<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3804</id>
  <title>T3D3750</title>
  <common-name>Aurovertin B</common-name>
  <description>Aurovertin B is a mycotoxin and antibiotic produced by the fungus Calcarisporium arbuscula. It is known for its ability to inhibit oxidative phosphorylation. (A3002, A3032)</description>
  <cas>55350-03-3</cas>
  <pubchem-id>6441012</pubchem-id>
  <chemical-formula>C25H32O8</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>Aurovertins are a mixed, noncompetitive inhibitors of both ATP hydrolysis and synthesis. They do this by inhibiting the proton-pumping F1F0-ATP synthase by binding to beta-subunits in its F1 catalytic sector. F1F0-ATP synthase is responsible for the terminal step of oxidative phosphorylation. Each ATP synthase complex has three beta subunits, and aurovertins are believed to bind with varying affinity to two subunits on sites in a cleft between the nucleotide-binding and C-terminal domains, thus preventing closure of the catalytic interfaces necessary for the cyclic interconversion of catalytic sites.
(A3032, A3033, A3034)</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>Aurovertin B is a mycotoxin and antibiotic produced by the fungus Calcarisporium arbuscula. (A3002)</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2010-05-12T17:30:02Z</created-at>
  <updated-at type="dateTime">2026-04-05T13:12:47Z</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>DB07394</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(=C(/[H])\C(\[H])=C(/[H])C1=C(C)C(OC)=CC(=O)O1)/C(/[H])=C(\[H])C1OC2(C)C(CC)OC(C)(C2OC(C)=O)C1O</moldb-smiles>
  <moldb-formula>C25H32O8</moldb-formula>
  <moldb-inchi>InChI=1S/C25H32O8/c1-7-20-24(4)23(30-16(3)26)25(5,33-20)22(28)18(32-24)13-11-9-8-10-12-17-15(2)19(29-6)14-21(27)31-17/h8-14,18,20,22-23,28H,7H2,1-6H3/b9-8+,12-10+,13-11+</moldb-inchi>
  <moldb-inchikey>QXCOFYWOWZJFEA-YIDQAKLOSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">460.523</moldb-average-mass>
  <moldb-mono-mass type="decimal">460.20971799</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id nil="true"/>
  <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>CHEM002718</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00071822</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>100.52000000000002</moldb-polar-surface-area>
  <moldb-refractivity>125.50259999999999</moldb-refractivity>
  <moldb-polarizability>50.466648172042156</moldb-polarizability>
  <moldb-rotatable-bond-count>8</moldb-rotatable-bond-count>
  <moldb-acceptor-count>6</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic>12.9124340730191</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-3.7119013364614455</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>4.02</moldb-alogps-logp>
  <moldb-alogps-logs>-4.62</moldb-alogps-logs>
  <moldb-alogps-solubility>1.10e-02 g/l</moldb-alogps-solubility>
</compound>
