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CHEBI:472805 - ouabain
| Formula | C29H44O12 |
| Net Charge | 0 |
| Average Mass | 584.659 |
| Monoisotopic Mass | 584.28328 |
| 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 |
| 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 |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Strophanthus gratus (ncbitaxon:141614) | - | PubMed (14311759) |
| Roles Classification |
|---|
| Biological Roles: | 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). 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). ion transport inhibitor A compound which inhibits the movement of an ion across an energy-transducing cell membrane. 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 3.6.3.10 (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. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. 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. |
| Applications: | 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. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| 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 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) |
| ouabain (CHEBI:472805) is a α-L-rhamnoside (CHEBI:27848) |
| ouabain (CHEBI:472805) is conjugate acid of ouabain(1−) (CHEBI:145798) |
| Incoming Relation(s) |
| dihydroouabain (CHEBI:131146) has functional parent ouabain (CHEBI:472805) |
| ouabain(1−) (CHEBI:145798) is conjugate base of ouabain (CHEBI:472805) |
| IUPAC Name |
|---|
| 3-(6-deoxy-α-L-mannopyranosyloxy)-1β,5β,11α,14,19-pentahydroxy-5β-card-20(22)-enolide |
| Synonyms | Source |
|---|---|
| Ouabain | KEGG COMPOUND |
| G-Strophanthin | KEGG COMPOUND |
| Ouabagenin L-Rhamnoside | DrugBank |
| Ouabaine | ChemIDplus |
| Oubain | ChemIDplus |
| Ouabain anhydrous | ChemIDplus |
| Brand Name | Source |
|---|---|
| Strodival | ChemIDplus |
| Registry Numbers | Sources |
|---|---|
| Beilstein:101712 | Beilstein |
| Reaxys:101712 | Reaxys |
| CAS:630-60-4 | KEGG COMPOUND |
| CAS:630-60-4 | ChemIDplus |
| Citations |
|---|