:4-Nonylphenylboronic acid

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 4-Nonylphenylboronic acid

| image = 4-Nonylphenylboronic acid Structure.svg

| width = 280

| CAS_number = 256383-45-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2SY8DS7Y3D

| ChEMBL =

| ATC_prefix = None

| ATC_suffix =

| PubChem = 4589192

| ChemSpiderID = 3781380

| C=15 | H=25 | B=1 | O=2

| smiles = CCCCCCCCCc1ccc(B(O)O)cc1

| StdInChI = 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

| StdInChIKey = VONVJOGSLHAKOX-UHFFFAOYSA-N

| bioavailability =

| protein_bound =

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}}

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.{{cite journal | vauthors = Minkkilä A, Saario SM, Käsnänen H, Leppänen J, Poso A, Nevalainen T | title = Discovery of boronic acids as novel and potent inhibitors of fatty acid amide hydrolase | journal = Journal of Medicinal Chemistry | volume = 51 | issue = 22 | pages = 7057–60 | date = November 2008 | pmid = 18983140 | doi = 10.1021/jm801051t }} It is also a weaker inhibitor of the enzymes endothelial lipase and lipoprotein lipase, with {{IC50}} values of 100 nM and 1400 nM respectively.{{cite journal | vauthors = O'Connell DP, LeBlanc DF, Cromley D, Billheimer J, Rader DJ, Bachovchin WW | title = Design and synthesis of boronic acid inhibitors of endothelial lipase | journal = Bioorganic & Medicinal Chemistry Letters | volume = 22 | issue = 3 | pages = 1397–401 | date = February 2012 | pmid = 22225633 | doi = 10.1016/j.bmcl.2011.12.043 }}