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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-02 13:58:32 UTC
Update Date2021-09-14 15:45:32 UTC
HMDB IDHMDB0010716
Secondary Accession Numbers
  • HMDB10716
Metabolite Identification
Common NameGamma-Glutamyl-Se-methylselenocysteine
DescriptionGamma-Glutamyl-Se-methylselenocysteine, also known as gamma-glutamyl-semc or GGMSC CPD, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Gamma-Glutamyl-Se-methylselenocysteine is a very strong basic compound (based on its pKa). Gamma-Glutamyl-Se-methylselenocysteine exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1582752865
Synonyms
ValueSource
g-Glutamyl-se-methylselenocysteineGenerator
Γ-glutamyl-se-methylselenocysteineGenerator
5-Glutamyl-se-methylselenocysteineHMDB
gamma-Glutamyl-semcHMDB
g-Glutamyl-semcHMDB
Γ-glutamyl-semcHMDB
GGMSC CPDHMDB
Glutamyl-se-methylselenocysteineHMDB
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 KeyIEFQLTYCECVOLL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Fatty amide
  • N-acyl-amine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Selenoether
  • Organoselenium compound
  • Primary aliphatic amine
  • Primary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

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 Solubility31.1 g/LALOGPS
logP10(-3.1) g/LALOGPS
logP10(-4.5) g/LChemAxon
logS10(-1) g/LALOGPS
pKa (Strongest Acidic)1.28ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity66.28 m³·mol⁻¹ChemAxon
Polarizability24.81 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
Gamma-Glutamyl-Se-methylselenocysteine,1TMS,#1C[Se]CC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C)C(=O)O2339.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,1TMS,#2C[Se]CC(NC(=O)CCC(N)C(=O)O)C(=O)O[Si](C)(C)C2337.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,1TMS,#3C[Se]CC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O)C(=O)O2409.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,1TMS,#4C[Se]CC(C(=O)O)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C2356.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TMS,#1C[Se]CC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2363.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TMS,#2C[Se]CC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O2400.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TMS,#3C[Se]CC(C(=O)O)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C)[Si](C)(C)C2359.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TMS,#4C[Se]CC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C2411.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TMS,#5C[Se]CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C2358.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TMS,#6C[Se]CC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O)[Si](C)(C)C2405.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TMS,#7C[Se]CC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2523.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,1TBDMS,#1C[Se]CC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2583.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,1TBDMS,#2C[Se]CC(NC(=O)CCC(N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2590.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,1TBDMS,#3C[Se]CC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O2636.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,1TBDMS,#4C[Se]CC(C(=O)O)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C(C)(C)C2604.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TBDMS,#1C[Se]CC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2826.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TBDMS,#2C[Se]CC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2857.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TBDMS,#3C[Se]CC(C(=O)O)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2828.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TBDMS,#4C[Se]CC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2859.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TBDMS,#5C[Se]CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C(C)(C)C2833.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TBDMS,#6C[Se]CC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2868.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Gamma-Glutamyl-Se-methylselenocysteine,2TBDMS,#7C[Se]CC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2967.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine GC-MS (Non-derivatized) - 70eV, Positivesplash10-008c-9740000000-59b05b3c41baff554d502017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9130300000-6ae8a4d0acc8b62f29dc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gamma-Glutamyl-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 - Gamma-Glutamyl-Se-methylselenocysteine 10V, Positive-QTOFsplash10-03xr-1296000000-1d76833e7a815a1b88072015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 20V, Positive-QTOFsplash10-02u1-2982000000-41d26e3850f274bc393c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 40V, Positive-QTOFsplash10-0a4i-9400000000-aa045eef0147244c51e62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 10V, Negative-QTOFsplash10-01ox-7497000000-03ab4fa2f97826043d012015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 20V, Negative-QTOFsplash10-006y-4891000000-d87db74e9334bc8899f62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 40V, Negative-QTOFsplash10-006x-9200000000-d18080502bbbf808125a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 10V, Negative-QTOFsplash10-03di-0029000000-5ac8065da136bd2d4be52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 20V, Negative-QTOFsplash10-0006-9642000000-640c0404517d357aa62a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 40V, Negative-QTOFsplash10-0006-9200000000-c463593b6c4e06750fb12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 10V, Positive-QTOFsplash10-03e9-0519000000-c64d1d10430502077b7f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 20V, Positive-QTOFsplash10-001i-5910000000-7c18554e94b7bb113d022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Glutamyl-Se-methylselenocysteine 40V, Positive-QTOFsplash10-0a4i-9800000000-93fde66ebaf182a700082021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027866
KNApSAcK IDNot Available
Chemspider ID389629
KEGG Compound IDC05695
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440760
PDB IDNot Available
ChEBI ID28776
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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