S-Methyl-L-methionine (YMDB00347)

Identification

YMDB ID

YMDB00347

Name

S-Methyl-L-methionine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

S-Methylmethionine is a derivative of methionine. This cation is an intermediate in many biosynthetic pathways owing to the sulfonium functional group. The natural derivative S-methylmethionine is biosynthesized from L-methionine which is first converted to S-adenosylmethionine. The subsequent conversion, involving replacement of the adenosyl group by a methyl group is catalyzed by the enzyme methionine S-methyltransferase. S-Methylmethionine is particularly abundant in plants, being more abundant than methionine. [Wikipedia]

Structure

MOL SDF PDB SMILES InChI

Synonyms

S-Methyl-L-methionine
L-Methionine methylsulfonium
L-Methionine methylsulphonium
S-Methylmethionine

CAS number

4727-40-6

Weight

Average: 164.246
Monoisotopic: 164.074524387

InChI Key

YDBYJHTYSHBBAU-YFKPBYRVSA-O

InChI

InChI=1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1/t5-/m0/s1

IUPAC Name

[(3S)-3-amino-3-carboxypropyl]dimethylsulfanium

Traditional IUPAC Name

S-methyl-L-methionine

Chemical Formula

C₆H₁₄NO₂S

SMILES

C[S+](C)CC[C@H](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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Methionine and derivatives

Alternative Parents

Substituents

Methionine or derivatives
Alpha-amino acid
L-alpha-amino acid
Thia fatty acid
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Organic oxide
Carbonyl group
Amine
Organopnictogen compound
Organic oxygen compound
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfonium compound (CHEBI:17728 )

Physical Properties

State

Solid

Charge

Melting point

139 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	8.12 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-3.3	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.24	ChemAxon
pKa (Strongest Basic)	9.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.1 m³·mol⁻¹	ChemAxon
Polarizability	17.56 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-9500000000-a93727c5213fe4bd311d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02t9-0900000000-1c593a8242fb277a76ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aor-8900000000-586659c7bdf583fdac59	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06vi-9100000000-7536d21f47277c6d682f	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17728
HMDB ID	Not Available
Pubchem Compound ID	145692
Kegg ID	C03172
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia	S-Methylmethionine
BioCyc ID	Not Available

Enzymes

Protein Details

1. Homocysteine S-methyltransferase 1

General function:: Involved in homocysteine S-methyltransferase activity
Specific function:: Homocysteine S-methyltransferase involved in the conversion of S-adenosylmethionine (AdoMet) to methionine to control the methionine/AdoMet ratio. Converts also S- methylmethionine (SMM) to methionine
Gene Name:: MHT1
Uniprot ID:: Q12525
Molecular weight:: 36714.5

Reactions

S-methyl-L-methionine + L-homocysteine → 2 L-methionine.

Protein Details

2. Homocysteine S-methyltransferase 2

General function:: Involved in homocysteine S-methyltransferase activity
Specific function:: Homocysteine S-methyltransferase involved in the conversion of S-adenosylmethionine (AdoMet) to methionine to control the methionine/AdoMet ratio. Converts also S- methylmethionine (SMM) to methionine
Gene Name:: SAM4
Uniprot ID:: Q08985
Molecular weight:: 36668.19922

Reactions

S-methyl-L-methionine + L-homocysteine → 2 L-methionine.

Transporters

Protein Details

1. S-methylmethionine permease 1

General function:: Involved in transport
Specific function:: High-affinity S-methylmethionine (SMM) permease, required for utilization of S-methylmethionine as a sulfur source
Gene Name:: MMP1
Uniprot ID:: Q12372
Molecular weight:: 64217.0

Structure for #<Compound:0xaa567ca0>

Enzymes

Reactions

Reactions

Transporters