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

• ChemBase ID: 164402
• Molecular Formular: C11H13ClN4O5
• Molecular Mass: 316.69772
• Monoisotopic Mass: 316.05744722
• SMILES: n1c(nc2c(c1OC)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)Cl
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Cl)nc2OC
• InChI: InChI=1S/C11H13ClN4O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3/t4-,6-,7-,10-/m1/s1
• InChIKey: QFGKCCNEHWKCTD-KQYNXXCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(2-chloro-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(2-chloro-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2-Chloro-6-methoxy-9-β-D-ribofuranosyl-9H-purine; 2-Chloro-6-methoxypurine riboside; NSC 31144; 2-Chloro-6-O-methyl-inosine

Database IDs

• CAS Number: 15465-92-6
• PubChem SID: 162258537
• PubChem CID: 71314761

CALCULATED PROPERTIES

• Acid pKa: 12.454002
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.5111594
• LogD (pH = 7.4): -0.5111627
• Log P: -0.5111588
• Molar Refractivity: 70.457 cm^3
• Polarizability: 28.032957 Å^3
• Polar Surface Area: 122.75 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C369205

adenosine analogue.

REFERENCES

• Long, M., et al.: Biochem. Pharmacol., 71, 1671 (2006)