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

• ChemBase ID: 178012
• Molecular Formular: C21H37NO18S
• Molecular Mass: 623.57938
• Monoisotopic Mass: 623.17313435
• SMILES: [C@H]1(C([C@@H]([C@@H](O[C@H]1CO)O[C@H]1[C@@H]([C@@H]([C@@H](O[C@H]1CO)OC)NC(=O)C)O[C@H]1C([C@H]([C@@H]([C@@H](O1)C)O)O)O)O)S(=O)(=O)OO)O
• Canonical SMILES: OC[C@@H]1O[C@@H](OC)[C@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](CO)[C@@H](C([C@@H]1O)S(=O)(=O)OO)O)O[C@@H]1O[C@@H](C)[C@H]([C@@H](C1O)O)O)NC(=O)C
• InChI: InChI=1S/C21H37NO18S/c1-6-11(26)13(28)14(29)20(35-6)39-17-10(22-7(2)25)19(34-3)37-9(5-24)16(17)38-21-15(30)18(41(32,33)40-31)12(27)8(4-23)36-21/h6,8-21,23-24,26-31H,4-5H2,1-3H3,(H,22,25)/t6-,8+,9+,10+,11+,12-,13+,14?,15+,16+,17+,18?,19+,20-,21-/m0/s1
• InChIKey: RBJAOXLODCNHJU-RSINGVCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-5-acetamido-2-(hydroxymethyl)-6-methoxy-4-{[(2S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxane-4-sulfonoperoxoic acid
• IUPAC Traditional name: (2S,3S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-5-acetamido-2-(hydroxymethyl)-6-methoxy-4-{[(2S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxane-4-sulfonoperoxoic acid
• Synonyms: 3'-SO4-Gal1-b-4[FUC1-α-3]GlcNAc-b-O-Me, Methyl O-2-α-3-O-(3-sulfo-b-D-galactopyranosyl)-1-b-4-O-[(α-L-fucopyranosyl)-1-α-3]-2-αcetamido-2-deoxy-b-D-glucopyranoside]; 3'-Sulphated Lewis X, Methyl Glycoside

Database IDs

• PubChem SID: 164233922
• PubChem CID: 71752299

CALCULATED PROPERTIES

• Acid pKa: 6.8046975
• H Acceptors: 17
• H Donor: 9
• LogD (pH = 5.5): -5.079449
• LogD (pH = 7.4): -5.7449827
• Log P: -5.058524
• Molar Refractivity: 124.9268 cm^3
• Polarizability: 53.31967 Å^3
• Polar Surface Area: 289.69 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Amorphous solid

DETAILS

Toronto Research Chemicals - S699250

Recently shown to be a good ligand for E- and L-selectins, two calcium-dependent mammalian lectins associated with early steps in the inflammatory response and lymphocyte extravasation into peripheral lymph nodes which makes them good candidates for anti

REFERENCES

• Yuen, C.T., et al.: J. Biol. Chem., 269, 1595 (1994)
• Lubineau, A., et al.: Tetrahedron Letters, 35, 47, 8795 (1994)