(2S)-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}propanoic acid

• ChemBase ID: 178159
• Molecular Formular: C17H30N2O13
• Molecular Mass: 470.4257
• Monoisotopic Mass: 470.17478903
• 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)OC[C@@H](C(=O)O)N)CO)O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](OC[C@@H](C(=O)O)N)[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/C17H30N2O13/c1-5(22)19-9-14(32-17-13(26)12(25)10(23)7(2-20)31-17)11(24)8(3-21)30-16(9)29-4-6(18)15(27)28/h6-14,16-17,20-21,23-26H,2-4,18H2,1H3,(H,19,22)(H,27,28)/t6-,7+,8+,9+,10-,11-,12-,13+,14+,16-,17-/m0/s1
• InChIKey: XDMCWZFLLGVIID-ULCOMTOUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-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}propanoic acid
• IUPAC Traditional name: (2S)-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}propanoic acid
• Synonyms: Serinyl 2-Acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside; 3-(O-b-D-galactosyl)-N-acetyl-α-D-galactosaminyl-1-O-serine; O-[2-(Acetylamino)-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl]-L-serine; T Epitope, Serinyl

Database IDs

• CAS Number: 60280-57-1
• PubChem SID: 164234069
• PubChem CID: 5288346

CALCULATED PROPERTIES

• Acid pKa: 1.6599866
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): -7.7176642
• LogD (pH = 7.4): -7.7327743
• Log P: -7.7176423
• Molar Refractivity: 97.9689 cm^3
• Polarizability: 40.93824 Å^3
• Polar Surface Area: 250.72 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T020000

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

• Kim, J.M., and Roy, R.: Tetrahedron Lett., 38, 3487 (1997)
• Qiu, D., and Koganty, R.: Tetrahedron Lett., 38, 961 (1997)
• Toyokuni, T., and Singhal, A.K.: Chem. Soc. Rev., 231, (1995)