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Structure Database (LMSD)

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Common Name

12-HETE

Systematic Name

12-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid

Synonyms

LM ID

LMFA03060088

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

Classification

Biological Context

(±)12-HETE is a racemic mixture of the arachidonic acid metabolites 12(R)-HETE and 12(S)-HETE . It is formed via non-enzymatic oxidation of arachidonic acid .^1,2 12(S)- and 12(R)-HETE are formed by 12S- and 12R-lipoxygenase-mediated oxidation of arachidonic acid, respectively.^3,4,5 12(R)-HETE can also be formed by oxidation of arachidonic acid mediated by cytochrome P450 (CYP450) enzymes.¹ (±)12-HETE (1 µM) induces aggregation of isolated human neutrophils.⁶ Production of (±)12-HETE by platelets isolated from spontaneously hypertensive rats is increased compared with platelets isolated from normotensive rats.⁷

This information has been provided by Cayman Chemical

References

1. Kühn, H., Banthiya, S., and van Leyen, K. Mammalian lipoxygenases and their biological relevance. Biochim. Biophys. Acta 1851(4), 308-330 (2015).

2. Bürger, F., Krieg, P., Marks, F., et al. Positional- and stereo-selectivity of fatty acid oxygenation catalysed by mouse (12S)-lipoxygenase isoenzymes. Biochem J. 348(Pt 2), 329-335 (2000).

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. Stern, N., Kisch, E.S., and Knoll, E. Platelet lipoxygenase in spontaneously hypertensive rats. Hypertension 27, 1149-1152 (1996).

6. O'Flaherty, J.T., Thomas, M.J., Lees, C.J., et al. Neutrophil-aggregating activity of monohydroxyeicosatetraenoic acids. Am. J. Pathol. 104, 55-62 (1981).

7. Hawkins, D.J., and Brash, A.R. Eggs of the sea urchin, Strongylocentrotus purpuratus, contain a prominent (11R) and (12R) lipoxygenase activity. J. Biol. Chem. 262(16), 7629-7634 (1987).

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)

ZNHVWPKMFKADKW-VXBMJZGYSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+

SMILES (Click to copy)

C(/CCCC(=O)O)=C/C/C=C\C=C\C(O)C/C=C\CCCCC