S-Methylcysteine is the amino acid with the nominal formula CH3SCH2CH(NH2)CO2H. It is the S-methylated derivative of cysteine. This amino acid occurs widely in plants, including many edible vegetables.[1]
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IUPAC name
S-Methyl-L-cysteine
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Systematic IUPAC name
2-amino-3-(methylthio)propanoic acid | |
Other names
3-methylthioalanine
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Identifiers | |
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3D model (JSmol)
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ChEBI |
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ChEMBL |
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ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.013.365 |
EC Number |
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KEGG |
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PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C4H9NO2S | |
Molar mass | 135.18 g·mol−1 |
Appearance | white solid |
Melting point | 248 °C (478 °F; 521 K) |
Hazards | |
GHS labelling: | |
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H302, H315, H319, H335 | |
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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The amino acid is not genetically coded, but it arises by post-translational methylation of cysteine. One pathway involves methyl transfer from alkylated DNA by zinc-cysteinate-containing repair enzymes.[2][3]
Beyond its biological context, it has been examined as a chelating agent.[4]