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

• ChemBase ID: 172290
• Molecular Formular: C20H35NO15
• Molecular Mass: 529.4896
• Monoisotopic Mass: 529.20066943
• SMILES: [C@H]1(C(O[C@H]([C@H]([C@H]1O)O)O[C@H]1[C@@H]([C@@H](C(O[C@H]1CO)O)NC(=O)C)O[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)CO)O)O)O)C)O
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1O[C@@H]1OC(C)[C@H]([C@@H]([C@@H]1O)O)O)O[C@@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O)NC(=O)C
• InChI: InChI=1S/C20H35NO15/c1-5-10(25)12(27)14(29)19(32-5)35-16-8(4-23)33-18(31)9(21-6(2)24)17(16)36-20-15(30)13(28)11(26)7(3-22)34-20/h5,7-20,22-23,25-31H,3-4H2,1-2H3,(H,21,24)/t5?,7-,8-,9-,10-,11+,12-,13+,14+,15-,16-,17-,18?,19+,20+/m1/s1
• InChIKey: CFDVGUXRLQWLJX-LUWXMQACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-2-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5S,6R)-2-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
• Synonyms: 2-Acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-3-O-(b-D-galactopyranosyl)-D-glucopyranose, Gal1-b-3[Fuc1-α-4]GlcNAc; Lewis A Trisaccharide

Database IDs

• CAS Number: 56570-03-7
• PubChem SID: 164228200
• PubChem CID: 71749780

CALCULATED PROPERTIES

• Acid pKa: 11.431733
• H Acceptors: 15
• H Donor: 10
• LogD (pH = 5.5): -5.7153363
• LogD (pH = 7.4): -5.7153754
• Log P: -5.715336
• Molar Refractivity: 110.3076 cm^3
• Polarizability: 46.311768 Å^3
• Polar Surface Area: 257.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: White Solid
• Melting Point: 160-162°C

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Dabelsteen, E., et al.: Cancer Research, 48, 181 (1988)
• Lasky, L.A.: Science, 258, 964 (1988)
• Mulligan, M.S., et al.: Nature, 364, 149 (1988)
• Mulligan, M.S., et al.: J. Exp. Med., 178, 623 (1988)
• Travis, J.: Science, 260, 906 (1993)