3-(4-((3-Phenoxybenzyl)amino)phenyl)propanoic acid (BioDeep_00000179640)

   

human metabolite blood metabolite


代谢物信息卡片


3-(4-{[(3-phenoxyphenyl)methyl]amino}phenyl)propanoic acid

化学式: C22H21NO3 (347.1521)
中文名称: 4-[[(3-苯氧苯基)甲基]氨基]苯乙酸
谱图信息: 最多检出来源 Homo sapiens(blood) 13.33%

分子结构信息

SMILES: C1=CC=C(C=C1)OC2=CC=CC(=C2)CNC3=CC=C(C=C3)CCC(=O)O
InChI: InChI=1S/C22H21NO3/c24-22(25)14-11-17-9-12-19(13-10-17)23-16-18-5-4-8-21(15-18)26-20-6-2-1-3-7-20/h1-10,12-13,15,23H,11,14,16H2,(H,24,25)

描述信息

GW9508 is a potent and selective G protein-coupled receptors FFA1 (GPR40) and GPR120 agonist with pEC50s of 7.32 and 5.46, respectively. GW9508 shows ~100-fold selectivity for GPR40 over GPR120. GW9508 is inactive against other GPCRs, kinases, proteases, integrins and PPARs. GW9508 is a glucose-sensitive insulin secretagogue and an ATP-sensitive potassium (KATP) channels opener. Anti-inflammatory and anti-atherosclerotic activities[1][2][3][4].

同义名列表

4 个代谢物同义名

3-(4-{[(3-phenoxyphenyl)methyl]amino}phenyl)propanoic acid; 3-(4-((3-Phenoxybenzyl)amino)phenyl)propanoic acid; 3-(4-((3-Phenoxybenzyl)amino)phenyl)propanoate; GW9508



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

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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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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

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COVID-19 Disease Map(0)

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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。

亚细胞结构定位 关联基因列表


文献列表

  • Lin-Sheng Zhang, Zhi-Shou Zhang, Yu-Zhu Wu, Botang Guo, Jing Li, Xiao-Qi Huang, Feng-Min Zhang, Min-Yao Li, Ping-Chang Yang, Xue-Bao Zheng. Activation of free fatty acid receptors, FFAR1 and FFAR4, ameliorates ulcerative colitis by promote fatty acid metabolism and mediate macrophage polarization. International immunopharmacology. 2024 Mar; 130(?):111778. doi: 10.1016/j.intimp.2024.111778. [PMID: 38432147]
  • Patricia R Souza, Mary E Walker, Nicolas J Goulding, Jesmond Dalli, Mauro Perretti, Lucy V Norling. The GPR40 Agonist GW9508 Enhances Neutrophil Function to Aid Bacterial Clearance During E. coli Infections. Frontiers in immunology. 2020; 11(?):573019. doi: 10.3389/fimmu.2020.573019. [PMID: 33133087]
  • Yu Li, Xue Yang, Hui Zhang, Qiuhong Wu. Pharmacokinetics and metabolism of GW9508 in rat by liquid chromatography/electrospray ionization tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2019 Jun; 170(?):176-186. doi: 10.1016/j.jpba.2019.03.040. [PMID: 30927663]
  • Takuya Hashimoto, Hideo Mogami, Daisuke Tsuriya, Hiroshi Morita, Shigekazu Sasaki, Tatsuro Kumada, Yuko Suzuki, Tetsumei Urano, Yutaka Oki, Takafumi Suda. G-protein-coupled receptor 40 agonist GW9508 potentiates glucose-stimulated insulin secretion through activation of protein kinase Cα and ε in INS-1 cells. PloS one. 2019; 14(9):e0222179. doi: 10.1371/journal.pone.0222179. [PMID: 31498851]
  • Chunxia Liu, Zheng Li, Wei Shi, Huilan Li, Nasi Wang, Yuxuan Dai, Chen Liao, Wenlong Huang, Hai Qian. Improving metabolic stability with deuterium: The discovery of HWL-066, a potent and long-acting free fatty acid receptor 1 agonists. Chemical biology & drug design. 2018 08; 92(2):1547-1554. doi: 10.1111/cbdd.13321. [PMID: 29777569]
  • Tania Quesada-López, Rubén Cereijo, Jean-Valery Turatsinze, Anna Planavila, Montserrat Cairó, Aleix Gavaldà-Navarro, Marion Peyrou, Ricardo Moure, Roser Iglesias, Marta Giralt, Decio L Eizirik, Francesc Villarroya. The lipid sensor GPR120 promotes brown fat activation and FGF21 release from adipocytes. Nature communications. 2016 11; 7(?):13479. doi: 10.1038/ncomms13479. [PMID: 27853148]
  • Meng Li, Xiangyu Meng, Jie Xu, Xiuqing Huang, Hongxia Li, Guoping Li, Shu Wang, Yong Man, Weiqing Tang, Jian Li. GPR40 agonist ameliorates liver X receptor-induced lipid accumulation in liver by activating AMPK pathway. Scientific reports. 2016 04; 6(?):25237. doi: 10.1038/srep25237. [PMID: 27121981]
  • Xiao-Min Ren, Lin-Ying Cao, Jing Zhang, Wei-Ping Qin, Yu Yang, Bin Wan, Liang-Hong Guo. Investigation of the Binding Interaction of Fatty Acids with Human G Protein-Coupled Receptor 40 Using a Site-Specific Fluorescence Probe by Flow Cytometry. Biochemistry. 2016 Apr; 55(13):1989-96. doi: 10.1021/acs.biochem.6b00079. [PMID: 26974599]
  • Kentaro Mizuta, Yi Zhang, Fumiko Mizuta, Hiroshi Hoshijima, Toshiya Shiga, Eiji Masaki, Charles W Emala. Novel identification of the free fatty acid receptor FFAR1 that promotes contraction in airway smooth muscle. American journal of physiology. Lung cellular and molecular physiology. 2015 Nov; 309(9):L970-82. doi: 10.1152/ajplung.00041.2015. [PMID: 26342087]
  • Ihor Zahanich, Ivan Kondratov, Vasyl Naumchyk, Yuri Kheylik, Maxim Platonov, Sergey Zozulya, Mikhail Krasavin. Phenoxymethyl 1,3-oxazoles and 1,2,4-oxadiazoles as potent and selective agonists of free fatty acid receptor 1 (GPR40). Bioorganic & medicinal chemistry letters. 2015 Aug; 25(16):3105-11. doi: 10.1016/j.bmcl.2015.06.018. [PMID: 26096679]
  • Carolina Manosalva, Jaqueline Mena, Zahady Velasquez, Charlotte K Colenso, Sebastian Brauchi, Rafael A Burgos, Maria A Hidalgo. Cloning, identification and functional characterization of bovine free fatty acid receptor-1 (FFAR1/GPR40) in neutrophils. PloS one. 2015; 10(3):e0119715. doi: 10.1371/journal.pone.0119715. [PMID: 25790461]
  • Seong Kwon Ma, Soo Yeon Joo, Hoon-In Choi, Eun Hui Bae, Kwang Il Nam, Jongun Lee, Soo Wan Kim. Activation of G-protein-coupled receptor 40 attenuates the cisplatin-induced apoptosis of human renal proximal tubule epithelial cells. International journal of molecular medicine. 2014 Oct; 34(4):1117-23. doi: 10.3892/ijmm.2014.1874. [PMID: 25092426]
  • Yueqin Liu, Li-Yuan Chen, Milena Sokolowska, Michael Eberlein, Sara Alsaaty, Asuncion Martinez-Anton, Carolea Logun, Hai-Yan Qi, James H Shelhamer. The fish oil ingredient, docosahexaenoic acid, activates cytosolic phospholipase A₂ via GPR120 receptor to produce prostaglandin E₂ and plays an anti-inflammatory role in macrophages. Immunology. 2014 Sep; 143(1):81-95. doi: 10.1111/imm.12296. [PMID: 24673159]
  • Horng-Yih Ou, Hung-Tsung Wu, Hao-Chang Hung, Yi-Ching Yang, Jin-Shang Wu, Chih-Jen Chang. Multiple mechanisms of GW-9508, a selective G protein-coupled receptor 40 agonist, in the regulation of glucose homeostasis and insulin sensitivity. American journal of physiology. Endocrinology and metabolism. 2013 Mar; 304(6):E668-76. doi: 10.1152/ajpendo.00419.2012. [PMID: 23341496]
  • Gioia Petrighi Polidori, Michael A Lomax, Kevin Docherty. Palmitate enhances the differentiation of mouse embryonic stem cells towards white adipocyte lineages. Molecular and cellular endocrinology. 2012 Sep; 361(1-2):40-50. doi: 10.1016/j.mce.2012.03.010. [PMID: 22484460]
  • Sarah-Jane Watson, Alastair J H Brown, Nicholas D Holliday. Differential signaling by splice variants of the human free fatty acid receptor GPR120. Molecular pharmacology. 2012 May; 81(5):631-42. doi: 10.1124/mol.111.077388. [PMID: 22282525]
  • Nicol Kruska, Georg Reiser. Phytanic acid and pristanic acid, branched-chain fatty acids associated with Refsum disease and other inherited peroxisomal disorders, mediate intracellular Ca2+ signaling through activation of free fatty acid receptor GPR40. Neurobiology of disease. 2011 Aug; 43(2):465-72. doi: 10.1016/j.nbd.2011.04.020. [PMID: 21570468]
  • Maria A Hidalgo, Carla Nahuelpan, Carolina Manosalva, Evelyn Jara, Maria D Carretta, Ivan Conejeros, Anitsi Loaiza, Ricardo Chihuailaf, Rafael A Burgos. Oleic acid induces intracellular calcium mobilization, MAPK phosphorylation, superoxide production and granule release in bovine neutrophils. Biochemical and biophysical research communications. 2011 Jun; 409(2):280-6. doi: 10.1016/j.bbrc.2011.04.144. [PMID: 21575602]
  • Nicola J Smith, Leigh A Stoddart, Nicola M Devine, Laura Jenkins, Graeme Milligan. The action and mode of binding of thiazolidinedione ligands at free fatty acid receptor 1. The Journal of biological chemistry. 2009 Jun; 284(26):17527-39. doi: 10.1074/jbc.m109.012849. [PMID: 19398560]
  • Irina G Tikhonova, Chi Shing Sum, Susanne Neumann, Craig J Thomas, Bruce M Raaka, Stefano Costanzi, Marvin C Gershengorn. Bidirectional, iterative approach to the structural delineation of the functional 'chemoprint' in GPR40 for agonist recognition. Journal of medicinal chemistry. 2007 Jun; 50(13):2981-9. doi: 10.1021/jm0614782. [PMID: 17552505]
  • Celia P Briscoe, Andrew J Peat, Stephen C McKeown, David F Corbett, Aaron S Goetz, Thomas R Littleton, David C McCoy, Terry P Kenakin, John L Andrews, Carina Ammala, James A Fornwald, Diane M Ignar, Stephen Jenkinson. Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules. British journal of pharmacology. 2006 Jul; 148(5):619-28. doi: 10.1038/sj.bjp.0706770. [PMID: 16702987]
  • A J BORKOWSKI, S S HOWARDS, J H LARAGH. ANTIOTENSIN AND ELECTROLYTE EXCRETION IN RENOVASCULAR HYPERTENSION. The American journal of physiology. 1965 Jun; 208(?):1087-92. doi: 10.1152/ajplegacy.1965.208.6.1087. [PMID: 14301363]