3-Methoxytyrosine (BioDeep_00000415776)

 

Secondary id: BioDeep_00000054229, BioDeep_00000625078

natural product PANOMIX_OTCML-2023 BioNovoGene_Lab2019


代谢物信息卡片


(DL)-3-O-Methyldopa

化学式: C10H13NO4 (211.0844538)
中文名称: rac 3-O-甲基DOPA
谱图信息: 最多检出来源 Viridiplantae(plant) 0.43%

分子结构信息

SMILES: COC1=C(C=CC(=C1)CC(C(=O)O)N)O
InChI: InChI=1S/C10H13NO4/c1-15-9-5-6(2-3-8(9)12)4-7(11)10(13)14/h2-3,5,7,12H,4,11H2,1H3,(H,13,14)

描述信息

3-O-Methyldopa (3-Methoxy-L-tyrosine) is a metabolite of L-DOPA which is formed by catechol-O-methyltransferase (COMT). 3-O-Methyldopa competitively inhibits the pharmacodynamics of l-DOPA and dopamine[1].
3-O-Methyldopa (3-Methoxy-L-tyrosine) is a metabolite of L-DOPA which is formed by catechol-O-methyltransferase (COMT). 3-O-Methyldopa competitively inhibits the pharmacodynamics of l-DOPA and dopamine[1].

同义名列表

5 个代谢物同义名

(DL)-3-O-Methyldopa; 3-Methoxytyrosine; 3-Methoxy-L-tyrosine; 3-O-Methyl-L-DOPA; 3-O-Methyldopa



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)

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PharmGKB(0)

0 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

  • Shwu-Jiuan Lin, Lily Tai, Yu-Jie Huang, Yow-Shieng Uang, Yih Ho, Kuang-Yang Hsu, Li-Hsuan Wang. Effect of catechin and commercial preparation of green tea essence on the pharmacokinetics of l-dopa in rabbits. Biomedical chromatography : BMC. 2021 Dec; 35(12):e5227. doi: 10.1002/bmc.5227. [PMID: 34388856]
  • Masahiro Nomoto, Atsushi Takeda, Katsuaki Iwai, Akihisa Nishimura, Nobutaka Hattori. Effect of Opicapone Tablets on Levodopa and 3-O-Methyldopa Pharmacokinetics in Healthy Japanese Subjects: Phase 1 Study. Clinical pharmacology in drug development. 2021 02; 10(2):180-189. doi: 10.1002/cpdd.799. [PMID: 32416054]
  • Mirko Peitzsch, Elizabeth R Butch, Elizabeth Lovorn, Anastasios Mangelis, Wayne L Furman, Victor M Santana, Barbara Hero, Frank Berthold, Barry L Shulkin, Angela Huebner, Graeme Eisenhofer. Biochemical testing for neuroblastoma using plasma free 3-O-methyldopa, 3-methoxytyramine, and normetanephrine. Pediatric blood & cancer. 2020 02; 67(2):e28081. doi: 10.1002/pbc.28081. [PMID: 31724812]
  • Mirko Peitzsch, Anastasios Mangelis, Graeme Eisenhofer, Angela Huebner. Age-specific pediatric reference intervals for plasma free normetanephrine, metanephrine, 3-methoxytyramine and 3-O-methyldopa: Particular importance for early infancy. Clinica chimica acta; international journal of clinical chemistry. 2019 Jul; 494(?):100-105. doi: 10.1016/j.cca.2019.03.1620. [PMID: 30904545]
  • Siegfried Muhlack, Manuel Kinkel, Lennard Herrman, Thomas Müller. Levodopa, placebo and rotigotine change biomarker levels for oxidative stress. Neurological research. 2017 May; 39(5):381-386. doi: 10.1080/01616412.2017.1295520. [PMID: 28222651]
  • Prashant P Raut, Shrikant Y Charde, Pradeep Bishnoi. Simultaneous estimation of levodopa, carbidopa and 3-oxymethyldopa in rat plasma using HPLC-ECD. Biomedical chromatography : BMC. 2016 Oct; 30(10):1696-700. doi: 10.1002/bmc.3713. [PMID: 26910491]
  • Paldeep S Atwal, Taraka R Donti, Aaron L Cardon, C A Bacino, Qin Sun, L Emrick, V Reid Sutton, Sarah H Elsea. Aromatic L-amino acid decarboxylase deficiency diagnosed by clinical metabolomic profiling of plasma. Molecular genetics and metabolism. 2015 Jun; 115(2-3):91-4. doi: 10.1016/j.ymgme.2015.04.008. [PMID: 25956449]
  • Rômulo Pereira Ribeiro, João Cleverson Gasparetto, Raquel de Oliveira Vilhena, Thais Martins Guimarães de Francisco, Thais Martins Guimarães de Francisco, Cleverson Antônio Ferreira Martins, Marco André Cardoso, Roberto Pontarolo, Katherine Athayde Teixeira de Carvalho. Simultaneous determination of levodopa, carbidopa, entacapone, tolcapone, 3-O-methyldopa and dopamine in human plasma by an HPLC-MS/MS method. Bioanalysis. 2015; 7(2):207-20. doi: 10.4155/bio.14.230. [PMID: 25587837]
  • Qu Qi, Lijuan Cao, Feiyan Li, Hong Wang, Huiying Liu, Haiping Hao, Kun Hao. Salvianolic acid B as a substrate and weak catechol-O-methyltransferase inhibitor in rats. Xenobiotica; the fate of foreign compounds in biological systems. 2015; 45(9):820-7. doi: 10.3109/00498254.2015.1017753. [PMID: 25869243]
  • Ewa Narożańska, Monika Białecka, Urszula Adamiak-Giera, Barbara Gawrońska-Szklarz, Witold Sołtan, Michał Schinwelski, Piotr Robowski, Mariusz H Madaliński, Jarosław Sławek. Pharmacokinetics of levodopa in patients with Parkinson disease and motor fluctuations depending on the presence of Helicobacter pylori infection. Clinical neuropharmacology. 2014 Jul; 37(4):96-9. doi: 10.1097/wnf.0000000000000037. [PMID: 24992088]
  • Dag Nyholm, Per Odin, Anders Johansson, Krai Chatamra, Charles Locke, Sandeep Dutta, Ahmed A Othman. Pharmacokinetics of levodopa, carbidopa, and 3-O-methyldopa following 16-hour jejunal infusion of levodopa-carbidopa intestinal gel in advanced Parkinson's disease patients. The AAPS journal. 2013 Apr; 15(2):316-23. doi: 10.1208/s12248-012-9439-1. [PMID: 23229334]
  • Thomas Müller, Constanze Jugel, Siegfried Muhlack, Fabian Klostermann. Methyl group-donating vitamins elevate 3-O-methyldopa in patients with Parkinson disease. Clinical neuropharmacology. 2013 Mar; 36(2):52-4. doi: 10.1097/wnf.0b013e318283fa18. [PMID: 23503547]
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  • Aiko Ishihara, Takafumi Miyachi, Takeshi Nakamura, Toshiho Ohtsuki, Yasuhiro Kimura, Kenji Kihira, Takemori Yamawaki, Masayasu Matsumoto. Relationship between 3-O-methyldopa and the clinical effects of entacapone in advanced Parkinson's disease. Hiroshima journal of medical sciences. 2011 Sep; 60(3):57-62. doi: . [PMID: 22053701]
  • Thomas Müller, Dirk Woitalla, Siegfried Muhlack. Inhibition of catechol-O-methyltransferase modifies acute homocysteine rise during repeated levodopa application in patients with Parkinson's disease. Naunyn-Schmiedeberg's archives of pharmacology. 2011 Jun; 383(6):627-33. doi: 10.1007/s00210-011-0629-7. [PMID: 21533995]
  • Thomas Müller, Siegfried Muhlack. Cysteinyl-glycine reduction as marker for levodopa-induced oxidative stress in Parkinson's disease patients. Movement disorders : official journal of the Movement Disorder Society. 2011 Feb; 26(3):543-6. doi: 10.1002/mds.23384. [PMID: 21462263]
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  • Li-Hsuan Wang, Kuang-Yang Hsu, Yow-Shieng Uang, Feng-Lin Hsu, Li-Ming Yang, Shwu-Jiuan Lin. Caffeic acid improves the bioavailability of L-dopa in rabbit plasma. Phytotherapy research : PTR. 2010 Jun; 24(6):852-8. doi: 10.1002/ptr.3031. [PMID: 19941381]
  • Urszula Adamiak, Maria Kaldonska, Gabriela Klodowska-Duda, Elzbieta Wyska, Krzysztof Safranow, Monika Bialecka, Barbara Gawronska-Szklarz. Pharmacokinetic-pharmacodynamic modeling of levodopa in patients with advanced Parkinson disease. Clinical neuropharmacology. 2010 May; 33(3):135-41. doi: 10.1097/wnf.0b013e3181d47849. [PMID: 20216409]
  • Teresa Nunes, Rita Machado, José F Rocha, Carlos Fernandes-Lopes, Raquel Costa, Leonel Torrão, Ana I Loureiro, Amílcar Falcão, Manuel Vaz-da-Silva, Lyndon Wright, Luis Almeida, Patricio Soares-da-Silva. Pharmacokinetic-pharmacodynamic interaction between nebicapone and controlled-release levodopa/benserazide: a single-center, Phase I, double-blind, randomized, placebo-controlled, four-way crossover study in healthy subjects. Clinical therapeutics. 2009 Oct; 31(10):2258-71. doi: 10.1016/j.clinthera.2009.10.019. [PMID: 19922897]
  • Thomas Müller, Siegfried Muhlack. Peripheral COMT inhibition prevents levodopa associated homocysteine increase. Journal of neural transmission (Vienna, Austria : 1996). 2009 Oct; 116(10):1253-6. doi: 10.1007/s00702-009-0275-0. [PMID: 19657587]
  • Thomas Müller, Wilfried Kuhn. Homocysteine levels after acute levodopa intake in patients with Parkinson's disease. Movement disorders : official journal of the Movement Disorder Society. 2009 Jul; 24(9):1339-43. doi: 10.1002/mds.22607. [PMID: 19425084]
  • Thomas Müller, Kira Kolf, Lema Ander, Dirk Woitalla, Siegfried Muhlack. Catechol-O-methyltransferase inhibition improves levodopa-associated strength increase in patients with Parkinson disease. Clinical neuropharmacology. 2008 May; 31(3):134-40. doi: 10.1097/wnf.0b013e31811510ed. [PMID: 18520980]
  • Chiara Muzzi, Erica Bertocci, Lucia Terzuoli, Brunetta Porcelli, Ilaria Ciari, Roberto Pagani, Roberto Guerranti. Simultaneous determination of serum concentrations of levodopa, dopamine, 3-O-methyldopa and alpha-methyldopa by HPLC. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2008 Apr; 62(4):253-8. doi: 10.1016/j.biopha.2007.10.018. [PMID: 18158229]
  • Eun-Sook Y Lee, Hongtao Chen, Jennifer King, Clivel Charlton. The role of 3-O-methyldopa in the side effects of L-dopa. Neurochemical research. 2008 Mar; 33(3):401-11. doi: 10.1007/s11064-007-9442-6. [PMID: 17713853]
  • Manuel Vaz-da-Silva, Ana I Loureiro, Teresa Nunes, Carlos Lopes, José Rocha, Rita Machado, Raquel Costa, Leonel Torrão, Amílcar Falcão, Lyndon Wright, Luis Almeida, Patrício Soares-da-Silva. Pharmacokinetic-pharmacodynamic interaction between nebicapone, a novel catechol-o-methyltransferase inhibitor, and controlled-release levodopa/carbidopa 200 mg/50 mg : randomized, double-blind, placebo-controlled, crossover study in healthy subjects. Drugs in R&D. 2008; 9(6):435-46. doi: 10.2165/0126839-200809060-00006. [PMID: 18989992]
  • T Müller, J Welnic, S Muhlack. Acute levodopa administration reduces cortisol release in patients with Parkinson's disease. Journal of neural transmission (Vienna, Austria : 1996). 2007 Mar; 114(3):347-50. doi: 10.1007/s00702-006-0552-0. [PMID: 16932991]
  • T Müller, L Ander, K Kolf, D Woitalla, S Muhlack. Comparison of 200 mg retarded release levodopa/carbidopa - with 150 mg levodopa/carbidopa/entacapone application: pharmacokinetics and efficacy in patients with Parkinson's disease. Journal of neural transmission (Vienna, Austria : 1996). 2007; 114(11):1457-62. doi: 10.1007/s00702-007-0773-x. [PMID: 17564755]
  • T Müller, C Erdmann, S Muhlack, D Bremen, H Przuntek, O Goetze, D Woitalla. Pharmacokinetic behaviour of levodopa and 3-O-methyldopa after repeat administration of levodopa/carbidopa with and without entacapone in patients with Parkinson's disease. Journal of neural transmission (Vienna, Austria : 1996). 2006 Oct; 113(10):1441-8. doi: 10.1007/s00702-006-0442-5. [PMID: 16604302]
  • Morvarid Karimi, Juanita L Carl, Susan Loftin, Joel S Perlmutter. Modified high-performance liquid chromatography with electrochemical detection method for plasma measurement of levodopa, 3-O-methyldopa, dopamine, carbidopa and 3,4-dihydroxyphenyl acetic acid. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 May; 836(1-2):120-3. doi: 10.1016/j.jchromb.2006.03.027. [PMID: 16584928]
  • Eun-Sook Y Lee, Hongtao Chen, Karam F A Soliman, Clivel G Charlton. Effects of homocysteine on the dopaminergic system and behavior in rodents. Neurotoxicology. 2005 Jun; 26(3):361-71. doi: 10.1016/j.neuro.2005.01.008. [PMID: 15935208]
  • Siegfried Muhlack, Dirk Woitalla, Jacob Welnic, Svenja Twiehaus, Horst Przuntek, Thomas Müller. Chronic levodopa intake increases levodopa plasma bioavailability in patients with Parkinson's disease. Neuroscience letters. 2004 Jun; 363(3):284-7. doi: 10.1016/j.neulet.2004.04.012. [PMID: 15182961]
  • R Pons, B Ford, C A Chiriboga, P T Clayton, V Hinton, K Hyland, R Sharma, D C De Vivo. Aromatic L-amino acid decarboxylase deficiency: clinical features, treatment, and prognosis. Neurology. 2004 Apr; 62(7):1058-65. doi: 10.1212/wnl.62.7.1058. [PMID: 15079002]
  • Christoph Saxer, Miyuki Niina, Akinori Nakashima, Yusuke Nagae, Naoki Masuda. Simultaneous determination of levodopa and 3-O-methyldopa in human plasma by liquid chromatography with electrochemical detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Apr; 802(2):299-305. doi: 10.1016/j.jchromb.2003.12.006. [PMID: 15018791]
  • Pedro Silveira, Manuel Vaz-da-Silva, Luis Almeida, Joana Maia, Amilcar Falcão, Ana Loureiro, Leonel Torrão, Rita Machado, Lyndon Wright, Patrício Soares-da-Silva. Pharmacokinetic-pharmacodynamic interaction between BIA 3-202, a novel COMT inhibitor, and levodopa/benserazide. European journal of clinical pharmacology. 2003 Nov; 59(8-9):603-9. doi: 10.1007/s00228-003-0680-5. [PMID: 14517707]
  • F Blandini, G Nappi, R Fancellu, A Mangiagalli, A Samuele, G Riboldazzi, D Calandrella, C Pacchetti, G Bono, E Martignoni. Modifications of plasma and platelet levels of L-DOPA and its direct metabolites during treatment with tolcapone or entacapone in patients with Parkinson's disease. Journal of neural transmission (Vienna, Austria : 1996). 2003 Aug; 110(8):911-22. doi: 10.1007/s00702-003-0004-z. [PMID: 12898346]
  • Charles Crevoisier, Patricia Zerr, Françoise Calvi-Gries, Turid Nilsen. Effects of food on the pharmacokinetics of levodopa in a dual-release formulation. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2003 Jan; 55(1):71-6. doi: 10.1016/s0939-6411(02)00124-8. [PMID: 12551706]
  • Kunio Yui, Shigenori Ikemoto, Kimihiko Goto. Factors for susceptibility to episode recurrence in spontaneous recurrence of methamphetamine psychosis. Annals of the New York Academy of Sciences. 2002 Jun; 965(?):292-304. doi: 10.1111/j.1749-6632.2002.tb04171.x. [PMID: 12105105]
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