(2R,3S,5R)-2-[6-amino-2-(phenylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 176518
• Molecular Formular: C16H18N6O4
• Molecular Mass: 358.35192
• Monoisotopic Mass: 358.13895309
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)Nc1ccccc1)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1nc(Nc1ccccc1)nc2N
• InChI: InChI=1S/C16H18N6O4/c17-13-10-14(21-16(20-13)19-8-4-2-1-3-5-8)22(7-18-10)15-12(25)11(24)9(6-23)26-15/h1-5,7,9,11-12,15,23-25H,6H2,(H3,17,19,20,21)/t9-,11?,12+,15-/m1/s1
• InChIKey: SCNILGOVBBRMBK-BWIWHEPQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-[6-amino-2-(phenylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-[6-amino-2-(phenylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2-Anilinoadenosine; CV 1808; LSU 165; 2-Phenylamino Adenosine

Database IDs

• CAS Number: 53296-10-9
• PubChem SID: 164232428
• PubChem CID: 45040225

CALCULATED PROPERTIES

• Acid pKa: 12.420938
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 0.02769043
• LogD (pH = 7.4): 0.027743075
• Log P: 0.027747925
• Molar Refractivity: 91.6278 cm^3
• Polarizability: 35.182934 Å^3
• Polar Surface Area: 151.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 236-238°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P319530

A selective A2-adenosine receptor agonist. Coronary vasodilator, antihypertensive and antipsychotic following systemic administration in vivo.

REFERENCES

• Martin, et al.: Pharmacol. Biochem. Behav., 45, 951 (1993