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<compound>
  <id type="integer">3785</id>
  <title>T3D3731</title>
  <common-name>Rubratoxin A</common-name>
  <description>Rubratoxin A is an exogenous compound that exists as a solid at room temperature. It has the chemical formula C26H32O11. Rubratoxin A belongs to the tetracarboxylic acids and derivatives, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 520.53 g/mol, Rubratoxin A is a heavy molecule.

The compound acts as a potent inhibitor of protein phosphatase 2A, specifically targeting the serine/threonine-protein phosphatase 2A catalytic subunit alpha isoform (PPP2CA), the serine/threonine-protein phosphatase 2A catalytic subunit beta isoform (PPP2CB), and the serine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoform (PPP2R1A). This inhibition exerts antitumor and antimetastatic effects. These antimetastatic effects may be attributed to the phosphorylation of CREB and subsequent activation of natural killer cells via the stimulation of interleukin-2 release from T cells, as well as the phosphorylation of focal adhesion kinase and paxillin, which interferes with cell adhesion. Additionally, Rubratoxin A inhibits Na+/K+-transporting ATPases in the brain. The recorded protein targets for this action include the sodium/potassium-transporting ATPase subunit gamma (FXYD2), sodium/potassium-transporting ATPase subunit alpha-1 (ATP1A1), sodium/potassium-transporting ATPase subunit alpha-2 (ATP1A2), sodium/potassium-transporting ATPase subunit alpha-3 (ATP1A3), and four other proteins.</description>
  <cas>22467-31-8</cas>
  <pubchem-id>31181</pubchem-id>
  <chemical-formula>C26H32O11</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point nil="true"/>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility nil="true"/>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Rubratoxin A is a potent inhibitor of protein phosphatase 2A, exerting antitumor and antimetastatic effects. Inhibition may cause the phosphorylation of CREB and subsequent activation of natural killer cells via the stimulation of interleukin-2 release from T cells, contributing to antimetastatic effects. Focal adhesion kinase phosphorylation and paxillin phosphorylation that interfere with cell adhesion could be another antimetastatic effect. Rubratoxin A has also been shown to inhibit Na+/K+-transporting ATPases. (A2987, A2988)</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>Rubratoxin A is a mycotoxin produced by fungi such as Penicillum rubrum and Penicillum purpurogenum, which are common soil fungi that sometimes contaminate animal feeds. (A2985, A2988)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Rubratoxins are hepatotoxic, nephrotoxic, and splenotoxic, causing congestive, hemorrhagic and degenerative lesions. (A2985, A2986)</health-effects>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2010-05-05T14:57:46Z</created-at>
  <updated-at type="dateTime">2026-04-06T13:51:16Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id nil="true"/>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <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>CCCCCCC(O)C1C(O)C2=C(CC(CC3=C1C(=O)OC3O)C(O)C1CC=CC(=O)O1)C(=O)OC2=O</moldb-smiles>
  <moldb-formula>C26H32O11</moldb-formula>
  <moldb-inchi>InChI=1S/C26H32O11/c1-2-3-4-5-7-15(27)20-18-13(23(31)36-25(18)33)10-12(21(29)16-8-6-9-17(28)35-16)11-14-19(22(20)30)26(34)37-24(14)32/h6,9,12,15-16,20-23,27,29-31H,2-5,7-8,10-11H2,1H3</moldb-inchi>
  <moldb-inchikey>XOEFANNJIKAWGX-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">520.5257</moldb-average-mass>
  <moldb-mono-mass type="decimal">520.194461866</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>28923</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>CHEM002700</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00126675</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>176.89</moldb-polar-surface-area>
  <moldb-refractivity>126.96669999999995</moldb-refractivity>
  <moldb-polarizability>52.800797820607855</moldb-polarizability>
  <moldb-rotatable-bond-count>8</moldb-rotatable-bond-count>
  <moldb-acceptor-count>8</moldb-acceptor-count>
  <moldb-donor-count>4</moldb-donor-count>
  <moldb-pka-strongest-acidic>5.818870700637414</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-2.8988760446550055</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>4</moldb-number-of-rings>
  <moldb-alogps-logp>1.03</moldb-alogps-logp>
  <moldb-alogps-logs>-3.01</moldb-alogps-logs>
  <moldb-alogps-solubility>5.10e-01 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organic acids and derivatives</superklass>
  <klass>Carboxylic acids and derivatives</klass>
  <subklass>Tetracarboxylic acids and derivatives</subklass>
  <paper-count type="integer">198</paper-count>
  <sync-id>CED0015327</sync-id>
  <structure-inchikey>XOEFANNJIKAWGX-UHFFFAOYSA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:53Z</structure-indexed-at>
</compound>
