L-3-Hydroxykynurenine (BioDeep_00000014615)

 

Secondary id: BioDeep_00000403077

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds natural product


代谢物信息卡片


(2S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid

化学式: C10H12N2O4 (224.07970319999998)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.02%

分子结构信息

SMILES: c1(c(c(ccc1)C(=O)C[C@H](N)C(=O)O)N)O
InChI: InChI=1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)/t6-/m0/s1

描述信息

L-3-Hydroxykynurenine (L-3-HK) is a metabolite in the kynurenine pathway, the major route of tryptophan degradation in mammals. Kynurenine 3-monooxygenase, an NADPH-dependent flavin monooxygenase, catalyses the hydroxylation of L-kynurenine to L-3-hydroxykynurenine. 3-hydroxykynurenine can be converted to 3-hydroxyanthranilate by the enzyme 3-hydroxykinureninase. It may also be converted to 4-(2-amino-3-hydroxphenyl)-2,4-dioxobutanoate by the enzyme kynurenine-oxoglutarate transaminase. L-3-Hydroxykynurenine (L-3-HK) is a known generator of highly reactive free radicals. An elevation of L-3-HK levels has been shown to constitute a significant hazard in situations of excitotoxic injury. In particular, L-3-HK may contribute to the neuronal deficits underlying HIV-associated dementia (PMID: 7830088). Pharmacological interventions aimed at decreasing L-3-HK formation may therefore be particularly useful for the treatment of neurological diseases which are associated with an abnormally enhanced flux through the kynurenine pathway (PMID: 10583474) [HMDB]
L-3-Hydroxykynurenine (L-3-HK) is a metabolite in the kynurenine pathway, the major route of tryptophan degradation in mammals. Kynurenine 3-monooxygenase, an NADPH-dependent flavin monooxygenase, catalyses the hydroxylation of L-kynurenine to L-3-hydroxykynurenine. 3-hydroxykynurenine can be converted to 3-hydroxyanthranilate by the enzyme 3-hydroxykinureninase. It may also be converted to 4-(2-amino-3-hydroxphenyl)-2,4-dioxobutanoate by the enzyme kynurenine-oxoglutarate transaminase. L-3-Hydroxykynurenine (L-3-HK) is a known generator of highly reactive free radicals. An elevation of L-3-HK levels has been shown to constitute a significant hazard in situations of excitotoxic injury. In particular, L-3-HK may contribute to the neuronal deficits underlying HIV-associated dementia (PMID: 7830088). Pharmacological interventions aimed at decreasing L-3-HK formation may therefore be particularly useful for the treatment of neurological diseases which are associated with an abnormally enhanced flux through the kynurenine pathway (PMID: 10583474).

同义名列表

8 个代谢物同义名

(2S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid; (2S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoate; 3-(2-Amino-3-hydroxybenzoyl)-L-alanine; 3-(3-Hydroxyanthraniloyl)-L-alanine; 3-Hydroxy-L-kynurenine; L-3-Hydroxykynurenine; L-3-HK; 3-Hydroxy-L-kynurenine



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(2)

PlantCyc(0)

代谢反应

65 个相关的代谢反应过程信息。

Reactome(56)

BioCyc(2)

WikiPathways(1)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(5)

PharmGKB(0)

21 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

  • Dénes Zádori, Péter Klivényi, Levente Szalárdy, Ferenc Fülöp, József Toldi, László Vécsei. Mitochondrial disturbances, excitotoxicity, neuroinflammation and kynurenines: novel therapeutic strategies for neurodegenerative disorders. Journal of the neurological sciences. 2012 Nov; 322(1-2):187-91. doi: 10.1016/j.jns.2012.06.004. [PMID: 22749004]
  • Sunoh Kwon, Bombi Lee, Mijung Yeom, Bong-Jun Sur, Myunghwan Kim, Seung-Tae Kim, Hi-Joon Park, Hyejung Lee, Dae-Hyun Hahm. Modulatory effects of acupuncture on murine depression-like behavior following chronic systemic inflammation. Brain research. 2012 Sep; 1472(?):149-60. doi: 10.1016/j.brainres.2012.07.009. [PMID: 22796291]
  • Praveen Kumar Munipally, Satish G Agraharm, Vijay Kumar Valavala, Sridhar Gundae, Naga Raju Turlapati. Evaluation of indoleamine 2,3-dioxygenase expression and kynurenine pathway metabolites levels in serum samples of diabetic retinopathy patients. Archives of physiology and biochemistry. 2011 Dec; 117(5):254-8. doi: 10.3109/13813455.2011.623705. [PMID: 22034910]
  • A M Myint, M J Schwarz, R Verkerk, H H Mueller, J Zach, S Scharpé, H W M Steinbusch, B E Leonard, Y K Kim. Reversal of imbalance between kynurenic acid and 3-hydroxykynurenine by antipsychotics in medication-naïve and medication-free schizophrenic patients. Brain, behavior, and immunity. 2011 Nov; 25(8):1576-81. doi: 10.1016/j.bbi.2011.05.005. [PMID: 21620952]
  • J K Yao, G G Dougherty, R D Reddy, M S Keshavan, D M Montrose, W R Matson, S Rozen, R R Krishnan, J McEvoy, R Kaddurah-Daouk. Altered interactions of tryptophan metabolites in first-episode neuroleptic-naive patients with schizophrenia. Molecular psychiatry. 2010 Sep; 15(9):938-53. doi: 10.1038/mp.2009.33. [PMID: 19401681]
  • Phillip Moheno, John Morrey, Dietmar Fuchs. Effect of dipterinyl calcium pentahydrate on hepatitis B virus replication in transgenic mice. Journal of translational medicine. 2010 Mar; 8(?):32. doi: 10.1186/1479-5876-8-32. [PMID: 20356392]
  • Abdulla A-B Badawy, Christopher J Morgan. Rapid Isocratic Liquid Chromatographic Separation and Quantification of Tryptophan and Six kynurenine Metabolites in Biological Samples with Ultraviolet and Fluorimetric Detection. International journal of tryptophan research : IJTR. 2010; 3(?):175-86. doi: 10.4137/ijtr.s6225. [PMID: 22084598]
  • Yousef A Taher, Benoit J A Piavaux, Reneé Gras, Betty C A M van Esch, Gerard A Hofman, Nanne Bloksma, Paul A J Henricks, Antoon J M van Oosterhout. Indoleamine 2,3-dioxygenase-dependent tryptophan metabolites contribute to tolerance induction during allergen immunotherapy in a mouse model. The Journal of allergy and clinical immunology. 2008 Apr; 121(4):983-91.e2. doi: 10.1016/j.jaci.2007.11.021. [PMID: 18179817]
  • Thijs Kaper, Loren L Looger, Hitomi Takanaga, Michael Platten, Lawrence Steinman, Wolf B Frommer. Nanosensor detection of an immunoregulatory tryptophan influx/kynurenine efflux cycle. PLoS biology. 2007 Oct; 5(10):e257. doi: 10.1371/journal.pbio.0050257. [PMID: 17896864]
  • M Christensen, M Duno, A M Lund, F Skovby, E Christensen. Xanthurenic aciduria due to a mutation in KYNU encoding kynureninase. Journal of inherited metabolic disease. 2007 Apr; 30(2):248-55. doi: 10.1007/s10545-007-0396-2. [PMID: 17334708]
  • Magdalena M Staniszewska, Ram H Nagaraj. 3-hydroxykynurenine-mediated modification of human lens proteins: structure determination of a major modification using a monoclonal antibody. The Journal of biological chemistry. 2005 Jun; 280(23):22154-64. doi: 10.1074/jbc.m501419200. [PMID: 15817458]
  • Wei Wang, Bin Qiu, Xueqin Xu, Lan Zhang, Guonan Chen. Separation and determination of L-tryptophan and its metabolites by capillary micellar electrokinetic chromatography with amperometric detection. Electrophoresis. 2005 Feb; 26(4-5):903-910. doi: 10.1002/elps.200406099. [PMID: 15714546]
  • C M Forrest, G M Mackay, N Stoy, M Egerton, J Christofides, T W Stone, L G Darlington. Tryptophan loading induces oxidative stress. Free radical research. 2004 Nov; 38(11):1167-71. doi: 10.1080/10715760400011437. [PMID: 15621693]
  • T J Greer Wilson, Karl Kristian Thomsen, Bent O Petersen, Jens Ø Duus, Richard P Oliver. Detection of 3-hydroxykynurenine in a plant pathogenic fungus. The Biochemical journal. 2003 May; 371(Pt 3):783-8. doi: 10.1042/bj20021797. [PMID: 12556224]
  • Caroline M Forrest, Alan Kennedy, Trevor W Stone, Nicholas Stoy, L Gail Darlington. Kynurenine and neopterin levels in patients with rheumatoid arthritis and osteoporosis during drug treatment. Advances in experimental medicine and biology. 2003; 527(?):287-95. doi: 10.1007/978-1-4615-0135-0_32. [PMID: 15206742]
  • Dariusz Pawlak, Mariusz Koda, Sawomir Wołczyński, Michal Myśliwiec, Wlodzimierz Buczko. Mechanism of inhibitory effect of 3-hydroxykynurenine on erythropoiesis in patients with renal insufficiency. Advances in experimental medicine and biology. 2003; 527(?):375-80. doi: 10.1007/978-1-4615-0135-0_43. [PMID: 15206753]
  • H Z Malina, C Richter, M Mehl, O M Hess. Pathological apoptosis by xanthurenic acid, a tryptophan metabolite: activation of cell caspases but not cytoskeleton breakdown. BMC physiology. 2001; 1(?):7. doi: 10.1186/1472-6793-1-7. [PMID: 11459518]