Structure Database (LMSD)
Common Name
(+/-)-9-HEPE
Systematic Name
(+/-)-9-hydroxy-5Z,7E,11Z,14Z,17Z-eicosapentaenoic acid
Synonyms
3D model of (+/-)-9-HEPE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
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
J Lipid Res, 2010
Pubmed ID:
20671299
DOI:
10.1194/jlr.M009449
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
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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