General Information of MET (ID: META00077)
Name Anandamide
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide; (all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide; 5,8,11,14-Eicosatetraenoylethanolamide; AEA; Anandamide; Anandamide (20.4, N-6); Anandamide (20.4,N-6); Anandamide(20:4, N-6); Arachidonate N-(hydroxyethyl)amide; Arachidonic acid N-(hydroxyethyl)amide; Arachidonoyl ethanolamide; Arachidonoylethanolamide; Arachidonylethanolamide; N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide (all-Z); N-(2-Hydroxyethyl)anachidonamide; N-(2-Hydroxyethyl)arachidonamide; N-(2-Hydroxyethyl)arachidonylamide; N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl) ethanolamine; N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-ethanolamine; N-(5Z,8Z,11Z,14Z-Icosatetraenoyl)-ethanolamide; N-Arachidonoyl ethanolamine; N-Arachidonoyl-2-hydroxyethylamide; N-Arachidonoylethanolamide; N-Arachidonoylethanolamine; N-Arachidonylethanolamide; N-Arachidonylethanolamine
Source Endogenous;Fatty acyls;Food
Structure Type   Amines  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic nitrogen compounds
Organonitrogen compounds
Amines
PubChem CID
5281969
HMDB ID
HMDB0004080
Formula
C22H37NO2
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
KEGG ID
C11695
ChEBI ID
2700
FooDB ID
FDB023303
ChemSpider ID
4445241
Physicochemical Properties Molecular Weight 347.5 Topological Polar Surface Area 49.3
XlogP 5.4 Complexity 408
Heavy Atom Count 25 Rotatable Bond Count 16
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
Anandamide, also known as arachidonoylethanolamide (AEA), is a highly potent endogenous agonist of the cannabinoid CB1 and CB2 receptors. CB1 receptors are predominantly found in the central nervous system (CNS) where they mainly mediate the psychotropic effects of tetrahydrocannabinol (THC) and endocannabinoids, whereas the expression of the CB2 receptor is thought to be restricted to cells of the immune system. It was suggested that AEA might inhibit tumour cell proliferation or induce apoptosis independently of CB1 and CB2 receptors, via interaction with the type 1 vanilloid receptor (VR1). VR1 is an ion channel expressed almost exclusively by sensory neurons, activated by pH, noxious heat (> 48-degree centigrade), and plant toxins and is thought to play an important role in nociception. Cervical cancer cells are sensitive to AEA-induced apoptosis via VR1 that is aberrantly expressed in vitro and in vivo while CB1 and CB2 receptors play a protective role. Novel prostaglandins (prostaglandin glycerol esters and prostaglandin ethanolamides) are COX-2 oxidative metabolites of endogenous cannabinoids (such as anandamide). Recent evidence suggests that these new types of prostaglandins are likely novel signalling mediators involved in synaptic transmission and plasticity.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      Transferases (EC 2)
            Signal-regulated kinase 1 (ERK1) 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 Anandamide addition (0.083 hour)
                      Induced Change MAPK3 protein phosphorylation levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Endometriosis [ICD-11: GA10]
                      Details It is reported that anandamide addition causes the increase of MAPK3 protein phosphorylation compared with control group.
            Signal-regulated kinase 2 (ERK2) 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 Anandamide addition (0.08 hours)
                      Induced Change MAPK1 protein phosphorylation levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Endometriosis [ICD-11: GA10]
                      Details It is reported that anandamide addition causes the increase of MAPK1 protein phosphorylation compared with control group.
References
1 (9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells. Br J Pharmacol. 2012 Apr;165(8):2414-24.

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