<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4072</id>
  <title>T3D4018</title>
  <common-name>Ouabain</common-name>
  <description>Ouabain is an exogenous solid with the chemical formula C29H44O12. Ouabain belongs to the steroid lactones, a subclass of steroids and steroid derivatives within the organic compounds. With an average molecular weight of 584.65 g/mol, Ouabain is a heavy molecule. This plant metabolite is used as a cardiotonic drug and an anti-arrhythmia drug.

In biological and chemical contexts, ouabain functions as an ion transport inhibitor. It acts as an inhibitor for the Na(+)/K(+)-transporting ATPase (EC 3.6.3.9), the H(+)/K(+)-exchanging ATPase (EC 3.6.3.10), citrate (Si)-synthase (EC 2.3.3.1), and 4-nitrophenylphosphatase (EC 3.1.3.41). Its recorded protein targets include the alpha-1, alpha-2, and alpha-3 subunits of the sodium/potassium-transporting ATPase (ATP1A1, ATP1A2, and ATP1A3). Ouabain is found in three recorded sources: television systems within electrical and electronic equipment, and the preparation of vinegar, wine, or sparkling wine within food, food processing, and cookware.</description>
  <cas>630-60-4</cas>
  <pubchem-id>439501</pubchem-id>
  <chemical-formula>C29H44O12</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>200°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>1.03E+004 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>Ouabain 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). Ouabain 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 nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of atrial fibrillation and flutter and heart failure</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T04:49:16Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:57:45Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Ouabain</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C01443</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>472805</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB01092</drugbank-id>
  <pdb-id>OBN</pdb-id>
  <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(O)C[C@H](C[C@@H](O)[C@]3(CO)[C@@]1([H])[C@H](O)C[C@]1(C)[C@H](CC[C@]21O)C1=CC(=O)OC1)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O</moldb-smiles>
  <moldb-formula>C29H44O12</moldb-formula>
  <moldb-inchi>InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1</moldb-inchi>
  <moldb-inchikey>LPMXVESGRSUGHW-HBYQJFLCSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">584.6525</moldb-average-mass>
  <moldb-mono-mass type="decimal">584.283276872</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-2</logp>
  <hmdb-id>HMDB15224</hmdb-id>
  <chembl-id>CHEMBL222863</chembl-id>
  <chemspider-id>388599</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>CHEM002978</chemdb-id>
  <dsstox-id>DTXSID0043765</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00003260</susdat-id>
  <iupac>4-[(1R,3aS,3bR,5aS,7S,9R,9aR,9bS,10R,11aR)-3a,5a,9,10-tetrahydroxy-9a-(hydroxymethyl)-11a-methyl-7-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2,5-dihydrofuran-2-one</iupac>
  <moldb-polar-surface-area>206.59999999999997</moldb-polar-surface-area>
  <moldb-refractivity>140.83379999999994</moldb-refractivity>
  <moldb-polarizability>59.92556829434825</moldb-polarizability>
  <moldb-rotatable-bond-count>4</moldb-rotatable-bond-count>
  <moldb-acceptor-count>11</moldb-acceptor-count>
  <moldb-donor-count>8</moldb-donor-count>
  <moldb-pka-strongest-acidic>7.181446894362235</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-2.8503841755458543</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>6</moldb-number-of-rings>
  <moldb-alogps-logp>-1.03</moldb-alogps-logp>
  <moldb-alogps-logs>-2.10</moldb-alogps-logs>
  <moldb-alogps-solubility>4.61e+00 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Lipids and lipid-like molecules</superklass>
  <klass>Steroids and steroid derivatives</klass>
  <subklass>Steroid lactones</subklass>
  <paper-count type="integer">19311</paper-count>
  <sync-id>CED0002282</sync-id>
  <structure-inchikey>LPMXVESGRSUGHW-HBYQJFLCSA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:01:03Z</structure-indexed-at>
</compound>
