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

• ChemBase ID: 164537
• Molecular Formular: C18H20ClN5O5
• Molecular Mass: 421.8349
• Monoisotopic Mass: 421.11529645
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)OCCc1ccc(cc1)Cl)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1nc(OCCc1ccc(cc1)Cl)nc2N
• InChI: InChI=1S/C18H20ClN5O5/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: WUCQGGOGHZRELS-OVHGWZCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-{6-amino-2-[2-(4-chlorophenyl)ethoxy]-9H-purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-{6-amino-2-[2-(4-chlorophenyl)ethoxy]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: Sonedenoson; MRE 0094; 2-[2-(4-Chlorophenyl)ethoxy]adenosine

Database IDs

• CAS Number: 131865-88-8
• PubChem SID: 162258672
• PubChem CID: 59628422

CALCULATED PROPERTIES

• Acid pKa: 12.454001
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 1.0473157
• LogD (pH = 7.4): 1.0473258
• Log P: 1.0473299
• Molar Refractivity: 103.7772 cm^3
• Polarizability: 40.26546 Å^3
• Polar Surface Area: 148.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C379460

Adenosine A2 receptor agonist.

REFERENCES

• Gao, Z., et al.: Biochem. Pharmacol., 68, 1985 (2004)
• Desai, A., et al.: Mol. Pharmacol., 67, 1406 (2004)