MG(0:0/18:1(9Z)/0:0) (BioDeep_00000021456)

 

Secondary id: BioDeep_00000631442

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


1,3-dihydroxypropan-2-yl (9Z)-octadec-9-enoate

化学式: C21H40O4 (356.29264400000005)
中文名称: 2-十八烯酸单甘油酯
谱图信息: 最多检出来源 Viridiplantae(plant) 55.56%

分子结构信息

SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)CO
InChI: InChI=1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-

描述信息

1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed alpha-monoacylglycerols, while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well.; MG(0:0/18:1(9Z)/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups.
MG(0:0/18:1(9Z)/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed alpha-monoacylglycerols, while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well.

同义名列表

30 个代谢物同义名

1,3-dihydroxypropan-2-yl (9Z)-octadec-9-enoate; 1,3-Dihydroxypropan-2-yl oleic acid; 2-(9Z-Octadecenoyl)-rac-glycerol; 1,3-dihydroxypropan-2-yl oleate; 2-(9Z-Octadecenoyl)-glycerol; 2-Glyceryl monooleic acid; 2-Oleyl glycerol ether; 2-Glyceryl monooleate; beta-Monoacylglycerol; 2-Monooleoylglycerol; MG(0:0/18:1(9Z)/0:0); Glyceryl monooleate; 1-Monoacylglyceride; b-Monoacylglycerol; 1-Monoacylglycerol; 2-oleoyl-glycerol; 2-Oleoylglycerol; MAG(0:0/18:1W9); MAG(0:0/18:1n9); UNII-9a2389K694; MG(0:0/18:1W9); MG(0:0/18:1n9); MAG(0:0/18:1); 2-mono-C18:1; MG(0:0/18:1); 2-monoolein; 2-OG lipid; MAG(18:1); MG(18:1); 2-OG



数据库引用编号

11 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

150 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(4)

COVID-19 Disease Map(0)

PathBank(144)

PharmGKB(0)

21 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

  • Mohammad Bashashati, Emma Leishman, Heather Bradshaw, Solmaz Sigaroodi, Eric Tatro, Tamis Bright, Richard McCallum, Irene Sarosiek. Plasma endocannabinoids and cannabimimetic fatty acid derivatives are altered in gastroparesis: A sex- and subtype-dependent observation. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society. 2021 01; 33(1):e13961. doi: 10.1111/nmo.13961. [PMID: 32779297]
  • Gregory T Carter, Ryan J McLaughlin, Carrie Cuttler, Garrett J Sauber, Douglas L Weeks, Cecilia J Hillard, Michael D Weiss. Endocannabinoids and related lipids in serum from patients with amyotrophic lateral sclerosis. Muscle & nerve. 2021 01; 63(1):120-126. doi: 10.1002/mus.27096. [PMID: 33094490]
  • Christoffer Martinussen, Carsten Dirksen, Kirstine N Bojsen-Møller, Maria S Svane, Elin R Carlsson, Bolette Hartmann, Trine R Clausen, Simon Veedfald, Viggo B Kristiansen, Jens F Rehfeld, Harald S Hansen, Jens J Holst, Sten Madsbad. Intestinal sensing and handling of dietary lipids in gastric bypass-operated patients and matched controls. The American journal of clinical nutrition. 2020 01; 111(1):28-41. doi: 10.1093/ajcn/nqz272. [PMID: 31742316]
  • 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]
  • Avery L McIntosh, Gregory G Martin, Huan Huang, Danilo Landrock, Ann B Kier, Friedhelm Schroeder. Δ9-Tetrahydrocannabinol induces endocannabinoid accumulation in mouse hepatocytes: antagonism by Fabp1 gene ablation. Journal of lipid research. 2018 04; 59(4):646-657. doi: 10.1194/jlr.m082644. [PMID: 29414765]
  • Mette Johannsen Mandøe, Katrine Bagge Hansen, Johanne Agerlin Windeløv, Filip Krag Knop, Jens Frederik Rehfeld, Mette Marie Rosenkilde, Jens Juul Holst, Harald Severin Hansen. Comparing olive oil and C4-dietary oil, a prodrug for the GPR119 agonist, 2-oleoyl glycerol, less energy intake of the latter is needed to stimulate incretin hormone secretion in overweight subjects with type 2 diabetes. Nutrition & diabetes. 2018 01; 8(1):2. doi: 10.1038/s41387-017-0011-z. [PMID: 29330461]
  • Mette J Mandøe, Katrine B Hansen, Bolette Hartmann, Jens F Rehfeld, Jens J Holst, Harald S Hansen. The 2-monoacylglycerol moiety of dietary fat appears to be responsible for the fat-induced release of GLP-1 in humans. The American journal of clinical nutrition. 2015 Sep; 102(3):548-55. doi: 10.3945/ajcn.115.106799. [PMID: 26178726]
  • Karen Kleberg, Louise Lundeman Nielsen, Nicolai Stuhr-Hansen, John Nielsen, Harald Severin Hansen. Evaluation of the immediate vascular stability of lipoprotein lipase-generated 2-monoacylglycerol in mice. BioFactors (Oxford, England). 2014 Nov; 40(6):596-602. doi: 10.1002/biof.1189. [PMID: 25359532]
  • Antoni Pastor, Magí Farré, Montserrat Fitó, Fernando Fernandez-Aranda, Rafael de la Torre. Analysis of ECs and related compounds in plasma: artifactual isomerization and ex vivo enzymatic generation of 2-MGs. Journal of lipid research. 2014 May; 55(5):966-77. doi: 10.1194/jlr.d043794. [PMID: 24610889]
  • Samreen K Syed, Hai Hoang Bui, Lisa S Beavers, Thomas B Farb, James Ficorilli, Amy K Chesterfield, Ming-Shang Kuo, Krister Bokvist, David G Barrett, Alexander M Efanov. Regulation of GPR119 receptor activity with endocannabinoid-like lipids. American journal of physiology. Endocrinology and metabolism. 2012 Dec; 303(12):E1469-78. doi: 10.1152/ajpendo.00269.2012. [PMID: 23074242]
  • Dina Navia-Paldanius, Juha R Savinainen, Jarmo T Laitinen. Biochemical and pharmacological characterization of human α/β-hydrolase domain containing 6 (ABHD6) and 12 (ABHD12). Journal of lipid research. 2012 Nov; 53(11):2413-24. doi: 10.1194/jlr.m030411. [PMID: 22969151]
  • C J Roberts, K L Stuhr, C J Hillard. Swim stress differentially affects limbic contents of 2-arachidonoylglycerol and 2-oleoylglycerol. Neuroscience. 2012 Mar; 204(?):74-82. doi: 10.1016/j.neuroscience.2011.11.065. [PMID: 22192839]
  • Katrine B Hansen, Mette M Rosenkilde, Filip K Knop, Niels Wellner, Thi A Diep, Jens F Rehfeld, Ulrik B Andersen, Jens J Holst, Harald S Hansen. 2-Oleoyl glycerol is a GPR119 agonist and signals GLP-1 release in humans. The Journal of clinical endocrinology and metabolism. 2011 Sep; 96(9):E1409-17. doi: 10.1210/jc.2011-0647. [PMID: 21778222]
  • Sabiqah Tuan Anuar, Carla Villegas, Samuel M Mugo, Jonathan M Curtis. The development of flow-through bio-catalyst microreactors from silica micro structured fibers for lipid transformations. Lipids. 2011 Jun; 46(6):545-55. doi: 10.1007/s11745-010-3522-0. [PMID: 21318469]
  • Arpita Gantayet, Januvi Jegatheswaran, Gowtham Jayakumaran, Matthew K Topham, Richard M Epand. Endocannabinoids and diacylglycerol kinase activity. Biochimica et biophysica acta. 2011 Apr; 1808(4):1050-3. doi: 10.1016/j.bbamem.2010.12.022. [PMID: 21194521]
  • Linda K Vaughn, Gerene Denning, Kara L Stuhr, Harriet de Wit, Matthew N Hill, Cecilia J Hillard. Endocannabinoid signalling: has it got rhythm?. British journal of pharmacology. 2010 Jun; 160(3):530-43. doi: 10.1111/j.1476-5381.2010.00790.x. [PMID: 20590563]
  • Ava Jiangyang Guo, Roy Chi-yan Choi, Anna Wing-han Cheung, Jun Li, Ivy Xiaoying Chen, Tina Tingxia Dong, Karl Wah-keung Tsim, Brad Wing-chuen Lau. Stimulation of Apolipoprotein A-IV expression in Caco-2/TC7 enterocytes and reduction of triglyceride formation in 3T3-L1 adipocytes by potential anti-obesity Chinese herbal medicines. Chinese medicine. 2009 Mar; 4(?):5. doi: 10.1186/1749-8546-4-5. [PMID: 19321011]
  • Olivier Béaslas, Carine Cueille, François Delers, Danielle Chateau, Jean Chambaz, Monique Rousset, Véronique Carrière. Sensing of dietary lipids by enterocytes: a new role for SR-BI/CLA-1. PloS one. 2009; 4(1):e4278. doi: 10.1371/journal.pone.0004278. [PMID: 19169357]
  • Giulio G Muccioli, Geoffray Labar, Didier M Lambert. CAY10499, a novel monoglyceride lipase inhibitor evidenced by an expeditious MGL assay. Chembiochem : a European journal of chemical biology. 2008 Nov; 9(16):2704-10. doi: 10.1002/cbic.200800428. [PMID: 18855964]
  • Séverine Vandevoorde, Christopher J Fowler. Inhibition of fatty acid amide hydrolase and monoacylglycerol lipase by the anandamide uptake inhibitor VDM11: evidence that VDM11 acts as an FAAH substrate. British journal of pharmacology. 2005 Aug; 145(7):885-93. doi: 10.1038/sj.bjp.0706253. [PMID: 15895107]
  • Danielle Chateau, Thomas Pauquai, François Delers, Monique Rousset, Jean Chambaz, Sylvie Demignot. Lipid micelles stimulate the secretion of triglyceride-enriched apolipoprotein B48-containing lipoproteins by Caco-2 cells. Journal of cellular physiology. 2005 Mar; 202(3):767-76. doi: 10.1002/jcp.20173. [PMID: 15389567]
  • Vadim Cherezov, Jeffrey Clogston, Yohann Misquitta, Wissam Abdel-Gawad, Martin Caffrey. Membrane protein crystallization in meso: lipid type-tailoring of the cubic phase. Biophysical journal. 2002 Dec; 83(6):3393-407. doi: 10.1016/s0006-3495(02)75339-3. [PMID: 12496106]
  • M O James, J R Fouts, J R Bend. Hepatic and extrahepatic metabolism, in vitro, of an epoxide (8-(14) C-styrene oxide) in the rabbit. Biochemical pharmacology. 1976 Jan; 25(2):187-93. doi: 10.1016/0006-2952(76)90289-6. [PMID: 4076]
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