Home Other Building Blocks 2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-

2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-

CAS No.:
20636-41-3
Catalog Number:
AG002IH3
Molecular Formula:
C4H4N2O3
Molecular Weight:
128.0862
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
Product Description
Catalog Number:
AG002IH3
Chemical Name:
2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-
CAS Number:
20636-41-3
Molecular Formula:
C4H4N2O3
Molecular Weight:
128.0862
MDL Number:
MFCD00082987
IUPAC Name:
5-hydroxy-1H-pyrimidine-2,4-dione
InChI:
InChI=1S/C4H4N2O3/c7-2-1-5-4(9)6-3(2)8/h1,7H,(H2,5,6,8,9)
InChI Key:
OFJNVANOCZHTMW-UHFFFAOYSA-N
SMILES:
Oc1c[nH]c(=O)[nH]c1=O
EC Number:
243-932-5
NSC Number:
90431
Properties
Complexity:
196  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
128.022g/mol
Formal Charge:
0
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
128.087g/mol
Monoisotopic Mass:
128.022g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
78.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.1  
Literature
Title Journal
Enhancement of NEIL1 protein-initiated oxidized DNA base excision repair by heterogeneous nuclear ribonucleoprotein U (hnRNP-U) via direct interaction. The Journal of biological chemistry 20121005
Profiling cytosine oxidation in DNA by LC-MS/MS. Chemical research in toxicology 20120917
Biochemical mapping of human NEIL1 DNA glycosylase and AP lyase activities. DNA repair 20120901
A DNA oligomer containing 2,2,4-triamino-5(2H)-oxazolone is incised by human NEIL1 and NTH1. Mutation research 20120601
Structural characterization of viral ortholog of human DNA glycosylase NEIL1 bound to thymine glycol or 5-hydroxyuracil-containing DNA. The Journal of biological chemistry 20120203
DNA glycosylases: in DNA repair and beyond. Chromosoma 20120201
Association of polymorphisms in oxidative stress genes with clinical outcomes for bladder cancer treated with Bacillus Calmette-Guérin. PloS one 20120101
A nano-chip-LC/MSn based strategy for characterization of modified nucleosides using reduced porous graphitic carbon as a stationary phase. Journal of the American Society for Mass Spectrometry 20110701
Delayed repair of radiation induced clustered DNA damage: friend or foe? Mutation research 20110603
Unexpected role for Helicobacter pylori DNA polymerase I as a source of genetic variability. PLoS genetics 20110601
Preferential repair of oxidized base damage in the transcribed genes of mammalian cells. The Journal of biological chemistry 20110225
New insights in the removal of the hydantoins, oxidation product of pyrimidines, via the base excision and nucleotide incision repair pathways. PloS one 20110101
Direct detection and sequencing of damaged DNA bases. Genome integrity 20110101
Base-promoted reaction of 5-hydroxyuracil derivatives with peroxyl radicals. Organic letters 20100917
Specific Inhibition of NEIL-initiated repair of oxidized base damage in human genome by copper and iron: potential etiological linkage to neurodegenerative diseases. The Journal of biological chemistry 20100910
Cockayne syndrome group B protein promotes mitochondrial DNA stability by supporting the DNA repair association with the mitochondrial membrane. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20100701
RPA physically interacts with the human DNA glycosylase NEIL1 to regulate excision of oxidative DNA base damage in primer-template structures. DNA repair 20100604
Substrate specific stimulation of NEIL1 by WRN but not the other human RecQ helicases. DNA repair 20100604
The oxidative DNA glycosylases of Mycobacterium tuberculosis exhibit different substrate preferences from their Escherichia coli counterparts. DNA repair 20100204
Stimulation of DNA Glycosylase Activities by XPC Protein Complex: Roles of Protein-Protein Interactions. Journal of nucleic acids 20100101
Early Steps in the DNA Base Excision Repair Pathway of a Fission Yeast Schizosaccharomyces pombe. Journal of nucleic acids 20100101
Molecular mechanisms of ultraviolet radiation-induced DNA damage and repair. Journal of nucleic acids 20100101
Sources of extracellular, oxidatively-modified DNA lesions: implications for their measurement in urine. Journal of clinical biochemistry and nutrition 20091101
Modulation of DNA glycosylase activities in mesenchymal stem cells. Experimental cell research 20090910
Catalytically impaired hMYH and NEIL1 mutant proteins identified in patients with primary sclerosing cholangitis and cholangiocarcinoma. Carcinogenesis 20090701
Characterization of the major formamidopyrimidine-DNA glycosylase homolog in Mycobacterium tuberculosis and its linkage to variable tandem repeats. FEMS immunology and medical microbiology 20090701
The Base Excision Repair system of Salmonella enterica serovar typhimurium counteracts DNA damage by host nitric oxide. PLoS pathogens 20090501
Base excision repair of oxidative DNA damage and association with cancer and aging. Carcinogenesis 20090101
Raltegravir, elvitegravir, and metoogravir: the birth of 'me-too' HIV-1 integrase inhibitors. Retrovirology 20090101
Insights into the role of Val45 and Gln182 of Escherichia coli MutY in DNA substrate binding and specificity. BMC biochemistry 20090101
Physical and functional interaction between human oxidized base-specific DNA glycosylase NEIL1 and flap endonuclease 1. The Journal of biological chemistry 20081003
Base excision repair activities in organotypic hippocampal slice cultures exposed to oxygen and glucose deprivation. DNA repair 20080601
Examination of hypochlorous acid-induced damage to cytosine residues in a CpG dinucleotide in DNA. Chemical research in toxicology 20080601
Base-pairing properties of the oxidized cytosine derivative, 5-hydroxy uracil. Biochemical and biophysical research communications 20080215
Interaction of the human DNA glycosylase NEIL1 with proliferating cell nuclear antigen. The potential for replication-associated repair of oxidized bases in mammalian genomes. The Journal of biological chemistry 20080208
Ab initio base-pairing energies of an oxidized thymine product, 5-formyluracil, with standard DNA bases at the BSSE-free DFT and MP2 theory levels. Organic & biomolecular chemistry 20070521
Different organization of base excision repair of uracil in DNA in nuclei and mitochondria and selective upregulation of mitochondrial uracil-DNA glycosylase after oxidative stress. Neuroscience 20070414
NEIL1 is the major DNA glycosylase that processes 5-hydroxyuracil in the proximity of a DNA single-strand break. Biochemistry 20070403
Uracil in DNA--general mutagen, but normal intermediate in acquired immunity. DNA repair 20070401
Radiosensitization by nitric oxide at low radiation doses. Radiation research 20070401
DNA polymerase delta-dependent repair of DNA single strand breaks containing 3'-end proximal lesions. Nucleic acids research 20070201
Base excision repair and the role of MUTYH. Hereditary cancer in clinical practice 20070101
NEIL2-initiated, APE-independent repair of oxidized bases in DNA: Evidence for a repair complex in human cells. DNA repair 20061209
RNA polymerase II bypass of oxidative DNA damage is regulated by transcription elongation factors. The EMBO journal 20061129
Ab initio base-pairing energies of uracil and 5-hydroxyuracil with standard DNA bases at the BSSE-free DFT and MP2 theory levels. Organic & biomolecular chemistry 20060507
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Physical and functional interactions between Escherichia coli MutY and endonuclease VIII. The Biochemical journal 20060101
Differential modulation of base excision repair activities during brain ontogeny: implications for repair of transcribed DNA. Mechanisms of ageing and development 20060101
DNA oxidation in Alzheimer's disease. Antioxidants & redox signaling 20060101
Reaction of substituted pyrimidines with photochemically generated t-BuO* radicals. Indian journal of biochemistry & biophysics 20051201
5-hydroxyuracil can form stable base pairs with all four bases in a DNA duplex. Chemical communications (Cambridge, England) 20050121
Identification of a zinc finger domain in the human NEIL2 (Nei-like-2) protein. The Journal of biological chemistry 20041105
Oxidation of 5-hydroxy-2'-deoxyuridine into isodialuric acid, dialuric acid, and hydantoin products. Journal of the American Chemical Society 20040602
Repair of oxidized bases in DNA bubble structures by human DNA glycosylases NEIL1 and NEIL2. The Journal of biological chemistry 20031212
Detection of p53 mutations in precancerous gastric tissue. British journal of cancer 20031006
Compromised incision of oxidized pyrimidines in liver mitochondria of mice deficient in NTH1 and OGG1 glycosylases. The Journal of biological chemistry 20030905
Mammalian 5-formyluracil-DNA glycosylase. 1. Identification and characterization of a novel activity that releases 5-formyluracil from DNA. Biochemistry 20030506
Oxidative DNA base modifications and polycyclic aromatic hydrocarbon DNA adducts in squamous cell carcinoma of larynx. Free radical research 20030301
Identification and characterization of mammalian 5-formyluracil-DNA glycosylase. Nucleic acids research. Supplement (2001) 20030101
A back-up glycosylase in Nth1 knock-out mice is a functional Nei (endonuclease VIII) homologue. The Journal of biological chemistry 20021101
Repair of deaminated bases in DNA. Free radical biology & medicine 20021001
Identification and characterization of a novel human DNA glycosylase for repair of cytosine-derived lesions. The Journal of biological chemistry 20020823
Biological consequences of free radical-damaged DNA bases. Free radical biology & medicine 20020701
Determination of active site residues in Escherichia coli endonuclease VIII. The Journal of biological chemistry 20020125
Alternative nucleotide incision repair pathway for oxidative DNA damage. Nature 20020110
Stimulation of human endonuclease III by Y box-binding protein 1 (DNA-binding protein B). Interaction between a base excision repair enzyme and a transcription factor. The Journal of biological chemistry 20010615
Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii. Biochemical pharmacology 19940817
New substrates for old enzymes. 5-Hydroxy-2'-deoxycytidine and 5-hydroxy-2'-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA N-glycosylase, while 5-hydroxy-2'-deoxyuridine is a substrate for uracil DNA N-glycosylase. The Journal of biological chemistry 19940722
Properties