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Record Information
Version2.0
Created at2022-09-08 23:44:28 UTC
Updated at2022-09-08 23:44:28 UTC
NP-MRD IDNP0275858
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-4-methylpentanoic acid
DescriptionGamma-Glutamylleucine, also known as γ-L-glutamyl-L-leucine or γ-glu-leu, 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. Gamma-Glutamylleucine is a very strong basic compound (based on its pKa). Outside of the human body, gamma-Glutamylleucine has been detected, but not quantified in, soft-necked garlics. (2s)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-4-methylpentanoic acid is found in Phaseolus vulgaris and Vigna radiata. This could make gamma-glutamylleucine a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
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
L-gamma-Glu-L-leuHMDB
L-g-Glu-L-leuHMDB
L-Γ-glu-L-leuHMDB
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 Mass260.2869 Da
Monoisotopic Mass260.13722 Da
IUPAC Name(2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-methylpentanoic acid
Traditional Name(2S)-2-[(4S)-4-amino-4-carboxybutanamido]-4-methylpentanoic acid
CAS Registry NumberNot Available
SMILES
CC(C)C[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Phaseolus vulgarisLOTUS Database
Vigna radiataLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011171
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003617
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151023
PDB IDNot Available
ChEBI ID68433
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]