Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 15:42:40 UTC
Update Date2022-12-15 22:52:16 UTC
Metabolite IDMMDBc0047788
Metabolite Identification
Common NameSelenomethionine
DescriptionSelenomethionine, 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
Synonyms
ValueSource
(+-)-SelenomethionineChEBI
Selenium methionineChEBI
Seleno-DL-methionineChEBI
(2S)-2-Amino-4-(methylseleno)butanoateHMDB
(2S)-2-Amino-4-(methylseleno)butanoic acidHMDB
(S)-2-Amino-4-(methylseleno)-butanoateHMDB
(S)-2-Amino-4-(methylseleno)-butanoic acidHMDB
(S)-2-Amino-4-(methylseleno)butanoateHMDB
(S)-2-Amino-4-(methylseleno)butanoic acidHMDB
(S)-2-Amino-4-(methylseleno)butyric acidHMDB
2-Amino-4-(methylseleno)butanoateHMDB
2-Amino-4-(methylseleno)butanoic acidHMDB
2-Amino-4-(methylselenyl)butyrateHMDB
2-Amino-4-(methylselenyl)butyric acidHMDB
DL-SelenomethionineHMDB
L(+)-SelenomethionineHMDB
L-2-Amino-4-(methylselenyl)-butyric acidHMDB
L-SelenomethionineHMDB
L-SelenomethioninumHMDB
MSEHMDB
Selenium-L-methionineHMDB
Seleno-D,L-methionineHMDB
Seleno-L-methionineHMDB
Selenomethionine se 75HMDB
SeMetHMDB
SethotopeHMDB
Selenomethionine hydrochloride, (S)-isomerHMDB
Selenomethionine, (S)-isomerHMDB
RadioselenomethionineHMDB
Selenomethionine, (+,-)-isomerHMDB
Selenomethionine, (R)-isomerHMDB
Se 75, selenomethionineHMDB
Molecular FormulaC5H11NO2Se
Average Mass196.11
Monoisotopic Mass196.995500429
IUPAC Name2-amino-4-(methylselanyl)butanoic acid
Traditional Name(+,-)-selenomethionine
CAS Registry NumberNot 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 KeyRJFAYQIBOAGBLC-UHFFFAOYSA-N