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Record Information
Version3.6
Creation Date2006-05-22 14:17:31 UTC
Update Date2016-03-21 21:02:51 UTC
HMDB IDHMDB02005
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
Methionine sulfoxideChEBI
Methionine sulphoxideGenerator
2-amino-4-MethylsulfinylbutanoateGenerator
2-amino-4-MethylsulphinylbutanoateGenerator
2-amino-4-Methylsulphinylbutanoic acidGenerator
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
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 KeyInChIKey=QEFRNWWLZKMPFJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Sulfoxide
  • Sulfinyl compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility54.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.34 m3·mol-1ChemAxon
Polarizability16.04 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-004i-0900000000-6639ef576db5a01f8ee5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-004i-0910000000-4231d540eda02eebe871View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-004i-0900000000-f0849e8acf9a3e1e2763View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-1910000000-b7a64800b9e577e219d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9400000000-cac8577601b69f1b723aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-43361da834d0b07907fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-6090b56aa5a22d72fb4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Epidermis
Pathways
NameSMPDB LinkKEGG Link
Cystathionine Beta-Synthase DeficiencySMP00177Not Available
Glycine N-methyltransferase DeficiencySMP00222Not Available
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeSMP00570Not Available
HypermethioninemiaSMP00341Not Available
Methionine Adenosyltransferase DeficiencySMP00221Not Available
Methionine MetabolismSMP00033map00270
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)SMP00340Not Available
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencySMP00214Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.0 (3.0-5.0) uMAdult (>18 years old)Not SpecifiedNormal 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
    BiofluidStatusValueAgeSexConditionReferenceDetails
    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 ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022789
    KNApSAcK IDNot Available
    Chemspider ID824
    KEGG Compound IDNot Available
    BioCyc IDL-METHIONINE_SULFOXIDE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB02005
    Metagene LinkHMDB02005
    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. [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. [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. [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. [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