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
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 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 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

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 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

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/)
Bioactivity Comments
Due to the complex and varied nature of the precise subunit composition of nACh channels, and a paucity of affinity data with definitive molecular details, we have not tagged a primary target for this drug.
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Organic cation transporter 2 4
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT3A Mm Antagonist Antagonist 6.6 – 7.1 pKi - 1,14
⤷ pKi 6.6 – 7.1 [1,14]
5-HT3A Hs Antagonist Antagonist 4.8 pKi - 2,5
⤷ pKi 4.8 [2,5]
5-HT3AB Hs Antagonist Antagonist 4.5 pKi - 2
⤷ pKi 4.5 [2]
KCa2.2 Hs Channel blocker Antagonist 5.7 pIC50 - 7
⤷ pIC50 5.7 [7]
KCa2.2 Rn Channel blocker Antagonist 4.8 – 5.6 pIC50 - 6,8,10
⤷ pIC50 4.8 – 5.6 [6,8,10]
ZAC Hs Antagonist Antagonist 5.2 pIC50 - 3
⤷ pIC50 5.2 (IC50 6.3x10-6 M) [3]
KCa2.1 Hs Channel blocker Antagonist 4.1 – 4.6 pIC50 - 8-10
⤷ pIC50 4.1 – 4.6 (IC50 8x10-5 – 2.5x10-5 M) [8-10]
Voltage: -100.0 – 80.0 mV
KCa2.3 Hs Channel blocker Antagonist 3.7 – 4.5 pIC50 - 11,13
⤷ pIC50 3.7 – 4.5 [11,13]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Commonly used antagonists at nicotinic acetylcholine receptor α2 subunit α2β2: DHβE (KB = 0.9 μM), tubocurarine (KB = 1.4 μM); α2β4: DHβE (KB = 3.6 μM), tubocurarine (KB = 4.2 μM)
Commonly used antagonists at nicotinic acetylcholine receptor α3 subunit α3β2: DHβE (KB = 1.6 μM, IC50 = 2.0 μM), tubocurarine (KB = 2.4 μM); α3β4: DHβE (KB = 19 μM, IC50 = 26 μM), tubocurarine (KB = 2.2 μM)
Commonly used antagonists at nicotinic acetylcholine receptor α8 subunit (avian) (α8)5: α-bungarotoxin > atropine ≥ tubocurarine ≥ strychnine
Commonly used antagonists at nicotinic acetylcholine receptor α4 subunit α4β2: DHβE (KB = 0.1 μM; IC50 = 0.08 - 0.9 μM), tubocurarine (KB = 3.2 μM, IC50 = 34 μM); α4β4: DHβE (KB = 0.01 μM, IC50 = 0.19 – 1.2 μM), tubocurarine (KB = 0.2 μM, IC50 = 50 μM)
Commonly used antagonists at nicotinic acetylcholine receptor α9 subunit (α9)5: α-bungarotoxin > methyllycaconitine > strychnine ~ tropisetron > tubocurarine; α9α10: α-bungarotoxin > tropisetron = strychnine > tubocurarine
Commonly used antagonists at nicotinic acetylcholine receptor α10 subunit α9α10: α-bungarotoxin > tropisetron = strychnine > tubocurarine
Commonly used antagonists at nicotinic acetylcholine receptor α7 subunit (α7)5: DHβE (IC50 = 8 - 20 μM); (α7)5: tubocurarine (IC50 = 3.1 μM)
Commonly used antagonists at nicotinic acetylcholine receptor α1 subunit (α1)2β1γδ and (α1)2β1δε: α-bungarotoxin > pancuronium > vecuronium > rocuronium > tubocurarine (IC50 = 43 - 82 nM)
Ligand mentioned in the following text fields
ZAC overview
ZAC comments