A procedure that makes it possible to generate a coherent model for prediction of the octanol-water partition coefficient within the molecular connectivity formalism was put forward. The method is based on the optimization of weights for corresponding skeletal atoms and is similar to the method for calculation of a variable connectivity index proposed by Randić. In contrast to Randić's method, we incorporate in the algorithm the possibility that the contribution of a term describing a carbon-heteroatom bond may be negative. When tested on a set of about 300 structurally diverse organic molecules, our procedure proved to be superior to the standard valence connectivity method. External validation on a smaller set of compounds confirmed the superiority of our procedure with respect to the standard one. Intramolecular interactions, which are operative in more complex compounds, are treated in a similar fashion to that in the Hansch-Leo or Rekker methods, by inclusion of empirical correction factors.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ci050024v | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Anticancer diiron aminocarbyne complexes with labile N-donor ligands.
Eur J Med Chem
January 2025
University of Pisa, Department of Chemistry and Industrial Chemistry, Via G. Moruzzi 13, I-56124, Pisa, Italy. Electronic address:
The novel diiron amine complexes [FeCp(CO)(NHR')(μ-CO){μ-CN(Me)(Cy)}]CFSO [R' = H, 3; Cy, 4; CHCHNH, 5; CHCHNMe, 6; CHCH(4-CHOMe), 7; CHCH(4-CHOH), 8; Cp = η-CH, Cy = CH = cyclohexyl] were synthesized in 49-92 % yields from [FeCp(CO)(μ-CO){μ-CN(Me)(Cy)}]CFSO, 1a, using a straightforward two-step procedure. They were characterized by IR and multinuclear NMR spectroscopy, and the structure of 7 was confirmed through X-ray diffraction analysis. Complexes 3-8 and the acetonitrile adducts [FeCp(CO)(NCMe)(μ-CO){μ-CN(Me)(R)}]CFSO (R = Cy, 2a; Me, 2b; Xyl = 2,6-CHMe, 2c) were assessed for their water solubility, octanol-water partition coefficient and stability in physiological-like solutions.
View Article and Find Full Text PDFLipophilicity and blood partitioning are important determinants for predicting toxicokinetics using physiologically-based toxicokinetic (PBTK) modeling. In this study, the logarithm of the -octanol:water partition coefficient (log) and the blood-to-plasma concentration ratio ( ) were for the first time experimentally determined for the pyrrolizidine alkaloids (PAs) intermedine, lasiocarpine, monocrotaline, retrorsine and their -oxides (PANOs). Validated assays for log (miniaturized shake-flask method) and (LC-MS/MS-based depletion assay) determination were compared to an ensemble of models.
View Article and Find Full Text PDFQuantum chemically calculated abraham parameters for quantifying and predicting polymer hydrophobicity.
Environ Toxicol Chem
January 2025
Environmental Science Division, Argonne National Laboratory, Lemont, IL, 60439, USA.
The leakage and accumulation of plastic in the environment is a significant and growing problem with numerous detrimental impacts and has led to a push toward the design and development of more environmentally benign materials. To this end we have developed a quantum chemistry (QC) based model for predicting the mobility of polymer materials from molecular structure. Hydrophobicity is used as a surrogate for mobility given that hydrophobic interactions drive much of the partitioning of contaminants in and out of various environmentally relevant compartments.
View Article and Find Full Text PDFDistribution and bioconcentration of semivolatile organic compounds (SVOCs) in soils and vascular plant Colobanthus quitensis from Sub-Antarctic and Antarctic regions.
Sci Total Environ
February 2025
Centro de Genómica, Ecología y Medio Ambiente (GEMA), Universidad Mayor, Campus Huechuraba, Santiago, Chile; Institute of Environment, Florida International University, University Park, Miami, FL 33199, USA; Data Observatory Foundation, Santiago, Chile. Electronic address:
Semi-volatile organic compounds (SVOCs) are widely distributed across the globe, including polar regions. This study investigates the distribution and bioconcentration of organochlorine pesticides (OCPs), polychlorinated biphenyls (PCBs), and polycyclic aromatic hydrocarbons (PAHs) in soils and Colobanthus quitensis, while also estimating potential emission sources. Results indicated high concentrations of PAHs in soils and plants from the Sub-Antarctic region, while OCPs and PCBs were more prevalent in the Antarctic region, with higher contaminant concentrations found in soils than in plant tissues.
View Article and Find Full Text PDFDevelopment of quantitative structure property relationship models and tool for predicting the soil adsorption coefficient (logK).
Environ Pollut
January 2025
School of Environmental and Biological Engineering, Nanjing University of Science and Technology, Nanjing, 210094, China. Electronic address:
The soils/sediments organic carbon sorption coefficient (K) of organic substances is one of the indispensable environmental behavioral parameters in chemicals management. Because the test procedure used to measure K is normally expensive and time-consuming, predictive methods are considered vitally important technology to fill the data gap of K. In this study, quantitative structure-property relationship (QSPR) models are developed using a data set with 1477 experimental logK values and seven typical machine learning algorithms.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!