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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-12 00:00:09 UTC

Update Date

2022-09-22 18:34:26 UTC

HMDB ID

HMDB0038670

Secondary Accession Numbers

HMDB38670

Metabolite Identification

Common Name

S-Methylmethionine

Description

S-Methylmethionine (SMM) belongs to the class of organic compounds known as methionines and derivatives. Methionines 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 a derivative of methionine. It 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. As a result, S-Methylmethionine is found, on average, in the highest concentration within a few different plant foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea, black tea. It is also found in garden tomatoes. S-Methylmethionine has also been detected, but not quantified in, several different foods, such as prunus (cherry, plum), barley, nuts, root vegetables, onion-family vegetables, and sapodillas (Manilkara zapota). This could make S-methylmethionine a potential biomarker for the consumption of these foods. S-Methylmethionine is naturally found in barley and is further created during the malting process to produce beer. SMM can be subsequently converted to dimethyl sulfide (DMS) during the malt kilning process, causing an undesirable flavor in beer. 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- The biological roles of S-methylmethionine are not well understood. Speculated roles include methionine storage, use as a methyl donor, regulation of S-adenosylmethionine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3-amino-3-Carboxypropyl)dimethylsulfonium(1+), 9ci, 8ci	HMDB
S-Methyl-L-methionine	HMDB
Chloride, methionine methylsulfonium	MeSH, HMDB
Methionine methylsulfonium chloride	MeSH, HMDB
Methylmethionine	MeSH, HMDB
Methylmethionine sulfonium chloride	MeSH, HMDB
Methylsulfonium chloride, methionine	MeSH, HMDB
S Methylmethionine	MeSH, HMDB
Chloride, methylmethioninesulfonium	MeSH, HMDB
Sulfonium, ((3S)-3-amino-3-carboxypropyl)dimethyl-, inner salt	MeSH, HMDB
Methylmethioninesulfonium chloride	MeSH, HMDB
Vitamin u	MeSH, HMDB

Chemical Formula

C₆H₁₄NO₂S

Average Molecular Weight

164.246

Monoisotopic Molecular Weight

164.074524387

IUPAC Name

(3-amino-3-carboxypropyl)dimethylsulfanium

Traditional Name

S-methylmethionine

CAS Registry Number

13065-25-3

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 Key

YDBYJHTYSHBBAU-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.

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
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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	139 °C (decomposition)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	17.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.363	31661259
DarkChem	[M-H]-	131.546	31661259
DeepCCS	[M+H]+	129.989	30932474
DeepCCS	[M-H]-	126.227	30932474
DeepCCS	[M-2H]-	163.481	30932474
DeepCCS	[M+Na]+	138.864	30932474
AllCCS	[M+H]+	133.3	32859911
AllCCS	[M+H-H2O]+	129.7	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	140.0	32859911
AllCCS	[M+Na-2H]-	142.3	32859911
AllCCS	[M+HCOO]-	144.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-Methylmethionine	C[S+](C)CCC(N)C(O)=O	2183.7	Standard polar	33892256
S-Methylmethionine	C[S+](C)CCC(N)C(O)=O	1308.4	Standard non polar	33892256
S-Methylmethionine	C[S+](C)CCC(N)C(O)=O	1474.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-Methylmethionine,1TMS,isomer #1	C[S+](C)CCC(N)C(=O)O[Si](C)(C)C	1358.9	Semi standard non polar	33892256
S-Methylmethionine,1TMS,isomer #2	C[S+](C)CCC(N[Si](C)(C)C)C(=O)O	1454.0	Semi standard non polar	33892256
S-Methylmethionine,2TMS,isomer #1	C[S+](C)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1461.7	Semi standard non polar	33892256
S-Methylmethionine,2TMS,isomer #1	C[S+](C)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1531.7	Standard non polar	33892256
S-Methylmethionine,2TMS,isomer #2	C[S+](C)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1634.2	Semi standard non polar	33892256
S-Methylmethionine,2TMS,isomer #2	C[S+](C)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1588.9	Standard non polar	33892256
S-Methylmethionine,3TMS,isomer #1	C[S+](C)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1632.1	Semi standard non polar	33892256
S-Methylmethionine,3TMS,isomer #1	C[S+](C)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1654.3	Standard non polar	33892256
S-Methylmethionine,1TBDMS,isomer #1	C[S+](C)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C	1590.9	Semi standard non polar	33892256
S-Methylmethionine,1TBDMS,isomer #2	C[S+](C)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O	1679.9	Semi standard non polar	33892256
S-Methylmethionine,2TBDMS,isomer #1	C[S+](C)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1908.7	Semi standard non polar	33892256
S-Methylmethionine,2TBDMS,isomer #1	C[S+](C)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1969.5	Standard non polar	33892256
S-Methylmethionine,2TBDMS,isomer #2	C[S+](C)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2049.5	Semi standard non polar	33892256
S-Methylmethionine,2TBDMS,isomer #2	C[S+](C)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2028.0	Standard non polar	33892256
S-Methylmethionine,3TBDMS,isomer #1	C[S+](C)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2284.7	Semi standard non polar	33892256
S-Methylmethionine,3TBDMS,isomer #1	C[S+](C)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2291.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-Methylmethionine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-9600000000-31877974a2a73693c8d9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-Methylmethionine GC-MS (1 TMS) - 70eV, Positive	splash10-0629-9400000000-f82a0c4d166de3a4966b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-Methylmethionine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - S-Methylmethionine 30V, Positive-QTOF	splash10-0ab9-9700000000-05e1395a26bf999e10f8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - S-Methylmethionine 0V, Positive-QTOF	splash10-03di-0900000000-50569e3897f7d5368804	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - S-Methylmethionine 10V, Positive-QTOF	splash10-0zfr-6900000000-17907795db5aa38cb0d3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Methylmethionine 10V, Positive-QTOF	splash10-02t9-0900000000-1c593a8242fb277a76ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Methylmethionine 20V, Positive-QTOF	splash10-0aor-8900000000-586659c7bdf583fdac59	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Methylmethionine 40V, Positive-QTOF	splash10-06vi-9100000000-7536d21f47277c6d682f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Methylmethionine 10V, Positive-QTOF	splash10-0nmi-7900000000-fa07fa5a6cf9bfc89611	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Methylmethionine 20V, Positive-QTOF	splash10-0a4i-9100000000-820f5f35e25cd2f52cfe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Methylmethionine 40V, Positive-QTOF	splash10-0a4i-9000000000-f3e149e0e4649d0d4f89	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018070

KNApSAcK ID

Not Available

Chemspider ID

445

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

S-Methylmethionine

METLIN ID

Not Available

PubChem Compound

458

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

MMET

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for S-Methylmethionine (HMDB0038670)

MOL for HMDB0038670 (S-Methylmethionine)

3D MOL for HMDB0038670 (S-Methylmethionine)

3D SDF for HMDB0038670 (S-Methylmethionine)

3D-SDF for HMDB0038670 (S-Methylmethionine)

PDB for HMDB0038670 (S-Methylmethionine)

3D PDB for HMDB0038670 (S-Methylmethionine)

SMILES for HMDB0038670 (S-Methylmethionine)

INCHI for HMDB0038670 (S-Methylmethionine)

Structure for HMDB0038670 (S-Methylmethionine)

3D Structure for HMDB0038670 (S-Methylmethionine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra