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
Stucture :
Protein : human-MGLL
References (3)
| Title : N-arachidonyl maleimide potentiates the pharmacological and biochemical effects of the endocannabinoid 2-arachidonylglycerol through inhibition of monoacylglycerol lipase - Burston_2008_J.Pharmacol.Exp.Ther_327_546 |
| Author(s) : Burston JJ , Sim-Selley LJ , Harloe JP , Mahadevan A , Razdan RK , Selley DE , Wiley JL |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 327 :546 , 2008 |
| Abstract : Burston_2008_J.Pharmacol.Exp.Ther_327_546 |
| ESTHER : Burston_2008_J.Pharmacol.Exp.Ther_327_546 |
| PubMedSearch : Burston_2008_J.Pharmacol.Exp.Ther_327_546 |
| PubMedID: 18682568 |
| Title : Covalent inhibitors of human monoacylglycerol lipase: ligand-assisted characterization of the catalytic site by mass spectrometry and mutational analysis - Zvonok_2008_Chem.Biol_15_854 |
| Author(s) : Zvonok N , Pandarinathan L , Williams J , Johnston M , Karageorgos I , Janero DR , Krishnan SC , Makriyannis A |
| Ref : Chemical Biology , 15 :854 , 2008 |
| Abstract : Zvonok_2008_Chem.Biol_15_854 |
| ESTHER : Zvonok_2008_Chem.Biol_15_854 |
| PubMedSearch : Zvonok_2008_Chem.Biol_15_854 |
| PubMedID: 18721756 |
| Title : Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes - Saario_2005_Chem.Biol_12_649 |
| Author(s) : Saario SM , Salo OM , Nevalainen T , Poso A , Laitinen JT , Jarvinen T , Niemi R |
| Ref : Chemical Biology , 12 :649 , 2005 |
| Abstract : Saario_2005_Chem.Biol_12_649 |
| ESTHER : Saario_2005_Chem.Biol_12_649 |
| PubMedSearch : Saario_2005_Chem.Biol_12_649 |
| PubMedID: 15975510 |