(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(4-nitrophenyl)methyl]sulfanyl}oxane-3,4,5-triol

• ChemBase ID: 175227
• Molecular Formular: C13H17NO7S
• Molecular Mass: 331.34158
• Monoisotopic Mass: 331.07257289
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)SCc1ccc(cc1)[N+](=O)[O-])O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](SCc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C13H17NO7S/c15-5-9-10(16)11(17)12(18)13(21-9)22-6-7-1-3-8(4-2-7)14(19)20/h1-4,9-13,15-18H,5-6H2/t9-,10-,11+,12-,13+/m1/s1
• InChIKey: PMQUMUZAQBRAKI-LBELIVKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(4-nitrophenyl)methyl]sulfanyl}oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(4-nitrophenyl)methyl]sulfanyl}oxane-3,4,5-triol
• Synonyms: (4-Nitrophenyl)methyl 1-Thio-β-D-glucopyranoside; p-Nitrobenzyl 1-Thio-β-D-glucopyranoside; 4-Nitrobenzyl 1-Thio-β-D-glucopyranoside

Database IDs

• CAS Number: 35785-17-2
• PubChem SID: 164231137
• PubChem CID: 71751058

CALCULATED PROPERTIES

• Molar Refractivity: 78.7813 cm^3
• Polarizability: 30.78555 Å^3
• Polar Surface Area: 135.97 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true
• Acid pKa: 12.480158
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.017742207
• LogD (pH = 7.4): -0.017745769
• Log P: -0.01774216

DETAILS

Toronto Research Chemicals - N495760

"Alkyl-glycoside" is considered to be a novel targeting vector for the kidney.

REFERENCES

• Haas, M., et al.: Kidney Int., et al.: 52, 1693 (1997)
• Basu, S., et al.: Biochem. Pharmacol., 40, 1941 (1997)
• Suzuki, K., et al.: J. Phamacol. Exp. Ther., 288, 888 (1997)