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Identification
YMDB IDYMDB00035
NameL-methionine (R)-S-oxide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Methionine (R)-S-oxide, also known as l-methionine (r)-s-oxide, 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. L-Methionine (R)-S-oxide is possibly soluble (in water) and a very strong basic compound (based on its pKa). L-Methionine (R)-S-oxide exists in both E.coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • 2-amino-4-(methylsulfinyl)-Butanoate
  • 2-amino-4-(methylsulfinyl)-Butanoic acid
  • alpha-amino-gamma-(methylsulfinyl)-Butyric acid
  • DL-Methionine sulfoxide
  • L-Methionine (R)-S-oxide
  • L-methionine (S)-S-oxide
  • L-methionine R-oxide
  • L-Methionine sulfoxide
  • L-Methionine-R-sulfoxide
  • L-Methionine-R-sulphoxide
  • Peptide-L-methionine (R)-S-oxide
  • S-oxide-methionine
  • Methionine sulfoxide, (+-)-isomer
  • Methionine sulfoxide, (2R)-isomer
  • Methionine sulfoxide, (2S)-isomer
  • Methionine sulfoxide, (S-(r*,s*))-isomer
  • Methionine sulfoxide, 35S-labeled, (+-)-isomer
  • Methionine sulfoxide
  • Methionine sulfoxide, (R-(r*,s*))-isomer
CAS number62697-73-8
WeightAverage: 165.211
Monoisotopic: 165.045963913
InChI KeyQEFRNWWLZKMPFJ-ZXPFJRLXSA-N
InChIInChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10+/m0/s1
IUPAC Name(2S)-2-amino-4-[(R)-methanesulfinyl]butanoic acid
Traditional IUPAC NameL-methionine (R)-S-oxide
Chemical FormulaC5H11NO3S
SMILESC[S@@](=O)CC[C@H](N)C(O)=O
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
StateSolid
Charge0
Melting point232 - 234 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Polarizability16.08 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
93 ± 5 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID49032
HMDB IDHMDB02005
Pubchem Compound ID10062737
Kegg IDC15653
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDL-METHIONINE_SULFOXIDE

Enzymes

General function:
Involved in protein binding
Specific function:
Catalyzes the reversible oxidation-reduction of the R- enantiomer of free methionine sulfoxide to methionine. Does not act on S-enantiomer of free methionine sulfoxide or R-enantiomer of dabsylated methionine sulfoxide. Involved in protection against oxidative stress
Gene Name:
Not Available
Uniprot ID:
P36088
Molecular weight:
19734.19922
Reactions
L-methionine + thioredoxin disulfide + H(2)O → L-methionine (R)-S-oxide + thioredoxin.
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. Also able to reduce dimethyl sulfoxide (DMSO) as well, with DMS as the product
Gene Name:
MXR1
Uniprot ID:
P40029
Molecular weight:
21140.69922
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.