Compound: Isoguanine
SMILES: O=c1nc2nc[nH]c2c([nH]1)N
InChIKey: DRAVOWXCEBXPTN-UHFFFAOYSA-N
Synonyms: Isoguanine, 3373-53-3, 2-hydroxyadenine, 6-amino-7H-purin-2-ol, 6-Amino-1,3-dihydro-2H-purin-2-one, 6-amino-1,7-dihydropurin-2-one, 2-oxoadenine, 2-Oxyadenine, CHEBI:62462, E335PK4428, NSC-241501, DTXSID00187406, 2-OH-Ade, RefChem:149393, DTXCID70109897, 222-157-6, 6-amino-3,7-dihydro-2H-purin-2-one, 2-Hydroxy-6-aminopurine, 6-Amino-2-hydroxypurine, 6-amino-9H-purin-2-ol, 149297-79-0, Fludarabine PHosphate impurity B, Fludarabine Phosphate EP Impurity B, MFCD00142931, 6-amino-3,9-dihydro-2H-purin-2-one, isoguanin, UNII-E335PK4428, EINECS 222-157-6, 6-aminopurin-2-ol, dihydro-2-oxoadenine, GUANOPTERIN, NSC 241501, 6-amino-2,3-dihydro-1H-purin-2-one, 2H-Purin-2-one, 6-amino-1,3-dihydro-, purine, 6-amino-2-hydroxy-, SCHEMBL134675, SCHEMBL134676, SCHEMBL156950, SCHEMBL432772, SCHEMBL887740, SCHEMBL887741, SCHEMBL999051, 2H-Purin-2-one,3-dihydro-, CHEMBL506639, orb1307044, SCHEMBL3666185, SCHEMBL4058595, SCHEMBL4748766, SCHEMBL6545701, SCHEMBL6545704, SCHEMBL6678737, SCHEMBL29569323, MSK6933, DRAVOWXCEBXPTN-UHFFFAOYSA-N, 6-amino-3,7-dihydropurin-2-one, 6-amino-3,9-dihydropurin-2-one, 6-amino-3,7-dihydro-purin-2-one, 6-Amino-3,9-dihydro-purin-2-one, BDBM50497031, CCG-47772, MFCD00070574, NSC241501, SBB066301, STL454962, 6-Amino-9H-purin-2-ol, AldrichCPR, AKOS006229677, AKOS015854519, AKOS015896923, AKOS015904753, AKOS016008986, DS-5009, EBC-615543, 6-Amino-1,7-dihydro-2H-purin-2-one, 6-amino-3,7(9)-dihydro-purin-2-one, ST092936, SY057869, HY-124143, CS-0084463, I0370, NS00029534, C74731, EN300-2924752, 2H-PURIN-2-ONE, 6-AMINO-3,7-DIHYDRO-, Q6085780, SR-01000637365-1, FLUDARABINE PHOSPHATE IMPURITY B [EP IMPURITY], 6-Amino-7H-purin-2-ol; Fludarabine Phosphate EP Impurity B, FLUDARABINE PHOSPHATE IMPURITY, ISOGUANINE [USP IMPURITY], IGA
Theoretical properties:
molecular_formula: C5H5N5O
molecular_weight: 151.13 g/mol
exact_mass: 151.04940980 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 11
topological_polar_surface_area: 91.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: > 360 °C
solubility: 0.0625 mg/mL
Descriptions:
pubchem: Isoguanine is an oxopurine that is 3,7-dihydro-purin-2-one in which the hydrogen at position 6 is substituted by an amino group.
chebi: An oxopurine that is 3,7-dihydro-purin-2-one in which the hydrogen at position 6 is substituted by an amino group.
chembl: ISOGUANINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 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.
It can be mutagenic by causing mispairing, but does not hinder replication.

It is also used in combination with isocytosine in studies of unnatural nucleic acid analogues of the normal base pairs in DNA. It is used as a nucleobase of hachimoji nucleic acids where it is given the abbreviation B. In hachimoji DNA, it pairs with 1-methylcytosine, while in hachimoji RNA, it pairs with isocytosine.