Chemical Component Summary

NameMETHYL ARACHIDONYL FLUOROPHOSPHONATE
SynonymsMAFP
Identifiers(5Z,8Z,11Z,14Z)-1-[fluoro(methoxy)phosphoryl]icosa-5,8,11,14-tetraene
FormulaC21 H36 F O2 P
Molecular Weight370.482
TypeNON-POLYMER
Isomeric SMILESCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC[P@](=O)(OC)F
InChIInChI=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-/t25-/m0/s1
InChIKeyKWKZCGMJGHHOKJ-WTIHWRCNSA-N

Chemical Details

Formal Charge0
Atom Count61
Chiral Atom Count1
Bond Count60
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB02465 
NameMethoxy arachidonyl fluorophosphonate
Groups experimental
DescriptionMethoxy arachidonyl fluorophosphonate, commonly referred as MAFP, is an irreversible active site-directed enzyme inhibitor that inhibits nearly all serine hydrolases and serine proteases. It inhibits phospholipase A2 and fatty acid amide hydrolase with special potency, displaying IC50 values in the low-nanomolar range.
Synonyms
  • MAFP
  • Methoxy arachidonyl fluorophosphonate
  • Methyl arachidonylfluorophosphonate
Categories
  • Eicosanoids
  • Enzyme Inhibitors
  • Fatty Acids
  • Fatty Acids, Essential
  • Fatty Acids, Unsaturated
CAS number180509-15-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Fatty-acid amide hydrolase 1MVQYELWAALPGASGVALACCFVAAAVALRWSGRRTARGAVVRARQRQRA...unknown
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 92536013