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

• ChemBase ID: 172539
• Molecular Formular: C12H22O11
• Molecular Mass: 342.29648
• Monoisotopic Mass: 342.11621152
• SMILES: [C@@H]1([C@@H](C(C(OC1CO)O)O)O[C@@H]1OC([C@@H](C([C@@H]1O)O)O)CO)O
• Canonical SMILES: OCC1OC(O)C([C@H]([C@@H]1O)O[C@@H]1OC(CO)[C@@H](C([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-/m0/s1
• InChIKey: QIGJYVCQYDKYDW-LFSHVTFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5R)-6-(hydroxymethyl)-4-{[(2S,3S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,3,5-triol
• IUPAC Traditional name: (4S,5R)-6-(hydroxymethyl)-4-{[(2S,3S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,3,5-triol
• Synonyms: α-D-Man-[1-3]D-Man; 3-O-α-D-mannopyranosyl-D-mannose; 3α-Mannobiose; 3-O-α-D-Mannopyranosyl D-Mannopyranose; 3-O-α-D-Mannopyranosyl D-Mannose

Database IDs

• CAS Number: 23745-85-9
• PubChem SID: 164228449
• PubChem CID: 71749900

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

DETAILS

Toronto Research Chemicals - M166340

Believed to be the major antigenic determinant in the cell wall of yeast. An inhibitor of fibril lectins from enterobacteria.

REFERENCES

• Schutzbach, J. S., et al.: FEBS, 5, 145 (1969)
• Ballou, C.E., et al.: Science, 184, 127 (1969)
• Sharon, N., et al.: Pure Appl. Chem.: 55, 671 (1969)