Ectoine (BioDeep_00000003008)

 

Secondary id: BioDeep_00000409645

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(4S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid

化学式: C6H10N2O2 (142.074224)
中文名称: 四氢嘧啶(依克多因), 四氢嘧啶
谱图信息: 最多检出来源 Homo sapiens(blood) 0.16%

分子结构信息

SMILES: CC(N1)=NC(CC1)C(O)=O
InChI: InChI=1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)

描述信息

Ectoine belongs to the class of organic compounds known as alpha-amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Ectoine has been identified in urine (PMID: 22409530).
CONFIDENCE standard compound; ML_ID 37
C26170 - Protective Agent
KEIO_ID E011
Ectoine is a natural cell protectant, an amino acid derivate produced by bacteria living under extremely harsh environmental conditions. Ectoine serves as an osmoregulatory compatible solute, increasing the hydration of the skin surface and stabilizing lipid layers, which is useful in skincare. Ectoine demonstrates a good safety profile for the treatment of allergic rhinitis[1][2].

同义名列表

15 个代谢物同义名

(4S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid; (4S)-3,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid; (4S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid; (S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid; (+)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid; (4S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylate; (+)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylate; 1,4,5,6-tetrahydro-2-Methyl-4-pyrimidinecarboxylic acid; Pyrostatine B; PYROSTATIN B; L-Ectoine; NSC614616; ectoine; Ectoin; Ectoine



数据库引用编号

35 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

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)

74 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

  • Jun Chen, Deliang Qiao, Tao Yuan, Yeyuan Feng, Pengjun Zhang, Xuejun Wang, Li Zhang. Biotechnological production of ectoine: current status and prospects. Folia microbiologica. 2024 Apr; 69(2):247-258. doi: 10.1007/s12223-023-01105-4. [PMID: 37962826]
  • Yuhan Ma, Ping Huang, Shoucheng Huang, Uzma Younis, Ghulam Sabir Hussain, Shah Fahad, Subhan Danish, Mohamed Soliman Elshikh, Humaira Rizwana. γ-Aminobutyric acid (GABA) and ectoine (ECT) impacts with and without AMF on antioxidants, gas exchange attributes and nutrients of cotton cultivated in salt affected soil. BMC plant biology. 2023 Oct; 23(1):476. doi: 10.1186/s12870-023-04486-3. [PMID: 37807063]
  • Min Kyeong Kang, Jin-Won Park. Ectoine Effect on Mechanical Properties of Vesicles in Aqueous Solution. The Journal of membrane biology. 2022 02; 255(1):55-59. doi: 10.1007/s00232-021-00208-8. [PMID: 34751806]
  • Bhagwan Narayan Rekadwad, Wen-Jun Li, P D Rekha. The diversity of unique 1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid coding common genes and Universal stress protein in Ectoine TRAP cluster (UspA) in 32 Halomonas species. BMC research notes. 2021 Aug; 14(1):296. doi: 10.1186/s13104-021-05689-3. [PMID: 34344424]
  • Daniela S Nosch, Roland E Joos, Michael Job. Prospective randomized study to evaluate the efficacy and tolerability of Ectoin® containing Eye Spray (EES09) and comparison to the liposomal Eye Spray Tears Again® (TA) in the treatment of dry eye disease. Contact lens & anterior eye : the journal of the British Contact Lens Association. 2021 Jun; 44(3):101318. doi: 10.1016/j.clae.2020.04.003. [PMID: 32354652]
  • Lukas Bethlehem, Gerhild van Echten-Deckert. Ectoines as novel anti-inflammatory and tissue protective lead compounds with special focus on inflammatory bowel disease and lung inflammation. Pharmacological research. 2021 02; 164(?):105389. doi: 10.1016/j.phrs.2020.105389. [PMID: 33352226]
  • Tamer Elsakhawy, Azza Ghazi, Mohamed Ali Abdel-Rahman. Developing Liquid Rhizobium Inoculants with Enhanced Long-Term Survival, Storage Stability, and Plant Growth Promotion Using Ectoine Additive. Current microbiology. 2021 Jan; 78(1):282-291. doi: 10.1007/s00284-020-02265-z. [PMID: 33136205]
  • Jasmina Vandrich, Friedhelm Pfeiffer, Gabriela Alfaro-Espinoza, Hans Jörg Kunte. Contribution of mechanosensitive channels to osmoadaptation and ectoine excretion in Halomonas elongata. Extremophiles : life under extreme conditions. 2020 May; 24(3):421-432. doi: 10.1007/s00792-020-01168-y. [PMID: 32266565]
  • Salma Mukhtar, Samia Ahmad, Aftab Bashir, Samina Mehnaz, Muhammad Sajjad Mirza, Kauser Abdulla Malik. Identification of plasmid encoded osmoregulatory genes from halophilic bacteria isolated from the rhizosphere of halophytes. Microbiological research. 2019 Nov; 228(?):126307. doi: 10.1016/j.micres.2019.126307. [PMID: 31422229]
  • Marius Herzog, Mridula Dwivedi, Rakesh Kumar Harishchandra, Andreas Bilstein, Hans-Joachim Galla, Roland Winter. Effect of ectoine, hydroxyectoine and β-hydroxybutyrate on the temperature and pressure stability of phospholipid bilayer membranes of different complexity. Colloids and surfaces. B, Biointerfaces. 2019 Jun; 178(?):404-411. doi: 10.1016/j.colsurfb.2019.03.026. [PMID: 30903979]
  • Laura Czech, Sebastian Poehl, Philipp Hub, Nadine Stöveken, Erhard Bremer. Tinkering with Osmotically Controlled Transcription Allows Enhanced Production and Excretion of Ectoine and Hydroxyectoine from a Microbial Cell Factory. Applied and environmental microbiology. 2018 01; 84(2):. doi: 10.1128/aem.01772-17. [PMID: 29101191]
  • Klaus Unfried, Ursula Krämer, Ulrich Sydlik, Andrea Autengruber, Andreas Bilstein, Sabine Stolz, Alessandra Marini, Tamara Schikowski, Stefanie Keymel, Jean Krutmann. Reduction of neutrophilic lung inflammation by inhalation of the compatible solute ectoine: a randomized trial with elderly individuals. International journal of chronic obstructive pulmonary disease. 2016; 11(?):2573-2583. doi: 10.2147/copd.s115061. [PMID: 27799756]
  • ZhiHui Shao, WanXin Deng, ShiYuan Li, JuanMei He, ShuangXi Ren, WeiRen Huang, YinHua Lu, GuoPing Zhao, ZhiMing Cai, Jin Wang. GlnR-Mediated Regulation of ectABCD Transcription Expands the Role of the GlnR Regulon to Osmotic Stress Management. Journal of bacteriology. 2015 Oct; 197(19):3041-7. doi: 10.1128/jb.00185-15. [PMID: 26170409]
  • Tomohiro Osaki, Seiji Kurozumi, Kimihiko Sato, Taro Terashi, Kazuo Azuma, Yusuke Murahata, Takeshi Tsuka, Norihiko Ito, Tomohiro Imagawa, Saburo Minami, Yoshiharu Okamoto. Metabolomic Analysis of Blood Plasma after Oral Administration of N-acetyl-d-Glucosamine in Dogs. Marine drugs. 2015 Aug; 13(8):5007-15. doi: 10.3390/md13085007. [PMID: 26262626]
  • Mridula Dwivedi, Hannes Backers, Rakesh Kumar Harishchandra, Hans-Joachim Galla. Biophysical investigations of the structure and function of the tear fluid lipid layer and the effect of ectoine. Part A: natural meibomian lipid films. Biochimica et biophysica acta. 2014 Oct; 1838(10):2708-15. doi: 10.1016/j.bbamem.2014.05.011. [PMID: 24841755]
  • Mridula Dwivedi, Marc Brinkkötter, Rakesh Kumar Harishchandra, Hans-Joachim Galla. Biophysical investigations of the structure and function of the tear fluid lipid layers and the effect of ectoine. Part B: artificial lipid films. Biochimica et biophysica acta. 2014 Oct; 1838(10):2716-27. doi: 10.1016/j.bbamem.2014.05.007. [PMID: 24853656]
  • A Wedeking, N Hagen-Euteneuer, M Gurgui, R Broere, G Lentzen, R H Tolba, E Galinski, G van Echten-Deckert. A lipid anchor improves the protective effect of ectoine in inflammation. Current medicinal chemistry. 2014; 21(22):2565-72. doi: 10.2174/0929867321666131228222730. [PMID: 24372204]
  • Andrea Eichel, Jo Wittig, Kija Shah-Hosseini, Ralph Mösges. A prospective, controlled study of SNS01 (ectoine nasal spray) compared to BNO-101 (phytotherapeutic dragées) in patients with acute rhinosinusitis. Current medical research and opinion. 2013 Jul; 29(7):739-46. doi: 10.1185/03007995.2013.800474. [PMID: 23621514]
  • Thomas Pech, Ichiro Ohsawa, Michael Praktiknjo, Marcus Overhaus, Sven Wehner, Martin von Websky, Kareem Abu-Elmagd, Gerhild van Echten-Deckert, Joerg C Kalff, Nico Schaefer. A natural tetrahydropyrimidine, ectoine, ameliorates ischemia reperfusion injury after intestinal transplantation in rats. Pathobiology : journal of immunopathology, molecular and cellular biology. 2013; 80(2):102-10. doi: 10.1159/000342792. [PMID: 23108005]
  • Henrike Peuschel, Ulrich Sydlik, Susanne Grether-Beck, Ingo Felsner, Daniel Stöckmann, Sascha Jakob, Matthias Kroker, Judith Haendeler, Marijan Gotić, Christiane Bieschke, Jean Krutmann, Klaus Unfried. Carbon nanoparticles induce ceramide- and lipid raft-dependent signalling in lung epithelial cells: a target for a preventive strategy against environmentally-induced lung inflammation. Particle and fibre toxicology. 2012 Dec; 9(?):48. doi: 10.1186/1743-8977-9-48. [PMID: 23228165]
  • Rakesh Kumar Harishchandra, Amit Kumar Sachan, Andreas Kerth, Georg Lentzen, Thorsten Neuhaus, Hans-Joachim Galla. Compatible solutes: ectoine and hydroxyectoine improve functional nanostructures in artificial lung surfactants. Biochimica et biophysica acta. 2011 Dec; 1808(12):2830-40. doi: 10.1016/j.bbamem.2011.08.022. [PMID: 21889490]
  • Takafumi Toyohara, Takehiro Suzuki, Yasutoshi Akiyama, Daisuke Yoshihara, Yoichi Takeuchi, Eikan Mishima, Koichi Kikuchi, Chitose Suzuki, Masayuki Tanemoto, Sadayoshi Ito, Shizuko Nagao, Tomoyoshi Soga, Takaaki Abe. Metabolomic profiling of the autosomal dominant polycystic kidney disease rat model. Clinical and experimental nephrology. 2011 Oct; 15(5):676-687. doi: 10.1007/s10157-011-0467-4. [PMID: 21695416]
  • Reda E A Moghaieb, Akiko Nakamura, Hirofumi Saneoka, Kounosuke Fujita. Evaluation of salt tolerance in ectoine-transgenic tomato plants (Lycopersicon esculentum) in terms of photosynthesis, osmotic adjustment, and carbon partitioning. GM crops. 2011 Jan; 2(1):58-65. doi: 10.4161/gmcr.2.1.15831. [PMID: 21844699]
  • Basilio Zafrilla, Rosa M Martínez-Espinosa, María A Alonso, María J Bonete. Biodiversity of Archaea and floral of two inland saltern ecosystems in the Alto Vinalopó Valley, Spain. Saline systems. 2010 Oct; 6(?):10. doi: 10.1186/1746-1448-6-10. [PMID: 20942947]
  • Rakesh Kumar Harishchandra, Stephanie Wulff, Georg Lentzen, Thorsten Neuhaus, Hans-Joachim Galla. The effect of compatible solute ectoines on the structural organization of lipid monolayer and bilayer membranes. Biophysical chemistry. 2010 Aug; 150(1-3):37-46. doi: 10.1016/j.bpc.2010.02.007. [PMID: 20206435]
  • Matthias Kurz, Adrien Y Burch, Britta Seip, Steven E Lindow, Harald Gross. Genome-driven investigation of compatible solute biosynthesis pathways of Pseudomonas syringae pv. syringae and their contribution to water stress tolerance. Applied and environmental microbiology. 2010 Aug; 76(16):5452-62. doi: 10.1128/aem.00686-10. [PMID: 20581190]
  • Aharon Oren. Industrial and environmental applications of halophilic microorganisms. Environmental technology. 2010 Jul; 31(8-9):825-34. doi: 10.1080/09593330903370026. [PMID: 20662374]
  • Tanja A Grein, Denise Freimark, Christian Weber, Klaus Hudel, Christine Wallrapp, Peter Czermak. Alternatives to dimethylsulfoxide for serum-free cryopreservation of human mesenchymal stem cells. The International journal of artificial organs. 2010 Jun; 33(6):370-80. doi: . [PMID: 20669142]
  • Daniel Appel, Georg Lentzen. The pyrostatins A and B do not inhibit N-acetyl-beta-D-glucosaminidase. Journal of enzyme inhibition and medicinal chemistry. 2009 Oct; 24(5):1106-8. doi: 10.1080/14756360802632831. [PMID: 19555187]
  • Stephan Klähn, Daniel M Marquardt, Inga Rollwitz, Martin Hagemann. Expression of the ggpPS gene for glucosylglycerol biosynthesis from Azotobacter vinelandii improves the salt tolerance of Arabidopsis thaliana. Journal of experimental botany. 2009; 60(6):1679-89. doi: 10.1093/jxb/erp030. [PMID: 19363207]
  • Aharon Oren. Microbial life at high salt concentrations: phylogenetic and metabolic diversity. Saline systems. 2008 Apr; 4(?):2. doi: 10.1186/1746-1448-4-2. [PMID: 18412960]
  • Isseki Yu, Yoichi Jindo, Masataka Nagaoka. Microscopic understanding of preferential exclusion of compatible solute ectoine: direct interaction and hydration alteration. The journal of physical chemistry. B. 2007 Aug; 111(34):10231-8. doi: 10.1021/jp068367z. [PMID: 17676787]
  • T P Cañamás, I Viñas, J Usall, N Magan, J R Morelló, N Teixidó. Relative importance of amino acids, glycine-betaine and ectoine synthesis in the biocontrol agent Pantoea agglomerans CPA-2 in response to osmotic, acidic and heat stress. Letters in applied microbiology. 2007 Jul; 45(1):6-12. doi: 10.1111/j.1472-765x.2007.02156.x. [PMID: 17594453]
  • Sandra Cornacchione, Neil S Sadick, Michele Neveu, Sylvie Talbourdet, Kristell Lazou, Cecile Viron, Isabelle Renimel, Delphine de Quéral, Robin Kurfurst, Sylvianne Schnebert, Catherine Heusèle, Patrice André, Eric Perrier. In vivo skin antioxidant effect of a new combination based on a specific Vitis vinifera shoot extract and a biotechnological extract. Journal of drugs in dermatology : JDD. 2007 Jun; 6(6 Suppl):s8-13. doi: NULL. [PMID: 17691204]
  • Annarita Poli, Enrico Esposito, Pierangelo Orlando, Licia Lama, Assunta Giordano, Francesca de Appolonia, Barbara Nicolaus, Agata Gambacorta. Halomonas alkaliantarctica sp. nov., isolated from saline lake Cape Russell in Antarctica, an alkalophilic moderately halophilic, exopolysaccharide-producing bacterium. Systematic and applied microbiology. 2007 Jan; 30(1):31-8. doi: 10.1016/j.syapm.2006.03.003. [PMID: 16621401]
  • R E A Moghaieb, N Tanaka, H Saneoka, Y Murooka, H Ono, H Morikawa, A Nakamura, N T Nguyen, R Suwa, K Fujita. Characterization of salt tolerance in ectoine-transformed tobacco plants (Nicotiana tabaccum): photosynthesis, osmotic adjustment, and nitrogen partitioning. Plant, cell & environment. 2006 Feb; 29(2):173-82. doi: 10.1111/j.1365-3040.2005.01410.x. [PMID: 17080633]
  • Carmen Vargas, Aris Kallimanis, Anna I Koukkou, María I Calderon, David Canovas, Fernando Iglesias-Guerra, Constantin Drainas, Antonio Ventosa, Joaquín J Nieto. Contribution of chemical changes in membrane lipids to the osmoadaptation of the halophilic bacterium Chromohalobacter salexigens. Systematic and applied microbiology. 2005 Sep; 28(7):571-81. doi: 10.1016/j.syapm.2005.03.014. [PMID: 16156114]
  • Ralf Steger, Martin Weinand, Reinhard Krämer, Susanne Morbach. LcoP, an osmoregulated betaine/ectoine uptake system from Corynebacterium glutamicum. FEBS letters. 2004 Aug; 573(1-3):155-60. doi: 10.1016/j.febslet.2004.07.067. [PMID: 15327991]
  • Aurélie Baliarda, Hervé Robert, Mohamed Jebbar, Carlos Blanco, Claire Le Marrec. Isolation and characterization of ButA, a secondary glycine betaine transport system operating in Tetragenococcus halophila. Current microbiology. 2003 Oct; 47(4):347-51. doi: 10.1007/s00284-002-4017-x. [PMID: 14629018]
  • Kazuya Yoshida. Plant biotechnology--genetic engineering to enhance plant salt tolerance. Journal of bioscience and bioengineering. 2002; 94(6):585-90. doi: 10.1016/s1389-1723(02)80199-2. [PMID: 16233354]
  • Denis Rontein, Gilles Basset, Andrew D Hanson. Metabolic engineering of osmoprotectant accumulation in plants. Metabolic engineering. 2002 Jan; 4(1):49-56. doi: 10.1006/mben.2001.0208. [PMID: 11800574]
  • I Romano, B Nicolaus, L Lama, D Trabasso, G Caracciolo, A Gambacorta. Accumulation of osmoprotectants and lipid pattern modulation in response to growth conditions by Halomonas pantelleriense. Systematic and applied microbiology. 2001 Nov; 24(3):342-52. doi: 10.1078/0723-2020-00046. [PMID: 11822668]
  • H Nakayama, K Yoshida, H Ono, Y Murooka, A Shinmyo. Ectoine, the compatible solute of Halomonas elongata, confers hyperosmotic tolerance in cultured tobacco cells. Plant physiology. 2000 Apr; 122(4):1239-47. doi: 10.1104/pp.122.4.1239. [PMID: 10759521]