1.0 2011-09-21 00:19:39 UTC 2025-11-19 02:42:31 UTC FDB022789 Methionine sulfoxide Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species via 2-electron-dependent mechanism. Such oxidants can be generated from activated neutrophils; therefore, methionine sulfoxide can be regarded as a biomarker of oxidative stress in vivo. (PMID 12576054) [HMDB]. Methionine sulfoxide is found in many foods, some of which are romaine lettuce, white cabbage, dill, and yellow bell pepper. 2-amino-4-(methylsulfinyl)-Butanoate 2-amino-4-(methylsulfinyl)-Butanoic acid alpha-amino-gamma-(methylsulfinyl)-Butyric acid DL-Methionine sulfoxide L-methionine (S)-S-oxide L-methionine R-oxide L-Methionine sulfoxide Met-so Methionine sulphoxide S-oxide-methionine C5H11NO3S 165.211 165.045963913 2-amino-4-methanesulfinylbutanoic acid DL-methionine sulfoxide 62697-73-8 CS(=O)CCC(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) QEFRNWWLZKMPFJ-UHFFFAOYSA-N belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Alpha amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Sulfinyl compounds Sulfoxides Thia fatty acids Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Fatty acid Fatty acyl Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Sulfinyl compound Sulfoxide Thia fatty acid S-oxide a small molecule methionine derivative Solid 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 2-amino-4-methanesulfinylbutanoic acid ChemAxon average_mass 165.211 ChemAxon mono_mass 165.045963913 ChemAxon smiles CS(=O)CCC(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) ChemAxon inchikey QEFRNWWLZKMPFJ-UHFFFAOYSA-N ChemAxon polar_surface_area 80.39 ChemAxon refractivity 39.34 ChemAxon polarizability 16.04 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Methionine Metabolism SMP00033 map00270 Specdb::NmrTwoD 1774 Specdb::NmrOneD 1834 Specdb::NmrOneD 4847 Specdb::NmrOneD 4848 Specdb::MsMs 1941 Specdb::MsMs 1942 Specdb::MsMs 1943 Specdb::MsMs 179766 Specdb::MsMs 179767 Specdb::MsMs 179768 Specdb::MsMs 182100 Specdb::MsMs 182101 Specdb::MsMs 182102 Specdb::MsMs 2231963 Specdb::MsMs 2232206 Specdb::MsMs 2234397 Specdb::MsMs 2234561 Specdb::MsMs 3426738 Specdb::MsMs 3426739 Specdb::MsMs 3426740 Specdb::MsMs 3426741 Specdb::MsMs 3426742 Specdb::MsMs 3426743 Specdb::CMs 799 Specdb::CMs 800 Specdb::CMs 801 Specdb::CMs 1434 Specdb::CMs 21006 Specdb::CMs 31380 Specdb::CMs 32238 Specdb::CMs 32239 Specdb::CMs 32240 Specdb::CMs 38219 Specdb::CMs 118877 Specdb::CMs 123499 Specdb::CMs 126135 Specdb::CMs 868377 Specdb::CMs 868378 Specdb::CMs 868379 HMDB02005 #<Reference:0x00005636d172a6b0> #<Reference:0x00005636d172a4f8> #<Reference:0x00005636d172a340> #<Reference:0x00005636d172a188> Anatidae Type 1 specific Anatidae 8830 Barley Type 1 specific Hordeum vulgare 4513 11.321691 11.32338202 11.32 mg/100 g Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Broccoli Type 1 specific Brassica oleracea var. italica 36774 1.84 1.84 1.84 mg/100 g Buffalo Type 1 specific Bubalus bubalis 89462 Carrot Type 1 specific Daucus carota ssp. sativus 79200 0.38 0.38 0.38 mg/100 g Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columba 8930 Cucumber Type 1 specific Cucumis sativus 3659 0.73 0.73 0.73 mg/100 g Deer Type 1 specific Cervidae 9850 Dill Type 1 specific Anethum graveolens 40922 1.68 1.68 1.68 mg/100 g Domestic goat Type 1 Animal Capra aegagrus hircus 9925 Domestic pig Type 1 Animal Sus scrofa domesticus 9825 Eggplant Type 1 specific Solanum melongena 4111 0.03 0.03 0.03 mg/100 g Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus cuniculus 9984 Garden onion Type 1 specific Allium cepa 4679 0.18 0.18 0.18 mg/100 g Green bean Type 1 specific Phaseolus vulgaris 3885 2.22 2.22 2.22 mg/100 g Green bell pepper Type 1 specific Capsicum annuum 4072 0.1 0.1 0.1 mg/100 g Green zucchini Type 1 specific Cucurbita pepo var. cylindrica 1.05 1.05 1.05 mg/100 g Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Japanese pumpkin Type 1 specific Cucurbita maxima 3661 0.53 0.53 0.53 mg/100 g Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus hemionus 9871 Orange bell pepper Type 1 specific Capsicum annuum 4072 0.8 0.8 0.8 mg/100 g Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Potato Type 1 specific Solanum tuberosum 4113 0.5 0.5 0.5 mg/100 g Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Red beetroot Type 1 specific Beta vulgaris var. rubra 1.06 1.06 1.06 mg/100 g Red bell pepper Type 1 specific Capsicum annuum 4072 0.479989 0.48 0.479978526 mg/100 g Rock ptarmigan Type 1 specific Lagopus muta 64668 Romaine lettuce Type 1 specific Lactuca sativa L. var. longifolia 0.2 0.2 0.2 mg/100 g Saskatoon berry Type 1 specific Amelanchier alnifolia 32219 0.2 0.2 0.2 mg/100 g Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Spinach Type 1 specific Spinacia oleracea 3562 0.48 0.48 0.48 mg/100 g Squab Type 1 specific Columba 8931 Sunburst squash (pattypan squash) Type 1 specific Cucurbita pepo var. clypeata 0.84 0.84 0.84 mg/100 g Swiss chard Type 1 specific Beta vulgaris ssp. cicla 1527200 1.349862 1.35 1.34972373 mg/100 g Turkey Type 1 specific Meleagris gallopavo 9103 Turnip Type 1 specific Brassica rapa var. rapa 51350 0.19 0.19 0.19 mg/100 g Velvet duck Type 1 specific Melanitta fusca 371864 White cabbage Type 1 specific Brassica oleracea L. var. capitata L. f. alba DC. 0.64 0.64 0.64 mg/100 g Wild boar Type 1 specific Sus scrofa 9823 Yellow bell pepper Type 1 specific Capsicum annuum 4072 0.58 0.58 0.58 mg/100 g Yellow wax bean Type 1 specific Phaseolus vulgaris 3885 1.3 1.3 1.3 mg/100 g Yellow zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.61 0.61 0.61 mg/100 g Methionine-R-sulfoxide reductase B2, mitochondrial Q9Y3D2 MSRB2 Methionine-R-sulfoxide reductase B3 Q8IXL7 MSRB3 Mitochondrial peptide methionine sulfoxide reductase Q9UJ68 MSRA