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Structure Database (LMSD)

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Common Name

9-HETE

Systematic Name

9-hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acid

Synonyms

LM ID

LMFA03060089

Formula

C₂₀H₃₂O₃

Exact Mass

Calculate m/z

320.235145

Sum Composition

FA 20:4;O

Status

Curated

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Classification

Biological Context

(±)9-HETE is a monohydroxy fatty acid formed by lipid peroxidation of arachidonic acid , as well as by rat liver microsomal cytochrome P450 (CYP).^1,2 Plasma levels of (±)9-HETE are elevated in patients with angiographically defined coronary artery disease.³

This information has been provided by Cayman Chemical

References

1. Shishehbor, M.H., Zhang, R., Medina, H., et al. Systemic elevations of free radical oxidation products of arachidonic acid are associated with angiographic evidence of coronary artery disease. Free Rad. Biol. Med. 41(11), 1678-1683 (2006).

2. 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).

3. Capdevila, J., Yadagiri, P., Manna, S., et al. Absolute configuration of the hydroxyeicosatetraenoic acids (HETEs) formed during catalytic oxygenation of arachidonic acid by microsomal cytochrome P-450. Biochem. Biophys. Res. Commun. 141(3), 1007-1011 (1986).

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)

KATOYYZUTNAWSA-OIZRIKEUSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-10-13-16-19(21)17-14-11-9-12-15-18-20(22)23/h6-7,9-11,13-14,17,19,21H,2-5,8,12,15-16,18H2,1H3,(H,22,23)/b7-6-,11-9-,13-10-,17-14+

SMILES (Click to copy)

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