methyl (2S,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

• ChemBase ID: 162797
• Molecular Formular: C20H24BrClN2O9
• Molecular Mass: 551.76956
• Monoisotopic Mass: 550.03537004
• SMILES: c12c(ccc(c1Cl)Br)[nH]cc2O[C@@]1(C[C@H]([C@H]([C@@H](O1)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)OC
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@@](C[C@H]([C@H]1NC(=O)C)O)(Oc1c[nH]c2c1c(Cl)c(cc2)Br)C(=O)OC)O)O
• InChI: InChI=1S/C20H24BrClN2O9/c1-8(26)24-16-11(27)5-20(19(30)31-2,33-18(16)17(29)12(28)7-25)32-13-6-23-10-4-3-9(21)15(22)14(10)13/h3-4,6,11-12,16-18,23,25,27-29H,5,7H2,1-2H3,(H,24,26)/t11-,12+,16+,17+,18+,20+/m0/s1
• InChIKey: VATTYSQGTFSYRU-PSTHAIFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: 5-Bromo-4-chloro-3-indolyl-α-D-N-acetylneuraminic Acid, Methyl Ester

Database IDs

• PubChem SID: 162256932
• PubChem CID: 71307250

CALCULATED PROPERTIES

• Acid pKa: 12.056363
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 0.38766676
• LogD (pH = 7.4): 0.3876588
• Log P: 0.38766745
• Molar Refractivity: 116.3245 cm^3
• Polarizability: 47.78461 Å^3
• Polar Surface Area: 170.57 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 146-148°C

DETAILS

Toronto Research Chemicals - B682285

Used as a substrate for the detection of sialidase-like enzyme in screening of enzymes, studying physiological activities of gangliosides, and recombinant technologies.

REFERENCES

• Biorg. Med. Chem., 1, 147 (1993)