tubocurarine   Click here for help

GtoPdb Ligand ID: 2294

Synonyms: (+)-tubocurarine | d-tubocurarine
Approved drug
tubocurarine is an approved drug (FDA (1945))
Compound class: Natural product or derivative
Comment: Tubocurarine is a skeletal muscle relaxant. The structure as specified by the FDA and the INN document shows the compound in complex with chloride (see PubChem CID 9917490). As our data specifies the parent compound, it is this structure we have chosen to display here, and which the majority of entries linked to from the table above display.
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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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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 1
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 80.62
Molecular weight 609.3
XLogP 4.66
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 COc1cc2CCN(C3c2cc1Oc1cc(ccc1O)CC1c2c(CC[N+]1(C)C)cc(c(c2Oc1ccc(C3)cc1)O)OC)C
Isomeric SMILES COc1cc2CCN([C@@H]3c2cc1Oc1cc(ccc1O)C[C@@H]1c2c(CC[N+]1(C)C)cc(c(c2Oc1ccc(C3)cc1)O)OC)C
InChI InChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(43-5)36(37)41)13-15-39(2,3)29(35)17-23-8-11-30(40)31(18-23)45-33/h6-11,18-21,28-29H,12-17H2,1-5H3,(H-,40,41)/p+1/t28-,29+/m0/s1
InChI Key JFJZZMVDLULRGK-URLMMPGGSA-O
No information available.
Summary of Clinical Use Click here for help
Historically used adjunctively in anaesthesia to provide skeletal muscle relaxation during surgery or mechanical ventilation. All formulations of this drug formerly approved by the US FDA appear to have been discontinued. Other national approval agencies may have granted marketing authorisation. Newer and improved drugs are now available.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Tubocurarine is a long-acting antagonist of muscle-type nicotinic acetylcholine receptors (subunit composition (α1)2β1δε or (α1)2β1δγ) [12]). Full details of the subunits are available via the Nicotinic acetylcholine receptors page of this website.