ouabain   

GtoPdb Ligand ID: 4826

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.
2D Structure
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Physico-chemical Properties
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
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
Compound class Natural product or derivative
Approved drug? Yes
IUPAC Name
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
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
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Search UniChem for chemical match using the InChIKey LPMXVESGRSUGHW-HBYQJFLCSA-N
Search UniChem for chemicals with the same backbone LPMXVESGRSUGHW
Wikipedia Ouabain

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Tocris
Ouabain
Cat. No. 1076