N-Arachidonylglycine

N-Arachidonylglycine
Names
	IUPAC name N-[(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoyl]glycine
	Systematic IUPAC name [(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenamido]acetic acid
	Other names N-Arachidonylglycine ; Arachidonoyl glycine ; NA-glycine
Identifiers
CAS Number	179113-91-8 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	7652004
ChEBI	CHEBI:58961 ;
ChEMBL	ChEMBL161343 ;
ChemSpider	4446510 ;
MeSH	Anandamide
PubChem CID	5283389;
UNII	5PB56SQA6E ;
CompTox Dashboard (EPA)	DTXSID5045124 ;
	InChI Key: LGEQQWMQCRIYKG-DOFZRALJSA-N ; InChI=1/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15- Key: YLEARPUNMCCKMP-DOFZRALJSA-N; InChI=1S/C22H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(24)23-20-22(25)26/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-20H2,1H3,(H,23,24)(H,25,26)/b7-6-,10-9-,13-12-,16-15-;
	SMILES O=C(NCC(=O)O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC; O=C(NCC(=O)O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC;
Properties
Chemical formula	C22H35NO3
Molar mass	361.526 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

N-Arachidonylglycine (NAGly) is a carboxylic metabolite of the endocannabinoid anandamide (AEA). Since it was first synthesized in 1996, NAGly has been a primary focus of the relatively contemporary field of lipidomics due to its wide range of signaling targets in the brain, the immune system and throughout various other bodily systems. In combination with 2‐arachidonoyl glycerol (2‐AG), NAGly has enabled the identification of a family of lipids often referred to as endocannabinoids. Recently, NAGly has been found to bind to G-protein coupled receptor 18 (GPR18), the putative abnormal cannabidiol receptor. NaGly is an endogenous inhibitor of fatty acid amide hydrolase (FAAH) and thereby increases the ethanolamide endocannabinoids AEA, oleoylethanolamide (OEA) and palmitoylethanolamide (PEA) levels. NaGly is found throughout the body and research on its explicit functions is ongoing.

Names

IUPAC name N-[(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoyl]glycine
Systematic IUPAC name [(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenamido]acetic acid
Other names N-Arachidonylglycine Arachidonoyl glycine NA-glycine
Identifiers
CAS Number	179113-91-8^Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	7652004
ChEBI	CHEBI:58961^Y
ChEMBL	ChEMBL161343^Y
ChemSpider	4446510^Y
MeSH	Anandamide
PubChem CID	5283389
UNII	5PB56SQA6E^Y
CompTox Dashboard (EPA)	DTXSID5045124
InChI Key: LGEQQWMQCRIYKG-DOFZRALJSA-N^Y InChI=1/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15- Key: YLEARPUNMCCKMP-DOFZRALJSA-N InChI=1S/C22H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(24)23-20-22(25)26/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-20H2,1H3,(H,23,24)(H,25,26)/b7-6-,10-9-,13-12-,16-15-
SMILES O=C(NCC(=O)O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC O=C(NCC(=O)O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
Chemical formula	C₂₂H₃₅NO₃
Molar mass	361.526 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references