ouabain   Click here for help

GtoPdb Ligand ID: 4826

Approved drug PDB Ligand
ouabain is an approved drug
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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2D Structure
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Physico-chemical Properties
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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
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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
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Summary of Clinical Use Click here for help
Used in the treatment of atrial fibrillation, atrial flutter and heart failure. According to the US FDA International Drug Names listing, this drug is only available in Taiwan and Germany.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Inhibition of the cardiac Na+-K+-ATPase membrane pump, results in an increase in intracellular sodium and calcium concentrations. Increased intracellular calcium concentrations may be responsible for the activation of contractile proteins in the heart.