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
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
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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