Se-Methylselenocysteine (ECMDB21009) (M2MDB001427)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (465)
Record Information
Version2.0
Creation Date2012-05-31 14:54:17 -0600
Update Date2015-09-13 12:56:14 -0600
Secondary Accession Numbers
  • ECMDB21009
Identification
Name:Se-Methylselenocysteine
DescriptionSe-Methylselenocysteine (SeMSC) is a naturally occurring seleno-amino acid that is synthesized by plants such as garlic, astragalus, onions and broccoli. SeMSC is an intermediate in selenoamino acid metabolism. 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 3-(Methylseleno)-L-Alanine
  • Methylselenocysteine
  • Se-Methyl-L-selenocysteine
  • Selenium-methylselenocystine
Chemical Formula:C4H9NO2Se
Weight:Average: 182.08
Monoisotopic: 182.979850365
InChI Key:XDSSPSLGNGIIHP-VKHMYHEASA-N
InChI:InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
CAS number:26046-90-2
IUPAC Name:(2R)-2-amino-3-(methylselanyl)propanoic acid
Traditional IUPAC Name:methylselenocysteine
SMILES:C[Se]C[C@H](N)C(O)=O
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
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Polarizability12.89 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
(5-L-Glutamyl)-peptide + Se-Methylselenocysteine <> Peptide + gamma-Glutamyl-Se-methylselenocysteine
Se-Methylselenocysteine + Water <> Pyruvic acid + Ammonia + Methaneselenol
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000i-2900000000-584579d62a5c494d1ad4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0i00-1960000000-c1d9d3d6c03ef447c682View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-2900000000-584579d62a5c494d1ad4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0i00-1960000000-c1d9d3d6c03ef447c682View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-b52de18849d5860694deView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9110000000-370afb49a49bc4836d3eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-0900000000-87ae6338ccd9513f5db0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-1900000000-204e0c71178a372a67d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9800000000-f08ef5fe840b11c1330bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lu-5900000000-267cb39ae0470e212ce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9400000000-7ae0b50471ba90d5656cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-7580c3589d69535a4bb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-f9689d19a8a4fb34dc2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-f9689d19a8a4fb34dc2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f9689d19a8a4fb34dc2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0900000000-d519041b7fbf3920f7eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-0900000000-88e1671d699eb2ba3233View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-5900000000-c1dd9e6e9d3616306ddcView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
Synthesis Reference:Spallholz, 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)
External Links:
ResourceLink
CHEBI ID27812
HMDB IDHMDB04113
Pubchem Compound ID147004
Kegg IDC05689
ChemSpider ID129633
Wikipedia IDMethylselenocysteine
BioCyc IDNot Available

Enzymes

Protein Details
1. Gamma-glutamyltranspeptidase
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
(5-L-glutamyl)-peptide + an amino acid = peptide + 5-L-glutamyl amino acid
Gene Name:
ggt
Uniprot ID:
P18956
Molecular weight:
61768
Reactions
A (5-L-glutamyl)-peptide + an amino acid = a peptide + a 5-L-glutamyl amino acid.
Glutathione + H(2)O = L-cysteinylglycine + L-glutamate.
Protein Details
2. Cysteine desulfurase_
General function:
Involved in metabolic process
Specific function:
Cysteine desulfurases mobilize the sulfur from L- cysteine to yield L-alanine, an essential step in sulfur metabolism for biosynthesis of a variety of sulfur-containing biomolecules. Component of the suf operon, which is activated and required under specific conditions such as oxidative stress and iron limitation. Acts as a potent selenocysteine lyase in vitro, that mobilizes selenium from L-selenocysteine. Selenocysteine lyase activity is however unsure in vivo
Gene Name:
sufS
Uniprot ID:
P77444
Molecular weight:
44433
Reactions
L-cysteine + acceptor = L-alanine + S-sulfanyl-acceptor.
L-selenocysteine + reduced acceptor = selenide + L-alanine + acceptor.