Syringolin A (BioDeep_00000016888)

   


代谢物信息卡片


2-(3-(1-(((4E,10E)-2,9-Dioxo-12-isopropyl-1,8-diazacyclododecane-4,10-diene-3-yl)carbamoyl)-2-methylpropyl)ureido)-3-methylbutyric acid

化学式: C24H39N5O6 (493.29)
中文名称:
谱图信息: 最多检出来源 not specific(not specific) 0%

分子结构信息

SMILES: CC(C)C1C=CC(=O)NCCC=CC(C(=O)N1)NC(=O)C(C(C)C)NC(=O)NC(C(C)C)C(=O)O
InChI: InChI=1S/C24H39N5O6/c1-13(2)16-10-11-18(30)25-12-8-7-9-17(21(31)26-16)27-22(32)19(14(3)4)28-24(35)29-20(15(5)6)23(33)34/h7,9-11,13-17,19-20H,8,12H2,1-6H3,(H,25,30)(H,26,31)(H,27,32)(H,33,34)(H2,28,29,35)/b9-7+,11-10+/t16-,17+,19+,20+/m1/s1

描述信息

A syrbactin that has a (3E,9E)-2,7-dioxo-1,6-diazacyclododeca-3,9-diene skeleton that is substituted by an isopropyl group at position 5 and by a [(2S)-2-({[(1S)-1-carboxy-2-methylpropyl]carbamoyl}amino)-3-methylbutanoyl]nitrilo group at the 8-pro-S position. It is produced by the pathogenic bacterium Pseudomonas syringae pv. syringae.

同义名列表

2 个代谢物同义名

Syringolin A; 2-(3-(1-(((4E,10E)-2,9-Dioxo-12-isopropyl-1,8-diazacyclododecane-4,10-diene-3-yl)carbamoyl)-2-methylpropyl)ureido)-3-methylbutyric acid



数据库引用编号

12 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)

3 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。

亚细胞结构定位 关联基因列表


文献列表

  • Diane Marie Valerie Bonnet, Louis Tirot, Stefan Grob, Pauline Emilie Jullien. Methylome Response to Proteasome Inhibition by Pseudomonas syringae Virulence Factor Syringolin A. Molecular plant-microbe interactions : MPMI. 2023 Nov; 36(11):693-704. doi: 10.1094/mpmi-06-23-0080-r. [PMID: 37414416]
  • Alexey Dudnik, Robert Dudler. Virulence determinants of Pseudomonas syringae strains isolated from grasses in the context of a small type III effector repertoire. BMC microbiology. 2014 Dec; 14(?):304. doi: 10.1186/s12866-014-0304-5. [PMID: 25472590]
  • Julia Svozil, Matthias Hirsch-Hoffmann, Robert Dudler, Wilhelm Gruissem, Katja Baerenfaller. Protein abundance changes and ubiquitylation targets identified after inhibition of the proteasome with syringolin A. Molecular & cellular proteomics : MCP. 2014 Jun; 13(6):1523-36. doi: 10.1074/mcp.m113.036269. [PMID: 24732913]
  • Alexey Dudnik, Laurent Bigler, Robert Dudler. Production of proteasome inhibitor syringolin A by the endophyte Rhizobium sp. strain AP16. Applied and environmental microbiology. 2014 Jun; 80(12):3741-8. doi: 10.1128/aem.00395-14. [PMID: 24727275]
  • Silvia Schelbert Hofstetter, Alexey Dudnik, Heidi Widmer, Robert Dudler. Arabidopsis YELLOW STRIPE-LIKE7 (YSL7) and YSL8 transporters mediate uptake of Pseudomonas virulence factor syringolin A into plant cells. Molecular plant-microbe interactions : MPMI. 2013 Nov; 26(11):1302-11. doi: 10.1094/mpmi-06-13-0163-r. [PMID: 23945001]
  • Johana C Misas-Villamil, Izabella Kolodziejek, Emerson Crabill, Farnusch Kaschani, Sherry Niessen, Takayuki Shindo, Markus Kaiser, James R Alfano, Renier A L van der Hoorn. Pseudomonas syringae pv. syringae uses proteasome inhibitor syringolin A to colonize from wound infection sites. PLoS pathogens. 2013 Mar; 9(3):e1003281. doi: 10.1371/journal.ppat.1003281. [PMID: 23555272]
  • Xilan Yu, Steven P Lund, Russell A Scott, Jessica W Greenwald, Angela H Records, Dan Nettleton, Steven E Lindow, Dennis C Gross, Gwyn A Beattie. Transcriptional responses of Pseudomonas syringae to growth in epiphytic versus apoplastic leaf sites. Proceedings of the National Academy of Sciences of the United States of America. 2013 Jan; 110(5):E425-34. doi: 10.1073/pnas.1221892110. [PMID: 23319638]
  • Robert Dudler. Manipulation of host proteasomes as a virulence mechanism of plant pathogens. Annual review of phytopathology. 2013; 51(?):521-42. doi: 10.1146/annurev-phyto-082712-102312. [PMID: 23725468]
  • Christina Ramel, Nando Baechler, Michel Hildbrand, Martin Meyer, David Schädeli, Robert Dudler. Regulation of biosynthesis of syringolin A, a Pseudomonas syringae virulence factor targeting the host proteasome. Molecular plant-microbe interactions : MPMI. 2012 Sep; 25(9):1198-208. doi: 10.1094/mpmi-03-12-0070-r. [PMID: 22852810]
  • John Opoku-Ansah, Tannya R Ibarra-Rivera, Michael C Pirrung, André S Bachmann. Syringolin B-inspired proteasome inhibitor analogue TIR-203 exhibits enhanced biological activity in multiple myeloma and neuroblastoma. Pharmaceutical biology. 2012 Jan; 50(1):25-9. doi: 10.3109/13880209.2011.626784. [PMID: 22196580]
  • Izabella Kolodziejek, Johana C Misas-Villamil, Farnusch Kaschani, Jérôme Clerc, Christian Gu, Daniel Krahn, Sherry Niessen, Martijn Verdoes, Lianne I Willems, Hermen S Overkleeft, Markus Kaiser, Renier A L van der Hoorn. Proteasome activity imaging and profiling characterizes bacterial effector syringolin A. Plant physiology. 2011 Jan; 155(1):477-89. doi: 10.1104/pp.110.163733. [PMID: 21045122]
  • Barbara Schellenberg, Christina Ramel, Robert Dudler. Pseudomonas syringae virulence factor syringolin A counteracts stomatal immunity by proteasome inhibition. Molecular plant-microbe interactions : MPMI. 2010 Oct; 23(10):1287-93. doi: 10.1094/mpmi-04-10-0094. [PMID: 20831408]
  • Christina Ramel, Micha Tobler, Martin Meyer, Laurent Bigler, Marc-Olivier Ebert, Barbara Schellenberg, Robert Dudler. Biosynthesis of the proteasome inhibitor syringolin A: the ureido group joining two amino acids originates from bicarbonate. BMC biochemistry. 2009 Oct; 10(?):26. doi: 10.1186/1471-2091-10-26. [PMID: 19863801]
  • Michael Groll, Barbara Schellenberg, André S Bachmann, Crystal R Archer, Robert Huber, Tracy K Powell, Steven Lindow, Markus Kaiser, Robert Dudler. A plant pathogen virulence factor inhibits the eukaryotic proteasome by a novel mechanism. Nature. 2008 Apr; 452(7188):755-8. doi: 10.1038/nature06782. [PMID: 18401409]
  • C S Coleman, J P Rocetes, D J Park, C J Wallick, B J Warn-Cramer, K Michel, R Dudler, A S Bachmann. Syringolin A, a new plant elicitor from the phytopathogenic bacterium Pseudomonas syringae pv. syringae, inhibits the proliferation of neuroblastoma and ovarian cancer cells and induces apoptosis. Cell proliferation. 2006 Dec; 39(6):599-609. doi: 10.1111/j.1365-2184.2006.00402.x. [PMID: 17109642]
  • Kathrin Michel, Olaf Abderhalden, Rémy Bruggmann, Robert Dudler. Transcriptional changes in powdery mildew infected wheat and Arabidopsis leaves undergoing syringolin-triggered hypersensitive cell death at infection sites. Plant molecular biology. 2006 Nov; 62(4-5):561-78. doi: 10.1007/s11103-006-9045-7. [PMID: 16941219]
  • Hans Amrein, Stefan Makart, José Granado, Roshani Shakya, Jana Schneider-Pokorny, Robert Dudler. Functional analysis of genes involved in the synthesis of syringolin A by Pseudomonas syringae pv. syringae B301 D-R. Molecular plant-microbe interactions : MPMI. 2004 Jan; 17(1):90-7. doi: 10.1094/mpmi.2004.17.1.90. [PMID: 14714872]
  • U Wäspi, P Schweizer, R Dudler. Syringolin reprograms wheat to undergo hypersensitive cell death in a compatible interaction with powdery mildew. The Plant cell. 2001 Jan; 13(1):153-61. doi: ". [PMID: 11158536]