N-(4-Hydroxyphenyl)-eicosa-5,8,11,14-tetraenamide (BioDeep_00000175944)

   

human metabolite blood metabolite


代谢物信息卡片


N-(4-Hydroxyphenyl)-eicosa-5,8,11,14-tetraenamide

化学式: C26H37NO2 (395.2824142)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 92.86%

分子结构信息

SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC1=CC=C(O)C=C1
InChI: InChI=1S/C26H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26(29)27-24-20-22-25(28)23-21-24/h6-7,9-10,12-13,15-16,20-23,28H,2-5,8,11,14,17-19H2,1H3,(H,27,29)



数据库引用编号

3 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)

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

  • A Rehfeld, H Frederiksen, R H Rasmussen, A David, J Chaker, B S Nielsen, J E Nielsen, A Juul, N E Skakkebæk, D M Kristensen. Human sperm cells can form paracetamol metabolite AM404 that directly interferes with sperm calcium signalling and function through a CatSper-dependent mechanism. Human reproduction (Oxford, England). 2022 05; 37(5):922-935. doi: 10.1093/humrep/deac042. [PMID: 35259261]
  • Sherif S Abdel Mageed, Ramy M Ammar, Noha N Nassar, Helmy Moawad, Ahmed S Kamel. Role of PI3K/Akt axis in mitigating hippocampal ischemia-reperfusion injury via CB1 receptor stimulation by paracetamol and FAAH inhibitor in rat. Neuropharmacology. 2022 04; 207(?):108935. doi: 10.1016/j.neuropharm.2021.108935. [PMID: 34968475]
  • András Iring, László Hricisák, Zoltán Benyó. CB1 receptor-mediated respiratory depression by endocannabinoids. Respiratory physiology & neurobiology. 2017 06; 240(?):48-52. doi: 10.1016/j.resp.2017.02.011. [PMID: 28254562]
  • Takahiro Shimizu, Kenjiro Tanaka, Shogo Shimizu, Youichirou Higashi, Toshio Yawata, Kumiko Nakamura, Keisuke Taniuchi, Tetsuya Ueba, Kazunari Yuri, Motoaki Saito. Possible inhibitory role of endogenous 2-arachidonoylglycerol as an endocannabinoid in (±)-epibatidine-induced activation of central adrenomedullary outflow in the rat. Neuropharmacology. 2015 Aug; 95(?):278-89. doi: 10.1016/j.neuropharm.2015.03.034. [PMID: 25882827]
  • Francisco J Caballero, Rafael Soler-Torronteras, Maribel Lara-Chica, Victor García, Bernd L Fiebich, Eduardo Muñoz, Marco A Calzado. AM404 inhibits NFAT and NF-κB signaling pathways and impairs migration and invasiveness of neuroblastoma cells. European journal of pharmacology. 2015 Jan; 746(?):221-32. doi: 10.1016/j.ejphar.2014.11.023. [PMID: 25460026]
  • Elizabeth Sabens Liedhegner, Caleb D Vogt, Daniel S Sem, Christopher W Cunningham, Cecilia J Hillard. Sterol carrier protein-2: binding protein for endocannabinoids. Molecular neurobiology. 2014 Aug; 50(1):149-58. doi: 10.1007/s12035-014-8651-7. [PMID: 24510313]
  • David A Barrière, Christophe Mallet, Anders Blomgren, Charlotte Simonsen, Laurence Daulhac, Frédéric Libert, Eric Chapuy, Monique Etienne, Edward D Högestätt, Peter M Zygmunt, Alain Eschalier. Fatty acid amide hydrolase-dependent generation of antinociceptive drug metabolites acting on TRPV1 in the brain. PloS one. 2013; 8(8):e70690. doi: 10.1371/journal.pone.0070690. [PMID: 23940628]
  • Carol A Paronis, Ganesh A Thakur, Shama Bajaj, Spyros P Nikas, V Kiran Vemuri, Alexandros Makriyannis, Jack Bergman. Diuretic effects of cannabinoids. The Journal of pharmacology and experimental therapeutics. 2013 Jan; 344(1):8-14. doi: 10.1124/jpet.112.199331. [PMID: 23019138]
  • András Iring, Éva Ruisanchez, Miriam Leszl-Ishiguro, Béla Horváth, Rita Benkő, Zsombor Lacza, Zoltán Járai, Péter Sándor, Vincenzo Di Marzo, Pál Pacher, Zoltán Benyó. Role of endocannabinoids and cannabinoid-1 receptors in cerebrocortical blood flow regulation. PloS one. 2013; 8(1):e53390. doi: 10.1371/journal.pone.0053390. [PMID: 23308211]
  • Amanda Jabin Fågelskiöld, Kristina Kannisto, Anna Boström, Banina Hadrovic, Cecilia Farre, Mohamed Eweida, Kenneth Wester, Md Shahidul Islam. Insulin-secreting INS-1E cells express functional TRPV1 channels. Islets. 2012 Jan; 4(1):56-63. doi: 10.4161/isl.18915. [PMID: 22274646]
  • Takahiro Shimizu, Lianyi Lu, Kunihiko Yokotani. Endogenously generated 2-arachidonoylglycerol plays an inhibitory role in bombesin-induced activation of central adrenomedullary outflow in rats. European journal of pharmacology. 2011 May; 658(2-3):123-31. doi: 10.1016/j.ejphar.2011.02.023. [PMID: 21371452]
  • Takahiro Shimizu, Lianyi Lu, Kunihiko Yokotani. Possible inhibitory roles of endogenous 2-arachidonoylglycerol during corticotropin-releasing factor-induced activation of central sympatho-adrenomedullary outflow in anesthetized rats. European journal of pharmacology. 2010 Sep; 641(1):54-60. doi: 10.1016/j.ejphar.2010.05.007. [PMID: 20519139]
  • Ali Saber-Tehrani, Nima Naderi, Azadeh Hosseini Najarkolaei, Abbas Haghparast, Fereshteh Motamedi. Cannabinoids and their interactions with diazepam on modulation of serum corticosterone concentration in male mice. Neurochemical research. 2010 Jan; 35(1):60-6. doi: 10.1007/s11064-009-0030-9. [PMID: 19590959]
  • Parisa Hasanein, Nepton Soltani. Effects of the endocannabinoid transport inhibitors AM404 and UCM707 on diabetic neuropathy in rats. Clinical and experimental pharmacology & physiology. 2009 Nov; 36(11):1127-31. doi: 10.1111/j.1440-1681.2009.05197.x. [PMID: 19413593]
  • Dai Li, Ben-Mei Chen, Jun Peng, Yi-Shuai Zhang, Xiao-Hui Li, Qiong Yuan, Chang-Ping Hu, Han-Wu Deng, Yuan-Jian Li. Role of anandamide transporter in regulating calcitonin gene-related peptide production and blood pressure in hypertension. Journal of hypertension. 2009 Jun; 27(6):1224-32. doi: 10.1097/hjh.0b013e328329bbd7. [PMID: 19462497]
  • Michelle Roche, John P Kelly, Maeve O'Driscoll, David P Finn. Augmentation of endogenous cannabinoid tone modulates lipopolysaccharide-induced alterations in circulating cytokine levels in rats. Immunology. 2008 Oct; 125(2):263-71. doi: 10.1111/j.1365-2567.2008.02838.x. [PMID: 18393970]
  • Boris B Gorzalka, Anna C Morrish, Matthew N Hill. Endocannabinoid modulation of male rat sexual behavior. Psychopharmacology. 2008 Jul; 198(4):479-86. doi: 10.1007/s00213-007-0901-1. [PMID: 17694389]
  • Matthew J McFarland, Tamera K Bardell, Marla L Yates, Ekaterina A Placzek, Eric L Barker. RNA interference-mediated knockdown of dynamin 2 reduces endocannabinoid uptake into neuronal dCAD cells. Molecular pharmacology. 2008 Jul; 74(1):101-8. doi: 10.1124/mol.108.044834. [PMID: 18436710]
  • G La Rana, R Russo, G D'Agostino, O Sasso, G Mattace Raso, A Iacono, R Meli, D Piomelli, A Calignano. AM404, an anandamide transport inhibitor, reduces plasma extravasation in a model of neuropathic pain in rat: role for cannabinoid receptors. Neuropharmacology. 2008 Mar; 54(3):521-9. doi: 10.1016/j.neuropharm.2007.10.021. [PMID: 18093621]
  • Moisés García-Arencibia, Sara González, Eva de Lago, José A Ramos, Raphael Mechoulam, Javier Fernández-Ruiz. Evaluation of the neuroprotective effect of cannabinoids in a rat model of Parkinson's disease: importance of antioxidant and cannabinoid receptor-independent properties. Brain research. 2007 Feb; 1134(1):162-70. doi: 10.1016/j.brainres.2006.11.063. [PMID: 17196181]
  • Eleni T Tzavara, Dominic L Li, Larissa Moutsimilli, Tiziana Bisogno, Vincenzo Di Marzo, Lee A Phebus, George G Nomikos, Bruno Giros. Endocannabinoids activate transient receptor potential vanilloid 1 receptors to reduce hyperdopaminergia-related hyperactivity: therapeutic implications. Biological psychiatry. 2006 Mar; 59(6):508-15. doi: 10.1016/j.biopsych.2005.08.019. [PMID: 16199010]
  • Daniel T Brozoski, Caron Dean, Francis A Hopp, Jeanne L Seagard. Uptake blockade of endocannabinoids in the NTS modulates baroreflex-evoked sympathoinhibition. Brain research. 2005 Oct; 1059(2):197-202. doi: 10.1016/j.brainres.2005.08.030. [PMID: 16154548]
  • 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]
  • Murat Oz, Shelley N Jackson, Amina S Woods, Marisela Morales, Li Zhang. Additive effects of endogenous cannabinoid anandamide and ethanol on alpha7-nicotinic acetylcholine receptor-mediated responses in Xenopus Oocytes. The Journal of pharmacology and experimental therapeutics. 2005 Jun; 313(3):1272-80. doi: 10.1124/jpet.104.081315. [PMID: 15687372]
  • Cecilia J Hillard, Abbas Jarrahian. Accumulation of anandamide: evidence for cellular diversity. Neuropharmacology. 2005 Jun; 48(8):1072-8. doi: 10.1016/j.neuropharm.2004.12.012. [PMID: 15910883]
  • Sándor Bátkai, Pál Pacher, Douglas Osei-Hyiaman, Svetlana Radaeva, Jie Liu, Judith Harvey-White, László Offertáler, Ken Mackie, M Audrey Rudd, Richard D Bukoski, George Kunos. Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension. Circulation. 2004 Oct; 110(14):1996-2002. doi: 10.1161/01.cir.0000143230.23252.d2. [PMID: 15451779]
  • Marie Karlsson, Charlotta Påhlsson, Christopher J Fowler. Reversible, temperature-dependent, and AM404-inhibitable adsorption of anandamide to cell culture wells as a confounding factor in release experiments. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2004 Jun; 22(2-3):181-9. doi: 10.1016/j.ejps.2004.03.009. [PMID: 15158903]
  • George Lees, Antonios Dougalis. Differential effects of the sleep-inducing lipid oleamide and cannabinoids on the induction of long-term potentiation in the CA1 neurons of the rat hippocampus in vitro. Brain research. 2004 Jan; 997(1):1-14. doi: 10.1016/j.brainres.2003.10.019. [PMID: 14715144]
  • R A Nicholson, C Liao, J Zheng, L S David, L Coyne, A C Errington, G Singh, G Lees. Sodium channel inhibition by anandamide and synthetic cannabimimetics in brain. Brain research. 2003 Jul; 978(1-2):194-204. doi: 10.1016/s0006-8993(03)02808-7. [PMID: 12834914]
  • J C Jerman, J Gray, S J Brough, L Ooi, D Owen, J B Davis, D Smart. Comparison of effects of anandamide at recombinant and endogenous rat vanilloid receptors. British journal of anaesthesia. 2002 Dec; 89(6):882-7. doi: 10.1093/bja/aef281. [PMID: 12453933]
  • V Ralevic, D A Kendall, J C Jerman, D N Middlemiss, D Smart. Cannabinoid activation of recombinant and endogenous vanilloid receptors. European journal of pharmacology. 2001 Jul; 424(3):211-9. doi: 10.1016/s0014-2999(01)01153-0. [PMID: 11672565]
  • A Giuffrida, M Beltramo, D Piomelli. Mechanisms of endocannabinoid inactivation: biochemistry and pharmacology. The Journal of pharmacology and experimental therapeutics. 2001 Jul; 298(1):7-14. doi: ". [PMID: 11408519]
  • W C Chen, J K Huang, J S Cheng, J C Tsai, A J Chiang, K J Chou, C P Liu, C R Jan. AM-404 elevates renal intracellular Ca(2+), questioning its selectivity as a pharmacological tool for investigating the anandamide transporter. Journal of pharmacological and toxicological methods. 2001 May; 45(3):195-8. doi: 10.1016/s1056-8719(01)00148-4. [PMID: 11755382]
  • A S Rice. Cannabinoids and pain. Current opinion in investigational drugs (London, England : 2000). 2001 Mar; 2(3):399-414. doi: ". [PMID: 11575713]
  • M MacCarrone, M Bari, A Menichelli, E Giuliani, D Del Principe, A Finazzi-Agrò. Human platelets bind and degrade 2-arachidonoylglycerol, which activates these cells through a cannabinoid receptor. European journal of biochemistry. 2001 Feb; 268(3):819-25. doi: 10.1046/j.1432-1327.2001.01942.x. [PMID: 11168423]
  • A Giuffrida, F Rodriguez de Fonseca, F Nava, P Loubet-Lescoulié, D Piomelli. Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404. European journal of pharmacology. 2000 Nov; 408(2):161-8. doi: 10.1016/s0014-2999(00)00786-x. [PMID: 11080522]
  • A Szallasi, V Di Marzo. New perspectives on enigmatic vanilloid receptors. Trends in neurosciences. 2000 Oct; 23(10):491-7. doi: 10.1016/s0166-2236(00)01630-1. [PMID: 11006466]
  • M Beltramo, D Piomelli. Carrier-mediated transport and enzymatic hydrolysis of the endogenous cannabinoid 2-arachidonylglycerol. Neuroreport. 2000 Apr; 11(6):1231-5. doi: 10.1097/00001756-200004270-00018. [PMID: 10817598]
  • D Piomelli, M Beltramo, S Glasnapp, S Y Lin, A Goutopoulos, X Q Xie, A Makriyannis. Structural determinants for recognition and translocation by the anandamide transporter. Proceedings of the National Academy of Sciences of the United States of America. 1999 May; 96(10):5802-7. doi: 10.1073/pnas.96.10.5802. [PMID: 10318965]
  • S González, J Romero, R de Miguel, I Lastres-Becker, M A Villanua, A Makriyannis, J A Ramos, J J Fernández-Ruiz. Extrapyramidal and neuroendocrine effects of AM404, an inhibitor of the carrier-mediated transport of anandamide. Life sciences. 1999; 65(3):327-36. doi: 10.1016/s0024-3205(99)00251-9. [PMID: 10447218]
  • M Beltramo, D Piomelli. Anandamide transport inhibition by the vanilloid agonist olvanil. European journal of pharmacology. 1999 Jan; 364(1):75-8. doi: 10.1016/s0014-2999(98)00821-8. [PMID: 9920187]