MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) (BioDeep_00000002524)

 

Secondary id: BioDeep_00000229696

human metabolite Endogenous blood metabolite LipidSearch Volatile Flavor Compounds


代谢物信息卡片


(5Z,8Z,11Z,14Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoic acid

化学式: C23H38O4 (378.2769948)
中文名称: 2-花生酰基甘油
谱图信息: 最多检出来源 Homo sapiens(blood) 0.33%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/2-arachidonoylglycerol_(20:4) (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000002524). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO
InChI: InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-

描述信息

MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0), also known as 2-arachidonoylglycerol (2-AG), is a unique molecular species of monoacylglycerol isolated in 1995 from rat brain and canine gut as an endogenous ligand for the cannabinoid receptors. 2-AG is rapidly formed from arachidonic acid-containing phospholipids through increased phospholipid metabolism, such as enhanced inositol phospholipid turnover, in various tissues and cells upon stimulation. 2-AG binds to the cannabinoid receptors CB1 and CB2 and exhibits a variety of cannabimimetic activities in vitro and in vivo. 2-AG is an endogenous cannabinoid (endocannabinoid). Endocannabinoids are a class of fatty acid derivatives defined by their ability to interact with the specific cannabinoid receptors that were originally identified as the targets of delta9-tetrahydocannabinol (delta9-THC), the psychoactive component of cannabis. Endocannabinoids have been implicated in a growing number of important physiological and behavioral events. Endocannabinoids are amides, esters, and ethers of long-chain polyunsaturated fatty acids, which act as new lipidic mediators. 2-AG is one of the main endogenous agonists of cannabinoid receptors, able to mimic several pharmacological effects of delta9-THC, the active principle of Cannabis sativa preparations like hashish and marijuana. The activity of AEA and 2-AG at their receptors is limited by cellular uptake through an anandamide membrane transporter (AMT), followed by intracellular degradation. A fatty acid amide hydrolase (FAAH) is the main AEA hydrolase, whereas a monoacylglycerol lipase (MAGL) is critical in degrading 2-AG (PMID: 16515464, 16278487, 16678907).
2-Arachidonoylglycerol (2-AG) is a unique molecular species of monoacylglycerol isolated in 1995 from rat brain and canine gut as an endogenous ligand for the cannabinoid receptors. 2-AG is rapidly formed from arachidonic acid-containing phospholipids through increased phospholipid metabolism, such as enhanced inositol phospholipid turnover, in various tissues and cells upon stimulation. 2-AG binds to the cannabinoid receptors (CB1 and CB2) and exhibits a variety of cannabimimetic activities in vitro and in vivo. 2-Arachidonylglycerol is an endogenous cannabinoid (endocannabinoid). Endocannabinoids are a class of fatty acid derivatives defined by their ability to interact with the specific cannabinoid receptors that were originally identified as the targets of Delta9-tetrahydocannabinol (Delta9-THC), the psychoactive component of cannabis. Endocannabinoids have been implicated in a growing number of important physiological and behavioral events. Endocannabinoids are amides, esters and ethers of long chain polyunsaturated fatty acids, which act as new lipidic mediators. 2-AG is one of the main endogenous agonists of cannabinoid receptors, able to mimic several pharmacological effects of (-)-Delta9-tetrahydrocannabinol (THC), the active principle of Cannabis sativa preparations like hashish and marijuana. The activity of AEA and 2-AG at their receptors is limited by cellular uptake through an anandamide membrane transporter (AMT), followed by intracellular degradation. A fatty acid amide hydrolase (FAAH) is the main AEA hydrolase, whereas a monoacylglycerol lipase (MAGL) is critical in degrading 2-AG. (PMID: 16515464, 16278487, 16678907)
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D063385 - Cannabinoid Receptor Modulators
D018377 - Neurotransmitter Agents > D063385 - Cannabinoid Receptor Modulators > D063386 - Cannabinoid Receptor Agonists

同义名列表

39 个代谢物同义名

(5Z,8Z,11Z,14Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoic acid; (5Z,8Z,11Z,14Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoate; (all-Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoic acid; (all-Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoate; 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate; eicosa-5,8,11,14-tetraenoic acid 1,3-dihydroxypropan-2-yl ester; 2-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-rac-glycerol; 2-Monoarachidonoylglycerolbeta-monoacylglycerol; 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol; 2-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-glycerol; MAG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0); MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0); 2-Monoarachidonoylglycerol; 2-Arachidonoyl-sn-glycerol; MAG(20:4(5Z,8Z,11Z,14Z)); MG(20:4(5Z,8Z,11Z,14Z)); Glyceryl 2-arachidonate; 2-Arachidonoyl-glycerol; 2-arachidonoylglycerol; 2-Arachidonyl glycerol; 2-Arachidonyl-glycerol; 2-Arachidonylglycerol; beta-Monoacylglycerol; MAG(0:0/20:4n6/0:0); 1-Monoacylglyceride; MAG(0:0/20:4W6/0:0); b-Monoacylglycerol; MG(0:0/20:4n6/0:0); MG(0:0/20:4W6/0:0); 1-Monoacylglycerol; MAG(20:4W6); MAG(20:4n6); MG(20:4W6); MG(20:4n6); MAG(20:4); 2-Ara-GL; MG(20:4); 2-AG; 2-Arachidonoylglycerol



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(0)

PlantCyc(0)

代谢反应

145 个相关的代谢反应过程信息。

Reactome(144)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

4 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

  • Chu Chen. Inhibiting degradation of 2-arachidonoylglycerol as a therapeutic strategy for neurodegenerative diseases. Pharmacology & therapeutics. 2023 Apr; 244(?):108394. doi: 10.1016/j.pharmthera.2023.108394. [PMID: 36966972]
  • Joanna Kowalczyk, Barbara Budzyńska, Łukasz Kurach, Daniele Pellegata, Nesrine S El Sayed, Jürg Gertsch, Krystyna Skalicka-Woźniak. Neuropsychopharmacological profiling of scoparone in mice. Scientific reports. 2022 01; 12(1):822. doi: 10.1038/s41598-021-04741-3. [PMID: 35039558]
  • Anne-Sophie Archambault, Julyanne Brassard, Émilie Bernatchez, Cyril Martin, Vincenzo Di Marzo, Michel Laviolette, Louis-Philippe Boulet, Marie-Renée Blanchet, Nicolas Flamand. Human and Mouse Eosinophils Differ in Their Ability to Biosynthesize Eicosanoids, Docosanoids, the Endocannabinoid 2-Arachidonoyl-glycerol and Its Congeners. Cells. 2022 01; 11(1):. doi: 10.3390/cells11010141. [PMID: 35011703]
  • Isabel van Ackern, Angela Kuhla, Björn Kuhla. A Role for Peripheral Anandamide and 2-Arachidonoylglycerol in Short-Term Food Intake and Orexigenic Hypothalamic Responses in a Species with Continuous Nutrient Delivery. Nutrients. 2021 Oct; 13(10):. doi: 10.3390/nu13103587. [PMID: 34684588]
  • Giuseppe Bersani, Francesca Pacitti, Angela Iannitelli, Eleonora Caroti, Adele Quartini, Dionysios Xenos, Michela Marconi, Valentina Cuoco, Benedetta Bigio, Nicole P Bowles, Filippo Weisz, Flaminia Fanelli, Valentina D Di Lallo, Ilaria Belluomo, Ferdinando Nicoletti, Carla Nasca. Inverse correlation between plasma 2-arachidonoylglycerol levels and subjective severity of depression. Human psychopharmacology. 2021 07; 36(4):e2779. doi: 10.1002/hup.2779. [PMID: 33559925]
  • Lian-Jie Hou, Mei-Ying Xie, Wenchu Ye, Guo-Jun Zhao. The endocannabinoid 2-arachidonoylglycerol inhibits endothelial function and repair through cannabinoid 1 (CB1) receptor. International journal of cardiology. 2021 04; 328(?):176. doi: 10.1016/j.ijcard.2020.11.027. [PMID: 33217478]
  • Emiliano Manzo, Aniello Schiano Moriello, Francesco Tinto, Roberta Verde, Marco Allarà, Luciano De Petrocellis, Ester Pagano, Angelo A Izzo, Vincenzo Di Marzo, Stefania Petrosino. A Glucuronic Acid-Palmitoylethanolamide Conjugate (GLUPEA) Is an Innovative Drug Delivery System and a Potential Bioregulator. Cells. 2021 02; 10(2):. doi: 10.3390/cells10020450. [PMID: 33672574]
  • Ahmad Mobed, Fereshteh Kohansal, Ali Ahmadalipour, Mohammad Hasanzadeh, Flor Zargari. Bioconjugation of 2-arachidonoyl glycerol (2-AG) biotinylated antibody with gold nano-flowers toward immunosensing of 2-AG in human plasma samples: A novel immuno-platform for the screening of immunomodulation and neuroprotection using biosensing. Analytical methods : advancing methods and applications. 2021 01; 13(3):311-321. doi: 10.1039/d0ay02135k. [PMID: 33367337]
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  • Niclas Stensson, Björn Gerdle, Malin Ernberg, Kaisa Mannerkorpi, Eva Kosek, Bijar Ghafouri. Increased Anandamide and Decreased Pain and Depression after Exercise in Fibromyalgia. Medicine and science in sports and exercise. 2020 07; 52(7):1617-1628. doi: 10.1249/mss.0000000000002293. [PMID: 32168104]
  • Lea Tischmann, Mathijs Drummen, Peter J Joris, Blandine Gatta-Cherifi, Anne Raben, Mikael Fogelholm, Isabelle Matias, Daniela Cota, Ronald P Mensink, Margriet S Westerterp-Plantenga, Tanja C Adam. Effects of a High-Protein Diet on Cardiometabolic Health, Vascular Function, and Endocannabinoids-A PREVIEW Study. Nutrients. 2020 May; 12(5):. doi: 10.3390/nu12051512. [PMID: 32455987]
  • Jing Wang, Xiaohua Zhang, Chongmei Yang, Shulei Zhao. Effect of monoacylglycerol lipase inhibition on intestinal permeability in chronic stress model. Biochemical and biophysical research communications. 2020 05; 525(4):962-967. doi: 10.1016/j.bbrc.2020.02.173. [PMID: 32173532]
  • Dorian Forte, Flaminia Fanelli, Marco Mezzullo, Martina Barone, Giulia Corradi, Giuseppe Auteri, Daniela Bartoletti, Marina Martello, Emanuela Ottaviani, Carolina Terragna, Antonio Curti, Uberto Pagotto, Francesca Palandri, Michele Cavo, Lucia Catani. Disease-Specific Derangement of Circulating Endocannabinoids and N-Acylethanolamines in Myeloproliferative Neoplasms. International journal of molecular sciences. 2020 May; 21(9):. doi: 10.3390/ijms21093399. [PMID: 32403407]
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  • Björn Kuhla, Volkhard Kaever, Armin Tuchscherer, Angela Kuhla. Involvement of Plasma Endocannabinoids and the Hypothalamic Endocannabinoid System in Increasing Feed Intake after Parturition of Dairy Cows. Neuroendocrinology. 2020; 110(3-4):246-257. doi: 10.1159/000501208. [PMID: 31141804]
  • Vinicius R Acquaro Junior, Germán Augusto Goméz-Ríos, Marcos Tascon, Maria Eugênia Costa Queiroz, Janusz Pawliszyn. Analysis of endocannabinoids in plasma samples by biocompatible solid-phase microextraction devices coupled to mass spectrometry. Analytica chimica acta. 2019 Dec; 1091(?):135-145. doi: 10.1016/j.aca.2019.09.002. [PMID: 31679567]
  • Patrick Heilman, Matthew N Hill, Mary Coussons-Read, Lena Brundin, Emil F Coccaro. Role of the kynurenine pathway and the endocannabinoid system as modulators of inflammation and personality traits. Psychoneuroendocrinology. 2019 12; 110(?):104434. doi: 10.1016/j.psyneuen.2019.104434. [PMID: 31525567]
  • Stefano Vanni, Laura Riccardi, Giulia Palermo, Marco De Vivo. Structure and Dynamics of the Acyl Chains in the Membrane Trafficking and Enzymatic Processing of Lipids. Accounts of chemical research. 2019 11; 52(11):3087-3096. doi: 10.1021/acs.accounts.9b00134. [PMID: 31364837]
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  • Aurélien Laguerre, Sebastian Hauke, Jian Qiu, Martin J Kelly, Carsten Schultz. Photorelease of 2-Arachidonoylglycerol in Live Cells. Journal of the American Chemical Society. 2019 10; 141(42):16544-16547. doi: 10.1021/jacs.9b05978. [PMID: 31560527]
  • Amanda J Page, George Hatzinikolas, Andrew D Vincent, Paul Cavuoto, Gary A Wittert. The TRPV1 channel regulates glucose metabolism. American journal of physiology. Endocrinology and metabolism. 2019 10; 317(4):E667-E676. doi: 10.1152/ajpendo.00102.2019. [PMID: 31408376]
  • Julia Fernández de Luco, Gastón Prez, Bruno Hernández Cravero, Diego de Mendoza, Guillermo R Labadie. Synthesis of a Deuterated Standard for the Quantification of 2-Arachidonoylglycerol in Caenorhabditis elegans. Journal of visualized experiments : JoVE. 2019 09; ?(151):. doi: 10.3791/59882. [PMID: 31589209]
  • Jacob D Meyer, Kevin M Crombie, Dane B Cook, Cecilia J Hillard, Kelli F Koltyn. Serum Endocannabinoid and Mood Changes after Exercise in Major Depressive Disorder. Medicine and science in sports and exercise. 2019 09; 51(9):1909-1917. doi: 10.1249/mss.0000000000002006. [PMID: 30973483]
  • Myungsun Shin, Andrew Buckner, Jessica Prince, Timothy N J Bullock, Ku-Lung Hsu. Diacylglycerol Lipase-β Is Required for TNF-α Response but Not CD8+ T Cell Priming Capacity of Dendritic Cells. Cell chemical biology. 2019 07; 26(7):1036-1041.e3. doi: 10.1016/j.chembiol.2019.04.002. [PMID: 31105063]
  • Chongyang Qiu, Lei Yang, Botao Wang, Lihua Cui, Caixia Li, Yuzhen Zhuo, Lanqiu Zhang, Shukun Zhang, Qi Zhang, Ximo Wang. The role of 2-arachidonoylglycerol in the regulation of the tumor-immune microenvironment in murine models of pancreatic cancer. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Jul; 115(?):108952. doi: 10.1016/j.biopha.2019.108952. [PMID: 31078044]
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