({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)({[(propan-2-yloxy)carbonyl]oxy}methoxy)phosphinic acid

• ChemBase ID: 174767
• Molecular Formular: C14H22N5O7P
• Molecular Mass: 403.327541
• Monoisotopic Mass: 403.1256847
• SMILES: n1cnc2c(c1N)ncn2C[C@H](OCP(=O)(OCOC(=O)OC(C)C)O)C
• Canonical SMILES: C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(OCOC(=O)OC(C)C)O
• InChI: InChI=1S/C14H22N5O7P/c1-9(2)26-14(20)23-7-25-27(21,22)8-24-10(3)4-19-6-18-11-12(15)16-5-17-13(11)19/h5-6,9-10H,4,7-8H2,1-3H3,(H,21,22)(H2,15,16,17)/t10-/m1/s1
• InChIKey: XLYSRKLPLHUWCJ-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)({[(propan-2-yloxy)carbonyl]oxy}methoxy)phosphinic acid
• IUPAC Traditional name: {[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxy}methyl[(isopropoxycarbonyl)oxy]methoxyphosphinic acid
• Synonyms: (8R)-9-(6-Amino-9H-purin-9-yl)-5-hydroxy-8-methyl-2,4,7-trioxa-5-phosphanonanoic Acid 1-Methylethyl Ester 5-Oxide; Tenofovir Monoisoproxil; Mono-POC Tenofovir (Mixture of Diastereomers)

Database IDs

• CAS Number: 211364-69-1
• PubChem SID: 164230677
• PubChem CID: 56925685

CALCULATED PROPERTIES

• Acid pKa: 1.065689
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -1.6680146
• LogD (pH = 7.4): -1.5431755
• Log P: -2.3145697
• Molar Refractivity: 93.0616 cm^3
• Polarizability: 36.70296 Å^3
• Polar Surface Area: 160.91 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 303-305°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M567000

An impurity of Tenofovir disoproxil (T018505).

REFERENCES

• Gan, L., et al.: Drug Metab. Dispos., 24, 344 (1996)
• Annaert, P., et al.: Pharm. Res., 14, 492 (1996)
• Naesens, L., et al.: Antimicrob. Agents Chemother., 42, 1568 (1996)