Np mrd loader

Record Information
Version2.0
Created at2022-05-12 15:14:45 UTC
Updated at2022-05-12 15:14:45 UTC
NP-MRD IDNP0136446
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlutamylhistidine
DescriptionGlutamylhistidine, also known as glu-his or e-H dipeptide, 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. Glutamylhistidine is a dipeptide composed of glutamate and histidine, and is a proteolytic breakdown product of larger proteins. 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. Glutamylhistidine is a very strong basic compound (based on its pKa). These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Glutamylhistidine was first documented in 1976 (PMID: 932730). Glutamylhistidine is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 7911284).
Structure
Thumb
Synonyms
ValueSource
e-H DipeptideHMDB
EH dipeptideHMDB
Glu-hisHMDB
Glutamate histidine dipeptideHMDB
Glutamate-histidine dipeptideHMDB
L-Glutamyl-L-histidineHMDB
Α-glu-hisHMDB
Α-L-glu-L-hisHMDB
Α-glutamylhistidineHMDB
Α-L-glutamyl-L-histidineHMDB
L-Α-glutamyl-L-histidineHMDB
N-Α-glutamylhistidineHMDB
N-Α-L-glutamyl-L-histidineHMDB
N-L-Α-glutamylhistidineHMDB
N-L-Α-glutamyl-L-histidineHMDB
alpha-Glu-hisHMDB
alpha-L-Glu-L-hisHMDB
alpha-GlutamylhistidineHMDB
alpha-L-Glutamyl-L-histidineHMDB
L-alpha-Glutamyl-L-histidineHMDB
N-alpha-GlutamylhistidineHMDB
N-alpha-L-Glutamyl-L-histidineHMDB
N-L-alpha-GlutamylhistidineHMDB
N-L-alpha-Glutamyl-L-histidineHMDB
L-Glu-L-hisHMDB
N-GlutamylhistidineHMDB
N-L-Glutamyl-L-histidineHMDB
Glutamyl-histidineHMDB
Glutamic acid histidine dipeptideHMDB
Glutamic acid-histidine dipeptideHMDB
GlutamylhistidineHMDB
(4S)-4-Amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}butanoateGenerator
Chemical FormulaC11H16N4O5
Average Mass284.2720 Da
Monoisotopic Mass284.11207 Da
IUPAC Name(4S)-4-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid
Traditional Name(4S)-4-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid
CAS Registry NumberNot Available
SMILES
N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC=N1)C(O)=O
InChI Identifier
InChI=1S/C11H16N4O5/c12-7(1-2-9(16)17)10(18)15-8(11(19)20)3-6-4-13-5-14-6/h4-5,7-8H,1-3,12H2,(H,13,14)(H,15,18)(H,16,17)(H,19,20)/t7-,8-/m0/s1
InChI KeyHKTRDWYCAUTRRL-YUMQZZPRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
  • Histidine or derivatives
  • 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
  • Imidazolyl carboxylic acid derivative
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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-3ALOGPS
logP-6.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)8.46ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area158.4 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity65.58 m³·mol⁻¹ChemAxon
Polarizability27.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0028821
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8097510
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9921875
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sandberg M, Li X, Folestad S, Weber SG, Orwar O: Liquid chromatographic determination of acidic beta-aspartyl and gamma-glutamyl peptides in extracts of rat brain. Anal Biochem. 1994 Feb 15;217(1):48-61. doi: 10.1006/abio.1994.1082. [PubMed:7911284 ]
  2. Kakimoto Y, Konishi H: Occurrence of gamma-glutamylhistidine in bovine brain. J Neurochem. 1976 Jun;26(6):1263-5. doi: 10.1111/j.1471-4159.1976.tb07016.x. [PubMed:932730 ]