Methoxy arachidonyl fluorophosphonate

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Methoxy arachidonyl fluorophosphonate
Mafp.png
Names
IUPAC name
methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14- tetraenylphosphonofluoridate
Other names
MAFP
Identifiers
ChEMBL ChEMBL113262 YesY
ChemSpider 8604682 YesY
Jmol 3D model Interactive image
PubChem 10429254
  • 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- YesY
    Key: KWKZCGMJGHHOKJ-ZKWNWVNESA-N YesY
  • 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
  • FP(=O)(OC)CCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
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).
YesY verify (what is YesYN ?)
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.[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]

See also

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

References

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