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Record Information
Version3.6
Creation Date2006-08-13 11:13:59 UTC
Update Date2016-02-11 01:06:34 UTC
HMDB IDHMDB04113
Secondary Accession NumbersNone
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. 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
Synonyms
ValueSource
L-MethylselenocysteineChEBI
Methyl-L-selenocysteineChEBI
MethylselenocysteineChEBI
Se-methyl-seleno-L-cysteineChEBI
Se-methyl-selenocysteineChEBI
Se-methylselenocysteineChEBI
Selenium methyl cysteineChEBI
Selenium-methylselenocystineChEBI
SelenohomocysteineChEBI
SelenomethylselenocysteineChEBI
(2R)-2-amino-3-MethylselanylpropanoateGenerator
3-(methylseleno)-L-AlanineHMDB
Se-methyl-L-selenocysteineHMDB
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 KeyInChIKey=XDSSPSLGNGIIHP-VKHMYHEASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino 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 Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility156.0 mg/mLALOGPS
logP-2.8ALOGPS
logP-3.5ChemAxon
logS-0.07ALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.2 m3·mol-1ChemAxon
Polarizability12.89 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-MS (1 TMS)splash10-000i-2900000000-584579d62a5c494d1ad4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0i00-1960000000-c1d9d3d6c03ef447c682View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Selenoamino Acid MetabolismSMP00029map00450
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012599
KNApSAcK IDC00001382
Chemspider ID129633
KEGG Compound IDC05689
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04113
Metagene LinkHMDB04113
METLIN ID7019
PubChem Compound147004
PDB IDNot Available
ChEBI ID27812
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. [15213307 ]

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