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

• ChemBase ID: 172538
• Molecular Formular: C12H22O11
• Molecular Mass: 342.29648
• Monoisotopic Mass: 342.11621152
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)O[C@H]1[C@@H](C(OC(C1O)O)CO)O)O)O)O
• Canonical SMILES: OCC1OC(O)C([C@H]([C@@H]1O)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)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-PKGNJHJLSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 50692-75-6
• PubChem SID: 164228448
• PubChem CID: 70822988

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 - M166335

A disaccharide isolated from the tubers of Arum maculatum L.

REFERENCES

• Lipkind, G.M., et al.: Carbohydr. Res., 175, 59 (1988)