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Schultz, T.W.; Netzeva, T.I.; Roberts, D.W.; Cronin, M.T.D. Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals. Chem. Res. Toxicol. 2005, 18, 2, 330–341.

QsarDB Repository

Schultz, T.W.; Netzeva, T.I.; Roberts, D.W.; Cronin, M.T.D. Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals. Chem. Res. Toxicol. 2005, 18, 2, 330–341.

QDB archive DOI: 10.15152/QDB.14   DOWNLOAD

QsarDB content

Property pIGC50: 40-h Tetrahymena toxicity as log(1/IGC50) [log(L/mmol)]

Compounds: 82 | Models: 10 | Predictions: 10

1: Aliphatic compounds

Regression model (regression)

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Name Type n

R2

σ

Training training 82 0.015 1.046
2: α,β-unsaturated aldehydes

Regression model (regression)

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Name Type n

R2

σ

Training training 14 0.379 1.197
3: α,β-unsaturated aldehydes

Regression model (regression)

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Name Type n

R2

σ

Training training 14 0.301 1.182
4: α,β-unsaturated aldehydes

Regression model (regression)

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Name Type n

R2

σ

Training training 14 0.229 1.294
5: α,β-unsaturated ketones

Regression model (regression)

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Name Type n

R2

σ

Training training 16 0.928 0.260
6: Methacrylates

Regression model (regression)

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Name Type n

R2

σ

Training training 11 0.925 0.262
7: Vinylene-containing esters

Regression model (regression)

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Name Type n

R2

σ

Training training 15 0.814 0.247
8: Vinylene-containing esters

Regression model (regression)

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Name Type n

R2

σ

Training training 15 0.934 0.147
9: Methacrylates and vinylene-containing esters

Regression model (regression)

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Name Type n

R2

σ

Training training 26 0.885 0.252
10: Ethynylene-containing esters

Regression model (regression)

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Name Type n

R2

σ

Training training 10 0.939 0.083

Citing

When using this data, please cite the original article and this QDB archive:

  • Schultz, T. W.; Netzeva, T. I.; Roberts, D. W.; Cronin, M. T. D. Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals. Chem. Res. Toxicol. 2005, 18, 330–341. http://dx.doi.org/10.1021/tx049833j

  • Ruusmann, V. QDB archive #14. QsarDB repository, 2012. http://dx.doi.org/10.15152/QDB.14

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Title: Schultz, T.W.; Netzeva, T.I.; Roberts, D.W.; Cronin, M.T.D. Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals. Chem. Res. Toxicol. 2005, 18, 2, 330–341.
Abstract: Toxicity data for 82 aliphatic chemicals with an alpha,beta-unsaturated substructure were compiled. Toxicity was assessed in the 2-day Tetrahymena pyriformis population growth impairment assay. Toxic potency [log(IGC50(-1))] for most of these chemicals was in excess of baseline narcosis as quantified by the 1-octanol/water partition coefficient (log K(ow)). The toxicity of the alpha,beta-unsaturated aldehydes was modeled well by log K(ow) in conjunction with the sum of partial charges on the vinylene carbon atoms (Q(C4) + Q(C3)) and the energy of the lowest unoccupied molecular orbital (E(lumo)). These electronic descriptors were also successful at modeling the toxicity of alpha,beta-unsaturated ketones. The toxicity of a range of acrylates was constant within about 0.2 of a log unit. Conversely, the toxicity of methacrylates and esters containing the vinylene group varied considerably and was explained by their hydrophobicity. The comparison of the quantitative structure-activity relationship (QSAR) for the methacrylates and esters with that for non-polar narcosis showed little significant difference and hence suggested that substitution on the carbon-carbon double bond in the methacrylates and vinylene unsaturated esters does not enhance toxicity over that of baseline. Substitution on the carbon-carbon double bond in the alpha,beta-unsaturated aldehydes resulted in toxicity that was similar to that for saturated derivatives. Although an excellent hydrophobicity-dependent QSAR was developed for the esters containing ethynylene group, these compounds are considered to act as Michael-type acceptors. Attempts to combine different groups of Michael-type acceptors into a single QSAR, based on mechanistically derived descriptors, were unsuccessful. Thus, the modeling of the toxicity of the alpha,beta-unsaturated carbonyl domain is currently limited to models for narrow subdomains.
URI: http://hdl.handle.net/10967/14
http://dx.doi.org/10.15152/QDB.14
Date: 2012-05-23


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