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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:50 UTC
Update Date2020-02-26 21:42:31 UTC
HMDB IDHMDB0028878
Secondary Accession Numbers
  • HMDB28878
Metabolite Identification
Common NameHistidylalanine
DescriptionHistidylalanine is a dipeptide composed of histidine and alanine. 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?1582753351
Synonyms
ValueSource
HAChEBI
HistidinoalanineChEBI
Histidinyl-alanineChEBI
HistidylalanineChEBI
L-His-L-alaChEBI
N-(2-Amino-2-carboxyethyl)histidineChEBI
HistidinylalanineMeSH
Histidinoalanine, (beta)-isomerMeSH
H-A dipeptideHMDB
HA dipeptideHMDB
His-AlaHMDB
Histidine alanine dipeptideHMDB
Histidine-alanine dipeptideHMDB
Histidyl-alanineHMDB
L-Histidinyl-L-alanineHMDB
L-Histidyl-L-alanineHMDB
N-HistidinylalanineHMDB
N-HistidylalanineHMDB
N-L-Histidinyl-L-alanineHMDB
N-L-Histidyl-L-alanineHMDB
Chemical FormulaC9H14N4O3
Average Molecular Weight226.236
Monoisotopic Molecular Weight226.106590327
IUPAC Name(2S)-2-[(2S)-2-amino-3-(1H-imidazol-5-yl)propanamido]propanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-3-(3H-imidazol-4-yl)propanamido]propanoic acid
CAS Registry Number16874-75-2
SMILES
C[C@H](NC(=O)[C@@H](N)CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C9H14N4O3/c1-5(9(15)16)13-8(14)7(10)2-6-3-11-4-12-6/h3-5,7H,2,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/t5-,7-/m0/s1
InChI KeyFRJIAZKQGSCKPQ-FSPLSTOPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alanine or derivatives
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-4.1Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility11.4 g/LALOGPS
logP-2.8ALOGPS
logP-3.9ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)8.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.1 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity55.36 m³·mol⁻¹ChemAxon
Polarizability22.2 ųChemAxon
Number of Rings1ChemAxon
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
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID91418
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101180
PDB IDNot Available
ChEBI ID73924
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nath M, Singh H, Eng G, Song X: New diorganotin(IV) derivatives of dipeptides: synthesis and characteristic spectral studies. Spectrochim Acta A Mol Biomol Spectrosc. 2008 Nov 15;71(2):529-36. doi: 10.1016/j.saa.2008.01.006. Epub 2008 Jan 11. [PubMed:18289925 ]
  2. Gucinski AC, Chamot-Rooke J, Nicol E, Somogyi A, Wysocki VH: Structural influences on preferential oxazolone versus diketopiperazine b(2+) ion formation for histidine analogue-containing peptides. J Phys Chem A. 2012 May 3;116(17):4296-304. doi: 10.1021/jp300262d. Epub 2012 Apr 24. [PubMed:22448972 ]