gamma-Glutamylcysteine (BioDeep_00000002897)

 

Secondary id: BioDeep_00000228562, BioDeep_00000400313, BioDeep_00000405412, BioDeep_00001878610

natural product human metabolite Endogenous blood metabolite PANOMIX_OTCML-2023 BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid

化学式: C8H14N2O5S (250.0623394)
中文名称: γ-谷氨酰半胱氨酸, G-谷氨酸-半胱-三氟乙酸盐
谱图信息: 最多检出来源 Homo sapiens(blood) 0.8%

Reviewed

Last reviewed on 2024-08-14.

Cite this Page

gamma-Glutamylcysteine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/gamma-glutamylcysteine (retrieved 2024-11-21) (BioDeep RN: BioDeep_00000002897). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(CC(=O)NC(CS)C(=O)O)C(C(=O)O)N
InChI: InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)

描述信息

gamma-Glutamylcysteine is a dipeptide composed of gamma-glutamate and cysteine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. gamma-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in the glutamate metabolism pathway (KEGG).
G-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in glutamate metabolism pathway (KEGG). gamma-Glutamyl-cysteine is found in many foods, some of which are cardamom, hyacinth bean, oil palm, and pak choy.
Acquisition and generation of the data is financially supported in part by CREST/JST.
Gamma-glutamylcysteine (γ-Glutamylcysteine), a dipeptide containing cysteine and glutamic acid, is a precursor to glutathione (GSH). Gamma-glutamylcysteine is a cofactor for glutathione peroxidase (GPx) to increase GSH levels[1].

同义名列表

35 个代谢物同义名

(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid; 2-amino-5-[(1-carboxy-2-sulfanylethyl)amino]-5-oxopentanoic acid; N-L-gamma-Glutamyl-L-cysteine; γ-L-Glutamyl-L-cysteine; L-gamma-Glutamyl-L-cysteine; gamma-L-Glutamyl-L-cysteine; N-L-gamma-Glutamylcysteine; N-Γ-L-glutamyl-L-cysteine; N-L-Γ-glutamyl-L-cysteine; N-gamma-Glutamylcysteine; L-gamma-Glutamylcysteine; L-Γ-glutamyl-L-cysteine; g-L-Glutamyl-L-cysteine; gamma-Glutamyl-cysteine; L-g-Glutamyl-L-cysteine; Γ-L-glutamyl-L-cysteine; 5-L-Glutamyl-L-cysteine; N-L-Γ-glutamylcysteine; Gamma-glutamylcysteine; L-g-Glutamylcysteine; L-Γ-glutamylcysteine; N-Γ-glutamylcysteine; 5-L-Glutamylcysteine; des-Gly-glutathione; H-gamma-Glu-cys-OH; Γ-glutamylcysteine; g-Glutamylcysteine; gamma-L-Glu-L-cys; γ-Glu-Cys; gamma-Glu-cys; Γ-L-glu-L-cys; g-Glu-cys; Γ-glu-cys; gamma-L-Glutamyl-L-cysteine; ?Glu-Cys



数据库引用编号

29 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

398 个相关的代谢反应过程信息。

Reactome(15)

BioCyc(3)

WikiPathways(3)

Plant Reactome(317)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(59)

PharmGKB(0)

6 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Jie Liu, Shuai Lu, Xiaoxue Zhang, Jinyi Zhou, Xintong Yan, Huimin Liu, Juanjuan Liang, Lan Luo, Da Zhou, Zhimin Yin. γ-Glutamylcysteine alleviates ethanol-induced hepatotoxicity via suppressing oxidative stress, apoptosis, and inflammation. Journal of food biochemistry. 2022 10; 46(10):e14318. doi: 10.1111/jfbc.14318. [PMID: 35822930]
  • Peter Pressman Md, Wallace John Bridge, Martin Hani Zarka, A Wallace Hayes, Roger Clemens. Dietary γ-Glutamylcysteine: Its Impact on Glutathione Status and Potential Health Outcomes. Journal of dietary supplements. 2022; 19(2):259-270. doi: 10.1080/19390211.2020.1856266. [PMID: 33307893]
  • Wei Luo, Yuming Long, Zili Feng, Rui Li, Xiaojia Huang, Jiaxin Zhong, Dongyun Liu, Hongbo Zhao. A γ-glutamylcysteine ligase AcGCL alleviates cadmium-inhibited fructooligosaccharides metabolism by modulating glutathione level in Allium cepa L. Journal of hazardous materials. 2021 10; 419(?):126255. doi: 10.1016/j.jhazmat.2021.126255. [PMID: 34157465]
  • Yue Liu, Zheng Chen, Ben Li, Hua Yao, Martin Zarka, Jeffrey Welch, Perminder Sachdev, Wallace Bridge, Nady Braidy. Supplementation with γ-glutamylcysteine (γ-GC) lessens oxidative stress, brain inflammation and amyloid pathology and improves spatial memory in a murine model of AD. Neurochemistry international. 2021 03; 144(?):104931. doi: 10.1016/j.neuint.2020.104931. [PMID: 33276023]
  • Mayu Onozato, Kana Kobata, Tatsuya Sakamoto, Hideaki Ichiba, Takeshi Fukushima. LC-MS/MS Analysis of Thiol-Containing Amino Acids in Exosomal Fraction of Serum. Journal of chromatographic science. 2020 Jul; 58(7):636-640. doi: 10.1093/chromsci/bmaa028. [PMID: 32577740]
  • Sho Kobayashi, Yoshitaka Ikeda, Yuhei Shigeno, Hiroyuki Konno, Junichi Fujii. γ-Glutamylcysteine synthetase and γ-glutamyl transferase as differential enzymatic sources of γ-glutamylpeptides in mice. Amino acids. 2020 Apr; 52(4):555-566. doi: 10.1007/s00726-020-02835-2. [PMID: 32170467]
  • Nahid Tamanna, Kathryn Kroeker, Kristen Braun, Sheena Banh, Jason R Treberg. The effect of short-term methionine restriction on glutathione synthetic capacity and antioxidant responses at the whole tissue and mitochondrial level in the rat liver. Experimental gerontology. 2019 11; 127(?):110712. doi: 10.1016/j.exger.2019.110712. [PMID: 31472257]
  • Samir A Salama, Hany H Arab, Memy H Hassan, Majed M Al Robaian, Ibrahim A Maghrabi. Cadmium-induced hepatocellular injury: Modulatory effects of γ-glutamyl cysteine on the biomarkers of inflammation, DNA damage, and apoptotic cell death. Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS). 2019 Mar; 52(?):74-82. doi: 10.1016/j.jtemb.2018.12.003. [PMID: 30732903]
  • Yang Yang, Ling Li, Qiyun Hang, Yuan Fang, Xiaoliang Dong, Peng Cao, Zhimin Yin, Lan Luo. γ-glutamylcysteine exhibits anti-inflammatory effects by increasing cellular glutathione level. Redox biology. 2019 01; 20(?):157-166. doi: 10.1016/j.redox.2018.09.019. [PMID: 30326393]
  • Guirong Tang, Shenghui Xing, Sunjun Wang, Liangliang Yu, Xuan Li, Christian Staehelin, Menghua Yang, Li Luo. Regulation of cysteine residues in LsrB proteins from Sinorhizobium meliloti under free-living and symbiotic oxidative stress. Environmental microbiology. 2017 Dec; 19(12):5130-5145. doi: 10.1111/1462-2920.13992. [PMID: 29124841]
  • Yu Jiang, Rongsheng Tao, Zhengquan Shen, Liangdong Sun, Fuyun Zhu, Sheng Yang. Enzymatic Production of Glutathione by Bifunctional γ-Glutamylcysteine Synthetase/Glutathione Synthetase Coupled with In Vitro Acetate Kinase-Based ATP Generation. Applied biochemistry and biotechnology. 2016 Dec; 180(7):1446-1455. doi: 10.1007/s12010-016-2178-5. [PMID: 27380420]
  • Samir A Salama, Hany H Arab, Ibrahim A Maghrabi, Memy H Hassan, Mohammed S AlSaeed. Gamma-Glutamyl Cysteine Attenuates Tissue Damage and Enhances Tissue Regeneration in a rat Model of Lead-Induced Nephrotoxicity. Biological trace element research. 2016 Sep; 173(1):96-107. doi: 10.1007/s12011-016-0624-4. [PMID: 26767370]
  • Jian Yang, Ming-Xing Gao, Han Hu, Xiao-Meng Ding, Hong-Wei Lin, Lei Wang, Ji-Ming Xu, Chuan-Zao Mao, Fang-Jie Zhao, Zhong-Chang Wu. OsCLT1, a CRT-like transporter 1, is required for glutathione homeostasis and arsenic tolerance in rice. The New phytologist. 2016 07; 211(2):658-70. doi: 10.1111/nph.13908. [PMID: 26918637]
  • Sultan Alqahtani, Ayman M Mahmoud. Gamma-Glutamylcysteine Ethyl Ester Protects against Cyclophosphamide-Induced Liver Injury and Hematologic Alterations via Upregulation of PPARγ and Attenuation of Oxidative Stress, Inflammation, and Apoptosis. Oxidative medicine and cellular longevity. 2016; 2016(?):4016209. doi: 10.1155/2016/4016209. [PMID: 28074115]
  • Hsin-Ho Wei, Martha Rowe, Jean-Jack M Riethoven, Ryan Grove, Jiri Adamec, Yusuke Jikumaru, Paul Staswick. Overaccumulation of γ-Glutamylcysteine in a Jasmonate-Hypersensitive Arabidopsis Mutant Causes Jasmonate-Dependent Growth Inhibition. Plant physiology. 2015 Oct; 169(2):1371-81. doi: 10.1104/pp.15.00999. [PMID: 26282239]
  • Chuanxin Ma, Sudesh Chhikara, Rakesh Minocha, Stephanie Long, Craig Musante, Jason C White, Baoshan Xing, Om Parkash Dhankher. Reduced Silver Nanoparticle Phytotoxicity in Crambe abyssinica with Enhanced Glutathione Production by Overexpressing Bacterial γ-Glutamylcysteine Synthase. Environmental science & technology. 2015 Aug; 49(16):10117-26. doi: 10.1021/acs.est.5b02007. [PMID: 26186015]
  • Samir A Salama, Mohammad S Al-Harbi, Mohamed S Abdel-Bakky, Hany A Omar. Glutamyl cysteine dipeptide suppresses ferritin expression and alleviates liver injury in iron-overload rat model. Biochimie. 2015 Aug; 115(?):203-11. doi: 10.1016/j.biochi.2015.06.006. [PMID: 26093100]
  • Hui Chan Kwak, Young-Mi Kim, Soo Jin Oh, Sang Kyum Kim. Sulfur amino acid metabolism in Zucker diabetic fatty rats. Biochemical pharmacology. 2015 Aug; 96(3):256-66. doi: 10.1016/j.bcp.2015.05.014. [PMID: 26047850]
  • Nsisong Ikpa, Rachel Forman, Kendra Garchow, Ernest Sukowski, Darryl R Peterson. In Vitro Studies on Degradation of Gamma-L-Glutamyl-L-Cysteine and Gamma-L-Glutamyl-D-Cysteine in Blood: Implications for Treatment of Stroke. American journal of therapeutics. 2015 Jul; 22(4):e97-e106. doi: 10.1097/mjt.0000000000000246. [PMID: 25844481]
  • Dehong Tan, Yao Zhang, Lulu Chen, Ling Liu, Xuan Zhang, Zhaoxia Wu, Bing Bai, Shujuan Ji. Decreased glycation and structural protection properties of γ-glutamyl-S-allyl-cysteine peptide isolated from fresh garlic scales (Allium sativum L.). Natural product research. 2015; 29(23):2219-22. doi: 10.1080/14786419.2014.1003065. [PMID: 25631559]
  • Jiali He, Hong Li, Chaofeng Ma, Yanli Zhang, Andrea Polle, Heinz Rennenberg, Xingqi Cheng, Zhi-Bin Luo. Overexpression of bacterial γ-glutamylcysteine synthetase mediates changes in cadmium influx, allocation and detoxification in poplar. The New phytologist. 2015 Jan; 205(1):240-54. doi: 10.1111/nph.13013. [PMID: 25229726]
  • Amit Kumar, Rana Pratap Singh, Pradyumna Kumar Singh, Surabhi Awasthi, Debasis Chakrabarty, Prabodh Kumar Trivedi, Rudra Deo Tripathi. Selenium ameliorates arsenic induced oxidative stress through modulation of antioxidant enzymes and thiols in rice (Oryza sativa L.). Ecotoxicology (London, England). 2014 Sep; 23(7):1153-63. doi: 10.1007/s10646-014-1257-z. [PMID: 24985886]
  • Yue-Qin Cai, Li-Zong Zhang, De-Jun Wang, Fang-Ming Chen, Zhi-Yun Chen, Ke-Yan Zhu, Jian-Shuang Li, Mao-Xiang Yan. [Effect of Nrf2 and related factors on the progression of nonalcoholic steatohepatitis]. Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology. 2014 Sep; 30(5):465-70. doi: NULL. [PMID: 25571645]
  • Yumiko Kono, Hideaki Iizuka, Muneki Isokawa, Makoto Tsunoda, Hideaki Ichiba, Kiyomi Sadamoto, Takeshi Fukushima. HPLC-fluorescence determination of thiol compounds in the serum of human male and female subjects using HILIC-mode column. Biomedical chromatography : BMC. 2014 May; 28(5):589-93. doi: 10.1002/bmc.3086. [PMID: 24500895]
  • Noor Nahar, Aminur Rahman, Maria Moś, Tomasz Warzecha, Sibdas Ghosh, Khaled Hossain, Neelu N Nawani, Abul Mandal. In silico and in vivo studies of molecular structures and mechanisms of AtPCS1 protein involved in binding arsenite and/or cadmium in plant cells. Journal of molecular modeling. 2014 Mar; 20(3):2104. doi: 10.1007/s00894-014-2104-0. [PMID: 24554125]
  • Deepak Kumar, Riddhi Datta, Ragini Sinha, Aparupa Ghosh, Sharmila Chattopadhyay. Proteomic profiling of γ-ECS overexpressed transgenic Nicotiana in response to drought stress. Plant signaling & behavior. 2014; 9(8):e29246. doi: 10.4161/psb.29246. [PMID: 25763614]
  • Takeshi Fukushima, Hideaki Iizuka, Ayaka Yokota, Takehiro Suzuki, Chihiro Ohno, Yumiko Kono, Minami Nishikiori, Ayaka Seki, Hideaki Ichiba, Yoshinori Watanabe, Seiji Hongo, Mamoru Utsunomiya, Masaki Nakatani, Kiyomi Sadamoto, Takashi Yoshio. Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PloS one. 2014; 9(7):e101652. doi: 10.1371/journal.pone.0101652. [PMID: 25004141]
  • Victoria Pastor, Estrella Luna, Jurriaan Ton, Miguel Cerezo, Pilar García-Agustín, Victor Flors. Fine tuning of reactive oxygen species homeostasis regulates primed immune responses in Arabidopsis. Molecular plant-microbe interactions : MPMI. 2013 Nov; 26(11):1334-44. doi: 10.1094/mpmi-04-13-0117-r. [PMID: 24088017]
  • Darryl R Peterson, Ernest J Sukowski, Demetrios Zikos. Blood-brain barrier transport pathways for cytoprotective thiols. American journal of therapeutics. 2013 Sep; 20(5):469-79. doi: 10.1097/mjt.0b013e31829e8b7f. [PMID: 24670783]
  • Bin Hu, Judy Simon, Heinz Rennenberg. Drought and air warming affect the species-specific levels of stress-related foliar metabolites of three oak species on acidic and calcareous soil. Tree physiology. 2013 May; 33(5):489-504. doi: 10.1093/treephys/tpt025. [PMID: 23619385]
  • Yansen Li, Yi Huang, Yuanguo Piao, Kentaro Nagaoka, Gen Watanabe, Kazuyoshi Taya, ChunMei Li. Protective effects of nuclear factor erythroid 2-related factor 2 on whole body heat stress-induced oxidative damage in the mouse testis. Reproductive biology and endocrinology : RB&E. 2013 Mar; 11(?):23. doi: 10.1186/1477-7827-11-23. [PMID: 23514035]
  • Kang Uk Yun, Chang Seon Ryu, Ji-Yoon Lee, Jung-Ran Noh, Chul-Ho Lee, Hyun-Sun Lee, Jong Soon Kang, Song Kyu Park, Bong-Hee Kim, Sang Kyum Kim. Hepatic metabolism of sulfur amino acids in db/db mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Mar; 53(?):180-6. doi: 10.1016/j.fct.2012.11.046. [PMID: 23220616]
  • Kang Uk Yun, Chang Seon Ryu, Jung Min Oh, Chung Hyun Kim, Kye Sook Lee, Chul-Ho Lee, Hyun-Sun Lee, Bong-Hee Kim, Sang Kyum Kim. Plasma homocysteine level and hepatic sulfur amino acid metabolism in mice fed a high-fat diet. European journal of nutrition. 2013 Feb; 52(1):127-34. doi: 10.1007/s00394-011-0294-0. [PMID: 22209966]
  • S D Chandler, M H Zarka, S N Vinaya Babu, Y S Suhas, K R Raghunatha Reddy, W J Bridge. Safety assessment of gamma-glutamylcysteine sodium salt. Regulatory toxicology and pharmacology : RTP. 2012 Oct; 64(1):17-25. doi: 10.1016/j.yrtph.2012.05.008. [PMID: 22698997]
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  • Chava B Pocernich, D Allan Butterfield. Elevation of glutathione as a therapeutic strategy in Alzheimer disease. Biochimica et biophysica acta. 2012 May; 1822(5):625-30. doi: 10.1016/j.bbadis.2011.10.003. [PMID: 22015471]
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