EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:4551 - digoxin

ChEBI IDCHEBI:4551
ChEBI Namedigoxin
Stars
DefinitionA cardenolide glycoside that is digitoxin β-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.
Secondary ChEBI IDsCHEBI:41856, CHEBI:569365, CHEBI:616935
Last Modified13 January 2020
DownloadsMolfile
FormulaC41H64O14
Net Charge0
Average Mass780.949
Monoisotopic Mass780.42961
SMILES[H][C@]12CC[C@]3([H])[C@]([H])(C[C@@H](O)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@@]43O)[C@@]1(C)CC[C@H](O[C@H]1C[C@H](O)[C@H](O[C@H]3C[C@H](O)[C@H](O[C@H]4C[C@H](O)[C@H](O)[C@@H](C)O4)[C@@H](C)O3)[C@@H](C)O1)C2
InChIInChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1
InChIKeyLTMHDMANZUZIPE-PUGKRICDSA-N
Wikipedia
Roles Classification
Biological Roles:
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).
epitope  The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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)
digoxin (CHEBI:4551) has role anti-arrhythmia drug (CHEBI:38070)
digoxin (CHEBI:4551) has role cardiotonic drug (CHEBI:38147)
digoxin (CHEBI:4551) has role EC 3.6.3.9 (Na+/K+-transporting ATPase) inhibitor (CHEBI:63510)
digoxin (CHEBI:4551) has role epitope (CHEBI:53000)
digoxin (CHEBI:4551) is a cardenolide glycoside (CHEBI:38092)
digoxin (CHEBI:4551) is a steroid saponin (CHEBI:61655)
digoxin (CHEBI:4551) is conjugate acid of digoxin(1−) (CHEBI:145795)
Incoming Relation(s)
12-O-acetyldigoxin (CHEBI:71006) has functional parent digoxin (CHEBI:4551)
20,22-dihydrodigoxin (CHEBI:71002) has functional parent digoxin (CHEBI:4551)
digoxin(1−) (CHEBI:145795) is conjugate base of digoxin (CHEBI:4551)
IUPAC Name 
(3β,5β,12β)-3-{[2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide
INN  Source
digoxinChemIDplus
Synonym  Source
12β-hydroxydigitoxinChemIDplus
Manual XrefsDatabases
C06956KEGG COMPOUND
DGXPDBeChem
D00298KEGG DRUG
DB00390DrugBank
1IGJPDB
DigoxinWikipedia
C00003618KNApSAcK
882DrugCentral
Registry NumbersSources
Reaxys:77011Reaxys
CAS:20830-75-5KEGG COMPOUND
CAS:20830-75-5ChemIDplus
Citations