Quantitative structure–property relationships (QSPR) for steroidal compounds of environmental importance

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Title Quantitative structure–property relationships (QSPR) for steroidal compounds of environmental importance
Author Cao, Qiming; Garib, Vernon; Yu, Jimmy; Connell, Des; Campitelli, Marc Ronald
Journal Name Chemosphere
Year Published 2009
Place of publication Oxford, UK
Publisher Pergamon Press
Abstract A quantitative structure–property relationships (QSPR) study was carried out for 17 steroidal compounds using calculated molecular descriptors and measured properties. The utility of calculated molecular descriptors and properties was evaluated and improved in some instances by subgroup classification of these 17 compounds into estrogens and androgens. The calculated values for the octanol–water partition coefficient (log Kow) were found to be in good agreement with the measured values for all 17 compounds, whilst good agreement between the calculated and measured values for aqueous solubility (log S) was found only for the subgroup of androgens. Good linear relationships (R2P0.782) were found between measured log Kow values and three molecular descriptors (log FOSA, hydrophobic component of the total solvent accessible surface area; log FISA, hydrophilic component of the total solvent accessible area and log PSA, Van de Waals surface area of polar nitrogen and oxygen atoms). For the measured log S values, only weak correlations with molecular descriptors were observed (R2P0.505). The coefficient of log S in the relationship with the hydrophobic parameter (log FOSA) was negative but positive with the hydrophilic parameters (log FISA and log PSA). Conversely with log Kow the opposite was found. These observations are in accord with the effects of molecular polarity on aqueous solubility.
Peer Reviewed Yes
Published Yes
Alternative URI http://dx.doi.org/10.1016/j.chemosphere.2009.03.045
Volume 76
Page from 453
Page to 459
ISSN 0045-6535
Date Accessioned 2009-07-29
Language en_AU
Faculty Faculty of Science, Environment, Engineering and Technology
Subject Environmental Chemistry (incl Atmospheric Chemistry)
URI http://hdl.handle.net/10072/28606
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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