3-(2-amino-6-oxo-6,7-dihydro-1H-purin-7-yl)-2-hydroxypropanamide

• ChemBase ID: 163619
• Molecular Formular: C8H10N6O3
• Molecular Mass: 238.2034
• Monoisotopic Mass: 238.08143821
• SMILES: [nH]1c(nc2c(c1=O)n(cn2)CC(C(=O)N)O)N
• Canonical SMILES: NC(=O)C(Cn1cnc2c1c(=O)[nH]c(n2)N)O
• InChI: InChI=1S/C8H10N6O3/c9-5(16)3(15)1-14-2-11-6-4(14)7(17)13-8(10)12-6/h2-3,15H,1H2,(H2,9,16)(H3,10,12,13,17)
• InChIKey: JYHHZNJOFXOGSQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-amino-6-oxo-6,7-dihydro-1H-purin-7-yl)-2-hydroxypropanamide
• IUPAC Traditional name: 3-(2-amino-6-oxo-1H-purin-7-yl)-2-hydroxypropanamide
• Synonyms: N7-GA-Gua; 2-Amino-1,6-dihydro-α-hydroxy-6-oxo-7H-purine-7-propanamide; N7-(2-Carbamoyl-2-hydroxyethyl)guanine

Database IDs

• CAS Number: 163734-06-3
• PubChem SID: 162257754
• PubChem CID: 46783716

CALCULATED PROPERTIES

• Acid pKa: 10.712038
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.690507
• LogD (pH = 7.4): -2.690566
• Log P: -2.6903787
• Molar Refractivity: 58.1756 cm^3
• Polarizability: 20.572065 Å^3
• Polar Surface Area: 148.62 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: N/A

DETAILS

Toronto Research Chemicals - C175875

A DNA adduct of glycidamide.

REFERENCES

• Bergmark, E., et al.: Toxicol. Appl. Pharmacol., 111, 352 (1991)
• Swenberg, J.A., et al.: Toxicol. Lett., 82, 751 (1991)