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Substance Name: Sterigmatocystin
RN: 10048-13-2
UNII: 5F95211S5Z
InChIKey: UTSVPXMQSFGQTM-DCXZOGHSSA-N

Note

  • A carcinogenic mycotoxin produced in high yields by strains of the common molds, Aspergillus versicolor, A. nidulans, and an unidentified species of Bipolaris. It causes necrosis of the liver and kidney and has an inhibitory effect on orotic acid incorporation into nuclear RNA.

Molecular Formula

  • C18-H12-O6

Molecular Weight

  • 324.2868
 

Classification Codes

Classification Codes

  • Mutation Data
  • Natural Product
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 2B
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Names and Synonyms

Name of Substance

  • Sterigmatocystin

MeSH Heading

  • Sterigmatocystin

Synonyms

  • 3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo(3',2':4,5)furo(2,3-c)xanthen-7-one
  • 7H-Furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-, (3aR-cis)-
  • CCRIS 561
  • EINECS 233-158-6
  • HSDB 3540
  • NSC 201423
  • NSC 204985
  • Sterigmatocystin
  • Sterigmatocystine
  • UNII-5F95211S5Z

Systematic Names

  • (3AR-cis)3a,12c-dihydro-8-hydroxy-6-methoxy-7H-furo(3',2':4,5)furo(2,3-c)xanthen-7-one
  • 7H-Furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-
  • 7H-Furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-, (3aR,12cS)-
  • Sterigmatocystin

Superlist Names

  • 7H-Furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-, (3aR-cis)-
  • Sterigmatocystin

Registry Numbers

CAS Registry Number

  • 10048-13-2

FDA UNII

  • 5F95211S5Z

Other Registry Number

  • 105521-97-9

System Generated Number

  • 0010048132

Structure Descriptors

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

InChIKey

UTSVPXMQSFGQTM-DCXZOGHSSA-N

Smiles

COc1cc2c(c3c1c(=O)c4c(cccc4o3)O)[C@@H]5C=CO[C@@H]5O2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 intraperitoneal 10mg/kg (10mg/kg) SKIN AND APPENDAGES (SKIN): OTHER GLANDS: OTHER Mycopathologia. Vol. 97, Pg. 51, 1987.
chicken LD50 oral 41mg/kg (41mg/kg)   Journal of the American College of Toxicology. Vol. 5(4), Pg. 275, 1986.
monkey LD50 intraperitoneal 32mg/kg (32mg/kg) LIVER: OTHER CHANGES British Journal of Experimental Pathology. Vol. 51, Pg. 183, 1970.
mouse LD50 oral > 800mg/kg (800mg/kg)   Mycopathologia et Mycologia Applicata. Vol. 35, Pg. 373, 1968.
rat LD50 intraperitoneal 60mg/kg (60mg/kg) KIDNEY, URETER, AND BLADDER: CHANGES PRIMARILY IN GLOMERULI

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: FATTY LIVER DEGERATION
Food and Cosmetics Toxicology. Vol. 7, Pg. 135, 1969.
rat LD50 oral 120mg/kg (120mg/kg) LIVER: FATTY LIVER DEGERATION

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

KIDNEY, URETER, AND BLADDER: CHANGES PRIMARILY IN GLOMERULI
Food and Cosmetics Toxicology. Vol. 7, Pg. 135, 1969.