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

• ChemBase ID: 131226
• Molecular Formular: C17H17N5O6S
• Molecular Mass: 419.41178
• Monoisotopic Mass: 419.08995429
• SMILES: c1cc(ccc1CSc1c2c(ncn1)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)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-/m1/s1
• InChIKey: DYCJFJRCWPVDHY-LSCFUAHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}-9H-purin-9-yl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(4-nitrophenyl)methyl]sulfanyl}purin-9-yl)oxolane-3,4-diol
• Synonyms: NBMPR; NBTI; S-(4-Nitrobenzyl)-6-thioinosine; 6-[(4-Nitrobenzyl)thio]-9-β-D-ribofuranosylpurine; 6-[(4-硝基苄基)硫代]-9-β-D-呋喃核糖基嘌呤; S-(4-硝基苄基)-6-硫肌苷

Database IDs

• CAS Number: 38048-32-7
• EC Number: 253-753-4
• MDL Number: MFCD00005745
• PubChem SID: 162225504; 24277723
• PubChem CID: 65407

CALCULATED PROPERTIES

• Acid pKa: 12.454004
• H Acceptors: 9
• 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

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: slightly soluble; 0.1 M NaOH: slightly soluble; DMSO: soluble; H2O: insoluble
• Apperance: white solid
• Melting Point: 187-190 °C(lit.)

Safety Information

• RTECS: UO9025000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), SLC29A1(2030)

Product Information

• Purity: ≥98%; 98%
• Empirical Formula (Hill Notation): C17H17N5O6S

DETAILS

Sigma Aldrich - N2255

Biochem/physiol Actions
Potent adenosine uptake inhibitor
Inhibitor of equilibrative nucleoside transporters (ENTs), particularly adenosine transporters, in central nervous system1 and vascular smooth muscle.2

Sigma Aldrich - N127

Biochem/physiol Actions
Inhibitor of equilibrative nucleoside transporters (ENTs), particularly adenosine transporters, in central nervous system1 and vascular smooth muscle.2

Sigma Aldrich - 861499

Application
A very potent inhibitor of nucleoside transport. NBMPR, in cultures, binds tightly but reversibly to tumor membrane sites associated with the nucleoside transport mechanism and is, therefore, a useful tool for cancer research.
Biochem/physiol Actions
Inhibitor of equilibrative nucleoside transporters (ENTs), particularly adenosine transporters, in central nervous system1 and vascular smooth muscle.2