Structure via PubChem · Public domain (PubChem)
sterigmatocystin
Sign in to saveSterigmatocystin is a polyketide mycotoxin produced by certain species of Aspergillus. The toxin is naturally found in some cheeses.
Chemical data
- Formula
- C18H12O6
- Molecular weight
- 324.3 g/mol
- IUPAC name
- (3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one
- SMILES
- COC1=C2C(=C3[C@@H]4C=CO[C@@H]4OC3=C1)OC5=CC=CC(=C5C2=O)O
- InChIKey
- UTSVPXMQSFGQTM-DCXZOGHSSA-N
- XLogP
- 3.4
- Polar surface area
- 74.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 324.063388104
Show 5 more facts
- chemical formula
- C₁₈H₁₂O₆
- found in taxon
- Aspergillus versicolor
- isomeric SMILES
- COC1=C2C(=C3[C@@H]4C=CO[C@@H]4OC3=C1)OC5=C(C2=O)C(=CC=C5)O
- canonical SMILES
- O=C1C=2C(O)=CC=CC2OC=3C1=C(OC)C=C4OC5OC=CC5C43
- subject has role
- carcinogen
via Wikidata · CC0
~7 min read
Encyclopedic overview
9 sectionsContents
- Chemical and physical properties
- Toxicity and importance
- Natural occurrence
- Sampling and analysis
- Stability and Persistence
- Legislation and control
- See also
- References
- External links
Sterigmatocystin is a polyketide mycotoxin produced by certain species of Aspergillus. The toxin is naturally found in some cheeses.
Sterigmatocystin is a toxic metabolite structurally closely related to the aflatoxins as it is the penultimate precursor of aflatoxins B1 and G1. It contains a xanthone nucleus attached to a bifuran structure. Sterigmatocystin is mainly produced by the fungi Aspergillus nidulans and A. versicolor.
Excerpted from Wikipedia’s “sterigmatocystin” article, available under the CC BY-SA 4.0 licence.