Chemicals and Drugs

Digitonin

A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.

Chemical Identity

Chemical Information

Molecular Formula
C56H92O29
Molecular Weight
1229.3 g/mol
CAS Registry No.
11024-24-1
IUPAC Name
(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-6-[(1R,2S,3S,4R,5'R,6R,7S,8R,9S,12S,13S,15R,16R,18S)-3,15-dihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
InChIKey
UVYVLBIGDKGWPX-KUAJCENISA-N
SMILES
C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)[C@H]([C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(C[C@H]([C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O)O)C)C)O)C)OC1
MeSH Unique ID
D004072
Source
PubChem CID 6474107

MeSH Record

Classification

Broader headings

Related Concepts

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

1 entry terms
  • Digitin

MeSH Record

Aspects Covered

27 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

79(73); was see under DIGITALIS GLYCOSIDES 1975-78

MeSH Record

Previous Indexing

  • Digitalis Glycosides (1966-1972)
  • Indicators and Reagents (1966-1972)

MeSH Hierarchy

Tree Numbers

  1. D04w.210.500w.155.580w.130.500.236w
  2. D09w.408w.180w.261.236w

AMA Style

References

  1. National Library of Medicine. Digitonin. Medical Subject Headings (MeSH). 2026. Unique ID D004072. http://id.nlm.nih.gov/mesh/2026/D004072
  2. Digitonin. In: Wikipedia. https://en.wikipedia.org/wiki/Digitonin
  3. Digitonin. In: Wikidata. https://www.wikidata.org/wiki/Q410968
  4. Digitonin. In: PubChem Compound. CID 6474107. https://pubchem.ncbi.nlm.nih.gov/compound/6474107