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Record Information
Version	2.0
Creation Date	2012-05-31 14:37:45 -0600
Update Date	2015-06-03 17:19:43 -0600
Secondary Accession Numbers	ECMDB20295
Identification
Name:	L-Methionine-(S)-S-oxide
Description	L-methionine-(s)-s-oxide is an oxidized form of methionine. Methionine is an amino acid susceptible to being oxidized to methionine sulfoxide (MetSO). The reduction of MetSO to methionine is catalyzed by methionine sulfoxide reductase (MSR), an enzyme present in almost all organisms. (PMID 20969952) Oxidation of methionine to methionine sulfoxide is a major oxidative stress product that reaches levels as high as 60% in cataract while being essentially absent from clear lenses. Methionine oxidation results in loss of protein function that can be reversed through the action of methionine sulfoxide reductase A (MsrA), which is implicated in oxidative stress protection and is an essential regulator of longevity in species ranging from Escherichia coli to mice. (PMID 15199188)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xad76e2e4> Close
Synonyms:	2-Amino-4-(methylsulfinyl)-Butanoate 2-Amino-4-(methylsulfinyl)-Butanoic acid 2-Amino-4-(methylsulfinyl)-Butyrate 2-Amino-4-(methylsulfinyl)-Butyric acid 2-Amino-4-(methylsulfinyl)butanoate 2-Amino-4-(methylsulfinyl)butanoic acid 2-Amino-4-(methylsulphinyl)-Butanoate 2-Amino-4-(methylsulphinyl)-Butanoic acid 2-Amino-4-(methylsulphinyl)-Butyrate 2-Amino-4-(methylsulphinyl)-Butyric acid 2-Amino-4-(methylsulphinyl)butanoate 2-Amino-4-(methylsulphinyl)butanoic acid DL-methionine sulfoxide DL-methionine sulphoxide L-Methionine (S)-S-oxide Methionine S-oxide Methionine sulfoxide Methionine sulphoxide Methionine, S-oxide
Chemical Formula:	C5H11NO3S
Weight:	Average: 165.211 Monoisotopic: 165.045963913
InChI Key:	QEFRNWWLZKMPFJ-KNODYTOMSA-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+/m1/s1
CAS number:	454-41-1
IUPAC Name:	(2R)-2-amino-4-[(S)-methanesulfinyl]butanoic acid
Traditional IUPAC Name:	methionine sulfoxide
SMILES:	C[S@](=O)CC[C@@H](N)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-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	D-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	D-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	D-methionine S-oxide (CHEBI:49036 )
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 16.07 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:
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 (TMS_3_1) - 70eV, Positive Not Available View in JSpectraViewer 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 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 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:	Arias, D. G., Cabeza, M. S., Erben, E. D., Carranza, P. G., Lujan, H. D., Tellez Inon, M. T., Iglesias, A. A., Guerrero, S. A. (2011). "Functional characterization of methionine sulfoxide reductase A from Trypanosoma spp." Free Radic Biol Med 50:37-46. Pubmed: 20969952 Kantorow, M., Hawse, J. R., Cowell, T. L., Benhamed, S., Pizarro, G. O., Reddy, V. N., Hejtmancik, J. F. (2004). "Methionine sulfoxide reductase A is important for lens cell viability and resistance to oxidative stress." Proc Natl Acad Sci U S A 101:9654-9659. Pubmed: 15199188 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 49036 HMDB ID Not Available Pubchem Compound ID 11869258 Kegg ID Not Available ChemSpider ID 7851532 Wikipedia ID Not Available BioCyc ID CPD0-1959 EcoCyc ID CPD0-1959

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