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Substance Name: Tunicamycin
RN: 11089-65-9
UNII: 55W4525Q2E
InChIKey: ZHSGGJXRNHWHRS-VIDYELAYSA-N

Note

  • An N-acetylglycosamine containing antiviral antibiotic obtained from Streptomyces lysosuperificus. It is also active against some bacteria and fungi, because it inhibits the glucosylation of proteins. Tunicamycin is used as tool in the study of microbial biosynthetic mechanisms.

Molecular Formula

  • Unspecified

Molecular Weight

  • 718.7054
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antiviral Agents
  • Mutation Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Tunicamycin

MeSH Heading

  • Tunicamycin

Synonyms

  • NSC 177382
  • Tunicamycin
  • UNII-55W4525Q2E

Systematic Name

  • Tunicamycin

Registry Numbers

CAS Registry Number

  • 11089-65-9

FDA UNII

  • 55W4525Q2E

Other Registry Number

  • 11118-26-6

System Generated Number

  • 0011089659

Structure Descriptors

InChI

1S/C30H46N4O16/c1-11(2)5-4-6-16(38)32-19-23(43)20(40)14(47-29(19)50-28-18(31-12(3)36)22(42)21(41)15(10-35)48-28)9-13(37)26-24(44)25(45)27(49-26)34-8-7-17(39)33-30(34)46/h4,6-8,11,13-15,18-29,35,37,40-45H,5,9-10H2,1-3H3,(H,31,36)(H,32,38)(H,33,39,46)/b6-4+/t13?,14-,15-,18-,19-,20+,21-,22-,23-,24+,25-,26-,27-,28-,29+/m1/s1

InChIKey

ZHSGGJXRNHWHRS-VIDYELAYSA-N

Smiles

O([C@H]1[C@@H]([C@H]([C@@H](O)[C@H](O1)C[C@@H]([C@H]1O[C@@H](n2c([nH]c(=O)cc2)=O)[C@@H]([C@@H]1O)O)O)O)NC(\C=C\CC(C)C)=O)[C@@H]1[C@@H]([C@H]([C@H](O)[C@H](O1)CO)O)NC(C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
domestic animals - goat/sheep LDLo subcutaneous 20ug/kg (0.02mg/kg) LIVER: OTHER CHANGES

BEHAVIORAL: ATAXIA
Australian Veterinary Journal. Vol. 76, Pg. 287, 1998.
guinea pig LD subcutaneous > 400ug/kg (0.4mg/kg)   Pathology. Vol. 21, Pg. 194, 1989.
guinea pig LD subcutaneous > 400ug/kg (0.4mg/kg) BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"

LIVER: OTHER CHANGES
Pathology. Vol. 21, Pg. 194, 1989.
rat LD subcutaneous > 200ug/kg (0.2mg/kg)   Australian Veterinary Journal. Vol. 76, Pg. 287, 1998.
rat LD subcutaneous > 200ug/kg (0.2mg/kg) LIVER: OTHER CHANGES Australian Veterinary Journal. Vol. 76, Pg. 287, 1998.