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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:31 UTC
Update Date2019-03-14 18:02:17 UTC
HMDB IDHMDB0002005
Secondary Accession Numbers
  • HMDB02005
Metabolite Identification
Common NameMethionine sulfoxide
DescriptionMethionine 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 ).
Structure
Data?1547234190
Synonyms
ValueSource
Methionine sulphoxideGenerator
2-Amino-4-(methylsulfinyl)-butanoateHMDB
2-Amino-4-(methylsulfinyl)-butanoic acidHMDB
alpha-Amino-gamma-(methylsulfinyl)-butyric acidHMDB
DL-Methionine sulfoxideHMDB
L-Methionine (S)-S-oxideHMDB
L-Methionine R-oxideHMDB
L-Methionine sulfoxideHMDB
Met-soHMDB
S-Oxide-methionineHMDB
Methionine sulfoxide, (2S)-isomerHMDB
Methionine sulfoxide, (R-(r*,s*))-isomerHMDB
Methionine sulfoxide, (+-)-isomerHMDB
Methionine sulfoxide, (2R)-isomerHMDB
Methionine sulfoxide, (S-(r*,s*))-isomerHMDB
Methionine sulfoxide, 35S-labeled, (+-)-isomerHMDB
Chemical FormulaC5H11NO3S
Average Molecular Weight165.211
Monoisotopic Molecular Weight165.045963913
IUPAC Name2-amino-4-methanesulfinylbutanoic acid
Traditional NameDL-methionine sulfoxide
CAS Registry Number62697-73-8
SMILES
CS(=O)CCC(N)C(O)=O
InChI Identifier
InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)
InChI KeyQEFRNWWLZKMPFJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Thia fatty acid
  • Fatty acyl
  • Fatty acid
  • Sulfoxide
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfinyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point232 - 234 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility54 g/LALOGPS
logP-2.4ALOGPS
logP-4.6ChemAxon
logS-0.49ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.34 m³·mol⁻¹ChemAxon
Polarizability16.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0900000000-6639ef576db5a01f8ee5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0910000000-4231d540eda02eebe871JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0900000000-f0849e8acf9a3e1e2763JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-1910000000-b7a64800b9e577e219d4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-1910000000-b7a64800b9e577e219d4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-a5138c4f03667c81645cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0910000000-b8f17a35f754f6a2adffJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-40d23196cb4ee1cad23fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kmi-9300000000-40502e78936db0335f4aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fs-9600000000-b39ca26ddac3482e7cc5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9400000000-cac8577601b69f1b723aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-43361da834d0b07907fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-6090b56aa5a22d72fb4fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-1900000000-f7bdaacb8f4c8c0ecac8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-3900000000-0dbf2b087d6505b4b820JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-00dc8b47e3cb0dc2e321JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9600000000-9032163b7ca7799d7c43JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-562e35acb4f9e5564a69JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-2125dfc28681bc1d4c2eJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.30-1.40 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified4.0 (3.0-5.0) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified110 +/- 80 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified20 +/- 10 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.0444 +/- 0.0842 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.110 +/- 0.126 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified3.28 +/- 1.20 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.6418 +/- 0.4235 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.00-7.88 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified< 0.132 umol/mmol creatinineAdult (>18 years old)BothNormal
    details
    UrineDetected and Quantified0.31 (0.14-0.66) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    UrineDetected and Quantified0.5038 +/- 0.5427 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified0.4259 +/- 0.5426 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • Mordechai, Hien, ...
    details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. 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 ]
    2. 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 ]
    3. 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
    1. (). Mordechai, Hien, and David S. Wishart. .
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022789
    KNApSAcK IDNot Available
    Chemspider ID824
    KEGG Compound IDNot Available
    BioCyc IDCPD0-1959
    BiGG IDNot Available
    Wikipedia LinkMethionine sulfoxide
    METLIN ID6428
    PubChem Compound847
    PDB IDNot Available
    ChEBI ID49033
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. 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 ]
    2. 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 ]
    3. 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 ]
    4. 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 ]

    Enzymes

    General function:
    Involved in oxidoreductase activity, acting on a sulfur group of donors, disulfide as acceptor
    Specific function:
    Has an important function as a repair enzyme for proteins that have been inactivated by oxidation. Catalyzes the reversible oxidation-reduction of methionine sulfoxide in proteins to methionine.
    Gene Name:
    MSRA
    Uniprot ID:
    Q9UJ68
    Molecular weight:
    21737.41
    Reactions
    L-Methionine + thioredoxin disulfide + Water → Methionine sulfoxide + thioredoxindetails
    General function:
    Involved in peptide-methionine-(S)-S-oxide reductase activity
    Specific function:
    Catalyzes the reduction of free and protein-bound methionine sulfoxide to methionine (By similarity). Upon oxidative stress, may play a role in the preservation of mitochondrial integrity by decreasing the intracellular reactive oxygen species build-up through its scavenging role, hence contributing to cell survival and protein maintenance.
    Gene Name:
    MSRB2
    Uniprot ID:
    Q9Y3D2
    Molecular weight:
    19536.055
    General function:
    Involved in peptide-methionine-(S)-S-oxide reductase activity
    Specific function:
    Catalyzes the reduction of free and protein-bound methionine sulfoxide to methionine. Isoform 2 is essential for hearing.
    Gene Name:
    MSRB3
    Uniprot ID:
    Q8IXL7
    Molecular weight:
    20010.23