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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 08:10:37 UTC
Update Date2020-06-15 17:04:52 UTC
HMDB IDHMDB0003966
Secondary Accession Numbers
  • HMDB03966
Metabolite Identification
Common NameSelenomethionine
DescriptionSelenomethionine (CAS: 1464-42-2) 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 on 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 into H2Se by the enzyme beta-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
Data?1583854917
Synonyms
ValueSource
Selenomethionine, (+,-)-isomerMeSH
Selenomethionine se 75MeSH
RadioselenomethionineMeSH
Selenomethionine, (S)-isomerMeSH
SethotopeMeSH
Se 75, selenomethionineMeSH
Selenomethionine hydrochloride, (S)-isomerMeSH
Selenomethionine, (R)-isomerMeSH
SelenomethionineMeSH
(2S)-2-Amino-4-(methylseleno)butanoic acidHMDB
(2S)-2-Azaniumyl-4-methylselanylbutanoateHMDB
L-SelenomethionineHMDB
Seleno-L-methionineHMDB
2-Amino-4-(methylseleno)butanoic acidHMDB
2-Amino-4-(methylseleno)butyric acidHMDB
2-Amino-4-(methylselenyl)butyric acidHMDB
Selenium methionineHMDB
Chemical FormulaC5H11NO2Se
Average Molecular Weight196.11
Monoisotopic Molecular Weight196.995500429
IUPAC Name(2S)-2-amino-4-(methylselanyl)butanoic acid
Traditional NameL-selenomethionine
CAS Registry Number3211-76-5
SMILES
C[Se]CC[C@H](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)/t4-/m0/s1
InChI KeyRJFAYQIBOAGBLC-BYPYZUCNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Selenoether
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organoselenium compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

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 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
Polarizability14.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0pc0-2910000000-c7140386a1899064bb79Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00b9-0950000000-05c9f3aa6ccd78087856Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f89-0900000000-4949659ad5c41236a070Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9500000000-dbac3b4e6e034ebd3855Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9200000000-d58c983bc06091b8dd74Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kai-2900000000-86628c3188ed75c0a1e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-1900000000-4c7499267ca09c35d1fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-1900000000-c8febb206f8338bc0103Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8900000000-ed5cee25f7460f6dee63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-7900000000-d4ba86036408b6707652Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6w-5900000000-98925ed00d83d0cb75d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-a9e17e100c4c54504073Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Fibroblasts
  • Kidney
  • Pancreas
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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. [PubMed:15041072 ]
Associated OMIM IDs
DrugBank IDDB11142
Phenol Explorer Compound IDNot Available
FooDB IDFDB012156
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05335
BioCyc IDSELENOMETHIONINE
BiGG IDNot Available
Wikipedia LinkSelenomethionine
METLIN IDNot Available
PubChem Compound105024
PDB IDNot Available
ChEBI ID30021
Food Biomarker OntologyNot Available
VMH IDNot Available
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. Pointner H, Kinast H, Flegel U: 75Se-selenomethionine excretion in bile and pancreatic juice. Digestion. 1975;12(1):61-4. [PubMed:1175867 ]
  2. Greenwald P, Milner JA, Anderson DE, McDonald SS: Micronutrients in cancer chemoprevention. Cancer Metastasis Rev. 2002;21(3-4):217-30. [PubMed:12549762 ]
  3. Seo YR, Sweeney C, Smith ML: Selenomethionine induction of DNA repair response in human fibroblasts. Oncogene. 2002 May 23;21(23):3663-9. [PubMed: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. [PubMed: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. [PubMed:15053672 ]
  6. Dorea JG: Selenium and breast-feeding. Br J Nutr. 2002 Nov;88(5):443-61. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16132136 ]
  13. Whanger PD: Selenium and its relationship to cancer: an update. Br J Nutr. 2004 Jan;91(1):11-28. [PubMed: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-glutamic acid → Selenomethionine + Tetrahydropteroyltri-L-glutamic aciddetails
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 → Phosphate + 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 → Phosphate + 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 → Phosphate + 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