2-APB   Click here for help

GtoPdb Ligand ID: 2433

Synonyms: 2-aminoethoxydiphenyl borate | 2-aminoethoxydiphenylborane
PDB Ligand
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 35.25
Molecular weight 225.13
XLogP 3.24
No. Lipinski's rules broken 0
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Canonical SMILES NCCOB(c1ccccc1)c1ccccc1
Isomeric SMILES NCCOB(c1ccccc1)c1ccccc1
InChI InChI=1S/C14H16BNO/c16-11-12-17-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,11-12,16H2
1. Broertjes J, Klarenbeek J, Habani Y, Langeslag M, Jalink K. (2019)
TRPM7 residue S1269 mediates cAMP dependence of Ca2+ influx.
PLoS ONE, 14 (1): e0209563. [PMID:30615643]
2. Chung MK, Lee H, Mizuno A, Suzuki M, Caterina MJ. (2004)
2-aminoethoxydiphenyl borate activates and sensitizes the heat-gated ion channel TRPV3.
J Neurosci, 24 (22): 5177-82. [PMID:15175387]
3. Hu HZ, Gu Q, Wang C, Colton CK, Tang J, Kinoshita-Kawada M, Lee LY, Wood JD, Zhu MX. (2004)
2-aminoethoxydiphenyl borate is a common activator of TRPV1, TRPV2, and TRPV3.
J Biol Chem, 279 (34): 35741-8. [PMID:15194687]
4. Juvin V, Penna A, Chemin J, Lin YL, Rassendren FA. (2007)
Pharmacological characterization and molecular determinants of the activation of transient receptor potential V2 channel orthologs by 2-aminoethoxydiphenyl borate.
Mol Pharmacol, 72 (5): 1258-68. [PMID:17673572]
5. Li M, Jiang J, Yue L. (2006)
Functional characterization of homo- and heteromeric channel kinases TRPM6 and TRPM7.
J Gen Physiol, 127 (5): 525-37. [PMID:16636202]
6. Lievremont JP, Bird GS, Putney Jr JW. (2005)
Mechanism of inhibition of TRPC cation channels by 2-aminoethoxydiphenylborane.
Mol Pharmacol, 68 (3): 758-62. [PMID:15933213]
7. Lucas P, Ukhanov K, Leinders-Zufall T, Zufall F. (2003)
A diacylglycerol-gated cation channel in vomeronasal neuron dendrites is impaired in TRPC2 mutant mice: mechanism of pheromone transduction.
Neuron, 40 (3): 551-61. [PMID:14642279]
8. Naziroğlu M, Ozgül C. (2012)
Effects of antagonists and heat on TRPM8 channel currents in dorsal root ganglion neuron activated by nociceptive cold stress and menthol.
Neurochem Res, 37 (2): 314-20. [PMID:21964764]
9. Neeper MP, Liu Y, Hutchinson TL, Wang Y, Flores CM, Qin N. (2007)
Activation properties of heterologously expressed mammalian TRPV2: evidence for species dependence.
J Biol Chem, 282 (21): 15894-902. [PMID:17395593]
10. Qin N, Neeper MP, Liu Y, Hutchinson TL, Lubin ML, Flores CM. (2008)
TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons.
J Neurosci, 28 (24): 6231-8. [PMID:18550765]
11. Strübing C, Krapivinsky G, Krapivinsky L, Clapham DE. (2001)
TRPC1 and TRPC5 form a novel cation channel in mammalian brain.
Neuron, 29 (3): 645-55. [PMID:11301024]
12. Togashi K, Inada H, Tominaga M. (2008)
Inhibition of the transient receptor potential cation channel TRPM2 by 2-aminoethoxydiphenyl borate (2-APB).
Br J Pharmacol, 153 (6): 1324-30. [PMID:18204483]
13. Xu SZ, Zeng F, Boulay G, Grimm C, Harteneck C, Beech DJ. (2005)
Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect.
Br J Pharmacol, 145 (4): 405-14. [PMID:15806115]
14. Zierler S, Yao G, Zhang Z, Kuo WC, Pörzgen P, Penner R, Horgen FD, Fleig A. (2011)
Waixenicin A inhibits cell proliferation through magnesium-dependent block of transient receptor potential melastatin 7 (TRPM7) channels.
J Biol Chem, 286 (45): 39328-35. [PMID:21926172]