Cerulenin (BioDeep_00000400369)

Main id: BioDeep_00000003559

 

natural product Chemicals and Drugs


代谢物信息卡片


cis-2-epoxy-4-oxo-7E,10E-dodecadienamide

化学式: C12H17NO3 (223.1208372)
中文名称: 变蓝菌素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(C1OC1C(=O)CC/C=C/C/C=C/C)(=O)N
InChI: InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+

描述信息

An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.
D000963 - Antimetabolites > D000960 - Hypolipidemic Agents > D054872 - Fatty Acid Synthesis Inhibitors
D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
D009676 - Noxae > D000963 - Antimetabolites
Cerulenin, a potent, natural inhibitor of fatty acid synthase (FASN), is an epoxide produced by the fungus Cephalosporium caeruleus. Cerulenin inhibits topoisomerase I catalytic activity and augments SN-38-induced apoptosis. Cerulenin has antifungal and antitumor activies[1][2][3][4].
Cerulenin, a potent, natural inhibitor of fatty acid synthase (FASN), is an epoxide produced by the fungus Cephalosporium caeruleus. Cerulenin inhibits topoisomerase I catalytic activity and augments SN-38-induced apoptosis. Cerulenin has antifungal and antitumor activies[1][2][3][4].

同义名列表

3 个代谢物同义名

Cerulenin; cis-2-epoxy-4-oxo-7E,10E-dodecadienamide; Cerulenin



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

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)

2 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

  • Dongxiao Liu, Ruth Cruz-Cosme, Yong Wu, Julian Leibowitz, Qiyi Tang. 2-Bromopalmitate depletes lipid droplets to inhibit viral replication. Journal of virology. 2024 Apr; 98(4):e0017124. doi: 10.1128/jvi.00171-24. [PMID: 38488361]
  • Azza Troudi, Jean Marie Pagès, Jean Michel Brunel. Chemical Highlights Supporting the Role of Lipid A in Efficient Biological Adaptation of Gram-Negative Bacteria to External Stresses. Journal of medicinal chemistry. 2021 02; 64(4):1816-1834. doi: 10.1021/acs.jmedchem.0c02185. [PMID: 33538159]
  • Kaat José Peeters, Ashley Haeck, Lies Harinck, Oluwatoyin Oluwakemi Afolabi, Kristof Demeestere, Kris Audenaert, Monica Höfte. Morphological, Pathogenic and Toxigenic Variability in the Rice Sheath Rot Pathogen Sarocladium Oryzae. Toxins. 2020 02; 12(2):. doi: 10.3390/toxins12020109. [PMID: 32046323]
  • Qingwei Yao, Haiqin Chen, Shunxian Wang, Xin Tang, Zhennan Gu, Hao Zhang, Wei Chen, Yong Q Chen. An efficient strategy for screening polyunsaturated fatty acid-producing oleaginous filamentous fungi from soil. Journal of microbiological methods. 2019 03; 158(?):80-85. doi: 10.1016/j.mimet.2018.12.023. [PMID: 30708087]
  • Luis Gonzaga Heredia-Martínez, Ascensión Andrés-Garrido, Enrique Martínez-Force, María Esther Pérez-Pérez, José L Crespo. Chloroplast Damage Induced by the Inhibition of Fatty Acid Synthesis Triggers Autophagy in Chlamydomonas. Plant physiology. 2018 11; 178(3):1112-1129. doi: 10.1104/pp.18.00630. [PMID: 30181343]
  • Katharina Stoiber, Olga Nagło, Carla Pernpeintner, Siwei Zhang, Andreas Koeberle, Melanie Ulrich, Oliver Werz, Rolf Müller, Stefan Zahler, Theobald Lohmüller, Jochen Feldmann, Simone Braig. Targeting de novo lipogenesis as a novel approach in anti-cancer therapy. British journal of cancer. 2018 01; 118(1):43-51. doi: 10.1038/bjc.2017.374. [PMID: 29112683]
  • Daryl L Richie, Lisha Wang, Helen Chan, Gianfranco De Pascale, David A Six, Jun-Rong Wei, Charles R Dean. A pathway-directed positive growth restoration assay to facilitate the discovery of lipid A and fatty acid biosynthesis inhibitors in Acinetobacter baumannii. PloS one. 2018; 13(3):e0193851. doi: 10.1371/journal.pone.0193851. [PMID: 29505586]
  • Hanaa Hariri, Sean Rogers, Rupali Ugrankar, Yang Lydia Liu, J Ryan Feathers, W Mike Henne. Lipid droplet biogenesis is spatially coordinated at ER-vacuole contacts under nutritional stress. EMBO reports. 2018 01; 19(1):57-72. doi: 10.15252/embr.201744815. [PMID: 29146766]
  • Jamie Royle, Claire L Donald, Andres Merits, Alain Kohl, Margus Varjak. Differential effects of lipid biosynthesis inhibitors on Zika and Semliki Forest viruses. Veterinary journal (London, England : 1997). 2017 Dec; 230(?):62-64. doi: 10.1016/j.tvjl.2017.10.009. [PMID: 29102599]
  • Gouri Katre, Namasvi Ajmera, Smita Zinjarde, Ameeta RaviKumar. Mutants of Yarrowia lipolytica NCIM 3589 grown on waste cooking oil as a biofactory for biodiesel production. Microbial cell factories. 2017 Oct; 16(1):176. doi: 10.1186/s12934-017-0790-x. [PMID: 29065878]
  • Sergio A Mojica, Olli Salin, Robert J Bastidas, Naresh Sunduru, Mattias Hedenström, C David Andersson, Carlos Núñez-Otero, Patrik Engström, Raphael H Valdivia, Mikael Elofsson, Åsa Gylfe. N-Acylated Derivatives of Sulfamethoxazole Block Chlamydia Fatty Acid Synthesis and Interact with FabF. Antimicrobial agents and chemotherapy. 2017 10; 61(10):. doi: 10.1128/aac.00716-17. [PMID: 28784680]
  • Gabriela Seydlová, Radek Pohl, Eva Zborníková, Marcel Ehn, Ondřej Šimák, Natalya Panova, Milan Kolář, Kateřina Bogdanová, Renata Večeřová, Radovan Fišer, Hana Šanderová, Dragana Vítovská, Petra Sudzinová, Jiří Pospíšil, Oldřich Benada, Tomáš Křížek, David Sedlák, Petr Bartůněk, Libor Krásný, Dominik Rejman. Lipophosphonoxins II: Design, Synthesis, and Properties of Novel Broad Spectrum Antibacterial Agents. Journal of medicinal chemistry. 2017 07; 60(14):6098-6118. doi: 10.1021/acs.jmedchem.7b00355. [PMID: 28654257]
  • Jonathan D Nickels, Sneha Chatterjee, Christopher B Stanley, Shuo Qian, Xiaolin Cheng, Dean A A Myles, Robert F Standaert, James G Elkins, John Katsaras. The in vivo structure of biological membranes and evidence for lipid domains. PLoS biology. 2017 05; 15(5):e2002214. doi: 10.1371/journal.pbio.2002214. [PMID: 28542493]
  • André A Pulschen, Diego E Sastre, Federico Machinandiarena, Agostina Crotta Asis, Daniela Albanesi, Diego de Mendoza, Frederico J Gueiros-Filho. The stringent response plays a key role in Bacillus subtilis survival of fatty acid starvation. Molecular microbiology. 2017 02; 103(4):698-712. doi: 10.1111/mmi.13582. [PMID: 27875634]
  • Koji Nishi, Kenta Suzuki, Junpei Sawamoto, Yuma Tokizawa, Yumiko Iwase, Nagahiko Yumita, Toshihiko Ikeda. Inhibition of Fatty Acid Synthesis Induces Apoptosis of Human Pancreatic Cancer Cells. Anticancer research. 2016 09; 36(9):4655-60. doi: 10.21873/anticanres.11016. [PMID: 27630308]
  • Shailaja Hittalmani, H B Mahesh, Channappa Mahadevaiah, Mothukapalli Krishnareddy Prasannakumar. De novo genome assembly and annotation of rice sheath rot fungus Sarocladium oryzae reveals genes involved in Helvolic acid and Cerulenin biosynthesis pathways. BMC genomics. 2016 Mar; 17(?):271. doi: 10.1186/s12864-016-2599-0. [PMID: 27036298]
  • Xia Wan, Yun-Feng Peng, Xue-Rong Zhou, Yang-Min Gong, Feng-Hong Huang, Gabriel Moncalián. Effect of cerulenin on fatty acid composition and gene expression pattern of DHA-producing strain Colwellia psychrerythraea strain 34H. Microbial cell factories. 2016 Feb; 15(?):30. doi: 10.1186/s12934-016-0431-9. [PMID: 26852325]
  • Yun-Feng Peng, Wen-Chao Chen, Kang Xiao, Lin Xu, Lian Wang, Xia Wan. DHA Production in Escherichia coli by Expressing Reconstituted Key Genes of Polyketide Synthase Pathway from Marine Bacteria. PloS one. 2016; 11(9):e0162861. doi: 10.1371/journal.pone.0162861. [PMID: 27649078]
  • Yuki Yasumoto, Hirofumi Miyazaki, Linda Koshy Vaidyan, Yoshiteru Kagawa, Majid Ebrahimi, Yui Yamamoto, Masaki Ogata, Yu Katsuyama, Hirokazu Sadahiro, Michiyasu Suzuki, Yuji Owada. Inhibition of Fatty Acid Synthase Decreases Expression of Stemness Markers in Glioma Stem Cells. PloS one. 2016; 11(1):e0147717. doi: 10.1371/journal.pone.0147717. [PMID: 26808816]
  • Masayoshi Hashimoto, Ken Komatsu, Ryo Iwai, Takuya Keima, Kensaku Maejima, Takuya Shiraishi, Kazuya Ishikawa, Tetsuya Yoshida, Yugo Kitazawa, Yukari Okano, Yasuyuki Yamaji, Shigetou Namba. Cell Death Triggered by a Putative Amphipathic Helix of Radish mosaic virus Helicase Protein Is Tightly Correlated With Host Membrane Modification. Molecular plant-microbe interactions : MPMI. 2015 Jun; 28(6):675-88. doi: 10.1094/mpmi-01-15-0004-r. [PMID: 25650831]
  • Lucía Porrini, Larisa E Cybulski, Silvia G Altabe, María C Mansilla, Diego de Mendoza. Cerulenin inhibits unsaturated fatty acids synthesis in Bacillus subtilis by modifying the input signal of DesK thermosensor. MicrobiologyOpen. 2014 Apr; 3(2):213-24. doi: 10.1002/mbo3.154. [PMID: 24574048]
  • Joonseok Oh, In Hyun Hwang, Chang-Eui Hong, Su-Yun Lyu, MinKyun Na. Inhibition of fatty acid synthase by ginkgolic acids from the leaves of Ginkgo biloba and their cytotoxic activity. Journal of enzyme inhibition and medicinal chemistry. 2013 Jun; 28(3):565-8. doi: 10.3109/14756366.2012.658786. [PMID: 22380770]
  • Vadim Degtyar, Ismail M Hafez, Christopher Bray, Robert S Zucker. Dance of the SNAREs: assembly and rearrangements detected with FRET at neuronal synapses. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2013 Mar; 33(13):5507-23. doi: 10.1523/jneurosci.2337-12.2013. [PMID: 23536066]
  • Annarita Ciana, Cesare Achilli, Rami N Hannoush, Angela Risso, Cesare Balduini, Giampaolo Minetti. Freely turning over palmitate in erythrocyte membrane proteins is not responsible for the anchoring of lipid rafts to the spectrin skeleton: a study with bio-orthogonal chemical probes. Biochimica et biophysica acta. 2013 Mar; 1828(3):924-31. doi: 10.1016/j.bbamem.2012.11.029. [PMID: 23219804]
  • Gang Cheng, Arun P Palanisamy, Zachary P Evans, Alton G Sutter, Lan Jin, Inderjit Singh, Harold May, Michael G Schmidt, Kenneth D Chavin. Cerulenin blockade of fatty acid synthase reverses hepatic steatosis in ob/ob mice. PloS one. 2013; 8(9):e75980. doi: 10.1371/journal.pone.0075980. [PMID: 24086674]
  • Perinkulam Ravi Deepa, Suryanarayanan Vandhana, Subramanian Krishnakumar. Fatty acid synthase inhibition induces differential expression of genes involved in apoptosis and cell proliferation in ocular cancer cells. Nutrition and cancer. 2013; 65(2):311-6. doi: 10.1080/01635581.2013.748923. [PMID: 23441619]
  • Li-Hsueh Wang, Hsieh-He Lee, Lee-Shing Fang, Anderson B Mayfield, Chii-Shiarng Chen. Fatty acid and phospholipid syntheses are prerequisites for the cell cycle of Symbiodinium and their endosymbiosis within sea anemones. PloS one. 2013; 8(8):e72486. doi: 10.1371/journal.pone.0072486. [PMID: 24009685]
  • Maria Francesca Santolla, Rosamaria Lappano, Paola De Marco, Marco Pupo, Adele Vivacqua, Diego Sisci, Sergio Abonante, Domenico Iacopetta, Anna Rita Cappello, Vincenza Dolce, Marcello Maggiolini. G protein-coupled estrogen receptor mediates the up-regulation of fatty acid synthase induced by 17β-estradiol in cancer cells and cancer-associated fibroblasts. The Journal of biological chemistry. 2012 Dec; 287(52):43234-45. doi: 10.1074/jbc.m112.417303. [PMID: 23135268]
  • Dai Tian, Yanyan Qiu, Yongkun Zhan, Xiaobo Li, Xiuling Zhi, Xinhong Wang, Lianhua Yin, Yanxia Ning. Overexpression of steroidogenic acute regulatory protein in rat aortic endothelial cells attenuates palmitic acid-induced inflammation and reduction in nitric oxide bioavailability. Cardiovascular diabetology. 2012 Nov; 11(?):144. doi: 10.1186/1475-2840-11-144. [PMID: 23170972]
  • Giacomo Zara, Paola Goffrini, Tiziana Lodi, Severino Zara, Ilaria Mannazzu, Marilena Budroni. FLO11 expression and lipid biosynthesis are required for air-liquid biofilm formation in a Saccharomyces cerevisiae flor strain. FEMS yeast research. 2012 Nov; 12(7):864-6. doi: 10.1111/j.1567-1364.2012.00831.x. [PMID: 22805178]
  • Perinkulam Ravi Deepa, Suryanarayanan Vandhana, Udayakumar Jayanthi, Subramanian Krishnakumar. Therapeutic and toxicologic evaluation of anti-lipogenic agents in cancer cells compared with non-neoplastic cells. Basic & clinical pharmacology & toxicology. 2012 Jun; 110(6):494-503. doi: 10.1111/j.1742-7843.2011.00844.x. [PMID: 22151915]
  • 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]
  • Walentyna Banaś, Tomasz Furmanek, Antoni Banaś. Effect of haloxyfop and cerulenin on de novo biosynthesis of lipids in roots of wheat and maize. Acta biochimica Polonica. 2012; 59(4):567-73. doi: . [PMID: 23189275]
  • Kent Sakai, Nobuhiro Koyama, Takashi Fukuda, Yukiko Mori, Hiroyasu Onaka, Hiroshi Tomoda. Search method for inhibitors of Staphyloxanthin production by methicillin-resistant Staphylococcus aureus. Biological & pharmaceutical bulletin. 2012; 35(1):48-53. doi: 10.1248/bpb.35.48. [PMID: 22223336]
  • José Manuel Tirado-Vélez, Insaf Joumady, Ana Sáez-Benito, Irene Cózar-Castellano, Germán Perdomo. Inhibition of fatty acid metabolism reduces human myeloma cells proliferation. PloS one. 2012; 7(9):e46484. doi: 10.1371/journal.pone.0046484. [PMID: 23029529]
  • Long Nam Nguyen, Joshua D Nosanchuk. Lipid droplet formation protects against gluco/lipotoxicity in Candida parapsilosis: an essential role of fatty acid desaturase Ole1. Cell cycle (Georgetown, Tex.). 2011 Sep; 10(18):3159-67. doi: 10.4161/cc.10.18.16932. [PMID: 21897120]
  • Stylianos Fakas, Chrysanthos Konstantinou, George M Carman. DGK1-encoded diacylglycerol kinase activity is required for phospholipid synthesis during growth resumption from stationary phase in Saccharomyces cerevisiae. The Journal of biological chemistry. 2011 Jan; 286(2):1464-74. doi: 10.1074/jbc.m110.194308. [PMID: 21071438]
  • Miguel López, Luis Varela, María J Vázquez, Sergio Rodríguez-Cuenca, Carmen R González, Vidya R Velagapudi, Donald A Morgan, Erik Schoenmakers, Khristofor Agassandian, Ricardo Lage, Pablo Blanco Martínez de Morentin, Sulay Tovar, Rubén Nogueiras, David Carling, Christopher Lelliott, Rosalía Gallego, Matej Oresic, Krishna Chatterjee, Asish K Saha, Kamal Rahmouni, Carlos Diéguez, Antonio Vidal-Puig. Hypothalamic AMPK and fatty acid metabolism mediate thyroid regulation of energy balance. Nature medicine. 2010 Sep; 16(9):1001-8. doi: 10.1038/nm.2207. [PMID: 20802499]
  • Polina Shindiapina, Charles Barlowe. Requirements for transitional endoplasmic reticulum site structure and function in Saccharomyces cerevisiae. Molecular biology of the cell. 2010 May; 21(9):1530-45. doi: 10.1091/mbc.e09-07-0605. [PMID: 20200224]
  • E Ons, A Gertler, J Buyse, E Lebihan-Duval, A Bordas, B Goddeeris, S Dridi. Visfatin gene expression in chickens is sex and tissue dependent. Domestic animal endocrinology. 2010 Feb; 38(2):63-74. doi: 10.1016/j.domaniend.2009.08.007. [PMID: 19786337]
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  • Devinka Bamunusinghe, Cynthia L Hemenway, Richard S Nelson, Anton A Sanderfoot, Chang M Ye, Muniwarage A T Silva, M Payton, Jeanmarie Verchot-Lubicz. Analysis of potato virus X replicase and TGBp3 subcellular locations. Virology. 2009 Oct; 393(2):272-85. doi: 10.1016/j.virol.2009.08.002. [PMID: 19729179]
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  • Patrik Johansson, Birgit Wiltschi, Preeti Kumari, Brigitte Kessler, Clemens Vonrhein, Janet Vonck, Dieter Oesterhelt, Martin Grininger. Inhibition of the fungal fatty acid synthase type I multienzyme complex. Proceedings of the National Academy of Sciences of the United States of America. 2008 Sep; 105(35):12803-8. doi: 10.1073/pnas.0805827105. [PMID: 18725634]
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