9-[(2R,3R,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-2-N-phenyl-9H-purine-2,6-diamine

• ChemBase ID: 176411
• Molecular Formular: C34H60N6O4Si3
• Molecular Mass: 701.1345
• Monoisotopic Mass: 700.39838403
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)Nc1ccccc1)N)CO[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C
• Canonical SMILES: Nc1nc(Nc2ccccc2)nc2c1ncn2[C@@H]1O[C@@H]([C@H]([C@H]1O[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C)CO[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C34H60N6O4Si3/c1-32(2,3)45(10,11)41-21-24-26(43-46(12,13)33(4,5)6)27(44-47(14,15)34(7,8)9)30(42-24)40-22-36-25-28(35)38-31(39-29(25)40)37-23-19-17-16-18-20-23/h16-20,22,24,26-27,30H,21H2,1-15H3,(H3,35,37,38,39)/t24-,26-,27-,30-/m1/s1
• InChIKey: JDTKCDCRSRWMSD-BQOYKFDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,3R,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-2-N-phenyl-9H-purine-2,6-diamine
• IUPAC Traditional name: 9-[(2R,3R,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-2-N-phenylpurine-2,6-diamine
• Synonyms: 2-Phenylamino-2',3',5'-tris-O-tertbutyldimethylsilyl Adenosine

Database IDs

• PubChem SID: 164232321
• PubChem CID: 71751544

CALCULATED PROPERTIES

• Acid pKa: 13.555808
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): 8.204639
• LogD (pH = 7.4): 8.204699
• Log P: 8.2047
• Molar Refractivity: 181.1721 cm^3
• Polarizability: 77.26362 Å^3
• Polar Surface Area: 118.57 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Methanol
• Apperance: Orange Solid

DETAILS

Toronto Research Chemicals - P307800

Protected selective A2-adenosine receptor agonist. Coronary vasodilator, antihypertensive and antipsychotic following systemic administration in vivo.

REFERENCES

• Martin, et al.: Pharmacol. Biochem. Behav., 45, 951 (1993