Structure Database (LMSD)

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
320.235145
Sum Composition
FA 20:4;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]

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

Other Databases

KEGG ID
C14749
HMDB ID
HMDB0011136
CHEBI ID
34185
PubChem CID
9548883
Cayman ID
10007766

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 367.73
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.47
Molar Refractivity 97.94

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