disodium [(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl sulfate

• ChemBase ID: 159339
• Molecular Formular: C14H23NNa2O17S2
• Molecular Mass: 587.43846
• Monoisotopic Mass: 587.02027884
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COS(=O)(=O)[O-])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+].[Na+]
• Canonical SMILES: CC(=O)N[C@@H]1C(O)O[C@H]([C@H]([C@@H]1O)O[C@@H]1O[C@@H](COS(=O)(=O)[O-])[C@@H]([C@@H]([C@@H]1O)O)O)COS(=O)(=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C14H25NO17S2.2Na/c1-4(16)15-7-9(18)12(6(30-13(7)21)3-29-34(25,26)27)32-14-11(20)10(19)8(17)5(31-14)2-28-33(22,23)24;;/h5-14,17-21H,2-3H2,1H3,(H,15,16)(H,22,23,24)(H,25,26,27);;/q;2*+1/p-2/t5-,6-,7-,8+,9-,10+,11-,12-,13?,14+;;/m1../s1
• InChIKey: WNRBKGCBRFNJMG-DSLMWRJXSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl sulfate
• IUPAC Traditional name: disodium [(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl sulfate
• Synonyms: 2-(Acetylamino)-2-deoxy-4-O-(6-O-sulfo-β-D-galactopyranosyl)-D-glucose 6-(Hydrogen Sulfate) Disodium Salt; Gal(6S)β-(1-4)-GlcNAc(6S); N-Acetyllactosamine 6,6'-Disulfate Disodium SaltDISCONTINUED

Database IDs

• CAS Number: 321897-68-1
• PubChem SID: 162253474
• PubChem CID: 71312946

CALCULATED PROPERTIES

• Acid pKa: -2.291736
• H Acceptors: 15
• H Donor: 6
• LogD (pH = 5.5): -9.63423
• LogD (pH = 7.4): -9.63428
• Log P: -8.57151
• Molar Refractivity: 97.1782 cm^3
• Polarizability: 42.988976 Å^3
• Polar Surface Area: 290.8 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A184990

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