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Selenomethyl selenocysteine (FDB007914)

Record Information
Version1.0
Creation date2010-04-08 22:07:50 UTC
Update date2019-11-26 03:01:53 UTC
Primary IDFDB007914
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSelenomethyl selenocysteine
DescriptionSelenomethionine 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. Selenomethyl selenocysteine is found in garden onion.
CAS Number2574-71-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility156 g/LALOGPS
logP-2.8ALOGPS
logP-3.5ChemAxon
logS-0.07ALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.2 m³·mol⁻¹ChemAxon
Polarizability12.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H9NO2Se
IUPAC name2-amino-3-(methylselanyl)propanoic acid
InChI IdentifierInChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
InChI KeyXDSSPSLGNGIIHP-UHFFFAOYSA-N
Isomeric SMILESC[Se]CC(N)C(O)=O
Average Molecular Weight182.08
Monoisotopic Molecular Weight182.979850365
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
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Selenoether
  • Hydrocarbon derivative
  • Amine
  • Primary amine
  • Organoselenium compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point275 oC
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSelenomethyl selenocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9400000000-5699b2275220d8aadde4Spectrum
Predicted GC-MSSelenomethyl selenocysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-9500000000-8c95c038698906dd75d0Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-0900000000-de3b139d0ac0d3f4d89b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-1900000000-5e2d0fabd6b6adc7f06a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9800000000-73374b11e7a85d6db9912016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lu-5900000000-cf4d9e0841b1c6ac59562016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9300000000-3bdf71c4ae215b24a4de2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-5052b01ad7e4c73119602016-08-03View Spectrum
NMRNot Available
ChemSpider ID102795
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID114835
Pubchem Substance IDNot Available
ChEBI ID9068
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31466
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDSELENO-METHYL-SELENOCYSTEINE
BIGG IDNot Available
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 / Bioactivities
DescriptorIDDefinitionReference
anti neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.CHEBI
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).