Compounds > 5-(1-propenyl)-2'-deoxyuridine
Page last updated: 2024-11-11

5-(1-propenyl)-2'-deoxyuridine

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Description

5-(1-propenyl)-2'-deoxyuridine: has anti-herpes activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6440090
CHEMBL ID2367811
CHEMBL ID31277
MeSH IDM0101119

Synonyms (21)

Synonym
2'-deoxy-5-(1-propenyl)uridine
(e)-5-(1-propenyl)-durd
66270-29-9
4-hydroxy-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-[(e)-prop-1-enyl]pyrimidin-2-one
4-hydroxy-1-((2r,4s,5r)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(e)-propenyl-1h-pyrimidin-2-one
2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-beta-d-erythro-pentofuranosyl)-5-[(1e)-1-propenyl]-
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-[(e)-prop-1-enyl]pyrimidine-2,4-dione
(e)-5-(1-propenyl)-2'-deoxyuridine
(e)-5-(1-propenyl)deoxyuridine
(e)-2'-deoxy-5-(1-propenyl)uridine
5-(1-propenyl)-2'-deoxyuridine
brn 5758016
uridine, 2'-deoxy-5-(1-propenyl)-, (e)-
bdbm50028584
chembl2367811 ,
1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-propenyl-1h-pyrimidine-2,4-dione(bvdu)
1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-propenyl-1h-pyrimidine-2,4-dione
chembl31277
4-hydroxy-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-propenyl-1h-pyrimidin-2-one
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(e)-prop-1-enyl]pyrimidine-2,4-dione
e-5-propenyl-2'-deoxyuridine
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase, cytosolic Rattus norvegicus (Norway rat)Ki8,005.00002.40004.20006.5000AID126598; AID210886
[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)Km314.00000.16000.16000.1600AID211066
[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 (11)

Assay IDTitleYearJournalArticle
AID84072Compound was evaluated for antiviral activity against HSV-1(strain KOS)1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine and related analogues: potent and unusually selective antiviral activity of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine against herpes simplex virus type 1.
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.
AID126598Non-competitive inhibition against rat mitochondrial thymidine kinase1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes.
AID165523Concentration of compound required to inhibit [1',2'-3H]dUrd incorporation into host cell DNA by 50% in primary rabbit kidney cell cultures1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine and related analogues: potent and unusually selective antiviral activity of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine against herpes simplex virus type 1.
AID84953Compound was evaluated for antiviral activity against HSV-2(strain G)1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine and related analogues: potent and unusually selective antiviral activity of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine against herpes simplex virus type 1.
AID85828Antiviral activity against herpes simplex virus type 1 (HSV-1) determined in baby hamster kidney cells1983Journal of medicinal chemistry, Sep, Volume: 26, Issue:9
Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity.
AID217982Compound was evaluated for antiviral activity against vaccinia1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine and related analogues: potent and unusually selective antiviral activity of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine against herpes simplex virus type 1.
AID165524Concentration of compound required to inhibit [methyl-3H]dThd incorporation into host cell DNA by 50% in primary rabbit kidney cell cultures1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine and related analogues: potent and unusually selective antiviral activity of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine against herpes simplex virus type 1.
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.
AID84071Compound was evaluated for antiviral activity against HSV-1(TK-, strain B2006)1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Synthesis of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine and related analogues: potent and unusually selective antiviral activity of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine against herpes simplex virus type 1.
AID210886Competitive inhibition against rat cytoplasmic Thymidine kinase1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (100.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)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]

Market Indicators

Research Demand Index: 12.50

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.50 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.50)

All Compounds (24.57)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thymidine
[no description available]		2.3620pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
floxuridine
Floxuridine: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.. floxuridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.		1.9510nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
idoxuridine
[no description available]		2.6530organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
uridine
[no description available]		7.3620uridinesdrug metabolite;
fundamental metabolite;
human metabolite
bromodeoxyuridine
Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.		2.3620pyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
cytidine
[no description available]		1.9610cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
trifluridine
Trifluridine: An antiviral derivative of THYMIDINE used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis due to HERPES SIMPLEX virus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p557). trifluridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-trifluoromethyluracil as the nucleobase. An antiviral drug used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis.		2.3620nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
EC 2.1.1.45 (thymidylate synthase) inhibitor
fluorodeoxyuridylate
Fluorodeoxyuridylate: 5-Fluoro-2'-deoxyuridylate. An inhibitor of thymidylate synthetase. Formed from 5-fluorouracil or 5-fluorodeoxyuridine.		1.9610pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
deoxycytidine
[no description available]		1.9610pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
deoxyuridine
[no description available]		7.8740pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
stavudine
Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase		1.9610dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
ibacitabine
ibacitabine: antiherpetic agent		1.9610pyrimidine 2'-deoxyribonucleoside
methylthymidine
methylthymidine: RN given refers to N-3-methylthymidine		1.9610
2',3'-dideoxythymidine
[no description available]		1.9610
5'-amino-2',5'-dideoxythymidine
5'-amino-5'-deoxythymidine: RN given refers to parent cpd		1.9610
5-chloro-2'-deoxyuridine
[no description available]		1.9510
5-(2-propenyl)-2'-deoxyuridine
[no description available]		2.3620
edoxudin
[no description available]		1.9510pyrimidine 2'-deoxyribonucleoside
5-hydroxymethyl-2'-deoxyuridine
[no description available]		1.9510pyrimidine 2'-deoxyribonucleoside
5-formyl-2'-deoxyuridine
5-formyl-2'-deoxyuridine: structure given in first source		1.9510
3'-amino-2',3'-dideoxythymidine
[no description available]		1.9610
5-amino-2'-deoxyuridine
5-amino-2'-deoxyuridine: structure in first source		1.9610
5,6-dihydrothymidine
5,6-dihydrothymidine: RN given refers to cpd without isomeric designation. 5,6-dihydrothymidine : A pyrimidine 2'-deoxyribonucleoside having dihydrothymine as the nucleobase.		1.9610pyrimidine 2'-deoxyribonucleosideMycoplasma genitalium metabolite
5-methyldeoxycytidine
[no description available]		1.96102'-deoxycytidine
brivudine
brivudine: anti-herpes agent		2.6530
5-cyano-2'-deoxyuridine
5-cyano-2'-deoxyuridine: structure in first source		1.9510
5-(2-iodovinyl)-2'-deoxyuridine
5-(2-iodovinyl)-2'-deoxyuridine: RN given refers to cpd without isomeric designation		1.9610
arabinofuranosyluracil
Arabinofuranosyluracil: A pyrimidine nucleoside formed in the body by the deamination of CYTARABINE.		6.9610
ConditionIndicatedRelationship StrengthStudiesTrials
Herpes Simplex Virus Infection
[description not available]		02.3620
Herpes Simplex
A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)		02.3620