8-Oxoguanine

8-Oxoguanine^[1]
Names
	IUPAC name 2-Amino-7,9-dihydro-1H-purine-6,8-dione
	Other names 8-Oxo-7,8-dihydroguanine
Identifiers
CAS Number	5614-64-2 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:44605 ;
ChemSpider	106574 ;
ECHA InfoCard	100.024.578
MeSH	8-hydroxyguanine
PubChem CID	119315;
CompTox Dashboard (EPA)	DTXSID60231515 ;
	InChI InChI=1S/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H3,6,8,9,10,11,12) Key: UBKVUFQGVWHZIR-UHFFFAOYSA-N ; InChI=1/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12) Key: CLGFIVUFZRGQRP-UHFFFAOYAZ; InChI=1/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H3,6,8,9,10,11,12) Key: UBKVUFQGVWHZIR-UHFFFAOYAW;
	SMILES O=C2NC=1N\C(=N/C(=O)C=1N2)N; c12=NC(=O)N=c1[nH]c(nc2=O)N;
Properties
Chemical formula	C5H5N5O2
Molar mass	167.128 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

8-Oxoguanine (8-hydroxyguanine, 8-oxo-Gua, or OH⁸Gua) is one of the most common DNA lesions resulting from reactive oxygen species ^[2] and can result in a mismatched pairing with Adenine resulting in G to T and A to C substitutions in the genome.^[3] In humans, it is primarily repaired by the DNA glycosylase OGG1. It can be caused by ionizing radiation, in connection with oxidative metabolism.

References

^ 8-hydroxyguanine - Compound Summary, PubChem
^ S. Kanvah, et al., Oxidation of DNA: Damage to Nucleobases; Acc. Chem. Res. 2010, 43(2), 280-287
^ Cheng KC, Cahill DS, Kasai H, Nishimura S, Loeb LA (1992 Jan 5). "8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G→T and A→C substitutions". J Biol Chem. 267 (1): 166–72. PMID 1730583. {{cite journal}}: Check date values in: |date= (help)CS1 maint: multiple names: authors list (link)

[1] 8-hydroxyguanine - Compound Summary, PubChem

[2] S. Kanvah, et al., Oxidation of DNA: Damage to Nucleobases; Acc. Chem. Res. 2010, 43(2), 280-287

[3] Cheng KC, Cahill DS, Kasai H, Nishimura S, Loeb LA (1992 Jan 5). "8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G→T and A→C substitutions". J Biol Chem. 267 (1): 166–72. PMID 1730583. {{cite journal}}: Check date values in: |date= (help)CS1 maint: multiple names: authors list (link)

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