lipoamide (BioDeep_00000399999)

Main id: BioDeep_00000003137

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


5-(1,2-dithiolan-3-yl)pentanamide

化学式: C8H15NOS2 (205.05950199999998)
中文名称: 硫辛酰胺, DL-硫辛酰胺
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.74%

分子结构信息

SMILES: C(CCC(=O)N)CC1CCSS1
InChI: InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)

描述信息

A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of lipoic acid with ammonia.

同义名列表

6 个代谢物同义名

lipoamide; 5-(1,2-dithiolan-3-yl)pentanamide; alpha-lipoic acid amide; Thioctic acid amide; Thioctamide; vitamin N



数据库引用编号

36 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(7)

BioCyc(1)

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)

4 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

  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Jie Yang, Qingzheng Zhu, Feng Xu, Ming Yang, Hechao Du, Xiaoying Bian, Zhaoxin Lu, Yingjian Lu, Fengxia Lu. Genome Mining, Heterologous Expression, Antibacterial and Antioxidant Activities of Lipoamides and Amicoumacins from Compost-Associated Bacillus subtilis fmb60. Molecules (Basel, Switzerland). 2021 Mar; 26(7):. doi: 10.3390/molecules26071892. [PMID: 33810551]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Can Peng, Xiaohan Jiang, Ying Xiao, Zhiping Yuan, Yanwen Mao, Yuanyuan Wang Wang, Yingying Zhang, Fan Zhang, Lei Tang, Bing Guo. [Alpha-lipoamide inhibits renal inflammation and collagen 4 production in diabetic rats and its mechanism]. Xi bao yu fen zi mian yi xue za zhi = Chinese journal of cellular and molecular immunology. 2018 Jul; 34(7):617-622. doi: . [PMID: 30381126]
  • Gaia Novarino, Paul El-Fishawy, Hulya Kayserili, Nagwa A Meguid, Eric M Scott, Jana Schroth, Jennifer L Silhavy, Majdi Kara, Rehab O Khalil, Tawfeg Ben-Omran, A Gulhan Ercan-Sencicek, Adel F Hashish, Stephan J Sanders, Abha R Gupta, Hebatalla S Hashem, Dietrich Matern, Stacey Gabriel, Larry Sweetman, Yasmeen Rahimi, Robert A Harris, Matthew W State, Joseph G Gleeson. Mutations in BCKD-kinase lead to a potentially treatable form of autism with epilepsy. Science (New York, N.Y.). 2012 Oct; 338(6105):394-7. doi: 10.1126/science.1224631. [PMID: 22956686]
  • Alan K Lam, Pamuditha N Silva, Svetlana M Altamentova, Jonathan V Rocheleau. Quantitative imaging of electron transfer flavoprotein autofluorescence reveals the dynamics of lipid partitioning in living pancreatic islets. Integrative biology : quantitative biosciences from nano to macro. 2012 Aug; 4(8):838-46. doi: 10.1039/c2ib20075a. [PMID: 22733276]
  • Meiyi Zhou, Gang Lu, Chen Gao, Yibin Wang, Haipeng Sun. Tissue-specific and nutrient regulation of the branched-chain α-keto acid dehydrogenase phosphatase, protein phosphatase 2Cm (PP2Cm). The Journal of biological chemistry. 2012 Jul; 287(28):23397-406. doi: 10.1074/jbc.m112.351031. [PMID: 22589535]
  • Philip J Saylor, Edward D Karoly, Matthew R Smith. Prospective study of changes in the metabolomic profiles of men during their first three months of androgen deprivation therapy for prostate cancer. Clinical cancer research : an official journal of the American Association for Cancer Research. 2012 Jul; 18(13):3677-85. doi: 10.1158/1078-0432.ccr-11-3209. [PMID: 22589396]
  • Ruchi Sharma, Mark J Sharrard, Daniel J Connolly, Santosh R Mordekar. Unilateral periventricular leukomalacia in association with pyruvate dehydrogenase deficiency. Developmental medicine and child neurology. 2012 May; 54(5):469-71. doi: 10.1111/j.1469-8749.2011.04108.x. [PMID: 21895644]
  • Yue-Ping Wang, Man-Long Qi, Ting-Ting Li, Yun-Jing Zhao. Two novel mutations in the BCKDHB gene (R170H, Q346R) cause the classic form of maple syrup urine disease (MSUD). Gene. 2012 Apr; 498(1):112-5. doi: 10.1016/j.gene.2012.01.082. [PMID: 22326532]
  • Alessandra Folda, Anna Citta, Guido Scutari, Alberto Bindoli, Maria Pia Rigobello. Contrasting effects of selenite and tellurite on lipoamide dehydrogenase activity suggest a different biological behaviour of the two chalcogens. Archives of biochemistry and biophysics. 2012 Jan; 517(1):30-6. doi: 10.1016/j.abb.2011.11.009. [PMID: 22100759]
  • Patrick M Finnegan, Weihua Chen. Arsenic toxicity: the effects on plant metabolism. Frontiers in physiology. 2012; 3(?):182. doi: 10.3389/fphys.2012.00182. [PMID: 22685440]
  • Johannes A Mayr, Franz A Zimmermann, Christine Fauth, Christa Bergheim, David Meierhofer, Doris Radmayr, Johannes Zschocke, Johannes Koch, Wolfgang Sperl. Lipoic acid synthetase deficiency causes neonatal-onset epilepsy, defective mitochondrial energy metabolism, and glycine elevation. American journal of human genetics. 2011 Dec; 89(6):792-7. doi: 10.1016/j.ajhg.2011.11.011. [PMID: 22152680]
  • Jill Casteel, Ján A Miernyk, Jay J Thelen. Mapping the lipoylation site of Arabidopsis thaliana plastidial dihydrolipoamide S-acetyltransferase using mass spectrometry and site-directed mutagenesis. Plant physiology and biochemistry : PPB. 2011 Nov; 49(11):1355-61. doi: 10.1016/j.plaphy.2011.07.001. [PMID: 21798751]
  • Ekaterina A Savrasova, Aleksander D Kivero, Rustem S Shakulov, Nataliya V Stoynova. Use of the valine biosynthetic pathway to convert glucose into isobutanol. Journal of industrial microbiology & biotechnology. 2011 Sep; 38(9):1287-94. doi: 10.1007/s10295-010-0907-2. [PMID: 21161324]
  • Sanna Auer, Martin Nirschl, Matthias Schreiter, Inger Vikholm-Lundin. Detection of DNA hybridisation in a diluted serum matrix by surface plasmon resonance and film bulk acoustic resonators. Analytical and bioanalytical chemistry. 2011 May; 400(5):1387-96. doi: 10.1007/s00216-011-4871-0. [PMID: 21472364]
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  • Nicola Brunetti-Pierri, Brendan Lanpher, Ayelet Erez, Elitsa A Ananieva, Mohammad Islam, Juan C Marini, Qin Sun, Chunli Yu, Madhuri Hegde, Jun Li, R Max Wynn, David T Chuang, Susan Hutson, Brendan Lee. Phenylbutyrate therapy for maple syrup urine disease. Human molecular genetics. 2011 Feb; 20(4):631-40. doi: 10.1093/hmg/ddq507. [PMID: 21098507]
  • Matjaž Simončič, Tadeja Režen, Peter Juvan, Damjana Rozman, Gregor Fazarinc, Catherine Fievet, Bart Staels, Simon Horvat. Obesity resistant mechanisms in the Lean polygenic mouse model as indicated by liver transcriptome and expression of selected genes in skeletal muscle. BMC genomics. 2011 Feb; 12(?):96. doi: 10.1186/1471-2164-12-96. [PMID: 21291556]
  • Olav A Christophersen, Anna Haug. Animal products, diseases and drugs: a plea for better integration between agricultural sciences, human nutrition and human pharmacology. Lipids in health and disease. 2011 Jan; 10(?):16. doi: 10.1186/1476-511x-10-16. [PMID: 21247506]
  • Peng Chen, Qiu-Gang Ma, Cheng Ji, Jian-Yun Zhang, Li-Hong Zhao, Yong Zhang, Yong-Ze Jie. Dietary lipoic acid influences antioxidant capability and oxidative status of broilers. International journal of molecular sciences. 2011; 12(12):8476-88. doi: 10.3390/ijms12128476. [PMID: 22272085]
  • Hyung-Doo Park, Dong Hwan Lee, Yong Hee Hong, Dong Hee Kang, You Kyoung Lee, Junghan Song, Soo-Youn Lee, Jong-Won Kim, Chang-Seok Ki, Yong-Wha Lee. Three Korean patients with maple syrup urine disease: four novel mutations in the BCKDHA gene. Annals of clinical and laboratory science. 2011; 41(2):167-73. doi: . [PMID: 21844576]
  • Jian Wang, Hongjing Liu, Guoqiang Chen, Sian Hsiang-Te Tsuei, Tingting Yu, Qihua Fu. Identification of two novel BCKDHA mutations in a Chinese patient with maple syrup urine disease. Journal of pediatric endocrinology & metabolism : JPEM. 2011; 24(9-10):827-9. doi: 10.1515/jpem.2011.278. [PMID: 22145486]
  • Wayne Chadwick, Randall Brenneman, Bronwen Martin, Stuart Maudsley. Complex and multidimensional lipid raft alterations in a murine model of Alzheimer's disease. International journal of Alzheimer's disease. 2010 Dec; 2010(?):604792. doi: 10.4061/2010/604792. [PMID: 21151659]
  • Cheol Soo Choi, Pushpankur Ghoshal, Malathi Srinivasan, Sheene Kim, Gary Cline, Mulchand S Patel. Liver-specific pyruvate dehydrogenase complex deficiency upregulates lipogenesis in adipose tissue and improves peripheral insulin sensitivity. Lipids. 2010 Nov; 45(11):987-95. doi: 10.1007/s11745-010-3470-8. [PMID: 20835892]
  • Weihua Chen, Yingjun Chi, Nicolas L Taylor, Hans Lambers, Patrick M Finnegan. Disruption of ptLPD1 or ptLPD2, genes that encode isoforms of the plastidial lipoamide dehydrogenase, confers arsenate hypersensitivity in Arabidopsis. Plant physiology. 2010 Jul; 153(3):1385-97. doi: 10.1104/pp.110.153452. [PMID: 20488895]
  • Chiaki Kusumoto, Tomoyo Kinugawa, Hitoshi Morikawa, Mari Teraoka, Tadashi Nishida, Yoshikazu Murawaki, Kazuo Yamada, Tatsuya Matsura. Protection by Exogenously Added Coenzyme Q(9) against Free Radical-Induced Injuries in Human Liver Cells. Journal of clinical biochemistry and nutrition. 2010 May; 46(3):244-51. doi: 10.3164/jcbn.09-128. [PMID: 20490320]
  • Markus Karl Wiltafsky, Michael Walter Pfaffl, Franz Xaver Roth. The effects of branched-chain amino acid interactions on growth performance, blood metabolites, enzyme kinetics and transcriptomics in weaned pigs. The British journal of nutrition. 2010 Apr; 103(7):964-76. doi: 10.1017/s0007114509992212. [PMID: 20196890]
  • Hideki Matsumoto, Keiichi Akita, Ryosei Sakai, Yoshiharu Shimomura. Analysis of branched-chain alpha-keto acid dehydrogenase complex activity in rat tissues using alpha-keto[1-13C]isocaproate as substrate. Analytical biochemistry. 2010 Apr; 399(1):1-6. doi: 10.1016/j.ab.2009.12.017. [PMID: 20018161]
  • Stephanie M Carleton, Dawn S Peck, Julie Grasela, Kristin L Dietiker, Charlotte L Phillips. DNA carrier testing and newborn screening for maple syrup urine disease in Old Order Mennonite communities. Genetic testing and molecular biomarkers. 2010 Apr; 14(2):205-8. doi: 10.1089/gtmb.2009.0107. [PMID: 20136525]
  • Kornelia Edes, Pamela Cassidy, Paul J Shami, Philip J Moos. JS-K, a nitric oxide prodrug, has enhanced cytotoxicity in colon cancer cells with knockdown of thioredoxin reductase 1. PloS one. 2010 Jan; 5(1):e8786. doi: 10.1371/journal.pone.0008786. [PMID: 20098717]
  • Sabrina Le Bouter, Marianne Rodriguez, Nolwen Guigal-Stephan, Sophie Courtade-Gaïani, Laura Xuereb, Catherine de Montrion, Vincent Croixmarie, Thierry Umbdenstock, Claire Boursier-Neyret, Michel Lonchampt, Manuel Brun, Catherine Dacquet, Alain Ktorza, Brian-Paul Lockhart, Jean-Pierre Galizzi. Coordinate Transcriptomic and Metabolomic Effects of the Insulin Sensitizer Rosiglitazone on Fundamental Metabolic Pathways in Liver, Soleus Muscle, and Adipose Tissue in Diabetic db/db Mice. PPAR research. 2010; 2010(?):. doi: 10.1155/2010/679184. [PMID: 20953342]
  • Theodoros Georgiou, Jacinta L Chuang, R Max Wynn, Goula Stylianidou, Mark Korson, David T Chuang, Anthi Drousiotou. Maple syrup urine disease in Cypriot families: identification of three novel mutations and biochemical characterization of the p.Thr211Met mutation in the E1alpha subunit. Genetic testing and molecular biomarkers. 2009 Oct; 13(5):657-64. doi: 10.1089/gtmb.2009.0065. [PMID: 19715473]
  • Gustavo Bajotto, Taro Murakami, Masaru Nagasaki, Yuzo Sato, Yoshiharu Shimomura. Decreased enzyme activity and contents of hepatic branched-chain alpha-keto acid dehydrogenase complex subunits in a rat model for type 2 diabetes mellitus. Metabolism: clinical and experimental. 2009 Oct; 58(10):1489-95. doi: 10.1016/j.metabol.2009.04.029. [PMID: 19586643]
  • Tadeja Rezen, Viola Tamasi, Anita Lövgren-Sandblom, Ingemar Björkhem, Urs A Meyer, Damjana Rozman. Effect of CAR activation on selected metabolic pathways in normal and hyperlipidemic mouse livers. BMC genomics. 2009 Aug; 10(?):384. doi: 10.1186/1471-2164-10-384. [PMID: 19691840]
  • Kristen J Skvorak, Harbhajan S Paul, Kenneth Dorko, Fabio Marongiu, Ewa Ellis, Donald Chace, Carolyn Ferguson, K Michael Gibson, Gregg E Homanics, Stephen C Strom. Hepatocyte transplantation improves phenotype and extends survival in a murine model of intermediate maple syrup urine disease. Molecular therapy : the journal of the American Society of Gene Therapy. 2009 Jul; 17(7):1266-73. doi: 10.1038/mt.2009.99. [PMID: 19436271]
  • Gang Lu, Haipeng Sun, Pengxiang She, Ji-Youn Youn, Sarah Warburton, Peipei Ping, Thomas M Vondriska, Hua Cai, Christopher J Lynch, Yibin Wang. Protein phosphatase 2Cm is a critical regulator of branched-chain amino acid catabolism in mice and cultured cells. The Journal of clinical investigation. 2009 Jun; 119(6):1678-87. doi: 10.1172/jci38151. [PMID: 19411760]
  • Sofia Quental, Alfredo Gusmão, Pilar Rodríguez-Pombo, Magdalena Ugarte, Laura Vilarinho, António Amorim, Maria J Prata. Revisiting MSUD in Portuguese Gypsies: evidence for a founder mutation and for a mutational hotspot within the BCKDHA gene. Annals of human genetics. 2009 May; 73(Pt 3):298-303. doi: 10.1111/j.1469-1809.2009.00518.x. [PMID: 19456321]
  • K J Skvorak. Animal models of maple syrup urine disease. Journal of inherited metabolic disease. 2009 Apr; 32(2):229-46. doi: 10.1007/s10545-009-1086-z. [PMID: 19263237]
  • Viacheslav V Dolgikh, Elena V Seliverstova, Anton M Naumov, Igor V Senderskiy, Olga A Pavlova, Galina V Beznoussenko. Heterologous expression of pyruvate dehydrogenase E1 subunits of the microsporidium Paranosema (Antonospora) locustae and immunolocalization of the mitochondrial protein in amitochondrial cells. FEMS microbiology letters. 2009 Apr; 293(2):285-91. doi: 10.1111/j.1574-6968.2009.01545.x. [PMID: 19260967]
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