Developing the QSPR model for predicting the storage lipid/water distribution coefficient of organic compounds
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RESEARCH ARTICLE
Developing the QSPR model for predicting the storage lipid/water distribution coefficient of organic compounds Miao Li , Jian Li , Yuchen Lu, Cenyang Han, Xiaoxuan Wei, Guangcai Ma, Haiying Yu (✉) #
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College of Geography and Environmental Sciences, Zhejiang Normal University, Jinhua 321004, China
HIGHLIGHTS
GRAPHIC ABSTRACT
• A predictive model for storage lipid/water distribution coefficient was developed. • The model yields outstanding fitting performance, robustness, and predictive ability. • Hydrophobic and electrostatic interactions and molecular size dominate log Klip/w. • The model can be used in a wide application domain to predict log Klip/w values.
ARTICLE INFO Article history:
Received 18 April 2020 Revised 8 July 2020 Accepted 14 July 2020 Available online 30 August 2020 Keywords: Storage lipid/water distribution coefficient log Klip/w Organic compounds QSPR Quantum chemical descriptors
ABSTRACT The distribution of organic compounds in stored lipids affects their migration, transformation, bioaccumulation, and toxicity in organisms. The storage lipid/water distribution coefficient (log Klip/w) of organic chemicals, which quantitatively determines such distribution, has become a key parameter to assist their ecological security and health risk. Due to the impossibility to measure Klip/w values for a huge amount of chemicals, it is necessary to develop predictive approaches. In this work, a quantitative structure-property relationship (QSPR) model for estimating log Klip/w values of small organic compounds was constructed based on 305 experimental log Klip/w values. Quantum chemical descriptors and n-octanol/water partitioning coefficient were employed to characterize the intermolecular interactions that dominate log Klip/w values. The hydrophobic and electrostatic interactions and molecular size have been found to play important roles in governing the distribution of chemicals between lipids and aqueous phases. The regression (R2 = 0.959) and validation (Q2 = 0.960) results indicate good fitting performance and robustness of the developed model. A comparison with the predictive performance of other commercial software further proves the higher accuracy and stronger predictive ability of the developed Klip/w predictive model. Thus, it can be used to predict the Klip/w values of cycloalkanes, long-chain alkanes, halides (with fluorine, chlorine, and bromine as substituents), esters (without phosphate groups), alcohols (without methoxy groups), and aromatic compounds. © Higher Education Press 2020
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Introduction
Organic chemicals in environmental media can enter living organisms through the adsorption in lipids (van Wezel et al., 1995; Endo et al., 2013; Hu et al., 2020; Yi et al.,
✉ Corresponding author E-mail: [email protected] #
These authors contributed equally to this work.
2020). The accumulation in lipids may subsequently affect their toxicity. Such as the lipophilic organics phenanthrene and anthracene have been found to be enriched in lipids through distribution, and then distrib
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