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

• ChemBase ID: 159939
• Molecular Formular: C10H12ClN5O4
• Molecular Mass: 301.68638
• Monoisotopic Mass: 301.05778157
• SMILES: n1c(nc2c(c1Cl)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O)N
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1nc(N)nc2Cl
• InChI: InChI=1S/C10H12ClN5O4/c11-7-4-8(15-10(12)14-7)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5+,6?,9-/m1/s1
• InChIKey: TXWHPSZYRUHEGT-ACJOCUEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-(2-amino-6-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 6-Chloro-9-β-D-ribofuranosyl-9H-purin-2-amine; 2-Amino-6-chloropurine Ribonucleoside; 2-Amino-6-chloropurine Riboside; 6-Chloroguanosine; NSC 44586; 2-Amino-6-chloropurine-9-β-D-riboside

Database IDs

• CAS Number: 2004-07-1
• PubChem SID: 162254074
• PubChem CID: 45358303

CALCULATED PROPERTIES

• Acid pKa: 12.453938
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.1824194
• LogD (pH = 7.4): -1.1824174
• Log P: -1.1824136
• Molar Refractivity: 68.6942 cm^3
• Polarizability: 26.59567 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Colourless Crystalline Solid
• Melting Point: 148-151°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A603510

6-Substituted purines; a novel class of inhibitors of endogenous protein degradation.

REFERENCES

• Gordon, P.B., et al.: Arch. Biochem. Biophys., 217, 282 (1982)