[(2R,3R,4S,5R,6R)-3,4-dihydroxy-6-(4-nitrophenoxy)-5-{[(2S,3S,4R,5R,6S)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl benzoate

• ChemBase ID: 175322
• Molecular Formular: C31H35NO16
• Molecular Mass: 677.6067
• Monoisotopic Mass: 677.19558405
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1COC(=O)c1ccccc1)Oc1ccc(cc1)[N+](=O)[O-])O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C)OC(=O)C)OC(=O)C)OC(=O)C)O)O
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](O[C@@H]2[C@H](O[C@H]([C@@H]([C@@H]2O)O)COC(=O)c2ccccc2)Oc2ccc(cc2)[N+](=O)[O-])O[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)C
• InChI: InChI=1S/C31H35NO16/c1-15-25(43-16(2)33)27(44-17(3)34)28(45-18(4)35)31(42-15)48-26-24(37)23(36)22(14-41-29(38)19-8-6-5-7-9-19)47-30(26)46-21-12-10-20(11-13-21)32(39)40/h5-13,15,22-28,30-31,36-37H,14H2,1-4H3/t15-,22+,23-,24-,25+,26+,27+,28-,30-,31-/m0/s1
• InChIKey: XCTRVDVYYTYELV-HQVAYZEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6R)-3,4-dihydroxy-6-(4-nitrophenoxy)-5-{[(2S,3S,4R,5R,6S)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl benzoate
• IUPAC Traditional name: [(2R,3R,4S,5R,6R)-3,4-dihydroxy-6-(4-nitrophenoxy)-5-{[(2S,3S,4R,5R,6S)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl benzoate
• Synonyms: p-Nitrophenyl 6-O-Benzoyl-2-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-α-D-galactopyranoside

Database IDs

• PubChem SID: 164231232
• PubChem CID: 71751089

CALCULATED PROPERTIES

• Acid pKa: 12.710618
• H Acceptors: 12
• H Donor: 2
• LogD (pH = 5.5): 2.436347
• LogD (pH = 7.4): 2.4363449
• Log P: 2.436347
• Molar Refractivity: 155.6541 cm^3
• Polarizability: 62.762806 Å^3
• Polar Surface Area: 228.4 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - N503040

A Nitrophenyl derivative of 2-O-(a-L-Fucopyranosyl)-a-D-galactopyranoside (Disaccharide H), a biologically important oligosaccharide component of glycoconjugates that play a role in cellular recognition and intercellular interactions.

REFERENCES

• Carbohyd. Res., 4, 189 (1967)
• Can. J. Chem., 59, 314 (1967)
• J. Carbohydrate Chem., 11(1967)
• 397 (1992)