triacsin c (BioDeep_00000321553)

   


代谢物信息卡片


Triacsin C from Streptomyces sp.

化学式: C11H17N3O (207.1371552)
中文名称: 三氮菌素 C
谱图信息: 最多检出来源 Anoectochilus roxburghii(viridiplantae) 75%

分子结构信息

SMILES: CCCC=CCC=CC=CC=NN=NO
InChI: InChI=1S/C11H17N3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h4-5,7-11H,2-3,6H2,1H3,(H,13,15)/b5-4+,8-7+,10-9+,12-11+

描述信息

A nitroso compound that is N-undecylnitrous hydrazide carrying double bonds at positions 1,2,4, and 7. It is a long-chain fatty acyl CoA synthetase inhibitor and interferes with lipid metabolism by inhibiting the de novo synthesis of glycerolipids and cholesterol esters.
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
D004791 - Enzyme Inhibitors

同义名列表

2 个代谢物同义名

Triacsin C from Streptomyces sp.; triacsin c



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

  • Wenqiang Xin, Yongli Pan, Wei Wei, Stefan T Gerner, Sabine Huber, Martin Juenemann, Marius Butz, Mathias Bähr, Hagen B Huttner, Thorsten R Doeppner. TGF-β1 Decreases Microglia-Mediated Neuroinflammation and Lipid Droplet Accumulation in an In Vitro Stroke Model. International journal of molecular sciences. 2023 Dec; 24(24):. doi: 10.3390/ijms242417329. [PMID: 38139158]
  • Areej Al-Roub, Nadeem Akhter, Amnah Al-Sayyar, Ajit Wilson, Reeby Thomas, Shihab Kochumon, Fatema Al-Rashed, Fahd Al-Mulla, Sardar Sindhu, Rasheed Ahmad. Short Chain Fatty Acid Acetate Increases TNFα-Induced MCP-1 Production in Monocytic Cells via ACSL1/MAPK/NF-κB Axis. International journal of molecular sciences. 2021 Jul; 22(14):. doi: 10.3390/ijms22147683. [PMID: 34299302]
  • Taku Nakayama, Tomonori Sano, Yoshiki Oshimo, Chiaki Kawada, Moe Kasai, Shinkuro Yamamoto, Hideo Fukuhara, Keiji Inoue, Shun-Ichiro Ogura. Enhanced lipid metabolism induces the sensitivity of dormant cancer cells to 5-aminolevulinic acid-based photodynamic therapy. Scientific reports. 2021 03; 11(1):7290. doi: 10.1038/s41598-021-86886-9. [PMID: 33790399]
  • Guang Ren, Sushant Bhatnagar, Daniel J Hahn, Jeong-A Kim. Long-chain acyl-CoA synthetase-1 mediates the palmitic acid-induced inflammatory response in human aortic endothelial cells. American journal of physiology. Endocrinology and metabolism. 2020 11; 319(5):E893-E903. doi: 10.1152/ajpendo.00117.2020. [PMID: 32954825]
  • Tatyana G Vishnyakova, Alexander V Bocharov, Irina N Baranova, Roger Kurlander, Steven K Drake, Zhigang Chen, Marcelo Amar, Denis Sviridov, Boris Vaisman, Eugenia Poliakov, Alan T Remaley, Thomas L Eggerman, Amy P Patterson. SR-BI mediates neutral lipid sorting from LDL to lipid droplets and facilitates their formation. PloS one. 2020; 15(10):e0240659. doi: 10.1371/journal.pone.0240659. [PMID: 33057430]
  • Ryutaro Aizawa, Megumi Ibayashi, Takayuki Tatsumi, Atsushi Yamamoto, Toshiaki Kokubo, Naoyuki Miyasaka, Ken Sato, Shuntaro Ikeda, Naojiro Minami, Satoshi Tsukamoto. Synthesis and maintenance of lipid droplets are essential for mouse preimplantation embryonic development. Development (Cambridge, England). 2019 11; 146(22):. doi: 10.1242/dev.181925. [PMID: 31772031]
  • Jin Zhang, Xing Gao, Yuan Yuan, Chao Sun, Yuanlin Zhao, Liming Xiao, Ying Yang, Yu Gu, Risheng Yang, Peizhen Hu, Lijun Zhang, Chao Wang, Jing Ye. Perilipin 5 alleviates HCV NS5A-induced lipotoxic injuries in liver. Lipids in health and disease. 2019 Apr; 18(1):87. doi: 10.1186/s12944-019-1022-7. [PMID: 30954078]
  • Eric Soupene, Frans A Kuypers. Phosphatidylserine decarboxylase CT699, lysophospholipid acyltransferase CT775, and acyl-ACP synthase CT776 provide membrane lipid diversity to Chlamydia trachomatis. Scientific reports. 2017 11; 7(1):15767. doi: 10.1038/s41598-017-16116-8. [PMID: 29150677]
  • Carlos R P Dechandt, Felippe H Zuccolotto-Dos-Reis, Bruno G Teodoro, Anna Maria A P Fernandes, Marcos N Eberlin, Isis C Kettelhut, Carlos Curti, Luciane C Alberici. Triacsin C reduces lipid droplet formation and induces mitochondrial biogenesis in primary rat hepatocytes. Journal of bioenergetics and biomembranes. 2017 Oct; 49(5):399-411. doi: 10.1007/s10863-017-9725-9. [PMID: 28918598]
  • Milton To, Clark W H Peterson, Melissa A Roberts, Jessica L Counihan, Tiffany T Wu, Mercedes S Forster, Daniel K Nomura, James A Olzmann. Lipid disequilibrium disrupts ER proteostasis by impairing ERAD substrate glycan trimming and dislocation. Molecular biology of the cell. 2017 01; 28(2):270-284. doi: 10.1091/mbc.e16-07-0483. [PMID: 27881664]
  • Lucía C Lagrutta, Sandra Montero-Villegas, Juan P Layerenza, Martín S Sisti, Margarita M García de Bravo, Ana Ves-Losada. Reversible Nuclear-Lipid-Droplet Morphology Induced by Oleic Acid: A Link to Cellular-Lipid Metabolism. PloS one. 2017; 12(1):e0170608. doi: 10.1371/journal.pone.0170608. [PMID: 28125673]
  • Michele Alves-Bezerra, Eric L Klett, Iron F De Paula, Isabela B Ramos, Rosalind A Coleman, Katia C Gondim. Long-chain acyl-CoA synthetase 2 knockdown leads to decreased fatty acid oxidation in fat body and reduced reproductive capacity in the insect Rhodnius prolixus. Biochimica et biophysica acta. 2016 Jul; 1861(7):650-62. doi: 10.1016/j.bbalip.2016.04.007. [PMID: 27091636]
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  • Allan M Prior, Man Zhang, Nina Blakeman, Palika Datta, Hung Pham, Qian Chen, Lindon H Young, Margaret T Weis, Duy H Hua. Inhibition of long chain fatty acyl-CoA synthetase (ACSL) and ischemia reperfusion injury. Bioorganic & medicinal chemistry letters. 2014 Feb; 24(4):1057-61. doi: 10.1016/j.bmcl.2014.01.016. [PMID: 24480468]
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  • 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]
  • Yung-Sheng Chang, Chien-Ting Tsai, Chien-An Huangfu, Wen-Ya Huang, Huan-Yao Lei, Chiou-Feng Lin, Ih-Jen Su, Wen-Tsan Chang, Pei-Huan Wu, Ya-Ting Chen, Jui-Hsiang Hung, Kung-Chia Young, Ming-Derg Lai. ACSL3 and GSK-3β are essential for lipid upregulation induced by endoplasmic reticulum stress in liver cells. Journal of cellular biochemistry. 2011 Mar; 112(3):881-93. doi: 10.1002/jcb.22996. [PMID: 21328461]
  • Winsome Cheung, Michael Gill, Alessandro Esposito, Clemens F Kaminski, Nathalie Courousse, Serge Chwetzoff, Germain Trugnan, Nandita Keshavan, Andrew Lever, Ulrich Desselberger. Rotaviruses associate with cellular lipid droplet components to replicate in viroplasms, and compounds disrupting or blocking lipid droplets inhibit viroplasm formation and viral replication. Journal of virology. 2010 Jul; 84(13):6782-98. doi: 10.1128/jvi.01757-09. [PMID: 20335253]
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  • Tetsuo Mashima, Shigeo Sato, Sachiko Okabe, Satoshi Miyata, Masaaki Matsuura, Yoshikazu Sugimoto, Takashi Tsuruo, Hiroyuki Seimiya. Acyl-CoA synthetase as a cancer survival factor: its inhibition enhances the efficacy of etoposide. Cancer science. 2009 Aug; 100(8):1556-62. doi: 10.1111/j.1349-7006.2009.01203.x. [PMID: 19459852]
  • K A R Tobin, G M Johnsen, A C Staff, A K Duttaroy. Long-chain polyunsaturated fatty acid transport across human placental choriocarcinoma (BeWo) cells. Placenta. 2009 Jan; 30(1):41-7. doi: 10.1016/j.placenta.2008.10.007. [PMID: 19010540]
  • Daisuke Matsuda, Ichiji Namatame, Taichi Ohshiro, Shun Ishibashi, Satoshi Omura, Hiroshi Tomoda. Anti-atherosclerotic activity of triacsin C, an acyl-CoA synthetase inhibitor. The Journal of antibiotics. 2008 May; 61(5):318-21. doi: 10.1038/ja.2008.45. [PMID: 18653998]
  • Penny Y T Wang, Liora Caspi, Carol K L Lam, Madhu Chari, Xiaosong Li, Peter E Light, Roger Gutierrez-Juarez, Michelle Ang, Gary J Schwartz, Tony K T Lam. Upper intestinal lipids trigger a gut-brain-liver axis to regulate glucose production. Nature. 2008 Apr; 452(7190):1012-6. doi: 10.1038/nature06852. [PMID: 18401341]
  • Frederique Diraison, Magalie A Ravier, Sarah K Richards, Richard M Smith, Hitoshi Shimano, Guy A Rutter. SREBP1 is required for the induction by glucose of pancreatic beta-cell genes involved in glucose sensing. Journal of lipid research. 2008 Apr; 49(4):814-22. doi: 10.1194/jlr.m700533-jlr200. [PMID: 18178930]
  • Yasuyuki Fujimoto, Jun Onoduka, Koichi J Homma, Shinji Yamaguchi, Masahiro Mori, Yusuke Higashi, Minoru Makita, Tetsuaki Kinoshita, Jun-ichi Noda, Hiroyuki Itabe, Tatsuya Takanoa. Long-chain fatty acids induce lipid droplet formation in a cultured human hepatocyte in a manner dependent of Acyl-CoA synthetase. Biological & pharmaceutical bulletin. 2006 Nov; 29(11):2174-80. doi: 10.1248/bpb.29.2174. [PMID: 17077510]
  • Wen Guo, Nasi Huang, Jun Cai, Weisheng Xie, James A Hamilton. Fatty acid transport and metabolism in HepG2 cells. American journal of physiology. Gastrointestinal and liver physiology. 2006 Mar; 290(3):G528-34. doi: 10.1152/ajpgi.00386.2005. [PMID: 16254047]
  • Yutaka Masuda, Hiroyuki Itabe, Miho Odaki, Kotaro Hama, Yasuyuki Fujimoto, Masahiro Mori, Naoko Sasabe, Junken Aoki, Hiroyuki Arai, Tatsuya Takano. ADRP/adipophilin is degraded through the proteasome-dependent pathway during regression of lipid-storing cells. Journal of lipid research. 2006 Jan; 47(1):87-98. doi: 10.1194/jlr.m500170-jlr200. [PMID: 16230742]
  • Yutong Wang, John F Oram. Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway. The Journal of biological chemistry. 2005 Oct; 280(43):35896-903. doi: 10.1074/jbc.m506210200. [PMID: 16118212]
  • Tony K T Lam, Alessandro Pocai, Roger Gutierrez-Juarez, Silvana Obici, Joseph Bryan, Lydia Aguilar-Bryan, Gary J Schwartz, Luciano Rossetti. Hypothalamic sensing of circulating fatty acids is required for glucose homeostasis. Nature medicine. 2005 Mar; 11(3):320-7. doi: 10.1038/nm1201. [PMID: 15735652]
  • Theresa J Grove, Bruce D Sidell. Fatty acyl CoA synthetase from Antarctic notothenioid fishes may influence substrate specificity of fat oxidation. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2004 Sep; 139(1):53-63. doi: 10.1016/j.cbpc.2004.06.005. [PMID: 15364288]
  • Angela M Hall, Anne J Smith, David A Bernlohr. Characterization of the Acyl-CoA synthetase activity of purified murine fatty acid transport protein 1. The Journal of biological chemistry. 2003 Oct; 278(44):43008-13. doi: 10.1074/jbc.m306575200. [PMID: 12937175]
  • Egidio Iorio, Massimo Di Vito, Francesca Spadaro, Carlo Ramoni, Emanuela Lococo, Roberto Carnevale, Luisa Lenti, Roberto Strom, Franca Podo. Triacsin C inhibits the formation of 1H NMR-visible mobile lipids and lipid bodies in HuT 78 apoptotic cells. Biochimica et biophysica acta. 2003 Oct; 1634(1-2):1-14. doi: 10.1016/j.bbalip.2003.07.001. [PMID: 14563408]
  • Nathan E Wolins, James R Skinner, Marissa J Schoenfish, Anatoly Tzekov, Kenneth G Bensch, Perry E Bickel. Adipocyte protein S3-12 coats nascent lipid droplets. The Journal of biological chemistry. 2003 Sep; 278(39):37713-21. doi: 10.1074/jbc.m304025200. [PMID: 12840023]
  • Neale D Ridgway, Thomas A Lagace. Regulation of the CDP-choline pathway by sterol regulatory element binding proteins involves transcriptional and post-transcriptional mechanisms. The Biochemical journal. 2003 Jun; 372(Pt 3):811-9. doi: 10.1042/bj20030252. [PMID: 12659631]
  • Hae Jin Kee, Jeong Tae Koh, Sung Yeul Yang, Zang Hee Lee, Yung Hong Baik, Kyung Keun Kim. A novel murine long-chain acyl-CoA synthetase expressed in brain participates in neuronal cell proliferation. Biochemical and biophysical research communications. 2003 Jun; 305(4):925-33. doi: 10.1016/s0006-291x(03)00859-3. [PMID: 12767919]
  • Takeo Arai, Yasushi Kawakami, Teruhiko Matsushima, Yukichi Okuda, Kamejiro Yamashita. Intracellular fatty acid downregulates ob gene expression in 3T3-L1 adipocytes. Biochemical and biophysical research communications. 2002 Oct; 297(5):1291-6. doi: 10.1016/s0006-291x(02)02376-8. [PMID: 12372428]
  • Grant M Hatch, Anne J Smith, Fred Y Xu, Angela M Hall, David A Bernlohr. FATP1 channels exogenous FA into 1,2,3-triacyl-sn-glycerol and down-regulates sphingomyelin and cholesterol metabolism in growing 293 cells. Journal of lipid research. 2002 Sep; 43(9):1380-9. doi: 10.1194/jlr.m200130-jlr200. [PMID: 12235169]
  • Agatha Cabrero, Marta Alegret, Rosa M Sanchez, Tomas Adzet, Juan C Laguna, Manuel Vazquez Carrera. Increased reactive oxygen species production down-regulates peroxisome proliferator-activated alpha pathway in C2C12 skeletal muscle cells. The Journal of biological chemistry. 2002 Mar; 277(12):10100-7. doi: 10.1074/jbc.m110321200. [PMID: 11792699]
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