Methionine sulfoxide (BioDeep_00000398709)

Main id: BioDeep_00000001378

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


alpha-amino-gamma-(Methylsulfinyl)-butyric acid

化学式: C5H11NO3S (165.046)
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(blood) 22.87%

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

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; QEFRNWWLZKMPFJ-UHFFFAOYSA-N_STSL_0131_Methionine sulfoxide_2000fmol_180425_S2_LC02_MS02_81; 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.
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.052
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.050
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

15 个代谢物同义名

alpha-amino-gamma-(Methylsulfinyl)-butyric acid; 2-amino-4-(Methylsulfinyl)-butanoic acid; 2-amino-4-methylsulfinylbutanoic acid; 2-amino-4-(Methylsulfinyl)-butanoate; L-Methionine (S)-S-oxide; DL-Methionine sulfoxide; L-Methionine sulfoxide; L-Methionine R-oxide; Methionine sulfoxide; S-Oxide-methionine; H-Met(O)-OH; Butanoic acid, 2-amino-4-(methylsulfinyl)-; L-Methionine S-oxide; Methionine sulfoxide; L-methionine sulfoxide



数据库引用编号

34 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)

14 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。

亚细胞结构定位 关联基因列表
Cytoplasm 12 CASP3, CAT, ELANE, GLUL, GPX1, HPGDS, MICAL1, MSRA, MSRB1, MSRB3, PRDX6, TXN
Peripheral membrane protein 2 ACHE, HSD17B6
Endosome membrane 1 MICAL1
Nucleus 8 ACHE, CASP3, GLRX, GLUL, MPO, MSRB1, PRDX6, TXN
cytosol 14 APOA1, CASP3, CAT, ELANE, GLRX, GLUL, GPX1, HPGDS, MICAL1, MSRA, MSRB1, MSRB3, PRDX6, TXN
phagocytic vesicle 1 ELANE
nucleoplasm 6 CASP3, HPGDS, MPO, MSRA, MSRB1, TXN
Cell membrane 2 ACHE, GLUL
Lipid-anchor 2 GLUL, MSRA
Early endosome membrane 1 HSD17B6
Synapse 1 ACHE
cell surface 2 ACHE, ELANE
glutamatergic synapse 1 CASP3
Golgi apparatus 2 ACHE, SERPINA1
Golgi membrane 1 INS
neuromuscular junction 1 ACHE
neuronal cell body 1 CASP3
Cytoplasm, cytosol 1 GLUL
Lysosome 2 MPO, PRDX6
plasma membrane 5 ACHE, APOA1, GLUL, MICAL1, MSRA
Membrane 4 ACHE, CAT, MSRA, PRDX6
extracellular exosome 11 APOA1, CAT, ELANE, GLRX, GLUL, MPO, MSRA, PRDX6, SERPINA1, TXN, VWF
Lumenal side 1 HSD17B6
endoplasmic reticulum 5 GLUL, HSD17B6, MSRB3, SERPINA1, VWF
extracellular space 8 ACHE, APOA1, ELANE, INS, MPO, PRDX6, SERPINA1, VWF
perinuclear region of cytoplasm 2 ACHE, PRDX6
mitochondrion 6 CAT, GLUL, GPX1, MSRA, MSRB3, PRDX6
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 6 CAT, HPGDS, HSD17B6, MPO, MSRA, SERPINA1
Microsome membrane 1 HSD17B6
postsynaptic density 1 CASP3
Secreted 5 ACHE, APOA1, INS, TXN, VWF
extracellular region 10 ACHE, APOA1, CAT, ELANE, INS, MPO, PRDX6, SERPINA1, TXN, VWF
mitochondrial matrix 2 CAT, GPX1
Extracellular side 1 ACHE
Extracellular vesicle 1 APOA1
Secreted, extracellular space, extracellular matrix 1 VWF
chylomicron 1 APOA1
high-density lipoprotein particle 1 APOA1
low-density lipoprotein particle 1 APOA1
very-low-density lipoprotein particle 1 APOA1
actin cytoskeleton 3 MICAL1, MSRA, MSRB1
cytoplasmic vesicle 1 APOA1
midbody 2 MICAL1, MSRA
Early endosome 1 APOA1
COPII-coated ER to Golgi transport vesicle 1 SERPINA1
Cytoplasm, cytoskeleton 2 MICAL1, MSRB1
focal adhesion 1 CAT
extracellular matrix 1 VWF
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 4 APOA1, ELANE, SERPINA1, VWF
secretory granule 2 ELANE, MPO
intermediate filament 1 MICAL1
cytoskeleton 2 MICAL1, MSRB1
actin filament 1 MICAL1
blood microparticle 1 APOA1
Lipid-anchor, GPI-anchor 1 ACHE
intercellular bridge 1 MICAL1
endosome lumen 1 INS
cell body 1 GLUL
side of membrane 1 ACHE
azurophil granule 1 MPO
platelet alpha granule 1 VWF
Microsome 1 GLUL
ficolin-1-rich granule lumen 2 CAT, SERPINA1
secretory granule lumen 3 APOA1, CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 APOA1, INS, SERPINA1
transcription repressor complex 1 ELANE
platelet alpha granule lumen 2 SERPINA1, VWF
specific granule lumen 1 ELANE
endocytic vesicle 1 APOA1
transport vesicle 1 INS
azurophil granule lumen 3 ELANE, MPO, PRDX6
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 INS, SERPINA1
phagocytic vesicle lumen 1 MPO
synaptic cleft 1 ACHE
death-inducing signaling complex 1 CASP3
Cytoplasmic vesicle, phagosome 1 ELANE
spherical high-density lipoprotein particle 1 APOA1
glial cell projection 1 GLUL
endocytic vesicle lumen 1 APOA1
catalase complex 1 CAT
Weibel-Palade body 1 VWF
[Isoform H]: Cell membrane 1 ACHE
hippocampal mossy fiber expansion 1 MICAL1


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]
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  • 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]
  • Mayara Sandrielly Pereira Soares, Marcelo Zanusso Costa, Tatiane Morgana da Silva, Marta Gazal, Carlus Augustu Tavares do Couto, Gabriela Nogueira Debom, Rodrigo Rodrigues, Juliana Hofstätter Azambuja, Emerson André Casali, Cesar Eduardo Jacintho Moritz, Marta Frescura Duarte, Elizandra Braganhol, Francieli Moro Stefanello, Roselia Maria Spanevello. Methionine and/or Methionine Sulfoxide Alter Ectoenzymes Activities in Lymphocytes and Inflammatory Parameters in Serum from Young Rats: Acute and Chronic Effects. Cell biochemistry and biophysics. 2018 Jun; 76(1-2):243-253. doi: 10.1007/s12013-017-0815-4. [PMID: 28726179]
  • Ákos Kenéz, Tobias Warnken, Karsten Feige, Korinna Huber. Lower plasma trans-4-hydroxyproline and methionine sulfoxide levels are associated with insulin dysregulation in horses. BMC veterinary research. 2018 May; 14(1):146. doi: 10.1186/s12917-018-1479-z. [PMID: 29716602]
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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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  • 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]
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  • 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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  • Marcelo Zanusso Costa, Tatiane Morgana da Silva, Natália Porto Flores, Felipe Schmitz, Emilene Barros da Silva Scherer, Cassiana Macagnan Viau, Jenifer Saffi, Alethéa Gatto Barschak, Angela Terezinha de Souza Wyse, Roselia Maria Spanevello, Francieli Moro Stefanello. Methionine and methionine sulfoxide alter parameters of oxidative stress in the liver of young rats: in vitro and in vivo studies. Molecular and cellular biochemistry. 2013 Dec; 384(1-2):21-8. doi: 10.1007/s11010-013-1777-5. [PMID: 23963990]
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  • 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]
  • Andrzej Kozik, Anna Golda, Pawel Mak, Piotr Suder, Jerzy Silberring, Anna Barbasz, Maria Rapala-Kozik. Myeloperoxidase-catalyzed oxidative inactivation of human kininogens: the impairment of kinin-precursor and prekallikrein-binding functions. Biological chemistry. 2011 Mar; 392(3):263-74. doi: 10.1515/bc.2011.021. [PMID: 21194373]
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  • Maurizio Bruschi, Andrea Petretto, Giovanni Candiano, Luca Musante, Ezio Movilli, Laura Santucci, Andrea Urbani, Rosanna Gusmano, Enrico Verrina, Giovanni Cancarini, Francesco Scolari, Gian Marco Ghiggeri. Determination of the oxido-redox status of plasma albumin in hemodialysis patients. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Mar; 864(1-2):29-37. doi: 10.1016/j.jchromb.2008.01.035. [PMID: 18262857]
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