ethyl 1-{6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-2-yl}-1H-pyrazole-4-carboxylate

• ChemBase ID: 160477
• Molecular Formular: C16H19N7O6
• Molecular Mass: 405.36536
• Monoisotopic Mass: 405.13968136
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)n1cc(cn1)C(=O)OCC)N)CO)O)O
• Canonical SMILES: CCOC(=O)c1cnn(c1)c1nc(N)c2c(n1)n(cn2)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CO
• InChI: InChI=1S/C16H19N7O6/c1-2-28-15(27)7-3-19-23(4-7)16-20-12(17)9-13(21-16)22(6-18-9)14-11(26)10(25)8(5-24)29-14/h3-4,6,8,10-11,14,24-26H,2,5H2,1H3,(H2,17,20,21)/t8-,10-,11-,14-/m1/s1
• InChIKey: ZPVLTIXYQGANFL-IDTAVKCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-{6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-2-yl}-1H-pyrazole-4-carboxylate
• IUPAC Traditional name: ethyl 1-{6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl}pyrazole-4-carboxylate
• Synonyms: CVT 3127; 1-(6-Amino-9-β-D-ribofuranosyl-9H-purin-2-yl)-1H-pyrazole-4-carboxylic AcidEthyl Ester

Database IDs

• CAS Number: 313348-16-2
• PubChem SID: 162254612
• PubChem CID: 9865974

CALCULATED PROPERTIES

• Acid pKa: 12.454002
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -0.96611476
• LogD (pH = 7.4): -0.96607876
• Log P: -0.9660744
• Molar Refractivity: 98.2772 cm^3
• Polarizability: 37.310795 Å^3
• Polar Surface Area: 183.66 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Formamide
• Apperance: Yellow Powder

DETAILS

Toronto Research Chemicals - A629210

Short-acting A2A adenosine receptor agonists.

REFERENCES

• Gao, Z. et al.; J. Pharmacol. Exp. Ther. 298, 209 (2001)