S-Nitrosylglutathione(GSNO) - ≥95% , CAS No.57564-91-7

CAS: 57564-91-7 Cat. No.: S136669 Molecular Weight: 336.32 EC Number: 637-341-5 PubChem CID: 104858

GRADE & PURITY ≥95%

Synonyms

(2S)-2-amino-5-[[(1R)-2-(carboxymethylamino)-1-(nitrososulfanylmethyl)-2-oxo-ethyl]amino]-5-oxo-pentanoic acid | CCRIS 2095 | SR-01000946622-1 | N-(N-L-gamma-glutamyl- S-Nitroso-L-cysteinyl)glycine | S-Nitrosoglutathione, >=97% | HY-D0845 | EN300-221929 |

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

S-Nitrosoglutathione (GSNO) is an endogenous nitrogen oxide and is highly distributed in extracellular fluids of the lung and brain.

S-Nitrosoglutathione (GSNO), an amino acid nitric oxide donor, when under physiological conditions spontaneously releases nitric oxide. In research it has been observed to selectively inhibit platelet activation and display cardioprotective effects. This product also inhibits NF-κB activation, endothelial cell proliferation and cathepsin B (cysteine proteases). GNSO has demonstrated dose dependent effects on Thymocytes by inducing apoptosis in T cells in low concentrations (< 0.6 mM), while protecting T cells from apoptosis in higher concentrations (1-2 mM).

S-Nitrosoglutathione (GSNO) has been used:

• as a standard in reversed phase chromatography coupled to chemical vapour generation and atomic fluorescence detector (RPC-CVGAFS) and reversed phase chromatography fluorimetric (RPC-FD).

• as a standard in spectrophotometric and high-performance liquid chromatography (HPLC) assay.

A spontaneously releasing nitric oxide donor which inhibits NFκB and platelet activation.

Specifications

Synonyms

(2S)-2-amino-5-[[(1R)-2-(carboxymethylamino)-1-(nitrososulfanylmethyl)-2-oxo-ethyl]amino]-5-oxo-pentanoic acid | CCRIS 2095 | SR-01000946622-1 | N-(N-L-gamma-glutamyl- S-Nitroso-L-cysteinyl)glycine | S-Nitrosoglutathione, >=97% | HY-D0845 | EN300-221929 |

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

A carrier of nitric oxide. Breaks down at physiological pH to produce nitric oxide. Relaxes smooth muscle and inhibits platelet aggregation.

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Note

Unstable; make up solutions fresh and use immediately. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504756588
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756588
• Canonical Smiles: C(CC(=O)NC(CSN=O)C(=O)NCC(=O)O)C(C(=O)O)N
• IUPAC Name: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• InChIKey: HYHSBSXUHZOYLX-WDSKDSINSA-N
• INCHI: 1S/C10H16N4O7S/c11-5(10(19)20)1-2-7(15)13-6(4-22-14-21)9(18)12-3-8(16)17/h5-6H,1-4,11H2,(H,12,18)(H,13,15)(H,16,17)(H,19,20)/t5-,6-/m0/s1
• Isomeric SMILES: C(CC(=O)N[C@@H](CSN=O)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
• WGK Germany: 3
• RTECS: MC0558000
• PubChem CID: 104858
• Molecular Weight: 336.32

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Not available
• Direct Parent: Peptides
• Alternative Parents: N-acyl-alpha amino acids L-alpha-amino acids Fatty acids and conjugates Dicarboxylic acids and derivatives Nitrosothiols Amino acids Sulfenyl compounds Propargyl-type 1,3-dipolar organic compounds Carboxylic acids Carboximidic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha peptide - N-acyl-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Alpha-amino acid - Alpha-amino acid or derivatives - L-alpha-amino acid - Dicarboxylic acid or derivatives - Fatty acid - Organic s-nitroso compound - Amino acid or derivatives - Amino acid - Nitrosothiol - Nitrosothiol-group - Organic nitroso compound - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Sulfenyl compound - Hydrocarbon derivative - Organic oxide - Primary aliphatic amine - Organopnictogen compound - Amine - Organic nitrogen compound - Organic oxygen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Primary amine - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
• External Descriptors: glutathione derivative

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

Associated Targets(Human)

CASP3 Tchem Caspase-3 (3632 Activities)

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PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

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IMR-32 (1082 Activities)

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SH-SY5Y (11521 Activities)

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SK-N-SH (1499 Activities)

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HeLa (62764 Activities)

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P4HB Tchem Protein disulfide-isomerase (716 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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GMNN Tbio Geminin (128009 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

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RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

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HEK-293T (167025 Activities)

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RAN Tchem GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 (21853 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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protease Human rhinovirus A protease (1343 Activities)

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Escherichia coli (133304 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Bacillus cereus (7522 Activities)

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Candida tropicalis (8381 Activities)

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Rattus norvegicus (775804 Activities)

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rhinovirus B14 (1052 Activities)

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B104 (18 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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GAPDH Glyceraldehyde-3-phosphate dehydrogenase (59 Activities)

Discover Target: GAPDH

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (25 mg/ml), DMSO (20 mg/ml), and PBS. Insoluble in 100% ethanol, methanol, and DMF.
• Molecular Weight: 336.320 g/mol
• XLogP3: -4.800
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 336.074 Da
• Monoisotopic Mass: 336.074 Da
• Topological Polar Surface Area: 214.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 445.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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. Jia Kong, Jinyao Hu, Jia Li, Jiaxing Zhang, Yuhe Shen, Tianli Yue, Xihui Shen, Yuefei Wang, Zhonghong Li, Yinqiang Xia.  (2023)  Rethreading Design of Ratiometric roGFP2 Mimetic Peptide for Hydrogen Peroxide Sensing.  ANALYTICAL CHEMISTRY,      [PMID:37161261] [10.1021/acs.analchem.3c00486]

2. Ying Zhang, Tianfu Zhou, Jian Li, Nuo Xu, Mingze Cai, Hong Zhang, Qinfu Zhao, Siling Wang.  (2023)  Au Catalyzing Control Release NO in vivo and Tumor Growth-Inhibiting Effect in Chemo-Photothermal Combination Therapy.  International Journal of Nanomedicine,      [PMID:33824588] [10.2147/IJN.S270466]

3. Jianwen Zhang, Xianlan Ke, Maotao Huang, Xinyu Pei, Shuai Gao, Dimeng Wu, Junying Chen, Yajun Weng.  (2022)  NO released via both a Cu-MOF-based donor and surface-catalyzed generation enhances anticoagulation and antibacterial surface effects.  Biomaterials Science,  11  (1): (322-338).  [PMID:36448996] [10.1039/D2BM01515C]

4. Yue Xu, Xia Jiang, Chuan Niu, Shaojie Yang, Xiong Xiao, Ziwei Huang, Li Feng.  (2022)  Preparation and Assessment of Nitric Oxide-Releasing Small-Diameter Collagen-Based Vascular Graft for Vascular Regeneration Applications.  MACROMOLECULAR MATERIALS AND ENGINEERING,  307  (7): (2100862).  [PMID:] [10.1002/mame.202100862]

5. Zhang Sulei, Sun Jun, Guo Shuaihang, Wang Yichen, Zhang Yuheng, Lei Jiao, Liu Xiaoli, Chen Hong.  (2024)  Balancing functions of antifouling, nitric oxide release and vascular cell selectivity for enhanced endothelialization of assembled multilayers.  Regenerative Biomaterials,      [PMID:39323744] [10.1093/rb/rbae096]

6. Yong Gao, Shan Bai, Kongying Zhu, Xiaoyan Yuan.  (2024)  Electrospun membranes of diselenide-containing poly(ester urethane)urea for in situ catalytic generation of nitric oxide.  JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION,      [PMID:38386369] [10.1080/09205063.2024.2319416]

7. Denghai Sheng, Shuaihang Guo, Aiqing Li, Qiulian Wu, Mengying Zhan, Xiaoli Liu, Hong Chen.  (2025)  NO-Releasing Metal–Organic Framework-Based Composite Coatings with Heparin-Mimicking Copolymers on Titanium Substrates: Impact on Vascular Cell Behavior.  BIOMACROMOLECULES,      [PMID:40138522] [10.1021/acs.biomac.5c00016]

8. Rongrong Luo, Jingjing Su, Wenying Zhang, Wenguang Huang, Qianqian Zhou, Pengchao Sun, Yongxing Zhao.  (2024)  Targeted delivery of NO donor and ROS scavenger for synergistic treatment of rheumatoid arthritis.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:38579400] [10.1016/j.biopha.2024.116540]

9. Shen Wenqi, Li Yecheng, Yang Ziyi, Li Wenjing, Cao Yi, Liu Yilin, Wang Zheng, Pei Renjun, Xing Chungen.  (2024)  Tumor microenvironment reprogramming combined with immunogenic enhancement by nanoemulsions potentiates immunotherapy.  JOURNAL OF NANOBIOTECHNOLOGY,  22  (1): (1-14).  [PMID:38581017] [10.1186/s12951-024-02401-y]

10. Aiqing Li, Jun Sun, Denghai Sheng, Shengen Gu, Mengying Zhan, Xiaoli Liu, Hong Chen.  (2025)  CuBTTri MOF-Functionalized Hyaluronic Acid-Polydopamine Composite Coating for Selective Endothelialization and Enhanced Hemocompatibility on Polydimethylsiloxane Surfaces.  ACS Applied Bio Materials,      [PMID:40700341] [10.1021/acsabm.5c00780]

11. Jun Sun, Sulei Zhang, Yichen Wang, Denghai Sheng, Shengjie Liu, Yu Rao, Aiqing Li, Yuchun Pan, John L. Brash, Xiaoli Liu, Hong Chen.  (2025)  A multifunctional endothelial-mimetic surface: Synergistically combating thrombus formation by releasing nitric oxide, promoting fibrinolysis, and enhancing endothelialization.  Colloid and Interface Science Communications,      [PMID:] [10.1016/j.colcom.2025.100847]

12. Shuaihang Guo, Shengen Gu, Qiulian Wu, Mengying Zhan, Lisha Pan, Dan Li, Yiping Chen, Xiaoli Liu.  (2025)  Biomimetic Cu2+/Zn2+ bimetallic surface with glycocalyx-mimicking polymer for selective vascular cell regulation and enhanced hemocompatibility.  Biomaterials Advances,      [PMID:41308531] [10.1016/j.bioadv.2025.214616]

13. Xushi Niu, Yazhuo Jia, Shuxuan Zhao, Lan Jiang, Junjun Ni, Enjun Zhu, Weina Han, Jie Yang, Yijie Qiao, Hailin Zhou, Yiyi Xiong, Jie Hu.  (2025)  Endothelium-Inspired Structurally Enhanced Offensive–Defensive Coating for Combating Thrombosis and Biofouling.  ACS Applied Polymer Materials,      [PMID:] [10.1021/acsapm.5c03649]

14. Xu Maoya, Wang Yilin, Liu Bo, Wang Binyou, Wu Jianfei, Liu Yu, Cai Duanfang, Liu Kezhi, Tan Youguo.  (2026)  Synergistic antioxidant and antibacterial hydrogel for accelerated wound healing through ROS scavenging and pathogen elimination.  Scientific Reports,      [PMID:] [10.1038/s41598-026-52575-8]