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DeWeese, A.D.; Schultz, T.W. Structure-Activity Relationships for Aquatic Toxicity to Tetrahymena: Halogen-Substituted Aliphatic Esters. Environ. Toxicol. 2001, 16, 1, 54–60.

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DeWeese, A.D.; Schultz, T.W. Structure-Activity Relationships for Aquatic Toxicity to Tetrahymena: Halogen-Substituted Aliphatic Esters. Environ. Toxicol. 2001, 16, 1, 54–60.

QDB archive DOI: 10.15152/QDB.86   DOWNLOAD

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

2: All esters

Regression model (regression)

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Name Type n

R2

σ

Training training 21 0.540 0.542
3: All esters

Regression model (regression)

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Name Type n

R2

σ

Training training 21 0.558 0.531
4: Selected esters

Regression model (regression)

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Name Type n

R2

σ

Training training 18 0.741 0.311
5: Selected esters

Regression model (regression)

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Name Type n

R2

σ

Training training 16 0.826 0.252

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dc.date.accessioned 2012-05-23T16:14:19Z
dc.date.available 2012-05-23T16:14:19Z
dc.date.issued 2012-05-23
dc.identifier.uri http://hdl.handle.net/10967/86
dc.identifier.uri http://dx.doi.org/10.15152/QDB.86
dc.description.abstract The toxicity of a series of 21 mono- and dihalogenated aliphatic monoesters has been evaluated using a Tetrahymena pyriformis population growth impairment assay. A structure-activity model has been developed for toxicity data (log(IGC50(-1))), using the 1-octanol/water partition coefficient (logKow) and the energy of the lowest unoccupied molecular orbital (ELUMO) as descriptors. A statistically robust plane (log of the inverse of the 50% growth inhibitory concentration (IGC50(-1)) = 0.34 logKow - 0.84 (ELUMO) + 0.04; n = 15, r2 = 0.85, s = 0.26, F = 33, Pr > F = 0.0001) was found for monohalogen-substituted derivatives. These substances are thought to exhibit toxicity via the soft electrophilic mode of toxic action. This toxicity is imparted by the leaving ability of the halogen, which is enhanced when it is placed in close proximity to the carbonyl group. This leaving ability allows haloesters, especially alpha-haloesters, to undergo an SN2, addition-elimination substitution electro(nucleo)philic reaction. Outliers to the above model broadly fell into two groups: small reactive molecules (e.g., propylbromoacetate) that were more toxic than predicted and molecules in which the reactive center was sterically hindered by an alkyl group (e.g., ethyl-2-bromoisovalerate), which were less toxic than predicted.
dc.publisher Villu Ruusmann
dc.rights Attribution 4.0 International
dc.rights.uri http://creativecommons.org/licenses/by/4.0/
dc.title DeWeese, A.D.; Schultz, T.W. Structure-Activity Relationships for Aquatic Toxicity to Tetrahymena: Halogen-Substituted Aliphatic Esters. Environ. Toxicol. 2001, 16, 1, 54–60.
qdb.property.endpoint 6. Other (Acute toxicity to ciliate protozoa)
qdb.property.species Tetrahymena pyriformis
qdb.descriptor.application ClogP
qdb.descriptor.application MOPAC 6
bibtex.entry article
bibtex.entry.author DeWeese, A. D.
bibtex.entry.author Schultz, T. W.
bibtex.entry.doi 10.1002/1522-7278(2001)16:1<54::AID-TOX60>3.0.CO;2-M
bibtex.entry.journal Environ. Toxicol.
bibtex.entry.number 1
bibtex.entry.pages 54–60
bibtex.entry.title Structure-Activity Relationships for Aquatic Toxicity to Tetrahymena: Halogen-Substituted Aliphatic Esters
bibtex.entry.volume 16
bibtex.entry.year 2001
qdb.model.type Regression model (regression)


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