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Showing Compound Epsilon-(gamma-Glutamyl)-lysine (FDB023239)

Record Information
Version1.0
Creation date2011-09-21 00:26:46 UTC
Update date2015-07-21 06:57:36 UTC
Primary IDFDB023239
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEpsilon-(gamma-Glutamyl)-lysine
DescriptionIn non-diabetic kidney scarring the protein crosslinking enzyme tissue transglutaminase (tTg) has been implicated in the process by the formation of increased epsilon-(gamma-glutamyl)lysine bonds between ECM components in both experimental and human disease. Changes in tTg and epsilon-(gamma-glutamyl)lysine occur in human Diabetic nephropathy as well, the leading cause of chronic kidney failure. (PMID 15292688) In Parkinson's disease (PD), conformational changes in the alpha-synuclein monomer precede the formation of Lewy bodies. Both tTG and its substrate-characteristic N(epsilon)-(gamma-glutamyl)-lysine crosslink are increased in PD nigral dopamine neurons. (PMID 15001552) Expression of tissue transglutaminase (tTgase) and epsilon-(gamma-glutamyl)-lysine was present in all scarring of the blebs sites, being the main cause of failure in glaucoma filtration surgery. Transglutaminases are calcium-dependent enzymes that catalyze the posttranslational modification of proteins through an acyl transfer reaction between the gamma-carboxamide group of a peptide-bound glutaminyl residue and various amines. Covalent cross-linking using epsilon-(gamma-glutamyl)-lysine bonds is stable and resistant to enzymatic, chemical, and mechanical disruption. (PMID: 16936095) [HMDB]
CAS Number17105-15-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
epsilon-(gamma-L-Glutamyl)-L-lysineChEBI
epsilon-(L-gamma-Glutamyl)-L-lysineChEBI
gamma-Glu-epsilon-lysChEBI
gamma-Glutamyl-epsilon-lysineChEBI
L-gamma-Glutamyl-L-epsilon-lysineChEBI
N(6)-L-gamma-Glutamyl-L-lysineChEBI
N(epsilon)-(gamma-Glutamyl)-lysineChEBI
epsilon-(g-L-Glutamyl)-L-lysineGenerator
epsilon-(L-g-Glutamyl)-L-lysineGenerator
g-Glu-epsilon-lysGenerator
g-Glutamyl-epsilon-lysineGenerator
L-g-Glutamyl-L-epsilon-lysineGenerator
N(6)-L-g-Glutamyl-L-lysineGenerator
N(epsilon)-(g-Glutamyl)-lysineGenerator
epsilon-(g-Glutamyl)lysineGenerator
epsilon-(gamma-Glu)-lysHMDB, MeSH
epsilon-(gamma-Glutamyl)lysineHMDB
epsilon-(gamma-Glutamyl)lysine isodipeptideHMDB, MeSH
GGEL peptideMeSH, HMDB
N-epsilon-(gamma-L-Glutamyl)lysineMeSH, HMDB
epsilon-(gamma-Glutamyl)-lysineMeSH, HMDB
Epsilon-(g-Glutamyl)-lysineGenerator, HMDB
N6-L-gamma-Glutamyl-L-lysineHMDB
N6-L-γ-Glutamyl-L-lysineHMDB
Nepsilon(gamma-Glutamyl)lysineHMDB
Nepsilon-(gamma-Glutamyl)-L-lysineHMDB
Nε(γ-Glutamyl)lysineHMDB
Nε-(γ-Glutamyl)-L-lysineHMDB
epsilon-(gamma-L-Glutamyl)lysineHMDB
epsilonN-(gamma-L-Glutamyl)-L-lysineHMDB
γ-Glutamyl-ε-lysineHMDB
ε-(L-γ-Glutamyl)-L-lysineHMDB
ε-(γ-Glutamyl)lysineHMDB
ε-(γ-L-Glutamyl)-L-lysineHMDB
ε-(γ-L-Glutamyl)lysineHMDB
εN-(γ-L-Glutamyl)-L-lysineHMDB
Epsilon-(gamma-glu)-LYShmdb
Epsilon-(gamma-glutamyl)-lysinehmdb
Epsilon-(gamma-glutamyl)lysinehmdb
Epsilon-(gamma-glutamyl)lysine isodipeptidehmdb
Epsilon-(gamma-l-glutamyl)-l-lysinehmdb
N(epsilon)-(gamma-glutamyl)-lysinehmdb
Predicted Properties
PropertyValueSource
Water Solubility4.27 g/LALOGPS
logP-4ALOGPS
logP-6.1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)9.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.74 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity65.9 m³·mol⁻¹ChemAxon
Polarizability28.48 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H21N3O5
IUPAC name(2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid
InChI IdentifierInChI=1S/C11H21N3O5/c12-7(10(16)17)3-1-2-6-14-9(15)5-4-8(13)11(18)19/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1
InChI KeyJPKNLFVGUZRHOB-YUMQZZPRSA-N
Isomeric SMILESN[C@@H](CCCCNC(=O)CC[C@H](N)C(O)=O)C(O)=O
Average Molecular Weight275.3015
Monoisotopic Molecular Weight275.148120797
Classification
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
  • Medium-chain fatty acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Fatty amide
  • N-acyl-amine
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Primary aliphatic amine
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEpsilon-(gamma-Glutamyl)-lysine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-5940000000-d882bed3b5529ecff7f9Spectrum
Predicted GC-MSEpsilon-(gamma-Glutamyl)-lysine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-6639100000-f6ca1e086349e3426243Spectrum
Predicted GC-MSEpsilon-(gamma-Glutamyl)-lysine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0490000000-072f36ed9a7b3013d0592017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2930000000-392395a44df2ae8037f82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9500000000-6e7ed98ff09e19e298dc2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0190000000-58b6ca56f7cccfc512be2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aba-1690000000-fc6b7fb17538a52f8f982017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-9700000000-4409c236d141d58144272017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0190000000-87a26493d0e45ab09e992021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1930000000-3595f6a3ff829eac51de2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-8574eb2f5fa536d0c5ab2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-0390000000-6d00013244e4fc3d3d9b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9430000000-86b20a12b25ddf059e722021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9200000000-6238074e2599c8441ec52021-09-24View Spectrum
NMRNot Available
ChemSpider ID5378717
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID7015684
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03869
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference