Page last updated: 2024-09-27

5-cyano-2'-deoxyuridine

Description

5-cyano-2'-deoxyuridine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID493224
CHEMBL ID373885
SCHEMBL ID336438
MeSH IDM0416326

Synonyms (11)

Synonym
1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile
5-cn-2'-durd
5-cyano-durd
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2,4-dioxo-pyrimidine-5-carbonitrile
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidine-5-carbonitrile
CHEMBL373885 ,
bdbm50000967
26639-00-9
SCHEMBL336438
DTXSID90333233
5-cyano-2'-deoxyuridine

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine phosphorylaseHomo sapiens (human)Km49.00000.16000.16000.1600AID211066
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
mitochondrial genome maintenanceThymidine phosphorylaseHomo sapiens (human)
angiogenesisThymidine phosphorylaseHomo sapiens (human)
pyrimidine nucleobase metabolic processThymidine phosphorylaseHomo sapiens (human)
pyrimidine nucleoside metabolic processThymidine phosphorylaseHomo sapiens (human)
chemotaxisThymidine phosphorylaseHomo sapiens (human)
signal transductionThymidine phosphorylaseHomo sapiens (human)
cell differentiationThymidine phosphorylaseHomo sapiens (human)
regulation of myelinationThymidine phosphorylaseHomo sapiens (human)
dTMP catabolic processThymidine phosphorylaseHomo sapiens (human)
regulation of transmission of nerve impulseThymidine phosphorylaseHomo sapiens (human)
regulation of gastric motilityThymidine phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
1,4-alpha-oligoglucan phosphorylase activityThymidine phosphorylaseHomo sapiens (human)
protein bindingThymidine phosphorylaseHomo sapiens (human)
growth factor activityThymidine phosphorylaseHomo sapiens (human)
thymidine phosphorylase activityThymidine phosphorylaseHomo sapiens (human)
protein homodimerization activityThymidine phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
cytosolThymidine phosphorylaseHomo sapiens (human)
cytosolThymidine phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID280941Cytotoxicity against mouse L1210/0 cells after 48 hrs2007Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7
Probing the anticancer activity of nucleoside analogues: a QSAR model approach using an internally consistent training set.
AID1136933Inhibition of Escherichia coli B thymidine kinase using [2-14C]-thymidine as substrate assessed as formation of [14C]-TMP at 2 mM after 10 mins by liquid scintillation spectrometric analysis relative to control1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
Design of species- or isozyme-specific enzyme inhibitors. 2. Differences between a bacterial and a mammalian thymidine kinase in the effect of thymidine substituents on affinity for the thymidine site.
AID1135480Antiviral activity against Vaccinia virus infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridine.
AID1124544Competitive inhibition of thymidine kinase in BHK21 (C13) cells using thymidine as substrate assessed as formation of TMP by Lineweaver-Burk plot analysis1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase.
AID1135478Antiviral activity against Vaccinia virus infected in human skin fibroblasts assessed as inhibition of virus-induced cytopathogenicity1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridine.
AID232840Ratio of Vmax to that of dThd (Vmax = 0.14)1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
Thymidine phosphorylase. Substrate specificity for 5-substituted 2'-deoxyuridines.
AID1135479Antiviral activity against Herpes simplex virus 1 infected in human skin fibroblasts assessed as inhibition of virus-induced cytopathogenicity1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridine.
AID1135481Antiviral activity against Herpes simplex virus 1 infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridine.
AID270072Antileishmanial activity against Leishmania donovani LV9 promastigotes by MTT method2006Bioorganic & medicinal chemistry letters, Oct-01, Volume: 16, Issue:19
Structurally diverse 5-substituted pyrimidine nucleosides as inhibitors of Leishmania donovani promastigotes in vitro.
AID156400Concentration required to inhibit incorporation of [1,'2'-3H]dUrd into DNA of primary rabbit kidney (PRK) cells by 50%1981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
AID211066Michaelis-Menten constant (Km) against horse liver thymidine phosphorylase1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
Thymidine phosphorylase. Substrate specificity for 5-substituted 2'-deoxyuridines.
AID156514Concentration required to inhibit incorporation of [Me-3H]-dThd into DNA of primary rabbit kidney (PRK) cells by 50%1981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
AID1136932Inhibition of Escherichia coli B thymidine kinase using [2-14C]-thymidine as substrate assessed as formation of [14C]-TMP at 0.5 mM after 10 mins by liquid scintillation spectrometric analysis relative to control1979Journal of medicinal chemistry, Dec, Volume: 22, Issue:12
Design of species- or isozyme-specific enzyme inhibitors. 2. Differences between a bacterial and a mammalian thymidine kinase in the effect of thymidine substituents on affinity for the thymidine site.
AID1135483Dissociation constant, pKa of the compound by spectrophotometric analysis1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (50.00)18.7374
1990's0 (0.00)18.2507
2000's4 (40.00)29.6817
2010's1 (10.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]