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Structure Database (LMSD)

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Common Name

20-HETE

Systematic Name

20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid

Synonyms

20-hydroxy Arachidonic Acid

LM ID

LMFA03060009

Formula

C₂₀H₃₂O₃

Exact Mass

Calculate m/z

320.235145

Sum Composition

FA 20:4;O

Status

Curated

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Classification

Biological Context

20-HETE is a cytochrome P450 (CYP450) metabolite postulated to play an autacoid role in the renal and cerebral vasculature.¹ In rat cerebral microvessels, 20-HETE is a vasoconstrictor that mediates pressure-induced autoregulatory vasoconstriction.² 20-HETE is excreted mainly as the glucuronide conjugate. The concentration of free 20-HETE (20-40 pg/ml in human urine) is about 10-fold lower than the corresponding concentration of the 20-glucuronide.³ 20-HETE can be further metabolized by cyclooxygenase to 20-hydroxy PGG2 and 20-hydroxy PGH2.4

This information has been provided by Cayman Chemical

References

1. Schwartzman, M.L., Falck, J.R., Yadagiri, P., et al. Metabolism of 20-hydroxyeicosatetraenoic acid by cyclooxygenase. Formation and identification of novel endothelium-dependent vasoconstrictor metabolites. The Journal of Biological Chemisty 264(20), 11658-11662 (1989).

2. Prakash, C., Zhang, J.Y., Falck, J.R., et al. 20-Hydroxyeicosatetraenoic acid is excreted as a glucuronide conjugate in human urine. Biochem. Biophys. Res. Commun. 185(2), 728-733 (1992).

3. McGiff, J.C., and Quilley, J. 20-HETE and the kidney: Resolution of old problems and new beginnings. Am. J. Physiol. 277(3), R607-R623 (1999).

4. Gebremedhin, D., Lange, A.R., Lowry, T.F., et al. Production of 20-HETE and its role in autoregulation of cerebral blood flow. Circ. Res. 87(1), 60-65 (2000).

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)

NNDIXBJHNLFJJP-DTLRTWKJSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-

SMILES (Click to copy)

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