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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.

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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.

QDB archive DOI: 10.15152/QDB.14   DOWNLOAD

QsarDB content

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

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 QDB archive, please cite (see details) it together with the original article:

  • Ruusmann, V. Data for: Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals. QsarDB repository, QDB.14. 2012. http://dx.doi.org/10.15152/QDB.14

  • 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

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dc.date.accessioned 2012-05-23T15:33:56Z
dc.date.available 2012-05-23T15:33:56Z
dc.date.issued 2012-05-23
dc.identifier.uri http://hdl.handle.net/10967/14
dc.identifier.uri http://dx.doi.org/10.15152/QDB.14
dc.description.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.
dc.publisher Villu Ruusmann
dc.rights Attribution 4.0 International
dc.rights.uri http://creativecommons.org/licenses/by/4.0/
dc.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.
qdb.property.endpoint 6. Other (Acute toxicity to ciliate protozoa)
qdb.property.species Tetrahymena pyriformis
qdb.descriptor.application ClogP 1.0.0
qdb.descriptor.application TSAR 3.3
bibtex.entry article
bibtex.entry.author Schultz, T. W.
bibtex.entry.author Netzeva, T. I.
bibtex.entry.author Roberts, D. W.
bibtex.entry.author Cronin, M. T. D.
bibtex.entry.doi 10.1021/tx049833j
bibtex.entry.journal Chem. Res. Toxicol.
bibtex.entry.number 2
bibtex.entry.pages 330–341
bibtex.entry.title Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals
bibtex.entry.volume 18
bibtex.entry.year 2005
qdb.model.type Regression model (regression)


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