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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-06 21:03:53 UTC
Update Date2019-07-23 06:03:25 UTC
HMDB IDHMDB0029147
Secondary Accession Numbers
  • HMDB29147
Metabolite Identification
Common NameN-gamma-Glutamylglutamine
DescriptionN-gamma-Glutamylglutamine is a dipeptide obtained from condensation of the gamma-carboxy group of glutamic acid with the side-chain amide group of glutamine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Data?1563861805
Synonyms
ValueSource
Bis-g-glutamylamineGenerator
Bis-γ-glutamylamineGenerator
γ-Glu-GlnCAS
γ-L-Glu-L-GlnCAS
γ-GlutamylglutamineCAS
γ-L-Glutamyl-L-glutamineCAS
L-γ-Glutamyl-L-glutamineCAS
N-γ-GlutamylglutamineCAS
N-L-γ-GlutamylglutamineCAS
N-L-γ-Glutamyl-L-glutamineCAS
gamma-Glu-GlnCAS
gamma-L-Glu-L-GlnCAS
gamma-GlutamylglutamineCAS
gamma-L-Glutamyl-L-glutamineCAS
L-gamma-Glutamyl-L-glutamineCAS
N-L-gamma-GlutamylglutamineCAS
N-L-gamma-Glutamyl-L-glutamineCAS
N-gamma-GlutamylglutamineCAS
Chemical FormulaC10H17N3O6
Average Molecular Weight275.261
Monoisotopic Molecular Weight275.111735279
IUPAC Name(2S)-2-amino-5-[(4S)-4-amino-4-carboxybutanamido]-5-oxopentanoic acid
Traditional Name(2S)-2-amino-5-[(4S)-4-amino-4-carboxybutanamido]-5-oxopentanoic acid
CAS Registry Number1466-50-8
SMILES
N[C@@H](CCC(=O)NC(=O)CC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C10H17N3O6/c11-5(9(16)17)1-3-7(14)13-8(15)4-2-6(12)10(18)19/h5-6H,1-4,11-12H2,(H,16,17)(H,18,19)(H,13,14,15)/t5-,6-/m0/s1
InChI KeyFCWNOQOVMGNKNG-WDSKDSINSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glutamine and derivatives. These 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
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • N-acyl-amine
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Amino acid
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-5.63Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility4.2 g/LALOGPS
logP-3.9ALOGPS
logP-7ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.64ChemAxon
pKa (Strongest Basic)9.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area172.81 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity61.32 m³·mol⁻¹ChemAxon
Polarizability26.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-003r-0590000000-2f7edd0cd4abe6907109JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2940000000-5bed090f9875142a4953JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9300000000-61d8fdac4c7d6aff98dcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-f078bebea2b6c00a7d74JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i1-1790000000-3b508fc276d3694311f5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0097-9400000000-b7441b7b8a4a9964ba1aJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3-8 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.46 +/- 0.47 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.5 uMAdult (>18 years old)Not SpecifiedGamma-glutamyltransferase deficiency details
BloodDetected and Quantified117.00 (20.00-214.00) uMAdult (>18 years old)BothHyperammonemia details
Cerebrospinal Fluid (CSF)Detected and Quantified2.07 +/- 0.52 uMAdult (>18 years old)BothSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified258.00 uMAdult (>18 years old)BothHyperammonemia details
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)BothIron deficiency details
Associated Disorders and Diseases
Disease References
Gamma-glutamyltransferase deficiency
  1. Hammond JW, Potter M, Sim KG, Wilcken B: Reduced glutathione, gamma-glutamylcysteine, cysteine and gamma-glutamylglutamine in gamma-glutamyltransferase deficiency. J Inherit Metab Dis. 1999 May;22(3):235-9. [PubMed:10384376 ]
Hyperammonemia
  1. Hammond JW, Potter M, Truscott R, Wilcken B: gamma-Glutamylglutamine identified in plasma and cerebrospinal fluid from hyperammonaemic patients. Clin Chim Acta. 1990 Dec 24;194(2-3):173-83. [PubMed:2093471 ]
Schizophrenia
  1. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ]
Crohn's disease
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Iron deficiency
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21122973
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available