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Akers, K.S.; Sinks, G.D.; Schultz, T.W. Structure-toxicity relationships for selected halogenated aliphatic chemicals. Environ. Toxicol. Pharmacol. 1999, 7, 1, 33–39.

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Akers, K.S.; Sinks, G.D.; Schultz, T.W. Structure-toxicity relationships for selected halogenated aliphatic chemicals. Environ. Toxicol. Pharmacol. 1999, 7, 1, 33–39.

QDB archive DOI: 10.15152/QDB.38   DOWNLOAD

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

Compounds: 39 | Models: 2 | Predictions: 2

6: All compounds

Regression model (regression)

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Name Type n

R2

σ

Training training 39 0.681 0.620
7: Selected compounds

Regression model (regression)

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Name Type n

R2

σ

Training training 34 0.776 0.501

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Title: Akers, K.S.; Sinks, G.D.; Schultz, T.W. Structure-toxicity relationships for selected halogenated aliphatic chemicals. Environ. Toxicol. Pharmacol. 1999, 7, 1, 33–39.
Abstract: Toxicity to the ciliate Tetrahymena pyriformis (log(IGC(50)(-1))) for 39 halogen-substituted alkanes, alkanols, and alkanitriles were obtained experimentally. Log(IGC(50)(-1)) along with the hydrophobic term, logK(ow) (1-octanol/water partition coefficient) and the electrophilic parameter, E(lumo) (the energy of the lowest unoccupied molecular orbital) were used to develop quantitative structure-activity relationships (QSARs). Two strong hydrophobic dependent relationships were obtained: one for the haloalkanes and a second for the haloalcohols. The relationship for the haloalkanes [log(IGC(50)(-1))=0.92 (logK(ow))-2.58; n=4, r(2)=0.993, s=0.063, f=276, Pr>f=0.0036] was not different from baseline toxicity. With the rejection of 1,3-dibromo-2-propanol as a statistical outlier, the relationship [log(IGC(50)(-1))=0.63(logK(ow))-1.18; n=19, r(2)=0.860, s=0.274, f=104, Pr>f=0.0001] was observed for the haloalcohols. No hydrophobicity-dependent model (r(2)=0.165) was observed for the halonitriles. However, an electrophilicity-dependent model [log(IGC(50)(-1))=-1.245(E(lumo))+0.73; n=15, r(2)=0.588, s=0.764, F=18.6, Pr>f=0.0009] was developed for the halonitriles. Additional analysis designed to examine surface-response modeling of all three chemical classes met with some success. Following rejection of statistical outliers, the plane [log(IGC(50)(-1))=0.60(logK(ow))-0.747(E(lumo))-0.37; n=34, r(2)=0.915, s=0.297, F=162, Pr>F=0.0001] was developed. The halogenated alcohols and nitriles tested all had observed toxicity in excess of non-reactive baseline toxicity (non-polar narcosis). This observation along with the complexity of the structure-toxicity relationships developed in this study suggests that the toxicity of haloalcohols and halonitriles is by multiple and/or mixed mechanisms of action which are electro(nucleo)philic in character.
URI: http://hdl.handle.net/10967/38
http://dx.doi.org/10.15152/QDB.38
Date: 2012-05-23


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