CHEBI:20689 - 6-O-methylguanine

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ChEBI Name 6-O-methylguanine
ChEBI ID CHEBI:20689
ChEBI ASCII Name 6-O-methylguanine
Definition A methylguanine in which the methyl group is positioned on the oxygen at position 6. Formed in DNA by alkylation of the oxygen atom of guanine, most often by N-nitroso compounds and sometimes due to methylation by other compounds such as endogenous S-adenosylmethionine, it base-pairs to thymine rather than cytidine, causing a G:C to A:T transition in DNA.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C6H7N5O
Net Charge 0
Average Mass 165.15270
Monoisotopic Mass 165.065
InChI InChI=1S/C6H7N5O/c1-12-5-3-4(9-2-8-3)10-6(7)11-5/h2H,1H3,(H3,7,8,9,10,11)
InChIKey BXJHWYVXLGLDMZ-UHFFFAOYSA-N
SMILES COc1nc(N)nc2nc[nH]c12
Roles Classification
Biological Role(s): mutagen
An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
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ChEBI Ontology
Outgoing 6-O-methylguanine (CHEBI:20689) has role mutagen (CHEBI:25435)
6-O-methylguanine (CHEBI:20689) is a methylguanine (CHEBI:25305)
IUPAC Name
6-methoxy-7H-purin-2-amine
Synonyms Sources
2-Amino-6-methoxypurine ChemIDplus
6-Methoxy-1H-purine-2-amine ChemIDplus
6-Methoxyguanine ChemIDplus
O-(6)-Methylguanine ChemIDplus
O6-methylguanine ChemIDplus
Manual Xref Database
6-O-Methylguanine Wikipedia
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Registry Numbers Types Sources
20535-83-5 CAS Registry Number ChemIDplus
5334996 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1474583 PubMed citation Europe PMC
15239064 PubMed citation Europe PMC
22185597 PubMed citation Europe PMC
2271591 PubMed citation Europe PMC
Last Modified
22 June 2016