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Substance Name: Nogalamycin [USAN:INN]
RN: 1404-15-5
UNII: L059DCD6IP
InChIKey: KGTDRFCXGRULNK-JYOBTZKQSA-N

Note

  • An anthrocycline from a Streptomyces nogalater variant. It is a cytolytic antineoplastic that inhibits DNA-dependent RNA synthesis by binding to DNA.

Molecular Formula

  • C39-H49-N-O16

Molecular Weight

  • 787.8071
 

Classification Codes

  • Antibiotics, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Indicators and Reagents
  • Intercalating Agents
  • Mutation Data
  • Natural Product
  • Nucleic Acid Synthesis Inhibitors
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Names and Synonyms

Name of Substance

  • Nogalamycin
  • Nogalamycin [USAN:INN]

MeSH Heading

  • Nogalamycin

Synonyms

  • Antibiotic 205t3
  • Antibiotic from Streptomyces nogalater
  • Antibiotic NSC 70845
  • Methyl 11-((6-desoxy-3-C-methyl-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy)-4-dimethylamino-3,4,5,6,9,11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-2,6-epoxy-2H-naphthaceno(1,2-b)-oxocin-14-carboxylat
  • Nogalamicina
  • Nogalamicina [INN-Spanish]
  • Nogalamycin
  • Nogalamycine
  • Nogalamycine [INN-French]
  • Nogalamycinum
  • Nogalamycinum [INN-Latin]
  • Nogalamyicn
  • Nogalomycin
  • NSC 70845
  • NSC-70845
  • U 15167
  • U-15167
  • UNII-L059DCD6IP

Systematic Names

  • 2,6-Epoxy-2H-naphthaceno(1,2-b)oxocin-14-carboxylic acid, 11-((6-deoxy-3-C-methyl-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy)-4-(dimethylamino)-3,4,5,6,9,11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-, methyl ester, (2R-(2alpha,3beta,4alpha,5beta,6alpha,11beta,13alpha,14alpha))-
  • Nogalamycin

Registry Numbers

CAS Registry Number

  • 1404-15-5

FDA UNII

  • L059DCD6IP

Other Registry Numbers

  • 11076-70-3
  • 1263312-59-9

System Generated Number

  • 0001404155

Structure Descriptors

InChI

1S/C39H49NO16/c1-14-32(49-7)39(4,52-10)33(50-8)36(53-14)54-19-13-37(2,48)24(34(47)51-9)15-11-16-21(27(43)20(15)19)28(44)22-18(41)12-17-30(23(22)26(16)42)55-35-29(45)25(40(5)6)31(46)38(17,3)56-35/h11-12,14,19,24-25,29,31-33,35-36,41,43,45-46,48H,13H2,1-10H3/t14-,19-,24-,25-,29-,31+,32-,33-,35+,36-,37-,38+,39+/m0/s1

InChIKey

KGTDRFCXGRULNK-JYOBTZKQSA-N

Smiles

C[C@H]1[C@@H]([C@@]([C@H]([C@@H](O1)O[C@H]2C[C@]([C@@H](c3c2c(c4c(c3)C(=O)c5c(c(cc6c5O[C@H]7[C@H]([C@@H]([C@H]([C@@]6(O7)C)O)N(C)C)O)O)C4=O)O)C(=O)OC)(C)O)OC)(C)OC)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 250ug/kg (0.25mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Progress Report Submitted to the National Cancer Insitute by Piason Research Institute.Vol. -, Pg. 192, 1966.
mouse LD50 intraperitoneal 13750ug/kg (13.75mg/kg)   Indian Journal of Experimental Biology. Vol. 17, Pg. 595, 1979.
mouse LD50 oral > 300mg/kg (300mg/kg)   Progress Report Submitted to the National Cancer Insitute by Piason Research Institute.Vol. -, Pg. 192, 1966.
mouse LDLo intravenous 8500ug/kg (8.5mg/kg) SKIN AND APPENDAGES (SKIN): OTHER GLANDS: OTHER Progress Report Submitted to the National Cancer Insitute by Piason Research Institute.Vol. -, Pg. 192, 1966.
rat LD50 intraperitoneal 500ug/kg (0.5mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.
rat LDLo intravenous 4600ug/kg (4.6mg/kg) GASTROINTESTINAL: OTHER CHANGES

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Progress Report Submitted to the National Cancer Insitute by Piason Research Institute.Vol. -, Pg. 192, 1966.