Methoxy arachidonyl fluorophosphonate

Methoxy arachidonyl fluorophosphonate

IUPAC name methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14- tetraenylphosphonofluoridate
Other names MAFP
Identifiers
PubChem	10429254
ChemSpider	8604682^Y
ChEMBL	CHEMBL113262^Y
Jmol-3D images	Image 1
SMILES FP(=O)(OC)CCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
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
Properties
Molecular formula	C₂₁H₃₆FO₂P
Molar mass	370.5
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

References