Record Information
Version1.0
Creation date2010-04-08 22:10:08 UTC
Update date2018-05-28 23:36:10 UTC
Primary IDFDB012370
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSelenomethionine
DescriptionSelenomethionine, also known as (2s)-2-amino-4-(methylseleno)butanoate or 2-amino-4-(methylselenyl)butyric acid, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Selenomethionine is soluble (in water) and a moderately acidic compound (based on its pKa). Selenomethionine can be found in a number of food items such as shiitake, canada blueberry, sesbania flower, and spearmint, which makes selenomethionine a potential biomarker for the consumption of these food products. Selenomethionine can be found primarily in blood and urine, as well as throughout most human tissues. Selenomethionine exists in all eukaryotes, ranging from yeast to humans. In humans, selenomethionine is involved in the selenoamino acid metabolism. Moreover, selenomethionine is found to be associated with prostate cancer. Selenomethionine is a naturally occurring amino acid. The L-selenomethionine enantiomer is the main form of selenium found in Brazil nuts, cereal grains, soybeans, and grassland legumes, while Se-methylselenocysteine, or its γ-glutamyl derivative, is the major form of selenium found in Astragalus, Allium, and Brassica species. In vivo, selenomethionine is randomly incorporated instead of methionine. Selenomethionine is readily oxidized .
CAS Number1464-42-2
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
2-Amino-4-(methylseleno)butanoic acid, 9CIdb_source
2-Amino-4-(methylselenyl)butyric acid, 8CIdb_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
Bioavailability1ChemAxon
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 30.62%; H 5.65%; N 7.14%; O 16.32%; Se 40.26%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHGQ52-F:HGQ52-F
EAFUS IDNot Available
Dr. Duke IDSELENO-METHIONINE
BIGG IDNot Available
KNApSAcK IDC00034231
HET 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).