ouabain   Click here for help

GtoPdb Ligand ID: 4826

Approved drug PDB Ligand
ouabain is an approved drug
Compound class: Natural product or derivative
Comment: Ouabain is a plant derived toxin. It is classified as a cardiac glycoside drug, although due to its high level of toxicity it is generally only used experimentally.
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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

ouabain 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 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 12
Hydrogen bond donors 8
Rotatable bonds 4
Topological polar surface area 206.6
Molecular weight 584.28
XLogP -0.81
No. Lipinski's rules broken 2
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 OCC12C(O)CC(CC2(O)CCC2C1C(O)CC1(C2(O)CCC1C1=CC(=O)OC1)C)OC1OC(C)C(C(C1O)O)O
Isomeric SMILES OC[C@@]12[C@H](O)C[C@@H](C[C@@]2(O)CC[C@@H]2[C@@H]1[C@H](O)C[C@]1([C@]2(O)CC[C@@H]1C1=CC(=O)OC1)C)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1
InChI Key LPMXVESGRSUGHW-HBYQJFLCSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes
IUPAC Name Click here for help
4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9684082
Reactome Reaction Reactome logo R-HSA-9684068
Other databases
CAS Registry No. 630-60-4 (source: Scifinder)
ChEBI CHEBI:472805
ChEMBL Ligand CHEMBL222863
DrugBank Ligand DB01092
DrugCentral Ligand 2004
GtoPdb PubChem SID 178101528
PubChem CID 439501
RCSB PDB Ligand OBN
Search Google for chemical match using the InChIKey LPMXVESGRSUGHW-HBYQJFLCSA-N
Search Google for chemicals with the same backbone LPMXVESGRSUGHW
UniChem Compound Search for chemical match using the InChIKey LPMXVESGRSUGHW-HBYQJFLCSA-N
UniChem Connectivity Search for chemical match using the InChIKey LPMXVESGRSUGHW-HBYQJFLCSA-N
Wikipedia Ouabain

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Tocris
Ouabain (links to external site)
Cat. No. 1076