2-APB   Click here for help

GtoPdb Ligand ID: 2433

Synonyms: 2-aminoethoxydiphenyl borate | 2-aminoethoxydiphenylborane
PDB Ligand
Compound class: Synthetic organic
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

2-APB is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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
InChI Key BLZVCIGGICSWIG-UHFFFAOYSA-N
References
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]