gamma-L-Glutamyl-L-leucine (CHEM025329)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:19:34 UTC
Update Date2016-11-09 01:18:03 UTC
Accession NumberCHEM025329
Identification
Common Namegamma-L-Glutamyl-L-leucine
ClassSmall Molecule
DescriptionA glutamyl-L-amino acid obtained by formal condensation of the gamma-carboxy group of glutamic acid with the amino group of leucine.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
L-gamma-Glu-L-leuChEBI
L-g-Glu-L-leuGenerator
L-Γ-glu-L-leuGenerator
g-GlutamylleucineGenerator
Γ-glutamylleucineGenerator
Γ-glu-leuHMDB
Γ-L-glu-L-leuHMDB
Γ-L-glutamyl-L-leucineHMDB
L-Γ-glutamyl-L-leucineHMDB
N-Γ-glutamylleucineHMDB
N-L-Γ-glutamylleucineHMDB
N-L-Γ-glutamyl-L-leucineHMDB
gamma-Glu-leuHMDB
gamma-L-Glu-L-leuHMDB
gamma-L-Glutamyl-L-leucineHMDB
L-gamma-Glutamyl-L-leucineHMDB
N-L-gamma-GlutamylleucineHMDB
N-L-gamma-Glutamyl-L-leucineHMDB
g-L-Glutamyl-L-leucineHMDB
gamma-Glutamyl-leucineHMDB
N-Γ-L-glutamyl-L-leucineHMDB
N-gamma-GlutamylleucineHMDB
N-gamma-L-Glutamyl-L-leucineHMDB
g-Glu-leuHMDB
gamma-GlutamylleucineHMDB, MeSH
Chemical FormulaC11H20N2O5
Average Molecular Mass260.287 g/mol
Monoisotopic Mass260.137 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-methylpentanoic acid
Traditional Name(2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-methylpentanoic acid
SMILESCC(C)C[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O
InChI IdentifierInChI=1S/C11H20N2O5/c1-6(2)5-8(11(17)18)13-9(14)4-3-7(12)10(15)16/h6-8H,3-5,12H2,1-2H3,(H,13,14)(H,15,16)(H,17,18)/t7-,8-/m0/s1
InChI KeyMYFMARDICOWMQP-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
  • Gamma-glutamyl alpha-amino acid
  • Glutamine or derivatives
  • Leucine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Secondary 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
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • 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 Solubility4.48 g/LALOGPS
logP-2.6ALOGPS
logP-2.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity62.26 m³·mol⁻¹ChemAxon
Polarizability26.29 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, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001r-9700000000-ab8893b60e98e1001ce4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-003r-0910000000-aabd82b48efea4e12f3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-2790000000-5c22f609f3419b66f92cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-5920000000-c6ba6e3d51cd69c276b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9300000000-b9930e2710d2f35bd3a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-3f84380e6a3d8cd32665Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05nb-2960000000-9496cdad8fb51a2cf83aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008c-9400000000-a22f3c19c909bd949fb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0290000000-bc2325e96da07defc0e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9500000000-1ff58fb786217f5dab60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9000000000-a2e54d332ec42ec1dc2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-7c126c4b070de4bd4070Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1920000000-c5a4a154fcf2902b660fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-39be620cfa483376cf2dSpectrum
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 IDHMDB0011171
FooDB IDFDB003617
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID133115
ChEBI ID68433
PubChem Compound ID151023
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
2. Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45.
3. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016.
4. Zheng Y, Yu B, Alexander D, Steffen LM, Boerwinkle E: Human metabolome associates with dietary intake habits among African Americans in the atherosclerosis risk in communities study. Am J Epidemiol. 2014 Jun 15;179(12):1424-33. doi: 10.1093/aje/kwu073. Epub 2014 May 6.
5. 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.