MiMeDB: Showing metabocard for S-Methylmethionine (MMDBc0000672)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:52:25 UTC

Update Date

2024-04-30 19:33:28 UTC

Metabolite ID

MMDBc0000672

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

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

Molecular Formula

C₆H₁₄NO₂S

Average Mass

164.246

Monoisotopic Mass

164.074524387

IUPAC Name

(3-amino-3-carboxypropyl)dimethylsulfanium

Traditional Name

S-methylmethionine

CAS Registry Number

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	17.68 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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019148	S-Methylmethionine	L-Methionine	Homocysteine S-methyltransferase	Methylation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0038670

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

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for S-Methylmethionine (MMDBc0000672)

MOL for #<Metabolite:0x00007f9209fbf548>

3D MOL for #<Metabolite:0x00007f9209fbf548>

3D SDF for #<Metabolite:0x00007f9209fbf548>

3D-SDF for #<Metabolite:0x00007f9209fbf548>

PDB for #<Metabolite:0x00007f9209fbf548>

3D PDB for #<Metabolite:0x00007f9209fbf548>

SMILES for #<Metabolite:0x00007f9209fbf548>

INCHI for #<Metabolite:0x00007f9209fbf548>

Structure for #<Metabolite:0x00007f9209fbf548>

3D Structure for #<Metabolite:0x00007f9209fbf548>