Compounds > 5-nitro-2'-deoxyuridine
Page last updated: 2024-09-25

5-nitro-2'-deoxyuridine

Cross-References

ID SourceID
PubMed CID145681
CHEMBL ID195535
SCHEMBL ID5154444
MeSH IDM0065728

Synonyms (12)

Synonym
5-nitro-durd
1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-nitro-1h-pyrimidine-2,4-dione
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-nitro-pyrimidine-2,4-dione
CHEMBL195535
uridine, 2'-deoxy-5-nitro-
5-nitro-2'-deoxyuridine
2'-deoxy-5-nitrouridine
3106-01-2
SCHEMBL5154444
USBZWPXQQCSGAV-RRKCRQDMSA-N
5-nitro-deoxyuridine
DTXSID50185018

Protein Targets (3)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)Km0.16000.16001.60674.5000AID363300
Thymidine phosphorylaseHomo sapiens (human)Km80.08000.16000.16000.1600AID239741; AID363300
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

Processvia Protein(s)Taxonomy
DNA damage responseThymidine phosphorylaseEscherichia coli K-12
pyrimidine nucleobase metabolic processThymidine phosphorylaseEscherichia coli K-12
pyrimidine nucleoside metabolic processThymidine phosphorylaseEscherichia coli K-12
thymidine metabolic processThymidine phosphorylaseEscherichia coli K-12
negative regulation of endothelial cell proliferationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukocyte chemotaxis involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukocyte migration involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene production involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene metabolic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
humoral immune responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of angiogenesisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
positive regulation of bone mineralizationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
dendritic cell migrationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
glucose homeostasisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
long-chain fatty acid biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of fat cell differentiationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of insulin secretionPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of vascular wound healingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of wound healingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of inflammatory response to woundingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of cytokine production involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of cellular response to oxidative stressPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene A4 biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of reactive oxygen species biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of response to endoplasmic reticulum stressPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of sprouting angiogenesisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
positive regulation of leukocyte adhesion to arterial endothelial cellPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipoxin biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
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 (12)

Processvia Protein(s)Taxonomy
1,4-alpha-oligoglucan phosphorylase activityThymidine phosphorylaseEscherichia coli K-12
thymidine phosphorylase activityThymidine phosphorylaseEscherichia coli K-12
glycosyltransferase activityThymidine phosphorylaseEscherichia coli K-12
pentosyltransferase activityThymidine phosphorylaseEscherichia coli K-12
arachidonate 5-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonate 12(S)-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
iron ion bindingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
protein bindingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
hydrolase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
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 (12)

Processvia Protein(s)Taxonomy
cytosolThymidine phosphorylaseEscherichia coli K-12
membraneThymidine phosphorylaseEscherichia coli K-12
cytosolThymidine phosphorylaseEscherichia coli K-12
extracellular regionPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
extracellular spacePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelopePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelope lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nucleoplasmPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
cytosolPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear matrixPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear membranePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
secretory granule lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
perinuclear region of cytoplasmPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
ficolin-1-rich granule lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelopePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
cytosolThymidine phosphorylaseHomo sapiens (human)
cytosolThymidine phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID242904Vmax against human thymidine phosphorylase2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID243054Ratio of Kcat to Km against human thymidine phosphorylase2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID98022Effective concentration to inhibit growth of L1210 cells in culture1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Mechanism of action of 5-nitro-2'-deoxyuridine.
AID239741Michaelis-Menten constant against human thymidine phosphorylase2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID98524Ability to inhibit the proliferation or tumor cell growth by 50% of the murine leukemia L1210 cells was determined1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
5-Quinone derivatives of 2'-deoxyuridine 5'-phosphate: inhibition and inactivation of thymidylate synthase, antitumor cell, and antiviral studies.
AID242906Vmax against Escherichia coli thymidine phosphorylase2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID242916Catalytic constant against Escherichia coli thymidine phosphorylase2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID202933Effective concentration to inhibit growth of S49 cells in culture1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Mechanism of action of 5-nitro-2'-deoxyuridine.
AID202932Effective concentration for growth inhibition of S49 cells in culture in the presence of 10 uM of dUrd1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Mechanism of action of 5-nitro-2'-deoxyuridine.
AID242915Catalytic constant against human thymidine phosphorylase2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID239752Michaelis-Menten constant against Escherichia coli thymidine phosphorylase2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID98021Effective concentration for growth inhibition of L1210 cells in culture in the presence of 10 uM of dUrd1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Mechanism of action of 5-nitro-2'-deoxyuridine.
AID363299Activity of Escherichia coli thymidine phosphorylase2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors.
AID243088Ratio of Kcat to Km for Escherichia coli thymidine phosphorylase2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID363300Activity of human thymidine phosphorylase2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors.
AID98020Effective concentration for growth inhibition of L1210 cells in culture in the presence of 10 uM of dThd1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Mechanism of action of 5-nitro-2'-deoxyuridine.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (66.67)18.7374
1990's0 (0.00)18.2507
2000's3 (33.33)29.6817
2010's0 (0.00)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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
idoxuridine[no description available]medium20organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
bromodeoxyuridine[no description available]medium20pyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
thymidine[no description available]medium30pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
6-amino-5-bromouracil[no description available]medium20
5-chloro-6-(1-(2-iminopyrrolidinyl) methyl)uracil hydrochloride[no description available]medium20hydrochloride;
iminium salt		antineoplastic agent;
EC 2.4.2.4 (thymidine phosphorylase) inhibitor
sesone[no description available]medium20
fluorouracil[no description available]medium10nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
floxuridine[no description available]medium10nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
cytarabine[no description available]medium10beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
trifluridine[no description available]medium10nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
EC 2.1.1.45 (thymidylate synthase) inhibitor
adefovir[no description available]medium106-aminopurines;
ether;
phosphonic acids		antiviral drug;
DNA synthesis inhibitor;
drug metabolite;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent
9-(2-phosphonylmethoxyethyl)-2,6-diaminopurine[no description available]medium10
thymine arabinoside[no description available]medium10N-glycosyl compound
edoxudin[no description available]medium10pyrimidine 2'-deoxyribonucleoside
n-(2-(hydroxyethoxy)methyl)-5-methyluracil[no description available]medium10
5-fluoro-1-((2-hydroxyethoxy)methyl)uracil[no description available]medium10
5-hydroxymethyl-2'-deoxyuridine[no description available]medium10pyrimidine 2'-deoxyribonucleoside
msh release-inhibiting hormone[no description available]medium10oligopeptide
5-hydroxy-2'-deoxyuridine[no description available]medium10
5-formyl-2'-deoxyuridine[no description available]medium10
5-vinyl-2'-deoxyuridine[no description available]medium10
5-propyl-2'-deoxyuridine[no description available]medium10
adenosine-5'-carboxaldehyde[no description available]medium10adenosines
brivudine[no description available]medium10
5-ethynyl-2'-deoxyuridine[no description available]medium10
5-cyano-2'-deoxyuridine[no description available]medium10
5-(2-iodovinyl)-2'-deoxyuridine[no description available]medium10
acyclovir[no description available]medium102-aminopurines;
oxopurine		antimetabolite;
antiviral drug
9-((2-phosphonylmethoxy)ethyl)guanine[no description available]medium10phosphoethanolamine
xanthine[no description available]medium10xanthineSaccharomyces cerevisiae metabolite
5-bromocytosine[no description available]medium10
3,n(4)-ethanocytosine[no description available]medium10organic heterobicyclic compoundmutagen
deoxyuridine[no description available]medium50pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
5-nitro-2'-deoxyuridine 5'-monophosphate[no description available]medium10
uracil[no description available]medium20pyrimidine nucleobase;
pyrimidone		allergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
prodrug;
Saccharomyces cerevisiae metabolite
uridine[no description available]medium10uridinesdrug metabolite;
fundamental metabolite;
human metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 12100low20
Leukemia L12100low20