3-Chloro-L-tyrosine (BioDeep_00000398322)

Main id: BioDeep_00000018440

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


3-chloro-l-tyrosine hydrochloride

化学式: C9H10ClNO3 (215.034918)
中文名称: 3-氯-l-酪氨酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)Cl)O
InChI: InChI=1S/C9H10ClNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1

描述信息

A chloroamino acid comprising a tyrosine core with a chloro- substituent ortho to the phenolic hydroxy group.
D004791 - Enzyme Inhibitors
Acquisition and generation of the data is financially supported in part by CREST/JST.
3-Chloro-L-tyrosine is a specific marker of myeloperoxidase-catalyzed oxidation, and is markedly elevated in low density lipoprotein isolated from human atherosclerotic intima.

同义名列表

3 个代谢物同义名

3-Chloro-L-tyrosine; 3-chloro-l-tyrosine hydrochloride; 3-Chlorotyrosine



数据库引用编号

13 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)

1 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

  • Brooke G Pantazides, Brian S Crow, Jennifer Quiñones-González, Jonas W Perez, Jill A Harvilchuck, Jeffrey J Wallery, Tom C Hu, Jerry D Thomas, Rudolph C Johnson, Thomas A Blake. Development of a clinical assay to measure chlorinated tyrosine in hair and tissue samples using a mouse chlorine inhalation exposure model. Analytical and bioanalytical chemistry. 2021 Mar; 413(6):1765-1776. doi: 10.1007/s00216-020-03146-x. [PMID: 33511457]
  • Mariusz G Fleszar, Paulina Fortuna, Marek Zawadzki, Bogna Kosyk, Małgorzata Krzystek-Korpacka. Simultaneous LC-MS/MS-Based Quantification of Free 3-Nitro-l-tyrosine, 3-Chloro-l-tyrosine, and 3-Bromo-l-tyrosine in Plasma of Colorectal Cancer Patients during Early Postoperative Period. Molecules (Basel, Switzerland). 2020 Nov; 25(21):. doi: 10.3390/molecules25215158. [PMID: 33167555]
  • Lixia Zeng, Anna V Mathew, Jaeman Byun, Kevin B Atkins, Frank C Brosius, Subramaniam Pennathur. Myeloperoxidase-derived oxidants damage artery wall proteins in an animal model of chronic kidney disease-accelerated atherosclerosis. The Journal of biological chemistry. 2018 05; 293(19):7238-7249. doi: 10.1074/jbc.ra117.000559. [PMID: 29581235]
  • Farsad Afshinnia, Lixia Zeng, Jaeman Byun, Crystal A Gadegbeku, Maria Chiara Magnone, Carl Whatling, Barbara Valastro, Matthias Kretzler, Subramaniam Pennathur. Myeloperoxidase Levels and Its Product 3-Chlorotyrosine Predict Chronic Kidney Disease Severity and Associated Coronary Artery Disease. American journal of nephrology. 2017; 46(1):73-81. doi: 10.1159/000477766. [PMID: 28668952]
  • Brian S Crow, Jennifer Quiñones-González, Brooke G Pantazides, Jonas W Perez, W Rucks Winkeljohn, Joshua W Garton, Jerry D Thomas, Thomas A Blake, Rudolph C Johnson. Simultaneous Measurement of 3-Chlorotyrosine and 3,5-Dichlorotyrosine in Whole Blood, Serum and Plasma by Isotope Dilution HPLC-MS-MS. Journal of analytical toxicology. 2016 May; 40(4):264-71. doi: 10.1093/jat/bkw011. [PMID: 26977104]
  • Subramaniam Pennathur, Anuradha Vivekanandan-Giri, Morgan L Locy, Tejaswini Kulkarni, Degui Zhi, Lixia Zeng, Jaeman Byun, Joao A de Andrade, Victor J Thannickal. Oxidative Modifications of Protein Tyrosyl Residues Are Increased in Plasma of Human Subjects with Interstitial Lung Disease. American journal of respiratory and critical care medicine. 2016 Apr; 193(8):861-8. doi: 10.1164/rccm.201505-0992oc. [PMID: 26575972]
  • Daniela Pelclova, Vladimir Zdimal, Petr Kacer, Zdenka Fenclova, Stepanka Vlckova, Kamila Syslova, Tomas Navratil, Jaroslav Schwarz, Nadezda Zikova, Hana Barosova, Francesco Turci, Martin Komarc, Tomas Pelcl, Jaroslav Belacek, Jana Kukutschova, Sergey Zakharov. Oxidative stress markers are elevated in exhaled breath condensate of workers exposed to nanoparticles during iron oxide pigment production. Journal of breath research. 2016 Feb; 10(1):016004. doi: 10.1088/1752-7155/10/1/016004. [PMID: 26828137]
  • Anuradha Vivekanandan-Giri, Jessica L Slocum, Jaeman Byun, Chongren Tang, Robin L Sands, Brenda W Gillespie, Jay W Heinecke, Rajiv Saran, Mariana J Kaplan, Subramaniam Pennathur. High density lipoprotein is targeted for oxidation by myeloperoxidase in rheumatoid arthritis. Annals of the rheumatic diseases. 2013 Oct; 72(10):1725-31. doi: 10.1136/annrheumdis-2012-202033. [PMID: 23313808]
  • Charles G Knutson, Aswin Mangerich, Yu Zeng, Arkadiusz R Raczynski, Rosa G Liberman, Pilsoo Kang, Wenjie Ye, Erin G Prestwich, Kun Lu, John S Wishnok, Joshua R Korzenik, Gerald N Wogan, James G Fox, Peter C Dedon, Steven R Tannenbaum. Chemical and cytokine features of innate immunity characterize serum and tissue profiles in inflammatory bowel disease. Proceedings of the National Academy of Sciences of the United States of America. 2013 Jun; 110(26):E2332-41. doi: 10.1073/pnas.1222669110. [PMID: 23754421]
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  • Haixia Ren, Licheng Wang, Xusheng Wang, Xia Liu, Shengxiang Jiang. Measurement of acid dissociation constants and ionic mobilities of 3-nitro-tyrosine and 3-chloro-tyrosine by capillary zone electrophoresis. Journal of pharmaceutical and biomedical analysis. 2013 Apr; 77(?):83-7. doi: 10.1016/j.jpba.2013.01.015. [PMID: 23384554]
  • Michael Holzer, Klaus Zangger, Dalia El-Gamal, Veronika Binder, Sanja Curcic, Viktoria Konya, Rufina Schuligoi, Akos Heinemann, Gunther Marsche. Myeloperoxidase-derived chlorinating species induce protein carbamylation through decomposition of thiocyanate and urea: novel pathways generating dysfunctional high-density lipoprotein. Antioxidants & redox signaling. 2012 Oct; 17(8):1043-52. doi: 10.1089/ars.2011.4403. [PMID: 22462773]
  • Wai Mun Loke, Karen Mary-Jane Lam, Wan Ling Chong, Soh Eng Chew, Amy Ml Quek, Erle Ch Lim, Raymond Cs Seet. Products of 5-lipoxygenase and myeloperoxidase activities are increased in young male cigarette smokers. Free radical research. 2012 Oct; 46(10):1230-7. doi: 10.3109/10715762.2012.701291. [PMID: 22690830]
  • Lisa K Stamp, Irada Khalilova, Joanna M Tarr, Revathy Senthilmohan, Rufus Turner, Richard C Haigh, Paul G Winyard, Anthony J Kettle. Myeloperoxidase and oxidative stress in rheumatoid arthritis. Rheumatology (Oxford, England). 2012 Oct; 51(10):1796-803. doi: 10.1093/rheumatology/kes193. [PMID: 22814531]
  • Cédric Delporte, Thierry Franck, Caroline Noyon, Damien Dufour, Alexandre Rousseau, Philippe Madhoun, Jean-Marc Desmet, Didier Serteyn, Martine Raes, Joëlle Nortier, Michel Vanhaeverbeek, Nicole Moguilevsky, Jean Nève, Luc Vanhamme, Pierre Van Antwerpen, Karim Zouaoui Boudjeltia. Simultaneous measurement of protein-bound 3-chlorotyrosine and homocitrulline by LC-MS/MS after hydrolysis assisted by microwave: application to the study of myeloperoxidase activity during hemodialysis. Talanta. 2012 Sep; 99(?):603-9. doi: 10.1016/j.talanta.2012.06.044. [PMID: 22967600]
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  • Jihan Talib, David I Pattison, Jason A Harmer, David S Celermajer, Michael J Davies. High plasma thiocyanate levels modulate protein damage induced by myeloperoxidase and perturb measurement of 3-chlorotyrosine. Free radical biology & medicine. 2012 Jul; 53(1):20-9. doi: 10.1016/j.freeradbiomed.2012.04.018. [PMID: 22609005]
  • Baohai Shao. Site-specific oxidation of apolipoprotein A-I impairs cholesterol export by ABCA1, a key cardioprotective function of HDL. Biochimica et biophysica acta. 2012 Mar; 1821(3):490-501. doi: 10.1016/j.bbalip.2011.11.011. [PMID: 22178192]
  • Baohai Shao, Subramaniam Pennathur, Jay W Heinecke. Myeloperoxidase targets apolipoprotein A-I, the major high density lipoprotein protein, for site-specific oxidation in human atherosclerotic lesions. The Journal of biological chemistry. 2012 Feb; 287(9):6375-86. doi: 10.1074/jbc.m111.337345. [PMID: 22219194]
  • Hisae Oku, Yuko Ogawa, Emiko Iwaoka, Yu Yamaguchi, Satomi Kagota, Shinozuka Kazumasa, Masaru Kunitomo, Kyoko Ishiguro. Preventive effects of the extract of kinka-cha, a folk tea, on a rat model of metabolic syndrome. Journal of natural medicines. 2011 Jul; 65(3-4):610-6. doi: 10.1007/s11418-011-0523-0. [PMID: 21479861]
  • Michael Holzer, Martin Gauster, Thomas Pfeifer, Christian Wadsack, Guenter Fauler, Philipp Stiegler, Harald Koefeler, Eckhard Beubler, Rufina Schuligoi, Akos Heinemann, Gunther Marsche. Protein carbamylation renders high-density lipoprotein dysfunctional. Antioxidants & redox signaling. 2011 Jun; 14(12):2337-46. doi: 10.1089/ars.2010.3640. [PMID: 21235354]
  • Marija Bošković, Tomaž Vovk, Blanka Kores Plesničar, Iztok Grabnar. Oxidative stress in schizophrenia. Current neuropharmacology. 2011 Jun; 9(2):301-12. doi: 10.2174/157015911795596595. [PMID: 22131939]
  • Betul Catalgol, Nesrin Kartal Ozer. Lipid rafts and redox regulation of cellular signaling in cholesterol induced atherosclerosis. Current cardiology reviews. 2010 Nov; 6(4):309-24. doi: 10.2174/157340310793566181. [PMID: 22043207]
  • Megan E McBee, Yu Zeng, Nicola Parry, Cathryn R Nagler, Steven R Tannenbaum, David B Schauer. Multivariate modeling identifies neutrophil- and Th17-related factors as differential serum biomarkers of chronic murine colitis. PloS one. 2010 Oct; 5(10):e13277. doi: 10.1371/journal.pone.0013277. [PMID: 20976045]
  • Baohai Shao, Chongren Tang, Jay W Heinecke, John F Oram. Oxidation of apolipoprotein A-I by myeloperoxidase impairs the initial interactions with ABCA1 required for signaling and cholesterol export. Journal of lipid research. 2010 Jul; 51(7):1849-58. doi: 10.1194/jlr.m004085. [PMID: 20064972]
  • Gurusankar Saravanabhavan, Erica Blais, Renaud Vincent, Prem Kumarathasan. A high performance liquid chromatography-electrochemical array method for the measurement of oxidative/nitrative changes in human urine. Journal of chromatography. A. 2010 May; 1217(19):3269-74. doi: 10.1016/j.chroma.2010.01.048. [PMID: 20153474]
  • Volker Rudolph, René P Andrié, Tanja K Rudolph, Kai Friedrichs, Anna Klinke, Birgit Hirsch-Hoffmann, Alexander P Schwoerer, Denise Lau, Xiaoming Fu, Karin Klingel, Karsten Sydow, Michael Didié, Anika Seniuk, Eike-Christin von Leitner, Katalin Szoecs, Jan W Schrickel, Hendrik Treede, Ulrich Wenzel, Thorsten Lewalter, Georg Nickenig, Wolfram-Hubertus Zimmermann, Thomas Meinertz, Rainer H Böger, Hermann Reichenspurner, Bruce A Freeman, Thomas Eschenhagen, Heimo Ehmke, Stanley L Hazen, Stephan Willems, Stephan Baldus. Myeloperoxidase acts as a profibrotic mediator of atrial fibrillation. Nature medicine. 2010 Apr; 16(4):470-4. doi: 10.1038/nm.2124. [PMID: 20305660]
  • Agnieszka Robaszkiewicz. [Markers of chloric acid (I) in biological systems--identification and properties]. Postepy biochemii. 2010; 56(2):201-8. doi: NULL. [PMID: 20873115]
  • Philippe Paquet, Donat De Groote, Gérald E Piérard. Functionally active macrophage-derived myeloperoxidase in the skin of drug-induced toxic epidermal necrolysis. Dermatology (Basel, Switzerland). 2010; 220(3):201-7. doi: 10.1159/000284592. [PMID: 20332596]
  • Guoxiang Xie, Mao Ye, Yungang Wang, Yan Ni, Mingming Su, Hua Huang, Mingfeng Qiu, Aihua Zhao, Xiaojiao Zheng, Tianlu Chen, Wei Jia. Characterization of pu-erh tea using chemical and metabolic profiling approaches. Journal of agricultural and food chemistry. 2009 Apr; 57(8):3046-54. doi: 10.1021/jf804000y. [PMID: 19320437]
  • Yoji Kato, Natsuko Dozaki, Toshiyuki Nakamura, Noritoshi Kitamoto, Akihiro Yoshida, Michitaka Naito, Masayasu Kitamura, Toshihiko Osawa. Quantification of Modified Tyrosines in Healthy and Diabetic Human Urine using Liquid Chromatography/Tandem Mass Spectrometry. Journal of clinical biochemistry and nutrition. 2009 Jan; 44(1):67-78. doi: 10.3164/jcbn.08-185. [PMID: 19177191]
  • Masaru Kunitomo, Yu Yamaguchi, Satomi Kagota, Kazumasa Otsubo. Beneficial effect of coenzyme Q10 on increased oxidative and nitrative stress and inflammation and individual metabolic components developing in a rat model of metabolic syndrome. Journal of pharmacological sciences. 2008 Jun; 107(2):128-37. doi: 10.1254/jphs.fp0072365. [PMID: 18544898]
  • Mei-Ling Cheng, Chin-Ming Chen, Po-Wen Gu, Hung-Yao Ho, Daniel Tsun-Yee Chiu. Elevated levels of myeloperoxidase, white blood cell count and 3-chlorotyrosine in Taiwanese patients with acute myocardial infarction. Clinical biochemistry. 2008 May; 41(7-8):554-60. doi: 10.1016/j.clinbiochem.2008.02.006. [PMID: 18314009]
  • Alejandro Gugliucci. Hypochlorous acid is a potent inactivator of human plasminogen at concentrations secreted by activated granulocytes. Clinical chemistry and laboratory medicine. 2008; 46(10):1403-9. doi: 10.1515/cclm.2008.272. [PMID: 18759683]
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  • Yu Yamaguchi, Noriko Yoshikawa, Satomi Kagota, Kazuki Nakamura, Jun Haginaka, Masaru Kunitomo. Elevated circulating levels of markers of oxidative-nitrative stress and inflammation in a genetic rat model of metabolic syndrome. Nitric oxide : biology and chemistry. 2006 Dec; 15(4):380-6. doi: 10.1016/j.niox.2006.04.264. [PMID: 16798031]
  • Yu Yamaguchi, Kotaro Yamada, Noriko Yoshikawa, Kazuki Nakamura, Jun Haginaka, Masaru Kunitomo. Corosolic acid prevents oxidative stress, inflammation and hypertension in SHR/NDmcr-cp rats, a model of metabolic syndrome. Life sciences. 2006 Nov; 79(26):2474-9. doi: 10.1016/j.lfs.2006.08.007. [PMID: 16959274]
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