Structure Database (LMSD)

Common Name
(+/-)-9-HEPE
Systematic Name
(+/-)-9-hydroxy-5Z,7E,11Z,14Z,17Z-eicosapentaenoic acid
Synonyms
LM ID
LMFA03070029
Formula
Exact Mass
Calculate m/z
318.219496
Sum Composition
Status
Curated



Classification

Biological Context

(±)9-HEPE is a racemic mixture of the monohydroxy fatty acids 9(R)-HEPE and 9(S)-HEPE . It is produced by non-enzymatic oxidation of eicosapentaenoic acid (EPA).1 (±)9-HEPE (128 µM) induces peroxisome proliferator-activated receptor α (PPARα), PPARγ, and PPARδ transactivation in NIH3T3 cells expressing the mouse receptors.2 It reduces increases in the expression of the genes encoding inducible nitric oxide synthase (iNOS), TNF-α, IL-1β, and IL-6 in isolated mouse peritoneal macrophages induced by palmitate, as well as inhibits palmitate-induced migration of isolated mouse peritoneal macrophages, when used at a concentration of 1 µM.3 (±)9-HEPE decreases hepatic triglyceride levels and plasma LDL-cholesterol and total cholesterol levels in a mouse model of high-fat diet-induced hepatic steatosis when administered in combination with (±)5-HEPE and (±)17,18-EEQ ((±)17(18)-EpETE).

This information has been provided by Cayman Chemical

References

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)
OXOPDAZWPWFJEW-IMCWFPBLSA-N
InChi (Click to copy)
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-10-13-16-19(21)17-14-11-9-12-15-18-20(22)23/h3-4,6-7,9-11,13-14,17,19,21H,2,5,8,12,15-16,18H2,1H3,(H,22,23)/b4-3-,7-6-,11-9-,13-10-,17-14+
SMILES (Click to copy)
C(CCC/C=C\C=C\C(O)C/C=C\C/C=C\C/C=C\CC)(=O)O

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 0
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 365.09
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.25
Molar Refractivity 97.85

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Updated at
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