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 |
|---|---|---|
| Binding activity of replication protein A to single-stranded DNA containing oxidized pyrimidine base. | 2001 |
|
| High-affinity DNA binding of HU protein from the hyperthermophile Thermotoga maritima. | 2001 Aug 17 |
|
| 5-Formyluracil and its nucleoside derivatives confer toxicity and mutagenicity to mammalian cells by interfering with normal RNA and DNA metabolism. | 2001 Feb 3 |
|
| Excessive base excision repair of 5-hydroxymethyluracil from DNA induces apoptosis in Chinese hamster V79 cells containing mutant p53. | 2001 Jan |
|
| Definitive identification of mammalian 5-hydroxymethyluracil DNA N-glycosylase activity as SMUG1. | 2001 Nov 9 |
|
| Kinetic analysis of nucleotides incorporated opposite oxidized thymine bases on template DNA. | 2002 |
|
| Characterization of the substrate specificity of a human 5-hydroxymethyluracil glycosylase activity. | 2002 Jan |
|
| The role of surface-exposed lysines in wrapping DNA about the bacterial histone-like protein HU. | 2002 Jun 18 |
|
| Endogenous DNA lesions can inhibit the binding of the AP-1 (c-Jun) transcription factor. | 2002 Jun 25 |
|
| 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 |
|
| Identification and characterization of mammalian 5-formyluracil-DNA glycosylase. | 2003 |
|
| The transcription factor, NFI/CTF plays a positive regulatory role in expression of the hSMUG1 gene. | 2003 Dec 9 |
|
| Rapid gas chromatographic-mass spectrometric diagnosis of dihydropyrimidine dehydrogenase deficiency and dihydropyrimidinase deficiency. | 2003 Jul 15 |
|
| Surface salt bridges modulate DNA wrapping by the type II DNA-binding protein TF1. | 2003 Jul 29 |
|
| Structure and specificity of the vertebrate anti-mutator uracil-DNA glycosylase SMUG1. | 2003 Jun |
|
| 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 May 6 |
|
| Cellular and molecular mechanisms in environmental and occupational inhalation toxicology. | 2004 |
|
| Radiation-induced DNA damage: formation, measurement, and biochemical features. | 2004 |
|
| Base J, found in nuclear DNA of Trypanosoma brucei, is not a target for DNA glycosylases. | 2004 Feb 3 |
|
| Diet is not responsible for the presence of several oxidatively damaged DNA lesions in mouse urine. | 2004 Nov |
|
| Urinary excretion of DNA repair products correlates with metabolic rates as well as with maximum life spans of different mammalian species. | 2004 Nov 1 |
|
| Repair of oxidative damage of thymine by HeLa whole-cell extracts: simultaneous analysis using a microsupport and comparison with traditional PAGE analysis. | 2005 Feb |
|
| 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 |
|
| 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 |
|
| Experimental study of hepatoprotective activity of hydroxymethyluracil. | 2007 May |
|
| 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 |
|
| Sources of extracellular, oxidatively-modified DNA lesions: implications for their measurement in urine. | 2009 Nov |
|
| CyDNA: synthesis and replication of highly Cy-dye substituted DNA by an evolved polymerase. | 2010 Apr 14 |
|
| 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 |
|
| Stimulation of DNA Glycosylase Activities by XPC Protein Complex: Roles of Protein-Protein Interactions. | 2010 Jul 25 |
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
Fri Dec 15 18:58:49 GMT 2023
by
admin
on
Fri Dec 15 18:58:49 GMT 2023
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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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224-636-5
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16964
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