CHEBI:15901 - 5,6-dihydrouracil

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ChEBI Name 5,6-dihydrouracil
ChEBI ID CHEBI:15901
Definition A pyrimidine obtained by formal addition of hydrogen across the 5,6-position of uracil.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:1999, CHEBI:42107, CHEBI:921, CHEBI:19360, CHEBI:20511, CHEBI:12078, CHEBI:28622
Supplier Information ChemicalBook:CB2117111, eMolecules:24627778, eMolecules:537627, ZINC000000895228
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Dihydrouracil is an intermediate in the catabolism of uracil. It is the base present in the nucleoside dihydrouridine.
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Formula C4H6N2O2
Net Charge 0
Average Mass 114.10272
Monoisotopic Mass 114.04293
InChI InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)
InChIKey OIVLITBTBDPEFK-UHFFFAOYSA-N
SMILES O=C1CCNC(=O)N1
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): 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.
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ChEBI Ontology
Outgoing 5,6-dihydrouracil (CHEBI:15901) has functional parent uracil (CHEBI:17568)
5,6-dihydrouracil (CHEBI:15901) has role Escherichia coli metabolite (CHEBI:76971)
5,6-dihydrouracil (CHEBI:15901) has role human metabolite (CHEBI:77746)
5,6-dihydrouracil (CHEBI:15901) has role metabolite (CHEBI:25212)
5,6-dihydrouracil (CHEBI:15901) has role mouse metabolite (CHEBI:75771)
5,6-dihydrouracil (CHEBI:15901) is a pyrimidone (CHEBI:38337)
IUPAC Name
dihydropyrimidine-2,4(1H,3H)-dione
Synonyms Sources
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
Manual Xrefs Databases
C00429 KEGG COMPOUND
DI-H-URACIL MetaCyc
Dihydrouracil Wikipedia
DUC PDBeChem
HMDB0000076 HMDB
View more database links
Registry Numbers Types Sources
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
Citations
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]
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]
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]
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]
Last Modified
27 January 2016