8-Oxoguanine

8-Oxoguanine: 8-Oxoguanine^[1]

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^Y

PubChem 119315

ChemSpider 106574^Y

MeSH 8-hydroxyguanine

ChEBI CHEBI:44605^Y

Jmol-3D images Image 1
Image 2

SMILES

O=C2NC=1N\C(=N/C(=O)C=1N2)N
c12=NC(=O)N=c1[nH]c(nc2=O)N

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)^Y
Key: UBKVUFQGVWHZIR-UHFFFAOYSA-N^Y
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

Properties

Molecular formula C₅H₅N₅O₂

Molar mass 167.13 g mol⁻¹

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

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 C to A 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.

8-oxoG (syn) in a Hoogsteen base pair with dA (anti)

For comparison here is a standard (non-mutagenic) GC base pair with both bases in the anti configuration of the bond between base and sugar.

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.

v · d · eNucleic acid constituents

Nucleobase
Purine (Adenine, Guanine, Purine analogue) · Pyrimidine (Uracil, Thymine, Cytosine, Pyrimidine analogue)

Nucleoside

Ribonucleoside

Adenosine · Guanosine · 5-Methyluridine · Uridine · Cytidine

Deoxyribonucleoside

Deoxyadenosine · Deoxyguanosine · Thymidine · Deoxyuridine · Deoxycytidine

Nucleotide
(Nucleoside monophosphate)

Ribonucleotide

AMP, GMP, UMP, CMP

Deoxyribonucleotide

dAMP, dGMP, dTMP, dUMP, dCMP

Cyclic nucleotide

cAMP, cGMP, c-di-GMP, cADPR

Nucleoside diphosphate
ADP, GDP, UDP, CDP · dADP, dGDP, dTDP, dCDP

Nucleoside triphosphate
ATP, GTP, m⁵UTP, UTP, CTP · dATP, dGTP, dTTP, dCTP

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i

Categories:
DNA repair
Purines

8-Oxoguanine^[1]

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^Y
PubChem	119315
ChemSpider	106574^Y
MeSH	8-hydroxyguanine
ChEBI	CHEBI:44605^Y
Jmol-3D images	Image 1 Image 2
SMILES O=C2NC=1N\C(=N/C(=O)C=1N2)N c12=NC(=O)N=c1[nH]c(nc2=O)N
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)^Y Key: UBKVUFQGVWHZIR-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₅H₅N₅O₂
Molar mass	167.13 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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8-Oxoguanine

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