<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3791</id>
  <title>T3D3737</title>
  <common-name>Citreoviridin A</common-name>
  <description>Citreoviridin A is a metabolite of Penicillium citreo-viride, Penicillium toxicarium, Penicillium ochrosalmoneum and Aspergillus terreus. It is isolated from mouldy rice. Toxin formerly responsible for epidemic-like occurrences of cardiac beriberi in East AsiaCitreoviridin A belongs to the family of Pyranones and Derivatives. These are compounds containing a pyran ring which bears a ketone.</description>
  <cas>25425-12-1</cas>
  <pubchem-id>6436023</pubchem-id>
  <chemical-formula>C23H30O6</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>107 - 111°C</melting-point>
  <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>Citreoviridin inhibits both membrane-bound and soluble mitochondrial ATPases. In particular, it inhibits synaptosomal Na+/K+-ATPase, altering synaptic transmission, and binds to the beta subunit of F1-ATPAse. As a result it has been shown to inhibit mitochondrial energy-linked reactions such as ADP-stimulated respiration, ATP-driven reduction of NAD + by succinate, and ATP-driven NAD transhydrogenase. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interfering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (A3002, A3003, A3005, A3006, A3014)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity>LD50: 3.6 mg/kg (Subcutaneous, rat) (A3002)
LD50: 7.5 mg/kg (Intraperitoneal, Mouse) (A3002)
LD50: 29 mg/kg (Oral, Mouse) (A3002)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Citreoviridin is a mycotoxin that has been isolated in Peniciilium citreo-viride, P. ochrosalmoneum, and P. pulvullorum. It can be found in contaminated rice grains, as well as corn infested by Eupenicillium
ochrosalmoneurn. (A3002)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Citreoviridin selectively inhibits motor nerve cells in the medulla oblongata and accumulates in
the grey matter and brain stem. This can cause central nervous system depression leading to respiratory and cardiovascular failures and death. (A3002, A3004, A3005)</health-effects>
  <symptoms>Symptoms of citreoviridin exposure include progressive paralysis, vomiting, convulsions, and gradual
respiratory disorder. (A3002)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2010-05-06T14:52:05Z</created-at>
  <updated-at type="dateTime">2026-04-03T05:06:40Z</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>[H]/C(=C(/[H])\C(\[H])=C(/[H])C1=C(C)C(OC)=CC(=O)O1)/C(/[H])=C(\[H])/C(/C)=C(\[H])C1(C)OC(C)C(C)(O)C1O</moldb-smiles>
  <moldb-formula>C23H30O6</moldb-formula>
  <moldb-inchi>InChI=1S/C23H30O6/c1-15(14-22(4)21(25)23(5,26)17(3)29-22)11-9-7-8-10-12-18-16(2)19(27-6)13-20(24)28-18/h7-14,17,21,25-26H,1-6H3/b8-7+,11-9+,12-10+,15-14+</moldb-inchi>
  <moldb-inchikey>JLSVDPQAIKFBTO-USJRQALFSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">402.4807</moldb-average-mass>
  <moldb-mono-mass type="decimal">402.204238692</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB30868</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>4525192</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 nil="true"/>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002706</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00018334</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>85.22000000000001</moldb-polar-surface-area>
  <moldb-refractivity>118.01279999999998</moldb-refractivity>
  <moldb-polarizability>45.46314193988334</moldb-polarizability>
  <moldb-rotatable-bond-count>6</moldb-rotatable-bond-count>
  <moldb-acceptor-count>5</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>12.600983692839542</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-3.662280515270547</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>3.89</moldb-alogps-logp>
  <moldb-alogps-logs>-4.63</moldb-alogps-logs>
  <moldb-alogps-solubility>9.36e-03 g/l</moldb-alogps-solubility>
</compound>
