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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 11:13:59 UTC
Update Date2021-09-14 15:45:11 UTC
HMDB IDHMDB0004113
Secondary Accession Numbers
  • HMDB0031466
  • HMDB04113
  • HMDB31466
Metabolite Identification
Common NameSe-Methylselenocysteine
DescriptionSe-Methylselenocysteine (SeMSC) is a naturally occurring seleno-amino acid that is synthesized by plants such as garlic, astragalus, onions, and broccoli. It cannot be synthesized by higher animals. Unlike selenomethionine, which is incorporated into proteins in place of methionine, SeMSC is not incorporated into any proteins, thereby being fully available for the synthesis of selenium-containing enzymes such as glutathione peroxidase. 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: (1) a transsulfuration pathway via selenocystathionine to produce selenocysteine, which in turn is degraded to H2Se by the enzyme beta-lyase and (2) a 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.
Structure
Data?1582752299
Synonyms
ValueSource
L-MethylselenocysteineChEBI
Methyl-L-selenocysteineChEBI
MethylselenocysteineChEBI
Se-methyl-seleno-L-cysteineChEBI
Se-methyl-selenocysteineChEBI
Selenium methyl cysteineChEBI
Selenium-methylselenocystineChEBI
SelenohomocysteineChEBI
SelenomethylselenocysteineChEBI
3-(Methylseleno)-L-alanineHMDB
Se-methyl-L-selenocysteineHMDB
L-Methyl-selenocysteineHMDB
Methyl selenocysteineHMDB
Selenomethylselenocysteine, (D,L)-isomerHMDB
Selenomethylselenocysteine, (L)-isomer, 75Se-labeledHMDB
SeMCysHMDB
Selenomethylselenocysteine, (L)-isomerHMDB
Methylseleno-L-cysteineHMDB
Selenomethyl selenocysteineHMDB
Se-MethylselenocysteineHMDB
Chemical FormulaC4H9NO2Se
Average Molecular Weight182.08
Monoisotopic Molecular Weight182.979850365
IUPAC Name(2R)-2-amino-3-(methylselanyl)propanoic acid
Traditional Namemethylselenocysteine
CAS Registry Number26046-90-2
SMILES
C[Se]C[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyXDSSPSLGNGIIHP-VKHMYHEASA-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
  • 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

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility156 g/LALOGPS
logP10(-2.8) g/LALOGPS
logP10(-3.5) g/LChemAxon
logS10(-0.07) g/LALOGPS
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
Polarizability12.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Se-Methylselenocysteine,1TMS,#1C[Se]C[C@H](N)C(=O)O[Si](C)(C)C1361.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Se-Methylselenocysteine,1TMS,#2C[Se]C[C@H](N[Si](C)(C)C)C(=O)O1443.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Se-Methylselenocysteine,1TBDMS,#1C[Se]C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C1623.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Se-Methylselenocysteine,1TBDMS,#2C[Se]C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O1689.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Se-Methylselenocysteine GC-MS (1 TMS)splash10-000i-2900000000-584579d62a5c494d1ad42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Se-Methylselenocysteine GC-MS (2 TMS)splash10-0i00-1960000000-c1d9d3d6c03ef447c6822014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Se-Methylselenocysteine GC-MS (Non-derivatized)splash10-000i-2900000000-584579d62a5c494d1ad42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Se-Methylselenocysteine GC-MS (Non-derivatized)splash10-0i00-1960000000-c1d9d3d6c03ef447c6822017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Se-Methylselenocysteine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-b52de18849d5860694de2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Se-Methylselenocysteine GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9110000000-370afb49a49bc4836d3e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Se-Methylselenocysteine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 10V, Positive-QTOFsplash10-001r-0900000000-87ae6338ccd9513f5db02015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 20V, Positive-QTOFsplash10-001r-1900000000-204e0c71178a372a67d02015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 40V, Positive-QTOFsplash10-000f-9800000000-f08ef5fe840b11c1330b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 10V, Negative-QTOFsplash10-00lu-5900000000-267cb39ae0470e212ce22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 20V, Negative-QTOFsplash10-0079-9400000000-7ae0b50471ba90d5656c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 40V, Negative-QTOFsplash10-0006-9300000000-7580c3589d69535a4bb72015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 10V, Negative-QTOFsplash10-0006-9000000000-f9689d19a8a4fb34dc2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 20V, Negative-QTOFsplash10-0006-9000000000-f9689d19a8a4fb34dc2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 40V, Negative-QTOFsplash10-0006-9000000000-f9689d19a8a4fb34dc2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 10V, Positive-QTOFsplash10-00lr-0900000000-d519041b7fbf3920f7ee2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 20V, Positive-QTOFsplash10-00y0-0900000000-88e1671d699eb2ba32332021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Se-Methylselenocysteine 40V, Positive-QTOFsplash10-00dl-5900000000-c1dd9e6e9d3616306ddc2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12697
Phenol Explorer Compound IDNot Available
FooDB IDFDB012599
KNApSAcK IDC00001382 C00034232
Chemspider ID129633
KEGG Compound IDC05689
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylselenocysteine
METLIN ID7019
PubChem Compound147004
PDB IDNot Available
ChEBI ID27812
Food Biomarker OntologyNot Available
VMH IDM02895
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSpallholz, Julian E.; Reid, Ted W.; Walkup, Robert D. A method of using synthetic L-Se-methylselenocysteine as a nutriceutical. Eur. Pat. Appl. (2002), 21 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yin MB, Li ZR, Cao S, Durrani FA, Azrak RG, Frank C, Rustum YM: Enhanced 7-ethyl-10-hydroxycamptothecin (SN-38) lethality by methylselenocysteine is associated with Chk2 phosphorylation at threonine-68 and down-regulation of Cdc6 expression. Mol Pharmacol. 2004 Jul;66(1):153-60. [PubMed:15213307 ]
  2. Whanger PD: Selenium and its relationship to cancer: an update. Br J Nutr. 2004 Jan;91(1):11-28. [PubMed:14748935 ]
  3. (). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .

Enzymes

General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:
CCBL1
Uniprot ID:
Q16773
Molecular weight:
47874.765
Reactions
Se-Methylselenocysteine + 2-Oxo-4-methylthiobutanoic acid → Methylselenopyruvate + L-Methioninedetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:
GGT1
Uniprot ID:
P19440
Molecular weight:
61409.67
Reactions
(5-L-Glutamyl)-peptide + Se-Methylselenocysteine → Peptide + Gamma-Glutamyl-Se-methylselenocysteinedetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT7
Uniprot ID:
Q9UJ14
Molecular weight:
70466.015
Reactions
(5-L-Glutamyl)-peptide + Se-Methylselenocysteine → Peptide + Gamma-Glutamyl-Se-methylselenocysteinedetails
General function:
Involved in metabolic process
Specific function:
Catalyzes the decomposition of L-selenocysteine to L-alanine and elemental selenium (By similarity).
Gene Name:
SCLY
Uniprot ID:
Q96I15
Molecular weight:
48793.15
Reactions
Se-Methylselenocysteine + Water → Pyruvic acid + Ammonia + Methaneselenoldetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT6
Uniprot ID:
Q6P531
Molecular weight:
50508.83
Reactions
(5-L-Glutamyl)-peptide + Se-Methylselenocysteine → Peptide + Gamma-Glutamyl-Se-methylselenocysteinedetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:
CCBL2
Uniprot ID:
Q6YP21
Molecular weight:
51399.855
Reactions
Se-Methylselenocysteine + 2-Oxo-4-methylthiobutanoic acid → Methylselenopyruvate + L-Methioninedetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Not Available
Gene Name:
GGT7
Uniprot ID:
A0PJJ9
Molecular weight:
62565.3
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:
GGT5
Uniprot ID:
P36269
Molecular weight:
62331.75
Reactions
(5-L-Glutamyl)-peptide + Se-Methylselenocysteine → Peptide + Gamma-Glutamyl-Se-methylselenocysteinedetails