Structure Database (LMSD)

Common Name
Sterigmatocystin
Systematic Name
(3aR,12cS)-8-Hydroxy-6-methoxy-3a,12c-dihydro-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one
Synonyms
LM ID
LMPK10000001
Formula
C18H12O6
Exact Mass
Calculate m/z
324.06339
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Aflatoxins and related substances [PK10]

Biological Context

Sterigmatocystin is a mycotoxin that has been found in Aspergillus.1,2 It is lethal to rats (LD50 = 60 mg/kg) and chick embryos (LD50s = 5-7 µg/embryo).2 Sterigmatocystin (100 and 1,000 ppb in drinking water) induces gastritis, as well as intestinal polyp formation and metaplasia in aged Mongolian gerbils.1 It induces formation of lung and liver adenomas and malignant lymphomas in newborn mice.3

This information has been provided by Cayman Chemical

References

1. Kusunoki, M., Misumi, J., Shimada, T., et al. Long-term administration of the fungus toxin, sterigmatocystin, induces intestinal metaplasia and increases the proliferative activity of PCNA, p53, and MDM2 in the gastric mucosa of aged Mongolian gerbils. Environ. Health Prev. Med. 16(4), 224-231 (2011).
2. Schroeder, H.W., and Kelton, W.H. Production of sterigmatocystin by some species of the genus Aspergillus and its toxicity to chicken embryos. Appl. Microbiol. 30(4), 589-591 (1975).
3. Fujii, K., Kurata, H., Odashima, S., et al. Tumor induction by a single subcutaneous injection of sterigmatocystin in newborn mice. Cancer Res. 36(5), 1615-1618 (1976).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Aspergillus versicolor (#46472)
Eurotiomycetes (#147545)
Studies in mycological chemistry. Part XI. The structure of isosterigmatocystin and an amended structure for sterigmatocystin,
J Chem Soc, 1962

String Representations

InChiKey (Click to copy)
UTSVPXMQSFGQTM-DCXZOGHSSA-N
InChi (Click to copy)
InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
SMILES (Click to copy)
C12OC3=C(C(O)=CC=C3)C(=O)C=1C(=CC1O[C@@]3([H])OC=C[C@@]3([H])C2=1)OC

Other Databases

Wikipedia
Sterigmatocystin
KEGG ID
C00961
CHEBI ID
18227
PubChem CID
5280389
Cayman ID
11441

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 5
Aromatic Rings 3
Rotatable Bonds 1
Van der Waals Molecular Volume 257.08
Topological Polar Surface Area 82.27
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 6
logP 4.19
Molar Refractivity 86.21

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Created at
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Updated at
21st Feb 2025