sodium (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: 162798
• Molecular Formular: C19H21BrClN2NaO9
• Molecular Mass: 559.72481
• Monoisotopic Mass: 558.00166422
• 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)[O-].[Na+]
• 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)[O-])O)O.[Na+]
• InChI: InChI=1S/C19H22BrClN2O9.Na/c1-7(25)23-15-10(26)4-19(18(29)30,32-17(15)16(28)11(27)6-24)31-12-5-22-9-3-2-8(20)14(21)13(9)12;/h2-3,5,10-11,15-17,22,24,26-28H,4,6H2,1H3,(H,23,25)(H,29,30);/q;+1/p-1/t10-,11+,15+,16+,17+,19+;/m0./s1
• InChIKey: MNWWXEDVLXNFDD-GNZCRVNMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (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: sodium (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: N-Acetyl-2-O-(5-bromo-4-chloro-1H-indol-3-yl)-α-neuraminic Acid Monosodium Salt; 5-bromo-4-chloro-1H-indol-3-yl 5-(Acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic Acid Monosodium Salt; 5-Bromo-4-chloro-3-indolyl-α-D-N-acetylneuraminic Acid, Sodium Salt

Database IDs

• CAS Number: 160369-85-7
• PubChem SID: 162256933
• PubChem CID: 71307251

CALCULATED PROPERTIES

• Acid pKa: 2.7614555
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.4326632
• LogD (pH = 7.4): -3.2551994
• Log P: 0.2417734
• Molar Refractivity: 122.3925 cm^3
• Polarizability: 45.630375 Å^3
• Polar Surface Area: 184.4 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >183°C dec.

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B682300

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)