(2R,4R,5R)-2-(6-{[(1R)-2,3-dihydro-1H-inden-1-yl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 167636
• Molecular Formular: C19H21N5O4
• Molecular Mass: 383.40114
• Monoisotopic Mass: 383.15935418
• SMILES: n1cnc2c(c1N[C@@H]1CCc3c1cccc3)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1ncnc2N[C@@H]1CCc2c1cccc2
• InChI: InChI=1S/C19H21N5O4/c25-7-13-15(26)16(27)19(28-13)24-9-22-14-17(20-8-21-18(14)24)23-12-6-5-10-3-1-2-4-11(10)12/h1-4,8-9,12-13,15-16,19,25-27H,5-7H2,(H,20,21,23)/t12-,13-,15+,16?,19-/m1/s1
• InChIKey: FSKMJUWPFLDDRS-LPKVUCDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-(6-{[(1R)-2,3-dihydro-1H-inden-1-yl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-{6-[(1R)-2,3-dihydro-1H-inden-1-ylamino]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: N-[(1R)-2,3-Dihydro-1H-inden-1-yl]adenosine; CI 947; PD 117519; (R)-N-(2,3-Dihydro-1H-indenyl)adenosine

Database IDs

• CAS Number: 96392-15-3
• PubChem SID: 162261769
• PubChem CID: 71316175

CALCULATED PROPERTIES

• Acid pKa: 12.453623
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.39759493
• LogD (pH = 7.4): 0.47829896
• Log P: 0.47943756
• Molar Refractivity: 100.8824 cm^3
• Polarizability: 38.73194 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D449160

N6-Substituted adenosine receptor agonist; a potential antihypertensive agent.

REFERENCES

• Daly, J., et al.: Biochem. Pharmacol., 43, 1089 (1992)
• Fredholm, B., et al.: Pharmacol. Rev., 53, 527 (1992)
• van Tilburg, E., et al.: J. Med. Chem., 44, 2966 (1992)
• Gao, Z., et al.: J. Biol. Chem., 277, 19056 (1992)