Pyroglutamic acid (BioDeep_00000001870)

 

Secondary id: BioDeep_00000229606, BioDeep_00000399909, BioDeep_00000400414, BioDeep_00000402913, BioDeep_00000405233, BioDeep_00000415816, BioDeep_00000872257

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


代谢物信息卡片


(S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid

化学式: C5H7NO3 (129.0425912)
中文名称: L-焦谷氨酸, 焦谷氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.2%

Reviewed

Last reviewed on 2024-08-20.

Cite this Page

Pyroglutamic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/pyroglutamic_acid (retrieved 2024-11-21) (BioDeep RN: BioDeep_00000001870). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1CC(=O)NC1C(=O)O
InChI: InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1

描述信息

Pyroglutamic acid (5-oxoproline) is a cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. It is formed nonenzymatically from glutamate, glutamine, and gamma-glutamylated peptides, but it can also be produced by the action of gamma-glutamylcyclotransferase on an L-amino acid. Elevated blood levels may be associated with problems of glutamine or glutathione metabolism. This compound is found in substantial amounts in brain tissue and other tissues in bound form, especially skin. It is also present in plant tissues. It is sold, over the counter, as a "smart drug" for improving blood circulation in the brain. Pyroglutamate in the urine is a biomarker for the consumption of cheese. When present in sufficiently high levels, pyroglutamic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of pyroglutamic acid are associated with at least five inborn errors of metabolism including 5-oxoprolinuria, 5-oxoprolinase deficiency, glutathione synthetase deficiency, hawkinsinuria, and propionic acidemia. Pyroglutamic acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. It has been shown that pyroglutamic acid releases GABA from the cerebral cortex and displays anti-anxiety effects in a simple approach-avoidance conflict situation in the rat. In clinical pharmacology experiments, pyroglutamic acid significantly shortens the plasma half-life of ethanol during acute intoxication.
Found in vegetables, fruits and molasses. A cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. Pyroglutamate in the urine is a biomarker for the consumption of cheese
C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent

同义名列表

82 个代谢物同义名

(S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid; (S)-(-)-gamma-Butyrolactam-gamma-carboxylate; (S)-(-)-g-Butyrolactam-g-carboxylic acid; (5S)-2-Oxopyrrolidine-5-carboxylic acid; (S)-(-)-2-Pyrrolidone-5-carboxylic acid; (2S)-5-oxopyrrolidine-2-carboxylic acid; (S)-5-oxo-2-Pyrrolidinecarboxylic acid; 2-Oxopyrrolidine-5(S)-carboxylic acid; L-5-oxo-2-Pyrrolidinecarboxylic acid; (S)-(-)-g-Butyrolactam-g-carboxylate; (S)-2-Pyrrolidone-5-carboxylic acid; (-)-2-Pyrrolidone-5-carboxylic acid; (5S)-2-Oxopyrrolidine-5-carboxylate; (S)-(-)-2-Pyrrolidone-5-carboxylate; (S)-5-oxo-2-Pyrrolidinecarboxylate; 5-Oxopyrrolidine-2-carboxylic acid; 2-L-Pyrrolidone-5-carboxylic acid; 2-Pyrrolidinone-5-carboxylic acid; L-2-Pyrrolidone-5-carboxylic acid; 5-Pyrrolidinone-2-carboxylic acid; 2-Oxopyrrolidine-5(S)-carboxylate; L-5-Pyrrolidone-2-carboxylic acid; L-5-oxo-2-Pyrrolidinecarboxylate; (-)-2-Pyrrolidone-5-carboxylate; 5-Pyrrolidone-2-carboxylic acid; 2-Pyrrolidone-5-carboxylic acid; (S)-2-Pyrrolidone-5-carboxylate; L-Pyrrolidinonecarboxylic acid; Pyrrolidone-5-carboxylic acid; Oxopyrrolidinecarboxylic acid; L-5-Pyrrolidone-2-carboxylate; L-2-Pyrrolidone-5-carboxylate; 5-Pyrrolidinone-2-carboxylate; 2-L-Pyrrolidone-5-carboxylate; 2-Pyrrolidinone-5-carboxylate; L-Pyrrolidonecarboxylic acid; Pyrrolidinonecarboxylic acid; 5-Pyrrolidone-2-carboxylate; L-5-Carboxy-2-pyrrolidinone; L-Pyrrolidinonecarboxylate; Pyrrolidonecarboxylic acid; 5-Carboxy-2-pyrrolidinone; Pyrrolidone-5-carboxylate; Oxopyrrolidinecarboxylate; Pyrrolidinonecarboxylate; L-Pyrrolidonecarboxylate; L-Glutamic acid g-lactam; (S)-Pyroglutamic acid; (-)-Pyroglutamic acid; L-Pyroglutamic acid; Pidolate, magnesium; L-Pyroglutamicacid; Magnesium pidolate; (S)-Pyroglutamate; (-)-Pyroglutamate; Pyroglutamic acid; L-Glutiminic acid; L-5-Oxoproline(2); L-Glutimic acid; L-Pyroglutamate; Glutiminic acid; 5-oxo-L-Proline; L-5-Oxoproline; 5-Oxoprolinate; 5-L-Oxoproline; L-Glutiminate; Glutimic acid; Pyroglutamate; 5-Ketoproline; Pidolic acid; Ajidew a 100; 5-Oxoproline; L-Glutimate; Glutiminate; Pidolidone; Oxoproline; Glutimate; Pidolate; PCA; Pyroglutamic acid; L-Pyroglutamic acid; 5-Oxoproline



数据库引用编号

52 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

276 个相关的代谢反应过程信息。

Reactome(15)

BioCyc(1)

  • γ-glutamyl cycle: a 5-L-glutamyl-L-amino acid + cysteinylglycine ⟶ a standard α amino acid + glutathione

WikiPathways(2)

Plant Reactome(237)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(21)

PharmGKB(0)

192 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

  • Shixiong Jiang, Heather G Marco, Nina Scheich, Shulin He, Zongqing Wang, Gerd Gäde, Dino P McMahon. Comparative analysis of adipokinetic hormones and their receptors in Blattodea reveals novel patterns of gene evolution. Insect molecular biology. 2023 12; 32(6):615-633. doi: 10.1111/imb.12861. [PMID: 37382487]
  • Xiaoyan Yang, Dongqun Xu, Bo Wen, Jian Ji, Zeyu Zhang, Li Li, Shaoping Zhang, Hong Zhi, Jian Kong, Chong Wang, Jun Wang, Hongjie Ruan, Ming Zhang, Lan Wei, Bin Dong, Qin Wang. The mediating role of exhaled breath condensate metabolites in the effect of particulate matter on pulmonary function in schoolchildren: A crossover intervention study. The Science of the total environment. 2023 Jul; 898(?):165517. doi: 10.1016/j.scitotenv.2023.165517. [PMID: 37459994]
  • Pat J Unkefer, Thomas J Knight, Rodolfo A Martinez. The intermediate in a nitrate-responsive ω-amidase pathway in plants may signal ammonium assimilation status. Plant physiology. 2023 01; 191(1):715-728. doi: 10.1093/plphys/kiac501. [PMID: 36303326]
  • Marta Hetman, Karolina Mielko, Sylwia Placzkowska, Aleksandra Bodetko, Piotr Młynarz, Ewa Barg. Predisposition to atherosclerosis in children and adults with trisomy 21: biochemical and metabolomic studies. Pediatric endocrinology, diabetes, and metabolism. 2023; 29(3):143-155. doi: 10.5114/pedm.2023.131162. [PMID: 38031830]
  • Salwa Afifi, Azizia Wahedi, Jean-Paul Paluzzi. Functional insight and cell-specific expression of the adipokinetic hormone/corazonin-related peptide in the human disease vector mosquito, Aedes aegypti. General and comparative endocrinology. 2023 01; 330(?):114145. doi: 10.1016/j.ygcen.2022.114145. [PMID: 36244431]
  • Rui-Kun Zhang, Kun Yan, Hai-Feng Chen, Yang Zhang, Gui-Jin Li, Xiao-Gang Chen, Lin-Pu Ge, Feng Cheng, Zhi-Neng Chen, Xin-Miao Yao. Anti-osteoporotic drugs affect the pathogenesis of gut microbiota and its metabolites: a clinical study. Frontiers in cellular and infection microbiology. 2023; 13(?):1091083. doi: 10.3389/fcimb.2023.1091083. [PMID: 37475958]
  • Yu Zhang, Jie Liu, Yan Wang, Chengpeng Sun, Wenjia Li, Jianjian Qiu, Yanling Qiao, Fan Wu, Xiaokui Huo, Yue An, Baojing Zhang, Shuangcheng Ma, Jian Zheng, Xiaochi Ma. Nucleosides and amino acids, isolated from Cordyceps sinensis, protected against cyclophosphamide-induced myelosuppression in mice. Natural product research. 2022 Dec; 36(23):6056-6059. doi: 10.1080/14786419.2022.2043307. [PMID: 35188001]
  • Yue-Bei Luo, Yangtengyu Liu, Qiuxiang Li, Huiqian Duan, Zhaohui Luo, Huan Yang, Liqun Xu. Integrating 16S RRNA gene sequencing and metabolomics to evaluate the association between gut microbiota and serum metabolites in patients with myositis. Journal of applied microbiology. 2022 Oct; 133(4):2547-2559. doi: 10.1111/jam.15724. [PMID: 35858765]
  • Heather G Marco, Simone König, Gerd Gäde. Mass Spectrometric Proof of Predicted Peptides: Novel Adipokinetic Hormones in Insects. Molecules (Basel, Switzerland). 2022 Oct; 27(19):. doi: 10.3390/molecules27196469. [PMID: 36235010]
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  • Yongzhao Dai, Siqi Chen, Yaqi Li, Guanglong Zhang, Pingping Bi, Ke Nie. Liujunzi Decoction ameliorated cisplatin-induced anorexia by inhibiting the JAK-STAT signaling pathway and coordinating anorexigenic and orexigenic neuropeptides in rats. Journal of ethnopharmacology. 2022 Mar; 285(?):114840. doi: 10.1016/j.jep.2021.114840. [PMID: 34800646]
  • Olga Kubrak, Takashi Koyama, Nadja Ahrentløv, Line Jensen, Alina Malita, Muhammad T Naseem, Mette Lassen, Stanislav Nagy, Michael J Texada, Kenneth V Halberg, Kim Rewitz. The gut hormone Allatostatin C/Somatostatin regulates food intake and metabolic homeostasis under nutrient stress. Nature communications. 2022 02; 13(1):692. doi: 10.1038/s41467-022-28268-x. [PMID: 35121731]
  • Evren Caglar Eroglu, Umran Kucukgoz Gulec, Mehmet Ali Vardar, Semra Paydas. GC-MS based metabolite fingerprinting of serous ovarian carcinoma and benign ovarian tumor. European journal of mass spectrometry (Chichester, England). 2022 Feb; 28(1-2):12-24. doi: 10.1177/14690667221098520. [PMID: 35503418]
  • Xiao-Yan Lan, Zheng-Wu Sun, Gui-Lian Xu, Cheng-Yan Chu, Hua-Min Qin, Shen Li, Xin Geng, Peng Gao, Johannes Boltze, Shen Li. Bone Marrow Mesenchymal Stem Cells Exert Protective Effects After Ischemic Stroke Through Upregulation of Glutathione. Stem cell reviews and reports. 2022 02; 18(2):585-594. doi: 10.1007/s12015-021-10178-y. [PMID: 34449012]
  • Sakura Tanaka, Nilli Zmora, Berta Levavi-Sivan, Yonathan Zohar. Vasoactive Intestinal Peptide Indirectly Elicits Pituitary LH Secretion Independent of GnRH in Female Zebrafish. Endocrinology. 2022 02; 163(2):. doi: 10.1210/endocr/bqab264. [PMID: 34978328]
  • Dalibor Kodrík, Václav Krištůfek, Zdeňka Svobodová. Bee year: Basic physiological strategies to cope with seasonality. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2022 02; 264(?):111115. doi: 10.1016/j.cbpa.2021.111115. [PMID: 34775045]
  • Weilong Zhang, Jihan Huang, Hongxia Liu, Xin Wen, Qingshan Zheng, Lujin Li. Whether Immunostimulants Are Effective in Susceptible Children Suffering From Recurrent Respiratory Tract Infections: A Modeling Analysis Based on Literature Aggregate Data. Journal of clinical pharmacology. 2022 02; 62(2):245-253. doi: 10.1002/jcph.1969. [PMID: 34535904]
  • Bryon N Hughson. PKG acts in the adult corpora cardiaca to regulate nutrient stress-responsivity through adipokinetic hormone. Journal of insect physiology. 2022 01; 136(?):104339. doi: 10.1016/j.jinsphys.2021.104339. [PMID: 34856210]
  • Alexandre Lasse, Marc Deveaux, Jean-Louis Beaudeux, Jean-Herlé Raphalen, Frédéric J Baud, Pascal Houzé. [Plasmatic and urinary pyroglutamic acid measurement by capillary zone electrophoresis in chronic poisoning with acetaminophen in children]. Annales de biologie clinique. 2021 Dec; 79(6):567-578. doi: 10.1684/abc.2021.1689. [PMID: 34961739]
  • Mingzhu Wang, Jiao Chen, Xiaoying Lin, Lin Huang, Haichang Li, Chengping Wen, Zhixing He. High humidity aggravates the severity of arthritis in collagen-induced arthritis mice by upregulating xylitol and L-pyroglutamic acid. Arthritis research & therapy. 2021 12; 23(1):292. doi: 10.1186/s13075-021-02681-x. [PMID: 34852827]
  • Jayoung Kim, Amanda De Hoedt, Emily Wiggins, Kelsey Haywood, Peng Jin, Bennett Greenwood, Niven R Narain, Vladimir Tolstikov, Valerie Bussberg, Kamil E Barbour, Michael A Kiebish, Stephen J Freedland, Jennifer T Anger. Diagnostic Utility of Serum and Urinary Metabolite Analysis in Patients with Interstitial Cystitis/Painful Bladder Syndrome. Urology. 2021 11; 157(?):85-92. doi: 10.1016/j.urology.2021.05.005. [PMID: 34010675]
  • Ashok Mahashur, Agam Vora, Pradyut Waghray, S Z Jafrey, Archana Karadkhele, Snehal Muchhala, Rahul Rathod, Viraj Suvarna. Expert Opinion on Usage of Pidotimod in Adult Patients with Chronic Obstructive Pulmonary Disease: An Indian Perspective. The Journal of the Association of Physicians of India. 2021 Sep; 69(9):11-12. doi: NULL. [PMID: 34585899]
  • Harald F Hofbauer, Christoph Heier, Anantha Krishnan Sen Saji, Ronald P Kühnlein. Lipidome remodeling in aging normal and genetically obese Drosophila males. Insect biochemistry and molecular biology. 2021 06; 133(?):103498. doi: 10.1016/j.ibmb.2020.103498. [PMID: 33221388]
  • Sifang Liao, Mirjam Amcoff, Dick R Nässel. Impact of high-fat diet on lifespan, metabolism, fecundity and behavioral senescence in Drosophila. Insect biochemistry and molecular biology. 2021 06; 133(?):103495. doi: 10.1016/j.ibmb.2020.103495. [PMID: 33171202]
  • Yang Yang, Ying Xiong, Hong-Fei Li, Huai-Jia Zhao, Guang-Hui Tang, Li-Wei Meng, Jin-Jun Wang, Hong-Bo Jiang. The adipokinetic hormone signaling system regulates the sensitivity of Bactrocera dorsalis to malathion. Pesticide biochemistry and physiology. 2021 May; 174(?):104808. doi: 10.1016/j.pestbp.2021.104808. [PMID: 33838709]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Qiong Zhang, Xin Li, Xiaofeng Yin, Haifang Wang, Chen Fu, Hongxia Wang, Kaifei Li, Yao Li, Xiaohe Zhang, Huijun Liang, Kui Li, Haixia Li, Yurong Qiu. Metabolomic profiling reveals serum L-pyroglutamic acid as a potential diagnostic biomarker for systemic lupus erythematosus. Rheumatology (Oxford, England). 2021 02; 60(2):598-606. doi: 10.1093/rheumatology/keaa126. [PMID: 32259244]
  • Anis Zand Irani, Grace Borchert, Brendan Craven, Holly Gibbons. Flucloxacillin and paracetamol induced pyroglutamic acidosis. BMJ case reports. 2021 Jan; 14(1):. doi: 10.1136/bcr-2020-237536. [PMID: 33419747]
  • Claudio Ucciferri, Katia Falasca, Marcella Reale, Manuela Tamburro, Antonio Auricchio, Francesca Vignale, Jacopo Vecchiet. Pidotimod and Immunological Activation in Individuals Infected with HIV. Current HIV research. 2021; 19(3):260-268. doi: 10.2174/1570162x18666210111102046. [PMID: 33430735]
  • Ling-Ling Wei, Tian-Tian Chen, Bi-Yun Luo, Gao-Feng Qiu. Evidences for Red Pigment Concentrating Hormone (RPCH) and Beta-Pigment Dispersing Hormone (β-PDH) Inducing Oocyte Meiotic Maturation in the Chinese Mitten Crab, Eriocheir sinensis. Frontiers in endocrinology. 2021; 12(?):802768. doi: 10.3389/fendo.2021.802768. [PMID: 34975771]
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