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CHEBI:4551 - digoxin

Default Structure
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:
antiviral agent  A substance that destroys or inhibits replication of viruses.
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.
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
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).
anti-HBV agent  An antiviral agent that destroys or inhibits the replication of the hepatitis B virus.
anti-obesity agent  Any substance which is used to reduce or control weight.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
antiemetic  A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
hypoglycemic agent  A drug which lowers the blood glucose level.
antirheumatic drug  A drug used to treat rheumatoid arthritis.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
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.
anticonvulsant  A drug used to prevent seizures or reduce their severity.
cardioprotective agent  Any protective agent that is able to prevent damage to the heart.
ChEBI Ontology
Outgoing Relation(s)
digoxin (CHEBI:4551) has role analgesic (CHEBI:35480)
digoxin (CHEBI:4551) has role anti-arrhythmia drug (CHEBI:38070)
digoxin (CHEBI:4551) has role anti-HBV agent (CHEBI:64951)
digoxin (CHEBI:4551) has role anti-HIV agent (CHEBI:64946)
digoxin (CHEBI:4551) has role anti-inflammatory agent (CHEBI:67079)
digoxin (CHEBI:4551) has role anti-obesity agent (CHEBI:74518)
digoxin (CHEBI:4551) has role anticonvulsant (CHEBI:35623)
digoxin (CHEBI:4551) has role antidepressant (CHEBI:35469)
digoxin (CHEBI:4551) has role antiemetic (CHEBI:50919)
digoxin (CHEBI:4551) has role antihypertensive agent (CHEBI:35674)
digoxin (CHEBI:4551) has role antiinfective agent (CHEBI:35441)
digoxin (CHEBI:4551) has role antineoplastic agent (CHEBI:35610)
digoxin (CHEBI:4551) has role antirheumatic drug (CHEBI:35842)
digoxin (CHEBI:4551) has role antiviral agent (CHEBI:22587)
digoxin (CHEBI:4551) has role cardiotonic drug (CHEBI:38147)
digoxin (CHEBI:4551) has role cardiovascular drug (CHEBI:35554)
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) has role hypoglycemic agent (CHEBI:35526)
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
INNs  Source
digoxinChemIDplus
digoxinaWHO MedNet
Synonyms  Source
12β-hydroxydigitoxinChemIDplus
DigoxinumChEMBL
FargoxinChEMBL
LanocardinChEMBL
MapluxinChEMBL
NatigoxinChEMBL
Brand Names  Source
DigamexChEMBL
Lanoxin-125ChEMBL
Lanoxin pediatricChEMBL
Lanoxin-pgChEMBL
Manual XrefsDatabases
1IGJPDB
882DrugCentral
C00003618KNApSAcK
C06956KEGG COMPOUND
D00298KEGG DRUG
DB00390DrugBank
DGXPDBeChem
DigoxinWikipedia
Registry NumbersSources
Reaxys:77011Reaxys
CAS:20830-75-5KEGG COMPOUND
CAS:20830-75-5ChemIDplus
Citations