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.

QsarDB Repository

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

QsarDB content

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

2: All esters

Regression model (regression)

Open in:QDB ExplorerQDB Predictor

NameTypen

R2

σ

Trainingtraining210.5400.542
3: All esters

Regression model (regression)

Open in:QDB ExplorerQDB Predictor

NameTypen

R2

σ

Trainingtraining210.5580.531
4: Selected esters

Regression model (regression)

Open in:QDB ExplorerQDB Predictor

NameTypen

R2

σ

Trainingtraining180.7410.311
5: Selected esters

Regression model (regression)

Open in:QDB ExplorerQDB Predictor

NameTypen

R2

σ

Trainingtraining160.8260.252

Citing

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

Metadata

Show simple item record

dc.date.accessioned2012-05-23T16:14:19Z
dc.date.available2012-05-23T16:14:19Z
dc.date.issued2012-05-23
dc.identifier.urihttp://hdl.handle.net/10967/86
dc.identifier.urihttp://dx.doi.org/10.15152/QDB.86
dc.description.abstractThe 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.publisherVillu Ruusmann
dc.rightsAttribution 4.0 International
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.titleDeWeese, 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.endpoint6. Other (Acute toxicity to ciliate protozoa)
qdb.property.speciesTetrahymena pyriformis
qdb.descriptor.applicationClogP
qdb.descriptor.applicationMOPAC 6
bibtex.entryarticle
bibtex.entry.authorDeWeese, A. D.
bibtex.entry.authorSchultz, T. W.
bibtex.entry.doi10.1002/1522-7278(2001)16:1<54::AID-TOX60>3.0.CO;2-M
bibtex.entry.journalEnviron. Toxicol.
bibtex.entry.number1
bibtex.entry.pages54–60
bibtex.entry.titleStructure-Activity Relationships for Aquatic Toxicity to Tetrahymena: Halogen-Substituted Aliphatic Esters
bibtex.entry.volume16
bibtex.entry.year2001
qdb.model.typeRegression model (regression)


Files in this item

NameDescriptionFormatSizeView
76506763.qdb.zipn/aapplication/zip7.334KbView/Open
Files associated with this item are distributed
under Creative Commons license.

This item appears in the following Collection(s)

Show simple item record