|
|
| 5,6-dihydrouracil |
|
| CHEBI:15901 |
|
| A pyrimidine obtained by formal addition of hydrogen across the 5,6-position of uracil. |
|
This entity has been manually annotated by the ChEBI Team.
|
|
|
CHEBI:1999, CHEBI:42107, CHEBI:921, CHEBI:19360, CHEBI:20511, CHEBI:12078, CHEBI:28622
|
|
| ChemicalBook:CB2117111, eMolecules:24627778, eMolecules:537627, ZINC000000895228 |
|
|
Molfile
XML
SDF
|
|
|
more structures >>
|
|
call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js
|
| Dihydrouracil is an intermediate in the catabolism of uracil. It is the base present in the nucleoside dihydrouridine. |
|
Read full article at Wikipedia
|
| InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8) |
| OIVLITBTBDPEFK-UHFFFAOYSA-N |
|
|
Mus musculus
(NCBI:txid10090)
|
Source: BioModels - MODEL1507180067
See:
PubMed
|
|
Escherichia coli
(NCBI:txid562)
|
See:
PubMed
|
|
Homo sapiens
(NCBI:txid9606)
|
See:
DOI
|
|
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
|
|
View more via ChEBI Ontology
|
dihydropyrimidine-2,4(1H,3H)-dione
|
|
2,4(1H,3H)-Pyrimidinedione, dihydro-
|
KEGG COMPOUND
|
|
2,4-Dioxotetrahydropyrimidine
|
KEGG COMPOUND
|
|
2,4-Dioxotetrahydropyrimidine
|
KEGG COMPOUND
|
|
5,6-Dihydro-2,4-dihydroxypyrimidine
|
KEGG COMPOUND
|
|
5,6-Dihydrouracil
|
KEGG COMPOUND
|
|
5,6-dihydrouracil
|
UniProt
|
|
Dihydro-2,4(1H,3H)-pyrimidinedione
|
KEGG COMPOUND
|
|
DIHYDROPYRIMIDINE-2,4(1H,3H)-DIONE
|
PDBeChem
|
|
Dihydrouracil
|
KEGG COMPOUND
|
|
Dihydrouracile
|
KEGG COMPOUND
|
|
Hydrouracil
|
KEGG COMPOUND
|
|
112496
|
Reaxys Registry Number
|
Reaxys
|
|
1851498
|
Beilstein Registry Number
|
Beilstein
|
|
504-07-4
|
CAS Registry Number
|
ChemIDplus
|
|
504-07-4
|
CAS Registry Number
|
NIST Chemistry WebBook
|
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]
Metabolic profiles of biofluids obtained by atmospheric pressure ionization mass spectrometry-based technologies contain hundreds to thousands of features, most of them remaining unknown or at least not characterized in analytical systems. We report here on the annotation of the human adult urinary metabolome and metabolite identification from electrospray ionization mass spectrometry (ESI-MS)-based metabolomics data sets. Features of biological interest were first of all annotated using the ESI-MS database of the laboratory. They were also grouped, thanks to software tools, and annotated using public databases. Metabolite identification was achieved using two complementary approaches: (i) formal identification by matching chromatographic retention times, mass spectra, and also product ion spectra (if required) of metabolites to be characterized in biological data sets to those of reference compounds and (ii) putative identification from biological data thanks to MS/MS experiments for metabolites not available in our chemical library. By these means, 384 metabolites corresponding to 1484 annotated features (659 in negative ion mode and 825 in positive ion mode) were characterized in human urine samples. Of these metabolites, 192 and 66 were formally and putatively identified, respectively, and 54 are reported in human urine for the first time. These lists of features could be used by other laboratories to annotate their ESI-MS metabolomics data sets. | Kristensen MH, Pedersen P, Mejer J (2010)
The value of dihydrouracil/uracil plasma ratios in predicting 5-fluorouracil-related toxicity in colorectal cancer patients.
The Journal of international medical research 38, 1313-1323 [PubMed:20926004]
[show Abstract]
This study investigated the relationship between the dihydrouracil/uracil (UH(2)/U) plasma ratio, a surrogate marker of dihydropyrimidine dehydrogenase (DPD) activity, and 5-fluorouracil (5-FU)-related early toxicity. Plasma UH(2)/U ratios were determined in 68 colorectal cancer patients and 100 healthy controls. A cut-off value indicative of DPD deficiency was calculated using receiver operator characteristics. Patients experiencing toxicity were screened for the DPD G-to-A point mutation within the 5'-splicing donor site of intron 14 (IVS14+1G>A). Overall, 24/68 patients (35%) experienced toxicity (all grades) and abnormal UH(2)/U ratios were demonstrated in 21/24 (87.5%) patients. Drug concentrations up to 130 times the recommended level were found in 13/24 (54%) patients experiencing toxicity. One patient experiencing toxicity was a heterozygous carrier of the IVS14+1G>A mutation. A low UH(2)/U plasma ratio had a sensitivity of 0.87 and specificity of 0.93 for predicting 5-FU-induced toxicity. Systematic detection of DPD-deficient patients using the UH(2)/U ratio could optimize 5-FU-based chemotherapy and minimize life-threatening toxicity. | Ben Fredj R, Gross E, Ben Ahmed S, Hassine H, Saguem S (2009)
The dihydrouracil/uracil ratio in plasma, clinical and genetic analysis for screening of dihydropyrimidine dehydrogenase deficiency in colorectal cancer patients treated with 5-fluorouracil.
Pathologie-biologie 57, 470-476 [PubMed:18619742]
[show Abstract]
A rapid and cost-effective reversed phase high performance liquid chromatography (HPLC) method for quantification of dihydrouracil to uracil ratio (UH2/U) in plasma has been developed and used to screen for dihydropyrimidine dehydrogenase (DPD) deficiency in nine patients treated with 5-fluorouracil (5-FU). This HPLC method is based on the use of a simultaneous UV detection at 205 and 268nm during the analysis run of the plasma extract and taking into account the particularity that UH2 shows no absorbance response at 268nm. The plasma UH2/U ratio values evaluated by the use of our HPLC assay were found to be highly correlated with the plasma 5-FU-half-life values and were significantly associated with the toxic side effects, whereas, data set provided from genetic analysis of the coding sequences of the DPD gene (DPYD) were found to be insufficient to explain all the cases of the 5-FU-related toxicity pattern. The proposed HPLC assay could be available for routine clinical use for DPD deficiency assessment in patients prior to 5-FU administration. | Aoun R, Renaud JL, Dixneuf PH, Bruneau C (2005)
Concomitant monoreduction and hydrogenation of unsaturated cyclic imides to lactams catalyzed by ruthenium compounds.
Angewandte Chemie (International ed. in English) 44, 2021-2023 [PubMed:15724255] |
|
