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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:53 UTC
Update Date2020-02-26 21:42:32 UTC
HMDB IDHMDB0028892
Secondary Accession Numbers
  • HMDB28892
Metabolite Identification
Common NameHistidylphenylalanine
DescriptionHistidylphenylalanine is a dipeptide composed of histidine and phenylalanine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Data?1582753352
Synonyms
ValueSource
(2S)-2-{[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino}-3-phenylpropanoic acidChEBI
H-FChEBI
H-F DipeptideChEBI
HFChEBI
HF DipeptideChEBI
Histidine phenylalanine dipeptideChEBI
HistidylphenylalanineChEBI
N-Histidyl-phenylalanineChEBI
N-L-Histidyl-L-phenylalanineChEBI
(2S)-2-{[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino}-3-phenylpropanoateGenerator
PhenylalanylhistidineMeSH
Phe-hisMeSH
His-PheHMDB
Histidine-phenylalanine dipeptideHMDB
Histidinyl-phenylalanineHMDB
HistidinylphenylalanineHMDB
Histidyl-phenylalanineHMDB
L-His-L-PheHMDB
L-Histidinyl-L-phenylalanineHMDB
L-Histidyl-L-phenylalanineHMDB
N-HistidinylphenylalanineHMDB
N-HistidylphenylalanineHMDB
N-L-Histidinyl-L-phenylalanineHMDB
Chemical FormulaC15H18N4O3
Average Molecular Weight302.334
Monoisotopic Molecular Weight302.137890456
IUPAC Name(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanoic acid
CAS Registry Number16874-81-0
SMILES
N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C15H18N4O3/c16-12(7-11-8-17-9-18-11)14(20)19-13(15(21)22)6-10-4-2-1-3-5-10/h1-5,8-9,12-13H,6-7,16H2,(H,17,18)(H,19,20)(H,21,22)/t12-,13-/m0/s1
InChI KeyXMAUFHMAAVTODF-STQMWFEESA-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
  • Phenylalanine or derivatives
  • Histidine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.3Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility0.72 g/LALOGPS
logP-1.6ALOGPS
logP-2.1ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)7.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.1 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity79.41 m³·mol⁻¹ChemAxon
Polarizability30.79 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  2. 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. [PubMed:27275383 ]
  3. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID134148
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound152198
PDB IDNot Available
ChEBI ID141438
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sigman JA, Kim HK, Zhao X, Carey JR, Lu Y: The role of copper and protons in heme-copper oxidases: kinetic study of an engineered heme-copper center in myoglobin. Proc Natl Acad Sci U S A. 2003 Apr 1;100(7):3629-34. Epub 2003 Mar 24. [PubMed:12655052 ]
  2. Osz K, Varnagy K, Suli-Vargha H, Csampay A, Sanna D, Micera G, Sovago I: Acid-base properties and copper(II) complexes of dipeptides containing histidine and additional chelating bis(imidazol-2-yl) residues. J Inorg Biochem. 2004 Jan;98(1):24-32. [PubMed:14659629 ]
  3. Reddy PR, Mohan SK, Rao KS: Ternary zinc(II)-dipeptide complexes for the hydrolytic cleavage of DNA at physiological pH. Chem Biodivers. 2005 May;2(5):672-83. [PubMed:17192010 ]