Selenomethionine (CHEM017556)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:27:42 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017556
Identification
Common NameSelenomethionine
ClassSmall Molecule
DescriptionA selenoamino acid that is the selenium analogue of methionine.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
Selenomethionine hydrochloride, (S)-isomerHMDB
Selenomethionine, (S)-isomerHMDB
RadioselenomethionineHMDB
Selenomethionine, (+,-)-isomerHMDB
Selenomethionine, (R)-isomerHMDB
Se 75, selenomethionineHMDB
Chemical FormulaC5H11NO2Se
Average Molecular Mass196.110 g/mol
Monoisotopic Mass196.996 g/mol
CAS Registry Number1464-42-2
IUPAC Name2-amino-4-(methylselanyl)butanoic acid
Traditional Name(+,-)-selenomethionine
SMILESC[Se]CCC(N)C(O)=O
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability14.92 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-ad31be05ded6d3690473Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9120000000-b81ef03513ebcd2db684Spectrum
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-1900000000-185fb006e1bba095a984Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-1900000000-d4cebd865ad12ea7d7a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8900000000-797a41add1f29f10c4ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-7900000000-60bc9ba77f492e1b35e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f95-5900000000-7b650680f083adef2064Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-027a3e15d6897c294431Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003966
FooDB IDFDB012370
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45598
BioCyc IDSELENOMETHIONINE
METLIN ID6993
PDB IDNot Available
Wikipedia LinkSelenomethionine
Chemspider ID14375
ChEBI ID27585
PubChem Compound ID15103
Kegg Compound IDC05335
YMDB IDYMDB16175
ECMDB IDECMDB03966
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14969538
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20740325
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21259435
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21286848
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21366307
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21524942
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21603917
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21766323
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21870603
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21877325
11. Jakubke, 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.
12. Jakubke, 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.
13. Greenwald P, Milner JA, Anderson DE, McDonald SS: Micronutrients in cancer chemoprevention. Cancer Metastasis Rev. 2002;21(3-4):217-30.
14. Pointner H, Kinast H, Flegel U: 75Se-selenomethionine excretion in bile and pancreatic juice. Digestion. 1975;12(1):61-4.
15. Seo YR, Sweeney C, Smith ML: Selenomethionine induction of DNA repair response in human fibroblasts. Oncogene. 2002 May 23;21(23):3663-9.
16. 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.
17. 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.
18. Dorea JG: Selenium and breast-feeding. Br J Nutr. 2002 Nov;88(5):443-61.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. Whanger PD: Selenium and its relationship to cancer: an update. Br J Nutr. 2004 Jan;91(1):11-28.