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 |
|---|---|---|---|
Target ID: Q07869 Gene ID: 5465.0 Gene Symbol: PPARA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15770421 |
|||
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 |
|---|---|---|---|---|
| Palliative | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Influence of dietary fatty acids on endocannabinoid and N-acylethanolamine levels in rat brain, liver and small intestine. | 2008-04 |
|
| Inhibitory effect of the anorexic compound oleoylethanolamide on gastric emptying in control and overweight mice. | 2008-04 |
|
| Actions of 3-methyl-N-oleoyldopamine, 4-methyl-N-oleoyldopamine and N-oleoylethanolamide on the rat TRPV1 receptor in vitro and in vivo. | 2008-03-12 |
|
| Modulation of ceramide metabolism in T-leukemia cell lines potentiates apoptosis induced by the cationic antimicrobial peptide bovine lactoferricin. | 2008-03 |
|
| GPR119, a novel G protein-coupled receptor target for the treatment of type 2 diabetes and obesity. | 2008-03 |
|
| Role of the endocannabinoid system in metabolic control. | 2008-01 |
|
| Evaluation of fatty acid amides in the carrageenan-induced paw edema model. | 2008-01 |
|
| The cannabinoid CB1 receptor antagonist SR141716A (Rimonabant) enhances the metabolic benefits of long-term treatment with oleoylethanolamide in Zucker rats. | 2008-01 |
|
| Epidermal ceramidase activity regulates epidermal desquamation via stratum corneum acidification. | 2008 |
|
| Analgesic properties of oleoylethanolamide (OEA) in visceral and inflammatory pain. | 2007-12-15 |
|
| GPR55: a new member of the cannabinoid receptor clan? | 2007-12 |
|
| Endocannabinoids and related N-acylethanolamines in the control of appetite and energy metabolism: emergence of new molecular players. | 2007-11 |
|
| Cannabinoid activation of PPAR alpha; a novel neuroprotective mechanism. | 2007-11 |
|
| Novel cannabinoid receptors. | 2007-11 |
|
| Cannabinoids go nuclear: evidence for activation of peroxisome proliferator-activated receptors. | 2007-11 |
|
| Peroxisome proliferator-activated receptor-alpha is required for the neurotrophic effect of oleic acid in neurons. | 2007-11 |
|
| The G protein-coupled receptor subset of the rat genome. | 2007-09-25 |
|
| Effect of polyunsaturated fatty acids on endocannabinoid and N-acyl-ethanolamine levels in mouse adipocytes. | 2007-07-13 |
|
| Effects of the fatty acid amide hydrolase inhibitor URB597 on the sleep-wake cycle, c-Fos expression and dopamine levels of the rat. | 2007-05-07 |
|
| Predominant expression of lysosomal N-acylethanolamine-hydrolyzing acid amidase in macrophages revealed by immunochemical studies. | 2007-05 |
|
| Determination of anandamide and other fatty acyl ethanolamides in human serum by electrospray tandem mass spectrometry. | 2007-02-15 |
|
| Pharmacological inhibition or small interfering RNA targeting acid ceramidase sensitizes hepatoma cells to chemotherapy and reduces tumor growth in vivo. | 2007-02-08 |
|
| Novel sulfamide analogs of oleoylethanolamide showing in vivo satiety inducing actions and PPARalpha activation. | 2007-01-25 |
|
| Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry. | 2007-01-15 |
|
| Food intake regulates oleoylethanolamide formation and degradation in the proximal small intestine. | 2007-01-12 |
|
| Mechanism of oleoylethanolamide on fatty acid uptake in small intestine after food intake and body weight reduction. | 2007-01 |
|
| Cannabinoids: a new group of agonists of PPARs. | 2007 |
|
| Analgesic effects of fatty acid amide hydrolase inhibition in a rat model of neuropathic pain. | 2006-12-20 |
|
| Expression and distribution of Gpr119 in the pancreatic islets of mice and rats: predominant localization in pancreatic polypeptide-secreting PP-cells. | 2006-12-15 |
|
| Synergistic antinociceptive effects of anandamide, an endocannabinoid, and nonsteroidal anti-inflammatory drugs in peripheral tissue: a role for endogenous fatty-acid ethanolamides? | 2006-11-21 |
|
| Design, synthesis and activity as acid ceramidase inhibitors of 2-oxooctanoyl and N-oleoylethanolamine analogues. | 2006-10 |
|
| Critical role of acidic sphingomyelinase in murine hepatic ischemia-reperfusion injury. | 2006-09 |
|
| Cold exposure stimulates synthesis of the bioactive lipid oleoylethanolamide in rat adipose tissue. | 2006-08-11 |
|
| A FAAH-regulated class of N-acyl taurines that activates TRP ion channels. | 2006-08-01 |
|
| High-throughput screening for the discovery of inhibitors of fatty acid amide hydrolase using a microsome-based fluorescent assay. | 2006-08 |
|
| Pharmacological characterization of hydrolysis-resistant analogs of oleoylethanolamide with potent anorexiant properties. | 2006-08 |
|
| Targeted lipidomics: discovery of new fatty acyl amides. | 2006-07-14 |
|
| Diurnal variation of arachidonoylethanolamine, palmitoylethanolamide and oleoylethanolamide in the brain of the rat. | 2006-05-30 |
|
| Tumor necrosis factor-alpha inhibits the cardiac delayed rectifier K current via the asphingomyelin pathway. | 2006-05-26 |
|
| Postprandial increase of oleoylethanolamide mobilization in small intestine of the Burmese python (Python molurus). | 2006-05 |
|
| Oxyhomologues of anandamide and related endolipids: chemoselective synthesis and biological activity. | 2006-04-06 |
|
| Oleoylethanolamide protects human sperm cells from oxidation stress: studies on cases of idiopathic infertility. | 2006-04 |
|
| Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents. | 2006-03 |
|
| Importance of C16 ceramide accumulation during apoptosis in prostate cancer cells. | 2006-02 |
|
| Intestinal levels of anandamide and oleoylethanolamide in food-deprived rats are regulated through their precursors. | 2006-02 |
|
| Synthesis and structure-activity relationships of FAAH inhibitors: cyclohexylcarbamic acid biphenyl esters with chemical modulation at the proximal phenyl ring. | 2006-01 |
|
| Endogenous unsaturated C18 N-acylethanolamines are vanilloid receptor (TRPV1) agonists. | 2005-11-18 |
|
| Involvement of N-acylethanolamine-hydrolyzing acid amidase in the degradation of anandamide and other N-acylethanolamines in macrophages. | 2005-10-01 |
|
| Fatty acid amide hydrolase controls mouse intestinal motility in vivo. | 2005-09 |
|
| Effects of N-acylethanolamines on the respiratory chain and production of reactive oxygen species in heart mitochondria. | 2005-08-29 |
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
Mon Mar 31 19:31:02 GMT 2025
by
admin
on
Mon Mar 31 19:31:02 GMT 2025
|
| Record UNII |
1HI5J9N8E6
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
FDA ORPHAN DRUG |
577117
Created by
admin on Mon Mar 31 19:31:02 GMT 2025 , Edited by admin on Mon Mar 31 19:31:02 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
1HI5J9N8E6
Created by
admin on Mon Mar 31 19:31:02 GMT 2025 , Edited by admin on Mon Mar 31 19:31:02 GMT 2025
|
PRIMARY | |||
|
203-884-8
Created by
admin on Mon Mar 31 19:31:02 GMT 2025 , Edited by admin on Mon Mar 31 19:31:02 GMT 2025
|
PRIMARY | |||
|
111-58-0
Created by
admin on Mon Mar 31 19:31:02 GMT 2025 , Edited by admin on Mon Mar 31 19:31:02 GMT 2025
|
PRIMARY | |||
|
71466
Created by
admin on Mon Mar 31 19:31:02 GMT 2025 , Edited by admin on Mon Mar 31 19:31:02 GMT 2025
|
PRIMARY | |||
|
5283454
Created by
admin on Mon Mar 31 19:31:02 GMT 2025 , Edited by admin on Mon Mar 31 19:31:02 GMT 2025
|
PRIMARY | |||
|
Oleoylethanolamide
Created by
admin on Mon Mar 31 19:31:02 GMT 2025 , Edited by admin on Mon Mar 31 19:31:02 GMT 2025
|
PRIMARY | |||
|
DTXSID1044516
Created by
admin on Mon Mar 31 19:31:02 GMT 2025 , Edited by admin on Mon Mar 31 19:31:02 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
TARGET -> SUBSTRATE |