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

• ChemBase ID: 153408
• Molecular Formular: C17H18N6O6S
• Molecular Mass: 434.42642
• Monoisotopic Mass: 434.10085333
• SMILES: c1cc(ccc1CSc1c2c(nc(n1)N)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)[N+](=O)[O-]
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(N)nc2SCc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C17H18N6O6S/c18-17-20-14-11(19-7-22(14)16-13(26)12(25)10(5-24)29-16)15(21-17)30-6-8-1-3-9(4-2-8)23(27)28/h1-4,7,10,12-13,16,24-26H,5-6H2,(H2,18,20,21)/t10-,12-,13-,16-/m1/s1
• InChIKey: BRSNNJIJEZWSBU-XNIJJKJLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(2-amino-6-{[(4-nitrophenyl)methyl]sulfanyl}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(2-amino-6-{[(4-nitrophenyl)methyl]sulfanyl}purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2-Amino-6-[(4-nitrobenzyl)thio]-9-β-D-ribofuranosylpurine; NBTG; NBTGR; S-(4-Nitrobenzyl)-6-thioguanosine

Database IDs

• CAS Number: 13153-27-0
• MDL Number: MFCD00005737
• PubChem SID: 162247547
• PubChem CID: 96048

CALCULATED PROPERTIES

• Acid pKa: 12.4539585
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 0.775876
• LogD (pH = 7.4): 0.7767042
• Log P: 0.7767186
• Molar Refractivity: 107.887 cm^3
• Polarizability: 40.915432 Å^3
• Polar Surface Area: 185.36 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: yellow powder
• Melting Point: 203-205 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%
• Empirical Formula (Hill Notation): C17H18N6O6S

DETAILS

Sigma Aldrich - N5763

Biochem/physiol Actions
Potent adenosine uptake inhibitor