Trypanothione (BioDeep_00000004844)

 

Secondary id: BioDeep_00001870079

human metabolite


代谢物信息卡片


(2S)-2-amino-4-{[(1R)-1-{[({3-[(4-{2-[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-3-sulfanylpropanamido]acetamido}butyl)amino]propyl}carbamoyl)methyl]carbamoyl}-2-sulfanylethyl]carbamoyl}butanoic acid

化学式: C27H49N9O10S2 (723.3044)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 9.12%

分子结构信息

SMILES: C(CCNC(=O)CNC(=O)C(CS)NC(=O)CCC(C(=O)O)N)CNCCCNC(=O)CNC(=O)C(CS)NC(=O)CCC(C(=O)O)N
InChI: InChI=1S/C27H49N9O10S2/c28-16(26(43)44)4-6-20(37)35-18(14-47)24(41)33-12-22(39)31-10-2-1-8-30-9-3-11-32-23(40)13-34-25(42)19(15-48)36-21(38)7-5-17(29)27(45)46/h16-19,30,47-48H,1-15,28-29H2,(H,31,39)(H,32,40)(H,33,41)(H,34,42)(H,35,37)(H,36,38)(H,43,44)(H,45,46)/t16-,17-,18-,19-/m0/s1

描述信息

Leishmaniasis is a neglected disease caused by Leishmania, an intracellular protozoan parasite which possesses a unique thiol metabolism based on trypanothione. (PMID: 22928053) Trypanosomatids, the causative agents of several tropical diseases, rely on trypanothione as principal low molecular mass thiol, and their glutaredoxins readily react with the unique bis(glutathionyl) spermidine conjugate. (PMID: 22978520) Among the potential molecular target, Trypanothione reductase (TR) is considered an ideal enzyme since it is involved in the unique thiol-based metabolism observed in the Trypanosomatidae family and is a validated target for the search of antitrypanosomatidae drugs. (PMID: 23410156)

同义名列表

19 个代谢物同义名

(2S)-2-amino-4-{[(1R)-1-{[({3-[(4-{2-[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-3-sulfanylpropanamido]acetamido}butyl)amino]propyl}carbamoyl)methyl]carbamoyl}-2-sulfanylethyl]carbamoyl}butanoic acid; (2S,7R,26R,31S)-2,31-Diamino-7,26-bis(mercaptomethyl)-5,8,11,22,25,28-hexaoxo-6,9,12,16,21,24,27-heptaazadotriacontane-1,32-dioic acid; (2S,7R,26R,31S)-2,31-Diamino-7,26-bis(mercaptomethyl)-5,8,11,22,25,28-hexaoxo-6,9,12,16,21,24,27-heptaazadotriacontane-1,32-dioate; N1,N8-Bis-(gamma-L-glutamyl-L-cysteinyl-glycyl)-spermidine; N1,N8-Bis(γ-L-glutamyl-L-cysteinyl-glycyl)spermidine; N1,N8-Bis(gamma-L-glutamyl-L-cysteinyl-glycyl)spermidine; N1,N8-Bis-(g-L-glutamyl-L-cysteinyl-glycyl)-spermidine; N1,N8-Bis-(γ-L-glutamyl-L-cysteinyl-glycyl)-spermidine; N1,N8-Bis(γ-L-glutamyl-L-cysteinyl-glycyl)spermidine; N1,N8-Bis(g-L-glutamyl-L-cysteinyl-glycyl)spermidine; BIS(GAMMA-glutamyl-cysteinyl-glycinyl)spermidine; BIS(g-glutamyl-cysteinyl-glycinyl)spermidine; BIS(γ-glutamyl-cysteinyl-glycinyl)spermidine; N1,N8-Bis-(glutathionyl)spermidine; N1,N8-Bis(glutathionyl)spermidine; Reduced trypanothione; Trypanothione; Trypanothion; TSH



数据库引用编号

14 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

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(4)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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

  • Sam Alsford, Sabine Eckert, Nicola Baker, Lucy Glover, Alejandro Sanchez-Flores, Ka Fai Leung, Daniel J Turner, Mark C Field, Matthew Berriman, David Horn. High-throughput decoding of antitrypanosomal drug efficacy and resistance. Nature. 2012 Jan; 482(7384):232-6. doi: 10.1038/nature10771. [PMID: 22278056]
  • Neha Sharma, Anil Kumar Shukla, Mousumi Das, Vikash Kumar Dubey. Evaluation of plumbagin and its derivative as potential modulators of redox thiol metabolism of Leishmania parasite. Parasitology research. 2012 Jan; 110(1):341-8. doi: 10.1007/s00436-011-2498-x. [PMID: 21717278]
  • Paul F Seke Etet, M Fawzi Mahomoodally. New insights in staging and chemotherapy of African trypanosomiasis and possible contribution of medicinal plants. TheScientificWorldJournal. 2012; 2012(?):343652. doi: 10.1100/2012/343652. [PMID: 22593674]
  • Endalkachew Nibret, Mahamoud Youns, R Luise Krauth-Siegel, Michael Wink. Biological activities of xanthatin from Xanthium strumarium leaves. Phytotherapy research : PTR. 2011 Dec; 25(12):1883-90. doi: 10.1002/ptr.3651. [PMID: 21953905]
  • Michael Diechtierow, R Luise Krauth-Siegel. A tryparedoxin-dependent peroxidase protects African trypanosomes from membrane damage. Free radical biology & medicine. 2011 Aug; 51(4):856-68. doi: 10.1016/j.freeradbiomed.2011.05.014. [PMID: 21640819]
  • Anil Kumar Shukla, Sanjukta Patra, Vikash Kumar Dubey. Deciphering molecular mechanism underlying antileishmanial activity of Nyctanthes arbortristis, an Indian medicinal plant. Journal of ethnopharmacology. 2011 Apr; 134(3):996-8. doi: 10.1016/j.jep.2011.01.044. [PMID: 21291983]
  • France Denoeud, Michaël Roussel, Benjamin Noel, Ivan Wawrzyniak, Corinne Da Silva, Marie Diogon, Eric Viscogliosi, Céline Brochier-Armanet, Arnaud Couloux, Julie Poulain, Béatrice Segurens, Véronique Anthouard, Catherine Texier, Nicolas Blot, Philippe Poirier, Geok Choo Ng, Kevin S W Tan, François Artiguenave, Olivier Jaillon, Jean-Marc Aury, Frédéric Delbac, Patrick Wincker, Christian P Vivarès, Hicham El Alaoui. Genome sequence of the stramenopile Blastocystis, a human anaerobic parasite. Genome biology. 2011; 12(3):R29. doi: 10.1186/gb-2011-12-3-r29. [PMID: 21439036]
  • Monica C O Campos, Kelly Salomão, Denise B Castro-Pinto, Leonor L Leon, Helene S Barbosa, Maria Aparecida M Maciel, Solange L de Castro. Croton cajucara crude extract and isolated terpenes: activity on Trypanosoma cruzi. Parasitology research. 2010 Oct; 107(5):1193-204. doi: 10.1007/s00436-010-1988-6. [PMID: 20680342]
  • Antonio Di Matteo, Adriana Sacco, Milena Anacleria, Mario Pezzotti, Massimo Delledonne, Alberto Ferrarini, Luigi Frusciante, Amalia Barone. The ascorbic acid content of tomato fruits is associated with the expression of genes involved in pectin degradation. BMC plant biology. 2010 Aug; 10(?):163. doi: 10.1186/1471-2229-10-163. [PMID: 20691085]
  • Vamsi K Kodali, Colin Thorpe. Quiescin sulfhydryl oxidase from Trypanosoma brucei: catalytic activity and mechanism of a QSOX family member with a single thioredoxin domain. Biochemistry. 2010 Mar; 49(9):2075-85. doi: 10.1021/bi902222s. [PMID: 20121244]
  • Amanda Fortes Francisco, Paula Melo de Abreu Vieira, Jerusa Marilda Arantes, Maisa Silva, Maria Lúcia Pedrosa, Silvana Maria Elói-Santos, Olindo Assis Martins-Filho, Andréa Teixeira-Carvalho, Márcio Sobreira Silva Araújo, Washington Luiz Tafuri, Cláudia Martins Carneiro. Increase of reactive oxygen species by desferrioxamine during experimental Chagas' disease. Redox report : communications in free radical research. 2010; 15(4):185-90. doi: 10.1179/174329210x12650506623528. [PMID: 20663295]
  • John W Whitaker, Glenn A McConkey, David R Westhead. The transferome of metabolic genes explored: analysis of the horizontal transfer of enzyme encoding genes in unicellular eukaryotes. Genome biology. 2009; 10(4):R36. doi: 10.1186/gb-2009-10-4-r36. [PMID: 19368726]
  • Magnus S Alphey, Janine König, Alan H Fairlamb. Structural and mechanistic insights into type II trypanosomatid tryparedoxin-dependent peroxidases. The Biochemical journal. 2008 Sep; 414(3):375-81. doi: 10.1042/bj20080889. [PMID: 18522537]
  • Betania Barros Cota, Luiz Henrique Rosa, Rachel Basques Caligiorne, Ana Lúcia Teles Rabello, Tânia Maria Almeida Alves, Carlos Augusto Rosa, Carlos Leomar Zani. Altenusin, a biphenyl isolated from the endophytic fungus Alternaria sp., inhibits trypanothione reductase from Trypanosoma cruzi. FEMS microbiology letters. 2008 Aug; 285(2):177-82. doi: 10.1111/j.1574-6968.2008.01221.x. [PMID: 18557945]
  • Diego G Arias, Pedro G Carranza, Hugo D Lujan, Alberto A Iglesias, Sergio A Guerrero. Immunolocalization and enzymatic functional characterization of the thioredoxin system in Entamoeba histolytica. Free radical biology & medicine. 2008 Jul; 45(1):32-9. doi: 10.1016/j.freeradbiomed.2008.03.008. [PMID: 18394433]
  • Margareth B C Gallo, Anna Sylvia F Marques, Paulo C Vieira, Maria Fátima das G F da Silva, João B Fernandes, Márcio Silva, Rafael V Guido, Glaucius Oliva, Otávio H Thiemann, Sérgio Albuquerque, Alan H Fairlamb. Enzymatic inhibitory activity and trypanocidal effects of extracts and compounds from Siphoneugena densiflora O. Berg and Vitex polygama Cham. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 May; 63(5-6):371-82. doi: 10.1515/znc-2008-5-611. [PMID: 18669023]
  • Elodie Gaulin, Mohammed-Amine Madoui, Arnaud Bottin, Christophe Jacquet, Catherine Mathé, Arnaud Couloux, Patrick Wincker, Bernard Dumas. Transcriptome of Aphanomyces euteiches: new oomycete putative pathogenicity factors and metabolic pathways. PloS one. 2008 Mar; 3(3):e1723. doi: 10.1371/journal.pone.0001723. [PMID: 18320043]
  • Fernanda Fraga Campos, Luiz Henrique Rosa, Betania Barros Cota, Rachel Basques Caligiorne, Ana Lúcia Teles Rabello, Tânia Maria Almeida Alves, Carlos Augusto Rosa, Carlos Leomar Zani. Leishmanicidal metabolites from Cochliobolus sp., an endophytic fungus isolated from Piptadenia adiantoides (Fabaceae). PLoS neglected tropical diseases. 2008; 2(12):e348. doi: 10.1371/journal.pntd.0000348. [PMID: 19079599]
  • Juan Diego Maya, Bruce K Cassels, Patricio Iturriaga-Vásquez, Jorge Ferreira, Mario Faúndez, Norbel Galanti, Arturo Ferreira, Antonio Morello. Mode of action of natural and synthetic drugs against Trypanosoma cruzi and their interaction with the mammalian host. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2007 Apr; 146(4):601-20. doi: 10.1016/j.cbpa.2006.03.004. [PMID: 16626984]
  • Matthew Berriman, Elodie Ghedin, Christiane Hertz-Fowler, Gaëlle Blandin, Hubert Renauld, Daniella C Bartholomeu, Nicola J Lennard, Elisabet Caler, Nancy E Hamlin, Brian Haas, Ulrike Böhme, Linda Hannick, Martin A Aslett, Joshua Shallom, Lucio Marcello, Lihua Hou, Bill Wickstead, U Cecilia M Alsmark, Claire Arrowsmith, Rebecca J Atkin, Andrew J Barron, Frederic Bringaud, Karen Brooks, Mark Carrington, Inna Cherevach, Tracey-Jane Chillingworth, Carol Churcher, Louise N Clark, Craig H Corton, Ann Cronin, Rob M Davies, Jonathon Doggett, Appolinaire Djikeng, Tamara Feldblyum, Mark C Field, Audrey Fraser, Ian Goodhead, Zahra Hance, David Harper, Barbara R Harris, Heidi Hauser, Jessica Hostetler, Al Ivens, Kay Jagels, David Johnson, Justin Johnson, Kristine Jones, Arnaud X Kerhornou, Hean Koo, Natasha Larke, Scott Landfear, Christopher Larkin, Vanessa Leech, Alexandra Line, Angela Lord, Annette Macleod, Paul J Mooney, Sharon Moule, David M A Martin, Gareth W Morgan, Karen Mungall, Halina Norbertczak, Doug Ormond, Grace Pai, Chris S Peacock, Jeremy Peterson, Michael A Quail, Ester Rabbinowitsch, Marie-Adele Rajandream, Chris Reitter, Steven L Salzberg, Mandy Sanders, Seth Schobel, Sarah Sharp, Mark Simmonds, Anjana J Simpson, Luke Tallon, C Michael R Turner, Andrew Tait, Adrian R Tivey, Susan Van Aken, Danielle Walker, David Wanless, Shiliang Wang, Brian White, Owen White, Sally Whitehead, John Woodward, Jennifer Wortman, Mark D Adams, T Martin Embley, Keith Gull, Elisabetta Ullu, J David Barry, Alan H Fairlamb, Fred Opperdoes, Barclay G Barrell, John E Donelson, Neil Hall, Claire M Fraser, Sara E Melville, Najib M El-Sayed. The genome of the African trypanosome Trypanosoma brucei. Science (New York, N.Y.). 2005 Jul; 309(5733):416-22. doi: 10.1126/science.1112642. [PMID: 16020726]
  • Tim J Vickers, Susan Wyllie, Alan H Fairlamb. Leishmania major elongation factor 1B complex has trypanothione S-transferase and peroxidase activity. The Journal of biological chemistry. 2004 Nov; 279(47):49003-9. doi: 10.1074/jbc.m407958200. [PMID: 15322082]
  • Helena Castro, Heike Budde, Leopold Flohé, Birgit Hofmann, Heinrich Lünsdorf, Joseph Wissing, Ana M Tomás. Specificity and kinetics of a mitochondrial peroxiredoxin of Leishmania infantum. Free radical biology & medicine. 2002 Dec; 33(11):1563-74. doi: 10.1016/s0891-5849(02)01088-2. [PMID: 12446214]
  • M R Ariyanayagam, A H Fairlamb. Ovothiol and trypanothione as antioxidants in trypanosomatids. Molecular and biochemical parasitology. 2001 Jul; 115(2):189-98. doi: 10.1016/s0166-6851(01)00285-7. [PMID: 11420105]
  • S Girault, T E Davioud-Charvet, L Maes, J F Dubremetz, M A Debreu, V Landry, C Sergheraert. Potent and specific inhibitors of trypanothione reductase from Trypanosoma cruzi: bis(2-aminodiphenylsulfides) for fluorescent labeling studies. Bioorganic & medicinal chemistry. 2001 Apr; 9(4):837-46. doi: 10.1016/s0968-0896(00)00312-6. [PMID: 11354666]