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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 21:03:37 UTC
Update Date2020-02-26 21:42:53 UTC
HMDB IDHMDB0029085
Secondary Accession Numbers
  • HMDB29085
Metabolite Identification
Common NameTryptophyl-Histidine
DescriptionTryptophyl-Histidine is a dipeptide composed of tryptophan and histidine. It 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. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite.
Structure
Data?1582753373
Synonyms
ValueSource
L-Tryptophyl-L-histidineHMDB
TRP-HisHMDB
Tryptophan histidine dipeptideHMDB
Tryptophan-histidine dipeptideHMDB
TryptophylhistidineHMDB
W-H DipeptideHMDB
WH DipeptideHMDB
2-{[2-amino-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-3-(1H-imidazol-5-yl)propanoateGenerator
Tryptophyl-histidineMeSH
Chemical FormulaC17H19N5O3
Average Molecular Weight341.3645
Monoisotopic Molecular Weight341.148789499
IUPAC Name2-[2-amino-3-(1H-indol-3-yl)propanamido]-3-(1H-imidazol-5-yl)propanoic acid
Traditional Name2-[2-amino-3-(1H-indol-3-yl)propanamido]-3-(3H-imidazol-4-yl)propanoic acid
CAS Registry NumberNot Available
SMILES
NC(CC1=CNC2=C1C=CC=C2)C(=O)NC(CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C17H19N5O3/c18-13(5-10-7-20-14-4-2-1-3-12(10)14)16(23)22-15(17(24)25)6-11-8-19-9-21-11/h1-4,7-9,13,15,20H,5-6,18H2,(H,19,21)(H,22,23)(H,24,25)
InChI KeyKBUBZAMBIVEFEI-UHFFFAOYSA-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
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole or derivatives
  • Indole
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Benzenoid
  • Fatty acyl
  • Fatty amide
  • Substituted pyrrole
  • Imidazole
  • Pyrrole
  • Heteroaromatic compound
  • Azole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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-2.16Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP-1ALOGPS
logP-2.2ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)7.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.89 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity91.06 m³·mol⁻¹ChemAxon
Polarizability34.67 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0540-6920000000-c17af04c1308917726b2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-5901000000-e0bdcd052e096758c825Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0729000000-744517a95e603823581eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0900000000-0340fb7607eaab529979Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-1900000000-861f5682b6c8798543acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0129000000-549ab17fb43a647fcdfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ukm-2965000000-83e46b72263423310962Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-6900000000-ee04f81b0e7290fe4457Spectrum
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18218250
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. Joshi S, Ghosh I, Pokhrel S, Madler L, Nau WM: Interactions of amino acids and polypeptides with metal oxide nanoparticles probed by fluorescent indicator adsorption and displacement. ACS Nano. 2012 Jun 26;6(6):5668-79. doi: 10.1021/nn301669t. Epub 2012 May 22. [PubMed:22591378 ]