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Record Information
Version	2.0
Creation Date	2012-10-10 12:17:18 -0600
Update Date	2015-06-03 17:25:57 -0600
Secondary Accession Numbers	ECMDB23116
Identification
Name:	L-Methionine (R)-S-oxide
Description	L-Methionine (R)-S-oxide or Met-(R)-O is an oxidized form of methionine. It can be used as a substrate for growth by E. coli. It is known that Escherichia coli methionine mutants can grow on both enantiomers of methionine sulfoxide (met(o)), i.e., Met-R-(O) or Met-S-(O), indicating the presence of enzymes in E. coli that can reduce each of these enantiomers to methionine (met). Recently it was discovered that an enzyme known as fRMsr or L-methionine (R)-S-oxide reductase (EC 1.8.4.14) is the enzyme that catalyzes the chemical reaction L-methionine + thioredoxin disulfide + H2O <=> L-methionine (R)-S-oxide + thioredoxin. It is thought that Met-(R)-O may represent a signaling molecule in response to oxidative stress. [PMID:17535911]
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb0156e1c> Close
Synonyms:	(2S)-2-amino-4-(R)-Methylsulfinylbutanoate (2S)-2-Amino-4-(R)-methylsulfinylbutanoic acid (2S)-2-amino-4-(R)-Methylsulphinylbutanoate (2S)-2-amino-4-(R)-Methylsulphinylbutanoic acid
Chemical Formula:	C5H11NO3S
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
CAS number:	Not Available
IUPAC Name:	(2S)-2-amino-4-[(R)-methanesulfinyl]butanoic acid
Traditional IUPAC Name:	L-methionine (R)-S-oxide
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	Thia fatty acids Sulfoxides Amino acids Sulfinyl compounds Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
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:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
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 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 39.34 m³·mol⁻¹ ChemAxon Polarizability 16.08 ų 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
Reactions:	L-Methionine + thioredoxin disulfide + Water > L-Methionine (R)-S-oxide + thioredoxin
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0r93-9300000000-b6718d881d99e12ff759 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00xs-1900000000-fcc67db2a5a5bf8ca7d1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0fk9-3900000000-34d83116882727d02c7c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9000000000-46769789e14fd087cf4f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-9600000000-d08eb17f57c92e0b6177 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03di-9000000000-61c3a03a3376f6fb1199 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-03di-9000000000-dc00833494588ecbc224 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 49032 HMDB ID Not Available Pubchem Compound ID 10062737 Kegg ID C15998 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available Ligand Expo SME