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Substance Name: Toyocamycin
RN: 606-58-6
UNII: L7995C4D7F
InChIKey: XOKJUSAYZUAMGJ-WOUKDFQISA-N

Note

  • 4-Amino-5-cyano-7-(D-ribofuranosyl)-7H- pyrrolo(2,3-d)pyrimidine. Antibiotic antimetabolite isolated from Streptomyces toyocaensis cultures. It is an analog of adenosine, blocks RNA synthesis and ribosome function, and is used mainly as a tool in biochemistry.

Molecular Formula

  • C12-H13-N5-O4

Molecular Weight

  • 291.2657
 

Classification Codes

  • Antibiotics, Antineoplastic
  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Mutation Data
  • Natural Product
  • Noxae
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Names and Synonyms

Name of Substance

  • Toyocamycin

MeSH Heading

  • Toyocamycin

Synonyms

  • 4-26-00-01419 (Beilstein Handbook Reference)
  • 4-Amino-5-cyano-7-(D-ribofuranosyl)-7H-pyrrolo(2,3-d)pyrimidine
  • 4-Amino-7-beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile
  • 7-Deaza-7-cyanoadenosine
  • A-399-Y4
  • Ahygroscopin-B
  • Antibiotic 1037
  • Antibiotic A-399-Y4
  • Antibiotic E212
  • B 181008
  • BRN 0048454
  • Cyanotubericidin
  • E-212
  • E-212-1
  • Naritheracin
  • NSC 63701
  • NSC 99843
  • NSC-63701
  • Siromycin
  • Toyocamycin
  • Toyocamycin nucleoside
  • Unamycin-B
  • UNII-L7995C4D7F
  • Uramycin B
  • Vengicide

Systematic Name

  • 7H-Pyrrolo(2,3-d)pyrimidine-5-carbonitrile, 4-amino-7-beta-D-ribofuranosyl-

Registry Numbers

CAS Registry Number

  • 606-58-6

FDA UNII

  • L7995C4D7F

System Generated Number

  • 0000606586

Structure Descriptors

InChI

InChI=1S/C12H13N5O4/c13-1-5-2-17(11-7(5)10(14)15-4-16-11)12-9(20)8(19)6(3-18)21-12/h2,4,6,8-9,12,18-20H,3H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1

InChIKey

XOKJUSAYZUAMGJ-WOUKDFQISA-N

Smiles

Nc1ncnc2c1c(cn2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C#N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 20mg/kg (20mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 315, 1981.
mouse LD50 intravenous 1500ug/kg (1.5mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 318, 1981.
mouse LD50 oral 8mg/kg (8mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 805, 1967.
mouse LDLo subcutaneous 10mg/kg (10mg/kg)   Journal of Antibiotics, Series A. Vol. 9, Pg. 60, 1956.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 243 deg C   EXP
log P (octanol-water) -0.420 (none)   EST
Atmospheric OH Rate Constant 1.88E-10 cm3/molecule-sec 25 EST

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