L-methionine (R)-S-oxide (YMDB00035)

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Identification

YMDB ID

YMDB00035

Name

L-methionine (R)-S-oxide

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

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 a very strong basic compound (based on its pKa). L-methionine (R)-S-oxide exists in both E. coli (prokaryote) and yeast (eukaryote).

Structure

MOL SDF PDB SMILES InChI

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 number

62697-73-8

Weight

Average: 165.211
Monoisotopic: 165.045963913

InChI Key

QEFRNWWLZKMPFJ-ZXPFJRLXSA-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

IUPAC Name

(2S)-2-amino-4-[(R)-methanesulfinyl]butanoic acid

Traditional IUPAC Name

L-methionine (R)-S-oxide

Chemical Formula

C₅H₁₁NO₃S

SMILES

C[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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-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 Framework

Aliphatic acyclic compounds

External Descriptors

L-methionine S-oxide (CHEBI:49032 )

Physical Properties

State

Solid

Charge

Melting point

232 - 234 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	54 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4.6	ChemAxon
logS	-0.49	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	39.34 m³·mol⁻¹	ChemAxon
Polarizability	16.08 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Cytoplasm
Nucleus

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
93 ± 5 µM	YEB media with 0.5 mM glucose	aerobic	Baker's yeast	Experimentally Determined Not Available
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0r93-9300000000-b6718d881d99e12ff759	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xs-1900000000-fcc67db2a5a5bf8ca7d1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-3900000000-34d83116882727d02c7c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-46769789e14fd087cf4f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9600000000-d08eb17f57c92e0b6177	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-61c3a03a3376f6fb1199	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-dc00833494588ecbc224	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	49032
HMDB ID	HMDB02005
Pubchem Compound ID	10062737
Kegg ID	C15653
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	L-METHIONINE_SULFOXIDE

Enzymes

Protein Details

1. Free methionine-R-sulfoxide reductase

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.

Protein Details

2. Peptide methionine sulfoxide reductase

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.

Structure for #<Compound:0xa4fcfa04>

Enzymes

Reactions

Reactions