3-Hydroxyanthranilic acid (BioDeep_00000405445)

Main id: BioDeep_00000001233

 

PANOMIX_OTCML-2023


代谢物信息卡片


3-Hydroxyanthranilic acid

化学式: C7H7NO3 (153.0425912)
中文名称: 3-羟基-2-氨基苯甲酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.02%

分子结构信息

SMILES: C1=CC(=C(C(=C1)O)N)C(=O)O
InChI: InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)

描述信息

An aminobenzoic acid that is benzoic acid substituted at C-2 by an amine group and at C-3 by a hydroxy group. It is an intermediate in the metabolism of the amino acid tryptophan.
D000975 - Antioxidants > D016166 - Free Radical Scavengers
D020011 - Protective Agents > D000975 - Antioxidants
MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; WJXSWCUQABXPFS-UHFFFAOYSA-N_STSL_0003_3-hydroxyanthranillic acid_8000fmol_180416_S2_LC02_MS02_37; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I.
MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I.
3-Hydroxyanthranilic acid is a tryptophan metabolite in the kynurenine pathway.

同义名列表

1 个代谢物同义名

3-Hydroxyanthranilic acid



数据库引用编号

49 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

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)

11 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

  • Yan-Kun Zhang, Bing-Kun Yang, Chun-Nuan Zhang, Shi-Xiao Xu, Ping Sun. Effects of polystyrene microplastics acute exposure in the liver of swordtail fish (Xiphophorus helleri) revealed by LC-MS metabolomics. The Science of the total environment. 2022 Dec; 850(?):157772. doi: 10.1016/j.scitotenv.2022.157772. [PMID: 35934030]
  • Lihui Guo, Bernadette Schurink, Eva Roos, Esther J Nossent, Jan Willem Duitman, Alexander Pj Vlaar, Paul van der Valk, Frédéric M Vaz, Syun-Ru Yeh, Zachary Geeraerts, Annemiek Dijkhuis, Lonneke van Vught, Marianna Bugiani, René Lutter. Indoleamine 2,3-dioxygenase (IDO)-1 and IDO-2 activity and severe course of COVID-19. The Journal of pathology. 2022 03; 256(3):256-261. doi: 10.1002/path.5842. [PMID: 34859884]
  • Lieke Bakker, Inez H G B Ramakers, Martin P J van Boxtel, Miranda T Schram, Coen D A Stehouwer, Carla J H van der Kallen, Pieter C Dagnelie, Marleen M J van Greevenbroek, Anke Wesselius, Øivind Midttun, Per M Ueland, Frans R J Verhey, Simone J P M Eussen, Sebastian Köhler. Associations between plasma kynurenines and cognitive function in individuals with normal glucose metabolism, prediabetes and type 2 diabetes: the Maastricht Study. Diabetologia. 2021 11; 64(11):2445-2457. doi: 10.1007/s00125-021-05521-4. [PMID: 34409496]
  • Guangzheng Zhang, Zhenyuan Lang, Qifan Yang, You Nie, Zhihan Wang, Ming Gao, Nan Zhang, Xia Xu. UPLC-Q-TOF/MS-based plasma metabolome to identify biomarkers and time of injury in traumatic brain injured rats. Neuroreport. 2021 04; 32(6):415-422. doi: 10.1097/wnr.0000000000001576. [PMID: 33788810]
  • M Karayama, J Masuda, K Mori, H Yasui, H Hozumi, Y Suzuki, K Furuhashi, T Fujisawa, N Enomoto, Y Nakamura, N Inui, T Suda, M Maekawa, H Sugimura, A Takada. Comprehensive assessment of multiple tryptophan metabolites as potential biomarkers for immune checkpoint inhibitors in patients with non-small cell lung cancer. Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico. 2021 Feb; 23(2):418-423. doi: 10.1007/s12094-020-02421-8. [PMID: 32533317]
  • Martin Berg, Konstantinos A Polyzos, Hanna Agardh, Roland Baumgartner, Maria J Forteza, Ilona Kareinen, Anton Gisterå, Gerhard Bottcher, Eva Hurt-Camejo, Göran K Hansson, Daniel F J Ketelhuth. 3-Hydroxyanthralinic acid metabolism controls the hepatic SREBP/lipoprotein axis, inhibits inflammasome activation in macrophages, and decreases atherosclerosis in Ldlr-/- mice. Cardiovascular research. 2020 10; 116(12):1948-1957. doi: 10.1093/cvr/cvz258. [PMID: 31589306]
  • Masashi Sakurai, Yasuko Yamamoto, Noriyo Kanayama, Masaya Hasegawa, Akihiro Mouri, Masao Takemura, Hidetoshi Matsunami, Tomoya Miyauchi, Tatsuya Tokura, Hiroyuki Kimura, Mikiko Ito, Eri Umemura, Aiji Sato Boku, Wataru Nagashima, Takashi Tonoike, Kenichi Kurita, Norio Ozaki, Toshitaka Nabeshima, Kuniaki Saito. Serum Metabolic Profiles of the Tryptophan-Kynurenine Pathway in the high risk subjects of major depressive disorder. Scientific reports. 2020 02; 10(1):1961. doi: 10.1038/s41598-020-58806-w. [PMID: 32029791]
  • Romain Colle, Perrine Masson, Céline Verstuyft, Bruno Fève, Erwan Werner, Claire Boursier-Neyret, Bernard Walther, Denis J David, Bruno Boniface, Bruno Falissard, Philippe Chanson, Emmanuelle Corruble, Laurent Becquemont. Peripheral tryptophan, serotonin, kynurenine, and their metabolites in major depression: A case-control study. Psychiatry and clinical neurosciences. 2020 Feb; 74(2):112-117. doi: 10.1111/pcn.12944. [PMID: 31599111]
  • Karen M Ryan, Kelly A Allers, Declan M McLoughlin, Andrew Harkin. Tryptophan metabolite concentrations in depressed patients before and after electroconvulsive therapy. Brain, behavior, and immunity. 2020 01; 83(?):153-162. doi: 10.1016/j.bbi.2019.10.005. [PMID: 31606477]
  • Yun Chen, Hui Chen, Ganggang Shi, Min Yang, Fuchun Zheng, Zhijie Zheng, Shuyao Zhang, Shilong Zhong. Ultra-performance liquid chromatography-tandem mass spectrometry quantitative profiling of tryptophan metabolites in human plasma and its application to clinical study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Oct; 1128(?):121745. doi: 10.1016/j.jchromb.2019.121745. [PMID: 31586884]
  • Katsumi Shibata. Organ Co-Relationship in Tryptophan Metabolism and Factors That Govern the Biosynthesis of Nicotinamide from Tryptophan. Journal of nutritional science and vitaminology. 2018; 64(2):90-98. doi: 10.3177/jnsv.64.90. [PMID: 29710037]
  • Joyce Y Huang, Lesley M Butler, Øivind Midttun, Arve Ulvik, Renwei Wang, Aizhen Jin, Yu-Tang Gao, Per M Ueland, Woon-Puay Koh, Jian-Min Yuan. A prospective evaluation of serum kynurenine metabolites and risk of pancreatic cancer. PloS one. 2018; 13(5):e0196465. doi: 10.1371/journal.pone.0196465. [PMID: 29734388]
  • Qiongxin Wang, Ye Ding, Ping Song, Huaiping Zhu, Imoh Okon, Yang-Nan Ding, Hou-Zao Chen, De-Pei Liu, Ming-Hui Zou. Tryptophan-Derived 3-Hydroxyanthranilic Acid Contributes to Angiotensin II-Induced Abdominal Aortic Aneurysm Formation in Mice In Vivo. Circulation. 2017 Dec; 136(23):2271-2283. doi: 10.1161/circulationaha.117.030972. [PMID: 28978552]
  • Therese Karlsson, Elin Strand, Jutta Dierkes, Christian A Drevon, Jannike Øyen, Øivind Midttun, Per M Ueland, Oddrun A Gudbrandsen, Eva Ringdal Pedersen, Ottar Nygård. Associations between intake of fish and n-3 long-chain polyunsaturated fatty acids and plasma metabolites related to the kynurenine pathway in patients with coronary artery disease. European journal of nutrition. 2017 Feb; 56(1):261-272. doi: 10.1007/s00394-015-1077-9. [PMID: 26482150]
  • Lasse Melvaer Giil, Øivind Midttun, Helga Refsum, Arve Ulvik, Rajiv Advani, A David Smith, Per Magne Ueland. Kynurenine Pathway Metabolites in Alzheimer's Disease. Journal of Alzheimer's disease : JAD. 2017; 60(2):495-504. doi: 10.3233/jad-170485. [PMID: 28869479]
  • Oana M Deac, James L Mills, Clair M Gardiner, Barry Shane, Louise Quinn, Øivind Midttun, Adrian McCann, Klaus Meyer, Per M Ueland, Ruzong Fan, Zhaohui Lu, Lawrence C Brody, Anne M Molloy. Serum Immune System Biomarkers Neopterin and Interleukin-10 Are Strongly Related to Tryptophan Metabolism in Healthy Young Adults. The Journal of nutrition. 2016 09; 146(9):1801-6. doi: 10.3945/jn.116.230698. [PMID: 27489009]
  • Abdulla A-B Badawy, Samina Bano. Elevation of Kynurenine Metabolites in Rat Liver and Serum: A Potential Additional Mechanism of the Alcohol Aversive and Anti-cancer Effects of Disulfiram?. Alcohol and alcoholism (Oxford, Oxfordshire). 2016 Jan; 51(1):20-6. doi: 10.1093/alcalc/agv085. [PMID: 26224731]
  • Gregory F Oxenkrug. Increased Plasma Levels of Xanthurenic and Kynurenic Acids in Type 2 Diabetes. Molecular neurobiology. 2015 Oct; 52(2):805-10. doi: 10.1007/s12035-015-9232-0. [PMID: 26055228]
  • Fang Tao Xie, Ji Sen Cao, Jian Zhao, Yang Yu, Feng Qi, Xiang Chen Dai. IDO expressing dendritic cells suppress allograft rejection of small bowel transplantation in mice by expansion of Foxp3+ regulatory T cells. Transplant immunology. 2015 Oct; 33(2):69-77. doi: 10.1016/j.trim.2015.05.003. [PMID: 26002283]
  • J Reyes-Ocampo, D Ramírez-Ortega, G I Vázquez Cervantes, B Pineda, Pavel Montes de Oca Balderas, D González-Esquivel, L Sánchez-Chapul, R Lugo-Huitrón, D Silva-Adaya, C Ríos, A Jiménez-Anguiano, V Pérez-de la Cruz. Mitochondrial dysfunction related to cell damage induced by 3-hydroxykynurenine and 3-hydroxyanthranilic acid: Non-dependent-effect of early reactive oxygen species production. Neurotoxicology. 2015 Sep; 50(?):81-91. doi: 10.1016/j.neuro.2015.08.003. [PMID: 26254737]
  • Luisa Rios-Avila, Bonnie Coats, Maria Ralat, Yueh-Yun Chi, Øivind Midttun, Per M Ueland, Peter W Stacpoole, Jesse F Gregory. Pyridoxine supplementation does not alter in vivo kinetics of one-carbon metabolism but modifies patterns of one-carbon and tryptophan metabolites in vitamin B-6-insufficient oral contraceptive users. The American journal of clinical nutrition. 2015 Sep; 102(3):616-25. doi: 10.3945/ajcn.115.113159. [PMID: 26201817]
  • Chun-Yueh Huang, Danny O'Hare, I-Jen Chao, Hung-Wei Wei, Yi-Fan Liang, Bin-Da Liu, Mei-Hwa Lee, Hung-Yin Lin. Integrated potentiostat for electrochemical sensing of urinary 3-hydroxyanthranilic acid with molecularly imprinted poly(ethylene-co-vinyl alcohol). Biosensors & bioelectronics. 2015 May; 67(?):208-13. doi: 10.1016/j.bios.2014.08.018. [PMID: 25175746]
  • Oana M Deac, James L Mills, Barry Shane, Øivind Midttun, Per M Ueland, John T Brosnan, Margaret E Brosnan, Eamon Laird, Eileen R Gibney, Ruzong Fan, Yifan Wang, Lawrence C Brody, Anne M Molloy. Tryptophan catabolism and vitamin B-6 status are affected by gender and lifestyle factors in healthy young adults. The Journal of nutrition. 2015 Apr; 145(4):701-7. doi: 10.3945/jn.114.203091. [PMID: 25833774]
  • Giuseppe Ristagno, Roberto Latini, Jukka Vaahersalo, Serge Masson, Jouni Kurola, Tero Varpula, Jacopo Lucchetti, Claudia Fracasso, Giovanna Guiso, Alessandro Montanelli, Simona Barlera, Marco Gobbi, Marjaana Tiainen, Ville Pettilä, Markus B Skrifvars. Early activation of the kynurenine pathway predicts early death and long-term outcome in patients resuscitated from out-of-hospital cardiac arrest. Journal of the American Heart Association. 2014 Aug; 3(4):. doi: 10.1161/jaha.114.001094. [PMID: 25092787]
  • Weiping Hou, Gang Huang, Xuejiao Cao, Yuanyuan Zhang, Jinbo Zhang, Yan Li. Suppression of experimental autoimmune glomerulonephritis by tryptophan. Journal of nephrology. 2014 Feb; 27(1):19-28. doi: 10.1007/s40620-013-0020-5. [PMID: 24519862]
  • Katsumi Shibata, Tomoaki Ohno, Mitsue Sano, Tsutomu Fukuwatari. The urinary ratio of 3-hydroxykynurenine/3-hydroxyanthranilic acid is an index to predicting the adverse effects of D-tryptophan in rats. Journal of nutritional science and vitaminology. 2014; 60(4):261-8. doi: 10.3177/jnsv.60.261. [PMID: 25297615]
  • Arve Ulvik, Despoina Theofylaktopoulou, Øivind Midttun, Ottar Nygård, Simone J P M Eussen, Per M Ueland. Substrate product ratios of enzymes in the kynurenine pathway measured in plasma as indicators of functional vitamin B-6 status. The American journal of clinical nutrition. 2013 Oct; 98(4):934-40. doi: 10.3945/ajcn.113.064998. [PMID: 24004893]
  • Miki Terakata, Tsutomu Fukuwatari, Eri Kadota, Mitsue Sano, Masaaki Kanai, Toshikazu Nakamura, Hiroshi Funakoshi, Katsumi Shibata. The niacin required for optimum growth can be synthesized from L-tryptophan in growing mice lacking tryptophan-2,3-dioxygenase. The Journal of nutrition. 2013 Jul; 143(7):1046-51. doi: 10.3945/jn.113.176875. [PMID: 23700344]
  • D Theofylaktopoulou, Ø Midttun, A Ulvik, P M Ueland, G S Tell, S E Vollset, O Nygård, S J P M Eussen. A community-based study on determinants of circulating markers of cellular immune activation and kynurenines: the Hordaland Health Study. Clinical and experimental immunology. 2013 Jul; 173(1):121-30. doi: 10.1111/cei.12092. [PMID: 23607723]
  • Katsumi Shibata, Rina Kondo, Mitsue Sano, Tsutomu Fukuwatari. Increased conversion of tryptophan to nicotinamide in rats by dietary valproate. Bioscience, biotechnology, and biochemistry. 2013; 77(2):295-300. doi: 10.1271/bbb.120716. [PMID: 23391917]
  • Martina M Hughes, Angela Carballedo, Declan M McLoughlin, Francesco Amico, Andrew Harkin, Thomas Frodl, Thomas J Connor. Tryptophan depletion in depressed patients occurs independent of kynurenine pathway activation. Brain, behavior, and immunity. 2012 Aug; 26(6):979-87. doi: 10.1016/j.bbi.2012.05.010. [PMID: 22683764]
  • Lei Zhang, Olga Ovchinnikova, Andreas Jönsson, Anna M Lundberg, Martin Berg, Göran K Hansson, Daniel F J Ketelhuth. The tryptophan metabolite 3-hydroxyanthranilic acid lowers plasma lipids and decreases atherosclerosis in hypercholesterolaemic mice. European heart journal. 2012 Aug; 33(16):2025-34. doi: 10.1093/eurheartj/ehs175. [PMID: 22711758]
  • Svetlana Dolina, Dov Margalit, Sergey Malitsky, Eugeny Pressman, Aharon Rabinkov. Epilepsy as a pyridoxine-dependent condition: quantified urinary biomarkers for status evaluation and monitoring antiepileptic treatment. Medical hypotheses. 2012 Aug; 79(2):157-64. doi: 10.1016/j.mehy.2012.04.022. [PMID: 22647618]
  • Marisa Möller, Jan L Du Preez, Robin Emsley, Brian H Harvey. Social isolation rearing in rats alters plasma tryptophan metabolism and is reversed by sub-chronic clozapine treatment. Neuropharmacology. 2012 Jun; 62(8):2499-506. doi: 10.1016/j.neuropharm.2012.02.021. [PMID: 22426240]
  • Marisa Möller, Jan L Du Preez, Brian H Harvey. Development and validation of a single analytical method for the determination of tryptophan, and its kynurenine metabolites in rat plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jun; 898(?):121-9. doi: 10.1016/j.jchromb.2012.04.030. [PMID: 22608808]
  • Gopi S Gadupudi, King-Thom Chung. Comparative genotoxicity of 3-hydroxyanthranilic acid and anthranilic acid in the presence of a metal cofactor Cu (II) in vitro. Mutation research. 2011 Dec; 726(2):200-8. doi: 10.1016/j.mrgentox.2011.09.012. [PMID: 22015263]
  • Caroline M Forrest, Gillian M Mackay, Lynn Oxford, Keith Millar, L Gail Darlington, Michael J Higgins, Trevor W Stone. Kynurenine metabolism predicts cognitive function in patients following cardiac bypass and thoracic surgery. Journal of neurochemistry. 2011 Oct; 119(1):136-52. doi: 10.1111/j.1471-4159.2011.07414.x. [PMID: 21819405]
  • Ursula Kües, Martin Rühl. Multiple multi-copper oxidase gene families in basidiomycetes - what for?. Current genomics. 2011 Apr; 12(2):72-94. doi: 10.2174/138920211795564377. [PMID: 21966246]
  • Hee Jung Ahn, Kyung Wan Min, Youn-Ok Cho. Assessment of vitamin B(6) status in Korean patients with newly diagnosed type 2 diabetes. Nutrition research and practice. 2011 Feb; 5(1):34-9. doi: 10.4162/nrp.2011.5.1.34. [PMID: 21487494]
  • Christabelle J Darcy, Joshua S Davis, Tonia Woodberry, Yvette R McNeil, Dianne P Stephens, Tsin W Yeo, Nicholas M Anstey. An observational cohort study of the kynurenine to tryptophan ratio in sepsis: association with impaired immune and microvascular function. PloS one. 2011; 6(6):e21185. doi: 10.1371/journal.pone.0021185. [PMID: 21731667]
  • 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]
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  • Krystyna Pawlak, Anna Kowalewska, Michal Mysliwiec, Dariusz Pawlak. 3-hydroxyanthranilic acid is independently associated with monocyte chemoattractant protein-1 (CCL2) and macrophage inflammatory protein-1beta (CCL4) in patients with chronic kidney disease. Clinical biochemistry. 2010 Sep; 43(13-14):1101-6. doi: 10.1016/j.clinbiochem.2010.06.008. [PMID: 20599874]
  • Raf Brouns, Robert Verkerk, Tony Aerts, Didier De Surgeloose, Annick Wauters, Simon Scharpé, Peter P De Deyn. The role of tryptophan catabolism along the kynurenine pathway in acute ischemic stroke. Neurochemical research. 2010 Sep; 35(9):1315-22. doi: 10.1007/s11064-010-0187-2. [PMID: 20490917]
  • David Favre, Jeff Mold, Peter W Hunt, Bittoo Kanwar, P'ng Loke, Lillian Seu, Jason D Barbour, Margaret M Lowe, Anura Jayawardene, Francesca Aweeka, Yong Huang, Daniel C Douek, Jason M Brenchley, Jeffrey N Martin, Frederick M Hecht, Steven G Deeks, Joseph M McCune. Tryptophan catabolism by indoleamine 2,3-dioxygenase 1 alters the balance of TH17 to regulatory T cells in HIV disease. Science translational medicine. 2010 May; 2(32):32ra36. doi: 10.1126/scitranslmed.3000632. [PMID: 20484731]
  • Andrea Moglia, Cinzia Comino, Sergio Lanteri, Ric de Vos, Pieter de Waard, Teris A van Beek, Luca Goitre, Saverio Francesco Retta, Jules Beekwilder. Production of novel antioxidative phenolic amides through heterologous expression of the plant's chlorogenic acid biosynthesis genes in yeast. Metabolic engineering. 2010 May; 12(3):223-32. doi: 10.1016/j.ymben.2009.11.003. [PMID: 19941969]
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  • 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]
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  • Caroline M Forrest, Gillian M Mackay, Lynn Oxford, Nicholas Stoy, Trevor W Stone, L Gail Darlington. Kynurenine pathway metabolism in patients with osteoporosis after 2 years of drug treatment. Clinical and experimental pharmacology & physiology. 2006 Nov; 33(11):1078-87. doi: 10.1111/j.1440-1681.2006.04490.x. [PMID: 17042918]
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