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
KEGG	C17206;
PubChem CID	304590;
UNII	F2SUM4W8EB;
CompTox Dashboard (EPA)	DTXSID40922994 ;
	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;
	SMILES O=CC1=CNC(=O)NC1=O;
Properties
Chemical formula	C5H4N2O3
Molar mass	140.098 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	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

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

^ 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.
^ 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.

[MyUser_Ncbi.nlm.nih.gov_August_5_2015c-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.

[1]

[2]