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Record Information
Version3.6
Creation Date2006-08-13 08:10:37 UTC
Update Date2016-02-11 01:06:31 UTC
HMDB IDHMDB03966
Secondary Accession NumbersNone
Metabolite Identification
Common NameSelenomethionine
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.).
Structure
Thumb
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
Chemical FormulaC5H11NO2Se
Average Molecular Weight196.11
Monoisotopic Molecular Weight196.995500429
IUPAC Name2-amino-4-(methylselanyl)butanoic acid
Traditional Name(+,-)-selenomethionine
CAS Registry Number3211-76-5
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 KeyInChIKey=RJFAYQIBOAGBLC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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 fatty acid
  • Fatty acyl
  • Fatty acid
  • Selenoether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organoselenium compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point275 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility109.0 mg/mLALOGPS
logP-2.5ALOGPS
logP-3.3ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity42.91 m3·mol-1ChemAxon
Polarizability14.92 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f89-0900000000-4949659ad5c41236a070View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9500000000-dbac3b4e6e034ebd3855View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9200000000-d58c983bc06091b8dd74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-1900000000-185fb006e1bba095a984View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-1900000000-d4cebd865ad12ea7d7a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8900000000-797a41add1f29f10c4ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-7900000000-60bc9ba77f492e1b35e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f95-5900000000-7b650680f083adef2064View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-027a3e15d6897c294431View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Kidney
  • Pancreas
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Selenoamino Acid MetabolismSMP00029map00450
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.69 (0.56 - 0.82) uMAdult (>18 years old)Not Specified
Normal
details
UrineDetected and Quantified0 - 0.002 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.303 +/- 0.099 uMAdult (>18 years old)Not SpecifiedProstate cancer details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Nyman DW, Suzanne Stratton M, Kopplin MJ, Dalkin BL, Nagle RB, Jay Gandolfi A: Selenium and selenomethionine levels in prostate cancer patients. Cancer Detect Prev. 2004;28(1):8-16. [15041072 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012156
KNApSAcK IDNot Available
Chemspider ID14375
KEGG Compound IDC05335
BioCyc IDSELENOMETHIONINE
BiGG ID45598
Wikipedia LinkSelenomethionine
NuGOwiki LinkHMDB03966
Metagene LinkHMDB03966
METLIN ID6993
PubChem Compound15103
PDB IDNot Available
ChEBI ID27585
References
Synthesis ReferenceJakubke, Hans D.; Fischer, J.; Jost, Karel; Rudinger, Josef. Amino acids and peptides. LXXXVI. Synthesis of L-selenomethionine, L-selenoethionine, and their tert-butoxy-carbonyl derivatives. Collection of Czechoslovak Chemical Communications (1968), 33(11), 3910-12.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Greenwald P, Milner JA, Anderson DE, McDonald SS: Micronutrients in cancer chemoprevention. Cancer Metastasis Rev. 2002;21(3-4):217-30. [12549762 ]
  2. Pointner H, Kinast H, Flegel U: 75Se-selenomethionine excretion in bile and pancreatic juice. Digestion. 1975;12(1):61-4. [1175867 ]
  3. Seo YR, Sweeney C, Smith ML: Selenomethionine induction of DNA repair response in human fibroblasts. Oncogene. 2002 May 23;21(23):3663-9. [12032834 ]
  4. Yang X, Tian Y, Ha P, Gu L: [Determination of the selenomethionine content in grain and human blood] Wei Sheng Yan Jiu. 1997 Mar;26(2):113-6. [10325615 ]
  5. Hoang TT, Chen Y, May SW, Browner RF: Analysis of organoselenium compounds in human urine using active carbon and chemically modified silica sol-gel surface-assisted laser desorption/ionization high-resolution time-of-flight mass spectrometry. Anal Chem. 2004 Apr 1;76(7):2062-70. [15053672 ]
  6. Dorea JG: Selenium and breast-feeding. Br J Nutr. 2002 Nov;88(5):443-61. [12425725 ]
  7. Wally J, Halbrooks PJ, Vonrhein C, Rould MA, Everse SJ, Mason AB, Buchanan SK: The crystal structure of iron-free human serum transferrin provides insight into inter-lobe communication and receptor binding. J Biol Chem. 2006 Aug 25;281(34):24934-44. Epub 2006 Jun 22. [16793765 ]
  8. Cabanero AI, Madrid Y, Camara C: Selenium long-term administration and its effect on mercury toxicity. J Agric Food Chem. 2006 Jun 14;54(12):4461-8. [16756381 ]
  9. Wan XS, Zhou Z, Kennedy AR, Kopelovich L: In vitro evaluation of chemopreventive agents using cultured human prostate epithelial cells. Oncol Rep. 2003 Nov-Dec;10(6):2009-14. [14534735 ]
  10. Nakanishi F, Kasuga T, Kobayashi T, Miyabayashi H, Yano K: [Method of analysis of regional dynamics of the pancreas with 75Se-selenomethionine] Kaku Igaku. 1977 Apr;14(2):223-32. [559835 ]
  11. Agnew JE, McCarthy DM, Melmed RNBOUCHIER IA: Count rate analysis as an adjunct to the 75Se-selenomethionine pancreas scan. Br J Radiol. 1969 Oct;42(502):762-9. [5345341 ]
  12. Kuehnelt D, Kienzl N, Traar P, Le NH, Francesconi KA, Ochi T: Selenium metabolites in human urine after ingestion of selenite, L-selenomethionine, or DL-selenomethionine: a quantitative case study by HPLC/ICPMS. Anal Bioanal Chem. 2005 Sep;383(2):235-46. Epub 2005 Oct 12. [16132136 ]
  13. Whanger PD: Selenium and its relationship to cancer: an update. Br J Nutr. 2004 Jan;91(1):11-28. [14748935 ]

Enzymes

General function:
Involved in cobalamin binding
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
MTR
Uniprot ID:
Q99707
Molecular weight:
140525.91
Reactions
Selenohomocysteine + 5-Methyltetrahydropteroyltri-L-glutamate → Selenomethionine + Tetrahydropteroyltri-L-glutamatedetails
General function:
Involved in methionine adenosyltransferase activity
Specific function:
Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name:
MAT2A
Uniprot ID:
P31153
Molecular weight:
43660.37
Reactions
Adenosine triphosphate + Selenomethionine + Water → Phosphoric acid + Pyrophosphate + Se-Adenosylselenomethioninedetails
General function:
Involved in methionine adenosyltransferase activity
Specific function:
Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name:
MAT1A
Uniprot ID:
Q00266
Molecular weight:
43647.6
Reactions
Adenosine triphosphate + Selenomethionine + Water → Phosphoric acid + Pyrophosphate + Se-Adenosylselenomethioninedetails
General function:
Involved in pyridoxal phosphate binding
Specific function:
Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:
CTH
Uniprot ID:
P32929
Molecular weight:
41259.91
Reactions
Selenomethionine + Water → Methaneselenol + Ammonia + 2-Ketobutyric aciddetails
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
MARS
Uniprot ID:
P56192
Molecular weight:
101114.925
Reactions
Adenosine triphosphate + Selenomethionine + tRNA(Met) → Adenosine monophosphate + Pyrophosphate + Selenomethionyl-tRNA(Met)details
General function:
Involved in dTDP-4-dehydrorhamnose reductase activity
Specific function:
Non-catalytic regulatory subunit of S-adenosylmethionine synthetase 2 (MAT2A), an enzyme that catalyzes the formation of S-adenosylmethionine from methionine and ATP. Regulates the activity of S-adenosylmethionine synthetase 2 by changing its kinetic properties, rendering the enzyme more susceptible to S-adenosylmethionine inhibition.
Gene Name:
MAT2B
Uniprot ID:
Q9NZL9
Molecular weight:
Not Available
Reactions
Adenosine triphosphate + Selenomethionine + Water → Phosphoric acid + Pyrophosphate + Se-Adenosylselenomethioninedetails
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
MARS2
Uniprot ID:
Q96GW9
Molecular weight:
66590.29
Reactions
Adenosine triphosphate + Selenomethionine + tRNA(Met) → Adenosine monophosphate + Pyrophosphate + Selenomethionyl-tRNA(Met)details