5-hydroxy-2'-deoxyuridine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

5-Hydroxy-2'-deoxyuridine (5-OH-dUrd) is a modified nucleoside that is an important intermediate in the biosynthesis of thymidine. It is formed by the reduction of 5-hydroxyuridine, which is a product of the enzyme thymine hydroxylase. 5-OH-dUrd can then be further reduced to thymidine by the enzyme thymidylate synthase. The synthesis of 5-OH-dUrd involves the hydroxylation of the 5-position of deoxyuridine by the enzyme thymine hydroxylase. This enzyme is found in many organisms, including bacteria, fungi, and mammals. 5-OH-dUrd is also a substrate for the enzyme thymidylate synthase, which converts it to thymidine. Thymidine is an essential building block for DNA synthesis. 5-OH-dUrd is studied because it is a key intermediate in the biosynthesis of thymidine. Understanding the synthesis and metabolism of 5-OH-dUrd is important for understanding the regulation of DNA synthesis. It also has the potential to be used as a therapeutic agent for the treatment of cancer. 5-OH-dUrd has been shown to inhibit the growth of cancer cells by blocking the synthesis of DNA. '

5-hydroxy-2'-deoxyuridine: a major oxidation product of 2'-deoxycytidine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	96622
CHEMBL ID	223557
SCHEMBL ID	530100
MeSH ID	M0200128

Synonyms (23)

Synonym
5-hydroxy-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1h-pyrimidine-2,4-dione
5-hydroxy-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
5168-36-5
CHEMBL223557
5-hydroxy-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
2'-deoxy-5-hydroxyuridine
uridine, 2'-deoxy-5-hydroxy-
5-hydroxy-2'-deoxyuridine
oh-5-du
nsc 82265
SCHEMBL530100
UIJSURSVLVISBO-UBKIQSJTSA-N
5-hydroxy-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
HY-130801
5-hydroxy-2-deoxyuridine
mfcd00057414
5-ohdu
CS-0114103
MS-23451
A930124
STARBLD0009508
PD157353
AKOS040744150

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay ID	Title	Year	Journal	Article
AID1135597	Antiviral activity against Herpes simplex virus 1 KOS infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity	1978	Journal of medicinal chemistry, Feb, Volume: 21, Issue:2	5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID458877	Cytotoxicity against human MT4 cells by MTT assay	2010	Journal of medicinal chemistry, Feb-25, Volume: 53, Issue:4	5-Modified-2'-dU and 2'-dC as mutagenic anti HIV-1 proliferation agents: synthesis and activity.
AID280941	Cytotoxicity against mouse L1210/0 cells after 48 hrs	2007	Journal 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.
AID458874	Antiviral activity against HIV1 LAI in human CEM-SS cells assessed as RT activity after 5 days by single passage assay	2010	Journal of medicinal chemistry, Feb-25, Volume: 53, Issue:4	5-Modified-2'-dU and 2'-dC as mutagenic anti HIV-1 proliferation agents: synthesis and activity.
AID458876	Antiviral activity against HIV1 3B in human MT4 cells assessed as RT activity after 5 days by single passage assay	2010	Journal of medicinal chemistry, Feb-25, Volume: 53, Issue:4	5-Modified-2'-dU and 2'-dC as mutagenic anti HIV-1 proliferation agents: synthesis and activity.
AID1135595	Antiviral activity against Vaccinia virus infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity	1978	Journal of medicinal chemistry, Feb, Volume: 21, Issue:2	5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID1135596	Antiviral activity against Vaccinia virus infected in human skin fibroblasts primed with interferon and superinduced with cyclohexamide and actinomycin D assessed as inhibition of virus-induced cytopathogenicity	1978	Journal of medicinal chemistry, Feb, Volume: 21, Issue:2	5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID458875	Cytotoxicity against human CEM-SS cells by MTT assay	2010	Journal of medicinal chemistry, Feb-25, Volume: 53, Issue:4	5-Modified-2'-dU and 2'-dC as mutagenic anti HIV-1 proliferation agents: synthesis and activity.
AID1135598	Antiviral activity against Herpes simplex virus 1 KOS infected in human skin fibroblasts primed with interferon and superinduced with cyclohexamide and actinomycin D assessed as inhibition of virus-induced cytopathogenicity	1978	Journal of medicinal chemistry, Feb, Volume: 21, Issue:2	5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (10.00)	18.7374
1990's	5 (50.00)	18.2507
2000's	3 (30.00)	29.6817
2010's	1 (10.00)	24.3611
2020's	0 (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: 12.52

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.

Metric	This Compound (vs All)
Research Demand Index	12.52 (24.57)
Research Supply Index	2.40 (2.92)
Research Growth Index	4.92 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.52)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	10 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
adenine [no description available]	1.99	1	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cytosine [no description available]	1.99	1	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2.02	1	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.03	1	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
thymidine [no description available]	1.99	1	pyrimidine 2'-deoxyribonucleoside	Escherichia 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.	2.03	1	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; radiosensitizing agent
idoxuridine [no description available]	2.38	2	organoiodine compound; pyrimidine 2'-deoxyribonucleoside	antiviral drug; DNA synthesis inhibitor
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.	2.03	1	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
cytarabine [no description available]	2.03	1	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
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.	2.03	1	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; EC 2.1.1.45 (thymidylate synthase) inhibitor
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	2.42	2	imidazolidine-2,4-dione
deoxycytidine [no description available]	3.09	5	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
deoxyuridine [no description available]	3.38	7	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
vidarabine adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.	1.95	1	beta-D-arabinoside; purine nucleoside	antineoplastic agent; bacterial metabolite; nucleoside antibiotic
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.05	1	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
adefovir adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.	2.03	1	6-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]	2.03	1
thymine arabinoside thymine arabinoside: selectively inhibits replication of herpes simplex virus	2.03	1	N-glycosyl compound
edoxudin [no description available]	2.03	1	pyrimidine 2'-deoxyribonucleoside
isodialuric acid isodialuric acid: structure given in first source. 5,6-dihydroxyuracil : A nucleobase analogue that is uracil substituted at positions 5 and 6 by hydroxy groups.	7.02	1	hydroxypyrimidine; nucleobase analogue; pyrimidone	Mycoplasma genitalium metabolite
n-(2-(hydroxyethoxy)methyl)-5-methyluracil N-(2-(hydroxyethoxy)methyl)-5-methyluracil: structure given in first source	2.03	1
5-fluoro-1-((2-hydroxyethoxy)methyl)uracil 5-fluoro-1-((2-hydroxyethoxy)methyl)uracil: structure given in first source	2.03	1
5-hydroxymethyl-2'-deoxyuridine [no description available]	2.45	2	pyrimidine 2'-deoxyribonucleoside
msh release-inhibiting hormone [no description available]	2.03	1	oligopeptide
5-formyl-2'-deoxyuridine 5-formyl-2'-deoxyuridine: structure given in first source	2.03	1
propynyloxy-2'-deoxyuridine propynyloxy-2'-deoxyuridine: RN given refers to parent cpd	6.95	1
8-oxo-dado 2'-deoxy-7,8-dihydro-8-oxoadenosine: structure given in first source	1.99	1
5-nitro-2'-deoxyuridine [no description available]	2.03	1
5-vinyl-2'-deoxyuridine 5-vinyl-2'-deoxyuridine: structure	2.03	1
5-propyl-2'-deoxyuridine 5-propyl-2'-deoxyuridine: RN given refers to parent cpd	2.03	1
5-hydroxymethyldeoxycytidine monophosphate 5-hydroxymethyl-2'-deoxycytidine: structure in first source	2.05	1
dialuric acid dialuric acid: RN given refers to parent cpd; structure. dialuric acid : A member of the class of barbiturates that is barbituric acid in which a hydrogen attached to a ring carbon is replaced by a hydroxy group.	7.02	1	barbiturates
adenosine-5'-carboxaldehyde adenosine-5'-carboxaldehyde: potent inhibitor of S-adenosyl-L-homocysteine hydrolase; structure given in first source. 5'-dehydroadenosine : A member of the class of adenosines that is 5'-dehydro derivative of adenosine.	2.03	1	adenosines
brivudine brivudine: anti-herpes agent	2.03	1
5-ethynyl-2'-deoxyuridine 5-ethynyl-2'-deoxyuridine: structure in first source	2.03	1
5-hydroxy-2'-deoxycytidine 5-hydroxy-2'-deoxycytidine: a major oxidation product of 2'-deoxycytidine	3.09	5
5-cyano-2'-deoxyuridine 5-cyano-2'-deoxyuridine: structure in first source	2.03	1
5-(2-iodovinyl)-2'-deoxyuridine [no description available]	2.03	1
oligonucleotides [no description available]	6.99	1
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2.03	1	2-aminopurines; oxopurine	antimetabolite; antiviral drug
deoxyguanosine [no description available]	1.99	1	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
9-((2-phosphonylmethoxy)ethyl)guanine 9-((2-phosphonylmethoxy)ethyl)guanine: structure given in first source	2.03	1	phosphoethanolamine
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	1.99	1	guanosines	biomarker

Condition	Indicated	Relationship Strength	Studies	Trials
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	0	1.99	1	0
Leukemia L 1210 [description not available]	0	1.99	1	0

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