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
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
Jmol-3D images	Image
PubChem	10429254
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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.

See also

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

References

1. ↑ Hoover HS, Blankman JL, Niessen S, Cravatt BF (July 2008). "Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling". Bioorg. Med. Chem. Lett. 18 (22): 5838–41. doi:10.1016/j.bmcl.2008.06.091. PMC 2634297. PMID 18657971.