4-Nonylphenylboronic acid: Difference between revisions
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{{Short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| IUPAC_name = 4-Nonylphenylboronic acid |
| IUPAC_name = 4-Nonylphenylboronic acid |
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| image = 4- |
| image = 4-Nonylphenylboronic acid Structure.svg |
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| width = 280 |
| width = 280 |
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| CAS_number = 256383-45-6 |
| CAS_number = 256383-45-6 |
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| ChEMBL = |
| ChEMBL = |
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| ATC_prefix = None |
| ATC_prefix = None |
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| ATC_suffix = |
| ATC_suffix = |
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| PubChem = |
| PubChem = 4589192 |
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| ChemSpiderID |
| ChemSpiderID = 3781380 |
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| C=15 | H=25 | B=1 | O=2 |
| C=15 | H=25 | B=1 | O=2 |
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| molecular_weight = 248.17 g/mol |
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| 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 |
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| StdInChIKey = VONVJOGSLHAKOX-UHFFFAOYSA-N |
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| bioavailability = |
| bioavailability = |
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| protein_bound = |
| 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 IC<sub>50</sub> of 9.1nM, and 870x selectivity for FAAH over the related enzyme MAGL, which it inhibits with an IC<sub>50</sub> of 7900nM.<ref>{{ |
'''4-Nonylphenylboronic acid''' is a potent and selective inhibitor of the enzyme [[fatty acid amide hydrolase]] (FAAH), with an IC<sub>50</sub> of 9.1nM, and 870x selectivity for FAAH over the related enzyme [[Monoacylglycerol lipase|MAGL]], which it inhibits with an IC<sub>50</sub> of 7900nM.<ref>{{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 }}</ref> It is also a weaker inhibitor of the enzymes [[endothelial lipase]] and [[lipoprotein lipase]], with {{IC50}} values of 100 nM and 1400 nM respectively.<ref>{{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 }}</ref> |
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==See also== |
== See also == |
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* [[IDFP]] |
* [[IDFP]] |
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* [[LY-2183240]] |
* [[LY-2183240]] |
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* [[URB-597]] |
* [[URB-597]] |
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==References== |
== References == |
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{{reflist}} |
{{reflist}} |
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{{Cannabinoids}} |
{{Cannabinoids}} |
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{{DEFAULTSORT:Nonylphenylboronic acid, 4-}} |
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[[Category:Enzyme inhibitors]] |
[[Category:Enzyme inhibitors]] |
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[[Category:Boronic acids]] |
Latest revision as of 11:39, 23 January 2023
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Chemical and physical data | |
Formula | C15H25BO2 |
Molar mass | 248.17 g·mol−1 |
3D model (JSmol) | |
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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.[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
[edit]References
[edit]- ^ 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.
- ^ 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.