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Prediction of the Fate of Organic Compounds in the Environment From Their Molecular Properties: A Review.

Mamy L, Patureau D, Barriuso E, Bedos C, Bessac F, Louchart X, Martin-Laurent F, Miege C, Benoit P - Crit Rev Environ Sci Technol (2015)

Bottom Line: Among the 686 molecular descriptors, five were found to be dominant in the 790 collected equations and the most generic ones: four quantum-chemical descriptors, the energy of the highest occupied molecular orbital (EHOMO) and the energy of the lowest unoccupied molecular orbital (ELUMO), polarizability (α) and dipole moment (μ), and one constitutional descriptor, the molecular weight.Keeping in mind that the combination of descriptors belonging to different categories (constitutional, topological, quantum-chemical) led to improve QSAR performances, these descriptors should be considered for the development of new QSAR, for further predictions of environmental parameters.This review also allows finding of the relevant QSAR equations to predict the fate of a wide diversity of compounds in the environment.

View Article: PubMed Central - PubMed

Affiliation: INRA-AgroParisTech, UMR 1402 ECOSYS (Ecologie Fonctionnelle et Ecotoxicologie des Agroécosystèmes) , Versailles , France.

ABSTRACT

A comprehensive review of quantitative structure-activity relationships (QSAR) allowing the prediction of the fate of organic compounds in the environment from their molecular properties was done. The considered processes were water dissolution, dissociation, volatilization, retention on soils and sediments (mainly adsorption and desorption), degradation (biotic and abiotic), and absorption by plants. A total of 790 equations involving 686 structural molecular descriptors are reported to estimate 90 environmental parameters related to these processes. A significant number of equations was found for dissociation process (pKa), water dissolution or hydrophobic behavior (especially through the KOW parameter), adsorption to soils and biodegradation. A lack of QSAR was observed to estimate desorption or potential of transfer to water. Among the 686 molecular descriptors, five were found to be dominant in the 790 collected equations and the most generic ones: four quantum-chemical descriptors, the energy of the highest occupied molecular orbital (EHOMO) and the energy of the lowest unoccupied molecular orbital (ELUMO), polarizability (α) and dipole moment (μ), and one constitutional descriptor, the molecular weight. Keeping in mind that the combination of descriptors belonging to different categories (constitutional, topological, quantum-chemical) led to improve QSAR performances, these descriptors should be considered for the development of new QSAR, for further predictions of environmental parameters. This review also allows finding of the relevant QSAR equations to predict the fate of a wide diversity of compounds in the environment.

No MeSH data available.


Related in: MedlinePlus

Molecular descriptors that are the most frequently used to assess the parameters related to the main processes governing the fate of organic compounds in the environment (see Tables S1 and S2).
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f0002: Molecular descriptors that are the most frequently used to assess the parameters related to the main processes governing the fate of organic compounds in the environment (see Tables S1 and S2).

Mentions: The descriptors that were the most used in the 790 equations are summarized in Figure 2. Twenty-two descriptors were involved in more than 10 equations: nine were quantum-chemical descriptors related to the energies (CCR, EE, EHOMO, ELUMO, q−, QH+, TE, α, μ), eight were topological and they were all MCI (0χ, 0χv, 1χ, 1χv, 2χ, 2χv, 3χv, 3χvc), three were geometric related to the surface and the volume of the compounds (TSA, VdW, Vm), and two were constitutional (MW and nCl). The most used descriptor is EHOMO, which is involved in 80 (i.e., 10%) equations, followed by α in 68 (i.e., 8.6%) equations, ELUMO in 58 (i.e., 7.3%) equations, MW in 57 (i.e., 7.2%) equations, μ in 46 (i.e., 5.8%) equations, and 1χv in 44 (i.e., 5.6%) equations. The nCl, VdW, Vm, TSA, 0χ, 0χv, 1χ, 2χ, 2χv, 3χv, 3χvc, CCR, EE, q−, QH+, and TE descriptors were included in 11–41 (i.e., 1.4 to 5.4%) equations (Figure 2). The remaining descriptors of Table S1 were mainly found only in one or two equations.Figure 2 Molecular descriptors that are the most frequently used to assess the parameters related to the main processes governing the fate of organic compounds in the environment (see Tables S1 and S2).


Prediction of the Fate of Organic Compounds in the Environment From Their Molecular Properties: A Review.

Mamy L, Patureau D, Barriuso E, Bedos C, Bessac F, Louchart X, Martin-Laurent F, Miege C, Benoit P - Crit Rev Environ Sci Technol (2015)

Molecular descriptors that are the most frequently used to assess the parameters related to the main processes governing the fate of organic compounds in the environment (see Tables S1 and S2).
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4376206&req=5

f0002: Molecular descriptors that are the most frequently used to assess the parameters related to the main processes governing the fate of organic compounds in the environment (see Tables S1 and S2).
Mentions: The descriptors that were the most used in the 790 equations are summarized in Figure 2. Twenty-two descriptors were involved in more than 10 equations: nine were quantum-chemical descriptors related to the energies (CCR, EE, EHOMO, ELUMO, q−, QH+, TE, α, μ), eight were topological and they were all MCI (0χ, 0χv, 1χ, 1χv, 2χ, 2χv, 3χv, 3χvc), three were geometric related to the surface and the volume of the compounds (TSA, VdW, Vm), and two were constitutional (MW and nCl). The most used descriptor is EHOMO, which is involved in 80 (i.e., 10%) equations, followed by α in 68 (i.e., 8.6%) equations, ELUMO in 58 (i.e., 7.3%) equations, MW in 57 (i.e., 7.2%) equations, μ in 46 (i.e., 5.8%) equations, and 1χv in 44 (i.e., 5.6%) equations. The nCl, VdW, Vm, TSA, 0χ, 0χv, 1χ, 2χ, 2χv, 3χv, 3χvc, CCR, EE, q−, QH+, and TE descriptors were included in 11–41 (i.e., 1.4 to 5.4%) equations (Figure 2). The remaining descriptors of Table S1 were mainly found only in one or two equations.Figure 2 Molecular descriptors that are the most frequently used to assess the parameters related to the main processes governing the fate of organic compounds in the environment (see Tables S1 and S2).

Bottom Line: Among the 686 molecular descriptors, five were found to be dominant in the 790 collected equations and the most generic ones: four quantum-chemical descriptors, the energy of the highest occupied molecular orbital (EHOMO) and the energy of the lowest unoccupied molecular orbital (ELUMO), polarizability (α) and dipole moment (μ), and one constitutional descriptor, the molecular weight.Keeping in mind that the combination of descriptors belonging to different categories (constitutional, topological, quantum-chemical) led to improve QSAR performances, these descriptors should be considered for the development of new QSAR, for further predictions of environmental parameters.This review also allows finding of the relevant QSAR equations to predict the fate of a wide diversity of compounds in the environment.

View Article: PubMed Central - PubMed

Affiliation: INRA-AgroParisTech, UMR 1402 ECOSYS (Ecologie Fonctionnelle et Ecotoxicologie des Agroécosystèmes) , Versailles , France.

ABSTRACT

A comprehensive review of quantitative structure-activity relationships (QSAR) allowing the prediction of the fate of organic compounds in the environment from their molecular properties was done. The considered processes were water dissolution, dissociation, volatilization, retention on soils and sediments (mainly adsorption and desorption), degradation (biotic and abiotic), and absorption by plants. A total of 790 equations involving 686 structural molecular descriptors are reported to estimate 90 environmental parameters related to these processes. A significant number of equations was found for dissociation process (pKa), water dissolution or hydrophobic behavior (especially through the KOW parameter), adsorption to soils and biodegradation. A lack of QSAR was observed to estimate desorption or potential of transfer to water. Among the 686 molecular descriptors, five were found to be dominant in the 790 collected equations and the most generic ones: four quantum-chemical descriptors, the energy of the highest occupied molecular orbital (EHOMO) and the energy of the lowest unoccupied molecular orbital (ELUMO), polarizability (α) and dipole moment (μ), and one constitutional descriptor, the molecular weight. Keeping in mind that the combination of descriptors belonging to different categories (constitutional, topological, quantum-chemical) led to improve QSAR performances, these descriptors should be considered for the development of new QSAR, for further predictions of environmental parameters. This review also allows finding of the relevant QSAR equations to predict the fate of a wide diversity of compounds in the environment.

No MeSH data available.


Related in: MedlinePlus