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

• ChemBase ID: 174975
• Molecular Formular: C22H23N5O5
• Molecular Mass: 437.44852
• Monoisotopic Mass: 437.16991886
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)OCCc1cc2c(cc1)cccc2)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1nc(OCCc1ccc3c(c1)cccc3)nc2N
• InChI: InChI=1S/C22H23N5O5/c23-19-16-20(27(11-24-16)21-18(30)17(29)15(10-28)32-21)26-22(25-19)31-8-7-12-5-6-13-3-1-2-4-14(13)9-12/h1-6,9,11,15,17-18,21,28-30H,7-8,10H2,(H2,23,25,26)/t15-,17?,18+,21-/m1/s1
• InChIKey: LCDBQJZQQFLFGG-IPZUKPMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-{6-amino-2-[2-(naphthalen-2-yl)ethoxy]-9H-purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-{6-amino-2-[2-(naphthalen-2-yl)ethoxy]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2-[2-(2-Naphthylethoxy)adenosine]; WRC 0018; 2-[2-(2-Naphthalenyl)ethoxy]adenosine

Database IDs

• CAS Number: 131865-99-1
• PubChem SID: 164230885
• PubChem CID: 71750933

CALCULATED PROPERTIES

• Acid pKa: 12.454001
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 1.4327477
• LogD (pH = 7.4): 1.432758
• Log P: 1.4327619
• Molar Refractivity: 115.4226 cm^3
• Polarizability: 45.76348 Å^3
• Polar Surface Area: 148.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N368400

Adenosine A2 receptor agonist.

REFERENCES

• Matova, M., et al.: Drug Des. Discov., 16, 255 (2000)
• Gao, Z., et al.: Biochem. Pharmacol., 68, 1985 (2000)
• Adachi, H., et al.: J. Med. Chem., 50, 1810 (2000)