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 |
|---|---|---|
| 5-Hydroxymethyluracil excretion, plasma TBARS and plasma antioxidant vitamins in adriamycin-treated patients. | 1996 |
|
| Estimation of oxidative DNA damage in man from urinary excretion of repair products. | 1998 |
|
| Long term adaptation of a microbial population to a permanent metabolic constraint: overcoming thymineless death by experimental evolution of Escherichia coli. | 2001 |
|
| High-affinity DNA binding of HU protein from the hyperthermophile Thermotoga maritima. | 2001 Aug 17 |
|
| Role of the Escherichia coli and human DNA glycosylases that remove 5-formyluracil from DNA in the prevention of mutations. | 2001 Mar |
|
| Definitive identification of mammalian 5-hydroxymethyluracil DNA N-glycosylase activity as SMUG1. | 2001 Nov 9 |
|
| 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 |
|
| Repair of deaminated bases in DNA. | 2002 Oct 1 |
|
| 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 |
|
| 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 |
|
| Structure and specificity of the vertebrate anti-mutator uracil-DNA glycosylase SMUG1. | 2003 Jun |
|
| Mismatch uracil glycosylase from Escherichia coli: a general mismatch or a specific DNA glycosylase? | 2003 Jun 6 |
|
| 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 |
|
| 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 |
|
| [Hydroxymethyluracil in the correction of adverse effects caused by chemotherapy of malignant neoplasms]. | 2004 Jan-Feb |
|
| Urinary excretion of DNA repair products correlates with metabolic rates as well as with maximum life spans of different mammalian species. | 2004 Nov 1 |
|
| 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 |
|
| DNA polymerase lambda protects mouse fibroblasts against oxidative DNA damage and is recruited to sites of DNA damage/repair. | 2005 Sep 9 |
|
| A new protein superfamily includes two novel 3-methyladenine DNA glycosylases from Bacillus cereus, AlkC and AlkD. | 2006 Mar |
|
| Formamide as the main building block in the origin of nucleic acids. | 2007 Aug 16 |
|
| 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 |
|
| DNA-uracil and human pathology. | 2007 Jun-Aug |
|
| Correction of morphological shifts in experimental syringomyelia. | 2007 May |
|
| Experimental study of hepatoprotective activity of hydroxymethyluracil. | 2007 May |
|
| 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 |
|
| 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 |
|
| Generation of thymine radicals from 6-alkoxy-5-bromo-5,6-dihydrothymine derivatives by radiolytic reduction and photolytic dehalogenation. | 2008 Apr |
|
| Hepatic oxidative DNA damage is associated with increased risk for hepatocellular carcinoma in chronic hepatitis C. | 2008 Feb 12 |
|
| Thymine hydroperoxide as a potential source of singlet molecular oxygen in DNA. | 2009 Aug 15 |
|
| 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 |
|
| Tissue distribution of 5-hydroxymethylcytosine and search for active demethylation intermediates. | 2010 Dec 23 |
|
| 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 |
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
|
| Record UNII |
590TQ3GL34
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID9063455
Created by
admin on Fri Dec 15 18:58:49 GMT 2023 , Edited by admin on Fri Dec 15 18:58:49 GMT 2023
|
PRIMARY | |||
|
224-636-5
Created by
admin on Fri Dec 15 18:58:49 GMT 2023 , Edited by admin on Fri Dec 15 18:58:49 GMT 2023
|
PRIMARY | |||
|
16964
Created by
admin on Fri Dec 15 18:58:49 GMT 2023 , Edited by admin on Fri Dec 15 18:58:49 GMT 2023
|
PRIMARY | |||
|
590TQ3GL34
Created by
admin on Fri Dec 15 18:58:49 GMT 2023 , Edited by admin on Fri Dec 15 18:58:49 GMT 2023
|
PRIMARY | |||
|
78168
Created by
admin on Fri Dec 15 18:58:49 GMT 2023 , Edited by admin on Fri Dec 15 18:58:49 GMT 2023
|
PRIMARY | |||
|
20901
Created by
admin on Fri Dec 15 18:58:49 GMT 2023 , Edited by admin on Fri Dec 15 18:58:49 GMT 2023
|
PRIMARY | |||
|
4433-40-3
Created by
admin on Fri Dec 15 18:58:49 GMT 2023 , Edited by admin on Fri Dec 15 18:58:49 GMT 2023
|
PRIMARY |