N-acetylcysteine amide - 10mM in DMSO , CAS No.38520-57-9

CAS: 38520-57-9 Cat. No.: N423782 Peso molecular: 162.21 Número EC: 686-019-0

GRADE & PURITY 10mM in DMSO

Synonyms

NACA | AD4 | Propanamide, 2-(acetylamino)-3-mercapto-, (R)- | OXOLAMINE CITRATE [MI] | Nac amide | UNII-4N69717RKW | (2R)-2-(Acetylamino)-3-mercaptopropanamide | (2R)-2-acetamido-3-sulfanylpropanamide | s5804 | N-acetylcysteine amide, >=98% (HPLC) | Propa

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

N-acetylcysteine amide has been used:
to protect retinal pigment epithelium (RPE) from oxidative stress
to show that increased expression of cell adhesion molecule 4 (CADM4) in oligodendrocytes inhibits myelination
to protect cells from apoptosis induced by shikonin plus erlotinib/gefitinib
as a component in various culture media
as an antioxidant to reduce oxidative stress in brains of homozygous Drosophila spermine synthase (dSms e/e) mutant flies and melanoma cells.

Specifications

Sinónimos

NACA | AD4 | Propanamide, 2-(acetylamino)-3-mercapto-, (R)- | OXOLAMINE CITRATE [MI] | Nac amide | UNII-4N69717RKW | (2R)-2-(Acetylamino)-3-mercaptopropanamide | (2R)-2-acetamido-3-sulfanylpropanamide | s5804 | N-acetylcysteine amide, >=98% (HPLC) | Propa

Especificaciones y pureza

10mM in DMSO

Mecanismos bioquímicos y fisiológicos

N-acetylcysteine amide is a membrane penetrating antioxidant with antiinflamatory activity through regulation of activation of NF-κB and HIF-1α as well as modulation of ROS. The compound readily crosses cell membranes, replenishes intracellular GSH, and d

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nombres e identificadores

• Sonrisas canónicas: CC(=O)NC(CS)C(=O)N
• IUPAC Name: (2R)-2-acetamido-3-sulfanylpropanamide
• InChIKey: UJCHIZDEQZMODR-BYPYZUCNSA-N
• INCHI: 1S/C5H10N2O2S/c1-3(8)7-4(2-10)5(6)9/h4,10H,2H2,1H3,(H2,6,9)(H,7,8)/t4-/m0/s1
• Isómeros SMILES: CC(=O)N[C@@H](CS)C(=O)N
• WGK Alemania: 3
• Peso molecular: 162.21
• Reaxy-Rn: 2207757
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2207757&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 N-acyl-alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Clase: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: N-acyl-alpha amino acids and derivatives
• Alternative Parents: Cysteine and derivatives Acetamides Secondary carboxylic acid amides Primary carboxylic acid amides Alkylthiols Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: N-acyl-alpha amino acid or derivatives - Cysteine or derivatives - Acetamide - Secondary carboxylic acid amide - Primary carboxylic acid amide - Carboxamide group - Alkylthiol - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
• 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

Propiedades químicas y físicas

• Sensibilidad: Air sensitive
• Punto de fusión (°C): 149 °C
• Peso molecular: 162.210 g/mol
• XLogP3: -0.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 162.046 Da
• Monoisotopic Mass: 162.046 Da
• Topological Polar Surface Area: 73.200 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 149.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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: 1

Referencias

1. Gang Du, Yicheng Qiao, Zhangpeng Zhuo, Jiaqi Zhou, Xiaorong Li, Zhiming Liu, Yang Li, Haiyang Chen.  (2020)  Lipoic acid rejuvenates aged intestinal stem cells by preventing age-associated endosome reduction.  EMBO REPORTS,      [PMID:32648369] [10.15252/embr.201949583]

2. Zhiming Liu, Gang Du, Yi Chen, Haiyang Chen.  (2025)  Age-associated decline of Coenzyme A leads to intestinal stem cells dysfunction via disturbing iron homeostasis.  PLoS Genetics,  21  (5): (e1011704).  [PMID:40446021] [10.1371/journal.pgen.1011704]