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

• ChemBase ID: 172136
• Molecular Formular: C15H17N5O5
• Molecular Mass: 347.32598
• Monoisotopic Mass: 347.12296867
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(ncn2)NCc1ccco1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1ncnc2NCc1ccco1
• InChI: InChI=1S/C15H17N5O5/c21-5-9-11(22)12(23)15(25-9)20-7-19-10-13(17-6-18-14(10)20)16-4-8-2-1-3-24-8/h1-3,6-7,9,11-12,15,21-23H,4-5H2,(H,16,17,18)/t9-,11?,12+,15-/m1/s1
• InChIKey: CAGLGYNQQSIUGX-BWIWHEPQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-{6-[(furan-2-ylmethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-{6-[(furan-2-ylmethyl)amino]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: NSC 120958; Kinetin Riboside; 6-Furfurylaminopurine Riboside, N6-Furfuryladenosine; N-(2-Furanylmethyl)adenosine

Database IDs

• CAS Number: 4338-47-0
• PubChem SID: 164228046
• PubChem CID: 71267820

CALCULATED PROPERTIES

• Acid pKa: 12.453007
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.0875263
• LogD (pH = 7.4): -1.005696
• Log P: -1.0045401
• Molar Refractivity: 85.6925 cm^3
• Polarizability: 32.82601 Å^3
• Polar Surface Area: 138.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 152-154°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - K570050

Used as an anticancer and antiviral agent.

REFERENCES

• Cancer Res., 20, 1362 (1960)
• Virology, 38, 26 (1960)