Details of Metabolite

General Information of MET (ID: META00078)
Name N-Arachidonoylglycine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
EMA-1 20:4; N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-glycine; N-Arachidonoyl glycinate; N-Arachidonoyl glycine; N-Arachidonoylglycinate; N-Arachidonoylglycine; N-Arachidonyl-L-glycine; N-Arachidonylglycine; N-[(5Z,8Z,11Z,14Z)-1-Oxo-5,8,11,14-eicosatetraen-1-yl]glycine; NAGly; NAGly amino acid
Source Endogenous;Fatty acyls;Food
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
5283389
HMDB ID
HMDB0005096
Formula
C22H35NO3
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
58961
FooDB ID
FDB023629
ChemSpider ID
4446510
Physicochemical Properties Molecular Weight 361.5 Topological Polar Surface Area 66.4
XlogP 5.6 Complexity 476
Heavy Atom Count 26 Rotatable Bond Count 16
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
N-Arachidonoylglycine (NAGly) is an endogenous lipid, which is a metabolite of the endocannabinoid anandamide by oxidation and acts as an efficacious agonist at GPR18. A previous study demonstrates that NAGly triggers antinociceptive and anti-inflammatory activities.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      GPCR rhodopsin (GPCR-1)
            Lysophosphatidic acid receptor 5 (LPAR5) 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 N-Arachidonoylglycine addition (24 hours)
                      Induced Change LPAR5 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Hepatocellular carcinoma [ICD-11: 2C12]
                      Details It is reported that N-arachidonoylglycine addition causes the increase of LPAR5 protein activity compared with control group.
      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 [2]
                      Introduced Variation N-Arachidonoylglycine addition (0.08 hours)
                      Induced Change MAPK3 protein phosphorylation levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Endometriosis [ICD-11: GA10]
                      Details It is reported that N-arachidonoylglycine 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 [2]
                      Introduced Variation N-Arachidonoylglycine 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 N-arachidonoylglycine addition causes the increase of MAPK1 protein phosphorylation compared with control group.
References
1 Unique ligand selectivity of the GPR92/LPA5 lysophosphatidate receptor indicates role in human platelet activation. J Biol Chem. 2009 Jun 19;284(25):17304-17319.
2 (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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