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

• ChemBase ID: 165188
• Molecular Formular: C18H27N5O5
• Molecular Mass: 393.43748
• Monoisotopic Mass: 393.20121899
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)OCCC1CCCCC1)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1nc(OCCC1CCCCC1)nc2N
• InChI: InChI=1S/C18H27N5O5/c19-15-12-16(22-18(21-15)27-7-6-10-4-2-1-3-5-10)23(9-20-12)17-14(26)13(25)11(8-24)28-17/h9-11,13-14,17,24-26H,1-8H2,(H2,19,21,22)/t11-,13?,14+,17-/m1/s1
• InChIKey: VHMUQIWMOXQFBP-OVHGWZCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-[6-amino-2-(2-cyclohexylethoxy)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-[6-amino-2-(2-cyclohexylethoxy)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: WRC 0013; 2-(2-Cyclohexylethoxy)adenosine

Database IDs

• CAS Number: 131933-18-1
• PubChem SID: 162259321
• PubChem CID: 71315070

CALCULATED PROPERTIES

• Acid pKa: 12.454001
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 0.9110349
• LogD (pH = 7.4): 0.9110451
• Log P: 0.91104907
• Molar Refractivity: 100.0278 cm^3
• Polarizability: 39.161907 Å^3
• Polar Surface Area: 148.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C987920

Adenosine A2 receptor agonist.

REFERENCES

• Gao, Z., et al.: Biochem. Pharmacol., 68, 1985 (2004)
• Perez G., et al.: Bioorg. Med. Chem., 12, 2985 (2004)
• Adachi, H., et al.: J. Med. Chem., 50, 1810 (2004)