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Substance Name: Coumermycin [USAN]
RN: 4434-05-3
UNII: PCH9QZ1IIH
InChIKey: WTIJXIZOODAMJT-DHFGXMAYSA-N

Classification Codes

  • Antibacterial
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Topoisomerase II Inhibitors

Molecular Formula

  • C55-H59-N5-O20

Molecular Weight

  • 1110.0861
 
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Names and Synonyms

Name of Substance

  • Coumamycin [INN]
  • Coumermycin
  • Coumermycin [USAN]

Synonyms

  • 5-Methylpyrrole-2-carboxylic acid, diester with 3,3'-((3-methylpyrrole-2,4-diyl)bis(carbonylimino))bis(4-hydroxy-8-methyl-7-((tetrahydro-3,4-dihydroxy-5-methoxy-6,6-dimethylpyran-2-yl)oxy)coumarin)
  • BRN 0470805
  • Coumamycin
  • Coumamycin (VAN)
  • Coumamycine
  • Coumamycine [INN-French]
  • Coumamycinum
  • Coumamycinum [INN-Latin]
  • Coumermycin
  • Coumermycin A1
  • Cumamicina
  • Cumamicina [INN-Spanish]
  • Cumamycinum
  • Notomycin
  • Notomycin A1
  • NSC 107412
  • Sugordomycin D-1a
  • Sugordomycin D-la
  • UNII-PCH9QZ1IIH

Systematic Names

  • 1H-Pyrrole-2-carboxylic acid, 5-methyl-, diester with N,N'-bis(7-((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy)-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl)-3-methyl-1H-pyrrole-2,4-dicarboxamide
  • Pyrrole-2-carboxylic acid, 5-methyl-, diester with 3,3'-((3-methylpyrrole-2,4-diyl)bis(carbonylimino))bis(7-((5,5-di-C-methyl-4-O-methyl-alpha-L-lyxopyranosyl)oxy)-4-hydroxy-8-methylcoumarin)

Registry Numbers

CAS Registry Number

  • 4434-05-3

FDA UNII

  • PCH9QZ1IIH

Other Registry Numbers

  • 11035-12-4
  • 1372-92-5
  • 22260-48-6
  • 22850-02-8
  • 23249-07-2
  • 30418-37-2
  • 30546-09-9

System Generated Number

  • 0004434053

Structure Descriptors

InChI

InChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1

InChIKey

WTIJXIZOODAMJT-DHFGXMAYSA-N

Smiles

CO[C@@H]1[C@@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc3ccc4C(=C(NC(=O)c5c[nH]c(C(=O)NC6=C(O)c7ccc(O[C@@H]8OC(C)(C)[C@H](OC)[C@@H](OC(=O)c9ccc(C)[nH]9)[C@H]8O)c(C)c7OC6=O)c5C)C(=O)Oc4c3C)O)OC1(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 500mg/kg (500mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 147, 1978.
mouse LD50 intraperitoneal 159mg/kg (159mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 147, 1978.
mouse LD50 intravenous 25mg/kg (25mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 147, 1978.
mouse LD50 oral 2gm/kg (2000mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 147, 1978.
mouse LD50 subcutaneous 250mg/kg (250mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 786, 1965.