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Inhibitor Report for: N-Arachidonylmaleimide

N-Arachidonyl maleimide (NAM) is a potent, irreversible inhibitor of monoacylglycerol lipase (MGLL) with an IC50 value of 140 nM.6 Inhibition of MGLL by the sulfhydryl-reactive maleimide group suggests a critical cysteine residue is present in the substrate-binding site of the enzyme


General
Type Cannabinoid-Receptor-ligand
Chemical_Nomenclature 1-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenyl]pyrrole-2,5-dione
Canonical SMILES CCCCCC=CCC=CCC=CCC=CCCCCN1C(=O)C=CC1=O
InChI InChI=1S/C24H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-25-23(26)20-21-24(25)27/h6-7,9-10,12-13,15-16,20-21H,2-5,8,11,14,17-19,22H2,1H3/b7-6-,10-9-,13-12-,16-15-
InChIKey GZNZRHSGGQUYAP-DOFZRALJSA-N
Other name(s) CHEMBL561924 ; NAM ; N-Arachidonyl Maleimide ; SCHEMBL5086361 ; MolPort-019-939-191
________________________________________________________________________________________________
MW|369.54
Formula|C24H35NO2
CAS_number|876305-42-9
PubChem|25021164
UniChem|GZNZRHSGGQUYAP-DOFZRALJSA-N
IUPHAR|
Wikipedia|N-Arachidonylmaleimide

Target
Families | N-Arachidonylmaleimide ligand of proteins in family: Monoglyceridelipase_lysophospholip
Protein | human-MGLL

References:
Search PubMed for references concerning: N-Arachidonylmaleimide
    Title: N-arachidonyl maleimide potentiates the pharmacological and biochemical effects of the endocannabinoid 2-arachidonylglycerol through inhibition of monoacylglycerol lipase
    Burston JJ, Sim-Selley LJ, Harloe JP, Mahadevan A, Razdan RK, Selley DE, Wiley JL
    Ref: Journal of Pharmacology & Experimental Therapeutics, 327:546, 2008 : PubMed

            

    Title: Covalent inhibitors of human monoacylglycerol lipase: ligand-assisted characterization of the catalytic site by mass spectrometry and mutational analysis
    Zvonok N, Pandarinathan L, Williams J, Johnston M, Karageorgos I, Janero DR, Krishnan SC, Makriyannis A
    Ref: Chemical Biology, 15:854, 2008 : PubMed

            

    Title: Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes
    Saario SM, Salo OM, Nevalainen T, Poso A, Laitinen JT, Jarvinen T, Niemi R
    Ref: Chemical Biology, 12:649, 2005 : PubMed