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

• ChemBase ID: 172293
• Molecular Formular: C20H35NO15
• Molecular Mass: 529.4896
• Monoisotopic Mass: 529.20066943
• SMILES: OC1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)CO)O)O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C)O)O)O)NC(=O)C
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O)O[C@@H]1O[C@@H](C)[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)36-17-9(21-6(2)24)18(31)33-8(4-23)16(17)35-20-15(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-/m0/s1
• InChIKey: HBBOZFUQJDYASD-QGTNPELVSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 71208-06-5
• PubChem SID: 164228203
• PubChem CID: 11813424

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

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 155-156°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L395000

Lewis X and related compounds bind to the selectins and act as anti-inflammatory agents.

REFERENCES

• Lasky, L.A.: Science, 258, 964 (1992)
• Mulligan, M.S., et al.: Nature, 364, 149 (1992)
• Mulligan, M.S., et al.: J. Exp. Med., 178, 623 (1992)
• Travis, J.: Science, 260, 906 (1993)