N-3-oxo-dodecanoyl-L-homoserine lactone (BioDeep_00000015323)
Secondary id: BioDeep_00000409560
代谢物信息卡片
N-3-oxo-dodecanoyl-L-homoserine lactone
化学式: C16H27NO4 (297.1939982)
中文名称: 3-氧代-N-[(3S)-四氢-2-氧代-3-呋喃基]十二酰胺
谱图信息:
最多检出来源 Escherichia coli(natural_products) 66.67%
分子结构信息
SMILES: CCCCCCCCCC(=O)CC(=O)NC1CCOC1=O
InChI: InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:44534
- KEGG: C21201
- PubChem: 3246941
- DrugBank: DB08324
- ChEMBL: CHEMBL8483
- CAS: 168982-69-2
- PubChem: 316933499
- LipidMAPS: LMFA08030001
- PDB-CCD: OHN
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
- Wei Cheng, Zhenyu Wang, Yi Xiong, Zhifeng Wu, Xiang Tan, Yapeng Yang, Hang Zhang, Xi Zhu, Hong Wei, Shiyu Tao. N-(3-oxododecanoyl)-homoserine lactone disrupts intestinal barrier and induces systemic inflammation through perturbing gut microbiome in mice.
The Science of the total environment.
2021 Jul; 778(?):146347. doi:
10.1016/j.scitotenv.2021.146347. [PMID: 34030388] - Qinqin Pu, Kai Guo, Ping Lin, Zhihan Wang, Shugang Qin, Pan Gao, Colin Combs, Nadeem Khan, Zhenwei Xia, Min Wu. Bitter receptor TAS2R138 facilitates lipid droplet degradation in neutrophils during Pseudomonas aeruginosa infection.
Signal transduction and targeted therapy.
2021 06; 6(1):210. doi:
10.1038/s41392-021-00602-7. [PMID: 34083514] - Tomohiro Morohoshi, Yuto Ogasawara, Xiaonan Xie, Hiroshi Hamamoto, Nobutaka Someya. Genetic and Biochemical Diversity for N-acylhomoserine Lactone Biosynthesis in the Plant Pathogen Pectobacterium carotovorum subsp. carotovorum.
Microbes and environments.
2019 Dec; 34(4):429-435. doi:
10.1264/jsme2.me19105. [PMID: 31666459] - Dingka Song, Junchen Meng, Jie Cheng, Zheng Fan, Pengyu Chen, Hefei Ruan, Zhongyuan Tu, Ning Kang, Nan Li, Ying Xu, Xiaobo Wang, Fei Shu, Libing Mu, Tengfei Li, Wenran Ren, Xin Lin, Jun Zhu, Xiaohong Fang, Matthias W Amrein, Weihui Wu, Li-Tang Yan, Junhong Lü, Tie Xia, Yan Shi. Pseudomonas aeruginosa quorum-sensing metabolite induces host immune cell death through cell surface lipid domain dissolution.
Nature microbiology.
2019 01; 4(1):97-111. doi:
10.1038/s41564-018-0290-8. [PMID: 30510173] - Z Lou, H Wang, Y Tang, X Chen. The effect of burdock leaf fraction on adhesion, biofilm formation, quorum sensing and virulence factors of Pseudomonas aeruginosa.
Journal of applied microbiology.
2017 Mar; 122(3):615-624. doi:
10.1111/jam.13348. [PMID: 27860087] - Shiyu Tao, Yanwen Luo, Bin He, Jie Liu, Xi Qian, Yingdong Ni, Ruqian Zhao. Paraoxonase 2 modulates a proapoptotic function in LS174T cells in response to quorum sensing molecule N-(3-oxododecanoyl)-L-homoserine lactone.
Scientific reports.
2016 07; 6(?):28778. doi:
10.1038/srep28778. [PMID: 27364593] - Matthias Martin Gaida, Ulrike Dapunt, Gertrud Maria Hänsch. Sensing developing biofilms: the bitter receptor T2R38 on myeloid cells.
Pathogens and disease.
2016 Apr; 74(3):. doi:
10.1093/femspd/ftw004. [PMID: 26782143] - Paul K Grant, Neil Dalchau, James R Brown, Fernan Federici, Timothy J Rudge, Boyan Yordanov, Om Patange, Andrew Phillips, Jim Haseloff. Orthogonal intercellular signaling for programmed spatial behavior.
Molecular systems biology.
2016 Jan; 12(1):849. doi:
10.15252/msb.20156590. [PMID: 26814193] - Isar Dejban Golpasha, Seyed Fazlollah Mousavi, Parviz Owlia, Seyed Davar Siadat, Shiva Irani. Immunization with 3-oxododecanoyl-L-homoserine lactone-r-PcrV conjugate enhances survival of mice against lethal burn infections caused by Pseudomonas aeruginosa.
Bosnian journal of basic medical sciences.
2015 May; 15(2):15-24. doi:
10.17305/bjbms.2015.292. [PMID: 26042508] - Christian Schwarzer, Zhu Fu, Takeshi Morita, Aaron G Whitt, Aaron M Neely, Chi Li, Terry E Machen. Paraoxonase 2 serves a proapopotic function in mouse and human cells in response to the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-homoserine lactone.
The Journal of biological chemistry.
2015 Mar; 290(11):7247-58. doi:
10.1074/jbc.m114.620039. [PMID: 25627690] - Wen-Si Tan, Nina Yusrina Muhamad Yunos, Pui-Wan Tan, Nur Izzati Mohamad, Tan-Guan-Sheng Adrian, Wai-Fong Yin, Kok-Gan Chan. Pantoea sp. isolated from tropical fresh water exhibiting N-acyl homoserine lactone production.
TheScientificWorldJournal.
2014; 2014(?):828971. doi:
10.1155/2014/828971. [PMID: 25197715] - Gisela von Hoven, Nicole Kloft, Claudia Neukirch, Sabrina Ebinger, Wiesia Bobkiewicz, Silvia Weis, Klaus Boller, Kim D Janda, Matthias Husmann. Modulation of translation and induction of autophagy by bacterial exoproducts.
Medical microbiology and immunology.
2012 Nov; 201(4):409-18. doi:
10.1007/s00430-012-0271-0. [PMID: 22991039] - Olivier M Vandeputte, Martin Kiendrebeogo, Tsiry Rasamiravaka, Caroline Stévigny, Pierre Duez, Sanda Rajaonson, Billo Diallo, Adeline Mol, Marie Baucher, Mondher El Jaziri. The flavanone naringenin reduces the production of quorum sensing-controlled virulence factors in Pseudomonas aeruginosa PAO1.
Microbiology (Reading, England).
2011 Jul; 157(Pt 7):2120-2132. doi:
10.1099/mic.0.049338-0. [PMID: 21546585] - Maura Mattiuzzo, Iris Bertani, Sara Ferluga, Laura Cabrio, Joseph Bigirimana, Corrado Guarnaccia, Sandor Pongor, Henri Maraite, Vittorio Venturi. The plant pathogen Pseudomonas fuscovaginae contains two conserved quorum sensing systems involved in virulence and negatively regulated by RsaL and the novel regulator RsaM.
Environmental microbiology.
2011 Jan; 13(1):145-162. doi:
10.1111/j.1462-2920.2010.02316.x. [PMID: 20701623] - Alan R Smyth, Paramita M Cifelli, Catharine A Ortori, Karima Righetti, Sarah Lewis, Penny Erskine, Elaine D Holland, Michael Givskov, Paul Williams, Miguel Cámara, David A Barrett, Alan Knox. Garlic as an inhibitor of Pseudomonas aeruginosa quorum sensing in cystic fibrosis--a pilot randomized controlled trial.
Pediatric pulmonology.
2010 Apr; 45(4):356-62. doi:
10.1002/ppul.21193. [PMID: 20306535] - Pol Nadal Jimenez, Gudrun Koch, Evelina Papaioannou, Mariana Wahjudi, Joanna Krzeslak, Tom Coenye, Robbert H Cool, Wim J Quax. Role of PvdQ in Pseudomonas aeruginosa virulence under iron-limiting conditions.
Microbiology (Reading, England).
2010 Jan; 156(Pt 1):49-59. doi:
10.1099/mic.0.030973-0. [PMID: 19778968] - Shinichi Miyairi, Kazuhiro Tateda, Etsu T Fuse, Chihiro Ueda, Hiroaki Saito, Tohru Takabatake, Yoshikazu Ishii, Manabu Horikawa, Masaji Ishiguro, Theodore J Standiford, Keizo Yamaguchi. Immunization with 3-oxododecanoyl-L-homoserine lactone-protein conjugate protects mice from lethal Pseudomonas aeruginosa lung infection.
Journal of medical microbiology.
2006 Oct; 55(Pt 10):1381-1387. doi:
10.1099/jmm.0.46658-0. [PMID: 17005787] - Solveig Sjöblom, Günter Brader, Gudrun Koch, E Tapio Palva. Cooperation of two distinct ExpR regulators controls quorum sensing specificity and virulence in the plant pathogen Erwinia carotovora.
Molecular microbiology.
2006 Jun; 60(6):1474-89. doi:
10.1111/j.1365-2958.2006.05210.x. [PMID: 16796682] - Steven Atkinson, R Elizabeth Sockett, Miguel Cámara, Paul Williams. Quorum sensing and the lifestyle of Yersinia.
Current issues in molecular biology.
2006 Jan; 8(1):1-10. doi:
". [PMID: 16450882] - C L Pemberton, N A Whitehead, M Sebaihia, K S Bell, L J Hyman, S J Harris, A J Matlin, N D Robson, P R J Birch, J P Carr, I K Toth, G P C Salmond. Novel quorum-sensing-controlled genes in Erwinia carotovora subsp. carotovora: identification of a fungal elicitor homologue in a soft-rotting bacterium.
Molecular plant-microbe interactions : MPMI.
2005 Apr; 18(4):343-53. doi:
10.1094/mpmi-18-0343. [PMID: 15828686] - Christiane Buch, Jens Sigh, John Nielsen, Jens Laurits Larsen, Lone Gram. Production of acylated homoserine lactones by different serotypes of Vibrio anguillarum both in culture and during infection of rainbow trout.
Systematic and applied microbiology.
2003 Sep; 26(3):338-49. doi:
10.1078/072320203322497365. [PMID: 14529176] - Roger S Smith, Rodney Kelly, Barbara H Iglewski, Richard P Phipps. The Pseudomonas autoinducer N-(3-oxododecanoyl) homoserine lactone induces cyclooxygenase-2 and prostaglandin E2 production in human lung fibroblasts: implications for inflammation.
Journal of immunology (Baltimore, Md. : 1950).
2002 Sep; 169(5):2636-42. doi:
10.4049/jimmunol.169.5.2636. [PMID: 12193735] - S M Gardiner, S R Chhabra, C Harty, P Williams, D I Pritchard, B W Bycroft, T Bennett. Haemodynamic effects of the bacterial quorum sensing signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone, in conscious, normal and endotoxaemic rats.
British journal of pharmacology.
2001 Aug; 133(7):1047-54. doi:
10.1038/sj.bjp.0704174. [PMID: 11487515] - R S Smith, E R Fedyk, T A Springer, N Mukaida, B H Iglewski, R P Phipps. IL-8 production in human lung fibroblasts and epithelial cells activated by the Pseudomonas autoinducer N-3-oxododecanoyl homoserine lactone is transcriptionally regulated by NF-kappa B and activator protein-2.
Journal of immunology (Baltimore, Md. : 1950).
2001 Jul; 167(1):366-74. doi:
10.4049/jimmunol.167.1.366. [PMID: 11418672] - W Nasser, M L Bouillant, G Salmond, S Reverchon. Characterization of the Erwinia chrysanthemi expI-expR locus directing the synthesis of two N-acyl-homoserine lactone signal molecules.
Molecular microbiology.
1998 Sep; 29(6):1391-405. doi:
10.1046/j.1365-2958.1998.01022.x. [PMID: 9781877]