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Showing metabocard for N2-gamma-Glutamylglutamine (HMDB0011738)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-03-03 11:17:37 UTC
Update Date2020-02-26 21:35:45 UTC
HMDB IDHMDB0011738
Secondary Accession Numbers
  • HMDB11738
Metabolite Identification
Common NameN2-gamma-Glutamylglutamine
DescriptionN2-gamma-Glutamylglutamine, also known as gamma-L-Glu-L-Gln or L-gamma-glutamyl-L-glutamine, 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. N2-gamma-Glutamylglutamine is a very strong basic compound (based on its pKa). N2-gamma-Glutamylglutamine is a dipeptide obtained from the condensation of the gamma-carboxy group of glutamic acid with the alpha-amino group of glutamine. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Data?1582752945
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
γ-Glu-GlnHMDB, Generator
γ-L-Glu-L-GlnHMDB, Generator
γ-GlutamylglutamineHMDB, Generator
γ-L-Glutamyl-L-glutamineHMDB
L-γ-Glutamyl-L-glutamineHMDB
N2-γ-GlutamylglutamineHMDB, Generator
N2-L-γ-GlutamylglutamineHMDB
N2-L-γ-Glutamyl-L-glutamineHMDB
gamma-Glu-GlnHMDB, MeSH
gamma-L-Glu-L-GlnHMDB, ChEBI
gamma-GlutamylglutamineHMDB
gamma-L-Glutamyl-L-glutamineHMDB
L-gamma-Glutamyl-L-glutamineHMDB
N2-L-gamma-GlutamylglutamineHMDB
N2-L-gamma-Glutamyl-L-glutamineHMDB
N2-gamma-GlutamylglutamineHMDB
g-L-Glu-L-GlnGenerator
g-Glutamyl glutamineGenerator, HMDB
γ-glutamyl glutamineGenerator, HMDB
g-Glu-GlnGenerator
N2-g-GlutamylglutamineGenerator
g-GlutamylglutamineGenerator
Chemical FormulaC10H17N3O6
Average Molecular Weight275.2585
Monoisotopic Molecular Weight275.111735291
IUPAC Name(2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-carbamoylbutanoic acid
Traditional Name(2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-carbamoylbutanoic acid
CAS Registry Number10148-81-9
SMILES
N[C@@H](CCC(=O)N[C@@H](CCC(N)=O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C10H17N3O6/c11-5(9(16)17)1-4-8(15)13-6(10(18)19)2-3-7(12)14/h5-6H,1-4,11H2,(H2,12,14)(H,13,15)(H,16,17)(H,18,19)/t5-,6-/m0/s1
InChI KeyJBFYFLXEJFQWMU-WDSKDSINSA-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
  • N-acyl-l-alpha-amino acid
  • N-acyl-l-glutamine
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

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 Solubility6.17 g/LALOGPS
logP-3.6ALOGPS
logP-5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.93ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area172.81 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity61.2 m³·mol⁻¹ChemAxon
Polarizability26.12 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, Positivesplash10-001l-9560000000-a956f772592da08ac91bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9314100000-7288034a17d80463b7caSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0002-0900000000-aa0c06e268e954c25179Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a59-0290000000-53ebbfe26a1610c7d206Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-1790000000-8b9c77dbe3ee9bfa3360Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9600000000-7cf2074b159a06a79e69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0090000000-1e9b60fa2e6418acc332Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvm-3590000000-ebbac377891f30e322daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-3685d99d954b21693f1cSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 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
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 IDFDB028416
KNApSAcK IDNot Available
Chemspider ID133013
KEGG Compound IDC05283
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150914
PDB IDNot Available
ChEBI ID73707
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]