MiMeDB: Showing metabocard for Selenomethionine (MMDBc0047788)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:42:40 UTC

Update Date

2022-12-15 22:52:16 UTC

Metabolite ID

MMDBc0047788

Metabolite Identification

Common Name

Selenomethionine

Description

Selenomethionine, also known as MSE or semet, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Selenomethionine is a very strong basic compound (based on its pKa). Selenomethionine exists in all living species, ranging from bacteria to humans. selenomethionine can be converted into se-adenosylselenomethionine and phosphoric acid through its interaction with the enzyme S-adenosylmethionine synthase. It is now known that the total Se content cannot be used as an indication of its efficacy, but knowledge of individual selenocompounds is necessary to fully assess the significance. In humans, selenomethionine is involved in selenoamino acid metabolism. Outside of the human body, Selenomethionine has been detected, but not quantified in, several different foods, such as strawberries, oil palms, kohlrabis, gooseberries, and quinces. This could make selenomethionine a potential biomarker for the consumption of these foods. It was estimated that 90% of methionine is metabolized through this pathway and thus could be also the major route for selenomethionine catabolism. Selenomethionine is the major seleno-compound in cereal grains (wheat grain, maize and rice), soybeans and enriched yeast. Selenomethionine is an amino acid containing selenium that cannot be synthesized by higher animals, but can be obtained from plant material. Thus, speciation of the seleno-compounds has moved to the forefront. Seleno-compounds present in plants may have a profound effect upon the health of animals and human subjects. Se enters the food chain through incorporation into plant proteins, mostly as selenocysteine and selenomethionine at normal Se levels. One is the transsulfuration pathway via selenocystathionine to produce selenocysteine, which in turn is degraded to H2Se by the enzyme b-lyase. There are two possible pathways for the catabolism of selenomethionine. Since animals and man are dependent upon plants for their nutritional requirements, this makes the types of seleno-compounds in plants even more critical. The other pathway is the transamination-decarboxylation pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Selenomethionine	ChEBI
Selenium methionine	ChEBI
Seleno-DL-methionine	ChEBI
(2S)-2-Amino-4-(methylseleno)butanoate	HMDB
(2S)-2-Amino-4-(methylseleno)butanoic acid	HMDB
(S)-2-Amino-4-(methylseleno)-butanoate	HMDB
(S)-2-Amino-4-(methylseleno)-butanoic acid	HMDB
(S)-2-Amino-4-(methylseleno)butanoate	HMDB
(S)-2-Amino-4-(methylseleno)butanoic acid	HMDB
(S)-2-Amino-4-(methylseleno)butyric acid	HMDB
2-Amino-4-(methylseleno)butanoate	HMDB
2-Amino-4-(methylseleno)butanoic acid	HMDB
2-Amino-4-(methylselenyl)butyrate	HMDB
2-Amino-4-(methylselenyl)butyric acid	HMDB
DL-Selenomethionine	HMDB
L(+)-Selenomethionine	HMDB
L-2-Amino-4-(methylselenyl)-butyric acid	HMDB
L-Selenomethionine	HMDB
L-Selenomethioninum	HMDB
MSE	HMDB
Selenium-L-methionine	HMDB
Seleno-D,L-methionine	HMDB
Seleno-L-methionine	HMDB
Selenomethionine se 75	HMDB
SeMet	HMDB
Sethotope	HMDB
Selenomethionine hydrochloride, (S)-isomer	HMDB
Selenomethionine, (S)-isomer	HMDB
Radioselenomethionine	HMDB
Selenomethionine, (+,-)-isomer	HMDB
Selenomethionine, (R)-isomer	HMDB
Se 75, selenomethionine	HMDB

Molecular Formula

C₅H₁₁NO₂Se

Average Mass

196.11

Monoisotopic Mass

196.995500429

IUPAC Name

2-amino-4-(methylselanyl)butanoic acid

Traditional Name

(+,-)-selenomethionine

CAS Registry Number

Not Available

SMILES

C[Se]CCC(N)C(O)=O

InChI Identifier

InChI=1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

InChI Key

RJFAYQIBOAGBLC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Fatty acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Selenoether
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organoselenium compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

selenoamino acid (CHEBI:27585 )
selenomethionines (CHEBI:27585 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	109 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.3	ChemAxon
logS	-0.25	ALOGPS
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	9.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	42.91 m³·mol⁻¹	ChemAxon
Polarizability	14.92 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

Biospecimen Locations

Blood
Feces
Fibroblasts
Kidney
Pancreas
Prostate
Urine

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
MMDBr0019827	Selenomethionine	Adenosine monophosphate	Methionine--tRNA ligase, cytoplasmic	Ligation	PathBank	31602464
MMDBr0019828	Selenomethionine	2-Ketobutyric acid	Cystathionine gamma-lyase	Non-hydrolytic bond cleavage (or its reversal)	PathBank	31602464
MMDBr0019829	Selenohomocysteine	tetrahydropteroyltri-L-glutamate	5-methyltetrahydropteroyltriglutamate--homocysteine 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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Fibroblasts	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0003966

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012370

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

27585

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
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 ]

Showing metabocard for Selenomethionine (MMDBc0047788)

MOL for #<Metabolite:0x00007f9258037978>

3D MOL for #<Metabolite:0x00007f9258037978>

3D SDF for #<Metabolite:0x00007f9258037978>

3D-SDF for #<Metabolite:0x00007f9258037978>

PDB for #<Metabolite:0x00007f9258037978>

3D PDB for #<Metabolite:0x00007f9258037978>

SMILES for #<Metabolite:0x00007f9258037978>

INCHI for #<Metabolite:0x00007f9258037978>

Structure for #<Metabolite:0x00007f9258037978>

3D Structure for #<Metabolite:0x00007f9258037978>