5-Hydroxyuracil (BioCAD00000229760)

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Metabolite Card

Formula: C4H4N2O3 (128.0222)
SMILES: OC1=CNC(=O)NC1=O

Synonyms [en]

5-hydroxyuracil; 5-hydroxy-uracil; Fluorouracil impurity B; 5-Hydroxyazouracil; Pyrimidine-2,4,5-triol; 5-hydroxy-1,2,3,4-tetrahydropyrimidine-2,4-dione

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

5-Hydroxyuracil. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000229760). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

5-hydroxyuracil, also known as dihydropyrimidine-2,4,5(3h)-trione or isobarbituric acid, is a member of the class of compounds known as hydroxypyrimidines. Hydroxypyrimidines are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. 5-hydroxyuracil is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5-hydroxyuracil can be found in broad bean, which makes 5-hydroxyuracil a potential biomarker for the consumption of this food product. 5-hydroxyuracil is an oxidized form of cytosine that is produced by the oxidative deamination of cytosines by reactive oxygen species. It does not distort the DNA molecule and is bypassed by replicative DNA polymerases. It can miscode for adenine and is potentially mutagenic .

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 20636-41-3
  • CAS Registry Number: 33332-28-4
  • CAS Registry Number: 496-76-4
  • PubChem: 73268
  • PubChem: 96994
  • ChEBI: ChEBI:29115
  • HMDB: HMDB0303045
  • BioCyc: CPD-18017
  • NCBI MeSH: 5-hydroxyuracil
  • Wikipedia: 5-Hydroxyuracil
  • MoNA: DNAAdduct006818
  • MoNA: DNAAdduct006819
  • MoNA: DNAAdduct006820
  • MoNA: DNAAdduct006821
  • MoNA: DNAAdduct006822
  • MoNA: DNAAdduct006823
  • MoNA: DNAAdduct006826
  • MoNA: DNAAdduct006827
  • Coconut NaturalProduct: CNP0090439.0
  • Coconut NaturalProduct: CNP0482214.0
  • Coconut NaturalProduct: CNP0573977.0

Class / Ontology

Metabolic Network
ID EC Number Name
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
Reactome:R-BTA-73884 Base Excision Repair
Reactome:R-BTA-73928 Depyrimidination
Reactome:R-CFA-73929 Base-Excision Repair, AP Site Formation
Reactome:R-CFA-110329 Cleavage of the damaged pyrimidine
Reactome:R-DDI-73894 DNA Repair
Reactome:R-GGA-73929 Base-Excision Repair, AP Site Formation
Reactome:R-GGA-110329 Cleavage of the damaged pyrimidine
Reactome:R-HSA-73929 Base-Excision Repair, AP Site Formation
Reactome:R-HSA-73928 Depyrimidination
Reactome:R-PFA-73929 Base-Excision Repair, AP Site Formation
Reactome:R-PFA-110329 Cleavage of the damaged pyrimidine
Reactome:R-RNO-73894 DNA Repair
Reactome:R-SCE-73929 Base-Excision Repair, AP Site Formation
Reactome:R-SCE-110329 Cleavage of the damaged pyrimidine
Reactome:R-SPO-73929 Base-Excision Repair, AP Site Formation
Reactome:R-SPO-110329 Cleavage of the damaged pyrimidine
Reactome:R-SSC-73884 Base Excision Repair
Reactome:R-SSC-73928 Depyrimidination
Reactome:R-XTR-73884 Base Excision Repair
Reactome:R-XTR-73928 Depyrimidination
View All Pathways