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

• ChemBase ID: 159441
• Molecular Formular: C14H22N6O4
• Molecular Mass: 338.36228
• Monoisotopic Mass: 338.17025321
• SMILES: n1c(nc2c(c1O)ncn2COCCOC(=O)[C@H]([C@@H](C)CC)N)N
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)OCCOCn1cnc2c1nc(N)nc2O)N)C
• InChI: InChI=1S/C14H22N6O4/c1-3-8(2)9(15)13(22)24-5-4-23-7-20-6-17-10-11(20)18-14(16)19-12(10)21/h6,8-9H,3-5,7,15H2,1-2H3,(H3,16,18,19,21)/t8-,9-/m0/s1
• InChIKey: DYTMGBXTNHPPNK-IUCAKERBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]ethyl (2S,3S)-2-amino-3-methylpentanoate
• IUPAC Traditional name: 2-[(2-amino-6-hydroxypurin-9-yl)methoxy]ethyl (2S,3S)-2-amino-3-methylpentanoate
• Synonyms: L-Isoleucine 2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl Ester; Acyclovir L-Isoleucinate

Database IDs

• CAS Number: 142963-63-1
• PubChem SID: 162253576
• PubChem CID: 492654

CALCULATED PROPERTIES

• Acid pKa: 11.584627
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.0797989
• LogD (pH = 7.4): 0.52152014
• Log P: 0.85873115
• Molar Refractivity: 86.1699 cm^3
• Polarizability: 33.59723 Å^3
• Polar Surface Area: 151.4 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A192420

Acyclovir (A192400) impurity. An Acyclovir amino acid ester prodrug.

REFERENCES

• Goskonda, V., et al.: J. Pharm. Sci., 88, 180 (1999)
• Chang, J., et al.: Pharm. Res., 17, 670 (1999)