S-methylmethionine

Also known as methylmethionine

'''S-Methylmethionine' (SMM) is a derivative of methionine with the chemical formula (CH3)2S+CH2CH2CH(NH3+)CO2−. This cation is a naturally-occurring intermediate in many biosynthetic pathways owing to the sulfonium functional group. It is biosynthesized from L-methionine and S-adenosylmethionine by the enzyme methionine S-methyltransferase. S''-methylmethionine is particularly abundant in plants, being more abundant than methionine.

Chemical data

Formula: C6H14NO2S+
Molecular weight: 164.25 g/mol
IUPAC name: (3-amino-3-carboxypropyl)-dimethylsulfanium
SMILES: C[S+](C)CCC(C(=O)O)N
InChIKey: YDBYJHTYSHBBAU-UHFFFAOYSA-O
XLogP: -3
Polar surface area: 64.3 Å²
H-bond donors: 2
H-bond acceptors: 3
Formal charge: 1

via PubChem

Research

310 papers

S-methylmethionine metabolism in Escherichia coli.Journal of bacteriology · 1999
S-methylmethionine ameliorates renal injury in diabetic mice by modulating macrophage inflammaging via ERK/NF-κb signaling pathway.International immunopharmacology · 2026
S-Methylmethionine (Vitamin U): A Critical Narrative Review of Pharmacological Mechanisms, Evidence Levels, and Translational Barriers.Pharmaceuticals (Basel, Switzerland) · 2026
S-Methylmethionine Effectively Alleviates Stress in Szarvasi-1 Energy Grass by Reducing Root-to-Shoot Cadmium Translocation.Plants (Basel, Switzerland) · 2022
Intake of S-Methylmethionine Alters Glucose Metabolism and Hepatic Gene Expression in C57BL/6J High-Fat-Fed Mice.Foods (Basel, Switzerland) · 2024

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Wikidata facts

Mass: 164.074525

Show 3 more facts

canonical SMILES: C[S+](C)CCC(C(=O)O)N
subject has role: vitamin
chemical formula: C₆H₁₄NO₂S⁺

Sources (2)

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Encyclopedic overview

4 sections

Contents

Biosynthesis and biochemical function
Beer flavor precursor in barley malt
References
External links

'''S-Methylmethionine' (SMM) is a derivative of methionine with the chemical formula (CH3)2S+CH2CH2CH(NH3+)CO2−. This cation is a naturally-occurring intermediate in many biosynthetic pathways owing to the sulfonium functional group. It is biosynthesized from L-methionine and S-adenosylmethionine by the enzyme methionine S-methyltransferase. S-methylmethionine is particularly abundant in plants, being more abundant than methionine.

S-Methylmethionine is sometimes referred to as vitamin U, but it is not considered a true vitamin. The term was coined in 1950 by Garnett Cheney for uncharacterized anti-ulcerogenic factors in raw cabbage juice that may help speed healing of peptic ulcers.

Excerpted from Wikipedia’s “S-methylmethionine” article, available under the CC BY-SA 4.0 licence.

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