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

• ChemBase ID: 128600
• Molecular Formular: C12H22O11
• Molecular Mass: 342.29648
• Monoisotopic Mass: 342.11621152
• SMILES: O([C@H]1[C@H](O)[C@H](OC(O)[C@@H]1O)CO)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO
• Canonical SMILES: OC[C@H]1OC(O)[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/C12H22O11/c13-1-3-5(15)7(17)8(18)12(22-3)23-10-6(16)4(2-14)21-11(20)9(10)19/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8-,9-,10+,11?,12-/m1/s1
• InChIKey: QIGJYVCQYDKYDW-NSYYTRPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}oxane-3,4,5-triol; (3R,4S,5R,6R)-6-(hydroxymethyl)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,3,5-triol
• IUPAC Traditional name: nigerose; (3R,4S,5R,6R)-6-(hydroxymethyl)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,3,5-triol
• Synonyms: 3-O-α-D-Glucopyranosyl-D-glucose; Sakebiose; Nigerose; 3-O-α-D-glucopyranosyl-D-glucose; Nigerose

Database IDs

• CAS Number: 497-48-3
• MDL Number: MFCD00057489
• PubChem SID: 162222907
• PubChem CID: 439512
• Chemspider ID: 388607
• MeSH Name: Nigerose
• Wikipedia Title: Nigerose

CALCULATED PROPERTIES

• Acid pKa: 11.253927
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.703376
• LogD (pH = 7.4): -4.7034354
• Log P: -4.703375
• Molar Refractivity: 68.3367 cm^3
• Polarizability: 28.969793 Å^3
• Polar Surface Area: 189.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95.0% (HPLC)
• Empirical Formula (Hill Notation): C12H22O11

DETAILS

Sigma Aldrich - 08602

Application
Nigerose (Sakebiose), an α(1,3) linked glucose disaccaharide, is used as a substrate to identify, differentiate and quantify enzymes such as nigerose phosphorylase(s) and α-glucosidase(s).