4-Nonylphenylboronic acid

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 100nM and 1400nM respectively.[2]

4-Nonylphenylboronic acid

Clinical data
ATC code	None
Identifiers
IUPAC name 4-Nonylphenylboronic acid
CAS Number	256383-45-6
PubChem CID	4589192
ChemSpider	3781380
CompTox Dashboard (EPA)	DTXSID10404611
Chemical and physical data
Formula	C15H25BO2
Molar mass	248.17 g·mol^−1
3D model (JSmol)	Interactive image
SMILES OB(O)C1=CC=C(CCCCCCCCC)C=C1
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

See also

• IDFP
• LY-2183240
• URB-597

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.