Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H39NO2 |
Molecular Weight | 325.5292 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)NCCO
InChI
InChIKey=BOWVQLFMWHZBEF-KTKRTIGZSA-N
InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
Molecular Formula | C20H39NO2 |
Molecular Weight | 325.5292 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Oleoylethanolamide (oleic monoethanolamide, OEA), the naturally occurring amide of ethanolamine and oleic acid, is an endogenous lipid that modulates feeding, body weight, and lipid metabolism by binding with high affinity to the ligand-activated transcription factor, peroxisome proliferator-activated receptor-alpha (PPAR-alpha). OEA reveals the pharmacological properties in the treatment of obesity, atherosclerosis and other diseases. It was shown, that OEA can be used to control hunger in Prader-Willi syndrome, in addition, it exhibited neuroprotective properties in Parkinson's disease experiments. OEA is an endogenous ligand of the orphan receptor GPR119, a G protein-coupled receptor (GPCR) expressed predominantly in the human and rodent pancreas and gastrointestinal tract and in rodent brain, suggesting that the reported effects of OEA on food intake may be mediated, at least in part, via the GPR119 receptor. Recently was shown, that OEA was an effective inhibitor of hyperpigmentation through activation of ERK, Akt and p38 pathways, inhibition of the CREB pathway, and subsequent down-regulation of MITF, TRP-1 and tyrosinase production. Therefore, OEA could be a useful therapeutic agent for use in the treatment of hyperpigmentation and could be an effective component in whitening and lightening cosmetics.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24169105
Curator's Comment: Known to be CNS active in rats. Human data not available
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q07869 Gene ID: 5465.0 Gene Symbol: PPARA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15770421 |
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Target ID: Q8TDV5 Gene ID: 139760.0 Gene Symbol: GPR119 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16517404 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Ceramide mediates tumor-induced dendritic cell apoptosis. | 2001 Oct 1 |
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Myocardial dysfunction with coronary microembolization: signal transduction through a sequence of nitric oxide, tumor necrosis factor-alpha, and sphingosine. | 2002 Apr 19 |
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N-Acylethanolamines in human reproductive fluids. | 2002 Dec 31 |
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Synthesis of a novel fluorescent ceramide analogue and its use in the characterization of recombinant ceramidase from Pseudomonas aeruginosa PA01. | 2002 Feb |
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Arachidonic acid mediates dual effect of TNF-alpha on Ca2+ transients and contraction of adult rat cardiomyocytes. | 2002 Jun |
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N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein. | 2003 Apr |
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Activation of TRPV1 by the satiety factor oleoylethanolamide. | 2003 Aug 15 |
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The presence of ceramidase activity in liver nuclear membrane. | 2003 Jun |
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Endotoxin-induced myocardial dysfunction: evidence for a role of sphingosine production. | 2004 Feb |
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Synthesis and biological evaluation of phosphonic and thiophosphoric acid derivatives of lysophosphatidic acid. | 2004 Jul 5 |
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Further evidence for the existence of a specific process for the membrane transport of anandamide. | 2004 May 15 |
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In vitro conjugation of ethanolamine with fatty acids by rat liver subcellular fractions. | 2005 Apr 23 |
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Effects of N-acylethanolamines on the respiratory chain and production of reactive oxygen species in heart mitochondria. | 2005 Aug 29 |
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The postmortal accumulation of brain N-arachidonylethanolamine (anandamide) is dependent upon fatty acid amide hydrolase activity. | 2005 Feb |
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The nuclear receptor peroxisome proliferator-activated receptor-alpha mediates the anti-inflammatory actions of palmitoylethanolamide. | 2005 Jan |
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Oleoylethanolamide, an endogenous PPAR-alpha agonist, lowers body weight and hyperlipidemia in obese rats. | 2005 Jun |
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Endogenous unsaturated C18 N-acylethanolamines are vanilloid receptor (TRPV1) agonists. | 2005 Nov 18 |
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A FAAH-regulated class of N-acyl taurines that activates TRP ion channels. | 2006 Aug 1 |
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Intestinal levels of anandamide and oleoylethanolamide in food-deprived rats are regulated through their precursors. | 2006 Feb |
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Synthesis and structure-activity relationships of FAAH inhibitors: cyclohexylcarbamic acid biphenyl esters with chemical modulation at the proximal phenyl ring. | 2006 Jan |
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Postprandial increase of oleoylethanolamide mobilization in small intestine of the Burmese python (Python molurus). | 2006 May |
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Tumor necrosis factor-alpha inhibits the cardiac delayed rectifier K current via the asphingomyelin pathway. | 2006 May 26 |
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GPR55: a new member of the cannabinoid receptor clan? | 2007 Dec |
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Analgesic properties of oleoylethanolamide (OEA) in visceral and inflammatory pain. | 2007 Dec 15 |
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Pharmacological inhibition or small interfering RNA targeting acid ceramidase sensitizes hepatoma cells to chemotherapy and reduces tumor growth in vivo. | 2007 Feb 8 |
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Mechanism of oleoylethanolamide on fatty acid uptake in small intestine after food intake and body weight reduction. | 2007 Jan |
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Food intake regulates oleoylethanolamide formation and degradation in the proximal small intestine. | 2007 Jan 12 |
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Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry. | 2007 Jan 15 |
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Cannabinoid activation of PPAR alpha; a novel neuroprotective mechanism. | 2007 Nov |
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The cannabinoid CB1 receptor antagonist SR141716A (Rimonabant) enhances the metabolic benefits of long-term treatment with oleoylethanolamide in Zucker rats. | 2008 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28007570
fasted/refed Magel2 KO mice: intraperitoneal administration of oleoylethanolamine (OEA) (10mg/kg) significantly reduces food intake, pointing to a possible use of this natural compound to control hunger in Prader-Willi syndrome.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15123613
It was examined whether oleoylethanolamine (OEA) can influence energy utilization. OEA (1-20 microm) stimulated glycerol and fatty acid release from freshly dissociated rat adipocytes in a concentration-dependent and structurally selective manner. Under the same conditions, OEA had no effect on glucose uptake or oxidation. OEA enhanced fatty acid oxidation in skeletal muscle strips, dissociated hepatocytes, and primary cardiomyocyte cultures.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:02:24 GMT 2023
by
admin
on
Fri Dec 15 19:02:24 GMT 2023
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Record UNII |
1HI5J9N8E6
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Record Status |
Validated (UNII)
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FDA ORPHAN DRUG |
577117
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Oleoylethanolamide
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DTXSID1044516
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Related Record | Type | Details | ||
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TARGET -> SUBSTRATE |