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

• ChemBase ID: 168462
• Molecular Formular: C12H16N6O4
• Molecular Mass: 308.29324
• Monoisotopic Mass: 308.12330302
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(ncn2)N)C(=O)NCC)O)O
• Canonical SMILES: CCNC(=O)[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C12H16N6O4/c1-2-14-11(21)8-6(19)7(20)12(22-8)18-4-17-5-9(13)15-3-16-10(5)18/h3-4,6-8,12,19-20H,2H2,1H3,(H,14,21)(H2,13,15,16)/t6?,7-,8-,12+/m0/s1
• InChIKey: JADDQZYHOWSFJD-ADEBKYASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R)-5-(6-amino-9H-purin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• IUPAC Traditional name: (2S,4S,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• Synonyms: NECA; 1-(6-Amino-9H-purin-9-yl)-1-deoxy-N-ethyl-β-D-ribofuranuronamide; 5'-Ethylcarboxamido Adenosine

Database IDs

• CAS Number: 35920-39-9
• PubChem SID: 162262594
• PubChem CID: 44338050

CALCULATED PROPERTIES

• Acid pKa: 12.393688
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.1122777
• LogD (pH = 7.4): -1.9988141
• Log P: -1.9971479
• Molar Refractivity: 74.5305 cm^3
• Polarizability: 28.813255 Å^3
• Polar Surface Area: 148.41 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 229-231°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E900980

A potent adenosine receptor agonist. Inhibits platelet aggregation and is centrally active in vivo.

REFERENCES

• Cusack and Hourani: Br. J. Pharmacol., 72, 433 (1981)
• Knapp, et al.: Pharmacol. Biochem. Behav., 68, 797 (2001)