8-Hydroxyguanosine

8-Hydroxyguanosine is an RNA nucleoside which is an oxidative derivative of guanosine. Measurement of the levels of 8-hydroxyguanosine is used as a biomarker of oxidative stress causing RNA damage.[1]

8-Hydroxyguanosine

Names
IUPAC name 2-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-tetrahydrofuranyl]-3,7-dihydropurine-6,8-dione
Other names 8-Oxoguanosine
Identifiers
CAS Number	3868-31-3^N
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL1688964^N
ChemSpider	228049^Y
ECHA InfoCard	100.162.784
PubChem CID	65131
CompTox Dashboard (EPA)	DTXSID50959514
InChI InChI=1S/C10H13N5O6/c11-9-13-6-3(7(19)14-9)12-10(20)15(6)8-5(18)4(17)2(1-16)21-8/h2,4-5,8,16-18H,1H2,(H,12,20)(H3,11,13,14,19)^Y Key: FPGSEBKFEJEOSA-UHFFFAOYSA-N^Y InChI=1/C10H13N5O6/c11-9-13-6-3(7(19)14-9)12-10(20)15(6)8-5(18)4(17)2(1-16)21-8/h2,4-5,8,16-18H,1H2,(H,12,20)(H3,11,13,14,19) Key: FPGSEBKFEJEOSA-UHFFFAOYAG
SMILES C(C1C(C(C(O1)N2C3=C(C(=O)N=C(N3)N)NC2=O)O)O)O O=C3/N=C(/N)NC\1=C3\NC(=O)N/1C2OC(C(O)C2O)CO
Properties
Chemical formula	C10H13N5O6
Molar mass	299.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

• 8-Oxo-2'-deoxyguanosine

References

1. Cattley RC, Glover SE (1993). "Elevated 8-hydroxydeoxyguanosine in hepatic DNA of rats following exposure to peroxisome proliferators: relationship to carcinogenesis and nuclear localization". Carcinogenesis. 14 (12): 2495–2499. doi:10.1093/carcin/14.12.2495. PMID 8269617.