Enterobactin (BioDeep_00000409553)

Main id: BioDeep_00000004282

 

natural product


代谢物信息卡片


Enterobactin

化学式: C30H27N3O15 (669.1442112000001)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C(C(=O)OCC(C(=O)OCC(C(=O)O1)NC(=O)C2=C(C(=CC=C2)O)O)NC(=O)C3=C(C(=CC=C3)O)O)NC(=O)C4=C(C(=CC=C4)O)O
InChI: InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1

描述信息

A macrotriolide produced by certain members of Enterobacteriaceae, e.g. Escherichia coli and Salmonella.
D064449 - Sequestering Agents > D002614 - Chelating Agents > D007502 - Iron Chelating Agents

同义名列表

1 个代谢物同义名

Enterobactin



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

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)

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

  • Alexandra Canciu, Andreea Cernat, Mihaela Tertis, Silvia Botarca, Madalina Adriana Bordea, Joseph Wang, Cecilia Cristea. Proof of Concept for the Detection with Custom Printed Electrodes of Enterobactin as a Marker of Escherichia coli. International journal of molecular sciences. 2022 Aug; 23(17):. doi: 10.3390/ijms23179884. [PMID: 36077283]
  • Chuchu Guo, Elizabeth M Nolan. Heavy-Metal Trojan Horse: Enterobactin-Directed Delivery of Platinum(IV) Prodrugs to Escherichia coli. Journal of the American Chemical Society. 2022 07; 144(28):12756-12768. doi: 10.1021/jacs.2c03324. [PMID: 35803281]
  • Arwen E Frick-Cheng, Anna Sintsova, Sara N Smith, Ali Pirani, Evan S Snitkin, Harry L T Mobley. Ferric Citrate Uptake Is a Virulence Factor in Uropathogenic Escherichia coli. mBio. 2022 06; 13(3):e0103522. doi: 10.1128/mbio.01035-22. [PMID: 35546538]
  • Ashish Kumar, Taihao Yang, Somnath Chakravorty, Aritri Majumdar, Brittany L Nairn, David A Six, Naara Marcondes Dos Santos, Sarah L Price, Matthew B Lawrenz, Luis A Actis, Marilis Marques, Thomas A Russo, Salete M Newton, Phillip E Klebba. Fluorescent sensors of siderophores produced by bacterial pathogens. The Journal of biological chemistry. 2022 03; 298(3):101651. doi: 10.1016/j.jbc.2022.101651. [PMID: 35101443]
  • Vladimir Gorshkov, Olga Parfirova, Olga Petrova, Natalia Gogoleva, Evgeny Kovtunov, Vladimir Vorob'ev, Yuri Gogolev. The Knockout of Enterobactin-Related Gene in Pectobacterium atrosepticum Results in Reduced Stress Resistance and Virulence towards the Primed Plants. International journal of molecular sciences. 2021 Sep; 22(17):. doi: 10.3390/ijms22179594. [PMID: 34502502]
  • Qihao Wu, Kurt Throckmorton, Mitasree Maity, Marc G Chevrette, Doug R Braun, Scott R Rajski, Cameron R Currie, Michael G Thomas, Tim S Bugni. Bacillibactins E and F from a Marine Sponge-Associated Bacillus sp. Journal of natural products. 2021 01; 84(1):136-141. doi: 10.1021/acs.jnatprod.0c01170. [PMID: 33337146]
  • Ximin Zeng, Huiwen Wang, Canghai Huang, Catherine M Logue, Nicolle L Barbieri, Lisa K Nolan, Jun Lin. Evaluation of the Immunogenic Response of a Novel Enterobactin Conjugate Vaccine in Chickens for the Production of Enterobactin-Specific Egg Yolk Antibodies. Frontiers in immunology. 2021; 12(?):629480. doi: 10.3389/fimmu.2021.629480. [PMID: 33868248]
  • Piu Saha, Beng San Yeoh, Xia Xiao, Rachel M Golonka, Ahmed A Abokor, Camilla F Wenceslau, Yatrik M Shah, Bina Joe, Matam Vijay-Kumar. Enterobactin induces the chemokine, interleukin-8, from intestinal epithelia by chelating intracellular iron. Gut microbes. 2020 11; 12(1):1-18. doi: 10.1080/19490976.2020.1841548. [PMID: 33171063]
  • Hari Parapatla, Ramurthy Gudla, Guruprasad Varma Konduru, Elsin Raju Devadasu, Hampapathula Adimurthy Nagarajaram, Manjula Sritharan, Rajagopal Subramanyam, Dayananda Siddavattam. Organophosphate hydrolase interacts with ferric-enterobactin and promotes iron uptake in association with TonB-dependent transport system. The Biochemical journal. 2020 08; 477(15):2821-2840. doi: 10.1042/bcj20200299. [PMID: 32686828]
  • Clémence Massip, Camille V Chagneau, Michèle Boury, Eric Oswald. The synergistic triad between microcin, colibactin, and salmochelin gene clusters in uropathogenic Escherichia coli. Microbes and infection. 2020 04; 22(3):144-147. doi: 10.1016/j.micinf.2020.01.001. [PMID: 31954842]
  • Edyta Konecka, Joanna Mokracka, Sylwia Krzymińska, Adam Kaznowski. Evaluation of The Pathogenic Potential of Insecticidal Serratia marcescens Strains to Humans. Polish journal of microbiology. 2019; 68(2):185-191. doi: 10.21307/pjm-2019-018. [PMID: 31257791]
  • Jérémy Esque, Mark S P Sansom, Marc Baaden, Christophe Oguey. Analyzing protein topology based on Laguerre tessellation of a pore-traversing water network. Scientific reports. 2018 09; 8(1):13540. doi: 10.1038/s41598-018-31422-5. [PMID: 30202114]
  • M Moreno, A Zacarias, A Porzel, L Velasquez, G Gonzalez, M Alegría-Arcos, F Gonzalez-Nilo, E K U Gross. IR and NMR spectroscopic correlation of enterobactin by DFT. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2018 Jun; 198(?):264-277. doi: 10.1016/j.saa.2018.02.060. [PMID: 29550657]
  • Akira Ishii, Goro Katsuura, Hirotaka Imamaki, Hiroyuki Kimura, Keita P Mori, Takashige Kuwabara, Masato Kasahara, Hideki Yokoi, Kousaku Ohinata, Tomoko Kawanishi, Junichi Tsuchida, Yuji Nakamoto, Kazuwa Nakao, Motoko Yanagita, Masashi Mukoyama, Kiyoshi Mori. Obesity-promoting and anti-thermogenic effects of neutrophil gelatinase-associated lipocalin in mice. Scientific reports. 2017 Nov; 7(1):15501. doi: 10.1038/s41598-017-15825-4. [PMID: 29138470]
  • Halit Kuş, Uğur Arslan, Hatice Türk Dağı, Duygu Fındık. [Investigation of various virulence factors of Klebsiella pneumoniae strains isolated from nosocomial infections]. Mikrobiyoloji bulteni. 2017 Oct; 51(4):329-339. doi: 10.5578/mb.59716. [PMID: 29153063]
  • Thomas A Russo, Ruth Olson, Ulrike MacDonald, Janet Beanan, Bruce A Davidson. Aerobactin, but not yersiniabactin, salmochelin, or enterobactin, enables the growth/survival of hypervirulent (hypermucoviscous) Klebsiella pneumoniae ex vivo and in vivo. Infection and immunity. 2015 Aug; 83(8):3325-33. doi: 10.1128/iai.00430-15. [PMID: 26056379]
  • Robin R Shields-Cutler, Jan R Crowley, Chia S Hung, Ann E Stapleton, Courtney C Aldrich, Jonas Marschall, Jeffrey P Henderson. Human Urinary Composition Controls Antibacterial Activity of Siderocalin. The Journal of biological chemistry. 2015 Jun; 290(26):15949-60. doi: 10.1074/jbc.m115.645812. [PMID: 25861985]
  • Laura J Searle, Guillaume Méric, Ida Porcelli, Samuel K Sheppard, Sacha Lucchini. Variation in siderophore biosynthetic gene distribution and production across environmental and faecal populations of Escherichia coli. PloS one. 2015; 10(3):e0117906. doi: 10.1371/journal.pone.0117906. [PMID: 25756870]
  • Timothée J N Kenla, Michel D Kongue Tatong, Ferdinand Mouafo Talontsi, Birger Dittrich, Holm Frauendorf, Hartmut Laatsch. Si-enterobactin from the endophytic Streptomyces sp. KT-S1-B5--a potential silicon transporter in Nature?. Chemical communications (Cambridge, England). 2013 Sep; 49(69):7641-3. doi: 10.1039/c3cc44437f. [PMID: 23872808]
  • Neal Paragas, Andong Qiu, Maria Hollmen, Thomas L Nickolas, Prasad Devarajan, Jonathan Barasch. NGAL-Siderocalin in kidney disease. Biochimica et biophysica acta. 2012 Sep; 1823(9):1451-8. doi: 10.1016/j.bbamcr.2012.06.014. [PMID: 22728330]
  • Lavanya Babujee, Jennifer Apodaca, Venkatesh Balakrishnan, Paul Liss, Patricia J Kiley, Amy O Charkowski, Jeremy D Glasner, Nicole T Perna. Evolution of the metabolic and regulatory networks associated with oxygen availability in two phytopathogenic enterobacteria. BMC genomics. 2012 Mar; 13(?):110. doi: 10.1186/1471-2164-13-110. [PMID: 22439737]
  • Theodore J Zwang, Michael V Gormally, Malkiat S Johal, Matthew H Sazinsky. Enhanced iron availability by protein glycation may explain higher infection rates in diabetics. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine. 2012 Feb; 25(1):237-45. doi: 10.1007/s10534-011-9492-8. [PMID: 21901551]
  • Kristin I Miller, Chen Qing, Daniel Man Yuen Sze, Brett A Neilan. Investigation of the biosynthetic potential of endophytes in traditional Chinese anticancer herbs. PloS one. 2012; 7(5):e35953. doi: 10.1371/journal.pone.0035953. [PMID: 22629306]
  • Senthilkumar Palaniyandi, Arindam Mitra, Christopher D Herren, C Virginia Lockatell, David E Johnson, Xiaoping Zhu, Suman Mukhopadhyay. BarA-UvrY two-component system regulates virulence of uropathogenic E. coli CFT073. PloS one. 2012; 7(2):e31348. doi: 10.1371/journal.pone.0031348. [PMID: 22363626]
  • Geetha Rajendran, Maheshwari H Patel, Sanket J Joshi. Isolation and Characterization of Nodule-Associated Exiguobacterium sp. from the Root Nodules of Fenugreek (Trigonella foenum-graecum) and Their Possible Role in Plant Growth Promotion. International journal of microbiology. 2012; 2012(?):693982. doi: 10.1155/2012/693982. [PMID: 22518149]
  • Jessica W Greenwald, Charles J Greenwald, Benjamin J Philmus, Tadhg P Begley, Dennis C Gross. RNA-seq analysis reveals that an ECF σ factor, AcsS, regulates achromobactin biosynthesis in Pseudomonas syringae pv. syringae B728a. PloS one. 2012; 7(4):e34804. doi: 10.1371/journal.pone.0034804. [PMID: 22529937]
  • Sierra L Hartney, Sylvie Mazurier, Teresa A Kidarsa, Maria Carolina Quecine, Philippe Lemanceau, Joyce E Loper. TonB-dependent outer-membrane proteins and siderophore utilization in Pseudomonas fluorescens Pf-5. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine. 2011 Apr; 24(2):193-213. doi: 10.1007/s10534-010-9385-2. [PMID: 21080032]
  • Jian Wang, Kostas Pantopoulos. Regulation of cellular iron metabolism. The Biochemical journal. 2011 Mar; 434(3):365-81. doi: 10.1042/bj20101825. [PMID: 21348856]
  • Neeraja Vajrala, Luis A Sayavedra-Soto, Peter J Bottomley, Daniel J Arp. Role of a Fur homolog in iron metabolism in Nitrosomonas europaea. BMC microbiology. 2011 Feb; 11(?):37. doi: 10.1186/1471-2180-11-37. [PMID: 21338516]
  • Simone Marcelletti, Patrizia Ferrante, Milena Petriccione, Giuseppe Firrao, Marco Scortichini. Pseudomonas syringae pv. actinidiae draft genomes comparison reveal strain-specific features involved in adaptation and virulence to Actinidia species. PloS one. 2011; 6(11):e27297. doi: 10.1371/journal.pone.0027297. [PMID: 22132095]
  • Thomas A Russo, Alyssa S Shon, Janet M Beanan, Ruth Olson, Ulrike MacDonald, Alexander O Pomakov, Mark P Visitacion. Hypervirulent K. pneumoniae secretes more and more active iron-acquisition molecules than 'classical' K. pneumoniae thereby enhancing its virulence. PloS one. 2011; 6(10):e26734. doi: 10.1371/journal.pone.0026734. [PMID: 22039542]
  • Theo H M Smits, Fabio Rezzonico, Tim Kamber, Jochen Blom, Alexander Goesmann, Carol A Ishimaru, Jürg E Frey, Virginia O Stockwell, Brion Duffy. Metabolic versatility and antibacterial metabolite biosynthesis are distinguishing genomic features of the fire blight antagonist Pantoea vagans C9-1. PloS one. 2011; 6(7):e22247. doi: 10.1371/journal.pone.0022247. [PMID: 21789243]
  • Erin C Hagan, Amanda L Lloyd, David A Rasko, Gary J Faerber, Harry L T Mobley. Escherichia coli global gene expression in urine from women with urinary tract infection. PLoS pathogens. 2010 Nov; 6(11):e1001187. doi: 10.1371/journal.ppat.1001187. [PMID: 21085611]
  • Neeraja Vajrala, Luis A Sayavedra-Soto, Peter J Bottomley, Daniel J Arp. Role of Nitrosomonas europaea NitABC iron transporter in the uptake of Fe3+-siderophore complexes. Archives of microbiology. 2010 Nov; 192(11):899-908. doi: 10.1007/s00203-010-0620-6. [PMID: 20737137]
  • Safiyh Taghavi, Daniel van der Lelie, Adam Hoffman, Yian-Biao Zhang, Michael D Walla, Jaco Vangronsveld, Lee Newman, Sébastien Monchy. Genome sequence of the plant growth promoting endophytic bacterium Enterobacter sp. 638. PLoS genetics. 2010 May; 6(5):e1000943. doi: 10.1371/journal.pgen.1000943. [PMID: 20485560]
  • Sarah Green, David J Studholme, Bridget E Laue, Federico Dorati, Helen Lovell, Dawn Arnold, Joan E Cottrell, Stephen Bridgett, Mark Blaxter, Edgar Huitema, Richard Thwaites, Paul M Sharp, Robert W Jackson, Sophien Kamoun. Comparative genome analysis provides insights into the evolution and adaptation of Pseudomonas syringae pv. aesculi on Aesculus hippocastanum. PloS one. 2010 Apr; 5(4):e10224. doi: 10.1371/journal.pone.0010224. [PMID: 20419105]
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  • Theo H M Smits, Sebastian Jaenicke, Fabio Rezzonico, Tim Kamber, Alexander Goesmann, Jürg E Frey, Brion Duffy. Complete genome sequence of the fire blight pathogen Erwinia pyrifoliae DSM 12163T and comparative genomic insights into plant pathogenicity. BMC genomics. 2010 Jan; 11(?):2. doi: 10.1186/1471-2164-11-2. [PMID: 20047678]
  • Oliver Mirus, Sascha Strauss, Kerstin Nicolaisen, Arndt von Haeseler, Enrico Schleiff. TonB-dependent transporters and their occurrence in cyanobacteria. BMC biology. 2009 Oct; 7(?):68. doi: 10.1186/1741-7007-7-68. [PMID: 19821963]
  • Christopher J Alteri, Erin C Hagan, Kelsey E Sivick, Sara N Smith, Harry L T Mobley. Mucosal immunization with iron receptor antigens protects against urinary tract infection. PLoS pathogens. 2009 Sep; 5(9):e1000586. doi: 10.1371/journal.ppat.1000586. [PMID: 19806177]
  • O Beran, D A Lawrence, N Andersen, O Dzupova, J Kalmusova, M Musilek, M Holub. Sequential analysis of biomarkers in cerebrospinal fluid and serum during invasive meningococcal disease. European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology. 2009 Jul; 28(7):793-9. doi: 10.1007/s10096-009-0708-6. [PMID: 19205764]
  • Joyce C Yang, Ramana Madupu, A Scott Durkin, Nathan A Ekborg, Chandra S Pedamallu, Jessica B Hostetler, Diana Radune, Bradley S Toms, Bernard Henrissat, Pedro M Coutinho, Sandra Schwarz, Lauren Field, Amaro E Trindade-Silva, Carlos A G Soares, Sherif Elshahawi, Amro Hanora, Eric W Schmidt, Margo G Haygood, Janos Posfai, Jack Benner, Catherine Madinger, John Nove, Brian Anton, Kshitiz Chaudhary, Jeremy Foster, Alex Holman, Sanjay Kumar, Philip A Lessard, Yvette A Luyten, Barton Slatko, Nicole Wood, Bo Wu, Max Teplitski, Joseph D Mougous, Naomi Ward, Jonathan A Eisen, Jonathan H Badger, Daniel L Distel. The complete genome of Teredinibacter turnerae T7901: an intracellular endosymbiont of marine wood-boring bivalves (shipworms). PloS one. 2009 Jul; 4(7):e6085. doi: 10.1371/journal.pone.0006085. [PMID: 19568419]
  • Chuck R Smallwood, Amparo Gala Marco, Qiaobin Xiao, Vy Trinh, Salete M C Newton, Phillip E Klebba. Fluoresceination of FepA during colicin B killing: effects of temperature, toxin and TonB. Molecular microbiology. 2009 Jun; 72(5):1171-80. doi: 10.1111/j.1365-2958.2009.06715.x. [PMID: 19432807]
  • Cedric Montanier, Victoria A Money, Virginia M R Pires, James E Flint, Benedita A Pinheiro, Arun Goyal, José A M Prates, Atsushi Izumi, Henrik Stålbrand, Carl Morland, Alan Cartmell, Katarina Kolenova, Evangelos Topakas, Eleanor J Dodson, David N Bolam, Gideon J Davies, Carlos M G A Fontes, Harry J Gilbert. The active site of a carbohydrate esterase displays divergent catalytic and noncatalytic binding functions. PLoS biology. 2009 Mar; 7(3):e71. doi: 10.1371/journal.pbio.1000071. [PMID: 19338387]
  • Philip W Jordan, Nigel J Saunders. Host iron binding proteins acting as niche indicators for Neisseria meningitidis. PloS one. 2009; 4(4):e5198. doi: 10.1371/journal.pone.0005198. [PMID: 19352437]
  • Ulrich Methner, Wolfgang Rabsch, Rolf Reissbrodt, Peter H Williams. Effect of norepinephrine on colonisation and systemic spread of Salmonella enterica in infected animals: role of catecholate siderophore precursors and degradation products. International journal of medical microbiology : IJMM. 2008 Jul; 298(5-6):429-39. doi: 10.1016/j.ijmm.2007.07.013. [PMID: 17888732]
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  • Marine Froissard, Naïma Belgareh-Touzé, Marylène Dias, Nicole Buisson, Jean-Michel Camadro, Rosine Haguenauer-Tsapis, Emmanuel Lesuisse. Trafficking of siderophore transporters in Saccharomyces cerevisiae and intracellular fate of ferrioxamine B conjugates. Traffic (Copenhagen, Denmark). 2007 Nov; 8(11):1601-16. doi: 10.1111/j.1600-0854.2007.00627.x. [PMID: 17714436]
  • Surendranathan Devanathan, Kathleen Postle. Studies on colicin B translocation: FepA is gated by TonB. Molecular microbiology. 2007 Jul; 65(2):441-53. doi: 10.1111/j.1365-2958.2007.05808.x. [PMID: 17578453]
  • Friederike Feldmann, Liisa Johanna Sorsa, Kirsten Hildinger, Sören Schubert. The salmochelin siderophore receptor IroN contributes to invasion of urothelial cells by extraintestinal pathogenic Escherichia coli in vitro. Infection and immunity. 2007 Jun; 75(6):3183-7. doi: 10.1128/iai.00656-06. [PMID: 17353289]
  • Marianne Valdebenito, Alvin L Crumbliss, Günther Winkelmann, Klaus Hantke. Environmental factors influence the production of enterobactin, salmochelin, aerobactin, and yersiniabactin in Escherichia coli strain Nissle 1917. International journal of medical microbiology : IJMM. 2006 Dec; 296(8):513-20. doi: 10.1016/j.ijmm.2006.06.003. [PMID: 17008127]
  • Xueming Wei, Neeraja Vajrala, Loren Hauser, Luis A Sayavedra-Soto, Daniel J Arp. Iron nutrition and physiological responses to iron stress in Nitrosomonas europaea. Archives of microbiology. 2006 Aug; 186(2):107-18. doi: 10.1007/s00203-006-0126-4. [PMID: 16802173]
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  • W Rabsch, U Methner, W Voigt, H Tschäpe, R Reissbrodt, P H Williams. Role of receptor proteins for enterobactin and 2,3-dihydroxybenzoylserine in virulence of Salmonella enterica. Infection and immunity. 2003 Dec; 71(12):6953-61. doi: 10.1128/iai.71.12.6953-6961.2003. [PMID: 14638784]
  • Thomas A Russo, Catherine D McFadden, Ulrike B Carlino-MacDonald, Janet M Beanan, Travis J Barnard, James R Johnson. IroN functions as a siderophore receptor and is a urovirulence factor in an extraintestinal pathogenic isolate of Escherichia coli. Infection and immunity. 2002 Dec; 70(12):7156-60. doi: 10.1128/iai.70.12.7156-7160.2002. [PMID: 12438401]
  • Claire L Burton, Siri Ram Chhabra, Simon Swift, Tom J Baldwin, Helen Withers, Stephen J Hill, Paul Williams. The growth response of Escherichia coli to neurotransmitters and related catecholamine drugs requires a functional enterobactin biosynthesis and uptake system. Infection and immunity. 2002 Nov; 70(11):5913-23. doi: 10.1128/iai.70.11.5913-5923.2002. [PMID: 12379665]
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