2-amino-9-{[2-hydroxy(2H4)ethoxy]methyl}-9H-purin-6-ol

• ChemBase ID: 159438
• 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-hydroxy(^2H₄)ethoxy]methyl}-9H-purin-6-ol
• IUPAC Traditional name: 2-amino-9-{[2-hydroxy(^2H₄)ethoxy]methyl}purin-6-ol
• Synonyms: 2-Amino-1,9-dihydro-9-[(2-hydroxyethoxy-d4)methyl]-6H-Purin-6-one; 9-[(2-Hydroxyethoxy-d4)methyl]guanine; Acycloguanosine-d4; Acicloftal-d4; Cargosil-d4; Gerpevir-d4; Herpevir-d4; Zovirax-d4; Zyclir-d4; Acyclovir-d4

Database IDs

• PubChem SID: 162253573
• PubChem CID: 45038087

CALCULATED PROPERTIES

• 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: 20.915857 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 11.583661

PROPERTIES

Physical Property

• Solubility: Acetic Acid; DMF; DMSO
• Apperance: Off-White Solid
• Melting Point: >245°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A192402

Orally active acyclic labelled 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)