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

• ChemBase ID: 159159
• Molecular Formular: C19H22BrN2NaO9
• Molecular Mass: 525.27975
• Monoisotopic Mass: 524.04063658
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@](O1)(Oc1c[nH]c2c1cc(cc2)Br)C(=O)[O-])O)NC(=O)C)[C@@H]([C@@H](CO)O)O.[Na+]
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@@](C[C@H]([C@H]1NC(=O)C)O)(Oc1c[nH]c2c1cc(Br)cc2)C(=O)[O-])O)O.[Na+]
• InChI: InChI=1S/C19H23BrN2O9.Na/c1-8(24)22-15-12(25)5-19(18(28)29,31-17(15)16(27)13(26)7-23)30-14-6-21-11-3-2-9(20)4-10(11)14;/h2-4,6,12-13,15-17,21,23,25-27H,5,7H2,1H3,(H,22,24)(H,28,29);/q;+1/p-1/t12-,13+,15+,16+,17+,19+;/m0./s1
• InChIKey: LZFXHKUJKQJFEQ-RKNQWDLPSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,4S,5R,6R)-2-[(5-bromo-1H-indol-3-yl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,4S,5R,6R)-2-[(5-bromo-1H-indol-3-yl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: 5-Bromo-1H-indol-3-yl 5-(Acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic Acid Sodium Salt; N-Acetyl-2-O-(5-bromo-1H-indol-3-yl)-α-neuraminic Acid Sodium Salt

Database IDs

• PubChem SID: 162253294
• PubChem CID: 71312832

CALCULATED PROPERTIES

• Acid pKa: 2.648652
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -3.1318066
• LogD (pH = 7.4): -3.8664668
• Log P: -0.36227128
• Molar Refractivity: 117.5877 cm^3
• Polarizability: 43.628166 Å^3
• Polar Surface Area: 184.4 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A168800

A novel chromogenic substrate for the staining of sialidase activity.

REFERENCES

• Heppelmann, B., et al.: Acta Histochemica, 73, 41 (1983)