N-[(3R,4R,5S,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: 89674
• 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-RPHKZZMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,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: lacto-N-biose
• Synonyms: Glucopyranose Gal1-b-3-GlcNAc; 2-Acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl)-D-glucopyranose; O-β-D-Galactopyranosyl-(1-3)-N-acetylglucosamine; Gal1-β-3GlcNAc; Lacto-N-biose 1; Lewis C; 2-Acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-D-glucopyranose

Database IDs

• CAS Number: 50787-09-2
• MDL Number: MFCD00036714
• PubChem SID: 162076537
• PubChem CID: 440994

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: 165-167°C; 165-167°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Irritant/Store at -20°C

DETAILS

Toronto Research Chemicals - A152580

Acceptor for the α1,2-fucosyltransferase enzyme from Helicobacter pylori.

REFERENCES

• Fan, Y., et al.: J. Biol. Chem., 283, 16455 (2008)
• Nakajima, M., et al.: Appl. Environ. Microbiol., 74, 6333 (2008)
• Nakajima, M., et al.: App. Microbiol. Biotechnol., 83, 109 (2008)
• Ajisaka, K., et al.: J. Agric. Food Chem., 57, 3102 (2008)