Saccharopine (BioDeep_00000400291)

Main id: BioDeep_00000001373

 

natural product PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


L-Saccharopine

化学式: C11H20N2O6 (276.13213)
中文名称: L-酵母氨酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(CCNC(CCC(=O)O)C(=O)O)CC(C(=O)O)N
InChI: InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1

描述信息

The N(6)-(1,3-dicarboxypropan-1-yl) derivative of L-lysine.

同义名列表

3 个代谢物同义名

L-Saccharopine; Saccharopine; N6-(L-1,3-Dicarboxypropyl)-L-lysine



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

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)

27 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

  • Brian J Koos, Jeffrey A Gornbein. Early pregnancy metabolites predict gestational diabetes mellitus: implications for fetal programming. American journal of obstetrics and gynecology. 2021 02; 224(2):215.e1-215.e7. doi: 10.1016/j.ajog.2020.07.050. [PMID: 32739399]
  • Ulf H Beier, Erum A Hartung, Seth Concors, Paul T Hernandez, Zhonglin Wang, Caroline Perry, Joseph A Baur, Michelle R Denburg, Wayne W Hancock, Terence P Gade, Matthew H Levine. Tissue metabolic profiling shows that saccharopine accumulates during renal ischemic-reperfusion injury, while kynurenine and itaconate accumulate in renal allograft rejection. Metabolomics : Official journal of the Metabolomic Society. 2020 05; 16(5):65. doi: 10.1007/s11306-020-01682-2. [PMID: 32367163]
  • Artem V Artiukhov, Aneta Grabarska, Ewelina Gumbarewicz, Vasily A Aleshin, Thilo Kähne, Toshihiro Obata, Alexey V Kazantsev, Nikolay V Lukashev, Andrzej Stepulak, Alisdair R Fernie, Victoria I Bunik. Synthetic analogues of 2-oxo acids discriminate metabolic contribution of the 2-oxoglutarate and 2-oxoadipate dehydrogenases in mammalian cells and tissues. Scientific reports. 2020 02; 10(1):1886. doi: 10.1038/s41598-020-58701-4. [PMID: 32024885]
  • Junxiang Zhou, Xin Wang, Min Wang, Yuwei Chang, Fengxia Zhang, Zhaonan Ban, Ruofeng Tang, Qiwen Gan, Shaohuan Wu, Ye Guo, Qian Zhang, Fengyang Wang, Liyuan Zhao, Yudong Jing, Wenfeng Qian, Guodong Wang, Weixiang Guo, Chonglin Yang. The lysine catabolite saccharopine impairs development by disrupting mitochondrial homeostasis. The Journal of cell biology. 2019 02; 218(2):580-597. doi: 10.1083/jcb.201807204. [PMID: 30573525]
  • Izabella Agostinho Pena, Lygia Azevedo Marques, Ângelo B A Laranjeira, José A Yunes, Marcos N Eberlin, Alex MacKenzie, Paulo Arruda. Mouse lysine catabolism to aminoadipate occurs primarily through the saccharopine pathway; implications for pyridoxine dependent epilepsy (PDE). Biochimica et biophysica acta. Molecular basis of disease. 2017 01; 1863(1):121-128. doi: 10.1016/j.bbadis.2016.09.006. [PMID: 27615426]
  • Genya Watanabe, Hiroyuki Kobayashi, Masahiro Shibata, Masatoshi Kubota, Motoni Kadowaki, Shinobu Fujimura. Regulation of free glutamate content in meat by dietary lysine in broilers. Animal science journal = Nihon chikusan Gakkaiho. 2015 Apr; 86(4):435-42. doi: 10.1111/asj.12321. [PMID: 25491790]
  • Antonella Rosi, Lucia Ricci-Vitiani, Mauro Biffoni, Sveva Grande, Anna Maria Luciani, Alessandra Palma, Daniele Runci, Marianna Cappellari, Ruggero De Maria, Laura Guidoni, Roberto Pallini, Vincenza Viti. (1) H NMR spectroscopy of glioblastoma stem-like cells identifies alpha-aminoadipate as a marker of tumor aggressiveness. NMR in biomedicine. 2015 Mar; 28(3):317-26. doi: 10.1002/nbm.3254. [PMID: 25581615]
  • Guilherme Coutinho de Mello Serrano, Thaís Rezende e Silva Figueira, Eduardo Kiyota, Natalia Zanata, Paulo Arruda. Lysine degradation through the saccharopine pathway in bacteria: LKR and SDH in bacteria and its relationship to the plant and animal enzymes. FEBS letters. 2012 Mar; 586(6):905-11. doi: 10.1016/j.febslet.2012.02.023. [PMID: 22449979]
  • Yi Shen, Yan Zhang, Chao Yang, Ying Lan, Linglong Liu, Shijia Liu, Zhijun Chen, Guixin Ren, Jianmin Wan. Mutation of OsALDH7 causes a yellow-colored endosperm associated with accumulation of oryzamutaic acid A in rice. Planta. 2012 Feb; 235(2):433-41. doi: 10.1007/s00425-011-1477-x. [PMID: 21960163]
  • R L M Guedes, F Prosdocimi, G R Fernandes, L K Moura, H A L Ribeiro, J M Ortega. Amino acids biosynthesis and nitrogen assimilation pathways: a great genomic deletion during eukaryotes evolution. BMC genomics. 2011 Dec; 12 Suppl 4(?):S2. doi: 10.1186/1471-2164-12-s4-s2. [PMID: 22369087]
  • Grant R Cramer, Kaoru Urano, Serge Delrot, Mario Pezzotti, Kazuo Shinozaki. Effects of abiotic stress on plants: a systems biology perspective. BMC plant biology. 2011 Nov; 11(?):163. doi: 10.1186/1471-2229-11-163. [PMID: 22094046]
  • Julien Bouchoux, Frauke Beilstein, Thomas Pauquai, I Chiara Guerrera, Danielle Chateau, Nathalie Ly, Malik Alqub, Christophe Klein, Jean Chambaz, Monique Rousset, Jean-Marc Lacorte, Etienne Morel, Sylvie Demignot. The proteome of cytosolic lipid droplets isolated from differentiated Caco-2/TC7 enterocytes reveals cell-specific characteristics. Biology of the cell. 2011 Nov; 103(11):499-517. doi: 10.1042/bc20110024. [PMID: 21787361]
  • Desmond B S Pink, Stephanie K Gatrell, Rajavel Elango, Joan Turchinsky, Aaron S Kiess, Kenneth P Blemings, Walter T Dixon, Ronald O Ball. Lysine α-ketoglutarate reductase, but not saccharopine dehydrogenase, is subject to substrate inhibition in pig liver. Nutrition research (New York, N.Y.). 2011 Jul; 31(7):544-54. doi: 10.1016/j.nutres.2011.06.001. [PMID: 21840471]
  • Sven W Sauer, Silvana Opp, Georg F Hoffmann, David M Koeller, Jürgen G Okun, Stefan Kölker. Therapeutic modulation of cerebral L-lysine metabolism in a mouse model for glutaric aciduria type I. Brain : a journal of neurology. 2011 Jan; 134(Pt 1):157-70. doi: 10.1093/brain/awq269. [PMID: 20923787]
  • Taiji Kawakatsu, Fumio Takaiwa. Differences in transcriptional regulatory mechanisms functioning for free lysine content and seed storage protein accumulation in rice grain. Plant & cell physiology. 2010 Dec; 51(12):1964-74. doi: 10.1093/pcp/pcq164. [PMID: 21037241]
  • L Aravind, Robson F de Souza, Lakshminarayan M Iyer. Predicted class-I aminoacyl tRNA synthetase-like proteins in non-ribosomal peptide synthesis. Biology direct. 2010 Aug; 5(?):48. doi: 10.1186/1745-6150-5-48. [PMID: 20678224]
  • Wagner L Araújo, Kimitsune Ishizaki, Adriano Nunes-Nesi, Tony R Larson, Takayuki Tohge, Ina Krahnert, Sandra Witt, Toshihiro Obata, Nicolas Schauer, Ian A Graham, Christopher J Leaver, Alisdair R Fernie. Identification of the 2-hydroxyglutarate and isovaleryl-CoA dehydrogenases as alternative electron donors linking lysine catabolism to the electron transport chain of Arabidopsis mitochondria. The Plant cell. 2010 May; 22(5):1549-63. doi: 10.1105/tpc.110.075630. [PMID: 20501910]
  • Raquel González-Fernández, Elena Prats, Jesús V Jorrín-Novo. Proteomics of plant pathogenic fungi. Journal of biomedicine & biotechnology. 2010; 2010(?):932527. doi: 10.1155/2010/932527. [PMID: 20589070]
  • Banzragch Battur, Damdinsuren Boldbaatar, Rika Umemiya-Shirafuji, Min Liao, Badgar Battsetseg, DeMar Taylor, Badarch Baymbaa, Kozo Fujisaki. LKR/SDH plays important roles throughout the tick life cycle including a long starvation period. PloS one. 2009 Sep; 4(9):e7136. doi: 10.1371/journal.pone.0007136. [PMID: 19774086]
  • Sun-Jung Kwon, Sang-Yun Cho, Kyung-Mi Lee, Jisuk Yu, Moonil Son, Kook-Hyung Kim. Proteomic analysis of fungal host factors differentially expressed by Fusarium graminearum infected with Fusarium graminearum virus-DK21. Virus research. 2009 Sep; 144(1-2):96-106. doi: 10.1016/j.virusres.2009.04.004. [PMID: 19374926]
  • Laura Valdés-Santiago, José A Cervantes-Chávez, José Ruiz-Herrera. Ustilago maydis spermidine synthase is encoded by a chimeric gene, required for morphogenesis, and indispensable for survival in the host. FEMS yeast research. 2009 Sep; 9(6):923-35. doi: 10.1111/j.1567-1364.2009.00539.x. [PMID: 19624748]
  • Paul Francis Morris, Laura Rose Schlosser, Katherine Diane Onasch, Tom Wittenschlaeger, Ryan Austin, Nicholas Provart. Multiple horizontal gene transfer events and domain fusions have created novel regulatory and metabolic networks in the oomycete genome. PloS one. 2009 Jul; 4(7):e6133. doi: 10.1371/journal.pone.0006133. [PMID: 19582169]
  • Andrej Benjak, Stéphanie Boué, Astrid Forneck, Josep M Casacuberta. Recent amplification and impact of MITEs on the genome of grapevine (Vitis vinifera L.). Genome biology and evolution. 2009 May; 1(?):75-84. doi: 10.1093/gbe/evp009. [PMID: 20333179]
  • Kaoru Urano, Kyonoshin Maruyama, Yoshiyuki Ogata, Yoshihiko Morishita, Migiwa Takeda, Nozomu Sakurai, Hideyuki Suzuki, Kazuki Saito, Daisuke Shibata, Masatomo Kobayashi, Kazuko Yamaguchi-Shinozaki, Kazuo Shinozaki. Characterization of the ABA-regulated global responses to dehydration in Arabidopsis by metabolomics. The Plant journal : for cell and molecular biology. 2009 Mar; 57(6):1065-78. doi: 10.1111/j.1365-313x.2008.03748.x. [PMID: 19036030]
  • Allan R Reyes, Christopher P Bonin, Nancy M Houmard, Shihshieh Huang, Thomas M Malvar. Genetic manipulation of lysine catabolism in maize kernels. Plant molecular biology. 2009 Jan; 69(1-2):81-9. doi: 10.1007/s11103-008-9409-2. [PMID: 18839315]
  • Michael Hansen, Carsten Friis, Steve Bowra, Preben Bach Holm, Eva Vincze. A pathway-specific microarray analysis highlights the complex and co-ordinated transcriptional networks of the developing grain of field-grown barley. Journal of experimental botany. 2009; 60(1):153-67. doi: 10.1093/jxb/ern270. [PMID: 19015218]
  • Gilles Curien, Olivier Bastien, Mylène Robert-Genthon, Athel Cornish-Bowden, María Luz Cárdenas, Renaud Dumas. Understanding the regulation of aspartate metabolism using a model based on measured kinetic parameters. Molecular systems biology. 2009; 5(?):271. doi: 10.1038/msb.2009.29. [PMID: 19455135]
  • J Schildhauer, K Wiedemuth, K Humbeck. Supply of nitrogen can reverse senescence processes and affect expression of genes coding for plastidic glutamine synthetase and lysine-ketoglutarate reductase/saccharopine dehydrogenase. Plant biology (Stuttgart, Germany). 2008 Sep; 10 Suppl 1(?):76-84. doi: 10.1111/j.1438-8677.2008.00075.x. [PMID: 18721313]
  • Alessandra Frizzi, Shihshieh Huang, Larry A Gilbertson, Toni A Armstrong, Michael H Luethy, Thomas M Malvar. Modifying lysine biosynthesis and catabolism in corn with a single bifunctional expression/silencing transgene cassette. Plant biotechnology journal. 2008 Jan; 6(1):13-21. doi: 10.1111/j.1467-7652.2007.00290.x. [PMID: 17725550]
  • Tunahan Cakir, Selma Alsan, Hale Saybaşili, Ata Akin, Kutlu O Ulgen. Reconstruction and flux analysis of coupling between metabolic pathways of astrocytes and neurons: application to cerebral hypoxia. Theoretical biology & medical modelling. 2007 Dec; 4(?):48. doi: 10.1186/1742-4682-4-48. [PMID: 18070347]
  • Miyako Kusano, Atsushi Fukushima, Masanori Arita, Pär Jonsson, Thomas Moritz, Makoto Kobayashi, Naomi Hayashi, Takayuki Tohge, Kazuki Saito. Unbiased characterization of genotype-dependent metabolic regulations by metabolomic approach in Arabidopsis thaliana. BMC systems biology. 2007 Nov; 1(?):53. doi: 10.1186/1752-0509-1-53. [PMID: 18028551]
  • Nancy M Houmard, Jonnelle L Mainville, Christopher P Bonin, Shihshieh Huang, Michael H Luethy, Thomas M Malvar. High-lysine corn generated by endosperm-specific suppression of lysine catabolism using RNAi. Plant biotechnology journal. 2007 Sep; 5(5):605-14. doi: 10.1111/j.1467-7652.2007.00265.x. [PMID: 17553105]
  • M Moulin, C Deleu, F Larher, A Bouchereau. The lysine-ketoglutarate reductase-saccharopine dehydrogenase is involved in the osmo-induced synthesis of pipecolic acid in rapeseed leaf tissues. Plant physiology and biochemistry : PPB. 2006 Jul; 44(7-9):474-82. doi: 10.1016/j.plaphy.2006.08.005. [PMID: 17023168]
  • A Stepansky, H Less, R Angelovici, R Aharon, X Zhu, G Galili. Lysine catabolism, an effective versatile regulator of lysine level in plants. Amino acids. 2006 Mar; 30(2):121-5. doi: 10.1007/s00726-005-0246-1. [PMID: 16525756]
  • Ricardo F Fornazier, Salete A Gaziola, Cristiane V Helm, Peter J Lea, Ricardo A Azevedo. Isolation and characterization of enzymes involved in lysine catabolism from sorghum seeds. Journal of agricultural and food chemistry. 2005 Mar; 53(5):1791-8. doi: 10.1021/jf048525o. [PMID: 15740075]
  • Asya Stepansky, Youli Yao, Guiliang Tang, G Galili. Regulation of lysine catabolism in Arabidopsis through concertedly regulated synthesis of the two distinct gene products of the composite AtLKR/SDH locus. Journal of experimental botany. 2005 Feb; 56(412):525-36. doi: 10.1093/jxb/eri031. [PMID: 15569707]
  • Ricardo A Azevedo, Catherine Damerval, Jacques Landry, Peter J Lea, Cláudia M Bellato, Lyndel W Meinhardt, Martine Le Guilloux, Sonia Delhaye, Alejandro A Toro, Salete A Gaziola, Bertha D A Berdejo. Regulation of maize lysine metabolism and endosperm protein synthesis by opaque and floury mutations. European journal of biochemistry. 2003 Dec; 270(24):4898-908. doi: 10.1111/j.1432-1033.2003.03890.x. [PMID: 14653816]
  • Asya Stepansky, Gad Galili. Synthesis of the Arabidopsis bifunctional lysine-ketoglutarate reductase/saccharopine dehydrogenase enzyme of lysine catabolism is concertedly regulated by metabolic and stress-associated signals. Plant physiology. 2003 Nov; 133(3):1407-15. doi: 10.1104/pp.103.026294. [PMID: 14576281]
  • Xiaohong Zhu, Guiliang Tang, Gad Galili. The activity of the Arabidopsis bifunctional lysine-ketoglutarate reductase/saccharopine dehydrogenase enzyme of lysine catabolism is regulated by functional interaction between its two enzyme domains. The Journal of biological chemistry. 2002 Dec; 277(51):49655-61. doi: 10.1074/jbc.m205466200. [PMID: 12393892]
  • Guiliang Tang, Xiaohong Zhu, Bertrand Gakiere, Hanna Levanony, Anat Kahana, Gad Galili. The bifunctional LKR/SDH locus of plants also encodes a highly active monofunctional lysine-ketoglutarate reductase using a polyadenylation signal located within an intron. Plant physiology. 2002 Sep; 130(1):147-54. doi: 10.1104/pp.005660. [PMID: 12226495]
  • R A Azevedo. Analysis of the aspartic acid metabolic pathway using mutant genes. Amino acids. 2002; 22(3):217-30. doi: 10.1007/s007260200010. [PMID: 12083066]
  • X Zhu, G Tang, F Granier, D Bouchez, G Galili. A T-DNA insertion knockout of the bifunctional lysine-ketoglutarate reductase/saccharopine dehydrogenase gene elevates lysine levels in Arabidopsis seeds. Plant physiology. 2001 Aug; 126(4):1539-45. doi: 10.1104/pp.126.4.1539. [PMID: 11500552]
  • E Johansson, J J Steffens, Y Lindqvist, G Schneider. Crystal structure of saccharopine reductase from Magnaporthe grisea, an enzyme of the alpha-aminoadipate pathway of lysine biosynthesis. Structure (London, England : 1993). 2000 Oct; 8(10):1037-47. doi: 10.1016/s0969-2126(00)00512-8. [PMID: 11080625]
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