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

• ChemBase ID: 89466
• Molecular Formular: C16H28N2O11
• Molecular Mass: 424.40032
• Monoisotopic Mass: 424.16930973
• SMILES: CC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC(=O)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]1NC(=O)C)O)O)NC(=O)C
• InChI: InChI=1S/C16H28N2O11/c1-5(21)17-9-13(25)11(23)7(3-19)28-16(9)29-14-10(18-6(2)22)15(26)27-8(4-20)12(14)24/h7-16,19-20,23-26H,3-4H2,1-2H3,(H,17,21)(H,18,22)/t7-,8-,9-,10-,11-,12+,13-,14-,15?,16+/m1/s1
• InChIKey: FJGXDMQHNYEUHI-DKDAEFSNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5R,6R)-4-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; N-[(2R,3R,4R,5S,6R)-2-{[(3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5R,6R)-4-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; N-[(2R,3R,4R,5S,6R)-2-{[(3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: GlcNAc1-b-3GalNAc; 2-Acetamido-2-deoxy-3-O-(beta-D-2-acetamido-2-deoxyglucopyranosyl)-D-galactopyranose; 2-(Acetylamino)-3-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-2-deoxy-D-galactose; GlcNAc1β-3GalNAc; 2-Acetamido-2-deoxy-3-O-(β-D-2-acetamido-2-deoxyglucopyranosyl)-D-galactopyranose

Database IDs

• CAS Number: 95673-98-6
• MDL Number: MFCD02683230
• PubChem SID: 162076346
• PubChem CID: 10295910

CALCULATED PROPERTIES

• Acid pKa: 11.497845
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -5.2794456
• LogD (pH = 7.4): -5.2794785
• Log P: -5.279445
• Molar Refractivity: 90.5393 cm^3
• Polarizability: 37.461098 Å^3
• Polar Surface Area: 207.27 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 172-177°C (dec.); 183-188(dec.)°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A150750

Oligosaccharide widely distributed in the human digestive tract.

REFERENCES

• Uchimura, K., et al.: J. Biol. Chem., 277, 3979 (2001)
• Robbe, C., et al.: Biochem. J., 384, 307 (2001)
• Capon, C., et al.: Biochem. J., 358, 657 (2001)