N-{[(2R,3S,4R,5R)-5-[6-(benzylamino)-9H-purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl}propanamide

• ChemBase ID: 105635
• Molecular Formular: C20H24N6O4
• Molecular Mass: 412.44236
• Monoisotopic Mass: 412.18590328
• SMILES: CCC(=O)NC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c1ncnc2NCc1ccccc1
• Canonical SMILES: CCC(=O)NC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1ccccc1
• InChI: InChI=1S/C20H24N6O4/c1-2-14(27)21-9-13-16(28)17(29)20(30-13)26-11-25-15-18(23-10-24-19(15)26)22-8-12-6-4-3-5-7-12/h3-7,10-11,13,16-17,20,28-29H,2,8-9H2,1H3,(H,21,27)(H,22,23,24)/t13-,16-,17-,20-/m1/s1
• InChIKey: UYZDNXCKHHYQPD-AEVYOOLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[(2R,3S,4R,5R)-5-[6-(benzylamino)-9H-purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl}propanamide
• IUPAC Traditional name: N-{[(2R,3S,4R,5R)-5-[6-(benzylamino)purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl}propanamide
• Synonyms: N^6-Benzyl-NECA; N6-BENZYL-5'-N-ETHYLCARBOXAMIDOADENOSINE

Database IDs

• PubChem SID: 162105895
• PubChem CID: 52944854

CALCULATED PROPERTIES

• Acid pKa: 12.466183
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.26248264
• LogD (pH = 7.4): 0.34652367
• Log P: 0.34771398
• Molar Refractivity: 109.0298 cm^3
• Polarizability: 41.96858 Å^3
• Polar Surface Area: 134.42 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 2-8°C

DETAILS

MP Biomedicals - 02193615

An A₃ Adenosine receptor agonist.

REFERENCES

• Gallo-Rodriquez, et al., J. Med. Chem. , 37 : 636, (1994).