(2S,3R,4S,5S)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}-9H-purin-9-yl)oxolane-3,4-diol

• ChemBase ID: 175202
• Molecular Formular: C17H17N5O6S
• Molecular Mass: 419.41178
• Monoisotopic Mass: 419.08995429
• SMILES: n1cnc2c(c1SCc1ccc(cc1)[N+](=O)[O-])ncn2[C@@H]1[C@H]([C@H]([C@@H](O1)CO)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H]([C@H]([C@H]1O)O)n1cnc2c1ncnc2SCc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C17H17N5O6S/c23-5-11-13(24)14(25)17(28-11)21-8-20-12-15(21)18-7-19-16(12)29-6-9-1-3-10(4-2-9)22(26)27/h1-4,7-8,11,13-14,17,23-25H,5-6H2/t11-,13-,14-,17-/m0/s1
• InChIKey: DYCJFJRCWPVDHY-MJFSBKNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}-9H-purin-9-yl)oxolane-3,4-diol
• IUPAC Traditional name: (2S,3R,4S,5S)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}purin-9-yl)oxolane-3,4-diol
• Synonyms: 6-S-[(4-Nitrophenyl)methyl]-6-thioinosine; 6-[(4-Nitrobenzyl)thio]-9-β-D-ribofuranosylpurine; S-(p-Nitrobenzyl)-6-mercapto-9-β-D-ribofuranosylpurine; NBMPR; NSC 296962; S-(4-Nitrobenzyl)-6-thioinosine

Database IDs

• CAS Number: 38048-32-7
• PubChem SID: 164231112
• PubChem CID: 38988593

CALCULATED PROPERTIES

• H Donor: 3
• LogD (pH = 5.5): 0.8909769
• LogD (pH = 7.4): 0.9263837
• Log P: 0.92685854
• Molar Refractivity: 103.2406 cm^3
• Polarizability: 39.756 Å^3
• Polar Surface Area: 159.34 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true
• Acid pKa: 12.454004
• H Acceptors: 9

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate
• Apperance: Off-White Solid
• Melting Point: 177-180°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - N493695

It is a prototype inhibitor of the human equilibrative nucleoside transporter (hENT1), and is a high affinity ligand with a Kd of 0.1-1.0 nM. Nucleoside transporter inhibitors have potential therapeutic applications as anticancer, antiviral, cardioprotect

REFERENCES

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• Zhu, Z., et al.: J. Med. Chem., 46, 831 (1989)
• Baldwin, S., et al.: J. Biol. Chem., 280, 15880 (1989)
• Barnes, K., et al.: Circ. Res., 99, 510 (2006