2-amino-7-[(2-hydroxyethoxy)methyl]-6,7-dihydro-1H-purin-6-one

• ChemBase ID: 170569
• Molecular Formular: C8H11N5O3
• Molecular Mass: 225.20464
• Monoisotopic Mass: 225.08618924
• SMILES: [nH]1c(nc2c(c1=O)n(cn2)COCCO)N
• Canonical SMILES: OCCOCn1cnc2c1c(=O)[nH]c(n2)N
• InChI: InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)13(3-10-6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15)
• InChIKey: ZEJSSOYUBQMVHC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-7-[(2-hydroxyethoxy)methyl]-6,7-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-7-[(2-hydroxyethoxy)methyl]-1H-purin-6-one
• Synonyms: 2-Amino-1,7-dihydro-7-[(2-hydroxyethoxy)methyl]-6H-purin-6-one; N7-[(2-Hydroxyethoxy)methyl)guanine

Database IDs

• CAS Number: 91702-61-3
• PubChem SID: 164226479
• PubChem CID: 472811

CALCULATED PROPERTIES

• Acid pKa: 10.682223
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.5103658
• LogD (pH = 7.4): -1.5104505
• Log P: -1.5102502
• Molar Refractivity: 56.3765 cm^3
• Polarizability: 19.994377 Å^3
• Polar Surface Area: 114.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942195

N7-[(2-Hydroxyethoxy)methyl)guanine is the 7-isomeric impurity of the antiviral drug Acyclovir (A192400).

REFERENCES

• Poluektova, L. et al.: Int. J. Immunopharmacol., 18, 429 (1996)
• Huidobro, A.L. et al.: J. Pharmac. Biomed. Anal., 37, 687 (1996)