Structure Database (LMSD)

Common Name
18-HETE
Systematic Name
18-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
Synonyms
LM ID
LMFA03060092
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

(±)18-HETE is the racemic version of a cytochrome P450 (CYP450) metabolite of arachidonic acid. When formed by the CYP2E1 isoform, 18-HETE is comprised 100% of the (R) isomer.1 18(R)-HETE dose-dependently stimulates vasodilation of the rabbit kidney, whereas 18(S)-HETE does not affect perfusion pressure.2 18-HETE has negligible effects on ATPase activity.2 18(R)-HETE at 1 µM completely blocks 20-HETE-induced vasoconstriction of renal arterioles.3

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).
2. 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).
3. Zhang, F., Deng, H., Kemp, R., et al. Decreased levels of cytochrome P450 2E1-derived eicosanoids sensitize renal arteries to constrictor agonists in spontaneously hypertensive rats. Hypertension 45(1), 103-108 (2005).

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

String Representations

InChiKey (Click to copy)
PPCHNRUZQWLEMF-XBOCNYGYSA-N
InChi (Click to copy)
InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCC(O)CC)=C/C/C=C\CCCC(=O)O

Other Databases

HMDB ID
HMDB0062302
CHEBI ID
63579
PubChem CID
6442778
SwissLipids ID
SLM:000389416
Cayman ID
10010638
GuidePharm ID
6924

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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