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

• ChemBase ID: 158881
• Molecular Formular: C14H25NO10
• Molecular Mass: 367.349
• Monoisotopic Mass: 367.14784601
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1CO[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C)O)O)O)O)NC(=O)C)O)O
• Canonical SMILES: CC(=O)N[C@@H]1C(O)O[C@H]([C@H]([C@@H]1O)O)CO[C@@H]1O[C@@H](C)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C14H25NO10/c1-4-8(17)11(20)12(21)14(24-4)23-3-6-9(18)10(19)7(13(22)25-6)15-5(2)16/h4,6-14,17-22H,3H2,1-2H3,(H,15,16)/t4-,6+,7+,8+,9+,10+,11+,12-,13?,14+/m0/s1
• InChIKey: BSNVYGSAFLBSSQ-PKAYUKAWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 33639-80-4
• PubChem SID: 162253016
• PubChem CID: 71297234

CALCULATED PROPERTIES

• Acid pKa: 11.463857
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -3.9445007
• LogD (pH = 7.4): -3.9445364
• 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: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 135-139°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A151570

Oligosaccharide which participates in cell adhesion between bacterial and eukaryotic cells

REFERENCES

• Perret, S., et al.: Biochem. J., 389, 325 (2005)
• Tielker, D., et al.: Microbiol., 151, 1313 (2005)
• Marotte, K., et al.: ChemMedChem, 2, 1328 (2005)