2-Arachidonyl Glycerol ether (BioDeep_00000027043)

   

human metabolite Endogenous


代谢物信息卡片


2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yloxy]propane-1,3-diol

化学式: C23H40O3 (364.2977)
中文名称:
谱图信息: 最多检出来源 Mus musculus(not specific) 0.8%

分子结构信息

SMILES: CCCCCC=CCC=CCC=CCC=CCCCCOC(CO)CO
InChI: InChI=1S/C23H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-23(21-24)22-25/h6-7,9-10,12-13,15-16,23-25H,2-5,8,11,14,17-22H2,1H3/b7-6-,10-9-,13-12-,16-15-

描述信息

2-Arachidonyl glycerol ether (2-AG ether) has been isolated from porcine brain and its structure determined by mass spec analysis.1 2-AG ether has also been synthesized as an analog of the endogenous cannabinoid (CB), 2-AG, for structure activity testing.2 2-AG ether is a selective central cannabinoid (CB1) receptor agonist exhibiting Ki values of 21.2 nM and >3 ?M at the CB1 and peripheral cannabinoid (CB2) receptors, respectively, and displays the typical tetrad of CB activities in mice.1 It is much more chemically stable than 2-AG, with an endogenous half-life of hours rather than minutes.3 However, it is at least 10-fold less potent than 2-AG in eliciting typical CB1-mediated responses.2 2-AG ether elicits modest reductions in IOP in rabbits when administered at doses exceeding 50 ?g per eye.3 2-AG ether increases aqueous humor outflow via the CB1 receptor in the trabecular meshwork. [HMDB]
2-Arachidonyl glycerol ether (2-AG ether) has been isolated from porcine brain and its structure determined by mass spec analysis.1 2-AG ether has also been synthesized as an analog of the endogenous cannabinoid (CB), 2-AG, for structure activity testing.2 2-AG ether is a selective central cannabinoid (CB1) receptor agonist exhibiting Ki values of 21.2 nM and >3 µM at the CB1 and peripheral cannabinoid (CB2) receptors, respectively, and displays the typical tetrad of CB activities in mice.1 It is much more chemically stable than 2-AG, with an endogenous half-life of hours rather than minutes.3 However, it is at least 10-fold less potent than 2-AG in eliciting typical CB1-mediated responses.2 2-AG ether elicits modest reductions in IOP in rabbits when administered at doses exceeding 50 µg per eye.3 2-AG ether increases aqueous humor outflow via the CB1 receptor in the trabecular meshwork.

同义名列表

14 个代谢物同义名

2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yloxy]propane-1,3-diol; (5Z,8Z,11Z,14Z)-Icosatetraenyl-2-glyceryl ether; 2-AG ether;2-Arachidonylglyceryl ether;HU 310; 2-(5Z,8Z,11Z,14Z-Eicosatetraenyl)-sn-glycerol; 5Z,8Z,11Z,14Z-eicosatetraen-2-glyceryl ether; 2-O-(5Z,8Z,11Z,14Z)-Eicosatetraenylglycerol; 2-Arachidonyl Glycerol ether; 2-Arachidonyl glyceryl ether; 2-Arachidonyl-glycerol; 2-Arachidonylglycerol; Noladin Ether; 2-AG ether; Noladin; HU-310



数据库引用编号

10 个数据库交叉引用编号

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代谢反应

0 个相关的代谢反应过程信息。

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1 个相关的物种来源信息

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亚细胞结构定位 关联基因列表


文献列表

  • Yaochen Zhang, Don-Kyu Kim, Ji-Min Lee, Seung Bum Park, Won-Il Jeong, Seong Heon Kim, In-Kyu Lee, Chul-Ho Lee, John Y L Chiang, Hueng-Sik Choi. Orphan nuclear receptor oestrogen-related receptor γ (ERRγ) plays a key role in hepatic cannabinoid receptor type 1-mediated induction of CYP7A1 gene expression. The Biochemical journal. 2015 Sep; 470(2):181-93. doi: 10.1042/bj20141494. [PMID: 26348907]
  • Takahiro Shimizu, Kenjiro Tanaka, Kunihiko Yokotani. Stimulatory and inhibitory roles of brain 2-arachidonoylglycerol in bombesin-induced central activation of adrenomedullary outflow in rats. Journal of pharmacological sciences. 2013; 121(2):157-71. doi: 10.1254/jphs.12208fp. [PMID: 23386378]
  • Antonella Brizzi, Maria Grazia Cascio, Maria Frosini, Alessia Ligresti, Francesca Aiello, Irene Biotti, Vittorio Brizzi, Roger Guy Pertwee, Federico Corelli, Vincenzo Di Marzo. Resorcinol-sn-glycerol derivatives: novel 2-arachidonoylglycerol mimetics endowed with high affinity and selectivity for cannabinoid type 1 receptor. Journal of medicinal chemistry. 2011 Dec; 54(24):8278-88. doi: 10.1021/jm200529h. [PMID: 22044209]
  • Kasem Nithipatikom, Marilyn A Isbell, Michael P Endsley, Jeffrey E Woodliff, William B Campbell. Anti-proliferative effect of a putative endocannabinoid, 2-arachidonylglyceryl ether in prostate carcinoma cells. Prostaglandins & other lipid mediators. 2011 Feb; 94(1-2):34-43. doi: 10.1016/j.prostaglandins.2010.12.002. [PMID: 21167293]
  • R Jumpertz, T Wiesner, M Blüher, S Engeli, S Bátkai, H Wirtz, A Bosse-Henck, M Stumvoll. Circulating endocannabinoids and N-acyl-ethanolamides in patients with sleep apnea--specific role of oleoylethanolamide. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2010 Oct; 118(9):591-5. doi: 10.1055/s-0030-1253344. [PMID: 20429051]
  • Patrick Maison, Deborah J Walker, Frank S Walsh, Gareth Williams, Patrick Doherty. BDNF regulates neuronal sensitivity to endocannabinoids. Neuroscience letters. 2009 Dec; 467(2):90-4. doi: 10.1016/j.neulet.2009.10.011. [PMID: 19818836]
  • W-S V Ho, M D Randall. Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol. British journal of pharmacology. 2007 Mar; 150(5):641-51. doi: 10.1038/sj.bjp.0707141. [PMID: 17245358]
  • Rocío Sancho, Laureano de la Vega, Antonio Macho, Giovanni Appendino, Vincenzo Di Marzo, Eduardo Muñoz. Mechanisms of HIV-1 inhibition by the lipid mediator N-arachidonoyldopamine. Journal of immunology (Baltimore, Md. : 1950). 2005 Sep; 175(6):3990-9. doi: 10.4049/jimmunol.175.6.3990. [PMID: 16148147]
  • Laurent Venance, Raphael Maldonado, Olivier Manzoni. [Endocannabinoids in the central nervous system]. Medecine sciences : M/S. 2004 Jan; 20(1):45-53. doi: 10.1051/medsci/200420145. [PMID: 14770363]