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Inhibitor Report for: Methyl-arachidonyl-fluorophosphonate

found also in complex with patatin-17 and fatty acid amide hydrolase (amidase superfamily) (MAFP) and related analogs have been shown to inhibit fatty acid amidohydrolase activity (FAAH)(not an alpha/beta hydrolase), the enzyme responsible for hydrolysis of the endogenous cannabinoid ligand anandamide. MAFP inhibits ABHD4. and PLA2G15 which are alpha/beta hydrolases (and also GIVA PLA2 not ABHyd)



General
Type: Cannabinoid-Receptor-ligand, Organophosphate, FAAH inhibitor, Multitarget
Chemical_Nomenclature: (5Z,8Z,11Z,14Z)-1-[fluoro(methoxy)phosphoryl]icosa-5,8,11,14-tetraene
Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCCP(=O)(OC)F
InChI: InChI=1S/C21H36FO2P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(22,23)24-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-21H2,1-2H3/b8-7-,11-10-,14-13-,17-16-
InChIKey: KWKZCGMJGHHOKJ-ZKWNWVNESA-N
Other name(s): MAFP ; Methyl arachidonyl fluorophosphonate ; CHEMBL113262 ; methyl (S)-(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-ylphosphonofluoridate
MW: 370.48
Formula: C21H36FO2P
CAS_number: 188404-10-6
PubChem: 10429254
IUPHAR:
Wikipedia:

Target families
Methyl-arachidonyl-fluorophosphonate ligand of proteins in family: CGI-58_ABHD5_ABHD4, PC-sterol_acyltransferase, Monoglyceridelipase_lysophospholip

Stucture of targets
4 structures (e.g. : 4X95, 4X93, 4X94... more)

Protein target

References
Search PubMed for references concerning: Methyl-arachidonyl-fluorophosphonate

8 more
    Title: Human leukocytes differentially express endocannabinoid-glycerol lipases and hydrolyze 2-arachidonoyl-glycerol and its metabolites from the 15-lipoxygenase and cyclooxygenase pathways
    Turcotte C, Dumais E, Archambault AS, Martin C, Blanchet MR, Bissonnette E, Boulet LP, Laviolette M, Di Marzo V, Flamand N
    Ref: J Leukoc Biol, 106:1337, 2019 : PubMed

            

    Title: Endocannabinoid biosynthesis proceeding through glycerophospho-N-acyl ethanolamine and a role for alpha/beta-hydrolase 4 in this pathway
    Simon GM, Cravatt BF
    Ref: Journal of Biological Chemistry, 281:26465, 2006 : PubMed

            

    Title: Cannabinoid properties of methylfluorophosphonate analogs
    Martin BR, Beletskaya I, Patrick G, Jefferson R, Winckler R, Deutsch DG, Di Marzo V, Dasse O, Mahadevan A, Razdan RK
    Ref: Journal of Pharmacology & Experimental Therapeutics, 294:1209, 2000 : PubMed