5-Formyluracil

5-Formyluracil
Names
Preferred IUPAC name
2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde
Identifiers
CAS Number
  • 1195-08-0
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:80961
ChemSpider
  • 269368
ECHA InfoCard 100.153.693 Edit this at Wikidata
KEGG
  • C17206
PubChem CID
  • 304590
UNII
  • F2SUM4W8EB
CompTox Dashboard (EPA)
  • DTXSID40922994 Edit this at Wikidata
InChI
  • InChI=1S/C5H4N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1-2H,(H2,6,7,9,10)
    Key: OHAMXGZMZZWRCA-UHFFFAOYSA-N
  • O=CC1=CNC(=O)NC1=O
Properties
Chemical formula
 C5H4N2O3
Molar mass 140.098 g·mol−1
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Warning
Hazard statements
 H315, H319, H335
Precautionary statements
 P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

5-Formyluracil is a heterocyclic organic base. It is produced from the oxidation of the methyl group of thymine. It is found in bacteriophages, prokaryotes, as well as mammalian cells. Being mutagenic, it is of particular interest in the field of epigenetics.[1] It has been implicated in the formation of cancer causing cells.[2]

References

  1. ^ Klungland, A; Paulsen, R; Rolseth, V; Yamada, Y; Ueno, Y; Wiik, P; Matsuda, A; Seeberg, E; Bjelland, S (2001). "5-Formyluracil and its nucleoside derivatives confer toxicity and mutagenicity to mammalian cells by interfering with normal RNA and DNA metabolism". Toxicol Lett. 119 (1): 71–8. doi:10.1016/s0378-4274(00)00308-8. PMID 11275423.
  2. ^ Wang, Yafen; Zhang, Xiong; Zou, Guangrong; Peng, Shuang; Liu, Chaoxing; Zhou, Xiang (2019-04-16). "Detection and Application of 5-Formylcytosine and 5-Formyluracil in DNA". Accounts of Chemical Research. 52 (4): 1016–1024. doi:10.1021/acs.accounts.8b00543. ISSN 0001-4842. PMID 30666870. S2CID 58623597.