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

• ChemBase ID: 169546
• 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(C(OC1CO)O)O)O)O)O)O
• Canonical SMILES: OCC1OC(O)C([C@H]([C@H]1O[C@H]1OC(CO)[C@@H]([C@@H](C1O)O)O)O)O
• InChI: InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3?,4?,5-,6-,7+,8?,9?,10-,11?,12+/m0/s1
• InChIKey: GUBGYTABKSRVRQ-SMFCXPKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,6R)-2-(hydroxymethyl)-6-{[(3R,4R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
• IUPAC Traditional name: (3R,4S,6R)-2-(hydroxymethyl)-6-{[(3R,4R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
• Synonyms: Gal1-α-4Gal; 4-O-(α-D-Galactopyranosyl)-D-galactose

Database IDs

• CAS Number: 13117-26-5
• PubChem SID: 162263678
• PubChem CID: 71317028

CALCULATED PROPERTIES

• Acid pKa: 11.2543745
• 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

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 77-80°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - G154755

Defines the P blood-group system and it functions as specific ligands towards receptors of uropathogenic E. coli and the Shigella dysenteriae toxin.

REFERENCES

• Race, R.R., et al.: Bood Groups in Man, 6th Edn., Blackwell, Osford, 1975, Kallenius G., et al.: FEMS Lett., 7, 297 (1983)