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Substance Name: Azinomycin B
RN: 106486-76-4
UNII: 051R55X44C
InChIKey: QIKVYJOCQXXRSJ-PKDLRSQSSA-N

Note

  • Antitumor antibiotic produced by Streptomyces sahachiroi.

Classification Code

  • Drug / Therapeutic Agent

Molecular Formula

  • C31-H33-N3-O11

Molecular Weight

  • 623.6117
 
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Names and Synonyms

Name of Substance

  • Azinomycin B

Synonyms

  • Azinomycin B
  • BRN 5696947
  • Cardinophyllin
  • Carzinophilin A
  • Carzinophyllin
  • NSC 20088
  • UNII-051R55X44C

Systematic Names

  • 1-Naphthalenecarboxylic acid, 3-methoxy-5-methyl-, (1S)-2-(((1E)-1-((3R,4R,5S)-3-(acetyloxy)-4-hydroxy-1-azabicyclo(3.1.0)hex-2-ylidene)-2-(((1Z)-1-(hydroxymethylene)-2-oxopropyl)amino)-2-oxoethyl)amino)-1-((2S)-2-methyloxiranyl)-2-oxoethyl ester
  • 1-Naphthalenecarboxylic acid, 3-methoxy-5-methyl-, 2-((1-(3-(acetyloxy)-4-hydroxy-1-azabicyclo(3.1.0)hex-2-ylidene)-2-((1-(hydroxymethylene)-2-oxopropyl)amino)-2-oxoethyl)amino)-1-(2-methyloxiranyl)-2-oxoethyl ester

Registry Numbers

CAS Registry Number

  • 106486-76-4

FDA UNII

  • 051R55X44C

Other Registry Numbers

  • 1403-26-5
  • 1403-28-7
  • 1403-29-8
  • 81553-83-5

System Generated Number

  • 0106486764

Structure Descriptors

InChI

1S/C31H33N3O11/c1-14-7-6-8-18-19(14)9-17(42-5)10-20(18)30(41)45-27(31(4)13-43-31)29(40)33-23(28(39)32-21(12-35)15(2)36)24-26(44-16(3)37)25(38)22-11-34(22)24/h6-10,12,22,25-27,35,38H,11,13H2,1-5H3,(H,32,39)(H,33,40)/b21-12-,24-23+/t22-,25+,26+,27+,31-,34?/m0/s1

InChIKey

QIKVYJOCQXXRSJ-PKDLRSQSSA-N

Smiles

COc1cc(C(=O)O[C@H](C(=O)N\C(=C\2/[C@@H](OC(=O)C)[C@H](O)[C@@H]3CN23)\C(=O)N\C(=C/O)\C(=O)C)[C@]4(C)CO4)c5cccc(C)c5c1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 190ug/kg (0.19mg/kg)   Journal of Antibiotics. Vol. 40, Pg. 60, 1987.
mouse LD50 intraperitoneal 8000units/kg (8000units/kg)   Journal of Antibiotics, Series A. Vol. 13, Pg. 27, 1960.
mouse LD50 intravenous 15ug/kg (0.015mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1356, 1978.
mouse LD50 intravenous 500ug/kg (0.5mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 6, Pg. 300, 1981.
mouse LD50 subcutaneous 3mg/kg (3mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 6, Pg. 300, 1981.
mouse LD50 unreported 150ug/kg (0.15mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 199, 1967.