(2R,3S,5R)-2-{6-amino-2-[2-(4-fluorophenyl)ethoxy]-9H-purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 169237
• Molecular Formular: C18H20FN5O5
• Molecular Mass: 405.3803032
• Monoisotopic Mass: 405.14484699
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)OCCc1ccc(cc1)F)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1nc(OCCc1ccc(cc1)F)nc2N
• InChI: InChI=1S/C18H20FN5O5/c19-10-3-1-9(2-4-10)5-6-28-18-22-15(20)12-16(23-18)24(8-21-12)17-14(27)13(26)11(7-25)29-17/h1-4,8,11,13-14,17,25-27H,5-7H2,(H2,20,22,23)/t11-,13?,14+,17-/m1/s1
• InChIKey: WJXSIJUIBOTFHQ-OVHGWZCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-{6-amino-2-[2-(4-fluorophenyl)ethoxy]-9H-purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-{6-amino-2-[2-(4-fluorophenyl)ethoxy]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: FPEA; 2-[2-(4-Fluorophenyl)ethoxy]adenosine

Database IDs

• CAS Number: 131865-85-5
• PubChem SID: 162263369
• PubChem CID: 71316869

CALCULATED PROPERTIES

• Acid pKa: 12.454001
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 0.58597296
• LogD (pH = 7.4): 0.58598316
• Log P: 0.58598715
• Molar Refractivity: 99.1888 cm^3
• Polarizability: 38.097706 Å^3
• Polar Surface Area: 148.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 95-100°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - F595755

Adenosine A2 receptor agonist.

REFERENCES

• Matova, M., et al.: J. Med. Chem., 32, 505 (1997)
• Matova, M., et al.: Drug Des. Discov., 16, 255 (1997)
• Adachi, H., et al.: J. Med. Chem., 50, 1810 (1997)