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Structure Database (LMSD)

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Common Name

11-HETE

Systematic Name

11-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoic acid

Synonyms

LM ID

LMFA03060085

Formula

C₂₀H₃₂O₃

Exact Mass

Calculate m/z

320.235145

Sum Composition

FA 20:4;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

(±)11-HETE is an oxylipin formed non-enzymatically from arachidonic acid .^1,2 Levels of (±)11-HETE are increased in an in vitro model of lipid peroxidation induced by ferrous ammonium sulfate (FAS) in rat brain homogenates.³ Levels are also increased in rat liver in an in vivo model of lipid peroxidation induced by carbon tetrachloride (CCl4). It has been found in skin extracts from individuals with psoriasis and in atherosclerotic plaques.^4,5

This information has been provided by Cayman Chemical

References

1. Waddington, E., Sienuarine, K., Puddey, I., et al. Identification and quantitation of unique fatty acid oxidation products in human atherosclerotic plaque using high-performance liquid chromatography. Anal. Biochem. 292(2), 234-244 (2001).

2. Camp, R.D.R., Mallet, A.I., Woollard, P.M., et al. The identification of hydroxy fatty acids in psoriatic skin. Prostaglandins 26(3), 431-447 (1983).

3. Derogis, P.B.M.C., Chaves-Filho, A.B., and Miyamoto, S. Characterization of hydroxy and hydroperoxy polyunsaturated fatty acids by mass spectrometry. Bioactive lipids in health and disease 21-38 (2019).

4. Powell, W.S., and Rokach, J. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. Biochim. Biophys. Acta 1851(4), 340-355 (2014).

5. Guido, D.M., McKenna, R., and Mathews, W.R. Quantitation of hydroperoxy-eicosatetraenoic acids and hydroxy-eicosatetraenoic acids as indicators of lipid peroxidation using gas chromatography-mass spectrometry. Anal. Biochem. 209(1), 123-129 (1993).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

GCZRCCHPLVMMJE-RLZWZWKOSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b9-6-,10-7-,14-11-,16-13+

SMILES (Click to copy)

C(O)(=O)CCC/C=C\C/C=C\CC(O)/C=C/C=C\CCCCC