5-Bromo-4-chloro-3-indolyl α-D-N-acetylneuraminic acid sodium salt - ≥97% , CAS No.160369-85-7

CAS: 160369-85-7 Cat. No.: X110183 Molecular Weight: 559.72 EC Number: 687-110-8 PubChem CID: 71307251

GRADE & PURITY ≥97%

Synonyms

Sodium (2S,4S,5R,6R)-5-acetamido-2-((5-bromo-4-chloro-1H-indol-3-yl)oxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate | AS-74019 | MFCD00792680 | X-Neu5Ac | 5-BROMO-4-CHLORO-3-INDOLYL--D-N-ACETYLNEURAMINIC ACID, SODIUM SAL

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

A chromogenic substrate.

Specifications

Synonyms

Sodium (2S, 4S, 5R, 6R)-5-acetamido-2-((5-bromo-4-chloro-1H-indol-3-yl)oxy)-4-hydroxy-6-((1R, 2R)-1, 2, 3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate | AS-74019 | MFCD00792680 | X-Neu5Ac | 5-BROMO-4-CHLORO-3-INDOLYL--D-N-ACETYLNEURAMINIC ACID, SODIUM SAL

Specifications & Purity

≥97%

Biochemical and Physiological Mechanisms

X-NeuNAc is a chromogenic substrate for neuraminidase.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥97%

Names and Identifiers

• Canonical Smiles: CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)[O-])OC2=CNC3=C2C(=C(C=C3)Br)Cl)O.[Na+]
• IUPAC Name: sodium;(2S,4S,5R,6R)-5-acetamido-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• InChIKey: MNWWXEDVLXNFDD-GNZCRVNMSA-M
• 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
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](C[C@@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)[O-])OC2=CNC3=C2C(=C(C=C3)Br)Cl)O.[Na+]
• WGK Germany: 1
• PubChem CID: 71307251
• Molecular Weight: 559.72

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Sugar acids and derivatives
          • Level6 Sugar amino acids and derivatives
            • Level7 Pyranoid amino acids and derivatives
              • Level8 Neuraminic acids and derivatives
                • Level9 N-acylneuraminic acids and derivatives
                  • Level10 N-acylneuraminic acids

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Sugar acids and derivatives - Sugar amino acids and derivatives - Pyranoid amino acids and derivatives - Neuraminic acids and derivatives - N-acylneuraminic acids and derivatives
• Direct Parent: N-acylneuraminic acids
• Alternative Parents: Neuraminic acids C-glucuronides C-glycosyl compounds Indoles Ketals Substituted pyrroles Pyrans Aryl bromides Oxanes Aryl chlorides Benzenoids Acetamides Heteroaromatic compounds Secondary carboxylic acid amides Secondary alcohols Carboxylic acid salts Polyols Oxacyclic compounds Azacyclic compounds Carboxylic acids Monocarboxylic acids and derivatives Organic metal halides Primary alcohols Organobromides Carbonyl compounds Organochlorides Organic zwitterions Hydrocarbon derivatives Organic sodium salts Organic oxides Organopnictogen compounds Organonitrogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: N-acylneuraminic acid - Neuraminic acid - C-glucuronide - Glycosyl compound - C-glycosyl compound - Indole or derivatives - Indole - Ketal - Aryl halide - Substituted pyrrole - Aryl bromide - Oxane - Benzenoid - Aryl chloride - Pyran - Pyrrole - Heteroaromatic compound - Acetamide - Secondary alcohol - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid salt - Acetal - Organic metal halide - Oxacycle - Carboxylic acid derivative - Azacycle - Carboxylic acid - Organic alkali metal salt - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Polyol - Organic sodium salt - Organic oxide - Alcohol - Organopnictogen compound - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic salt - Organohalogen compound - Organobromide - Organochloride - Organonitrogen compound - Organic zwitterion - Primary alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: water: 50 mg/mL, clear, colorless to faintly yellow
• Molecular Weight: 559.700 g/mol
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 558.002 Da
• Monoisotopic Mass: 558.002 Da
• Topological Polar Surface Area: 184.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 712.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Menghan Chen, Liqing Wang, Shuyan Xing, Yong Yang, Rong Rong.  (2022)  Rapid screening of neuraminidase inhibitors with the benzoic acid skeleton from Paeonia suffruticosa Andrews by solid-phase extraction with an enzyme activity switch combined with mass spectrometry analysis.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:35717865] [10.1016/j.chroma.2022.463213]