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

• ChemBase ID: 158847
• Molecular Formular: C22H38N2O16
• Molecular Mass: 586.54092
• Monoisotopic Mass: 586.22213315
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)OC[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)O)NC(=O)C)O[C@@H]1O[C@H]([C@@H]([C@@H]([C@@H]1O)O)O)CO)O)NC(=O)C)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](O[C@H]2[C@@H](O)[C@H](CO[C@@H]3O[C@@H](CO)[C@H]([C@@H]([C@@H]3NC(=O)C)O)O)O[C@@H]([C@H]2NC(=O)C)O)[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C22H38N2O16/c1-6(27)23-11-16(32)13(29)8(3-25)38-21(11)36-5-10-15(31)19(12(20(35)37-10)24-7(2)28)40-22-18(34)17(33)14(30)9(4-26)39-22/h8-22,25-26,29-35H,3-5H2,1-2H3,(H,23,27)(H,24,28)/t8-,9-,10-,11-,12-,13-,14+,15+,16-,17+,18-,19-,20+,21-,22+/m1/s1
• InChIKey: AULDNGHDBFNGGC-XYVIJKTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5S,6R)-2-{[(2R,3R,4R,5R,6S)-5-acetamido-3,6-dihydroxy-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5S,6R)-2-{[(2R,3R,4R,5R,6S)-5-acetamido-3,6-dihydroxy-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: O-2-(Acetylamino)-2-deoxy-β-D-glucopyranosyl-(1-6)-O-[β-D-galactopyranosyl-(1-3)]-2-(acetylamino)-2-deoxy-α-D-galactopyranose; Gal1β-3(GlcNAc1β-6)GalNAc; 2-Acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-O-(β-D-galactopyranosyl)-2-deoxy-α-D-galactopyranose

Database IDs

• CAS Number: 149793-99-7
• PubChem SID: 162252982
• PubChem CID: 52921656

CALCULATED PROPERTIES

• Acid pKa: 11.381226
• H Acceptors: 16
• H Donor: 11
• LogD (pH = 5.5): -7.0502815
• LogD (pH = 7.4): -7.0503244
• Log P: -7.050281
• Molar Refractivity: 122.9526 cm^3
• Polarizability: 51.273045 Å^3
• Polar Surface Area: 286.42 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A134300

New kind of carbohydrate array and its use for profiling antiglycan antibodies and discovery of novel human cellulose-binding antibodies.

REFERENCES

• Helenius, A., et al.: Science, 291, 2364 ( 2001), Bryan, M., et al.: Chem. Biol., 9, 713 (2002)
• Wang, D., et al.: Nat. Biotechnol., 20, 275 ( 2002),