Norvaline (BioDeep_00000003157)

 

Secondary id: BioDeep_00000178471, BioDeep_00000614854, BioDeep_00001868695, BioDeep_00001871968

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


alpha -DL-Aminopentanoic acid

化学式: C5H11NO2 (117.0789746)
中文名称: 戊氨酸, D-正缬氨酸, DL-正缬氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 11.31%

Reviewed

Last reviewed on 2024-07-29.

Cite this Page

Norvaline. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/norvaline (retrieved 2024-11-28) (BioDeep RN: BioDeep_00000003157). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCC(C(=O)O)N
InChI: InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

描述信息

Norvaline is a non-proteinogenic branched-chain amino acid with the chemical formula C5H11NO2, isomeric with valine. It has previously been reported to be a natural component of an antifungal peptide of Bacillus subtilis. Norvaline and other modified branched chain amino acids have received attention in recent studies, as they appear to be incorporated in some recombinant proteins found in E. coli. This amino acid is often made synthetically.
DL-Norvaline, a derivative of L-norvaline, L-norvaline is a non-competitive inhibitor of arginase.
DL-Norvaline, a derivative of L-norvaline, L-norvaline is a non-competitive inhibitor of arginase.

同义名列表

32 个代谢物同义名

alpha -DL-Aminopentanoic acid; DL-alpha-Amino-N-valenic acid; alpha-DL-Aminopentanoic acid; DL-alpha -Aminovaleric acid; (2R)-2-aminopentanoic acid; DL-alpha-Aminovaleric acid; alpha-Aminopentanoic acid; Norvaline (acd/name 4.0); DL-2-Aminopentanoic acid; alpha-Aminovaleric acid; D-2-Aminopentanoic acid; 2-Amino-DL-valeric acid; 2-Aminopentanoic acids; D-2-Aminovaleric acid; 2-Aminovaleric acids; 2-Aminovaleric acid; D-2-Aminopentanoate; (.+/-.)-norvaline; D-2-Aminovalerate; (.+-.)-norvaline; D-(-)-norvaline; D(-)-Norvaline; (R)-Norvaline; DL-NORVALINE; D-Norvaline; Norvalines; Norvaline; D-Nva; D-Ape; Norvaline; 2-Aminopentanoic acid; DL-Norvaline



数据库引用编号

17 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)

18 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

  • Hayarpi Javrushyan, Edita Nadiryan, Anna Grigoryan, Nikolay Avtandilyan, Alina Maloyan. Antihyperglycemic activity of L-norvaline and L-arginine in high-fat diet and streptozotocin-treated male rats. Experimental and molecular pathology. 2022 06; 126(?):104763. doi: 10.1016/j.yexmp.2022.104763. [PMID: 35398371]
  • Michael A Gilinsky, Yulia K Polityko, Arkady L Markel, Tatyana V Latysheva, Abraham O Samson, Baruh Polis, Sergey E Naumenko. Norvaline Reduces Blood Pressure and Induces Diuresis in Rats with Inherited Stress-Induced Arterial Hypertension. BioMed research international. 2020; 2020(?):4935386. doi: 10.1155/2020/4935386. [PMID: 32149110]
  • Abhijit De, Mamta F Singh, Vinod Singh, Veerma Ram, Shradha Bisht. Treatment effect of l-Norvaline on the sexual performance of male rats with streptozotocin induced diabetes. European journal of pharmacology. 2016 Jan; 771(?):247-54. doi: 10.1016/j.ejphar.2015.12.008. [PMID: 26671005]
  • A P Lytvynenko, T Yu Voznesenska, R I Yanchiy. [THE ROLE OF NO AND MEXIDOL IN CONTRACTILITY OF OVARIAN AND CERVICAL PARTS OF UTERUS UNDER THE CONDITION OF IMMUNE-MEDIATED INJURY IN MICE]. Fiziolohichnyi zhurnal (Kiev, Ukraine : 1994). 2015; 61(5):52-6. doi: 10.15407/fz61.05.052. [PMID: 26845844]
  • Hany M El-Bassossy, Rania El-Fawal, Ahmed Fahmy, Malcolm L Watson. Arginase inhibition alleviates hypertension in the metabolic syndrome. British journal of pharmacology. 2013 Jun; 169(3):693-703. doi: 10.1111/bph.12144. [PMID: 23441715]
  • Hany M El-Bassossy, Rania El-Fawal, Ahmed Fahmy. Arginase inhibition alleviates hypertension associated with diabetes: effect on endothelial dependent relaxation and NO production. Vascular pharmacology. 2012 Nov; 57(5-6):194-200. doi: 10.1016/j.vph.2012.01.001. [PMID: 22281732]
  • Hank Greenway, Konstantin Y Kulichikhin, Gregory R Cawthray, Timothy D Colmer. pH regulation in anoxic rice coleoptiles at pH 3.5: biochemical pHstats and net H+ influx in the absence and presence of NOFormula. Journal of experimental botany. 2012 Mar; 63(5):1969-83. doi: 10.1093/jxb/err395. [PMID: 22174442]
  • Laura A Onyango, R Hugh Dunstan, Johan Gottfries, Christof von Eiff, Timothy K Roberts. Effect of low temperature on growth and ultra-structure of Staphylococcus spp. PloS one. 2012; 7(1):e29031. doi: 10.1371/journal.pone.0029031. [PMID: 22291884]
  • Désirée van Noord, Peter B F Mensink, Robert J de Knegt, Martine Ouwendijk, Jan Francke, Anneke J van Vuuren, Bettina E Hansen, Ernst J Kuipers. Serum markers and intestinal mucosal injury in chronic gastrointestinal ischemia. Digestive diseases and sciences. 2011 Feb; 56(2):506-12. doi: 10.1007/s10620-010-1303-5. [PMID: 20628816]
  • Wagner L Araújo, Adriano Nunes-Nesi, Sonia Osorio, Björn Usadel, Daniela Fuentes, Réka Nagy, Ilse Balbo, Martin Lehmann, Claudia Studart-Witkowski, Takayuki Tohge, Enrico Martinoia, Xavier Jordana, Fábio M Damatta, Alisdair R Fernie. Antisense inhibition of the iron-sulphur subunit of succinate dehydrogenase enhances photosynthesis and growth in tomato via an organic acid-mediated effect on stomatal aperture. The Plant cell. 2011 Feb; 23(2):600-27. doi: 10.1105/tpc.110.081224. [PMID: 21307286]
  • Jan-Willem de Kraker, Jonathan Gershenzon. From amino acid to glucosinolate biosynthesis: protein sequence changes in the evolution of methylthioalkylmalate synthase in Arabidopsis. The Plant cell. 2011 Jan; 23(1):38-53. doi: 10.1105/tpc.110.079269. [PMID: 21205930]
  • Ripu M Kunwar, Keshab P Shrestha, Rainer W Bussmann. Traditional herbal medicine in far-west Nepal: a pharmacological appraisal. Journal of ethnobiology and ethnomedicine. 2010 Dec; 6(?):35. doi: 10.1186/1746-4269-6-35. [PMID: 21144003]
  • Katja Arand, David Stock, Markus Burghardt, Markus Riederer. pH-dependent permeation of amino acids through isolated ivy cuticles is affected by cuticular water sorption and hydration shell size of the solute. Journal of experimental botany. 2010 Sep; 61(14):3865-73. doi: 10.1093/jxb/erq193. [PMID: 20631051]
  • Ian R Lanza, Shucha Zhang, Lawrence E Ward, Helen Karakelides, Daniel Raftery, K Sreekumaran Nair. Quantitative metabolomics by H-NMR and LC-MS/MS confirms altered metabolic pathways in diabetes. PloS one. 2010 May; 5(5):e10538. doi: 10.1371/journal.pone.0010538. [PMID: 20479934]
  • Piyun Chao, Manjeet Deshmukh, Hilliard L Kutscher, Dayuan Gao, Sujata Sundara Rajan, Peidi Hu, Debra L Laskin, Stanley Stein, Patrick J Sinko. Pulmonary targeting microparticulate camptothecin delivery system: anticancer evaluation in a rat orthotopic lung cancer model. Anti-cancer drugs. 2010 Jan; 21(1):65-76. doi: 10.1097/cad.0b013e328332a322. [PMID: 19966540]
  • Lee D Roberts, David G Hassall, Deborah A Winegar, John N Haselden, Andrew W Nicholls, Julian L Griffin. Increased hepatic oxidative metabolism distinguishes the action of Peroxisome proliferator-activated receptor delta from Peroxisome proliferator-activated receptor gamma in the ob/ob mouse. Genome medicine. 2009 Dec; 1(12):115. doi: 10.1186/gm115. [PMID: 19968882]
  • L A W Jans, C K J Lieben, L T Smits, A Blokland. Pharmacokinetics of acute tryptophan depletion using a gelatin-based protein in male and female Wistar rats. Amino acids. 2009 Jul; 37(2):349-57. doi: 10.1007/s00726-008-0160-4. [PMID: 18683016]
  • William J Zinnanti, Jelena Lazovic, Kathleen Griffin, Kristen J Skvorak, Harbhajan S Paul, Gregg E Homanics, Maria C Bewley, Keith C Cheng, Kathryn F Lanoue, John M Flanagan. Dual mechanism of brain injury and novel treatment strategy in maple syrup urine disease. Brain : a journal of neurology. 2009 Apr; 132(Pt 4):903-18. doi: 10.1093/brain/awp024. [PMID: 19293241]
  • A A-B Badawy, C J Morgan, J A Turner. Application of the Phenomenex EZ:faasttrade mark amino acid analysis kit for rapid gas-chromatographic determination of concentrations of plasma tryptophan and its brain uptake competitors. Amino acids. 2008 May; 34(4):587-96. doi: 10.1007/s00726-007-0012-7. [PMID: 18071842]
  • Jonathan R Howarth, Saroj Parmar, Janina Jones, Caroline E Shepherd, Delia-Irina Corol, Aimee M Galster, Nathan D Hawkins, Sonia J Miller, John M Baker, Paul J Verrier, Jane L Ward, Michael H Beale, Peter B Barraclough, Malcolm J Hawkesford. Co-ordinated expression of amino acid metabolism in response to N and S deficiency during wheat grain filling. Journal of experimental botany. 2008; 59(13):3675-89. doi: 10.1093/jxb/ern218. [PMID: 18791197]
  • K Rutten, C Lieben, L Smits, A Blokland. The PDE4 inhibitor rolipram reverses object memory impairment induced by acute tryptophan depletion in the rat. Psychopharmacology. 2007 Jun; 192(2):275-82. doi: 10.1007/s00213-006-0697-4. [PMID: 17265077]
  • T A C Vermeij, P M Edelbroek. Simultaneous high-performance liquid chromatographic analysis of pregabalin, gabapentin and vigabatrin in human serum by precolumn derivatization with o-phtaldialdehyde and fluorescence detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Oct; 810(2):297-303. doi: 10.1016/j.jchromb.2004.08.018. [PMID: 15380728]
  • Naohito Ishii, Hideki Ikenaga, Pamela K Carmines, Yoshikazu Aoki, Zensuke Ogawa, Takao Saruta, Tetsuya Suga. High glucose augments arginase activity and nitric oxide production in the renal cortex. Metabolism: clinical and experimental. 2004 Jul; 53(7):868-74. doi: 10.1016/j.metabol.2004.02.011. [PMID: 15254879]
  • Y Yamada, T Hamaguchi, M Goto, K Muro, Y Matsumura, Y Shimada, K Shirao, S Nagayama. Plasma concentrations of 5-fluorouracil and F-beta-alanine following oral administration of S-1, a dihydropyrimidine dehydrogenase inhibitory fluoropyrimidine, as compared with protracted venous infusion of 5-fluorouracil. British journal of cancer. 2003 Sep; 89(5):816-20. doi: 10.1038/sj.bjc.6601224. [PMID: 12942110]
  • Ratul Saikia, Tanuja Singh, Rakesh Kumar, Juhi Srivastava, Alok K Srivastava, Kiran Singh, Dilip K Arora. Role of salicylic acid in systemic resistance induced by Pseudomonas fluorescens against Fusarium oxysporum f. sp. ciceri in chickpea. Microbiological research. 2003; 158(3):203-13. doi: 10.1078/0944-5013-00202. [PMID: 14521230]
  • Y Abe, S Fukui, Y Koshiji, M Kobayashi, T Shoji, S Sugata, H Nishizawa, H Suzuki, K Iwata. Enantioselective binding sites on bovine serum albumin to dansyl amino acids. Biochimica et biophysica acta. 1999 Aug; 1433(1-2):188-97. doi: 10.1016/s0167-4838(99)00135-1. [PMID: 10446371]
  • E Peyrin, Y C Guillaume, N Morin, C Guinchard. Retention behavior of D,L-dansyl-amino acids on a human serum albumin chiral stationary phase: effect of a mobile phase modifier. Journal of chromatography. A. 1998 May; 808(1-2):113-20. doi: 10.1016/s0021-9673(98)00117-4. [PMID: 9652113]
  • B Picur, M Lisowski, H Taniuchi, E Poerio. Comparison of thermodynamic and kinetic effects between the Leu32-->norvaline and Leu35-->norvaline substitutions of the three-fragment complex of cytochrome c. Archives of biochemistry and biophysics. 1994 Dec; 315(2):533-47. doi: 10.1006/abbi.1994.1534. [PMID: 7986101]
  • M Arslan, C R Pohl, M S Smith, T M Plant. Studies of the role of the N-methyl-D-aspartate (NMDA) receptor in the hypothalamic control of prolactin secretion. Life sciences. 1992; 50(4):295-300. doi: 10.1016/0024-3205(92)90337-o. [PMID: 1531081]
  • H Angliker, P Wikström, E Shaw. Pseudoarginine: synthesis and properties of derivatives of delta-(1-imidazolyl)norvaline. The Biochemical journal. 1990 Mar; 266(3):829-34. doi: . [PMID: 2327968]
  • J K Tews, A E Harper. Tissue amino acids in rats fed norleucine, norvaline, homoarginine or other amino acid analogues. The Journal of nutrition. 1986 Aug; 116(8):1464-72. doi: 10.1093/jn/116.8.1464. [PMID: 2428957]
  • M E Fico, T Motyl, J A Milner. Species comparison of the influence of ammonia on orotic acid and urea biosynthesis in liver. The Journal of nutrition. 1984 Mar; 114(3):613-21. doi: 10.1093/jn/114.3.613. [PMID: 6699742]
  • K Aoyagi, S Ohba, M Narita, S Tojo. Regulation of biosynthesis of guanidinosuccinic acid in isolated rat hepatocytes and in vivo. Kidney international. Supplement. 1983 Dec; 16(?):S224-8. doi: . [PMID: 6588254]