<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4072</id>
  <title>T3D4018</title>
  <common-name>Ouabain</common-name>
  <description>Ouabain is only found in individuals that have used or taken this drug. It is a cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like digitalis. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-exchanging ATPase. 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.</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>
</compound>
