Structure Database (LMSD)

Common Name
digitoxin
Systematic 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
  • Crystodigin (TN)
  • Digitoxin
  • Digitoxoside
LM ID
LMST01120018
Formula
Exact Mass
Calculate m/z
764.434695
Status
Curated


Classification

Biological Context

Digitoxin is a cardiac glycoside that has been found in Digitalis and has diverse biological activities.1,2,3,4,5 It inhibits human recombinant α1β1, α2β2, and α3β1 subunit-containing Na+/K+-ATPases with Ki values of 250, 63, and 136 nM, respectively.1 Digitoxin inhibits the human-ether-a-go-go (hERG) potassium channel, also known as Kv11.1, in HEK293 cells expressing hERG (IC50 = 11.1 nM).2 It enhances developed tension and contractile force in electrically stimulated isolated guinea pig left atrial muscle when used at concentrations of 0.2 and 0.4 µM, respectively.3 Dietary administration of digitoxin (~1 mg/kg per day) attenuates congestive heart failure and reduces myocardial hypertrophy in a rat model of myocardial infarction induced by coronary artery ligation.4 Digitoxin is also cytotoxic to a panel of 10 human cancer cell lines, including myeloma, lymphoma, and leukemia cancer cells, with IC50 values ranging from 12 to 76 nM.5 Formulations containing digitoxin have previously been used in the treatment of congestive heart failure and cardiac arrhythmias.

This information has been provided by Cayman Chemical

References

1. Johansson, S., Lindholm, P., Gullbo, J., et al. Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs 12(5), 475-483 (2001).
3. Temma, K., Akera, T., and Brody, T.M. Inotropic effects of digitoxin in solated guines-pig heart under conditions which alter contraction. Eur. J. Pharm. 76(4), 361-370 (1981).
5. Katz, A., Lifshitz, Y., Bab-Dinitz, E., et al. Selectivity of digitalis glycosides for isoforms of human Na,K-ATPase. J. Biol. Chem. 285(25), 19582-19592 (2010).

String Representations

InChiKey (Click to copy)
WDJUZGPOPHTGOT-XUDUSOBPSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1[C@@]2(C)[C@]([H])(CC[C@]3([H])[C@]2([H])CC[C@@]2(C)[C@]3(O)CC[C@]2([H])C2=CC(=O)OC2)C[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@H](O)[C@H](O[C@@H]4O[C@H](C)[C@@H](O)[C@@H](O)C4)[C@@H](C)O3)[C@@H](O)C2)C1

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 54
Rings 8
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 727.97
Topological Polar Surface Area 191.11
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 13
logP 7.54
Molar Refractivity 198.88

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