Dethiobiotin (BioDeep_00000001323)

Main id: BioDeep_00000400006

Secondary id: BioDeep_00001868851

human metabolite PANOMIX_OTCML-2023 Endogenous BioNovoGene_Lab2019


代谢物信息卡片


6-[(4R,5S)-5-methyl-2-oxoimidazolidin-4-yl]hexanoic acid

化学式: C10H18N2O3 (214.1317358)
中文名称: 5-甲基-2-氧-4-咪唑啉己酸, D-脱硫生物素, d-Desthiobiotin
谱图信息: 最多检出来源 Viridiplantae(plant) 4.22%

分子结构信息

SMILES: CC1C(NC(=O)N1)CCCCCC(=O)O
InChI: InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)

描述信息

Dethiobiotin is a synthetic metabolite that mimic the effects of biotin on gene expression and thus have biotin-like activities. In mammals, biotin serves as a coenzyme for carboxylases such as propionyl-CoA carboxylase. (PMID 12730407) [HMDB]. Dethiobiotin is found in many foods, some of which are agave, garden onion, lime, and black mulberry.
Dethiobiotin is a synthetic metabolite that mimic the effects of biotin on gene expression and thus have biotin-like activities. In mammals, biotin serves as a coenzyme for carboxylases such as propionyl-CoA carboxylase. (PMID 12730407).
D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents
D050258 - Mitosis Modulators > D008934 - Mitogens
KEIO_ID D075; [MS3] KO009104
KEIO_ID D075; [MS2] KO009103
KEIO_ID D075
D-Desthiobiotin is a biotin derivative used in affinity chromatography and protein chromatography. D-Desthiobiotin also can be used for protein and cell labeling, detection and isolation[1].

同义名列表

21 个代谢物同义名

6-[(4R,5S)-5-methyl-2-oxoimidazolidin-4-yl]hexanoic acid; (4R-cis)-5-Methyl-2-oxo-4-imidazolidinehexanoic acid; (4R,5S)-5-Methyl-2-oxo-4-imidazolidinehexanoic acid; (4R-cis)-5-Methyl-2-oxo-4-imidazolidinehexanoate; epsilon-(4-Methyl-5-imidazolidone-2)caproic acid; (4R,5S)-5-Methyl-2-oxo-4-imidazolidinehexanoate; 4-Methyl-5-(omega-carboxyamyl)imidazolidone-2; 5-Methyl-2-oxo-4-imidazolidinehexanoic acid; ε-(4-Methyl-5-imidazolidone-2)caproic acid; 5-Methyl-2-oxo-4-imidazolidinecaproic acid; 4-Methyl-5-(ω-carboxyamyl)imidazolidone-2; Desthiobiotin, (cis)-(+-)-isomer; Desthiobiotin, (4R-cis)-isomer; (4R,5S)-dethiobiotin; (+)-Dethiobiotin; dl-Dithiobiotin; D-Dethiobiotin; Desthiobiotin; dethiobiotin; Dethiobiotin; D-Desthiobiotin



数据库引用编号

34 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

242 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(240)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2)

  • Biotin Metabolism: Dethiobiotin + Hydrogen Ion + S-Adenosylmethionine + a sulfurated [sulfur carrier] ⟶ 5'-Deoxyadenosine + Biotin + L-Methionine
  • Biotin Metabolism: Adenosine triphosphate + Biotin ⟶ Biotinyl-5'-AMP + diphosphate

PharmGKB(0)

5 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

  • Di Qu, Peng Ge, Laure Botella, Sae Woong Park, Ha-Na Lee, Natalie Thornton, James M Bean, Inna V Krieger, James C Sacchettini, Sabine Ehrt, Courtney C Aldrich, Dirk Schnappinger. Mycobacterial biotin synthases require an auxiliary protein to convert dethiobiotin into biotin. Nature communications. 2024 May; 15(1):4161. doi: 10.1038/s41467-024-48448-1. [PMID: 38755122]
  • Chaoxiang Chen, Mengdi Sun, Jialin Wang, Liyun Su, Junjie Lin, Xiaomei Yan. Active cargo loading into extracellular vesicles: Highlights the heterogeneous encapsulation behaviour. Journal of extracellular vesicles. 2021 11; 10(13):e12163. doi: 10.1002/jev2.12163. [PMID: 34719860]
  • Benjamin Lake, Nickolas Serniuck, Eden Kapcan, Alex Wang, Anthony F Rullo. Covalent Immune Recruiters: Tools to Gain Chemical Control Over Immune Recognition. ACS chemical biology. 2020 04; 15(4):1089-1095. doi: 10.1021/acschembio.0c00112. [PMID: 32100991]
  • Yudi Ding, Nicholas H Williams, Christopher A Hunter. A Synthetic Vesicle-to-Vesicle Communication System. Journal of the American Chemical Society. 2019 11; 141(44):17847-17853. doi: 10.1021/jacs.9b09102. [PMID: 31642667]
  • Kathrin E Witzke, Kristin Rosowski, Christian Müller, Maike Ahrens, Martin Eisenacher, Dominik A Megger, Jürgen Knobloch, Andrea Koch, Thilo Bracht, Barbara Sitek. Quantitative Secretome Analysis of Activated Jurkat Cells Using Click Chemistry-Based Enrichment of Secreted Glycoproteins. Journal of proteome research. 2017 01; 16(1):137-146. doi: 10.1021/acs.jproteome.6b00575. [PMID: 27696881]
  • Anne-Marie Haughey, Benoit Guilhabert, Alexander L Kanibolotsky, Peter J Skabara, Martin D Dawson, Glenn A Burley, Nicolas Laurand. An oligofluorene truxene based distributed feedback laser for biosensing applications. Biosensors & bioelectronics. 2014 Apr; 54(?):679-86. doi: 10.1016/j.bios.2013.11.054. [PMID: 24355421]
  • Joji Grace Villamor, Farnusch Kaschani, Tom Colby, Julian Oeljeklaus, David Zhao, Markus Kaiser, Matthew P Patricelli, Renier A L van der Hoorn. Profiling protein kinases and other ATP binding proteins in Arabidopsis using Acyl-ATP probes. Molecular & cellular proteomics : MCP. 2013 Sep; 12(9):2481-96. doi: 10.1074/mcp.m112.026278. [PMID: 23722185]
  • David Cobessi, Renaud Dumas, Virginie Pautre, Céline Meinguet, Jean-Luc Ferrer, Claude Alban. Biochemical and structural characterization of the Arabidopsis bifunctional enzyme dethiobiotin synthetase-diaminopelargonic acid aminotransferase: evidence for substrate channeling in biotin synthesis. The Plant cell. 2012 Apr; 24(4):1608-25. doi: 10.1105/tpc.112.097675. [PMID: 22547782]
  • 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]
  • Teresa A Figueiredo, Rita G Sobral, Ana Madalena Ludovice, João Manuel Feio de Almeida, Nhat K Bui, Waldemar Vollmer, Hermínia de Lencastre, Alexander Tomasz. Identification of genetic determinants and enzymes involved with the amidation of glutamic acid residues in the peptidoglycan of Staphylococcus aureus. PLoS pathogens. 2012 Jan; 8(1):e1002508. doi: 10.1371/journal.ppat.1002508. [PMID: 22303291]
  • Aurélien Deniaud, Pankaj Panwar, Annie Frelet-Barrand, Florent Bernaudat, Céline Juillan-Binard, Christine Ebel, Norbert Rolland, Eva Pebay-Peyroula. Oligomeric status and nucleotide binding properties of the plastid ATP/ADP transporter 1: toward a molecular understanding of the transport mechanism. PloS one. 2012; 7(3):e32325. doi: 10.1371/journal.pone.0032325. [PMID: 22438876]
  • Thomas Oellerich, Vanessa Bremes, Konstantin Neumann, Hanibal Bohnenberger, Kai Dittmann, He-Hsuan Hsiao, Michael Engelke, Tim Schnyder, Facundo D Batista, Henning Urlaub, Jürgen Wienands. The B-cell antigen receptor signals through a preformed transducer module of SLP65 and CIN85. The EMBO journal. 2011 Aug; 30(17):3620-34. doi: 10.1038/emboj.2011.251. [PMID: 21822214]
  • Pasqualina Magliano, Michel Flipphi, Dominique Sanglard, Yves Poirier. Characterization of the Aspergillus nidulans biotin biosynthetic gene cluster and use of the bioDA gene as a new transformation marker. Fungal genetics and biology : FG & B. 2011 Feb; 48(2):208-15. doi: 10.1016/j.fgb.2010.08.004. [PMID: 20713166]
  • Andrew W Tai, Shadi Salloum. The role of the phosphatidylinositol 4-kinase PI4KA in hepatitis C virus-induced host membrane rearrangement. PloS one. 2011; 6(10):e26300. doi: 10.1371/journal.pone.0026300. [PMID: 22022594]
  • Annie Frelet-Barrand, Sylvain Boutigny, Lucas Moyet, Aurélien Deniaud, Daphné Seigneurin-Berny, Daniel Salvi, Florent Bernaudat, Pierre Richaud, Eva Pebay-Peyroula, Jacques Joyard, Norbert Rolland. Lactococcus lactis, an alternative system for functional expression of peripheral and intrinsic Arabidopsis membrane proteins. PloS one. 2010 Jan; 5(1):e8746. doi: 10.1371/journal.pone.0008746. [PMID: 20098692]
  • Nga T Lao, Alan P Maloney, John F Atkins, Tony A Kavanagh. Versatile dual reporter gene systems for investigating stop codon readthrough in plants. PloS one. 2009 Oct; 4(10):e7354. doi: 10.1371/journal.pone.0007354. [PMID: 19816579]
  • Feng Xiao, Jinchuan Sun, Oana Coban, Peter Schoen, Joseph Che-Yen Wang, R Holland Cheng, Peixuan Guo. Fabrication of massive sheets of single layer patterned arrays using lipid directed reengineered phi29 motor dodecamer. ACS nano. 2009 Jan; 3(1):100-7. doi: 10.1021/nn800409a. [PMID: 19206255]
  • David P Dixon, Timothy Hawkins, Patrick J Hussey, Robert Edwards. Enzyme activities and subcellular localization of members of the Arabidopsis glutathione transferase superfamily. Journal of experimental botany. 2009; 60(4):1207-18. doi: 10.1093/jxb/ern365. [PMID: 19174456]
  • Marie-Laure Rosso, Sylvie Chauvaux, Rodrigue Dessein, Caroline Laurans, Lionel Frangeul, Céline Lacroix, Angèle Schiavo, Marie-Agnès Dillies, Jeannine Foulon, Jean-Yves Coppée, Claudine Médigue, Elisabeth Carniel, Michel Simonet, Michaël Marceau. Growth of Yersinia pseudotuberculosis in human plasma: impacts on virulence and metabolic gene expression. BMC microbiology. 2008 Dec; 8(?):211. doi: 10.1186/1471-2180-8-211. [PMID: 19055764]
  • Guy Patchornik. Purification of His-tagged proteins with [desthiobiotin-BSA-EDTA] conjugates exhibiting resistance to EDTA. Bioconjugate chemistry. 2008 Mar; 19(3):673-9. doi: 10.1021/bc700368y. [PMID: 18311907]
  • Rosanna Muralla, Elve Chen, Colleen Sweeney, Jennifer A Gray, Allan Dickerman, Basil J Nikolau, David Meinke. A bifunctional locus (BIO3-BIO1) required for biotin biosynthesis in Arabidopsis. Plant physiology. 2008 Jan; 146(1):60-73. doi: 10.1104/pp.107.107409. [PMID: 17993549]
  • Ronald van Doorn, Marianna Szemes, Peter Bonants, George A Kowalchuk, Joana F Salles, Elen Ortenberg, Cor D Schoen. Quantitative multiplex detection of plant pathogens using a novel ligation probe-based system coupled with universal, high-throughput real-time PCR on OpenArrays. BMC genomics. 2007 Aug; 8(?):276. doi: 10.1186/1471-2164-8-276. [PMID: 17697351]
  • Guy Patchornik. Double-modified albumins as a tool for antibody purification. Journal of biochemical and biophysical methods. 2007 Jun; 70(4):671-3. doi: 10.1016/j.jbbm.2007.01.012. [PMID: 17324468]
  • Nadège Arnal, Claude Alban, Martine Quadrado, Olivier Grandjean, Hakim Mireau. The Arabidopsis Bio2 protein requires mitochondrial targeting for activity. Plant molecular biology. 2006 Oct; 62(3):471-9. doi: 10.1007/s11103-006-9034-x. [PMID: 16897469]
  • Krishnaswamy Balamurugan, Nosratola D Vaziri, Hamid M Said. Biotin uptake by human proximal tubular epithelial cells: cellular and molecular aspects. American journal of physiology. Renal physiology. 2005 Apr; 288(4):F823-31. doi: 10.1152/ajprenal.00375.2004. [PMID: 15561972]
  • Franziska Grafe, Wolfgang Wohlrab, Reinhard H Neubert, Matthias Brandsch. Transport of biotin in human keratinocytes. The Journal of investigative dermatology. 2003 Mar; 120(3):428-33. doi: 10.1046/j.1523-1747.2003.12058.x. [PMID: 12603856]
  • Jürgen Stolz. Isolation and characterization of the plasma membrane biotin transporter from Schizosaccharomyces pombe. Yeast (Chichester, England). 2003 Feb; 20(3):221-31. doi: 10.1002/yea.959. [PMID: 12557275]
  • A Picciocchi, R Douce, C Alban. Biochemical characterization of the Arabidopsis biotin synthase reaction. The importance of mitochondria in biotin synthesis. Plant physiology. 2001 Nov; 127(3):1224-33. doi: 10.1104/pp.010346. [PMID: 11706201]
  • S Chiruvolu, S Walker, J Israelachvili, F J Schmitt, D Leckband, J A Zasadzinski. Higher order self-assembly of vesicles by site-specific binding. Science (New York, N.Y.). 1994 Jun; 264(5166):1753-6. doi: 10.1126/science.8209255. [PMID: 8209255]
  • S M Krassner, B Granger, P Phermsangngnam, T Le, V Linden. Further studies on substrates inducing metacyclogenesis in Trypanosoma cruzi. The Journal of protozoology. 1990 Mar; 37(2):128-32. doi: 10.1111/j.1550-7408.1990.tb05882.x. [PMID: 2181116]
  • T Schneider, R Dinkins, K Robinson, J Shellhammer, D W Meinke. An embryo-lethal mutant of Arabidopsis thaliana is a biotin auxotroph. Developmental biology. 1989 Jan; 131(1):161-7. doi: 10.1016/s0012-1606(89)80047-8. [PMID: 2909401]