L-alpha-Glutamyl-L-lysine (CHEM035651)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:57:33 UTC
Update Date2016-11-09 01:21:21 UTC
Accession NumberCHEM035651
Identification
Common NameL-alpha-Glutamyl-L-lysine
ClassSmall Molecule
DescriptionA dipeptide composed of L-glutamic acid and L-lysine joined by a peptide linkage.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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, Generator
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
GlutamyllysineHMDB
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
L-a-Glutamyl-L-lysineGenerator, HMDB
Chemical FormulaC11H21N3O5
Average Molecular Mass275.302 g/mol
Monoisotopic Mass275.148 g/mol
CAS Registry Number5891-53-2
IUPAC Name(2S)-6-amino-2-[(2S)-2-amino-4-carboxybutanamido]hexanoic acid
Traditional NameL-α-glutamyl-L-lysine
SMILESNCCCC[C@H](NC(=O)[C@@H](N)CCC(O)=O)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0690000000-0e960775d4beeef605acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-7970000000-4863aabdbd3b7a54ad3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9100000000-15e321d845df9b1acad5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0090000000-1c9639c3ad4f25da3f58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i1-1970000000-4010465b012a24ce2961Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-1e5789d6c070ee5bee99Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004207
FooDB IDFDB023334
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID5378736
ChEBI ID73521
PubChem Compound ID7015704
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Khosla, 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.