LIPID MAPS

Structure Database (LMSD)

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Common Name

16R-HETE

Systematic Name

16R-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid

Synonyms

LM ID

LMFA03060069

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

Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. 16-HETE is a minor CYP450 metabolite of arachidonic acid released by the kidney upon angiotensin II stimulation that demonstrates stereospecific biological activity. 16(R)-HETE inhibits proximal tubule ATPase activity by as much as 60% at a concentration of 2 µM.¹

This information has been provided by Cayman Chemical

References

1. Carroll, M.A., Balazy, M., Margiotta, P., et al. Cytochrome P-450-dependent HETEs: Profile of biological activity and stimulation by vasoactive peptides. Am. J. Physiol. 271(4 Pt 2), R863-R869 (1996).

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)

JEKNPVYFNMZRJG-STHMYGMFSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14-/t19-/m1/s1

SMILES (Click to copy)

C(/C/C=C\C/C=C\[C@H](O)CCCC)=C/C/C=C\CCCC(=O)O