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
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:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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

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.