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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:31 UTC |
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Update Date | 2020-11-09 23:16:23 UTC |
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HMDB ID | HMDB0002005 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Methionine sulfoxide |
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Description | 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 is a very strong basic compound (based on its pKa). 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. |
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Structure | |
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Synonyms | Value | Source |
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L-Methionine sulfoxide | ChEBI | Methionine S-oxide | ChEBI | L-Methionine sulphoxide | Generator | Methionine sulphoxide | Generator | Methionine sulfoxide, (R-(r*,s*))-isomer | HMDB | Methionine sulfoxide, 35S-labeled, (+-)-isomer | HMDB | Methionine sulfoxide, (S-(r*,s*))-isomer | HMDB | Methionine sulfoxide, (2S)-isomer | HMDB | Methionine sulfoxide, (2R)-isomer | HMDB | Methionine sulfoxide, (+-)-isomer | HMDB | DL-Methionine sulfoxide | HMDB | L-Methionine S-oxide | HMDB | Methionine sulfoxide | HMDB |
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Chemical Formula | C5H11NO3S |
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Average Molecular Weight | 165.21 |
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Monoisotopic Molecular Weight | 165.045964392 |
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IUPAC Name | (2S)-2-amino-4-methanesulfinylbutanoic acid |
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Traditional Name | L-methionine sulfoxide |
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CAS Registry Number | 3226-65-1 |
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SMILES | CS(=O)CC[C@H](N)C(O)=O |
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InChI Identifier | InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10?/m0/s1 |
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InChI Key | QEFRNWWLZKMPFJ-YGVKFDHGSA-N |
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Chemical Taxonomy |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - L-alpha-amino acid
- Thia fatty acid
- Fatty acid
- Fatty acyl
- Sulfoxide
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Sulfinyl compound
- Carbonyl group
- Organic oxygen compound
- Organic nitrogen compound
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Amine
- Primary aliphatic amine
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 232 - 234 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-004i-0900000000-6639ef576db5a01f8ee5 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-004i-0910000000-4231d540eda02eebe871 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-004i-0900000000-f0849e8acf9a3e1e2763 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-004i-1910000000-b7a64800b9e577e219d4 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004i-1910000000-b7a64800b9e577e219d4 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004i-0900000000-a5138c4f03667c81645c | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004i-0910000000-b8f17a35f754f6a2adff | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004i-0900000000-40d23196cb4ee1cad23f | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-9400000000-cac8577601b69f1b723a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-43361da834d0b07907fd | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9000000000-6090b56aa5a22d72fb4f | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.30-1.40 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 4.0 (3.0-5.0) uM | Adult (>18 years old) | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 110 +/- 80 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 20 +/- 10 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.0444 +/- 0.0842 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 0.110 +/- 0.126 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 3.28 +/- 1.20 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.6418 +/- 0.4235 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.00-7.88 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.6-3.59 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 1.48 +/- 0.80 umol/mmol creatinine | Newborn (0-30 days old) | Female | Normal | | details | Urine | Detected and Quantified | 1.67 +/- 0.69 umol/mmol creatinine | Newborn (0-30 days old) | Male | Normal | | details | Urine | Detected and Quantified | < 0.132 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.31 (0.14-0.66) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected and Quantified | 0.5038 +/- 0.5427 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 0.4259 +/- 0.5426 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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Associated OMIM IDs | - 114500 (Colorectal cancer)
- 610247 (Eosinophilic esophagitis)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022789 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 139840 |
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KEGG Compound ID | C02989 |
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BioCyc ID | CPD0-1959 |
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BiGG ID | Not Available |
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Wikipedia Link | Methionine sulfoxide |
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METLIN ID | 6428 |
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PubChem Compound | 158980 |
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PDB ID | Not Available |
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ChEBI ID | 17016 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Schallreuter KU: Functioning methionine-S-sulfoxide reductases A and B are present in human skin. J Invest Dermatol. 2006 May;126(5):947-9. [PubMed:16619011 ]
- O'Donohue TL, Charlton CG, Thoa NB, Helke CJ, Moody TW, Pert A, Williams A, Miller RL, Jacobowitz DM: Release of alpha-melanocyte stimulating hormone into rat and human cerebrospinal fluid in vivo and from rat hypothalamus slices in vitro. Peptides. 1981 Spring;2(1):93-100. [PubMed:7243627 ]
- Boudier C, Cadene M, Bieth JG: Inhibition of neutrophil cathepsin G by oxidized mucus proteinase inhibitor. Effect of heparin. Biochemistry. 1999 Jun 29;38(26):8451-7. [PubMed:10387091 ]
- Mashima R, Nakanishi-Ueda T, Yamamoto Y: Simultaneous determination of methionine sulfoxide and methionine in blood plasma using gas chromatography-mass spectrometry. Anal Biochem. 2003 Feb 1;313(1):28-33. [PubMed:12576054 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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