sodium [(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl sulfate

• ChemBase ID: 159341
• Molecular Formular: C14H24NNaO14S
• Molecular Mass: 485.39343
• Monoisotopic Mass: 485.08151973
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)O[C@H]1[C@@H]([C@@H](C(O[C@H]1COS(=O)(=O)[O-])O)NC(=O)C)O)O)O)O.[Na+]
• Canonical SMILES: OC[C@@H]1O[C@@H](O[C@@H]2[C@H](COS(=O)(=O)[O-])OC([C@H]([C@H]2O)NC(=O)C)O)[C@H]([C@H]([C@H]1O)O)O.[Na+]
• InChI: InChI=1S/C14H25NO14S.Na/c1-4(17)15-7-9(19)12(6(27-13(7)22)3-26-30(23,24)25)29-14-11(21)10(20)8(18)5(2-16)28-14;/h5-14,16,18-22H,2-3H2,1H3,(H,15,17)(H,23,24,25);/q;+1/p-1/t5-,6-,7-,8+,9-,10+,11-,12-,13?,14+;/m1./s1
• InChIKey: HYBYWGBGWQCPKW-UYYNWBDWSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium [(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl sulfate
• IUPAC Traditional name: sodium [(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl sulfate
• Synonyms: 2-(Acetylamino)-2-deoxy-4-O-β-D-galactopyranosyl-D-glucose 6-(Hydrogen Sulfate) Monosodium Salt; Galβ-(1-4)-GlcNAc(6S); N-Acetyllactosamine 6-Sulfate Sodium Salt, 90%

Database IDs

• CAS Number: 145447-78-5
• PubChem SID: 162253476
• PubChem CID: 71312947

CALCULATED PROPERTIES

• Acid pKa: -1.9700028
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -7.31282
• LogD (pH = 7.4): -7.3128624
• Log P: -6.767327
• Molar Refractivity: 88.3081 cm^3
• Polarizability: 38.09045 Å^3
• Polar Surface Area: 244.6 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 181-182°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A185010

N-Acetyllactosamine derivatives were tested as acceptors for α1,3-L-Fucosyltransferase present in human ovarian cancer sera and ovarian tumor.

REFERENCES

• Lasky, L., et al.: Science, 258, 964 (1992)
• Hemmerich, S., et al.: Biochemistry, 33, 4830 (1992)
• Clarke, J., et al.: J. Biol. Chem., 271, 10317 (1992)
• Komba, S., et al.: Bioorg. Med. Chem., 4, 1833 (1992)
• Yoshino, K., et al.: J. Med. Chem., 40, 455 (1