Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2019-11-26 03:06:17 UTC
Primary IDFDB012156
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Selenomethionine
DescriptionFound in onion, cabbage, coco de mono (Lecythis elliptica), Brazil nuts (Bertholletia excelsa), wheat grains and other plants. Dietary supplement for avoidance of Se deficiency in humans and ruminants It has been suggested that selenomethionine, which is an organic form of selenium, is easier for the human body to absorb than selenite, which is an inorganic form. It was determined in a clinical trial that selenomethionine is absorbed 19% better than selenite.; Selenomethionine is an amino acid containing selenium that cannot be synthesized by higher animals, but can be obtained from plant material. Selenomethionine is the major seleno-compound in cereal grains (wheat grain, maize and rice), soybeans and enriched yeast. Seleno-compounds present in plants may have a profound effect upon the health of animals and human subjects. 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. Thus, speciation of the seleno-compounds has moved to the forefront. Since animals and man are dependent upon plants for their nutritional requirements, this makes the types of seleno-compounds in plants even more critical. Se enters the food chain through incorporation into plant proteins, mostly as selenocysteine and selenomethionine at normal Se levels. There are two possible pathways for the catabolism of selenomethionine. One is the transsulfuration pathway via selenocystathionine to produce selenocysteine, which in turn is degraded to H2Se by the enzyme b-lyase. The other pathway is the transamination-decarboxylation pathway. It was estimated that 90% of methionine is metabolized through this pathway and thus could be also the major route for selenomethionine catabolism. (PMID: 14748935, Br J Nutr. 2004 Jan;91(1):11-28.); Selenomethionine is an amino acid containing selenium. The L-isomer of selenomethionine, known as Se-met and Sem, is a common natural food source of selenium. In vivo, selenomethionine is randomly incorporated instead of methionine and is readily oxidized. Its antioxidant activity arises from its ability to deplete reactive species. Selenium and sulfur are chalcogen elements that share many chemical properties and the substitution of methionine to selenomethionine may have no effect on protein structure and function. However, the incorporation of selenomethionine into tissue proteins and keratin in horses causes alkali disease. Alkali disease is characterized by emaciation, loss of hair, deformation and shedding of hooves, loss of vitality and erosion of the joints of long bones.
CAS Number3211-76-5
Structure
Thumb
Synonyms
SynonymSource
(+-)-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
(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
L-2-amino-4-(Methylselenyl)-butyric acidHMDB
Selenomethionine; L-formdb_source
Predicted Properties
PropertyValueSource
Water Solubility109 g/LALOGPS
logP-2.5ALOGPS
logP-3.3ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity42.91 m³·mol⁻¹ChemAxon
Polarizability14.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H11NO2Se
IUPAC name2-amino-4-(methylselanyl)butanoic acid
InChI IdentifierInChI=1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)
InChI KeyRJFAYQIBOAGBLC-UHFFFAOYSA-N
Isomeric SMILESC[Se]CCC(N)C(O)=O
Average Molecular Weight196.11
Monoisotopic Molecular Weight196.995500429
Classification
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 30.62%; H 5.65%; N 7.14%; O 16.32%; Se 40.26%DFC
Melting Point275 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +18.1 (c, 1.22 in 1M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-ad31be05ded6d3690473JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9120000000-b81ef03513ebcd2db684JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f89-0900000000-4949659ad5c41236a070JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9500000000-dbac3b4e6e034ebd3855JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9200000000-d58c983bc06091b8dd74JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kai-2900000000-86628c3188ed75c0a1e6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-1900000000-185fb006e1bba095a984JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-1900000000-d4cebd865ad12ea7d7a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8900000000-797a41add1f29f10c4ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-7900000000-60bc9ba77f492e1b35e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f95-5900000000-7b650680f083adef2064JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-027a3e15d6897c294431JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID14375
ChEMBL IDCHEMBL1474517
KEGG Compound IDC05335
Pubchem Compound ID15103
Pubchem Substance IDNot Available
ChEBI ID27585
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03966
CRC / DFC (Dictionary of Food Compounds) IDHGQ52-F:HDT90-J
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID45598
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cystathionine gamma-lyaseCTHP32929
Methionine--tRNA ligase, cytoplasmicMARSP56192
Methionine--tRNA ligase, mitochondrialMARS2Q96GW9
Pathways
NameSMPDB LinkKEGG Link
Selenoamino Acid MetabolismSMP00029 map00450
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference