Englerin A (BioDeep_00000395660)

   

PANOMIX_OTCML-2023


代谢物信息卡片


[(1S,2R,5R,6R,7S,8R,10R)-10-(2-hydroxyacetyl)oxy-1,5-dimethyl-8-propan-2-yl-11-oxatricyclo[6.2.1.02,6]undecan-7-yl] (E)-3-phenylprop-2-enoate

化学式: C26H34O6 (442.2355264)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 70.97%

分子结构信息

SMILES: CC1CCC2C1C(C3(CC(C2(O3)C)OC(=O)CO)C(C)C)OC(=O)C=CC4=CC=CC=C4
InChI: InChI=1S/C26H34O6/c1-16(2)26-14-20(30-22(29)15-27)25(4,32-26)19-12-10-17(3)23(19)24(26)31-21(28)13-11-18-8-6-5-7-9-18/h5-9,11,13,16-17,19-20,23-24,27H,10,12,14-15H2,1-4H3/b13-11+/t17-,19-,20-,23-,24+,25+,26-/m1/s1

描述信息

Englerin A is a guaiane sesquiterpenoid that is isolated from the bark of Phyllanthus engleri, a plant native to Tanzania and Zimbabwe. It acts as a potent and specific inhibitor of renal cancer cell growth. It has a role as a metabolite and an antineoplastic agent. It is a guaiane sesquiterpenoid, a cinnamate ester and a glycolate ester.
Englerin A is a natural product found in Phyllanthus engleri with data available.
A guaiane sesquiterpenoid that is isolated from the bark of Phyllanthus engleri, a plant native to Tanzania and Zimbabwe. It acts as a potent and specific inhibitor of renal cancer cell growth.
Englerin A is a potent and selective activator of TRPC4 and TRPC5 channels, with EC50s of 11.2 and 7.6 nM, respectively. Englerin A can induce renal carcinoma cells death by elevated Ca2+ influx and Ca2+ cell overload[1][2][3].

同义名列表

6 个代谢物同义名

[(1S,2R,5R,6R,7S,8R,10R)-10-(2-hydroxyacetyl)oxy-1,5-dimethyl-8-propan-2-yl-11-oxatricyclo[6.2.1.02,6]undecan-7-yl] (E)-3-phenylprop-2-enoate; (1R,3aR,4S,5R,7R,8S,8aR)-5-(glycoloyloxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl (2E)-3-phenylacrylate; (1R,3aR,4S,5R,7R,8S,8aR)-5-(2-Hydroxyacetoxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate; (-)-englerin A; Englerin-A; Englerin A



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

Reactome(0)

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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)

PlantCyc(0)

COVID-19 Disease Map(0)

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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

  • João de Sousa Valente, Khadija M Alawi, Sabah Bharde, Ali A Zarban, Xenia Kodji, Dibesh Thapa, Fulye Argunhan, Brentton Barrett, Istvan Nagy, Susan D Brain. (-)-Englerin-A Has Analgesic and Anti-Inflammatory Effects Independent of TRPC4 and 5. International journal of molecular sciences. 2021 Jun; 22(12):. doi: 10.3390/ijms22126380. [PMID: 34203675]
  • Thomas Siemon, Zhangqian Wang, Guangkai Bian, Tobias Seitz, Ziling Ye, Yan Lu, Shu Cheng, Yunkun Ding, Yanglei Huang, Zixin Deng, Tiangang Liu, Mathias Christmann. Semisynthesis of Plant-Derived Englerin A Enabled by Microbe Engineering of Guaia-6,10(14)-diene as Building Block. Journal of the American Chemical Society. 2020 02; 142(6):2760-2765. doi: 10.1021/jacs.9b12940. [PMID: 31999448]
  • Jinsung Kim, Juyeon Ko, Chansik Hong, Insuk So. Structure-Function Relationship and Physiological Roles of Transient Receptor Potential Canonical (TRPC) 4 and 5 Channels. Cells. 2019 Dec; 9(1):. doi: 10.3390/cells9010073. [PMID: 31892199]
  • Aminah Suhail Qureshi, Sikander Ali. Review: Warburg effect and renal cancer caused by errs in fumarate hydratase encoding gene. Pakistan journal of pharmaceutical sciences. 2019 Mar; 32(2):743-749. doi: . [PMID: 31081789]
  • Xuexiang Wang, Ranadheer R Dande, Hao Yu, Beata Samelko, Rachel E Miller, Mehmet M Altintas, Jochen Reiser. TRPC5 Does Not Cause or Aggravate Glomerular Disease. Journal of the American Society of Nephrology : JASN. 2018 02; 29(2):409-415. doi: 10.1681/asn.2017060682. [PMID: 29061651]
  • Katsuhiko Muraki, Kaori Ohnishi, Akiho Takezawa, Hiroka Suzuki, Noriyuki Hatano, Yukiko Muraki, Nurasyikin Hamzah, Richard Foster, Herbert Waldmann, Peter Nussbaumer, Mathias Christmann, Robin S Bon, David J Beech. Na+ entry through heteromeric TRPC4/C1 channels mediates (-)Englerin A-induced cytotoxicity in synovial sarcoma cells. Scientific reports. 2017 12; 7(1):16988. doi: 10.1038/s41598-017-17303-3. [PMID: 29209034]
  • Hussein N Rubaiy, Melanie J Ludlow, Robin S Bon, David J Beech. Pico145 - powerful new tool for TRPC1/4/5 channels. Channels (Austin, Tex.). 2017 09; 11(5):362-364. doi: 10.1080/19336950.2017.1317485. [PMID: 28399685]
  • Zhenhua Wu, Senzhi Zhao, David M Fash, Zhenwu Li, William J Chain, John A Beutler. Englerins: A Comprehensive Review. Journal of natural products. 2017 03; 80(3):771-781. doi: 10.1021/acs.jnatprod.6b01167. [PMID: 28170253]
  • Melanie J Ludlow, Hannah J Gaunt, Hussein N Rubaiy, Katie E Musialowski, Nicola M Blythe, Naveen S Vasudev, Katsuhiko Muraki, David J Beech. (-)-Englerin A-evoked Cytotoxicity Is Mediated by Na+ Influx and Counteracted by Na+/K+-ATPase. The Journal of biological chemistry. 2017 Jan; 292(2):723-731. doi: 10.1074/jbc.m116.755678. [PMID: 27875305]
  • Ayse Batova, Diego Altomare, Kim E Creek, Robert K Naviaux, Lin Wang, Kefeng Li, Erica Green, Richard Williams, Jane C Naviaux, Mitchell Diccianni, Alice L Yu. Englerin A induces an acute inflammatory response and reveals lipid metabolism and ER stress as targetable vulnerabilities in renal cell carcinoma. PloS one. 2017; 12(3):e0172632. doi: 10.1371/journal.pone.0172632. [PMID: 28296891]
  • Vittorio Caropreso, Emad Darvishi, Thomas J Turbyville, Ranjala Ratnayake, Patrick J Grohar, James B McMahon, Girma M Woldemichael. Englerin A Inhibits EWS-FLI1 DNA Binding in Ewing Sarcoma Cells. The Journal of biological chemistry. 2016 May; 291(19):10058-66. doi: 10.1074/jbc.m115.701375. [PMID: 26961871]
  • Carole Sourbier, Bradley T Scroggins, Philip Z Mannes, Pei-Jyun Liao, Karsten Siems, Dietmar Wolf, John A Beutler, W Marston Linehan, Leonard Neckers. Tonantzitlolone cytotoxicity toward renal cancer cells is PKCθ- and HSF1-dependent. Oncotarget. 2015 Oct; 6(30):29963-74. doi: 10.18632/oncotarget.4676. [PMID: 26298773]
  • Taiki Hanari, Naoyuki Shimada, Yasunobu Kurosaki, Neetipalli Thrimurtulu, Hisanori Nambu, Masahiro Anada, Shunichi Hashimoto. Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition. Chemistry (Weinheim an der Bergstrasse, Germany). 2015 Aug; 21(33):11671-6. doi: 10.1002/chem.201502009. [PMID: 26179743]
  • Cheryl Carson, Pichai Raman, Jennifer Tullai, Lei Xu, Martin Henault, Emily Thomas, Sarita Yeola, Jianmin Lao, Mark McPate, J Martin Verkuyl, George Marsh, Jason Sarber, Adam Amaral, Scott Bailey, Danuta Lubicka, Helen Pham, Nicolette Miranda, Jian Ding, Hai-Ming Tang, Haisong Ju, Pamela Tranter, Nan Ji, Philipp Krastel, Rishi K Jain, Andrew M Schumacher, Joseph J Loureiro, Elizabeth George, Giuliano Berellini, Nathan T Ross, Simon M Bushell, Gül Erdemli, Jonathan M Solomon. Englerin A Agonizes the TRPC4/C5 Cation Channels to Inhibit Tumor Cell Line Proliferation. PloS one. 2015; 10(6):e0127498. doi: 10.1371/journal.pone.0127498. [PMID: 26098886]
  • Richard T Williams, Alice L Yu, Mitchell B Diccianni, Emmanuel A Theodorakis, Ayse Batova. Renal cancer-selective Englerin A induces multiple mechanisms of cell death and autophagy. Journal of experimental & clinical cancer research : CR. 2013 Aug; 32(?):57. doi: 10.1186/1756-9966-32-57. [PMID: 23958461]
  • Carole Sourbier, Bradley T Scroggins, Ranjala Ratnayake, Thomas L Prince, Sunmin Lee, Min-Jung Lee, Peter Literati Nagy, Young H Lee, Jane B Trepel, John A Beutler, W Marston Linehan, Len Neckers. Englerin A stimulates PKCθ to inhibit insulin signaling and to simultaneously activate HSF1: pharmacologically induced synthetic lethality. Cancer cell. 2013 Feb; 23(2):228-37. doi: 10.1016/j.ccr.2012.12.007. [PMID: 23352416]
  • Jing Xu, Eduardo J E Caro-Diaz, Ayse Batova, Steven D E Sullivan, Emmanuel A Theodorakis. Formal synthesis of (-)-englerin A and cytotoxicity studies of truncated englerins. Chemistry, an Asian journal. 2012 May; 7(5):1052-60. doi: 10.1002/asia.201101021. [PMID: 22415793]
  • Rhone K Akee, Tanya Ransom, Ranjala Ratnayake, James B McMahon, John A Beutler. Chlorinated englerins with selective inhibition of renal cancer cell growth. Journal of natural products. 2012 Mar; 75(3):459-63. doi: 10.1021/np200905u. [PMID: 22280462]
  • Florian J Sulzmaier, Zhenwu Li, Mika L Nakashige, David M Fash, William J Chain, Joe W Ramos. Englerin a selectively induces necrosis in human renal cancer cells. PloS one. 2012; 7(10):e48032. doi: 10.1371/journal.pone.0048032. [PMID: 23144724]
  • Zhenwu Li, Mika Nakashige, William J Chain. A brief synthesis of (-)-englerin A. Journal of the American Chemical Society. 2011 May; 133(17):6553-6. doi: 10.1021/ja201921j. [PMID: 21476574]
  • Lea Radtke, Matthieu Willot, Hongyan Sun, Slava Ziegler, Stephanie Sauerland, Carsten Strohmann, Roland Fröhlich, Peter Habenberger, Herbert Waldmann, Mathias Christmann. Total synthesis and biological evaluation of (-)-englerin A and B: synthesis of analogues with improved activity profile. Angewandte Chemie (International ed. in English). 2011 Apr; 50(17):3998-4002. doi: 10.1002/anie.201007790. [PMID: 21472928]
  • K C Nicolaou, Qiang Kang, Sin Yee Ng, David Y-K Chen. Total synthesis of englerin A. Journal of the American Chemical Society. 2010 Jun; 132(23):8219-22. doi: 10.1021/ja102927n. [PMID: 20496885]
  • Ranjala Ratnayake, David Covell, Tanya T Ransom, Kirk R Gustafson, John A Beutler. Englerin A, a selective inhibitor of renal cancer cell growth, from Phyllanthus engleri. Organic letters. 2009 Jan; 11(1):57-60. doi: 10.1021/ol802339w. [PMID: 19061394]