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

• ChemBase ID: 70459
• Molecular Formular: C10H12ClN5O4
• Molecular Mass: 301.68638
• Monoisotopic Mass: 301.05778157
• SMILES: O1[C@H]([C@@H]([C@@H]([C@H]1CO)O)O)n1cnc2c1nc(nc2Cl)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([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-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(2-amino-6-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 6-Chloroguanineriboside; (-)-2-Amino-6-chloropurine riboside; 6-Chloroguanine riboside; 2-Amino-6-chloropurine riboside

Database IDs

• CAS Number: 2004-07-1
• EC Number: 217-905-3
• MDL Number: MFCD00005735
• PubChem SID: 162036175; 24890889
• PubChem CID: 102197

CALCULATED PROPERTIES

• Acid pKa: 12.453938
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.1824207
• 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

• Melting Point: 165-167 °C (dec.)(lit.)

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%; 95+%
• Empirical Formula (Hill Notation): C10H12ClN5O4

DETAILS

Sigma Aldrich - A4634

Application
2-Amino-6-chloropurine riboside is used in the biosynthesis of mutagenic and prodrug nucleosides such as 2′-deoxy-2-(p-nitrophenyl)-adenosine and 6-deoxyacyclovir and of 6-arylthio analogues.