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

• ChemBase ID: 159563
• Molecular Formular: C10H13N5O4
• Molecular Mass: 267.24132
• Monoisotopic Mass: 267.09675392
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(ncn2)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6?,7+,10-/m1/s1
• InChIKey: OIRDTQYFTABQOQ-HMEJCUHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 9-β-D-Ribofuranosyl-9H-purin-6-amine; 9-β-D-Ribofuranosyladenine; Adenine Riboside; Adenocard; Adenocor; Adenogesic; Adenoscan; Adrekar; Boniton; D-Adenosine; 1-(6-Amino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranose; Myocol; NSC 7652; Adenosine

Database IDs

• CAS Number: 58-61-7
• PubChem SID: 162253698
• PubChem CID: 53384930

CALCULATED PROPERTIES

• Acid pKa: 12.454003
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.2061174
• LogD (pH = 7.4): -2.09263
• Log P: -2.0909638
• Molar Refractivity: 63.1956 cm^3
• Polarizability: 24.545797 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 230-234°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A280400

Nucleotide.

REFERENCES

• Long, X., et al.: J. Pharmacol. Exper. Ther., 335, 781 (2010)
• Ham, M., et al.: J. Pharmacol. Exper. Ther., 335, 607 (2010)