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

• ChemBase ID: 89518
• Molecular Formular: C14H25NO10
• Molecular Mass: 367.349
• Monoisotopic Mass: 367.14784601
• SMILES: C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(=O)C)C(O)O[C@@H]2CO)[C@@H](O)[C@H](O)[C@@H]1O
• Canonical SMILES: OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@H]([C@H]([C@@H]1O)O)O)O)NC(=O)C
• InChI: InChI=1S/C14H25NO10/c1-4-8(18)10(20)11(21)14(23-4)25-12-6(3-16)24-13(22)7(9(12)19)15-5(2)17/h4,6-14,16,18-22H,3H2,1-2H3,(H,15,17)/t4-,6+,7+,8+,9+,10+,11-,12+,13?,14-/m0/s1
• InChIKey: YSVYPLBRZMVZJE-SFHUXEFOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
• Synonyms: Fuc1-a-4GlcNAc; 2-Acetamido-2-deoxy-4-O-(alpha-L-fucopyranosyl)-D-glucopyranose; 2-(Acetylamino)-2-deoxy-4-O-(6-deoxy-α-L-galactopyranosyl)-D-glucose; Fuc1-α-4GlcNAc; 2-Acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-D-glucopyranose

Database IDs

• CAS Number: 76211-71-7
• MDL Number: MFCD00153897
• PubChem SID: 162076398
• PubChem CID: 71299548

CALCULATED PROPERTIES

• Acid pKa: 11.517157
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -3.9445007
• LogD (pH = 7.4): -3.9445326
• Log P: -3.9445002
• Molar Refractivity: 77.8943 cm^3
• Polarizability: 32.49977 Å^3
• Polar Surface Area: 178.17 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Orange Solid
• Melting Point: 216-218°C; 216-218°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A151550

Oligosaccharide which participates in cell adhesion between bacterial and eukaryotic cells

REFERENCES

• Perret, S., et al.: Biochem. J., 389, 325 (2005)
• Marotte, K., et al.: ChemMedChem., 2, 1328 (2005)