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
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
Wikipedia : N-Arachidonylmaleimide
Families : N-Arachidonylmaleimide ligand of proteins in family
Monoglyceridelipase_lysophospholip
Protein :
human-MGLL
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 |
Array ( [id] => 3885 [inhibitor] => N-Arachidonylmaleimide [type] => Array ( [0] => Cannabinoid-Receptor-ligand ) [other_name] => Array ( [0] => CHEMBL561924 [1] => NAM [2] => N-Arachidonyl Maleimide [3] => SCHEMBL5086361 [4] => MolPort-019-939-191 ) [chemical_nomenclature] => 1-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenyl]pyrrole-2,5-dione [formula] => C24H35NO2 [cas_number] => 876305-42-9 [mw] => 369.54 [pick_me_to_call] => display_script [kinetic_parameter] => [paper] => Saario_2005_Chem.Biol_12_649 || Burston_2008_J.Pharmacol.Exp.Ther_327_546 || Zvonok_2008_Chem.Biol_15_854 [comment] => 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 [gene_locus] => human-MGLL [kin_inhibitor] => [cid] => 25021164 [family] => Monoglyceridelipase_lysophospholip [inchikey] => GZNZRHSGGQUYAP-DOFZRALJSA-N [canonicalsmiles] => 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- [wikipedia] => N-Arachidonylmaleimide [iupharlig] => [structure] => [substrate] => [interact_gene_locus] => [mutation] => [comment2] => [extoxnet] => [news] => [theoretical_model] => )