CHEBI:131146 - dihydroouabain

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ChEBI Name dihydroouabain
ChEBI ID CHEBI:131146
Definition A cardenolide glycoside that is ouabain in which the double bond in the lactone ring has been reduced to a single bond. It is a cardiac glycoside and a derivative of ouabain which is used as a sodium pump antagonist and exhibits ionotropic effects.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H46O12
Net Charge 0
Average Mass 586.675
Monoisotopic Mass 586.29893
InChI InChI=1S/C29H46O12/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/h13-19,21-25,30-32,34-38H,3-12H2,1-2H3/t13-,14?,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1
InChIKey ZTFGOPUOTATSAL-CFVDWFIMSA-N
SMILES [H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4(O)C[C@H](C[C@@H](O)[C@]4(CO)[C@@]3([H])[C@H](O)C[C@]12C)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C1COC(=O)C1
Roles Classification
Biological Role(s): 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).
Application(s): radiosensitizing agent
A drug that makes increases the sensitivity of tumour cells to radiation therapy.
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 dihydroouabain (CHEBI:131146) has functional parent ouabain (CHEBI:472805)
dihydroouabain (CHEBI:131146) has role EC 3.6.3.9 (Na+/K+-transporting ATPase) inhibitor (CHEBI:63510)
dihydroouabain (CHEBI:131146) has role radiosensitizing agent (CHEBI:132992)
dihydroouabain (CHEBI:131146) is a cardenolide glycoside (CHEBI:38092)
IUPAC Name
(20ξ)-3β-[(6-deoxy-α-L-mannopyranosyl)oxy]-1β,5,11α,14,19-pentahydroxy-5β-cardanolide
Synonyms Sources
(1β,3β,5β,11α,20ξ)-3-[(6-deoxy-α-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxycardanolide ChEBI
3β-[(6-deoxy-α-L-mannopyranosyl)oxy]-1β,5,11α,14,19-pentahydroxy-5β,20ξ-cardanolide ChEBI
dihydro-g-strophanthin ChemIDplus
dihydroouabain UniProt
Manual Xrefs Databases
HMDB0251322 HMDB
LSM-42697 LINCS
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Registry Numbers Types Sources
1183-35-3 CAS Registry Number ChemIDplus
71786 Reaxys Registry Number Reaxys
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Last Modified
18 May 2023