brophenexin   Click here for help

GtoPdb Ligand ID: 13601

Synonyms: compound 8 [PMID: 33033186] | NMDAR/TRPM4 inhibitor 8
Compound class: Synthetic organic
Comment: Brophenexin is a prototype small molecule that acts to disrupt the interaction between NMDA glutamate receptors (NMDAR) and transient receptor potential cation channel subfamily M member 4 (TRPM4) [2]. In extrasynaptic neurons the NMDAR subunits GluN2A and GluN2B interact with the TwinF domain of TRPM4, to form a NMDAR/TRPM4 death signaling complex that mediates NMDA-triggered toxicity and neurodegeneration. This new class of agents have been named collectively as TwinF interface (TI) inhibitors and they are being explored for anti-neurodegenerative/neuroprotective effects [1]. Brophenexin does not alter NMDA-induced calcium signals or NMDAR-mediated inward currents, calcium-activated TRPM4 channel activity, or expression of either protein [2]. Experimental evidence indicates that it acts only as a protein-protein interaction inhibitor.

brophenexin is commercially available from our sponsors

2D Structure
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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.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 29.26
Molecular weight 257.17
XLogP 0.92
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCN(CCN)CC1=CC=CC(=C1)Br
Isomeric SMILES BrC=1C=C(C=CC1)CN(CCN)CC
InChI InChI=1S/C11H17BrN2/c1-2-14(7-6-13)9-10-4-3-5-11(12)8-10/h3-5,8H,2,6-7,9,13H2,1H3
InChI Key XSMDMHAMGOGFLG-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N'-[(3-bromophenyl)methyl]-N'-ethylethane-1,2-diamine
Synonyms Click here for help
compound 8 [PMID: 33033186] | NMDAR/TRPM4 inhibitor 8
Database Links Click here for help
GtoPdb PubChem SID 504705420
PubChem CID 66568274
Search Google for chemical match using the InChIKey XSMDMHAMGOGFLG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XSMDMHAMGOGFLG
UniChem Compound Search for chemical match using the InChIKey XSMDMHAMGOGFLG-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XSMDMHAMGOGFLG-UHFFFAOYSA-N

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MedChemExpress
Brophenexin free base (links to external site)
Cat. No. HY-139192A