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Record Information
Version2.0
Creation Date2012-07-30 14:55:31 -0600
Update Date2015-10-23 17:32:16 -0600
Secondary Accession Numbers
  • ECMDB21377
Identification
Name:S-Methylmethionine
DescriptionS-methylmethionine can be used by E coli as a source of methionine. It is taken up from the environment via the methionine update system or a S-methylmethionine permiase, and converted to methionine inside the cell. This has especially been observed under methionine auxotrophic conditions. (PMID: 9882684)
Structure
Thumb
Synonyms:
  • [Cytochrome c] S-methyl-L-methionine
  • [Cytochrome c] S-methylmethionine
Chemical Formula:C6H14NO2S
Weight:Average: 164.246
Monoisotopic: 164.074524387
InChI Key:YDBYJHTYSHBBAU-UHFFFAOYSA-O
InChI:InChI=1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1
CAS number:4727-40-6
IUPAC Name:(2S)-2-amino-4-(dimethylsulfaniumyl)butanoate
Traditional IUPAC Name:(2S)-2-amino-4-(dimethylsulfaniumyl)butanoate
SMILES:C[S+](C)CCC(N)C(O)=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
  • L-alpha-amino acid
  • Thia fatty acid
  • Fatty acyl
  • Fatty acid
  • Carboxylic acid salt
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:1
Melting point:139 °C (282 °F) [ 1 ] (bromide salt, decomp.) 134 °C (273 °F) [ 1 ] (chloride salt, decomp.)
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.23 g/LALOGPS
logP0.8ALOGPS
logP-3.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.24ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.93 m³·mol⁻¹ChemAxon
Polarizability17.13 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xs-0900000000-4ddebb53bbc61d1debf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114i-6900000000-24bbf8c2f2b73651a630View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9300000000-d7eebcd08f11a9615826View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-64b75323e952230f5c3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-5900000000-9a1bea81726dd16ade9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-d9e888c0209632b6267eView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID67050
HMDB IDNot Available
Pubchem Compound ID5255805
Kegg IDC03172
ChemSpider ID8373342
WikipediaS-methylmethionine
BioCyc IDNot Available

Enzymes

General function:
Involved in homocysteine S-methyltransferase activity
Specific function:
Catalyzes methyl transfer from S-methylmethionine or S- adenosylmethionine (less efficient) to homocysteine, selenohomocysteine and less efficiently selenocysteine
Gene Name:
mmuM
Uniprot ID:
Q47690
Molecular weight:
33422
Reactions
S-methyl-L-methionine + L-homocysteine = 2 L-methionine.

Transporters

General function:
Involved in transport
Specific function:
Transporter for the intake of S-methylmethionine
Gene Name:
mmuP
Uniprot ID:
Q47689
Molecular weight:
50525
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368