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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| Definitive identification of mammalian 5-hydroxymethyluracil DNA N-glycosylase activity as SMUG1. | 2001 Nov 9 |
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| Characterization of the substrate specificity of a human 5-hydroxymethyluracil glycosylase activity. | 2002 Jan |
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| The role of surface-exposed lysines in wrapping DNA about the bacterial histone-like protein HU. | 2002 Jun 18 |
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| Endogenous DNA lesions can inhibit the binding of the AP-1 (c-Jun) transcription factor. | 2002 Jun 25 |
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| Repair of deaminated bases in DNA. | 2002 Oct 1 |
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| 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 Oct 18 |
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| Identification and characterization of mammalian 5-formyluracil-DNA glycosylase. | 2003 |
|
| Mammalian 5-formyluracil-DNA glycosylase. 1. Identification and characterization of a novel activity that releases 5-formyluracil from DNA. | 2003 May 6 |
|
| Cellular and molecular mechanisms in environmental and occupational inhalation toxicology. | 2004 |
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| Radiation-induced DNA damage: formation, measurement, and biochemical features. | 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 |
|
| Base J, found in nuclear DNA of Trypanosoma brucei, is not a target for DNA glycosylases. | 2004 Feb 3 |
|
| [Hydroxymethyluracil in the correction of adverse effects caused by chemotherapy of malignant neoplasms]. | 2004 Jan-Feb |
|
| 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 |
|
| Generation of thymine radicals from 6-alkoxy-5-bromo-5,6-dihydrothymine derivatives by radiolytic reduction and photolytic dehalogenation. | 2008 Apr |
|
| 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 |
|
| Tissue distribution of 5-hydroxymethylcytosine and search for active demethylation intermediates. | 2010 Dec 23 |
|
| 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 |
|
| Biosynthesis and molecular genetics of polyketides in marine dinoflagellates. | 2010 Mar 31 |
|
| 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
