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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 IDHMDB0028893
Secondary Accession Numbers
  • HMDB28893
Metabolite Identification
Common NameHistidylproline
DescriptionHistidylproline is a dipeptide composed of histidine and proline. 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
Histidinyl-prolineChEBI
HistidylprolineChEBI
HPChEBI
L-His-L-proChEBI
H-P dipeptideHMDB
HP dipeptideHMDB
His-ProHMDB
Histidine proline dipeptideHMDB
Histidine-proline dipeptideHMDB
HistidinylprolineHMDB
Histidyl-prolineHMDB
L-Histidinyl-L-prolineHMDB
L-Histidyl-L-prolineHMDB
N-HistidinylprolineHMDB
N-HistidylprolineHMDB
N-L-Histidinyl-L-prolineHMDB
N-L-Histidyl-L-prolineHMDB
Chemical FormulaC11H16N4O3
Average Molecular Weight252.274
Monoisotopic Molecular Weight252.122240391
IUPAC Name(2S)-1-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxylic acid
Traditional Name(2S)-1-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxylic acid
CAS Registry Number20930-58-9
SMILES
N[C@@H](CC1=CNC=N1)C(=O)N1CCC[C@H]1C(O)=O
InChI Identifier
InChI=1S/C11H16N4O3/c12-8(4-7-5-13-6-14-7)10(16)15-3-1-2-9(15)11(17)18/h5-6,8-9H,1-4,12H2,(H,13,14)(H,17,18)/t8-,9-/m0/s1
InChI KeyLNCFUHAPNTYMJB-IUCAKERBSA-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
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Aralkylamine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • 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-3.88Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility20.6 g/LALOGPS
logP-2.6ALOGPS
logP-3.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.41ChemAxon
pKa (Strongest Basic)7.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.31 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.48 m³·mol⁻¹ChemAxon
Polarizability24.42 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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 ]
  3. 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 ID134260
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound152322
PDB IDNot Available
ChEBI ID74055
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jackson IM, Adelman LS, Munsat TL, Forte S, Lechan RM: Amyotrophic lateral sclerosis: thyrotropin-releasing hormone and histidyl proline diketopiperazine in the spinal cord and cerebrospinal fluid. Neurology. 1986 Sep;36(9):1218-23. [PubMed:3092130 ]