4-Nonylphenylboronic acid

4-Nonylphenylboronic acid
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 4-Nonylphenylboronic acid
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H25BO2
Molar mass248.17 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCCCCCc1ccc(B(O)O)cc1
InChI
  • InChI=1S/C15H25BO2/c1-2-3-4-5-6-7-8-9-14-10-12-15(13-11-14)16(17)18/h10-13,17-18H,2-9H2,1H3
  • Key:VONVJOGSLHAKOX-UHFFFAOYSA-N

4-Nonylphenylboronic acid is a potent and selective inhibitor of the enzyme fatty acid amide hydrolase (FAAH), with an IC50 of 9.1nM, and 870x selectivity for FAAH over the related enzyme MAGL, which it inhibits with an IC50 of 7900nM.[1] It is also a weaker inhibitor of the enzymes endothelial lipase and lipoprotein lipase, with IC50 values of 100 nM and 1400 nM respectively.[2]

See also

References

  1. ↑ Minkkilä A, Saario SM, Käsnänen H, Leppänen J, Poso A, Nevalainen T (November 2008). "Discovery of boronic acids as novel and potent inhibitors of fatty acid amide hydrolase". Journal of Medicinal Chemistry. 51 (22): 7057–60. doi:10.1021/jm801051t. PMID 18983140.
  2. ↑ O'Connell DP, LeBlanc DF, Cromley D, Billheimer J, Rader DJ, Bachovchin WW (February 2012). "Design and synthesis of boronic acid inhibitors of endothelial lipase". Bioorganic & Medicinal Chemistry Letters. 22 (3): 1397–401. doi:10.1016/j.bmcl.2011.12.043. PMID 22225633.
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