(2S,3R)-2-amino-3-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}butanoic acid

• ChemBase ID: 178160
• Molecular Formular: C18H32N2O13
• Molecular Mass: 484.45228
• Monoisotopic Mass: 484.19043909
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)O[C@H]1[C@H]([C@@H](O[C@@H]([C@H]1NC(=O)C)O[C@@H]([C@H](N)C(=O)O)C)CO)O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](O[C@@H]([C@@H](C(=O)O)N)C)[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/C18H32N2O13/c1-5(9(19)16(28)29)30-17-10(20-6(2)23)15(12(25)8(4-22)31-17)33-18-14(27)13(26)11(24)7(3-21)32-18/h5,7-15,17-18,21-22,24-27H,3-4,19H2,1-2H3,(H,20,23)(H,28,29)/t5-,7-,8-,9+,10-,11+,12+,13+,14-,15-,17+,18+/m1/s1
• InChIKey: VWNOCGQJSBAAFO-RBMHVKAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-amino-3-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}butanoic acid
• IUPAC Traditional name: (2S,3R)-2-amino-3-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}butanoic acid
• Synonyms: O-[2-(Acetylamino)-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl]-L-threonine; Threonyl 2-Acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside; T Epitope, Threonyl

Database IDs

• CAS Number: 60280-58-2
• PubChem SID: 164234070
• PubChem CID: 11016372

CALCULATED PROPERTIES

• Acid pKa: 1.7261004
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): -7.3010807
• LogD (pH = 7.4): -7.31393
• Log P: -7.3010974
• Molar Refractivity: 102.3877 cm^3
• Polarizability: 42.7407 Å^3
• Polar Surface Area: 250.72 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: White Solid
• Melting Point: >170°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - T020020

A cancer associated carbohydrate tumor antigen which may be effective as cancer specific targets for immunotherapy as well as in the development of diagnostic monoclonal antibodies. Has been used or considered for use in human vaccines.

REFERENCES

• Gambert, U., et al.: Bioorg. Med. Chem., 5, 1285 (1997)
• Yi, W., et al.: Biochem., 47, 1241 (1997)