isoguanine

Also known as 6-amino-7H-purin-2-ol, 6-amino-9H-purin-2-ol, 6-amino-3,9-dihydro-2H-purin-2-one, 2-hydroxyadenine, 2-oxoadenine, 6-amino-3,7-dihydro-purin-2-one, 6-amino-1,3-dihydro-2H-purin-2-one

Isoguanine or 2-hydroxyadenine is a purine base that is an isomer of guanine. The nucleoside form is called isoguanosine (iG).

Chemical data

Formula: C5H5N5O
Molecular weight: 151.13 g/mol
IUPAC name: 6-amino-1,7-dihydropurin-2-one
SMILES: C1=NC2=NC(=O)NC(=C2N1)N
InChIKey: DRAVOWXCEBXPTN-UHFFFAOYSA-N
XLogP: -1.7
Polar surface area: 91.9 Å²
H-bond donors: 3
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 151.049

Show 4 more facts

chemical formula: C₅H₅N₅O
canonical SMILES: C1=NC2=NC(=O)NC(=C2N1)N
Commons category: Isoguanine
found in taxon: Streptomyces

Sources (1)

wikidata.org

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Encyclopedic overview

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Contents

References

Isoguanine or 2-hydroxyadenine is a purine base that is an isomer of guanine. The nucleoside form is called isoguanosine (iG).

It is a product of oxidative damage to DNA in cultured E. coli and human cells. However, newer evidence shows that it mainly occurs in RNA and as the ribonucleoside instead of in DNA or as deoxyribonucleoside in living mammals, calling into question its link with DNA in vivo.

Excerpted from Wikipedia’s “isoguanine” article, available under the CC BY-SA 4.0 licence.