(2S,4S,5R)-5-[6-(benzylamino)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide

• ChemBase ID: 161540
• Molecular Formular: C19H22N6O4
• Molecular Mass: 398.41578
• Monoisotopic Mass: 398.17025321
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(ncn2)NCc1ccccc1)C(=O)NCC)O)O
• Canonical SMILES: CCNC(=O)[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1ncnc2NCc1ccccc1
• InChI: InChI=1S/C19H22N6O4/c1-2-20-18(28)15-13(26)14(27)19(29-15)25-10-24-12-16(22-9-23-17(12)25)21-8-11-6-4-3-5-7-11/h3-7,9-10,13-15,19,26-27H,2,8H2,1H3,(H,20,28)(H,21,22,23)/t13?,14-,15-,19+/m0/s1
• InChIKey: VVHDYJFDZYHAMR-XODXHAEBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R)-5-[6-(benzylamino)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• IUPAC Traditional name: (2S,4S,5R)-5-[6-(benzylamino)purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• Synonyms: 1-Deoxy-N-ethyl-1-[6-[(phenylmethyl)amino]-9H-purin-9-yl]-β-D-ribofuranuronamide; N6-Benzyl-NECA; N6-Benzyl-5'-ethylcarboxamido Adenosine

Database IDs

• CAS Number: 152918-32-6
• PubChem SID: 162255675
• PubChem CID: 46783699

CALCULATED PROPERTIES

• Acid pKa: 12.393076
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.05615367
• LogD (pH = 7.4): 0.027839031
• Log P: 0.029029272
• Molar Refractivity: 104.6365 cm^3
• Polarizability: 40.135998 Å^3
• Polar Surface Area: 134.42 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 169-171°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B276550

A potent selective adenosine receptor agonist.

REFERENCES

• Gallo-Rodriquez, et al.: J. Med. Chem., 37, 636 (1994)
• Gao, Z., et al.: Biochem. Pharmacol., 65, 1675 (1994)
• Rodenko, B., et al.: Bioorg. Med. Chem., 14, 1618 (1994)