<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4075</id>
  <title>T3D4021</title>
  <common-name>Digitoxin</common-name>
  <description>Digitoxin is only found in individuals that have used or taken this drug. It is a cardiac glycoside sometimes used in place of digoxin. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665)Digitoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digitoxin also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.</description>
  <cas>71-63-6</cas>
  <pubchem-id>441207</pubchem-id>
  <chemical-formula>C41H64O13</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>255.5°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>3.9 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>Digitoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digitoxin also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.</mechanism-of-toxicity>
  <metabolism>Hepatic.</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T04:49:19Z</created-at>
  <updated-at type="dateTime">2026-05-14T17:00:05Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Digitoxin</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C06955</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>28544</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB01396</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-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</moldb-smiles>
  <moldb-formula>C41H64O13</moldb-formula>
  <moldb-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</moldb-inchi>
  <moldb-inchikey>WDJUZGPOPHTGOT-XUDUSOBPSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">764.9391</moldb-average-mass>
  <moldb-mono-mass type="decimal">764.434692134</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.85</logp>
  <hmdb-id>HMDB15468</hmdb-id>
  <chembl-id>CHEMBL254219</chembl-id>
  <chemspider-id>389987</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002981</chemdb-id>
  <dsstox-id>DTXSID0022933</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00010457</susdat-id>
  <iupac>4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-7-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2,5-dihydrofuran-2-one</iupac>
  <moldb-polar-surface-area>182.82999999999998</moldb-polar-surface-area>
  <moldb-refractivity>191.71729999999994</moldb-refractivity>
  <moldb-polarizability>83.53719678485017</moldb-polarizability>
  <moldb-rotatable-bond-count>7</moldb-rotatable-bond-count>
  <moldb-acceptor-count>12</moldb-acceptor-count>
  <moldb-donor-count>5</moldb-donor-count>
  <moldb-pka-strongest-acidic>7.1826356067617585</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>0.2422182727916835</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>8</moldb-number-of-rings>
  <moldb-alogps-logp>2.33</moldb-alogps-logp>
  <moldb-alogps-logs>-4.42</moldb-alogps-logs>
  <moldb-alogps-solubility>2.89e-02 g/l</moldb-alogps-solubility>
</compound>
