2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]ethyl (2S)-2-formamido-3-methylbutanoate

• ChemBase ID: 169438
• Molecular Formular: C14H20N6O5
• Molecular Mass: 352.3458
• Monoisotopic Mass: 352.14951777
• SMILES: n1c(nc2c(c1O)ncn2COCCOC(=O)[C@H](C(C)C)NC=O)N
• Canonical SMILES: O=CN[C@H](C(=O)OCCOCn1cnc2c1nc(N)nc2O)C(C)C
• InChI: InChI=1S/C14H20N6O5/c1-8(2)9(17-6-21)13(23)25-4-3-24-7-20-5-16-10-11(20)18-14(15)19-12(10)22/h5-6,8-9H,3-4,7H2,1-2H3,(H,17,21)(H3,15,18,19,22)/t9-/m0/s1
• InChIKey: AYGHYIMPMGWQND-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]ethyl (2S)-2-formamido-3-methylbutanoate
• IUPAC Traditional name: 2-[(2-amino-6-hydroxypurin-9-yl)methoxy]ethyl (2S)-2-formamido-3-methylbutanoate
• Synonyms: N-Formyl-L-valine 2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl Ester; N-Formyl Valacyclovir

Database IDs

• CAS Number: 847670-62-6
• PubChem SID: 162263570
• PubChem CID: 11595512

CALCULATED PROPERTIES

• Acid pKa: 11.53474
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 0.18429944
• LogD (pH = 7.4): 0.18427917
• Log P: 0.18431039
• Molar Refractivity: 86.5222 cm^3
• Polarizability: 33.366875 Å^3
• Polar Surface Area: 154.48 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: White Solid
• Melting Point: 156-158°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F701570

Valacyclovir (V085000) impurity.

REFERENCES

• Furman, P., et al.: Antimicrob. Agents Chemother., 20, 518 (1981)