CHEBI:4551 - digoxin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name digoxin
ChEBI ID CHEBI:4551
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41856, CHEBI:569365, CHEBI:616935
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Formula C41H64O14
Net Charge 0
Average Mass 780.93850
Monoisotopic Mass 780.430
InChI InChI=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
InChIKey LTMHDMANZUZIPE-PUGKRICDSA-N
SMILES [H][C@]12CC[C@]3([H])[C@]([H])(C[C@@H](O)[C@]4(C)[C@H](CC[C@]34O)C3=CC(=O)OC3)[C@@]1(C)CC[C@@H](C2)O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@H]3C[C@H](O)[C@H](O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1
Roles Classification
Biological Role(s): 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.
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).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
Application(s): 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.
cardiotonic drug
A drug that has a strengthening effect on the heart or that can increase cardiac output.
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 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)
Incoming 12-O-acetyldigoxin (CHEBI:71006) has functional parent digoxin (CHEBI:4551)
20,22-dihydrodigoxin (CHEBI:71002) has functional parent 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
digoxin ChemIDplus
Synonym Source
12β-hydroxydigitoxin ChemIDplus
Database Links Databases
1IGJ PDB
882 DrugCentral
C00003618 KNApSAcK
C06956 KEGG COMPOUND
D00298 KEGG DRUG
DB00390 DrugBank
DGX PDBeChem
Digoxin Wikipedia
View more database links
Registry Numbers Types Sources
20830-75-5 CAS Registry Number KEGG COMPOUND
20830-75-5 CAS Registry Number ChemIDplus
77011 Beilstein Registry Number Beilstein
77011 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10438974 PubMed citation Europe PMC
16970134 PubMed citation Europe PMC
7739045 PubMed citation Europe PMC
8234291 PubMed citation Europe PMC
Last Modified
22 February 2017