L-methionine (S)-S-oxide (ECMDB23117) (M2MDB003507)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (3)
Record Information
Version2.0
Creation Date2012-10-10 12:17:20 -0600
Update Date2015-08-05 16:22:04 -0600
Secondary Accession Numbers
  • ECMDB23117
Identification
Name:L-methionine (S)-S-oxide
DescriptionThe (S)-oxido diastereomer of L-methionine S-oxide
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:Not Available
Chemical Formula:C5H11NO3S
Weight:Average: 165.211
Monoisotopic: 165.045963913
InChI Key:QEFRNWWLZKMPFJ-MFXDVPHUSA-N
InChI: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
CAS number:62697-73-8
IUPAC Name:(2S)-2-azaniumyl-4-[(S)-methanesulfinyl]butanoate
Traditional IUPAC Name:L-methionine (S)-S-oxide
SMILES:[H]C([H])([H])[S@](=O)C([H])([H])C([H])([H])[C@@]([H])(C([O-])=O)[N+]([H])([H])[H]
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
Physical Properties
State:Solid
Charge:0
Melting point:232 - 234 C
Experimental Properties:
PropertyValueSource
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 Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area84.84 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity61.47 m³·mol⁻¹ChemAxon
Polarizability16.12 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
L-Methionine + thioredoxin disulfide + Water > L-methionine (S)-S-oxide + thioredoxin
Peptide-L-methionine + Thioredoxin disulfide + Water + L-Methionine <> Peptide-L-methionine (S)-S-oxide + Thioredoxin + L-methionine (S)-S-oxide
Peptide-L-methionine + Thioredoxin disulfide + Water + L-Methionine <> Peptide-L-methionine (S)-S-oxide + Thioredoxin + L-methionine (S)-S-oxide
Peptide-L-methionine + Thioredoxin disulfide + Water + L-Methionine <> Peptide-L-methionine (S)-S-oxide + Thioredoxin + L-methionine (S)-S-oxide
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-e7bc579a824be638d903View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-1900000000-ebae7e61304a209031d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdr-9200000000-9fc62c104f3aadaf5757View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-6900000000-aa5b1f46132bedab582cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-4d3484be45dac57dd1f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-48732057ccfafc8108fcView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID49033
HMDB IDHMDB02005
Pubchem Compound ID847
Kegg IDC15999
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDL-METHIONINE_SULFOXIDE
EcoCyc IDL-METHIONINE_SULFOXIDE
Ligand ExpoMHO

Enzymes

Protein Details
1. Peptide methionine sulfoxide reductase msrA
General function:
Involved in oxidoreductase activity, acting on a sulfur group of donors, disulfide as acceptor
Specific function:
Could have 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:
P0A744
Molecular weight:
23315
Reactions
Peptide-L-methionine + thioredoxin disulfide + H(2)O = peptide-L-methionine (S)-S-oxide + thioredoxin.
L-methionine + thioredoxin disulfide + H(2)O = L-methionine (S)-S-oxide + thioredoxin.