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
318.219495
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

2. Yamada, H., Oshiro, E., Kikuchi, S., et al. Hydroxyeicosapentaenoic acids from the Pacific krill show high ligand activities for PPARs. J. Lipid Res. 55(5), 895-904 (2014).
3. Fischer, R., Konkel, A., Mehling, H., et al. Dietary omega-3 fatty acids modulate the eicosanoid profile in man primarily via the CYP-epoxygenase pathway. J. Lipid Res. 55(6), 1150-1164 (2014).

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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