CHEBI:472805 - ouabain

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ChEBI Name ouabain
ChEBI ID CHEBI:472805
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44461, CHEBI:7805
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Formula C29H44O12
Net Charge 0
Average Mass 584.65250
Monoisotopic Mass 584.283
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
InChIKey LPMXVESGRSUGHW-HBYQJFLCSA-N
SMILES [H][C@@]12CC[C@]3(O)C[C@H](C[C@@H](O)[C@]3(CO)[C@@]1([H])[C@H](O)C[C@]1(C)[C@H](CC[C@]21O)C1=CC(=O)OC1)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
Metabolite of Species Details
Strophanthus gratus (NCBI:141614) See: PubMed
Roles Classification
Biological Role(s): EC 2.3.3.1 [citrate (Si)-synthase] inhibitor
An EC 2.3.3.* (acyltransferase converting acyl to alkyl group on transfer) inhibitor that interferes with the action of citrate (Si)-synthase, EC 2.3.3.1.
EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor
An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of 4-nitrophenylphosphatase (EC 3.1.3.41).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Na+/K+-transporting ATPase (EC 3.6.3.9).
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that inhibits H+/K+-exchanging ATPase, EC 3.6.3.10. Such compounds are also known as proton pump inhibitors.
ion transport inhibitor
A compound which inhibits the movement of an ion across an energy-transducing cell membrane.
hormone
Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
(via steroid hormone )
Application(s): cardiotonic drug
A drug that has a strengthening effect on the heart or that can increase cardiac output.
anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
(via cardiac glycoside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ouabain (CHEBI:472805) has role anti-arrhythmia drug (CHEBI:38070)
ouabain (CHEBI:472805) has role cardiotonic drug (CHEBI:38147)
ouabain (CHEBI:472805) has role EC 2.3.3.1 [citrate (Si)-synthase] inhibitor (CHEBI:77023)
ouabain (CHEBI:472805) has role EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor (CHEBI:77024)
ouabain (CHEBI:472805) has role EC 3.6.3.10 (H+/K+-exchanging ATPase) inhibitor (CHEBI:49200)
ouabain (CHEBI:472805) has role EC 3.6.3.9 (Na+/K+-transporting ATPase) inhibitor (CHEBI:63510)
ouabain (CHEBI:472805) has role ion transport inhibitor (CHEBI:50184)
ouabain (CHEBI:472805) has role plant metabolite (CHEBI:76924)
ouabain (CHEBI:472805) is a α-L-rhamnoside (CHEBI:27848)
ouabain (CHEBI:472805) is a 11α-hydroxy steroid (CHEBI:19129)
ouabain (CHEBI:472805) is a 14β-hydroxy steroid (CHEBI:36862)
ouabain (CHEBI:472805) is a 5β-hydroxy steroid (CHEBI:38195)
ouabain (CHEBI:472805) is a cardenolide glycoside (CHEBI:38092)
ouabain (CHEBI:472805) is a steroid hormone (CHEBI:26764)
IUPAC Name
3-(6-deoxy-α-L-mannopyranosyloxy)-1β,5β,11α,14,19-pentahydroxy-5β-card-20(22)-enolide
Synonyms Sources
3-(α-L-rhamnopyranosyloxy)-1β,5β,11α,14,19-pentahydroxy-5β-card-20(22)-enolide IUPAC
G-Strophanthin KEGG COMPOUND
Ouabagenin L-Rhamnoside DrugBank
Ouabagenin-L-rhamnosid ChemIDplus
Ouabain KEGG COMPOUND
Ouabain anhydrous ChemIDplus
Ouabaine ChemIDplus
Oubain ChemIDplus
Brand Name Source
Strodival ChemIDplus
Database Links Databases
C00003633 KNApSAcK
C01443 KEGG COMPOUND
D00112 KEGG DRUG
DB01092 DrugBank
HMDB15224 HMDB
LMST01120022 LIPID MAPS
LSM-2781 LINCS
OBN PDBeChem
Ouabain Wikipedia
View more database links
Registry Numbers Types Sources
101712 Beilstein Registry Number Beilstein
101712 Reaxys Registry Number Reaxys
630-60-4 CAS Registry Number KEGG COMPOUND
630-60-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10438974 PubMed citation Europe PMC
1316269 PubMed citation Europe PMC
16529963 PubMed citation Europe PMC
20372980 PubMed citation Europe PMC
9872395 PubMed citation Europe PMC
Last Modified
25 February 2016