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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:31 UTC
Update Date2020-02-27 16:50:44 UTC
HMDB IDHMDB0002005
Secondary Accession Numbers
  • HMDB02005
Metabolite Identification
Common NameMethionine sulfoxide
DescriptionMethionine 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.
Structure
Data?1582752222
Synonyms
ValueSource
L-Methionine sulfoxideChEBI
Methionine S-oxideChEBI
L-Methionine sulphoxideGenerator
Methionine sulphoxideGenerator
Methionine sulfoxide, (R-(r*,s*))-isomerHMDB
Methionine sulfoxide, 35S-labeled, (+-)-isomerHMDB
Methionine sulfoxide, (S-(r*,s*))-isomerHMDB
Methionine sulfoxide, (2S)-isomerHMDB
Methionine sulfoxide, (2R)-isomerHMDB
Methionine sulfoxide, (+-)-isomerHMDB
DL-Methionine sulfoxideHMDB
L-Methionine S-oxideHMDB
Methionine sulfoxideHMDB
Chemical FormulaC5H11NO3S
Average Molecular Weight165.21
Monoisotopic Molecular Weight165.045964392
IUPAC Name(2S)-2-amino-4-methanesulfinylbutanoic acid
Traditional NameL-methionine sulfoxide
CAS Registry Number3226-65-1
SMILES
CS(=O)CC[C@H](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)/t4-,10?/m0/s1
InChI KeyQEFRNWWLZKMPFJ-YGVKFDHGSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
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
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
Polarizability15.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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-0900000000-6639ef576db5a01f8ee5Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0910000000-4231d540eda02eebe871Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0900000000-f0849e8acf9a3e1e2763Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-1910000000-b7a64800b9e577e219d4Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-1910000000-b7a64800b9e577e219d4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-a5138c4f03667c81645cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0910000000-b8f17a35f754f6a2adffSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-40d23196cb4ee1cad23fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9400000000-cac8577601b69f1b723aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-43361da834d0b07907fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-6090b56aa5a22d72fb4fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Epidermis
  • Placenta
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 Quantified0.6-3.59 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
details
UrineDetected and Quantified1.48 +/- 0.80 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
details
UrineDetected and Quantified1.67 +/- 0.69 umol/mmol creatinineNewborn (0-30 days old)MaleNormal
    • López Hernández Y...
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 ID139840
    KEGG Compound IDC02989
    BioCyc IDCPD0-1959
    BiGG IDNot Available
    Wikipedia LinkMethionine sulfoxide
    METLIN ID6428
    PubChem Compound158980
    PDB IDNot Available
    ChEBI ID17016
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    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 ]
    5. 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 ]

    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