2-amino-9-[(2-hydroxyethoxy)methyl]-9H-purin-6-ol

• ChemBase ID: 159437
• Molecular Formular: C8H11N5O3
• Molecular Mass: 225.20464
• Monoisotopic Mass: 225.08618924
• SMILES: n1c(nc2c(c1O)ncn2COCCO)N
• Canonical SMILES: OCCOCn1cnc2c1nc(N)nc2O
• InChI: InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15)
• InChIKey: MKUXAQIIEYXACX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2-hydroxyethoxy)methyl]-9H-purin-6-ol
• IUPAC Traditional name: 2-amino-9-[(2-hydroxyethoxy)methyl]purin-6-ol
• Synonyms: 2-Amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-6H-purin-6-one; 9-[(2-Hydroxyethoxy)methyl]guanine; Acycloguanosine; Acicloftal; Cargosil; Gerpevir; Herpevir; Zovirax; Zyclir; Acyclovir

Database IDs

• CAS Number: 59277-89-3
• PubChem SID: 162253572
• PubChem CID: 2022

CALCULATED PROPERTIES

• Acid pKa: 11.583661
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.55910313
• LogD (pH = 7.4): -0.5591207
• Log P: -0.5590925
• Molar Refractivity: 55.5682 cm^3
• Polarizability: 20.915855 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetic Acid; DMF; DMSO
• Apperance: White Solid
• Melting Point: 253-255°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A192400

Orally active acyclic nucleoside with inhibitory activity towards several herpes viruses. Antiviral.

REFERENCES

• Collins, P., et al.: J. Antimicrob. Chemother., 5, 431 (1979)
• Matsumoto, H., et al.: Chem. Pharm. Bull., 36, 1153 (1979)
• Whitley, R.J., et al.: N. Engl. J. Med., 327, 782 (1979)