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4-amino-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile


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Chemical Component Summary

Name4-amino-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
SynonymsTOYOCAMYCIN
Identifiers4-azanyl-7-[(2R,3R,4S,5R)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
FormulaC12 H13 N5 O4
Molecular Weight291.263
TypeNON-POLYMER
Isomeric SMILESc1c(c2c(ncnc2n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)C#N
InChIInChI=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
InChIKeyXOKJUSAYZUAMGJ-WOUKDFQISA-N

Chemical Details

Formal Charge0
Atom Count34
Chiral Atom Count4
Bond Count36
Aromatic Bond Count10

Drug Info: DrugBank

DrugBank IDDB13916 
NameToyocamycin
Groups experimental
Description4-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.
Synonyms
  • Siromycin
  • Cyanotubericidin
  • 7-deaza-7-cyanoadenosine
  • Toyocamycin
  • 4-amino-5-cyano-7-(D-ribofuranosyl)-7H-pyrrolo(2,3-d)pyrimidine
Categories
  • Antibiotics, Antineoplastic
  • Antimetabolites
  • Antineoplastic Agents
  • Noxae
  • Nucleic Acids, Nucleotides, and Nucleosides
CAS number606-58-6

Related Resource References

Resource NameReference
PubChem 11824
ChEMBL CHEMBL99668
ChEBI CHEBI:134606
CCDC/CSD TOYOCM10