trans-C75 (BioDeep_00000600576)

   


代谢物信息卡片


trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid

化学式: C14H22O4 (254.1518012)
中文名称: C75反式
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCC1C(C(=C)C(=O)O1)C(=O)O
InChI: InChI=1S/C14H22O4/c1-3-4-5-6-7-8-9-11-12(13(15)16)10(2)14(17)18-11/h11-12H,2-9H2,1H3,(H,15,16)/t11-,12+/m1/s1

描述信息

trans-C75 ((±)-C75) is an enantiomer of C75. C75 is a synthetic fatty-acid synthase (FASN) inhibitor.

同义名列表

5 个代谢物同义名

trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid; trans-C75; tetrahydro-4-methylene-2R-octyl-5-oxo-3S-furancarboxylic acid; C75; (±)-C75



数据库引用编号

8 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

  • Ya-Yun Liu, Xiao-Dong Liang, Chun-Chun Liu, Yan Cheng, Huan Chen, Abdul Sattar Baloch, Jin Zhang, Yun Young Go, Bin Zhou. Fatty Acid Synthase Is Involved in Classical Swine Fever Virus Replication by Interaction with NS4B. Journal of virology. 2021 08; 95(17):e0078121. doi: 10.1128/jvi.00781-21. [PMID: 34132567]
  • Dipayan Bose, Somenath Banerjee, Nabanita Chatterjee, Subhadip Das, Moumita Saha, Krishna Das Saha. Inhibition of TGF-β induced lipid droplets switches M2 macrophages to M1 phenotype. Toxicology in vitro : an international journal published in association with BIBRA. 2019 Aug; 58(?):207-214. doi: 10.1016/j.tiv.2019.03.037. [PMID: 30930231]
  • Jingfeng Li, Yu Sun, Yuying Li, Ximeng Liu, Qi Yue, Zhaofei Li. Inhibition of cellular fatty acid synthase impairs replication of budded virions of Autographa californica multiple nucleopolyhedrovirus in Spodoptera frugiperda cells. Virus research. 2018 07; 252(?):41-47. doi: 10.1016/j.virusres.2018.05.007. [PMID: 29746884]
  • Chien-Feng Li, Fu-Min Fang, Yen-Yang Chen, Ting-Ting Liu, Ti-Chun Chan, Shih-Chen Yu, Li-Tzong Chen, Hsuan-Ying Huang. Overexpressed Fatty Acid Synthase in Gastrointestinal Stromal Tumors: Targeting a Progression-Associated Metabolic Driver Enhances the Antitumor Effect of Imatinib. Clinical cancer research : an official journal of the American Association for Cancer Research. 2017 Aug; 23(16):4908-4918. doi: 10.1158/1078-0432.ccr-16-2770. [PMID: 28442505]
  • Sudeshna Goswami, Neelam Sharma-Walia. Crosstalk between osteoprotegerin (OPG), fatty acid synthase (FASN) and, cycloxygenase-2 (COX-2) in breast cancer: implications in carcinogenesis. Oncotarget. 2016 Sep; 7(37):58953-58974. doi: 10.18632/oncotarget.9835. [PMID: 27270654]
  • Felipe Slebe, Federico Rojo, Maria Vinaixa, Mar García-Rocha, Giorgia Testoni, Marc Guiu, Evarist Planet, Sara Samino, Enrique J Arenas, Antoni Beltran, Ana Rovira, Ana Lluch, Xavier Salvatella, Oscar Yanes, Joan Albanell, Joan J Guinovart, Roger R Gomis. FoxA and LIPG endothelial lipase control the uptake of extracellular lipids for breast cancer growth. Nature communications. 2016 Apr; 7(?):11199. doi: 10.1038/ncomms11199. [PMID: 27045898]
  • Michael Kuncewitch, Weng Lang Yang, Asha Jacob, Adam Khader, Matthew Giangola, Jeff Nicastro, Gene F Coppa, Ping Wang. Inhibition of fatty acid synthase with C75 decreases organ injury after hemorrhagic shock. Surgery. 2016 Feb; 159(2):570-9. doi: 10.1016/j.surg.2015.07.036. [PMID: 26372196]
  • Juan Pablo Idrovo, Weng-Lang Yang, Asha Jacob, Lana Corbo, Jeffrey Nicastro, Gene F Coppa, Ping Wang. Inhibition of lipogenesis reduces inflammation and organ injury in sepsis. The Journal of surgical research. 2016 Jan; 200(1):242-9. doi: 10.1016/j.jss.2015.06.059. [PMID: 26216747]
  • Ami V Patel, Gunnar Johansson, Melissa C Colbert, Biplab Dasgupta, Nancy Ratner. Fatty acid synthase is a metabolic oncogene targetable in malignant peripheral nerve sheath tumors. Neuro-oncology. 2015 Dec; 17(12):1599-608. doi: 10.1093/neuonc/nov076. [PMID: 26116612]
  • Yun-Chieh Hsieh, Yi-Min Chen, Chun-Yuan Li, Yu-Han Chang, Suh-Yuen Liang, Shu-Yu Lin, Chang-Yi Lin, Sheng-Hsiung Chang, Yi-Jan Wang, Kay-Hooi Khoo, Takashi Aoki, Han-Ching Wang. To complete its replication cycle, a shrimp virus changes the population of long chain fatty acids during infection via the PI3K-Akt-mTOR-HIF1α pathway. Developmental and comparative immunology. 2015 Nov; 53(1):85-95. doi: 10.1016/j.dci.2015.06.001. [PMID: 26112000]
  • J J Zhu, J Luo, Y T Sun, H B Shi, J Li, M Wu, K Yu, A B Haile, J J Loor. Short communication: Effect of inhibition of fatty acid synthase on triglyceride accumulation and effect on lipid metabolism genes in goat mammary epithelial cells. Journal of dairy science. 2015 May; 98(5):3485-91. doi: 10.3168/jds.2014-8202. [PMID: 25726120]
  • Sebastien Elis, Alice Desmarchais, Virginie Maillard, Svetlana Uzbekova, Philippe Monget, Joëlle Dupont. Cell proliferation and progesterone synthesis depend on lipid metabolism in bovine granulosa cells. Theriogenology. 2015 Mar; 83(5):840-53. doi: 10.1016/j.theriogenology.2014.11.019. [PMID: 25583222]
  • Martin C Sadowski, Rebecca H Pouwer, Jennifer H Gunter, Amy A Lubik, Ronald J Quinn, Colleen C Nelson. The fatty acid synthase inhibitor triclosan: repurposing an anti-microbial agent for targeting prostate cancer. Oncotarget. 2014 Oct; 5(19):9362-81. doi: 10.18632/oncotarget.2433. [PMID: 25313139]
  • David O'Sullivan, Gerritje J W van der Windt, Stanley Ching-Cheng Huang, Jonathan D Curtis, Chih-Hao Chang, Michael D Buck, Jing Qiu, Amber M Smith, Wing Y Lam, Lisa M DiPlato, Fong-Fu Hsu, Morris J Birnbaum, Edward J Pearce, Erika L Pearce. Memory CD8(+) T cells use cell-intrinsic lipolysis to support the metabolic programming necessary for development. Immunity. 2014 Jul; 41(1):75-88. doi: 10.1016/j.immuni.2014.06.005. [PMID: 25001241]
  • Shingo Matsuo, Weng-Lang Yang, Monowar Aziz, Shingo Kameoka, Ping Wang. Fatty acid synthase inhibitor C75 ameliorates experimental colitis. Molecular medicine (Cambridge, Mass.). 2014 Jan; 20(?):1-9. doi: 10.2119/molmed.2013.00113. [PMID: 24306512]
  • Joseph W McFadden, Susan Aja, Qun Li, Veera V R Bandaru, Eun-Kyoung Kim, Norman J Haughey, Francis P Kuhajda, Gabriele V Ronnett. Increasing fatty acid oxidation remodels the hypothalamic neurometabolome to mitigate stress and inflammation. PloS one. 2014; 9(12):e115642. doi: 10.1371/journal.pone.0115642. [PMID: 25541737]
  • Nataliya E Chorna, Iván J Santos-Soto, Nestor M Carballeira, Joan L Morales, Janneliz de la Nuez, Alma Cátala-Valentin, Anatoliy P Chornyy, Adrinel Vázquez-Montes, Sandra Peña De Ortiz. Fatty acid synthase as a factor required for exercise-induced cognitive enhancement and dentate gyrus cellular proliferation. PloS one. 2013; 8(11):e77845. doi: 10.1371/journal.pone.0077845. [PMID: 24223732]
  • Yunjeong Kim, David George, Allan M Prior, Keshar Prasain, Shuanghong Hao, Duy D Le, Duy H Hua, Kyeong-Ok Chang. Novel triacsin C analogs as potential antivirals against rotavirus infections. European journal of medicinal chemistry. 2012 Apr; 50(?):311-8. doi: 10.1016/j.ejmech.2012.02.010. [PMID: 22365411]
  • Jacob Pellinen, Éva Szentirmai. The effects of C75, an inhibitor of fatty acid synthase, on sleep and metabolism in mice. PloS one. 2012; 7(2):e30651. doi: 10.1371/journal.pone.0030651. [PMID: 22348016]
  • Simona M Ceccarelli, Odile Chomienne, Marcel Gubler, Arduino Arduini. Carnitine palmitoyltransferase (CPT) modulators: a medicinal chemistry perspective on 35 years of research. Journal of medicinal chemistry. 2011 May; 54(9):3109-52. doi: 10.1021/jm100809g. [PMID: 21504156]
  • C Rae, A Graham. Fatty acid synthase inhibitor, C75, blocks resistin-induced increases in lipid accumulation by human macrophages. Diabetes, obesity & metabolism. 2008 Dec; 10(12):1271-4. doi: 10.1111/j.1463-1326.2008.00962.x. [PMID: 19040646]
  • Maria T Accioly, Patricia Pacheco, Clarissa M Maya-Monteiro, Nina Carrossini, Bruno K Robbs, Silvia S Oliveira, Cristiane Kaufmann, José A Morgado-Diaz, Patricia T Bozza, João P B Viola. Lipid bodies are reservoirs of cyclooxygenase-2 and sites of prostaglandin-E2 synthesis in colon cancer cells. Cancer research. 2008 Mar; 68(6):1732-40. doi: 10.1158/0008-5472.can-07-1999. [PMID: 18339853]
  • Feifan Guo, Douglas R Cavener. The GCN2 eIF2alpha kinase regulates fatty-acid homeostasis in the liver during deprivation of an essential amino acid. Cell metabolism. 2007 Feb; 5(2):103-14. doi: 10.1016/j.cmet.2007.01.001. [PMID: 17276353]
  • Assia Bentebibel, David Sebastián, Laura Herrero, Eduardo López-Viñas, Dolors Serra, Guillermina Asins, Paulino Gómez-Puertas, Fausto G Hegardt. Novel effect of C75 on carnitine palmitoyltransferase I activity and palmitate oxidation. Biochemistry. 2006 Apr; 45(14):4339-50. doi: 10.1021/bi052186q. [PMID: 16584169]
  • Bernhard Schmid, Jörg F Rippmann, Moh Tadayyon, Bradford S Hamilton. Inhibition of fatty acid synthase prevents preadipocyte differentiation. Biochemical and biophysical research communications. 2005 Mar; 328(4):1073-82. doi: 10.1016/j.bbrc.2005.01.067. [PMID: 15707987]
  • Patricia M Alli, Michael L Pinn, Elizabeth M Jaffee, Jill M McFadden, Francis P Kuhajda. Fatty acid synthase inhibitors are chemopreventive for mammary cancer in neu-N transgenic mice. Oncogene. 2005 Jan; 24(1):39-46. doi: 10.1038/sj.onc.1208174. [PMID: 15489885]
  • Nengyu Yang, Joanne S Kays, Tiffanie R Skillman, Lorri Burris, Thomas W Seng, Craig Hammond. C75 [4-methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid] activates carnitine palmitoyltransferase-1 in isolated mitochondria and intact cells without displacement of bound malonyl CoA. The Journal of pharmacology and experimental therapeutics. 2005 Jan; 312(1):127-33. doi: 10.1124/jpet.104.074104. [PMID: 15356215]
  • Li-Hong Liu, Xiao-Kui Wang, Yuan-Dong Hu, Jian-Lei Kang, Li-Li Wang, Song Li. Effects of a fatty acid synthase inhibitor on adipocyte differentiation of mouse 3T3-L1 cells. Acta pharmacologica Sinica. 2004 Aug; 25(8):1052-7. doi: ". [PMID: 15301739]
  • Kanji A Takahashi, James L Smart, Hongyan Liu, Roger D Cone. The anorexigenic fatty acid synthase inhibitor, C75, is a nonspecific neuronal activator. Endocrinology. 2004 Jan; 145(1):184-93. doi: 10.1210/en.2003-0337. [PMID: 14512433]
  • Weibo Zhou, P Jeanette Simpson, Jill M McFadden, Craig A Townsend, Susan M Medghalchi, Aravinda Vadlamudi, Michael L Pinn, Gabriele V Ronnett, Francis P Kuhajda. Fatty acid synthase inhibition triggers apoptosis during S phase in human cancer cells. Cancer research. 2003 Nov; 63(21):7330-7. doi: ". [PMID: 14612531]
  • B L Samples, G L Pool, R H Lumb. Subcellular localization of enzyme activities involved in the metabolism of platelet-activating factor in rainbow trout leukocytes. Biochimica et biophysica acta. 1999 Mar; 1437(3):357-66. doi: 10.1016/s1388-1981(99)00030-x. [PMID: 10101269]
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