LIPID MAPS

Structure Database (LMSD)

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Common Name

19S-HETE

Systematic Name

19S-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid

Synonyms

LM ID

LMFA03060074

Formula

C₂₀H₃₂O₃

Exact Mass

Calculate m/z

320.235146

Sum Composition

FA 20:4;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Biological Context

19-HETE is one of the major cytochrome P450 (CYP450) metabolites of arachidonic acid that is released from the kidney in response to angiotensin II. When formed by the CYP2E1 isoform, 19-HETE is composed of 70% and 30% of the (S) and (R) stereoisomers, respectively.¹ Both 19(S)- and 19(R)-HETE are potent vasodilators of renal preglomerular vessels.² 19(S)-HETE stimulates both renal sodium-potassium ATPase and volume absorption in the rabbit proximal straight tubule.^3,4

This information has been provided by Cayman Chemical

References

1. Escalante, B., Falck, J.R., Yadagiri, P., et al. 19(S)-Hydroxyeicosatetraenoic acid is a potent simulator of renal Na+-K+-ATPase. Biochem. Biophys. Res. Commun. 152(3), 1269-1274 (1988).

2. 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).

3. Laethem, R.M., Balazy, M., Falck, J.R., et al. Formation of 19(S)-, 19(R)-, and 18(R)-hydroxyeicosatetraenoic acids by alcohol-inducible cytochrome P450 2E1. The Journal of Biological Chemisty 268(17), 12912-12918 (1993).

4. Quigley, R., Baum, M., Reddy, K.M., et al. Effects of 20-HETE and 19(S)-HETE on rabbit proximal straight tubule volume transport. Am. J. Physiol. Renal Physiol. 278(6), F949-F953 (2000).

String Representations

InChiKey (Click to copy)

XFUXZHQUWPFWPR-DZBJBCEBSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-19(21)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18-20(22)23/h3-6,9-12,19,21H,2,7-8,13-18H2,1H3,(H,22,23)/b5-3-,6-4-,11-9-,12-10-/t19-/m0/s1

SMILES (Click to copy)

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