2-[(2-{[({9-[(2-{[(2S)-2-amino-3-methylbutanoyl]oxy}ethoxy)methyl]-6-oxo-6,9-dihydro-1H-purin-2-yl}amino)methyl]amino}-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate

• ChemBase ID: 162441
• Molecular Formular: C27H40N12O8
• Molecular Mass: 660.6821
• Monoisotopic Mass: 660.3092063
• SMILES: [nH]1c(nc2c(c1=O)ncn2COCCOC(=O)[C@H](C(C)C)N)NCNc1[nH]c(=O)c2c(n1)n(cn2)COCCOC(=O)[C@H](C(C)C)N
• Canonical SMILES: CC([C@@H](C(=O)OCCOCn1cnc2c1nc(NCNc1[nH]c(=O)c3c(n1)n(COCCOC(=O)[C@H](C(C)C)N)cn3)[nH]c2=O)N)C
• InChI: InChI=1S/C27H40N12O8/c1-14(2)16(28)24(42)46-7-5-44-12-38-10-32-18-20(38)34-26(36-22(18)40)30-9-31-27-35-21-19(23(41)37-27)33-11-39(21)13-45-6-8-47-25(43)17(29)15(3)4/h10-11,14-17H,5-9,12-13,28-29H2,1-4H3,(H2,30,34,36,40)(H2,31,35,37,41)/t16-,17-/m0/s1
• InChIKey: WLNNOXICHLWLAK-IRXDYDNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-{[({9-[(2-{[(2S)-2-amino-3-methylbutanoyl]oxy}ethoxy)methyl]-6-oxo-6,9-dihydro-1H-purin-2-yl}amino)methyl]amino}-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
• IUPAC Traditional name: 2-[(2-{[({9-[(2-{[(2S)-2-amino-3-methylbutanoyl]oxy}ethoxy)methyl]-6-oxo-1H-purin-2-yl}amino)methyl]amino}-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
• Synonyms: Bis Valacyclovir (~90%)

Database IDs

• CAS Number: 1356019-51-6
• PubChem SID: 162256576
• PubChem CID: 71314121

CALCULATED PROPERTIES

• Acid pKa: 9.649271
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): -4.5498557
• LogD (pH = 7.4): -1.3427628
• Log P: -0.6588303
• Molar Refractivity: 164.5247 cm^3
• Polarizability: 62.767723 Å^3
• Polar Surface Area: 265.72 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 155-159°C

Safety Information

• Storage Condition: Amber Vial, -86?C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B588950

This impurity is listed in Ph. Eur. monograph for Valaciclovir HCl as impurity P and Bis-valaciclovir in USP monograph (impurity K).