betahistine   Click here for help

GtoPdb Ligand ID: 11937

Synonyms: OBE101 [2] | SERC® | Vasomotal®
Approved drug
betahistine is an approved drug (FDA (1970s))
Compound class: Synthetic organic
Comment: This is an orally delivered histamine receptor modulator that has weak agonist activity at histamine H1 receptors and more potent antagonist activity at the H3 receptor subtype [1].
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 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.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 24.92
Molecular weight 136.1
XLogP 0.53
No. Lipinski's rules broken 0
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.

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Canonical SMILES CNCCc1ccccn1
Isomeric SMILES CNCCc1ccccn1
InChI InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3
InChI Key UUQMNUMQCIQDMZ-UHFFFAOYSA-N
References
1. Fossati A, Barone D, Benvenuti C. (2001)
Binding affinity profile of betahistine and its metabolites for central histamine receptors of rodents.
Pharmacol Res, 43 (4): 389-92. [PMID:11352543]
2. Pierson PD, Fettes A, Freichel C, Gatti-McArthur S, Hertel C, Huwyler J, Mohr P, Nakagawa T, Nettekoven M, Plancher JM et al.. (2009)
5-hydroxyindole-2-carboxylic acid amides: novel histamine-3 receptor inverse agonists for the treatment of obesity.
J Med Chem, 52 (13): 3855-68. [PMID:19456097]