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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 14:15:06 UTC
Update Date2020-02-26 21:25:02 UTC
HMDB IDHMDB0004207
Secondary Accession Numbers
  • HMDB0028824
  • HMDB04207
  • HMDB28824
Metabolite Identification
Common NameGlutamyllysine
DescriptionGlutamyllysine is a dipeptide composed of glutamate and lysine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Glutamyllysine 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. The absorption of glutamyllysine is facilitated by the human intestinal oligopeptide transporter (PEPT1) (PMID 16759105 ).
Structure
Data?1582752302
Synonyms
ValueSource
E-KChEBI
EKChEBI
L-Glu-L-lysChEBI
N2-a-Glutamyl-lysineHMDB
N2-alpha-Glutamyl-lysineHMDB
N2-L-a-Glutamyl-lysineHMDB
N2-L-a-GlutamyllysineHMDB
N2-L-alpha-GlutamyllysineHMDB
Α-glu-lysHMDB
Α-L-glu-L-lysHMDB
Α-glutamyllysineHMDB
Α-L-glutamyl-L-lysineHMDB
L-Α-glutamyl-L-lysineHMDB
N2-Α-glutamyllysineHMDB
N2-Α-L-glutamyl-L-lysineHMDB
N2-L-Α-glutamyllysineHMDB
N2-L-Α-glutamyl-L-lysineHMDB
alpha-Glu-lysHMDB
alpha-L-Glu-L-lysHMDB
alpha-GlutamyllysineHMDB
alpha-L-Glutamyl-L-lysineHMDB
L-alpha-Glutamyl-L-lysineHMDB
N2-alpha-GlutamyllysineHMDB
N2-alpha-L-Glutamyl-L-lysineHMDB
N2-L-alpha-Glutamyl-L-lysineHMDB
Glu-lysHMDB
L-Glutamyl-L-lysineHMDB
N2-GlutamyllysineHMDB
N2-L-Glutamyl-L-lysineHMDB
Glutamyl-lysineHMDB
Glutamic acid lysine dipeptideHMDB
Glutamate lysine dipeptideHMDB
Glutamic acid-lysine dipeptideHMDB
Glutamate-lysine dipeptideHMDB
e-K DipeptideHMDB
EK dipeptideHMDB
N2-L-alpha-Glutamyl-lysineHMDB
GlutamyllysineHMDB
L-a-Glutamyl-L-lysineGenerator
Chemical FormulaC11H21N3O5
Average Molecular Weight275.3015
Monoisotopic Molecular Weight275.148120797
IUPAC Name(2S)-6-amino-2-[(2S)-2-amino-4-carboxybutanamido]hexanoic acid
Traditional NameL-α-glutamyl-L-lysine
CAS Registry Number5891-53-2
SMILES
NCCCC[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C11H21N3O5/c12-6-2-1-3-8(11(18)19)14-10(17)7(13)4-5-9(15)16/h7-8H,1-6,12-13H2,(H,14,17)(H,15,16)(H,18,19)/t7-,8-/m0/s1
InChI KeyBBBXWRGITSUJPB-YUMQZZPRSA-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
  • Glutamic acid or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Medium-chain fatty acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organic salt
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Amine
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic zwitterion
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

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 Solubility5.13 g/LALOGPS
logP-3.9ALOGPS
logP-6.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.74 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity65.9 m³·mol⁻¹ChemAxon
Polarizability28.33 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, Positivesplash10-0f89-7940000000-eca890c42ae6e7b1a500Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ec-9312000000-2d9010243a6fb8c34f9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-53bb2cbe87e51cdc8c3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uei-6980000000-2f0331667d540797338fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-f22342ddd828b5d10677Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-0d38cbef5f3e9b6ad2f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05c2-1790000000-01b3a430570ce2c6482bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-6900000000-e52f2a49ad96634a219cSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.23 +/- 0.04 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.15 +/- 0.07 uMAdult (>18 years old)BothDementia - unspecified cause details
Cerebrospinal Fluid (CSF)Detected and Quantified0.70 (0.66-0.74) uMAdult (>18 years old)BothHuntington's Disease details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Dementia
  1. Jeitner TM, Bogdanov MB, Matson WR, Daikhin Y, Yudkoff M, Folk JE, Steinman L, Browne SE, Beal MF, Blass JP, Cooper AJ: N(epsilon)-(gamma-L-glutamyl)-L-lysine (GGEL) is increased in cerebrospinal fluid of patients with Huntington's disease. J Neurochem. 2001 Dec;79(5):1109-12. [PubMed:11739625 ]
Huntington's disease
  1. Jeitner TM, Bogdanov MB, Matson WR, Daikhin Y, Yudkoff M, Folk JE, Steinman L, Browne SE, Beal MF, Blass JP, Cooper AJ: N(epsilon)-(gamma-L-glutamyl)-L-lysine (GGEL) is increased in cerebrospinal fluid of patients with Huntington's disease. J Neurochem. 2001 Dec;79(5):1109-12. [PubMed:11739625 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023334
KNApSAcK IDNot Available
Chemspider ID5378736
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7015704
PDB IDNot Available
ChEBI ID73521
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceKhosla, M. C.; Anand, Nitya. Synthesis of Na-(a-glutamyl and aspartyl)lysines. Journal of Scientific and Industrial Research, Section B: Physical Sciences (1962), 21B 287-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jeitner TM, Bogdanov MB, Matson WR, Daikhin Y, Yudkoff M, Folk JE, Steinman L, Browne SE, Beal MF, Blass JP, Cooper AJ: N(epsilon)-(gamma-L-glutamyl)-L-lysine (GGEL) is increased in cerebrospinal fluid of patients with Huntington's disease. J Neurochem. 2001 Dec;79(5):1109-12. [PubMed:11739625 ]
  2. Vig BS, Stouch TR, Timoszyk JK, Quan Y, Wall DA, Smith RL, Faria TN: Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding. J Med Chem. 2006 Jun 15;49(12):3636-44. [PubMed:16759105 ]
  3. De Kruyff RH, Ju ST, Laning J, Dorf ME: Analysis of T cell responses to poly-L(GluLys) at the clonal level. I. Presence of responsive clones in nonresponder mice. Eur J Immunol. 1987 Aug;17(8):1115-20. [PubMed:2441997 ]
  4. van Rossum EF, Koper JW, Huizenga NA, Uitterlinden AG, Janssen JA, Brinkmann AO, Grobbee DE, de Jong FH, van Duyn CM, Pols HA, Lamberts SW: A polymorphism in the glucocorticoid receptor gene, which decreases sensitivity to glucocorticoids in vivo, is associated with low insulin and cholesterol levels. Diabetes. 2002 Oct;51(10):3128-34. [PubMed:12351458 ]
  5. Russcher H, van Rossum EF, de Jong FH, Brinkmann AO, Lamberts SW, Koper JW: Increased expression of the glucocorticoid receptor-A translational isoform as a result of the ER22/23EK polymorphism. Mol Endocrinol. 2005 Jul;19(7):1687-96. Epub 2005 Mar 3. [PubMed:15746190 ]