(2S,4S,6R)-5-acetamido-2-{[(2R,3R,4S,5S,6R)-2-{[(3R,4R,5S,6R)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4R,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-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: 177703
• 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](OC([C@H]1NC(=O)C)O)CO)O[C@@H]1OC([C@H]([C@@H]([C@@H]1O)O)O)C)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](NC(=O)C)C(O)O[C@H]([C@H]2O[C@@H]2OC(C)[C@H]([C@@H]([C@@H]2O)O)O)CO)(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)53-23-14(7-36)51-27(47)16(33-10(3)38)25(23)54-29-22(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: XBSNXOHQOTUENA-CCOPCFGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,6R)-5-acetamido-2-{[(2R,3R,4S,5S,6R)-2-{[(3R,4R,5S,6R)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4R,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-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-{[(2R,3R,4S,5S,6R)-2-{[(3R,4R,5S,6R)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4R,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-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-3[Fuc1-α-4]GlcNAc; Sialyl Lewis A, Sodium Salt

Database IDs

• CAS Number: 92448-22-1
• PubChem SID: 164233613
• PubChem CID: 71752162

CALCULATED PROPERTIES

• Acid pKa: 2.8704197
• H Acceptors: 23
• H Donor: 15
• LogD (pH = 5.5): -10.696659
• LogD (pH = 7.4): -11.605709
• 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: Water
• Apperance: White Amorphous Solid

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Storage Warning: Store in freezer

DETAILS

Toronto Research Chemicals - S397500

Antigen which supports E-, L-, and P-selectin-dependent adhesion.

REFERENCES

• Gallatin, W.M. et al.: Nature, 304, 30 (1983)
• Watson, S.R., et al.: Nature, 349, 164 (1983)
• Berg, E.L., et al.: Biochem. Biophys. Res. Comm., 184, 1048 (1983)
• Lubineau, A., et al.: J. Chem. Soc. Chem. Commun., 1419 (1983)
• Kameyama, A., et al.: J. Carb