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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 13:58:55 UTC
Update Date2020-02-26 21:25:02 UTC
HMDB IDHMDB0004195
Secondary Accession Numbers
  • HMDB04195
Metabolite Identification
Common Name5-L-Glutamyl-taurine
Description5-L-Glutamyl-taurine, also known as gamma-glutamyltaurine or glutaurina, belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 5-L-Glutamyl-taurine is a very strong basic compound (based on its pKa). 5-L-Glutamyl-taurine exists in all living organisms, ranging from bacteria to humans. 5-L-glutamyl-taurine can be biosynthesized from taurine; which is mediated by the enzyme Gamma-glutamyltransferase 6. In humans, 5-L-glutamyl-taurine is involved in taurine and hypotaurine metabolism.
Structure
Data?1582752302
Synonyms
ValueSource
5-Glutamyl-taurineChEBI
gamma-GlutamyltaurineChEBI
gamma-GTChEBI
gamma-L-GlutamyltaurineChEBI
GlutaurinaChEBI
GlutaurinumChEBI
LitoralonChEBI
GlutaurineKegg
g-GlutamyltaurineGenerator
Γ-glutamyltaurineGenerator
g-GTGenerator
Γ-GTGenerator
g-L-GlutamyltaurineGenerator
Γ-L-glutamyltaurineGenerator
alpha-Glutamyl taurineHMDB
gamma-L-Glutamyl-taurineHMDB
GlautaurineHMDB
GlutaurinHMDB
Glutaurin, (D)-isomerHMDB
alpha-GlutamyltaurineHMDB
Chemical FormulaC7H14N2O6S
Average Molecular Weight254.261
Monoisotopic Molecular Weight254.05725688
IUPAC Name(2S)-2-amino-4-[(2-sulfoethyl)carbamoyl]butanoic acid
Traditional Name(2S)-2-amino-4-[(2-sulfoethyl)carbamoyl]butanoic acid
CAS Registry NumberNot Available
SMILES
N[C@@H](CCC(=O)NCCS(O)(=O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H14N2O6S/c8-5(7(11)12)1-2-6(10)9-3-4-16(13,14)15/h5H,1-4,8H2,(H,9,10)(H,11,12)(H,13,14,15)/t5-/m0/s1
InChI KeyWGXUDTHMEITUBO-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine and derivatives
Alternative Parents
Substituents
  • Glutamine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Fatty amide
  • N-acyl-amine
  • Fatty acid
  • Fatty acyl
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Alkanesulfonic acid
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary amine
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Process

Naturally occurring process:

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 Solubility9.99 g/LALOGPS
logP-2.3ALOGPS
logP-3.6ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area146.79 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity52.69 m³·mol⁻¹ChemAxon
Polarizability23.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0536-9620000000-a538eb9e6c595cef5a4cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fu-9551000000-f0e6775174afe08371f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1690000000-5a8d4b6641b218cf8506Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-2920000000-360e2479ab5fa4d3ed08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9400000000-bf155960a2593c2884d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2290000000-148d482f4c7749eb7d10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ff9-7970000000-1c9d1a98595ca5fdde6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008c-9200000000-e084fb39cebaaa6d3226Spectrum
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 IDFDB023332
KNApSAcK IDNot Available
Chemspider ID62003
KEGG Compound IDC05844
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlutaurine
METLIN IDNot Available
PubChem Compound68759
PDB IDNot Available
ChEBI ID27694
Food Biomarker OntologyNot Available
VMH 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 + Taurine → Peptide + 5-L-Glutamyl-taurinedetails
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 + Taurine → Peptide + 5-L-Glutamyl-taurinedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Not Available
Gene Name:
CSAD
Uniprot ID:
Q9Y600
Molecular weight:
55022.79
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 + Taurine → Peptide + 5-L-Glutamyl-taurinedetails
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 + Taurine → Peptide + 5-L-Glutamyl-taurinedetails