(2R,3R,4S,5S,6R)-2-{[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(4-isothiocyanatophenoxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 171985
• Molecular Formular: C19H25NO11S
• Molecular Mass: 475.4669
• Monoisotopic Mass: 475.11483163
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)O[C@H]1[C@@H]([C@@H](O[C@@H]([C@H]1O)Oc1ccc(cc1)N=C=S)CO)O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2ccc(cc2)N=C=S)[C@H]([C@H]([C@@H]1O)O[C@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C19H25NO11S/c21-5-10-12(23)14(25)15(26)18(29-10)31-17-13(24)11(6-22)30-19(16(17)27)28-9-3-1-8(2-4-9)20-7-32/h1-4,10-19,21-27H,5-6H2/t10-,11-,12-,13-,14+,15-,16-,17+,18-,19+/m1/s1
• InChIKey: DFMSOQFMHUTMRX-IDDMUUAKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-{[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(4-isothiocyanatophenoxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5S,6R)-2-{[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(4-isothiocyanatophenoxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 4-Isothiocyanatophenyl 3-O-α-D-Glucopyranosyl-α-D-glucopyranoside; 4-Isothiocyanatophenyl α-Nigeroside

Database IDs

• PubChem SID: 164227895
• PubChem CID: 71749639

CALCULATED PROPERTIES

• Acid pKa: 11.934278
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -1.3474004
• LogD (pH = 7.4): -1.3474107
• Log P: -1.347398
• Molar Refractivity: 109.6595 cm^3
• Polarizability: 44.05482 Å^3
• Polar Surface Area: 190.89 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I903700

4-Isothiocyanatophenyl α-Nigeroside is an analogue of the unfermentable sugar Nigerose.