CHEBI:28544 - digitoxin

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ChEBI Name digitoxin
ChEBI ID CHEBI:28544
Definition A cardenolide glycoside in which the 3β-hydroxy group of digitoxigenin carries a 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 trisaccharide chain.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:4549, CHEBI:23728
Supplier Information ChemicalBook:CB5194029, eMolecules:502080, eMolecules:713341, ZINC000095862733
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Formula C41H64O13
Net Charge 0
Average Mass 764.93910
Monoisotopic Mass 764.43469
InChI InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
InChIKey WDJUZGPOPHTGOT-XUDUSOBPSA-N
SMILES [H][C@]12CC[C@]3([H])[C@]([H])(CC[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): 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): 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 digitoxin (CHEBI:28544) has functional parent digitoxigenin (CHEBI:42219)
digitoxin (CHEBI:28544) has role EC 3.6.3.9 (Na+/K+-transporting ATPase) inhibitor (CHEBI:63510)
digitoxin (CHEBI:28544) is a cardenolide glycoside (CHEBI:38092)
digitoxin (CHEBI:28544) is conjugate acid of digitoxin(1−) (CHEBI:145796)
Incoming 3'''-O-acetyldigitoxin (CHEBI:53773) has functional parent digitoxin (CHEBI:28544)
digitoxin(1−) (CHEBI:145796) is conjugate base of digitoxin (CHEBI:28544)
IUPAC Name
3β-[2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyloxy]-14-hydroxy-5β-card-20(22)-enolide
Synonyms Sources
Crystodigin (TN) KEGG DRUG
Digitoxin KEGG COMPOUND
Digitoxoside ChemIDplus
Manual Xrefs Databases
881 DrugCentral
C00003617 KNApSAcK
C06955 KEGG COMPOUND
D00297 KEGG DRUG
DB01396 DrugBank
Digitoxin Wikipedia
View more database links
Registry Numbers Types Sources
71-63-6 CAS Registry Number KEGG COMPOUND
71-63-6 CAS Registry Number ChemIDplus
76678 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10438974 PubMed citation Europe PMC
10687899 PubMed citation Europe PMC
26573786 PubMed citation Europe PMC
Last Modified
13 January 2020