N-Arachidonoyl Glycine (BioDeep_00000171197)
human metabolite
代谢物信息卡片
化学式: C22H35NO3 (361.26168000000007)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCC(O)=O
InChI: InChI=1S/C22H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(24)23-20-22(25)26/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-20H2,1H3,(H,23,24)(H,25,26)
描述信息
N-arachidonoyl glycine belongs to the class of compounds known as N-acylamides. These are molecules characterized by a fatty acyl group linked to a primary amine by an amide bond. More specifically, it is an Arachidonic acid amide of Glycine. It is believed that there are more than 800 types of N-acylamides in the human body. N-acylamides fall into several categories: amino acid conjugates (e.g., those acyl amides conjugated with amino acids), neurotransmitter conjugates (e.g., those acylamides conjugated with neurotransmitters), ethanolamine conjugates (e.g., those acylamides conjugated to ethanolamine), and taurine conjugates (e.g., those acyamides conjugated to taurine). N-Arachidonoyl Glycine is an amino acid conjugate. N-acylamides can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain N-acylamides; 2) medium-chain N-acylamides; 3) long-chain N-acylamides; and 4) very long-chain N-acylamides; 5) hydroxy N-acylamides; 6) branched chain N-acylamides; 7) unsaturated N-acylamides; 8) dicarboxylic N-acylamides and 9) miscellaneous N-acylamides. N-Arachidonoyl Glycine is therefore classified as a long chain N-acylamide. N-acyl amides have a variety of signaling functions in physiology, including in cardiovascular activity, metabolic homeostasis, memory, cognition, pain, motor control and others (PMID: 15655504). N-acyl amides have also been shown to play a role in cell migration, inflammation and certain pathological conditions such as diabetes, cancer, neurodegenerative disease, and obesity (PMID: 23144998; PMID: 25136293; PMID: 28854168).N-acyl amides can be synthesized both endogenously and by gut microbiota (PMID: 28854168). N-acylamides can be biosynthesized via different routes, depending on the parent amine group. N-acyl ethanolamines (NAEs) are formed via the hydrolysis of an unusual phospholipid precursor, N-acyl-phosphatidylethanolamine (NAPE), by a specific phospholipase D. N-acyl amino acids are synthesized via a circulating peptidase M20 domain containing 1 (PM20D1), which can catalyze the bidirectional the condensation and hydrolysis of a variety of N-acyl amino acids. The degradation of N-acylamides is largely mediated by an enzyme called fatty acid amide hydrolase (FAAH), which catalyzes the hydrolysis of N-acylamides into fatty acids and the biogenic amines. Many N-acylamides are involved in lipid signaling system through interactions with transient receptor potential channels (TRP). TRP channel proteins interact with N-acyl amides such as N-arachidonoyl ethanolamide (Anandamide), N-arachidonoyl dopamine and others in an opportunistic fashion (PMID: 23178153). This signaling system has been shown to play a role in the physiological processes involved in inflammation (PMID: 25136293). Other N-acyl amides, including N-oleoyl-glutamine, have also been characterized as TRP channel antagonists (PMID: 29967167). N-acylamides have also been shown to have G-protein-coupled receptors (GPCRs) binding activity (PMID: 28854168). The study of N-acylamides is an active area of research and it is likely that many novel N-acylamides will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.
A human metabolite taken as a putative food compound of mammalian origin [HMDB]
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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
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
- Douglas McHugh, Jeremy Page, Emily Dunn, Heather B Bradshaw. Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells.
British journal of pharmacology.
2012 Apr; 165(8):2414-24. doi:
10.1111/j.1476-5381.2011.01497.x
. [PMID: 21595653] - Sumner H Burstein, Catherine A McQuain, Alonzo H Ross, Rebecca A Salmonsen, Robert E Zurier. Resolution of inflammation by N-arachidonoylglycine.
Journal of cellular biochemistry.
2011 Nov; 112(11):3227-33. doi:
10.1002/jcb.23245
. [PMID: 21732409] - Hyo-Jin Jeong, Robert J Vandenberg, Christopher W Vaughan. N-arachidonyl-glycine modulates synaptic transmission in superficial dorsal horn.
British journal of pharmacology.
2010 Oct; 161(4):925-35. doi:
10.1111/j.1476-5381.2010.00935.x
. [PMID: 20860669] - Gabor Tigyi. Aiming drug discovery at lysophosphatidic acid targets.
British journal of pharmacology.
2010 Sep; 161(2):241-70. doi:
10.1111/j.1476-5381.2010.00815.x
. [PMID: 20735414] - Neelam Parmar, W-S Vanessa Ho. N-arachidonoyl glycine, an endogenous lipid that acts as a vasorelaxant via nitric oxide and large conductance calcium-activated potassium channels.
British journal of pharmacology.
2010 Jun; 160(3):594-603. doi:
10.1111/j.1476-5381.2009.00622.x
. [PMID: 20136843] - Douglas McHugh, Sherry S J Hu, Neta Rimmerman, Ana Juknat, Zvi Vogel, J Michael Walker, Heather B Bradshaw. N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor.
BMC neuroscience.
2010 Mar; 11(?):44. doi:
10.1186/1471-2202-11-44
. [PMID: 20346144] - Bo Tan, David K O'Dell, Y William Yu, M Francesca Monn, H Velocity Hughes, Sumner Burstein, J Michael Walker. Identification of endogenous acyl amino acids based on a targeted lipidomics approach.
Journal of lipid research.
2010 Jan; 51(1):112-9. doi:
10.1194/jlr.m900198-jlr200
. [PMID: 19584404] - Amelia R Edington, Audra A McKinzie, Aaron J Reynolds, Michael Kassiou, Renae M Ryan, Robert J Vandenberg. Extracellular loops 2 and 4 of GLYT2 are required for N-arachidonylglycine inhibition of glycine transport.
The Journal of biological chemistry.
2009 Dec; 284(52):36424-36430. doi:
10.1074/jbc.m109.017509
. [PMID: 19875446] - Jeffrey M McCue, William J Driscoll, Gregory P Mueller. In vitro synthesis of arachidonoyl amino acids by cytochrome c.
Prostaglandins & other lipid mediators.
2009 Nov; 90(1-2):42-8. doi:
10.1016/j.prostaglandins.2009.08.001
. [PMID: 19683594] - Heather B Bradshaw, Sung Ha Lee, Douglas McHugh. Orphan endogenous lipids and orphan GPCRs: a good match.
Prostaglandins & other lipid mediators.
2009 Sep; 89(3-4):131-4. doi:
10.1016/j.prostaglandins.2009.04.006
. [PMID: 19379823] - Jesica R Williams, Anna L Khandoga, Pankaj Goyal, James I Fells, Donna H Perygin, Wolfgang Siess, Abby L Parrill, Gabor Tigyi, Yuko Fujiwara. Unique ligand selectivity of the GPR92/LPA5 lysophosphatidate receptor indicates role in human platelet activation.
The Journal of biological chemistry.
2009 Jun; 284(25):17304-17319. doi:
10.1074/jbc.m109.003194
. [PMID: 19366702] - Heather B Bradshaw, Neta Rimmerman, Sherry Shu-Jung Hu, Valery M Benton, Jordyn M Stuart, Kim Masuda, Benjamin F Cravatt, David K O'Dell, J Michael Walker. The endocannabinoid anandamide is a precursor for the signaling lipid N-arachidonoyl glycine by two distinct pathways.
BMC biochemistry.
2009 May; 10(?):14. doi:
10.1186/1471-2091-10-14
. [PMID: 19460156] - Halikhedkar Aneetha, David K O'Dell, Bo Tan, J Michael Walker, Thomas D Hurley. Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: synthesis of N-acyl glycinals.
Bioorganic & medicinal chemistry letters.
2009 Jan; 19(1):237-41. doi:
10.1016/j.bmcl.2008.10.087
. [PMID: 19013794] - Heather B Bradshaw, Neta Rimmerman, Sherry S-J Hu, Sumner Burstein, J Michael Walker. Novel endogenous N-acyl glycines identification and characterization.
Vitamins and hormones.
2009; 81(?):191-205. doi:
10.1016/s0083-6729(09)81008-x
. [PMID: 19647113] - Yin Duan, Jian Zheng, Russell A Nicholson. Inhibition of [3H]batrachotoxinin A-20alpha-benzoate binding to sodium channels and sodium channel function by endocannabinoids.
Neurochemistry international.
2008 Feb; 52(3):438-46. doi:
10.1016/j.neuint.2007.08.004
. [PMID: 17888543] - Masashi Kohno, Hitoshi Hasegawa, Atsushi Inoue, Masatake Muraoka, Tatsuhiko Miyazaki, Keizo Oka, Masaki Yasukawa. Identification of N-arachidonylglycine as the endogenous ligand for orphan G-protein-coupled receptor GPR18.
Biochemical and biophysical research communications.
2006 Sep; 347(3):827-32. doi:
10.1016/j.bbrc.2006.06.175
. [PMID: 16844083] - Heather B Bradshaw, Neta Rimmerman, Jocelyn F Krey, J Michael Walker. Sex and hormonal cycle differences in rat brain levels of pain-related cannabimimetic lipid mediators.
American journal of physiology. Regulatory, integrative and comparative physiology.
2006 Aug; 291(2):R349-58. doi:
10.1152/ajpregu.00933.2005
. [PMID: 16556899] - J W Aiken, R R Gorman, R J Shebuski. Prevention of blockage of partially obstructed coronary arteries with prostacyclin correlates with inhibition of platelet aggregation.
Prostaglandins.
1979 Apr; 17(4):483-94. doi:
10.1016/0090-6980(79)90001-7
. [PMID: 111306] - J Watkins, A Padfield, J D Alderson. Underlying immunopathology as a cause of adverse responses to two intravenous anaesthetic agents.
British medical journal.
1978 May; 1(6121):1180-1. doi:
10.1136/bmj.1.6121.1180
. [PMID: 638678]