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Substance Name: Echinomycin
RN: 512-64-1
UNII: TG824J6RQT
InChIKey: AUJXLBOHYWTPFV-VITLIGDRSA-N

Note

  • A cytotoxic polypeptide quinoxaline antibiotic isolated from Streptomyces echinatus that binds to DNA and inhibits RNA synthesis.

Molecular Formula

  • C51-H64-N12-O12-S2

Molecular Weight

  • 1101.2706
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibiotics, Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Nucleic Acid Synthesis Inhibitors
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Names and Synonyms

Name of Substance

  • Echinomycin

MeSH Heading

  • Echinomycin

Synonyms

  • 4-27-00-09726 (Beilstein Handbook Reference)
  • BRN 0078671
  • Echinomycin
  • NSC 526417
  • NSC-526417
  • NSC526417
  • Quinomycin A
  • S-426-S (Lepetit)
  • SK 302B
  • Stereoisomer of N,N'-(2,4,12,15,17,25-hexamethyl-11,24-bis(1-methylethyl)-27-(methylthio)-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28-thia-2,5,12,15,18,25-hexaazabicyclo(12.12.3)nonacosane-7,20-diyl)bis(2-quinoxalinecarboxamide)
  • UNII-TG824J6RQT

Systematic Names

  • Echinomycin
  • Quinomycin A

Registry Numbers

CAS Registry Number

  • 512-64-1

FDA UNII

  • TG824J6RQT

Other Registry Number

  • 11016-61-8

System Generated Number

  • 0000512641

Structure Descriptors

InChI

InChI=1S/C51H64N12O12S2/c1-25(2)38-49(72)74-22-36(59-42(65)34-21-53-30-17-13-15-19-32(30)57-34)44(67)55-28(6)46(69)63(10)40-48(71)62(9)39(26(3)4)50(73)75-23-35(58-41(64)33-20-52-29-16-12-14-18-31(29)56-33)43(66)54-27(5)45(68)60(7)37(47(70)61(38)8)24-77-51(40)76-11/h12-21,25-28,35-40,51H,22-24H2,1-11H3,(H,54,66)(H,55,67)(H,58,64)(H,59,65)/t27-,28-,35+,36+,37-,38-,39-,40+,51?/m0/s1

InChIKey

AUJXLBOHYWTPFV-VITLIGDRSA-N

Smiles

CSC1SC[C@@H]2N(C)C(=O)[C@H](C)NC(=O)[C@@H](COC(=O)[C@H](C(C)C)N(C)C(=O)[C@H]1N(C)C(=O)[C@H](C)NC(=O)[C@@H](COC(=O)[C@H](C(C)C)N(C)C2=O)NC(=O)c3cnc4ccccc4n3)NC(=O)c5cnc6ccccc6n5

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 89ug/kg (0.089mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING
National Technical Information Service. Vol. PB83-114298,
mouse LD50 intraperitoneal 280ug/kg (0.28mg/kg)   Journal of Antibiotics. Vol. 21, Pg. 465, 1968.
mouse LD50 intravenous 629ug/kg (0.629mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. PB83-114298,
mouse LD50 subcutaneous 3800ug/kg (3.8mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 311, 1978.