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Structure Database (LMSD)

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Common Name

16-HETE

Systematic Name

(5Z,8Z,11Z,14Z)-16-hydroxyicosa-5,8,11,14-tetraenoic acid

Synonyms

(5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
(all-cis)-16-hydroxy-5,8,11,14-eicosatetraenoic acid
(all-cis)-16-hydroxy-5,8,11,14-icosatetraenoic acid
16-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid

LM ID

LMFA03060105

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 the racemic version of a minor CYP450 metabolite of arachidonic acid released by the kidney upon angiotensin II stimulation. The biological activity of 16-HETE is stereospecific. 16(R)-HETE dose-dependently stimulates vasodilation of the rabbit kidney, however 16(S)-HETE does not affect perfusion pressure.¹ At a concentration of 2 µM the (S)-enantiomer of 16-HETE inhibits proximal tubule ATPase activity by as much as 60%, whereas the (R)-isomer has negligible effects on ATPase activity.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).

String Representations

InChiKey (Click to copy)

JEKNPVYFNMZRJG-UFINWASNSA-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-

SMILES (Click to copy)

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