TO1

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

Created:	2011-04-22
Last modified:	2020-06-05

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5 entries where TO1 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	34
Chiral Atom Count	4
Bond Count	36
Aromatic Bond Count	10

2D diagram of TO1

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Chemical Component Summary
Name	4-amino-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
Synonyms	TOYOCAMYCIN
Systematic Name (OpenEye OEToolkits)	4-azanyl-7-[(2R,3R,4S,5R)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
Formula	C₁₂ H₁₃ N₅ O₄
Molecular Weight	291.263
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	N#Cc2c1c(ncnc1n(c2)C3OC(C(O)C3O)CO)N
SMILES	CACTVS	3.370	Nc1ncnc2n(cc(C#N)c12)[CH]3O[CH](CO)[CH](O)[CH]3O
SMILES	OpenEye OEToolkits	1.7.2	c1c(c2c(ncnc2n1C3C(C(C(O3)CO)O)O)N)C#N
Canonical SMILES	CACTVS	3.370	Nc1ncnc2n(cc(C#N)c12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
Canonical SMILES	OpenEye OEToolkits	1.7.2	c1c(c2c(ncnc2n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)C#N
InChI	InChI	1.03	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	InChI	1.03	XOKJUSAYZUAMGJ-WOUKDFQISA-N

Drug Info: DrugBank

DrugBank ID	DB13916
Name	Toyocamycin
Groups	experimental
Description	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.
Synonyms	7-deaza-7-cyanoadenosine Uramycin B Vengicide Toyocamycin Cyanotubericidin Siromycin 4-amino-5-cyano-7-(D-ribofuranosyl)-7H-pyrrolo(2,3-d)pyrimidine Ahygroscopin-B
Categories	Antibiotics, Antineoplastic Antimetabolites Antineoplastic Agents Noxae Nucleic Acids, Nucleotides, and Nucleosides Nucleosides Ribonucleosides Toxic Actions
CAS number	606-58-6

Related Resource References

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

RCSB PDB Core Operations are funded by the U.S. National Science Foundation (DBI-2321666), the US Department of Energy (DE-SC0019749), and the National Cancer Institute, National Institute of Allergy and Infectious Diseases, and National Institute of General Medical Sciences of the National Institutes of Health under grant R01GM157729.