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

• ChemBase ID: 158886
• Molecular Formular: C14H25NO11
• Molecular Mass: 383.3484
• Monoisotopic Mass: 383.14276063
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)O[C@H]1[C@H]([C@@H](OC([C@H]1NC(=O)C)O)CO)O)O)O)O
• 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)NC(=O)C
• InChI: InChI=1S/C14H25NO11/c1-4(18)15-7-12(9(20)6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9+,10+,11-,12-,13?,14-/m1/s1
• InChIKey: HMQPEDMEOBLSQB-HJZACBRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5R,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: Gal-α1,3-GalNAc
• Synonyms: Gal1-α-3GalNAc; 2-Acetamido-2-deoxy-3-O-(α-D-galactopyranosyl)-D-galactose

Database IDs

• CAS Number: 60283-31-0
• PubChem SID: 162253021
• PubChem CID: 49852395

CALCULATED PROPERTIES

• Acid pKa: 11.494147
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.9914103
• LogD (pH = 7.4): -4.991444
• Log P: -4.9914103
• Molar Refractivity: 79.438 cm^3
• Polarizability: 33.212086 Å^3
• Polar Surface Area: 198.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 152-155°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A151995

It is found in hydrolysates of blood group A,B,H, and Le substances and forms an essential part of their antigenic determinants. It is also inherent in the structure of the brain gangliosides in which it constitutes the terminal part of the molecule.

REFERENCES

• Rege, V.P., et al.: Nature, 200, 532 (1963)
• Svennerholm, L.: J. Lipid Res., 5, 145 (1963)
• Morelle, W., et al.: Biochem. J., 330, 469 (1963)