(2R,4R,5R)-2-[2-chloro-6-(cyclopentylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 164716
• Molecular Formular: C15H20ClN5O4
• Molecular Mass: 369.8034
• Monoisotopic Mass: 369.12038183
• SMILES: n1c(nc2c(c1NC1CCCC1)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O)Cl
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1nc(Cl)nc2NC1CCCC1
• InChI: InChI=1S/C15H20ClN5O4/c16-15-19-12(18-7-3-1-2-4-7)9-13(20-15)21(6-17-9)14-11(24)10(23)8(5-22)25-14/h6-8,10-11,14,22-24H,1-5H2,(H,18,19,20)/t8-,10+,11?,14-/m1/s1
• InChIKey: XSMYYYQVWPZWIZ-XNZUMOJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-[2-chloro-6-(cyclopentylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-[2-chloro-6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2-Chloro-N-cyclopentyladenosine; CCPA; 2-Chloro-N6-cyclopentyl Adenosine

Database IDs

• CAS Number: 37739-05-2
• PubChem SID: 162258851
• PubChem CID: 23818609

CALCULATED PROPERTIES

• Acid pKa: 12.45397
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.47398698
• LogD (pH = 7.4): 0.47398853
• Log P: 0.4739924
• Molar Refractivity: 90.6008 cm^3
• Polarizability: 35.012794 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C427650

Adenosine receptors are for treating central nervous system (CNS) disorders. Adenosine A1 receptor agonists include e.g. CCPA, 8-cyclopentyl-1,3-dipropylxanthine, R-phenylisopropyl adenosine. A2A receptor agonists include e.g. regadenoson (Lexiscan), apad

REFERENCES

• Arch, J., et al.: Biochem. J., 174, 965 (1978)
• Agnati, L., et al.: Pharmacol. Rev., 55, 509 (1978)
• Badman, M., et al.: Science, 307, 1909 (1978)