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)
| Molecular Formula | C5H6N2O3 |
| Molecular Weight | 142.1127 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Tissue distribution of 5-hydroxymethylcytosine and search for active demethylation intermediates. | 2010-12-23 |
|
| Domain swapping in allosteric modulation of DNA specificity. | 2010-12-07 |
|
| 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. | 2010-12 |
|
| Error-Prone Translesion DNA Synthesis by Escherichia coli DNA Polymerase IV (DinB) on Templates Containing 1,2-dihydro-2-oxoadenine. | 2010-09-26 |
|
| Early Steps in the DNA Base Excision Repair Pathway of a Fission Yeast Schizosaccharomyces pombe. | 2010-09-16 |
|
| Stimulation of DNA Glycosylase Activities by XPC Protein Complex: Roles of Protein-Protein Interactions. | 2010-07-25 |
|
| CyDNA: synthesis and replication of highly Cy-dye substituted DNA by an evolved polymerase. | 2010-04-14 |
|
| Biosynthesis and molecular genetics of polyketides in marine dinoflagellates. | 2010-03-31 |
|
| Sources of extracellular, oxidatively-modified DNA lesions: implications for their measurement in urine. | 2009-11 |
|
| Classification of Myoviridae bacteriophages using protein sequence similarity. | 2009-10-26 |
|
| Thymine hydroperoxide as a potential source of singlet molecular oxygen in DNA. | 2009-08-15 |
|
| Generation of thymine radicals from 6-alkoxy-5-bromo-5,6-dihydrothymine derivatives by radiolytic reduction and photolytic dehalogenation. | 2008-04 |
|
| Hepatic oxidative DNA damage is associated with increased risk for hepatocellular carcinoma in chronic hepatitis C. | 2008-02-12 |
|
| 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. | 2007-12 |
|
| Recombinant Schizosaccharomyces pombe Nth1 protein exhibits DNA glycosylase activities for 8-oxo-7,8-dihydroguanine and thymine residues oxidized in the methyl group. | 2007-09 |
|
| Formamide as the main building block in the origin of nucleic acids. | 2007-08-16 |
|
| 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. | 2007-05-21 |
|
| Correction of morphological shifts in experimental syringomyelia. | 2007-05 |
|
| Experimental study of hepatoprotective activity of hydroxymethyluracil. | 2007-05 |
|
| DNA-uracil and human pathology. | 2007-03-20 |
|
| A new protein superfamily includes two novel 3-methyladenine DNA glycosylases from Bacillus cereus, AlkC and AlkD. | 2006-03 |
|
| DNA polymerase lambda protects mouse fibroblasts against oxidative DNA damage and is recruited to sites of DNA damage/repair. | 2005-09-09 |
|
| Measurement of urinary excretion of 5-hydroxymethyluracil in human by GC/NICI/MS: correlation with cigarette smoking, urinary TBARS and etheno DNA adduct. | 2005-03-15 |
|
| Organization of the genome and gene expression in a nuclear environment lacking histones and nucleosomes: the amazing dinoflagellates. | 2005-03 |
|
| Repair of oxidative damage of thymine by HeLa whole-cell extracts: simultaneous analysis using a microsupport and comparison with traditional PAGE analysis. | 2005-02 |
|
| DNA glycosylase activities for thymine residues oxidized in the methyl group are functions of the hNEIL1 and hNTH1 enzymes in human cells. | 2005-01-02 |
|
| Urinary excretion of DNA repair products correlates with metabolic rates as well as with maximum life spans of different mammalian species. | 2004-11-01 |
|
| Diet is not responsible for the presence of several oxidatively damaged DNA lesions in mouse urine. | 2004-11 |
|
| [Hydroxymethyluracil in the correction of adverse effects caused by chemotherapy of malignant neoplasms]. | 2004-04-15 |
|
| 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. | 2004-04 |
|
| Base J, found in nuclear DNA of Trypanosoma brucei, is not a target for DNA glycosylases. | 2004-02-03 |
|
| Cellular and molecular mechanisms in environmental and occupational inhalation toxicology. | 2004 |
|
| Radiation-induced DNA damage: formation, measurement, and biochemical features. | 2004 |
|
| The transcription factor, NFI/CTF plays a positive regulatory role in expression of the hSMUG1 gene. | 2003-12-09 |
|
| Surface salt bridges modulate DNA wrapping by the type II DNA-binding protein TF1. | 2003-07-29 |
|
| Rapid gas chromatographic-mass spectrometric diagnosis of dihydropyrimidine dehydrogenase deficiency and dihydropyrimidinase deficiency. | 2003-07-15 |
|
| Mismatch uracil glycosylase from Escherichia coli: a general mismatch or a specific DNA glycosylase? | 2003-06-06 |
|
| Structure and specificity of the vertebrate anti-mutator uracil-DNA glycosylase SMUG1. | 2003-06 |
|
| Mammalian 5-formyluracil-DNA glycosylase. 2. Role of SMUG1 uracil-DNA glycosylase in repair of 5-formyluracil and other oxidized and deaminated base lesions. | 2003-05-06 |
|
| Mammalian 5-formyluracil-DNA glycosylase. 1. Identification and characterization of a novel activity that releases 5-formyluracil from DNA. | 2003-05-06 |
|
| Identification and characterization of mammalian 5-formyluracil-DNA glycosylase. | 2003 |
|
| hUNG2 is the major repair enzyme for removal of uracil from U:A matches, U:G mismatches, and U in single-stranded DNA, with hSMUG1 as a broad specificity backup. | 2002-10-18 |
|
| Repair of deaminated bases in DNA. | 2002-10-01 |
|
| Endogenous DNA lesions can inhibit the binding of the AP-1 (c-Jun) transcription factor. | 2002-06-25 |
|
| The role of surface-exposed lysines in wrapping DNA about the bacterial histone-like protein HU. | 2002-06-18 |
|
| Characterization of the substrate specificity of a human 5-hydroxymethyluracil glycosylase activity. | 2002-01 |
|
| Kinetic analysis of nucleotides incorporated opposite oxidized thymine bases on template DNA. | 2002 |
|
| Binding activity of replication protein A to single-stranded DNA containing oxidized pyrimidine base. | 2001 |
|
| Estimation of oxidative DNA damage in man from urinary excretion of repair products. | 1998 |
|
| 5-Hydroxymethyluracil excretion, plasma TBARS and plasma antioxidant vitamins in adriamycin-treated patients. | 1996 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:28:34 GMT 2025
by
admin
on
Mon Mar 31 19:28:34 GMT 2025
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| Record UNII |
590TQ3GL34
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| Record Status |
Validated (UNII)
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| Record Version |
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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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