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CHEBI:131146 - dihydroouabain

ChEBI IDCHEBI:131146
ChEBI Namedihydroouabain
Stars
DefinitionA 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.
Last Modified18 May 2023
DownloadsMolfile
FormulaC29H46O12
Net Charge0
Average Mass586.675
Monoisotopic Mass586.29893
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@]2(O)CC[C@]1([H])C1COC(=O)C1
InChIInChI=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
InChIKeyZTFGOPUOTATSAL-CFVDWFIMSA-N
Roles Classification
Biological Role:
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).
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
dihydro-g-strophanthinChemIDplus
(1β,3β,5β,11α,20ξ)-3-[(6-deoxy-α-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxycardanolideChEBI
3β-[(6-deoxy-α-L-mannopyranosyl)oxy]-1β,5,11α,14,19-pentahydroxy-5β,20ξ-cardanolideChEBI
UniProt Name  Source
dihydroouabainUniProt
Manual XrefsDatabases
LSM-42697LINCS
HMDB0251322HMDB
Registry NumbersSources
Reaxys:71786Reaxys
CAS:1183-35-3ChemIDplus
Citations