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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-12 00:00:09 UTC
Update Date2019-07-23 06:27:17 UTC
HMDB IDHMDB0038670
Secondary Accession Numbers
  • HMDB38670
Metabolite Identification
Common NameS-Methylmethionine
DescriptionS-Methylmethionine, also known as vitamin u, belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. S-Methylmethionine is sometimes referred to as vitamin U, but it is not considered a true vitamin. Lightly kilned malts such as pilsner or lager malts retain much of their SMM content while higher kilned malt such as pale ale malt has substantially more of the SMM converted to DMS in the malt. S-Methylmethionine is a very strong basic compound (based on its pKa). Outside of the human body, S-Methylmethionine is found, on average, in the highest concentration within tea and garden tomato (var.). S-Methylmethionine has also been detected, but not quantified in, several different foods, such as yardlong beans, chicory leaves, daikon radish, pistachio, and spearmints. This could make S-methylmethionine a potential biomarker for the consumption of these foods. S-Methylmethionine is claimed to have protective effects in the gastrointestinal mucosa and in the liver. Darker kilned malts such as Munich malt have virtually no SMM content since most has been converted to DMS. The coproduct is S-adenosyl homocysteine. A few plants use S-methylmethionine as a precursor to the osmolyte dimethylsulfoniopropionate (DMSP).
Structure
Data?1563863237
Synonyms
ValueSource
(3-Amino-3-carboxypropyl)dimethylsulfonium(1+), 9ci, 8ciHMDB
S-Methyl-L-methionineHMDB
Chloride, methionine methylsulfoniumHMDB
Methionine methylsulfonium chlorideHMDB
MethylmethionineHMDB
Methylmethionine sulfonium chlorideHMDB
Methylsulfonium chloride, methionineHMDB
S MethylmethionineHMDB
Chloride, methylmethioninesulfoniumHMDB
Sulfonium, ((3S)-3-amino-3-carboxypropyl)dimethyl-, inner saltHMDB
Methylmethioninesulfonium chlorideHMDB
Vitamin uHMDB
Chemical FormulaC6H14NO2S
Average Molecular Weight164.246
Monoisotopic Molecular Weight164.074524387
IUPAC Name(3-amino-3-carboxypropyl)dimethylsulfanium
Traditional NameS-methylmethionine
CAS Registry Number13065-25-3
SMILES
C[S+](C)CCC(N)C(O)=O
InChI Identifier
InChI=1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1
InChI KeyYDBYJHTYSHBBAU-UHFFFAOYSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentMethionine and derivatives
Alternative Parents
Substituents
  • Methionine or derivatives
  • Alpha-amino acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point139 °C (decomposition)Not Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.12 g/LALOGPS
logP-1.3ALOGPS
logP-3.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.24ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.1 m³·mol⁻¹ChemAxon
Polarizability17.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xr-9600000000-31877974a2a73693c8d9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0629-9400000000-f82a0c4d166de3a4966bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-0900000000-1c593a8242fb277a76aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-8900000000-586659c7bdf583fdac59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vi-9100000000-7536d21f47277c6d682fSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018070
KNApSAcK IDNot Available
Chemspider ID445
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkS-Methylmethionine
METLIN IDNot Available
PubChem Compound458
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDMMET
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .