2.0 2012-05-31 14:37:45 -0600 2015-06-03 17:19:43 -0600 ECMDB20295 M2MDB001133 L-Methionine-(S)-S-oxide 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) 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 C5H11NO3S 165.211 165.045963913 (2R)-2-amino-4-[(S)-methanesulfinyl]butanoic acid methionine sulfoxide 454-41-1 C[S@](=O)CC[C@@H](N)C(O)=O 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 QEFRNWWLZKMPFJ-KNODYTOMSA-N Cytoplasm Periplasm logp -2.40 ALOGPS logs -0.49 ALOGPS solubility 5.40e+01 g/l ALOGPS logp -4.6 ChemAxon pka_strongest_acidic 1.74 ChemAxon pka_strongest_basic 9.11 ChemAxon iupac (2R)-2-amino-4-[(S)-methanesulfinyl]butanoic acid ChemAxon average_mass 165.211 ChemAxon mono_mass 165.045963913 ChemAxon smiles C[S@](=O)CC[C@@H](N)C(O)=O ChemAxon formula C5H11NO3S ChemAxon 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 ChemAxon inchikey QEFRNWWLZKMPFJ-KNODYTOMSA-N ChemAxon polar_surface_area 80.39 ChemAxon refractivity 39.34 ChemAxon polarizability 16.07 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1087649 Specdb::NmrOneD 290995 Specdb::NmrOneD 290996 Specdb::NmrOneD 290997 Specdb::NmrOneD 290998 Specdb::NmrOneD 290999 Specdb::NmrOneD 291000 Specdb::NmrOneD 291001 Specdb::NmrOneD 291002 Specdb::NmrOneD 291003 Specdb::NmrOneD 291004 Specdb::NmrOneD 291005 Specdb::NmrOneD 291006 Specdb::NmrOneD 291007 Specdb::NmrOneD 291008 Specdb::NmrOneD 291009 Specdb::NmrOneD 291010 Specdb::NmrOneD 291011 Specdb::NmrOneD 291012 Specdb::NmrOneD 291013 Specdb::NmrOneD 291014 Specdb::MsMs 27908 Specdb::MsMs 27909 Specdb::MsMs 27910 Specdb::MsMs 34466 Specdb::MsMs 34467 Specdb::MsMs 34468 11869258 7851532 CPD0-1959 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. 21097882 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. 15199188 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. 20969952 Peptide methionine sulfoxide reductase msrA P0A744 MSRA_ECOLI msrA http://ecmdb.ca/proteins/P0A744.xml Peptide methionine sulfoxide reductase msrB P0A746 MSRB_ECOLI msrB http://ecmdb.ca/proteins/P0A746.xml