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

CAS: 38520-57-9 Cat. No.: N423782 Molecular Weight: 162.21 EC Number: 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

Overview

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

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

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

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

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Canonical Smiles: 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
• Isomeric SMILES: CC(=O)N[C@@H](CS)C(=O)N
• WGK Germany: 3
• Molecular Weight: 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
    • Class 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
• Class: 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
• Description: 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

Chemical and Physical Properties

• Sensitivity: Air sensitive
• Melt Point(°C): 149 °C
• Molecular Weight: 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

References

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]