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CHEBI:472805 - ouabain

ChEBI IDCHEBI:472805
ChEBI Nameouabain
Stars
DefinitionA steroid hormone that is a multi-hydroxylated α-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na+/K+-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus .
Secondary ChEBI IDsCHEBI:7805, CHEBI:44461
Last Modified5 November 2021
DownloadsMolfile

FormulaC29H44O12
Net Charge0
Average Mass584.659
Monoisotopic Mass584.28328
SMILES[H][C@@]12CC[C@]3(O)C[C@@H](O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)C[C@@H](O)[C@]3(CO)[C@@]1([H])[C@H](O)C[C@]1(C)[C@@H](C3=CC(=O)OC3)CC[C@]21O
InChIInChI=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
InChIKeyLPMXVESGRSUGHW-HBYQJFLCSA-N

Wikipedia
Species of MetaboliteComponentSourceComments
Strophanthus gratus (ncbitaxon:141614) - PubMed (14311759)
Roles Classification

ChEBI Ontology
IUPAC Name 
3-(6-deoxy-α-L-mannopyranosyloxy)-1β,5β,11α,14,19-pentahydroxy-5β-card-20(22)-enolide
Synonyms  Source
OuabainKEGG COMPOUND
G-StrophanthinKEGG COMPOUND
Ouabagenin L-RhamnosideDrugBank
OuabaineChemIDplus
OubainChemIDplus
Ouabain anhydrousChemIDplus
Brand Name  Source
StrodivalChemIDplus
Manual XrefsDatabases
C01443KEGG COMPOUND
OBNPDBeChem
DB01092DrugBank
D00112KEGG DRUG
LMST01120022LIPID MAPS
HMDB0015224HMDB
OuabainWikipedia
C00003633KNApSAcK
LSM-2781LINCS
2004DrugCentral
FDB005482FooDB
Registry NumbersSources
Beilstein:101712Beilstein
Reaxys:101712Reaxys
CAS:630-60-4KEGG COMPOUND
CAS:630-60-4ChemIDplus
Citations