Page last updated: 2024-09-24

5-formyl-2'-deoxyuridine

Description

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

Cross-References

ID SourceID
PubMed CID98561
CHEMBL ID379296
SCHEMBL ID337091
MeSH IDM0170574

Synonyms (24)

Synonym
5-formyl-2'-deoxyuridine
uridine, 2'-deoxy-5-formyl-
ccris 6343
nsc 148297
5-pyrimidinecarboxaldehyde, 1,2,3,4-tetrahydro-1-(2-deoxy-beta-d-ribofuranosyl)-2,4-dioxo-
1,2,3,4-tetrahydro-1-(2-deoxy-beta-d-ribofuranosyl)-2,4-dioxo-5-pyrimidinecarboxaldehyde
4494-26-2
5-pyrimidinecarboxaldehyde, 1-(2-deoxy-beta-d-erythro-pentofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxo-
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2,4-dioxo-pyrimidine-5-carbaldehyde
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidine-5-carbaldehyde
CHEMBL379296
2'-deoxy-5-formyluridine
1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde
5-formyldeoxyuridine
SCHEMBL337091
AKOS022172827
MVORBLZUGBSUNB-XLPZGREQSA-N
AC-32343
mfcd01689820
A872444
1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde;5-formyl-du
BS-18944
CS-0452613
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine phosphorylaseHomo sapiens (human)Km125.00000.16000.16000.1600AID211066
[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 (23)

Assay IDTitleYearJournalArticle
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.
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.
AID156549Concentration required to reduce HSV-1 KOS virus induced cytogenicity in primary rabbit kidney (PRK); Range is 1-21980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
AID270074Antiviral activity against cowpox virus2006Bioorganic & medicinal chemistry letters, Oct-01, Volume: 16, Issue:19
Structurally diverse 5-substituted pyrimidine nucleosides as inhibitors of Leishmania donovani promastigotes in vitro.
AID156557Concentration required to reduce [Me-H]dThd incorporation into DNA in primary rabbit kidney (PRK)1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
AID270073Antiviral activity against vaccinia virus2006Bioorganic & medicinal chemistry letters, Oct-01, Volume: 16, Issue:19
Structurally diverse 5-substituted pyrimidine nucleosides as inhibitors of Leishmania donovani promastigotes in vitro.
AID156547Concentration required to reduce HSV-1 F virus induced cytogenicity in primary rabbit kidney (PRK); Range is 1-21980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
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.
AID265923Antiviral activity against cowpox virus Brighton by plaque reduction in HFF cells2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
5-(Dimethoxymethyl)-2'-deoxyuridine: a novel gem diether nucleoside with anti-orthopoxvirus activity.
AID156697Minimum Cytotoxic concentration in primary rabbit kidney (PRK)1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
AID229758Ratio of ID50 for [Me-H]dThd to ID50 for [1,2-H]dUrd1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
AID156556Concentration required to reduce [1,2-H]dUrd incorporation into DNA in primary rabbit kidney (PRK)1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
AID156550Concentration required to reduce HSV-1 McIntyre virus induced cytogenicity in primary rabbit kidney (PRK)1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
AID156552Concentration required to reduce HSV-2 Lyons virus induced cytogenicity in primary rabbit kidney (PRK); Range is 2-41980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
AID156683Concentration required to reduce virus HSV-2G induced cytogenicity in primary rabbit kidney (PRK); Range is 1-21980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
AID156680Concentration required to reduce vaccinia virus induced cytogenicity in primary rabbit kidney (PRK); Range is 0.1-0.21980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
AID265924Cytotoxicity against HFF cell line by neutral red toxicity assay2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
5-(Dimethoxymethyl)-2'-deoxyuridine: a novel gem diether nucleoside with anti-orthopoxvirus activity.
AID82318Growth inhibition against HL-60 after 72 hours incubation period1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Nucleosides. 150. Synthesis and some biological properties of 5-monofluoromethyl, 5-difluoromethyl, and 5-trifluoromethyl derivatives of 2'-deoxyuridine and 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyluracil.
AID265922Antiviral activity against cowpox virus Brighton measured as cytopathogenicity in HFF cells2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
5-(Dimethoxymethyl)-2'-deoxyuridine: a novel gem diether nucleoside with anti-orthopoxvirus activity.
AID265920Antiviral activity against vaccinia virus Copenhagen measured as cytopathogenicity in HFF cells2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
5-(Dimethoxymethyl)-2'-deoxyuridine: a novel gem diether nucleoside with anti-orthopoxvirus activity.
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.
AID156554Concentration required to reduce HV2 196 virus induced cytogenicity in primary rabbit kidney (PRK); Range is 1-41980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Oxime and dithiolane derivatives of 5-formyl-2'-deoxyuridine and their 5'-phosphates: antiviral effects and thymidylate synthetase inhibition.
AID265921Antiviral activity against vaccinia virus Copenhagen assessed as plaque reduction in HFF cells2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
5-(Dimethoxymethyl)-2'-deoxyuridine: a novel gem diether nucleoside with anti-orthopoxvirus activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (41)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (9.76)18.7374
1990's6 (14.63)18.2507
2000's16 (39.02)29.6817
2010's13 (31.71)24.3611
2020's2 (4.88)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%
Other44 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (1)

ArticleYear
5-Formyluracil and its nucleoside derivatives confer toxicity and mutagenicity to mammalian cells by interfering with normal RNA and DNA metabolism.
Toxicology letters, Feb-03, Volume: 119, Issue: 1
2001
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]