Methionine sulfoxide (BioDeep_00000001378)

 

Secondary id: BioDeep_00000177895, BioDeep_00000398709, BioDeep_00000402858, BioDeep_00000838380

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


α-amino-γ-(methylsulfinyl)-Butyric acid

化学式: C5H11NO3S (165.0459616)
中文名称: DL-蛋氨酸亚砜, L-蛋氨酸亚砜, 蛋氨酸亚砜
谱图信息: 最多检出来源 Homo sapiens(feces) 20.18%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Methionine sulfoxide. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/methionine_sulfoxide (retrieved 2024-12-04) (BioDeep RN: BioDeep_00000001378). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CS(=O)CCC(C(=O)O)N
InChI: InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

描述信息

Methionine sulfoxide belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Methionine sulfoxide exists in all living species, ranging from bacteria to humans. Within humans, methionine sulfoxide participates in a number of enzymatic reactions. In particular, methionine sulfoxide can be biosynthesized from L-methionine through its interaction with the enzyme methionine-R-sulfoxide reductase B3. In addition, methionine sulfoxide can be biosynthesized from L-methionine through the action of the enzyme methionine-R-sulfoxide reductase b2, mitochondrial. In humans, methionine sulfoxide is involved in the metabolic disorder called hypermethioninemia.
Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species via 2-electron-dependent mechanism. Such oxidants can be generated from activated neutrophils; therefore, methionine sulfoxide can be regarded as a biomarker of oxidative stress in vivo. (PMID 12576054) [HMDB]. Methionine sulfoxide is found in many foods, some of which are romaine lettuce, white cabbage, dill, and yellow bell pepper.
L-Methionine sulfoxide (H-Met(O)-OH), a metabolite of Methionine, induces M1/classical macrophage polarization, and modulates oxidative stress and purinergic signaling parameters[1].
Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species and can be regarded as a biomarker of oxidative stress in vivo.
Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species and can be regarded as a biomarker of oxidative stress in vivo.

同义名列表

26 个代谢物同义名

α-amino-γ-(methylsulfinyl)-Butyric acid; Methionine sulfoxide, 35S-labeled, (+-)-isomer; (2S)-2-amino-4-methanesulfinylbutanoic acid; Butanoic acid, 2-amino-4-(methylsulfinyl)-; Methionine sulfoxide, (R-(r*,s*))-isomer; 2-amino-4-(Methylsulfinyl)-butanoic acid; Methionine sulfoxide, (S-(r*,s*))-isomer; 2-amino-4-methylsulfinyl-butanoic acid; 2-amino-4-(Methylsulfinyl)-butanoate; Methionine sulfoxide, (+-)-isomer; Methionine sulfoxide, (2R)-isomer; Methionine sulfoxide, (2S)-isomer; L-Methionine (S)-S-oxide; L-Methionine sulphoxide; DL-Methionine sulfoxide; L-Methionine sulfoxide; Methionine sulphoxide; L-Methionine S-oxide; L-Methionine R-oxide; Methionine sulfoxide; S-Oxide-methionine; Methionine S-oxide; H-Met(O)-OH; Methionine sulfoxide; L-Methionine S-oxide; L-methionine sulfoxide



数据库引用编号

30 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

28 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(25)

PharmGKB(0)

15 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

  • Ewa Marzena Kalemba, Kris Gevaert, Francis Impens, Sara Dufour, Anna Czerwoniec. The association of protein-bound methionine sulfoxide with proteomic basis for aging in beech seeds. BMC plant biology. 2024 May; 24(1):377. doi: 10.1186/s12870-024-05085-6. [PMID: 38714916]
  • Darren Leahy, Cameron Grant, Alex Jackson, Alex Duff, Nicholas Tardiota, Jessica Van Haeften, Xingchen Chen, Jonathan M Peake, Michael D Kruppa, Eliot T Smith, David A Johnson, William B Lott, Jonathan M Harris. Discrimination of Methionine Sulfoxide and Sulfone by Human Neutrophil Elastase. Molecules (Basel, Switzerland). 2021 Sep; 26(17):. doi: 10.3390/molecules26175344. [PMID: 34500777]
  • Natalia Wojciechowska, Shirin Alipour, Ewelina Stolarska, Karolina Bilska, Pascal Rey, Ewa M Kalemba. Involvement of the MetO/Msr System in Two Acer Species That Display Contrasting Characteristics during Germination. International journal of molecular sciences. 2020 Dec; 21(23):. doi: 10.3390/ijms21239197. [PMID: 33276642]
  • Su H Chu, Jing Cui, Jeffrey A Sparks, Bing Lu, Sara K Tedeschi, Cameron B Speyer, LauraKay Moss, Marie L Feser, Lindsay B Kelmenson, Elizabeth A Mewshaw, Jess D Edison, Kevin D Deane, Clary Clish, Jessica Lasky-Su, Elizabeth W Karlson, Karen H Costenbader. Circulating plasma metabolites and risk of rheumatoid arthritis in the Nurses' Health Study. Rheumatology (Oxford, England). 2020 11; 59(11):3369-3379. doi: 10.1093/rheumatology/keaa125. [PMID: 32310291]
  • Tiffany Thomas, Davide Stefanoni, Julie A Reisz, Travis Nemkov, Lorenzo Bertolone, Richard O Francis, Krystalyn E Hudson, James C Zimring, Kirk C Hansen, Eldad A Hod, Steven L Spitalnik, Angelo D'Alessandro. COVID-19 infection alters kynurenine and fatty acid metabolism, correlating with IL-6 levels and renal status. JCI insight. 2020 07; 5(14):. doi: 10.1172/jci.insight.140327. [PMID: 32559180]
  • Thaís S Franceschi, Mayara S P Soares, Nathalia S Pedra, Natália P Bona, Luiza Spohr, Fernanda C Teixeira, Carlus A T do Couto, Roselia M Spanevello, Marion Deon, Carmen R Vargas, Elizandra Braganhol, Francieli M Stefanello. Characterization of macrophage phenotype, redox, and purinergic response upon chronic treatment with methionine and methionine sulfoxide in mice. Amino acids. 2020 Apr; 52(4):629-638. doi: 10.1007/s00726-020-02841-4. [PMID: 32246211]
  • Kristine B Holte, Mona Svanteson, Kristian F Hanssen, Kari Anne Sveen, Ingebjørg Seljeflot, Svein Solheim, David R Sell, Vincent M Monnier, Tore Julsrud Berg. Collagen methionine sulfoxide and glucuronidine/LW-1 are markers of coronary artery disease in long-term survivors with type 1 diabetes. The Dialong study. PloS one. 2020; 15(5):e0233174. doi: 10.1371/journal.pone.0233174. [PMID: 32401813]
  • Maurizio Bruschi, Andrea Petretto, Laura Santucci, Augusto Vaglio, Federico Pratesi, Paola Migliorini, Roberta Bertelli, Chiara Lavarello, Martina Bartolucci, Giovanni Candiano, Marco Prunotto, Gian Marco Ghiggeri. Neutrophil Extracellular Traps protein composition is specific for patients with Lupus nephritis and includes methyl-oxidized αenolase (methionine sulfoxide 93). Scientific reports. 2019 05; 9(1):7934. doi: 10.1038/s41598-019-44379-w. [PMID: 31138830]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
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  • Maria-Armineh Tossounian, Inge Van Molle, Khadija Wahni, Silke Jacques, Kris Gevaert, Frank Van Breusegem, Didier Vertommen, David Young, Leonardo Astolfi Rosado, Joris Messens. Disulfide bond formation protects Arabidopsis thaliana glutathione transferase tau 23 from oxidative damage. Biochimica et biophysica acta. General subjects. 2018 03; 1862(3):775-789. doi: 10.1016/j.bbagen.2017.10.007. [PMID: 29031766]
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  • Rupesh Bommana, Olivier Mozziconacci, Y John Wang, Christian Schöneich. An Efficient and Rapid Method to Monitor the Oxidative Degradation of Protein Pharmaceuticals: Probing Tyrosine Oxidation with Fluorogenic Derivatization. Pharmaceutical research. 2017 Jul; 34(7):1428-1443. doi: 10.1007/s11095-017-2159-6. [PMID: 28421307]
  • Audrey S Vanhove, Saiyu Hang, Vidhya Vijayakumar, Adam Cn Wong, John M Asara, Paula I Watnick. Vibrio cholerae ensures function of host proteins required for virulence through consumption of luminal methionine sulfoxide. PLoS pathogens. 2017 Jun; 13(6):e1006428. doi: 10.1371/journal.ppat.1006428. [PMID: 28586382]
  • Guoxiang Jiang, Lu Xiao, Huiling Yan, Dandan Zhang, Fuwang Wu, Xuncheng Liu, Xinguo Su, Xinhong Dong, Jiasheng Wang, Xuewu Duan, Yueming Jiang. Redox regulation of methionine in calmodulin affects the activity levels of senescence-related transcription factors in litchi. Biochimica et biophysica acta. General subjects. 2017 May; 1861(5 Pt A):1140-1151. doi: 10.1016/j.bbagen.2017.02.004. [PMID: 28188859]
  • Lien M Dos Santos, Tatiane M da Silva, Juliana H Azambuja, Priscila T Ramos, Pathise S Oliveira, Elita F da Silveira, Nathalia S Pedra, Kennia Galdino, Carlus A T do Couto, Mayara S P Soares, Rejane G Tavares, Roselia M Spanevello, Francieli M Stefanello, Elizandra Braganhol. Methionine and methionine sulfoxide treatment induces M1/classical macrophage polarization and modulates oxidative stress and purinergic signaling parameters. Molecular and cellular biochemistry. 2017 Jan; 424(1-2):69-78. doi: 10.1007/s11010-016-2843-6. [PMID: 27752805]
  • Mayara Sandrielly Pereira Soares, Pathise Souto Oliveira, Gabriela Nogueira Debom, Bruna da Silveira Mattos, Carla Roberta Polachini, Jucimara Baldissarelli, Vera Maria Morsch, Maria Rosa Chitolina Schetinger, Rejane Giacomelli Tavares, Francieli Moro Stefanello, Roselia Maria Spanevello. Chronic administration of methionine and/or methionine sulfoxide alters oxidative stress parameters and ALA-D activity in liver and kidney of young rats. Amino acids. 2017 01; 49(1):129-138. doi: 10.1007/s00726-016-2340-y. [PMID: 27718024]
  • Satoko Suzuki, Yoshio Kodera, Tatsuya Saito, Kazumi Fujimoto, Akari Momozono, Akinori Hayashi, Yuji Kamata, Masayoshi Shichiri. Methionine sulfoxides in serum proteins as potential clinical biomarkers of oxidative stress. Scientific reports. 2016 12; 6(?):38299. doi: 10.1038/srep38299. [PMID: 27929071]
  • Nathan J White, Yi Wang, Xiaoyun Fu, Jessica C Cardenas, Erika J Martin, Donald F Brophy, Charles E Wade, Xu Wang, Alexander E St John, Esther B Lim, Susan A Stern, Kevin R Ward, José A López, Dominic Chung. Post-translational oxidative modification of fibrinogen is associated with coagulopathy after traumatic injury. Free radical biology & medicine. 2016 07; 96(?):181-9. doi: 10.1016/j.freeradbiomed.2016.04.023. [PMID: 27105953]
  • Johannes Wüst, Monika Pischetsrieder. Methionine sulfoxide profiling of milk proteins to assess the influence of lipids on protein oxidation in milk. Food & function. 2016 Jun; 7(6):2526-36. doi: 10.1039/c5fo01550b. [PMID: 26927981]
  • Sara Samino, Maria Vinaixa, Marta Díaz, Antoni Beltran, Miguel A Rodríguez, Roger Mallol, Mercedes Heras, Anna Cabre, Lorena Garcia, Nuria Canela, Francis de Zegher, Xavier Correig, Lourdes Ibáñez, Oscar Yanes. Metabolomics reveals impaired maturation of HDL particles in adolescents with hyperinsulinaemic androgen excess. Scientific reports. 2015 Jun; 5(?):11496. doi: 10.1038/srep11496. [PMID: 26099471]
  • Silke Jacques, Bart Ghesquière, Pieter-Jan De Bock, Hans Demol, Khadija Wahni, Patrick Willems, Joris Messens, Frank Van Breusegem, Kris Gevaert. Protein Methionine Sulfoxide Dynamics in Arabidopsis thaliana under Oxidative Stress. Molecular & cellular proteomics : MCP. 2015 May; 14(5):1217-29. doi: 10.1074/mcp.m114.043729. [PMID: 25693801]
  • G Sartore, R Seraglia, S Burlina, A Bolis, R Marin, E Manzato, E Ragazzi, P Traldi, A Lapolla. High-density lipoprotein oxidation in type 2 diabetic patients and young patients with premature myocardial infarction. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2015 Apr; 25(4):418-25. doi: 10.1016/j.numecd.2014.12.004. [PMID: 25636381]
  • Yong Li, Sridhar A Malkaram, Jie Zhou, Janos Zempleni. Lysine biotinylation and methionine oxidation in the heat shock protein HSP60 synergize in the elimination of reactive oxygen species in human cell cultures. The Journal of nutritional biochemistry. 2014 Apr; 25(4):475-82. doi: 10.1016/j.jnutbio.2013.12.008. [PMID: 24582286]
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  • Silke Jacques, Bart Ghesquière, Frank Van Breusegem, Kris Gevaert. Plant proteins under oxidative attack. Proteomics. 2013 Mar; 13(6):932-40. doi: 10.1002/pmic.201200237. [PMID: 23172756]
  • Roberta Seraglia, Giovanni Sartore, Raffaella Marin, Silvia Burlina, Enzo Manzato, Eugenio Ragazzi, Pietro Traldi, Annunziata Lapolla. An effective and rapid determination by MALDI/TOF/TOF of methionine sulphoxide content of ApoA-I in type 2 diabetic patients. Journal of mass spectrometry : JMS. 2013 Jan; 48(1):105-10. doi: 10.1002/jms.3113. [PMID: 23303753]
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  • John M Ringman, Andrew T Fithian, Karen Gylys, Jeffrey L Cummings, Giovanni Coppola, David Elashoff, Domenico Pratico, Jackob Moskovitz, Gal Bitan. Plasma methionine sulfoxide in persons with familial Alzheimer's disease mutations. Dementia and geriatric cognitive disorders. 2012; 33(4):219-25. doi: 10.1159/000338546. [PMID: 22584618]
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