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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.162.784
  • 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) checkY
    Key: FPGSEBKFEJEOSA-UHFFFAOYSA-N checkY
  • 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
  • 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
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

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.


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