NA 28:8;O2 (BioDeep_00000003097)

   


代谢物信息卡片


(5Z,8Z,11Z,14Z)-N-(3,4-dihydroxyphenethyl)icosa-5,8,11,14-tetraenamide

化学式: C28H41NO3 (439.3086276)
中文名称: N-花生四烯酰多巴胺
谱图信息: 最多检出来源 Mentha canadensis(plant) 83.33%

分子结构信息

SMILES: C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCCC(=O)NCC1C=C(OC)C(O)=CC=1
InChI: InChI=1S/C28H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-28(31)29-24-25-21-22-26(30)27(23-25)32-2/h7-8,10-11,13-14,16-17,21-23,30H,3-6,9,12,15,18-20,24H2,1-2H3,(H,29,31)/b8-7-,11-10-,14-13-,17-16-

描述信息

同义名列表

11 个代谢物同义名

N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-dopamine; N-arachidonoyl dopamine; N-Arachidonyldopamine; Arachidonoyl dopamine; NA 28:8;O2; NADA; N-(5Z,8Z,11Z,15Z-eicosatetraenoyl)-vanillylamine; N-arachidonoyl vanillylamine; NAVA; (5Z,8Z,11Z,14Z)-N-(3,4-dihydroxyphenethyl)icosa-5,8,11,14-tetraenamide; N-Arachidonoyldopamine



数据库引用编号

12 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 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

  • Jérémie Joffre, Che-Chung Yeh, Erika Wong, Mayuri Thete, Fengyun Xu, Ivana Zlatanova, Elliot Lloyd, Lester Kobzik, Matthieu Legrand, Judith Hellman. Activation of CB1R Promotes Lipopolysaccharide-Induced IL-10 Secretion by Monocytic Myeloid-Derived Suppressive Cells and Reduces Acute Inflammation and Organ Injury. Journal of immunology (Baltimore, Md. : 1950). 2020 06; 204(12):3339-3350. doi: 10.4049/jimmunol.2000213. [PMID: 32385136]
  • Samira K Lawton, Fengyun Xu, Alphonso Tran, Erika Wong, Arun Prakash, Mark Schumacher, Judith Hellman, Kevin Wilhelmsen. N-Arachidonoyl Dopamine Modulates Acute Systemic Inflammation via Nonhematopoietic TRPV1. Journal of immunology (Baltimore, Md. : 1950). 2017 08; 199(4):1465-1475. doi: 10.4049/jimmunol.1602151. [PMID: 28701511]
  • Tomoyo Yoshinaga, Kenichiro Uwabe, Shoichi Naito, Kenichi Higashino, Toru Nakano, Yoshito Numata, Akio Kihara. AM251 Suppresses Epithelial-Mesenchymal Transition of Renal Tubular Epithelial Cells. PloS one. 2016; 11(12):e0167848. doi: 10.1371/journal.pone.0167848. [PMID: 27936102]
  • Safa Y Almaghrabi, Dominic P Geraghty, Kiran D K Ahuja, Murray J Adams. Vanilloid-like agents inhibit aggregation of human platelets. Thrombosis research. 2014 Aug; 134(2):412-7. doi: 10.1016/j.thromres.2014.05.038. [PMID: 24953906]
  • Jessica A Fawley, Mackenzie E Hofmann, Michael C Andresen. Cannabinoid 1 and transient receptor potential vanilloid 1 receptors discretely modulate evoked glutamate separately from spontaneous glutamate transmission. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2014 Jun; 34(24):8324-32. doi: 10.1523/jneurosci.0315-14.2014. [PMID: 24920635]
  • Magali Cazade, Cindy E Nuss, Isabelle Bidaud, John J Renger, Victor N Uebele, Philippe Lory, Jean Chemin. Cross-modulation and molecular interaction at the Cav3.3 protein between the endogenous lipids and the T-type calcium channel antagonist TTA-A2. Molecular pharmacology. 2014 Feb; 85(2):218-25. doi: 10.1124/mol.113.089581. [PMID: 24214826]
  • Vincenzo Di Marzo, Luciano De Petrocellis. Why do cannabinoid receptors have more than one endogenous ligand?. Philosophical transactions of the Royal Society of London. Series B, Biological sciences. 2012 Dec; 367(1607):3216-28. doi: 10.1098/rstb.2011.0382. [PMID: 23108541]
  • Y A Mahmmoud, M Gaster. Uncoupling of sarcoplasmic reticulum Ca²⁺-ATPase by N-arachidonoyl dopamine. Members of the endocannabinoid family as thermogenic drugs. British journal of pharmacology. 2012 Aug; 166(7):2060-9. doi: 10.1111/j.1476-5381.2012.01899.x. [PMID: 22335600]
  • Alexandra Wojtalla, Frank Herweck, Michaela Granzow, Sabine Klein, Jonel Trebicka, Sebastian Huss, Raissa Lerner, Beat Lutz, Frank Alexander Schildberg, Percy Alexander Knolle, Tilman Sauerbruch, Manfred Vincenz Singer, Andreas Zimmer, Sören Volker Siegmund. The endocannabinoid N-arachidonoyl dopamine (NADA) selectively induces oxidative stress-mediated cell death in hepatic stellate cells but not in hepatocytes. American journal of physiology. Gastrointestinal and liver physiology. 2012 Apr; 302(8):G873-87. doi: 10.1152/ajpgi.00241.2011. [PMID: 22301114]
  • Koppany Visnyei, Hideyuki Onodera, Robert Damoiseaux, Kuniyasu Saigusa, Syuzanna Petrosyan, David De Vries, Denise Ferrari, Jonathan Saxe, Eduard H Panosyan, Michael Masterman-Smith, Jack Mottahedeh, Kenneth A Bradley, Jing Huang, Chiara Sabatti, Ichiro Nakano, Harley I Kornblum. A molecular screening approach to identify and characterize inhibitors of glioblastoma stem cells. Molecular cancer therapeutics. 2011 Oct; 10(10):1818-28. doi: 10.1158/1535-7163.mct-11-0268. [PMID: 21859839]
  • Carmen M Navarrete, Moisés Pérez, Amaya García de Vinuesa, Juan A Collado, Bernd L Fiebich, Marco A Calzado, Eduardo Muñoz. Endogenous N-acyl-dopamines induce COX-2 expression in brain endothelial cells by stabilizing mRNA through a p38 dependent pathway. Biochemical pharmacology. 2010 Jun; 79(12):1805-14. doi: 10.1016/j.bcp.2010.02.014. [PMID: 20206142]
  • 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]
  • V Di Marzo, L De Petrocellis. Endocannabinoids as regulators of transient receptor potential (TRP) channels: A further opportunity to develop new endocannabinoid-based therapeutic drugs. Current medicinal chemistry. 2010; 17(14):1430-49. doi: 10.2174/092986710790980078. [PMID: 20166923]
  • 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]
  • Cassandra I Saunders, Robert G Fassett, Dominic P Geraghty. Up-regulation of TRPV1 in mononuclear cells of end-stage kidney disease patients increases susceptibility to N-arachidonoyl-dopamine (NADA)-induced cell death. Biochimica et biophysica acta. 2009 Oct; 1792(10):1019-26. doi: 10.1016/j.bbadis.2009.07.008. [PMID: 19619644]
  • Sherry Shu-Jung Hu, Heather B Bradshaw, Valery M Benton, Jay Shih-Chieh Chen, Susan M Huang, Alberto Minassi, Tiziana Bisogno, Kim Masuda, Bo Tan, Robert Roskoski, Benjamin F Cravatt, Vincenzo Di Marzo, J Michael Walker. The biosynthesis of N-arachidonoyl dopamine (NADA), a putative endocannabinoid and endovanilloid, via conjugation of arachidonic acid with dopamine. Prostaglandins, leukotrienes, and essential fatty acids. 2009 Oct; 81(4):291-301. doi: 10.1016/j.plefa.2009.05.026. [PMID: 19570666]
  • Aurélien Thomas, Gérard Hopfgartner, Christian Giroud, Christian Staub. Quantitative and qualitative profiling of endocannabinoids in human plasma using a triple quadrupole linear ion trap mass spectrometer with liquid chromatography. Rapid communications in mass spectrometry : RCM. 2009 Mar; 23(5):629-38. doi: 10.1002/rcm.3918. [PMID: 19170046]
  • N Rimmerman, H B Bradshaw, A Basnet, B Tan, Theodore S Widlanski, J M Walker. Microsomal omega-hydroxylated metabolites of N-arachidonoyl dopamine are active at recombinant human TRPV1 receptors. Prostaglandins & other lipid mediators. 2009 Jan; 88(1-2):10-7. doi: 10.1016/j.prostaglandins.2008.08.004. [PMID: 18812233]
  • Enza Palazzo, Francesco Rossi, Sabatino Maione. Role of TRPV1 receptors in descending modulation of pain. Molecular and cellular endocrinology. 2008 Apr; 286(1-2 Suppl 1):S79-83. doi: 10.1016/j.mce.2008.01.013. [PMID: 18325659]
  • 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]
  • Mikhail Yu Bobrov, Anatoly A Lizhin, Ekaterina L Andrianova, Natalia M Gretskaya, Lidia E Frumkina, Leonid G Khaspekov, Vladimir V Bezuglov. Antioxidant and neuroprotective properties of N-arachidonoyldopamine. Neuroscience letters. 2008 Jan; 431(1):6-11. doi: 10.1016/j.neulet.2007.11.010. [PMID: 18069125]
  • Youping Wang, Donna H Wang. Increased depressor response to N-arachidonoyl-dopamine during high salt intake: role of the TRPV1 receptor. Journal of hypertension. 2007 Dec; 25(12):2426-33. doi: 10.1097/hjh.0b013e3282efd1bf. [PMID: 17984664]
  • S E O'Sullivan. Cannabinoids go nuclear: evidence for activation of peroxisome proliferator-activated receptors. British journal of pharmacology. 2007 Nov; 152(5):576-82. doi: 10.1038/sj.bjp.0707423. [PMID: 17704824]
  • 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]
  • Bo Tan, Heather B Bradshaw, Neta Rimmerman, Harini Srinivasan, Y William Yu, Jocelyn F Krey, M Francesca Monn, Jay Shih-Chieh Chen, Sherry Shu-Jung Hu, Sarah R Pickens, J Michael Walker. Targeted lipidomics: discovery of new fatty acyl amides. The AAPS journal. 2006 Jul; 8(3):E461-5. doi: 10.1208/aapsj080354. [PMID: 17025263]
  • 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]
  • J Michael Walker, Jocelyn F Krey, Jay S Chen, Eivind Vefring, Jan A Jahnsen, Heather Bradshaw, Susan M Huang. Targeted lipidomics: fatty acid amides and pain modulation. Prostaglandins & other lipid mediators. 2005 Sep; 77(1-4):35-45. doi: 10.1016/j.prostaglandins.2004.09.017. [PMID: 16099389]
  • Prisca Honore, Carol T Wismer, Joe Mikusa, Chang Z Zhu, Chengmin Zhong, Donna M Gauvin, Arthur Gomtsyan, Rachid El Kouhen, Chih-Hung Lee, Kennan Marsh, James P Sullivan, Connie R Faltynek, Michael F Jarvis. A-425619 [1-isoquinolin-5-yl-3-(4-trifluoromethyl-benzyl)-urea], a novel transient receptor potential type V1 receptor antagonist, relieves pathophysiological pain associated with inflammation and tissue injury in rats. The Journal of pharmacology and experimental therapeutics. 2005 Jul; 314(1):410-21. doi: 10.1124/jpet.105.083915. [PMID: 15837818]
  • Luciano De Petrocellis, Constance J Chu, Aniello Schiano Moriello, Juliane C Kellner, J Michael Walker, Vincenzo Di Marzo. Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels. British journal of pharmacology. 2004 Sep; 143(2):251-6. doi: 10.1038/sj.bjp.0705924. [PMID: 15289293]
  • Constance J Chu, Susan M Huang, Luciano De Petrocellis, Tiziana Bisogno, Scott A Ewing, Jeffrey D Miller, Robert E Zipkin, Nives Daddario, Giovanni Appendino, Vincenzo Di Marzo, J Michael Walker. N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia. The Journal of biological chemistry. 2003 Apr; 278(16):13633-9. doi: 10.1074/jbc.m211231200. [PMID: 12569099]
  • Songbai Zhang, Akihiro Mizutani, Chihiro Hisatsune, Takayasu Higo, Hiroko Bannai, Tomohiro Nakayama, Mitsuharu Hattori, Katsuhiko Mikoshiba. Protein 4.1N is required for translocation of inositol 1,4,5-trisphosphate receptor type 1 to the basolateral membrane domain in polarized Madin-Darby canine kidney cells. The Journal of biological chemistry. 2003 Feb; 278(6):4048-56. doi: 10.1074/jbc.m209960200. [PMID: 12444087]