General Information of MET (ID: META00084)
Name Oleoylethanolamide
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(9Z)-N-(2-Hydroxyethyl)-9-octadecenamide; N-(2-Hydroxyethyl)-9-Z-octadecenamide; N-(2-Hydroxyethyl)-9-octadecenamide; N-(2-Hydroxyethyl)oleamide; N-(9Z-Octadecenoyl) ethanolamine; N-(9Z-Octadecenoyl)-ethanolamine; N-(Hydroxyethyl)oleamide; N-(cis-9-Octadecenoyl) ethanolamine; N-OEA; N-Oleoyl ethanolamine; N-Oleoyl ethanolamine, oleoyl monoethanolamide, oleoylethanolamide; N-Oleoyl-2-aminoethanol; N-Oleoylethanolamide; N-Oleoylethanolamine; NOE; OEA; Oleamide mea; Oleic acid ethanolamide; Oleic acid monoethanolamide; Oleoyl 1-ethanolamide; Oleoyl ethanolamide; Oleoyl monoethanolamide; Oleoylethanolamide; Oleoylethanolamine
Source Endogenous;Fatty acyls;Food;Cosmetic
Structure Type   Amines  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic nitrogen compounds
Organonitrogen compounds
Amines
PubChem CID
5283454
HMDB ID
HMDB0002088
Formula
C20H39NO2
Structure
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3D MOL is unavailable 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
71466
FooDB ID
FDB022839
ChemSpider ID
4446574
Physicochemical Properties Molecular Weight 325.5 Topological Polar Surface Area 49.3
XlogP 6.3 Complexity 277
Heavy Atom Count 23 Rotatable Bond Count 17
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
Oleoylethanolamide (OEA or NOE) is an N-acylethanolamine. N-Acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation have been attributed to a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. Oleoylethanolamide is an inhibitor of the sphingolipid signalling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). Oleoylethanolamide blocks the effects of TNF and arachidonic acid on intracellular Ca concentration. Oleoylethanolamide is related to the endocannabinoid anandamide. Endocannabinoids signal through cannabinoid receptors (also stimulated by the active ingredient of cannabis) but although related in structure, synthesis, and degradation to anandamide, OEA cannot be considered an endocannabinoid as it does not activate the cannabinoid receptors. Most of the reported responses to OEA can be attributed to the activation of peroxisome proliferator-activated receptor-alpha (PPAR-alpha). Administration of OEA inhibits body weight gain in rats. In adipocytes and hepatocytes, OEA inhibits mitogenic and metabolic signalling by the insulin receptor and produces glucose intolerance. It also inhibits gastric emptying, which might act together with the sensory neuronal signals to achieve satiety. OEA is permanently elevated in diabetic obese patients. OEA also reduces visceral and inflammatory responses through a PPAR-alpha-activation independent mechanism. OEA is an antagonist of TRVP1 (the transient receptor potential vanilloid type 1 receptor). Overall, OEA has beneficial effects on health by inducing food intake control, lipid beta-oxidation, body weight loss and analgesic effects.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      GPCR rhodopsin (GPCR-1)
            Glucose-dependent insulinotropic receptor (GPR119) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Oleoylethanolamide addition (24 hours)
                      Induced Change GPR119 protein expression levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that oleoylethanolamide addition causes the increase of GPR119 protein expression compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of TP53
                      Induced Change Oleoylethanolamide concentration: decrease (Log2 FC=0.66)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of oleoylethanolamide levels compared with control group.
References
1 Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents. Cell Metab. 2006 Mar;3(3):167-75.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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