Methoxy arachidonyl fluorophosphonate

Methoxy arachidonyl fluorophosphonate, commonly referred as MAFP, is an irreversible active site-directed enzyme inhibitor that inhibits nearly all serine hydrolases and serine proteases.^[1] 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),^[2] but does not appear to agonize or antagonize the receptor,^[3] though some related derivatives do show cannabinoid-like properties.^[4]

Methoxy arachidonyl fluorophosphonate

Names
Preferred IUPAC name Methyl [(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yl]phosphonofluoridate
Other names MAFP
Identifiers
CAS Number	188404-10-6 N[ChemSpider]
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL113262 Y
ChemSpider	8604682 Y
EC Number	201-185-2
PubChem CID	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
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
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

See also

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