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Record Information
Version3.6
Creation Date2008-10-02 13:58:32 UTC
Update Date2016-02-11 01:20:03 UTC
HMDB IDHMDB10716
Secondary Accession NumbersNone
Metabolite Identification
Common NameGamma-Glutamyl-Se-methylselenocysteine
Descriptiongamma-Glutamyl-Se-methylselenocysteine is an intermediate in selenoamino acid metabolism(KEGG ID C05695). It is generated from Se-methyl-selenocysteine via the enzyme gamma-glutamyltranspeptidase [EC:2.3.2.2].
Structure
Thumb
SynonymsNot Available
Chemical FormulaC9H16N2O5Se
Average Molecular Weight311.19
Monoisotopic Molecular Weight312.02244346
IUPAC Name2-amino-4-{[1-carboxy-2-(methylselanyl)ethyl]carbamoyl}butanoic acid
Traditional Name2-amino-4-{[1-carboxy-2-(methylselanyl)ethyl]carbamoyl}butanoic acid
CAS Registry NumberNot Available
SMILES
C[Se]CC(NC(=O)CCC(N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C9H16N2O5Se/c1-17-4-6(9(15)16)11-7(12)3-2-5(10)8(13)14/h5-6H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)
InChI KeyInChIKey=IEFQLTYCECVOLL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma-glutamyl amino acids. These are dipeptides consisting of any C-terminal amino acid having a gamma-glutamyl residue attached at the N alpha-position.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma-glutamyl amino acids
Alternative Parents
Substituents
  • Gamma-glutamyl alpha-amino acid
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Selenoether
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organoselenium compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
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 Solubility31.1 mg/mLALOGPS
logP-3.1ALOGPS
logP-4.5ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.28ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity66.28 m3·mol-1ChemAxon
Polarizability24.81 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-1296000000-1d76833e7a815a1b8807View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02u1-2982000000-41d26e3850f274bc393cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9400000000-aa045eef0147244c51e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ox-7497000000-03ab4fa2f97826043d01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006y-4891000000-d87db74e9334bc8899f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9200000000-d18080502bbbf808125aView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
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 IDFDB027866
KNApSAcK IDNot Available
Chemspider ID389629
KEGG Compound IDC05695
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10716
Metagene LinkHMDB10716
METLIN IDNot Available
PubChem Compound440760
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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 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 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