gallamine   Click here for help

GtoPdb Ligand ID: 356

Synonyms: Flaxedil®
Approved drug PDB Ligand
gallamine is an approved drug
Compound class: Synthetic organic
Comment: The approved drug contains three iodine ions and is called gallamine triethiodide. This drug is known as a nondepolarizing neuromuscular blocking drug (NDMRD).
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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.

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View interactive charts of activity data across species
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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Click here for structure editor
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 0
Hydrogen bond donors 0
Rotatable bonds 21
Topological polar surface area 27.69
Molecular weight 510.46
XLogP 4.29
No. Lipinski's rules broken 1
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 CC[N+](CCOc1c(OCC[N+](CC)(CC)CC)cccc1OCC[N+](CC)(CC)CC)(CC)CC
Isomeric SMILES CC[N+](CCOc1c(OCC[N+](CC)(CC)CC)cccc1OCC[N+](CC)(CC)CC)(CC)CC
InChI InChI=1S/C30H60N3O3/c1-10-31(11-2,12-3)22-25-34-28-20-19-21-29(35-26-23-32(13-4,14-5)15-6)30(28)36-27-24-33(16-7,17-8)18-9/h19-21H,10-18,22-27H2,1-9H3/q+3
InChI Key OZLPUNFFCJDMJD-UHFFFAOYSA-N
References
1. Clark AL, Mitchelson F. (1976)
The inhibitory effect of gallamine on muscarinic receptors.
Br J Pharmacol, 58 (3): 323-31. [PMID:990587]
2. Kovacs I, Yamamura HI, Waite SL, Varga EV, Roeske WR. (1998)
Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line.
J Pharmacol Exp Ther, 284 (2): 500-7. [PMID:9454790]
3. Lazareno S, Birdsall NJ. (1995)
Detection, quantitation, and verification of allosteric interactions of agents with labeled and unlabeled ligands at G protein-coupled receptors: interactions of strychnine and acetylcholine at muscarinic receptors.
Mol Pharmacol, 48 (2): 362-78. [PMID:7651370]
4. Moo EV, Sexton PM, Christopoulos A, Valant C. (2018)
Utility of an "Allosteric Site-Impaired" M2 Muscarinic Acetylcholine Receptor as a Novel Construct for Validating Mechanisms of Action of Synthetic and Putative Endogenous Allosteric Modulators.
Mol Pharmacol, 94 (5): 1298-1309. [PMID:30213802]
5. Tränkle C, Weyand O, Voigtländer U, Mynett A, Lazareno S, Birdsall NJ, Mohr K. (2003)
Interactions of orthosteric and allosteric ligands with [3H]dimethyl-W84 at the common allosteric site of muscarinic M2 receptors.
Mol Pharmacol, 64 (1): 180-90. [PMID:12815174]