Mycolactone (BioDeep_00000009128)
natural product
代谢物信息卡片
Mycolactone
化学式: C44H70O9 (742.502)
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: C/C(=C\C=C\C(=C\[C@@H]([C@H](C[C@H](C)O)O)O)\C)/C=C(\C)/C=C/C(=O)O[C@H]1CCCC(=O)O[C@H](C/C=C(\C)/C[C@@H]1C)[C@@H](C)C/C(=C/[C@@H](C)[C@@H](C[C@@H](C)O)O)/C
InChI: InChI=1S/C44H70O9/c1-28(13-11-14-29(2)25-39(48)40(49)27-37(10)46)21-30(3)18-20-44(51)52-41-15-12-16-43(50)53-42(19-17-31(4)22-34(41)7)35(8)24-32(5)23-33(6)38(47)26-36(9)45/h11,13-14,17-18,20-21,23,25,33-42,45-49H,12,15-16,19,22,24,26-27H2,1-10H3/b14-11+,20-18+,28-13+,29-25+,30-21+,31-17+,32-23+/t33-,34+,35+,36-,37+,38-,39+,40+,41+,42-/m1/s1
数据库引用编号
12 个数据库交叉引用编号
- ChEBI: CHEBI:31871
- KEGG: C12151
- PubChem: 5282079
- PubChem: 74053234
- Metlin: METLIN69326
- CAS: 222050-77-3
- PMhub: MS000022874
- PubChem: 14298
- 3DMET: B04440
- NIKKAJI: J2.781.165E
- RefMet: Mycolactone
- LOTUS: LTS0218313
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)
5 个相关的物种来源信息
- 2 - Bacteria: LTS0218313
- 1762 - Mycobacteriaceae: LTS0218313
- 1763 - Mycobacterium: LTS0218313
- 1809 - Mycobacterium ulcerans: 10.1021/JA990017L
- 1809 - Mycobacterium ulcerans: LTS0218313
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
- Samuel Itskanov, Laurie Wang, Tina Junne, Rumi Sherriff, Li Xiao, Nicolas Blanchard, Wei Q Shi, Craig Forsyth, Dominic Hoepfner, Martin Spiess, Eunyong Park. A common mechanism of Sec61 translocon inhibition by small molecules.
Nature chemical biology.
2023 09; 19(9):1063-1071. doi:
10.1038/s41589-023-01337-y. [PMID: 37169959] - Daniela Ricci, Caroline Demangel. From Bacterial Toxin to Therapeutic Agent: The Unexpected Fate of Mycolactone.
Toxins.
2023 05; 15(6):. doi:
10.3390/toxins15060369. [PMID: 37368670] - Dongmin Kim, Tawni L Crippen, Laxmi Dhungel, Pablo J Delclos, Jeffery K Tomberlin, Heather R Jordan. Behavioral interplay between mosquito and mycolactone produced by Mycobacterium ulcerans and bacterial gene expression induced by mosquito proximity.
PloS one.
2023; 18(8):e0289768. doi:
10.1371/journal.pone.0289768. [PMID: 37535670] - Gabriel C A da Hora, John D M Nguyen, Jessica M J Swanson. Can membrane composition traffic toxins? Mycolactone and preferential membrane interactions.
Biophysical journal.
2022 11; 121(22):4260-4270. doi:
10.1016/j.bpj.2022.10.019. [PMID: 36258678] - Akira Kawashima, Mitsuo Kiriya, Junichiro En, Kazunari Tanigawa, Yasuhiro Nakamura, Yoko Fujiwara, Yuqian Luo, Keiji Maruyama, Shigekazu Watanabe, Masamichi Goto, Koichi Suzuki. Genome-wide screening identified SEC61A1 as an essential factor for mycolactone-dependent apoptosis in human premonocytic THP-1 cells.
PLoS neglected tropical diseases.
2022 08; 16(8):e0010672. doi:
10.1371/journal.pntd.0010672. [PMID: 35939511] - Louise Tzung-Harn Hsieh, Scott J Dos Santos, Belinda S Hall, Joy Ogbechi, Aloysius D Loglo, Francisco Javier Salguero, Marie-Thérèse Ruf, Gerd Pluschke, Rachel E Simmonds. Aberrant stromal tissue factor localisation and mycolactone-driven vascular dysfunction, exacerbated by IL-1β, are linked to fibrin formation in Buruli ulcer lesions.
PLoS pathogens.
2022 01; 18(1):e1010280. doi:
10.1371/journal.ppat.1010280. [PMID: 35100311] - Louisa Warryn. Competitive ELISA for the Detection and Quantification of Mycobacterium ulcerans Mycolactone.
Methods in molecular biology (Clifton, N.J.).
2022; 2387(?):151-161. doi:
10.1007/978-1-0716-1779-3_15. [PMID: 34643910] - Laxmi Dhungel, Lindsey Burcham, Joo Youn Park, Harshini Devi Sampathkumar, Albert Cudjoe, Keun Seok Seo, Heather Jordan. Responses to chemical cross-talk between the Mycobacterium ulcerans toxin, mycolactone, and Staphylococcus aureus.
Scientific reports.
2021 06; 11(1):11746. doi:
10.1038/s41598-021-89177-5. [PMID: 34083568] - Caroline Demangel. Immunity against Mycobacterium ulcerans: The subversive role of mycolactone.
Immunological reviews.
2021 05; 301(1):209-221. doi:
10.1111/imr.12956. [PMID: 33607704] - Emma Colucci-Guyon, Aline Rifflet, Sarah Saint-Auret, Anaëlle da Costa, Laurent Boucontet, Thomas Laval, Christophe Prehaud, Nicolas Blanchard, Jean-Pierre Levraud, Ivo G Boneca, Caroline Demangel, Laure Guenin-Macé. Spatiotemporal analysis of mycolactone distribution in vivo reveals partial diffusion in the central nervous system.
PLoS neglected tropical diseases.
2020 12; 14(12):e0008878. doi:
10.1371/journal.pntd.0008878. [PMID: 33264290] - M Foulon, M Robbe-Saule, J Manry, L Esnault, Y Boucaud, A Alcaïs, M Malloci, M Fanton d'Andon, T Beauvais, N Labarriere, P Jeannin, L Abel, J P Saint-André, A Croué, Y Delneste, I G Boneca, L Marsollier, E Marion. Mycolactone toxin induces an inflammatory response by targeting the IL-1β pathway: Mechanistic insight into Buruli ulcer pathophysiology.
PLoS pathogens.
2020 12; 16(12):e1009107. doi:
10.1371/journal.ppat.1009107. [PMID: 33338061] - Fikret Aydin, Rui Sun, Jessica M J Swanson. Mycolactone Toxin Membrane Permeation: Atomistic versus Coarse-Grained MARTINI Simulations.
Biophysical journal.
2019 07; 117(1):87-98. doi:
10.1016/j.bpj.2019.05.012. [PMID: 31174850] - Jessica Z Kubicek-Sutherland, Dung M Vu, Aaron S Anderson, Timothy C Sanchez, Paul J Converse, Ricardo Martí-Arbona, Eric L Nuermberger, Basil I Swanson, Harshini Mukundan. Understanding the Significance of Biochemistry in the Storage, Handling, Purification, and Sampling of Amphiphilic Mycolactone.
Toxins.
2019 04; 11(4):. doi:
10.3390/toxins11040202. [PMID: 30987300] - Caroline Demangel, Stephen High. Sec61 blockade by mycolactone: A central mechanism in Buruli ulcer disease.
Biology of the cell.
2018 Nov; 110(11):237-248. doi:
10.1111/boc.201800030. [PMID: 30055020] - Cesar A López, Clifford J Unkefer, Basil I Swanson, Jessica M J Swanson, S Gnanakaran. Membrane perturbing properties of toxin mycolactone from Mycobacterium ulcerans.
PLoS computational biology.
2018 02; 14(2):e1005972. doi:
10.1371/journal.pcbi.1005972. [PMID: 29401455] - Milène Nitenberg, Anaïs Bénarouche, Ofelia Maniti, Estelle Marion, Laurent Marsollier, Julie Géan, Erick J Dufourc, Jean-François Cavalier, Stéphane Canaan, Agnès P Girard-Egrot. The potent effect of mycolactone on lipid membranes.
PLoS pathogens.
2018 01; 14(1):e1006814. doi:
10.1371/journal.ppat.1006814. [PMID: 29320578] - Ok-Ryul Song, Han-Byul Kim, Samuel Jouny, Isabelle Ricard, Alexandre Vandeputte, Nathalie Deboosere, Estelle Marion, Christophe J Queval, Pierre Lesport, Emmanuel Bourinet, Daniel Henrion, Seog Bae Oh, Guillaume Lebon, Guillaume Sandoz, Edouard Yeramian, Laurent Marsollier, Priscille Brodin. A Bacterial Toxin with Analgesic Properties: Hyperpolarization of DRG Neurons by Mycolactone.
Toxins.
2017 07; 9(7):. doi:
10.3390/toxins9070227. [PMID: 28718822] - Wen-Ta Li, Hui-Wen Chang, Victor Fei Pang, Fun-In Wang, Chen-Hsuan Liu, Ting-Yu Chen, Jun-Cheng Guo, Takayuki Wada, Chian-Ren Jeng. Mycolactone-producing Mycobacterium marinum infection in captive Hong Kong warty newts and pathological evidence of impaired host immune function.
Diseases of aquatic organisms.
2017 Mar; 123(3):239-249. doi:
10.3354/dao03092. [PMID: 28322210] - Marcellin B Tano, Christelle Dassi, Lydia Mosi, Marina Koussémon, Bassirou Bonfoh. Molecular Characterization of Mycolactone Producing Mycobacteria from Aquatic Environments in Buruli Ulcer Non-Endemic Areas in Côte d'Ivoire.
International journal of environmental research and public health.
2017 02; 14(2):. doi:
10.3390/ijerph14020178. [PMID: 28208653] - Fred Stephen Sarfo, Richard Phillips, Mark Wansbrough-Jones, Rachel E Simmonds. Recent advances: role of mycolactone in the pathogenesis and monitoring of Mycobacterium ulcerans infection/Buruli ulcer disease.
Cellular microbiology.
2016 Jan; 18(1):17-29. doi:
10.1111/cmi.12547. [PMID: 26572803] - Fatoumata Niang, Fred S Sarfo, Michael Frimpong, Laure Guenin-Macé, Mark Wansbrough-Jones, Timothy Stinear, Richard O Phillips, Caroline Demangel. Metabolomic profiles delineate mycolactone signature in Buruli ulcer disease.
Scientific reports.
2015 Dec; 5(?):17693. doi:
10.1038/srep17693. [PMID: 26634444] - Laure Guenin-Macé, Reid Oldenburg, Fabrice Chrétien, Caroline Demangel. Pathogenesis of skin ulcers: lessons from the Mycobacterium ulcerans and Leishmania spp. pathogens.
Cellular and molecular life sciences : CMLS.
2014 Jul; 71(13):2443-50. doi:
10.1007/s00018-014-1561-z. [PMID: 24445815] - Belinda Hall, Rachel Simmonds. Pleiotropic molecular effects of the Mycobacterium ulcerans virulence factor mycolactone underlying the cell death and immunosuppression seen in Buruli ulcer.
Biochemical Society transactions.
2014 Feb; 42(1):177-83. doi:
10.1042/bst20130133. [PMID: 24450648] - Caroline Deshayes, Shiva Kumar Angala, Estelle Marion, Irène Brandli, Jérémie Babonneau, Laurent Preisser, Sara Eyangoh, Yves Delneste, Pierre Legras, Chantal De Chastellier, Timothy P Stinear, Mary Jackson, Laurent Marsollier. Regulation of mycolactone, the Mycobacterium ulcerans toxin, depends on nutrient source.
PLoS neglected tropical diseases.
2013 Nov; 7(11):e2502. doi:
10.1371/journal.pntd.0002502. [PMID: 24244764] - Laure Guenin-Macé, Romain Veyron-Churlet, Maria-Isabel Thoulouze, Guillaume Romet-Lemonne, Hui Hong, Peter F Leadlay, Anne Danckaert, Marie-Thérèse Ruf, Serge Mostowy, Chiara Zurzolo, Philippe Bousso, Fabrice Chrétien, Marie-France Carlier, Caroline Demangel. Mycolactone activation of Wiskott-Aldrich syndrome proteins underpins Buruli ulcer formation.
The Journal of clinical investigation.
2013 Apr; 123(4):1501-12. doi:
10.1172/jci66576. [PMID: 23549080] - Jessica L Porter, Nicholas J Tobias, Sacha J Pidot, Steffen Falgner, Kellie L Tuck, Andrea Vettiger, Hui Hong, Peter F Leadlay, Timothy P Stinear. The cell wall-associated mycolactone polyketide synthases are necessary but not sufficient for mycolactone biosynthesis.
PloS one.
2013; 8(7):e70520. doi:
10.1371/journal.pone.0070520. [PMID: 23894666] - Thorbjorg Einarsdottir, Kris Huygen. Buruli ulcer.
Human vaccines.
2011 Nov; 7(11):1198-203. doi:
10.4161/hv.7.11.17751. [PMID: 22048117] - Fred S Sarfo, Fabien Le Chevalier, N'Guetta Aka, Richard O Phillips, Yaw Amoako, Ivo G Boneca, Pascal Lenormand, Mireille Dosso, Mark Wansbrough-Jones, Romain Veyron-Churlet, Laure Guenin-Macé, Caroline Demangel. Mycolactone diffuses into the peripheral blood of Buruli ulcer patients--implications for diagnosis and disease monitoring.
PLoS neglected tropical diseases.
2011 Jul; 5(7):e1237. doi:
10.1371/journal.pntd.0001237. [PMID: 21811642] - Junichiro En, Norihisa Ishii, Masamichi Goto. [Role of mycolactone in the nerve damage of Buruli ulcer (Mycobacterium ulcerans infection)].
Nihon Hansenbyo Gakkai zasshi = Japanese journal of leprosy : official organ of the Japanese Leprosy Association.
2011 Feb; 80(1):5-10. doi:
10.5025/hansen.80.5. [PMID: 21404590] - Alvar Grönberg, Louise Zettergren, Kerstin Bergh, Mona Ståhle, Johan Heilborn, Kristian Angeby, Pamela L Small, Hannah Akuffo, Sven Britton. Antioxidants protect keratinocytes against M. ulcerans mycolactone cytotoxicity.
PloS one.
2010 Nov; 5(11):e13839. doi:
10.1371/journal.pone.0013839. [PMID: 21079804] - Sheerazed Boulkroun, Laure Guenin-Macé, Maria-Isabel Thoulouze, Marc Monot, Anaïs Merckx, Gordon Langsley, Georges Bismuth, Vincenzo Di Bartolo, Caroline Demangel. Mycolactone suppresses T cell responsiveness by altering both early signaling and posttranslational events.
Journal of immunology (Baltimore, Md. : 1950).
2010 Feb; 184(3):1436-44. doi:
10.4049/jimmunol.0902854. [PMID: 20042571] - Fred Stephen Sarfo, Richard O Phillips, Brian Rangers, Engy A Mahrous, Richard E Lee, Edward Tarelli, Kingsley B Asiedu, Pamela L Small, Mark H Wansbrough-Jones. Detection of Mycolactone A/B in Mycobacterium ulcerans-Infected Human Tissue.
PLoS neglected tropical diseases.
2010 Jan; 4(1):e577. doi:
10.1371/journal.pntd.0000577. [PMID: 20052267] - Petra Tafelmeyer, Christine Laurent, Pascal Lenormand, Jean-Claude Rousselle, Laurent Marsollier, Gilles Reysset, Runxuan Zhang, Albert Sickmann, Timothy P Stinear, Abdelkader Namane, Stewart T Cole. Comprehensive proteome analysis of Mycobacterium ulcerans and quantitative comparison of mycolactone biosynthesis.
Proteomics.
2008 Aug; 8(15):3124-38. doi:
10.1002/pmic.200701018. [PMID: 18615429] - Junichiro En, Masamichi Goto, Kazue Nakanaga, Michiyo Higashi, Norihisa Ishii, Hajime Saito, Suguru Yonezawa, Hirofumi Hamada, Pamela L C Small. Mycolactone is responsible for the painlessness of Mycobacterium ulcerans infection (buruli ulcer) in a murine study.
Infection and immunity.
2008 May; 76(5):2002-7. doi:
10.1128/iai.01588-07. [PMID: 18316387] - Hui Hong, Emmanuelle Coutanceau, Marion Leclerc, Laxmee Caleechurn, Peter F Leadlay, Caroline Demangel. Mycolactone diffuses from Mycobacterium ulcerans-infected tissues and targets mononuclear cells in peripheral blood and lymphoid organs.
PLoS neglected tropical diseases.
2008; 2(10):e325. doi:
10.1371/journal.pntd.0000325. [PMID: 18941518]
