You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 21:02:38 UTC
Update Date2020-02-26 21:42:24 UTC
HMDB IDHMDB0028821
Secondary Accession Numbers
  • HMDB28821
Metabolite Identification
Common NameGlutamylhistidine
DescriptionGlutamylhistidine is a dipeptide composed of glutamate and histidine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Glutamylhistidine is an incomplete breakdown product of protein digestion or protein catabolism. 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.
Structure
Data?1582753344
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 Molecular Weight284.272
Monoisotopic Molecular Weight284.112069631
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 Number21435-29-0
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
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
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-6.19Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility13.3 g/LALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-1290000000-d2ad2d572c51e3b304edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-6950000000-072c533bee41e3f72852Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-7c9a30851dab5f760bf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-6779e093e2a5a4da972bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fs9-2790000000-21e3d5a488358336daa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ke9-8900000000-7c09566c11ab8345931aSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. [PubMed:7911284 ]
  2. Kakimoto Y, Konishi H: Occurrence of gamma-glutamylhistidine in bovine brain. J Neurochem. 1976 Jun;26(6):1263-5. [PubMed:932730 ]
  3. Sovago I, Farkas E, Bertalan C, Lebkiri A, Kowalik-Jankowska T, Kozlowski H: Copper(II) complexes of dipeptides containing aspartyl, glutamyl, and histidyl residues in the side chain. J Inorg Biochem. 1993 Sep;51(4):715-26. [PubMed:7902418 ]