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
3D model (JSmol)
7652004
ChEBI
ChEMBL
ChemSpider
MeSH Anandamide
UNII
  • Key: LGEQQWMQCRIYKG-DOFZRALJSA-N checkY
  • 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-
  • 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
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).
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N-Arachidonylglycine (NAGly) is a carboxylic metabolite of the endocannabinoid anandamide (AEA).[1][2] Since it was first synthesized in 1996,[3] 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.[4] Recently, NAGly has been found to bind to G-protein coupled receptor 18 (GPR18), the putative abnormal cannabidiol receptor.[5][6] NaGly is an endogenous inhibitor of fatty acid amide hydrolase (FAAH) and thereby increases the ethanolamide endocannabinoids AEA, oleoylethanolamide (OEA) and palmitoylethanolamide (PEA) levels.[7] NaGly is found throughout the body and research on its explicit functions is ongoing.

  1. ^ Burstein SH, Huang SM, Petros TJ, Rossetti RG, Walker JM, Zurier RB (October 2002). "Regulation of anandamide tissue levels by N-arachidonylglycine". Biochemical Pharmacology. 64 (7): 1147–50. doi:10.1016/S0006-2952(02)01301-1. PMID 12234618.
  2. ^ Bradshaw HB, Rimmerman N, Hu SS, Benton VM, Stuart JM, Masuda K, Cravatt BF, O'Dell DK, Walker JM (May 2009). "The endocannabinoid anandamide is a precursor for the signaling lipid N-arachidonoyl glycine by two distinct pathways". BMC Biochemistry. 10: 14. doi:10.1186/1471-2091-10-14. PMC 2689249. PMID 19460156.
  3. ^ Sheskin T, Hanus L, Slager J, Vogel Z, Mechoulam R (February 1997). "Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor". Journal of Medicinal Chemistry. 40 (5): 659–67. doi:10.1021/jm960752x. PMID 9057852.
  4. ^ Bradshaw HB, Rimmerman N, Hu SS, Burstein S, Walker JM (2009). Novel endogenous N-acyl glycines identification and characterization. Vitamins & Hormones. Vol. 81. pp. 191–205. doi:10.1016/S0083-6729(09)81008-X. ISBN 9780123747822. PMID 19647113.
  5. ^ McHugh D, Hu SS, Rimmerman N, Juknat A, Vogel Z, Walker JM, Bradshaw HB (March 2010). "N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor". BMC Neuroscience. 11 (1): 44. doi:10.1186/1471-2202-11-44. PMC 2865488. PMID 20346144.
  6. ^ Kohno M, Hasegawa H, Inoue A, Muraoka M, Miyazaki T, Oka K, Yasukawa M (September 2006). "Identification of N-arachidonylglycine as the endogenous ligand for orphan G-protein-coupled receptor GPR18". Biochemical and Biophysical Research Communications. 347 (3): 827–32. doi:10.1016/j.bbrc.2006.06.175. PMID 16844083.
  7. ^ Tegeder I (February 2016). "Endocannabinoids as Guardians of Metastasis". International Journal of Molecular Sciences. 17 (2): 230. doi:10.3390/ijms17020230. PMC 4783962. PMID 26875980.