(2S,4S,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-5-acetamido-6-hydroxy-2-(hydroxymethyl)-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 177704
• Molecular Formular: C31H52N2O23
• Molecular Mass: 820.74418
• Monoisotopic Mass: 820.29608593
• SMILES: [C@@H]1(C([C@@H](C[C@](O1)(O[C@H]1[C@H]([C@@H](O[C@H]([C@H]1O)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)C)O)O)O)CO)O)C(=O)O)O)NC(=O)C)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@](O[C@@H]2[C@H](O)[C@@H](O[C@H]([C@@H]2O)CO)O[C@@H]2[C@H](CO)OC([C@H]([C@H]2O[C@@H]2O[C@@H](C)[C@H]([C@@H]([C@@H]2O)O)O)NC(=O)C)O)(C[C@H](C1NC(=O)C)O)C(=O)O)O)O
• InChI: InChI=1S/C31H52N2O23/c1-8-17(41)20(44)21(45)28(50-8)54-25-16(33-10(3)38)27(47)51-14(7-36)23(25)53-29-22(46)26(19(43)13(6-35)52-29)56-31(30(48)49)4-11(39)15(32-9(2)37)24(55-31)18(42)12(40)5-34/h8,11-29,34-36,39-47H,4-7H2,1-3H3,(H,32,37)(H,33,38)(H,48,49)/t8-,11-,12+,13+,14+,15?,16+,17+,18+,19-,20+,21-,22+,23+,24+,25+,26-,27?,28-,29-,31-/m0/s1
• InChIKey: NIGUVXFURDGQKZ-LDJLBVKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-5-acetamido-6-hydroxy-2-(hydroxymethyl)-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,4S,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-5-acetamido-6-hydroxy-2-(hydroxymethyl)-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: Neu5Ac2-α-3Gal1-b-4[Fuc1-α-3]GlcNAc,O-(5-Acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic Acid)-2-α-3-O-(b-D-galactopyranosyl)-1-b-4-O-[(α-L-fucopyranosyl)-1-α-3]-2-acetamido-2-deoxy-D-glucopyranose]; 3'-Sialyl-Lewis X; SLex; SSEA 1; Sialyl Lex tri; Sialyl Lewis X

Database IDs

• CAS Number: 98603-84-0
• PubChem SID: 164233614
• PubChem CID: 71752163

CALCULATED PROPERTIES

• Acid pKa: 2.8378649
• H Acceptors: 23
• H Donor: 15
• LogD (pH = 5.5): -10.725376
• LogD (pH = 7.4): -11.608568
• Log P: -8.11757
• Molar Refractivity: 170.5789 cm^3
• Polarizability: 71.22683 Å^3
• Polar Surface Area: 402.87 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Store in freezer

DETAILS

Toronto Research Chemicals - S410000

Antigen which binds to endothelial adhesion molecule, E-selectin.

REFERENCES

• Fukushima, K., et al.: Cancer Research, 44, 5279 (1984)
• Zein, N., et al.: Science, 240, 1198 (1984)
• Phillips, M.L., et al.: Science, 250, 1130 (1984)
• Walz, G., et al.: P.N.A.S. U.S.A., 88, 6224 (1984)
• Walker, S., et al.: P.N.A.S. U.S.A., 89, 4608 (199