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

• ChemBase ID: 89590
• Molecular Formular: C14H25NO11
• Molecular Mass: 383.3484
• Monoisotopic Mass: 383.14276063
• SMILES: O=C(N[C@@H]1[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](OC1O)CO)C
• 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-UITYFYQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5R,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: β-D-Gal-(1->3)-D-GalNAc; Galβ1-3GalNAc
• Synonyms: Gal1-b-3GalNAc; 2-Acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl)-D-galactopyranose; β-D-Galactosyl-(1-3)-N-acetylgalactosamine; Gal1-β-3GalNAc; O-β-D-Galactopyranosyl-(1-3)-N-acetylgalactosamine; 2-Acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-D-galactose; β-D-Gal-[1→3]-D-GalNAc; Galacto-N-biose; 2-ACETAMIDO-2-DEOXY-3-O-(β-D-GALACTOPYRANOSYL)-D-GALACTOPYRANOSE

Database IDs

• CAS Number: 20972-29-6; 3554-90-3
• MDL Number: MFCD00063995
• PubChem SID: 162076463
• PubChem CID: 441248

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: 159-160°C; 159-160°C

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C

Product Information

• Purity: ≥98%

DETAILS

MP Biomedicals - 02154180

β-D-Gal-[1→3]-D-GalNAc
Purity: ≥98% N-Acetylglucosaminyltransferase substrate1. Also used to study lectin inhibition2.

Apollo Scientific Ltd - OR5200T

Found inhydrolysates of blood group A,B,H,and Lewissubstances and forms an essential part of their antigenic determinants.

Toronto Research Chemicals - A152000

It is found in hydrolysates of blood group A,B,H, and the 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

• Williams, D., et al., J. Biol. Chem.
• Rege, V.P., et al.: Nature, 200, 532 (1963)
• Svennerholm, L.: J. Lipid Res., 5, 145 (1963)
• Gastaldi, D., et al.: J. Nephrol., 20, 689 (1963)
• Aoki, K., et al.: J. Biol. Chem., 283, 30385 (1963)
• Nakajima, M., et al.: App. Env. Microbiol., 74, 6333 (2008)