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Substance Name: Antimycin A1
RN: 642-15-9
UNII: 8771CCP8LT
InChIKey: UIFFUZWRFRDZJC-UHFFFAOYSA-N

Note

  • An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed)

Molecular Formula

  • C28-H40-N2-O9

Molecular Weight

  • 548.629
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antifungal Agents
  • Drug / Therapeutic Agent
  • Natural Product
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Names and Synonyms

Name of Substance

  • Antimycin A
  • Antimycin A1

MeSH Heading

  • Antimycin A

Synonyms

  • Antimycin A1
  • EINECS 211-380-4
  • UNII-8771CCP8LT

Systematic Names

  • 3-(3-Formamidosalicylamido)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl isovalerate
  • Butanoic acid, 2(or 3)-methyl-, (2R,3S,6S,7R,8R)-3-((3-(formylamino)-2-hydroxybenzoyl)amino)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl ester
  • Butanoic acid, 2(or 3)-methyl-, 3-((3-(formylamino)-2-hydroxybenzoyl)amino)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl ester, (2R-(2R*,3S*,6S*,7R*,8R*))-
  • Isovaleric acid, 8-ester with 3-formamido-N-(7-hexyl-8-hydroxy-4,9-dimethyl-2,6-dioxo-1,5-dioxonan-3-yl)salicylamide

Registry Numbers

CAS Registry Number

  • 642-15-9

FDA UNII

  • 8771CCP8LT

Other Registry Numbers

  • 27220-56-0
  • 37341-24-5

System Generated Number

  • 0000642159

Structure Descriptors

InChI

1S/C28H40N2O9/c1-6-7-8-9-11-20-25(39-22(32)14-16(2)3)18(5)38-28(36)23(17(4)37-27(20)35)30-26(34)19-12-10-13-21(24(19)33)29-15-31/h10,12-13,15-18,20,23,25,33H,6-9,11,14H2,1-5H3,(H,29,31)(H,30,34)

InChIKey

UIFFUZWRFRDZJC-UHFFFAOYSA-N

Smiles

C1([C@@H]([C@@H]([C@@H](OC(=O)[C@@H]([C@@H](O1)C)NC(c1c(c(ccc1)NC=O)O)=O)C)OC(CC(C)C)=O)CCCCCC)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 1gm/kg (1000mg/kg)   Journal of Drug Research. Vol. 7(2), Pg. 1, 1975.
mouse LD50 intraperitoneal 7600ug/kg (7.6mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 144, 1967.
mouse LD50 intravenous 900ug/kg (0.9mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 144, 1967.
mouse LD50 subcutaneous 25mg/kg (25mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 144, 1967.
rat LD50 oral 1469mg/kg (1469mg/kg)   Journal of Drug Research. Vol. 7(2), Pg. 1, 1975.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 149.5 deg C   EXP
log P (octanol-water) 7.230 (none)   EST
Atmospheric OH Rate Constant 2.26E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.