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Substance Name: Tenuazonic acid
RN: 610-88-8
UNII: Y2J8Y1TO29
InChIKey: CEIZFXOZIQNICU-XNCJUZBTSA-N

Note

  • 3-Acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one. A metabolite found in a strain of the fungus Alternaria tenuis Auct. which functions as an antibiotic with antiviral and antineoplastic properties, and may also act as a mycotoxin.

Molecular Formula

  • C10-H15-N-O3

Molecular Weight

  • 197.2325
 

Classification Codes

  • Anti-Infective Agents
  • Antibiotics, Antineoplastic
  • Antineoplastic Agents
  • Antiviral Agents
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Names and Synonyms

Name of Substance

  • Tenuazonic acid

MeSH Heading

  • Tenuazonic acid

Synonyms

  • 3-Pyrrolin-2-one, 3-acetyl-5-sec-butyl-4-hydroxy-, L-
  • CCRIS 8400
  • L-Tenuazonic acid
  • Tenuazonic acid
  • UNII-Y2J8Y1TO29

Systematic Names

  • 2H-Pyrrol-2-one, 3-acetyl-1,5-dihydro-4-hydroxy-5-((1S)-1-methylpropyl)-, (5S)-
  • 2H-Pyrrol-2-one, 3-acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-, (S-(R*,R*))- (9CI)
  • 3-Pyrrolin-2-one, 3-acetyl-5-sec-butyl-4-hydroxy-, L-

Registry Numbers

CAS Registry Number

  • 610-88-8

FDA UNII

  • Y2J8Y1TO29

Other Registry Numbers

  • 128892-49-9
  • 16818-18-1

System Generated Number

  • 0000610888

Structure Descriptors

InChI

1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)/t5-,8-/m0/s1

InChIKey

CEIZFXOZIQNICU-XNCJUZBTSA-N

Smiles

CC[C@H](C)[C@@H]1NC(=O)C(=C1O)C(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 81mg/kg (81mg/kg)   EHP, Environmental Health Perspectives. Vol. 4, Pg. 87, 1973.
mouse LD50 intravenous 125mg/kg (125mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 65, 1981.
mouse LD50 oral 225mg/kg (225mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 65, 1981.
mouse LD50 subcutaneous 145mg/kg (145mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 65, 1981.