6-amino-8,9-dihydro-7H-purin-8-one

• ChemBase ID: 179751
• Molecular Formular: C5H5N5O
• Molecular Mass: 151.1261
• Monoisotopic Mass: 151.04940981
• SMILES: [nH]1c2c([nH]c1=O)c(ncn2)N
• Canonical SMILES: O=c1[nH]c2c([nH]1)ncnc2N
• InChI: InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-3)10-5(11)9-2/h1H,(H4,6,7,8,9,10,11)
• InChIKey: RGKBRPAAQSHTED-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-8,9-dihydro-7H-purin-8-one
• IUPAC Traditional name: 6-amino-8,9-dihydro-7H-purin-8-one
• Synonyms: 6-Amino-1,7-dihydro-8 H -purin-8-one; 6-Amino-8-purinol; 7,8-Dihydro-8- oxoadenine; 8-Hydroxyadenine; 8-Oxoadenine

Database IDs

• CAS Number: 21149-26-8
• PubChem SID: 164235661
• PubChem CID: 5355054

CALCULATED PROPERTIES

• Acid pKa: 10.584477
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.42760482
• LogD (pH = 7.4): -0.41850373
• Log P: -0.41811192
• Molar Refractivity: 41.9865 cm^3
• Polarizability: 13.250684 Å^3
• Polar Surface Area: 92.93 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Induces misincorporation in in vitro DNA synthesis and mutation in NIH 3T3; Inhibits or blocks WRNp

Product Information

• Biological Source: Found in the urine of humans suffering from leukaemia. Isol. from the ascidian Symplegma rubra
• Application(s): DNA mismatch in mutagenesis

REFERENCES

• Robins, R.K., J.A.C.S., 1958, 80, 6671-6679, (synth, uv)
• Brown, T. et al., Chem. Br., 1993, 29, 484-486, (rev)
• Lindsay, B.S. et al., J. Nat. Prod., 1999, 62, 1573-1575, (isol)
• Madyastha, K.M. et al., J.C.S. Perkin 1, 1999, 677-680, (isol)