Methoxy arachidonyl fluorophosphonate

Methoxy arachidonyl fluorophosphonate

Names
IUPAC name methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14- tetraenylphosphonofluoridate
Other names MAFP
Identifiers
ChEMBL	ChEMBL113262 Y
ChemSpider	8604682 Y
Jmol 3D model	Interactive image
PubChem	10429254
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- Y Key: KWKZCGMJGHHOKJ-ZKWNWVNESA-N Y InChI=1/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- Key: KWKZCGMJGHHOKJ-ZKWNWVNEBX
SMILES FP(=O)(OC)CCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
Chemical formula	C21H36FO2P
Molar mass	370.5
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Methyl 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. In addition, it binds to the CB₁ receptor in rat brain membrane preparations (IC₅₀ = 20 nM), but does not appear to agonize or antagonize the receptor.

See also

• DIFP - diisopropyl fluorophosphate, a related inhibitor
• IDFP - isopropyl dodecylfluorophosphonate, another related inhibitor with selectivity for FAAH and MAGL
• Activity based probes