_facet | Khawar, Muhammad Irfan Mahmood, Azhar Nabi, Deedar |
author_sort | Khawar, Muhammad Irfan |
collection | PubMed |
description | Partition coefficients for storage lipid-water (logK(lw)) and phospholipid-water (logK(pw)) phases are key parameters to understand the bioaccumulation and toxicity of organic contaminants. However, the published experimental databases of these properties are dwarfs and current estimation approaches are cumbersome. Here, we present partition models that exploit the correlations of logK(lw), and of logK(pw) with the linear combinations of the octanol-water partition coefficient (logK(ow)) and the dimensionless Henry’s law constant (air–water partition coefficient, logK(aw)). The calibrated partition models successfully describe the variations in logK(lw) data (n = 305, R(2) = 0.971, root-mean-square-error (rmse) = 0.375), and in logK(pw) data (n = 131, R(2) = 0.953, rmse = 0.413). With the inputs of logK(ow) and logK(aw) estimated from the U.S. EPA’s EPI Suite, our models of logK(lw) and logK(pw) have exhibited rmse = 0.52 with respect to experimental values indicating suitability of these models for inclusion in the EPI Suite. Our models perform similar to or better than the previously reported models such as one parameter partition models, Abraham solvation models, and models based on quantum-chemical calculations. Taken together, our models are robust, easy-to-use, and provide insight into variations of logK(lw) and logK(pw) in terms of hydrophobicity and volatility trait of chemicals. |
format | Online Article Text |
id | pubmed-9440013 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-94400132022-09-04 Exploring the role of octanol-water partition coefficient and Henry’s law constant in predicting the lipid-water partition coefficients of organic chemicals Khawar, Muhammad Irfan Mahmood, Azhar Nabi, Deedar Sci Rep Article Partition coefficients for storage lipid-water (logK(lw)) and phospholipid-water (logK(pw)) phases are key parameters to understand the bioaccumulation and toxicity of organic contaminants. However, the published experimental databases of these properties are dwarfs and current estimation approaches are cumbersome. Here, we present partition models that exploit the correlations of logK(lw), and of logK(pw) with the linear combinations of the octanol-water partition coefficient (logK(ow)) and the dimensionless Henry’s law constant (air–water partition coefficient, logK(aw)). The calibrated partition models successfully describe the variations in logK(lw) data (n = 305, R(2) = 0.971, root-mean-square-error (rmse) = 0.375), and in logK(pw) data (n = 131, R(2) = 0.953, rmse = 0.413). With the inputs of logK(ow) and logK(aw) estimated from the U.S. EPA’s EPI Suite, our models of logK(lw) and logK(pw) have exhibited rmse = 0.52 with respect to experimental values indicating suitability of these models for inclusion in the EPI Suite. Our models perform similar to or better than the previously reported models such as one parameter partition models, Abraham solvation models, and models based on quantum-chemical calculations. Taken together, our models are robust, easy-to-use, and provide insight into variations of logK(lw) and logK(pw) in terms of hydrophobicity and volatility trait of chemicals. Nature Publishing Group UK 2022-09-02 /pmc/articles/PMC9440013/ /pubmed/36056200 http://dx.doi.org/10.1038/s41598-022-19452-6 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Khawar, Muhammad Irfan Mahmood, Azhar Nabi, Deedar Exploring the role of octanol-water partition coefficient and Henry’s law constant in predicting the lipid-water partition coefficients of organic chemicals |
title | Exploring the role of octanol-water partition coefficient and Henry’s law constant in predicting the lipid-water partition coefficients of organic chemicals |
title_full | Exploring the role of octanol-water partition coefficient and Henry’s law constant in predicting the lipid-water partition coefficients of organic chemicals |
title_fullStr | Exploring the role of octanol-water partition coefficient and Henry’s law constant in predicting the lipid-water partition coefficients of organic chemicals |
title_full_unstemmed | Exploring the role of octanol-water partition coefficient and Henry’s law constant in predicting the lipid-water partition coefficients of organic chemicals |
title_short | Exploring the role of octanol-water partition coefficient and Henry’s law constant in predicting the lipid-water partition coefficients of organic chemicals |
title_sort | exploring the role of octanol-water partition coefficient and henry’s law constant in predicting the lipid-water partition coefficients of organic chemicals |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9440013/ https://www.ncbi.nlm.nih.gov/pubmed/36056200 http://dx.doi.org/10.1038/s41598-022-19452-6 |
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