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

• ChemBase ID: 172537
• Molecular Formular: C12H22O11
• Molecular Mass: 342.29648
• Monoisotopic Mass: 342.11621152
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)OC1[C@H]([C@@H](C(OC1O)CO)O)O)O)O)O
• Canonical SMILES: OCC1OC(O)C([C@H]([C@@H]1O)O)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C12H22O11/c13-1-3-6(16)8(18)10(11(20)21-3)23-12-9(19)7(17)5(15)4(2-14)22-12/h3-20H,1-2H2/t3?,4?,5-,6-,7+,8+,9?,10?,11?,12+/m1/s1
• InChIKey: HIWPGCMGAMJNRG-KHDAGABXSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 50728-38-6
• PubChem SID: 164228447
• PubChem CID: 71749899

CALCULATED PROPERTIES

• Acid pKa: 11.267477
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.703376
• LogD (pH = 7.4): -4.7034335
• 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 - M166330

2-O-β-D-Mannopyranosyl-D-mannose is used in the preparation of oligo-mannosides used for diagnosing or preventing infection.

REFERENCES

• Suzuki, S., et al.: Curr. Topics Med. Mycology, 8, 57 (1997)
• Yuasa, H., et al.: Bioorg. Med. Chem. Lett., 8, 1297 (1997)