{2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]ethoxy}phosphonic acid

• ChemBase ID: 159445
• Molecular Formular: C8H12N5O6P
• Molecular Mass: 305.184541
• Monoisotopic Mass: 305.05251976
• SMILES: n1c(nc2c(c1O)ncn2COCCOP(=O)(O)O)N
• Canonical SMILES: Nc1nc(O)c2c(n1)n(COCCOP(=O)(O)O)cn2
• InChI: InChI=1S/C8H12N5O6P/c9-8-11-6-5(7(14)12-8)10-3-13(6)4-18-1-2-19-20(15,16)17/h3H,1-2,4H2,(H2,15,16,17)(H3,9,11,12,14)
• InChIKey: KUOAJOVOKFATQE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]ethoxy}phosphonic acid
• IUPAC Traditional name: 2-[(2-amino-6-hydroxypurin-9-yl)methoxy]ethoxyphosphonic acid
• Synonyms: 2-Amino-1,9-dihydro-9-[[2-(phosphonooxy)ethoxy]methyl]-6H-purin-6-one; Acycloguanosine Monophosphate; Acyclovir Monophosphate

Database IDs

• CAS Number: 66341-16-0
• PubChem SID: 162253580
• PubChem CID: 83999

CALCULATED PROPERTIES

• Acid pKa: 1.3926699
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.1264138
• LogD (pH = 7.4): -4.2245183
• Log P: -1.1133168
• Molar Refractivity: 66.4411 cm^3
• Polarizability: 25.456053 Å^3
• Polar Surface Area: 165.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A192500

A nucleoside analog phosphates for topical use in the treatment of herpes virus infections. A topical treatment that seems to bypass a key mechanism responsible for resistance to Acyclovir.

REFERENCES

• Furman, P., et al.: J. Virol., 32, 72 (1979)
• Darby, G., et al.: J. Gen. Virol., 48, 451 (1979)
• Prisbe, E., et al.: J. Med. Chem., 29, 671 (1979)
• Ellis, M., et al.: Antimicrob. Agents Chemother., 33, 304 (1979)