Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H6N2O3 |
| Molecular Weight | 142.1127 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OCC1=CNC(=O)NC1=O
InChI
InChIKey=JDBGXEHEIRGOBU-UHFFFAOYSA-N
InChI=1S/C5H6N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1,8H,2H2,(H2,6,7,9,10)
5-(Hydroxymethyl)uracil may be formed during the course of the two processes: oxidation/hydroxylation of thymine with resultant formation of 5-hydroxymethyluracil paired with adenine (produced by reactive oxygen species) and reacting of reactive oxygen species with 5-methylcytosine forming 5-hydroxymethylcytosine, followed by its deamination to 5-hydroxymethyluracil mispaired with guanine. Determination and quantification of hydroxymethyl uracil in urine serve as a potential biomarker of oxidative DNA damage. It was discovered, that urinary 5-hydroxymethyluracil might reflect the oxidative stress/chronic inflammation in colorectal cancer although the diagnostic performance for early-detection is moderate.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 5-Hydroxymethyluracil excretion, plasma TBARS and plasma antioxidant vitamins in adriamycin-treated patients. | 1996 |
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| Estimation of oxidative DNA damage in man from urinary excretion of repair products. | 1998 |
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| Rapid screening of high-risk patients for disorders of purine and pyrimidine metabolism using HPLC-electrospray tandem mass spectrometry of liquid urine or urine-soaked filter paper strips. | 2000 Apr |
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| Binding activity of replication protein A to single-stranded DNA containing oxidized pyrimidine base. | 2001 |
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| Long term adaptation of a microbial population to a permanent metabolic constraint: overcoming thymineless death by experimental evolution of Escherichia coli. | 2001 |
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| High-affinity DNA binding of HU protein from the hyperthermophile Thermotoga maritima. | 2001 Aug 17 |
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| Excessive base excision repair of 5-hydroxymethyluracil from DNA induces apoptosis in Chinese hamster V79 cells containing mutant p53. | 2001 Jan |
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| Kinetic analysis of nucleotides incorporated opposite oxidized thymine bases on template DNA. | 2002 |
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| Characterization of the substrate specificity of a human 5-hydroxymethyluracil glycosylase activity. | 2002 Jan |
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| Rapid gas chromatographic-mass spectrometric diagnosis of dihydropyrimidine dehydrogenase deficiency and dihydropyrimidinase deficiency. | 2003 Jul 15 |
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| Structure and specificity of the vertebrate anti-mutator uracil-DNA glycosylase SMUG1. | 2003 Jun |
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| Mammalian 5-formyluracil-DNA glycosylase. 1. Identification and characterization of a novel activity that releases 5-formyluracil from DNA. | 2003 May 6 |
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| Cellular and molecular mechanisms in environmental and occupational inhalation toxicology. | 2004 |
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| Qualitative and quantitative analyses of the decomposition products that arise from the exposure of thymine to monochromatic ultrasoft X rays and 60Co gamma rays in the solid state. | 2004 Apr |
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| [Hydroxymethyluracil in the correction of adverse effects caused by chemotherapy of malignant neoplasms]. | 2004 Jan-Feb |
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| Diet is not responsible for the presence of several oxidatively damaged DNA lesions in mouse urine. | 2004 Nov |
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| Urinary excretion of DNA repair products correlates with metabolic rates as well as with maximum life spans of different mammalian species. | 2004 Nov 1 |
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| Repair of oxidative damage of thymine by HeLa whole-cell extracts: simultaneous analysis using a microsupport and comparison with traditional PAGE analysis. | 2005 Feb |
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| DNA glycosylase activities for thymine residues oxidized in the methyl group are functions of the hNEIL1 and hNTH1 enzymes in human cells. | 2005 Jan 2 |
|
| Organization of the genome and gene expression in a nuclear environment lacking histones and nucleosomes: the amazing dinoflagellates. | 2005 Mar |
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| Measurement of urinary excretion of 5-hydroxymethyluracil in human by GC/NICI/MS: correlation with cigarette smoking, urinary TBARS and etheno DNA adduct. | 2005 Mar 15 |
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| DNA polymerase lambda protects mouse fibroblasts against oxidative DNA damage and is recruited to sites of DNA damage/repair. | 2005 Sep 9 |
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| A new protein superfamily includes two novel 3-methyladenine DNA glycosylases from Bacillus cereus, AlkC and AlkD. | 2006 Mar |
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| Formamide as the main building block in the origin of nucleic acids. | 2007 Aug 16 |
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| Measurement of the incorporation and repair of exogenous 5-hydroxymethyl-2'-deoxyuridine in human cells in culture using gas chromatography-negative chemical ionization-mass spectrometry. | 2007 Dec |
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| DNA-uracil and human pathology. | 2007 Jun-Aug |
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| Correction of morphological shifts in experimental syringomyelia. | 2007 May |
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| Experimental study of hepatoprotective activity of hydroxymethyluracil. | 2007 May |
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| 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. | 2007 May 21 |
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| Recombinant Schizosaccharomyces pombe Nth1 protein exhibits DNA glycosylase activities for 8-oxo-7,8-dihydroguanine and thymine residues oxidized in the methyl group. | 2007 Sep |
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| Generation of thymine radicals from 6-alkoxy-5-bromo-5,6-dihydrothymine derivatives by radiolytic reduction and photolytic dehalogenation. | 2008 Apr |
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| Hepatic oxidative DNA damage is associated with increased risk for hepatocellular carcinoma in chronic hepatitis C. | 2008 Feb 12 |
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| Thymine hydroperoxide as a potential source of singlet molecular oxygen in DNA. | 2009 Aug 15 |
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| Sources of extracellular, oxidatively-modified DNA lesions: implications for their measurement in urine. | 2009 Nov |
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| Classification of Myoviridae bacteriophages using protein sequence similarity. | 2009 Oct 26 |
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| CyDNA: synthesis and replication of highly Cy-dye substituted DNA by an evolved polymerase. | 2010 Apr 14 |
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| Opposite effects of 5-hydroxymethyluracil on mitogenic response of T cells stimulated through T-cell receptor or through T-cell receptor and CD28 co-receptor molecule. | 2010 Dec |
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| Tissue distribution of 5-hydroxymethylcytosine and search for active demethylation intermediates. | 2010 Dec 23 |
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| Domain swapping in allosteric modulation of DNA specificity. | 2010 Dec 7 |
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| Stimulation of DNA Glycosylase Activities by XPC Protein Complex: Roles of Protein-Protein Interactions. | 2010 Jul 25 |
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| Biosynthesis and molecular genetics of polyketides in marine dinoflagellates. | 2010 Mar 31 |
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| Early Steps in the DNA Base Excision Repair Pathway of a Fission Yeast Schizosaccharomyces pombe. | 2010 Sep 16 |
|
| Error-Prone Translesion DNA Synthesis by Escherichia coli DNA Polymerase IV (DinB) on Templates Containing 1,2-dihydro-2-oxoadenine. | 2010 Sep 26 |
Patents
Sample Use Guides
The effect of 5-hydroxymethyluracil (0.01-10 μg/ml) on the mitogenic response of donor peripheral blood T cells under conditions of lymphocyte stimulation through T-cell receptor (antiCD3 monoclonal antibodies) or through T-cell receptor and CD28 co-receptor molecule (antiCD3 and antiCD28 monoclonal antibodies) was studied. It was shown, that 5-hydroxymethyluracil suppressed the mitogenic response of T cells stimulated with antiCD3 antibodies, which was paralleled by an increase in the count of silent cells and decrease in the count of dividing lymphocytes, but not by stimulation of apoptosis of activated cells.
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DTXSID9063455
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224-636-5
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16964
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590TQ3GL34
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78168
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20901
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4433-40-3
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SUBSTANCE RECORD
