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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
Structure of OLEIC MONOETHANOLAMIDE

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-

HIDE SMILES / InChI

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

Curator's Comment: Known to be CNS active in rats. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q07869
Gene ID: 5465.0
Gene Symbol: PPARA
Target Organism: Homo sapiens (Human)
Target ID: Q8TDV5
Gene ID: 139760.0
Gene Symbol: GPR119
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Ceramide mediates tumor-induced dendritic cell apoptosis.
2001 Oct 1
Myocardial dysfunction with coronary microembolization: signal transduction through a sequence of nitric oxide, tumor necrosis factor-alpha, and sphingosine.
2002 Apr 19
N-Acylethanolamines in human reproductive fluids.
2002 Dec 31
Synthesis of a novel fluorescent ceramide analogue and its use in the characterization of recombinant ceramidase from Pseudomonas aeruginosa PA01.
2002 Feb
Arachidonic acid mediates dual effect of TNF-alpha on Ca2+ transients and contraction of adult rat cardiomyocytes.
2002 Jun
N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein.
2003 Apr
Activation of TRPV1 by the satiety factor oleoylethanolamide.
2003 Aug 15
The presence of ceramidase activity in liver nuclear membrane.
2003 Jun
Endotoxin-induced myocardial dysfunction: evidence for a role of sphingosine production.
2004 Feb
Synthesis and biological evaluation of phosphonic and thiophosphoric acid derivatives of lysophosphatidic acid.
2004 Jul 5
Further evidence for the existence of a specific process for the membrane transport of anandamide.
2004 May 15
In vitro conjugation of ethanolamine with fatty acids by rat liver subcellular fractions.
2005 Apr 23
Effects of N-acylethanolamines on the respiratory chain and production of reactive oxygen species in heart mitochondria.
2005 Aug 29
The postmortal accumulation of brain N-arachidonylethanolamine (anandamide) is dependent upon fatty acid amide hydrolase activity.
2005 Feb
The nuclear receptor peroxisome proliferator-activated receptor-alpha mediates the anti-inflammatory actions of palmitoylethanolamide.
2005 Jan
Oleoylethanolamide, an endogenous PPAR-alpha agonist, lowers body weight and hyperlipidemia in obese rats.
2005 Jun
Endogenous unsaturated C18 N-acylethanolamines are vanilloid receptor (TRPV1) agonists.
2005 Nov 18
A FAAH-regulated class of N-acyl taurines that activates TRP ion channels.
2006 Aug 1
Intestinal levels of anandamide and oleoylethanolamide in food-deprived rats are regulated through their precursors.
2006 Feb
Synthesis and structure-activity relationships of FAAH inhibitors: cyclohexylcarbamic acid biphenyl esters with chemical modulation at the proximal phenyl ring.
2006 Jan
Postprandial increase of oleoylethanolamide mobilization in small intestine of the Burmese python (Python molurus).
2006 May
Tumor necrosis factor-alpha inhibits the cardiac delayed rectifier K current via the asphingomyelin pathway.
2006 May 26
GPR55: a new member of the cannabinoid receptor clan?
2007 Dec
Analgesic properties of oleoylethanolamide (OEA) in visceral and inflammatory pain.
2007 Dec 15
Pharmacological inhibition or small interfering RNA targeting acid ceramidase sensitizes hepatoma cells to chemotherapy and reduces tumor growth in vivo.
2007 Feb 8
Mechanism of oleoylethanolamide on fatty acid uptake in small intestine after food intake and body weight reduction.
2007 Jan
Food intake regulates oleoylethanolamide formation and degradation in the proximal small intestine.
2007 Jan 12
Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry.
2007 Jan 15
Cannabinoid activation of PPAR alpha; a novel neuroprotective mechanism.
2007 Nov
The cannabinoid CB1 receptor antagonist SR141716A (Rimonabant) enhances the metabolic benefits of long-term treatment with oleoylethanolamide in Zucker rats.
2008 Jan
Patents

Patents

Sample Use Guides

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
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 Fri Dec 15 19:02:24 GMT 2023
Edited
by admin
on Fri Dec 15 19:02:24 GMT 2023
Record UNII
1HI5J9N8E6
Record Status Validated (UNII)
Record Version
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Name Type Language
OLEIC MONOETHANOLAMIDE
Common Name English
(Z)-N-(2-HYDROXYETHYL)OCTADEC-9-ENAMIDE
Systematic Name English
OLEOYLETHANOLAMIDE
Common Name English
9-OCTADECENAMIDE, N-(2-HYDROXYETHYL)-
Systematic Name English
Oleylethanolamide [WHO-DD]
Common Name English
9-OCTADECENAMIDE, N-(2-HYDROXYETHYL)-, Z
Common Name English
N-(2-HYDROXYETHYL)OLEAMIDE
Systematic Name English
N-OLEOYL ETHANOLAMIDE
Common Name English
OLEOYL MONOETHANOLAMIDE
Common Name English
OLEAMIDE MEA
INCI  
INCI  
Official Name English
OLEAMIDE MEA [INCI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 577117
Created by admin on Fri Dec 15 19:02:24 GMT 2023 , Edited by admin on Fri Dec 15 19:02:24 GMT 2023
Code System Code Type Description
FDA UNII
1HI5J9N8E6
Created by admin on Fri Dec 15 19:02:24 GMT 2023 , Edited by admin on Fri Dec 15 19:02:24 GMT 2023
PRIMARY
ECHA (EC/EINECS)
203-884-8
Created by admin on Fri Dec 15 19:02:24 GMT 2023 , Edited by admin on Fri Dec 15 19:02:24 GMT 2023
PRIMARY
CAS
111-58-0
Created by admin on Fri Dec 15 19:02:24 GMT 2023 , Edited by admin on Fri Dec 15 19:02:24 GMT 2023
PRIMARY
CHEBI
71466
Created by admin on Fri Dec 15 19:02:24 GMT 2023 , Edited by admin on Fri Dec 15 19:02:24 GMT 2023
PRIMARY
PUBCHEM
5283454
Created by admin on Fri Dec 15 19:02:24 GMT 2023 , Edited by admin on Fri Dec 15 19:02:24 GMT 2023
PRIMARY
WIKIPEDIA
Oleoylethanolamide
Created by admin on Fri Dec 15 19:02:24 GMT 2023 , Edited by admin on Fri Dec 15 19:02:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID1044516
Created by admin on Fri Dec 15 19:02:24 GMT 2023 , Edited by admin on Fri Dec 15 19:02:24 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> SUBSTRATE