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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-10-29 15:22:29 UTC
Update Date2020-02-26 21:34:36 UTC
HMDB IDHMDB0011176
Secondary Accession Numbers
  • HMDB0028996
  • HMDB11176
  • HMDB28996
Metabolite Identification
Common NamePhenylalanylhydroxyproline
DescriptionPhenylalanylhydroxyproline is a proteolytic breakdown product of collagen. It belongs to the family of peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by the formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. It is found in urine (PMID: 3782411 ).
Structure
Data?1582752876
Synonyms
ValueSource
(4R)-L-Phenylalanyl-4-hydroxy-L-prolineHMDB
L-Phenylalanyl-L-hydroxyprolineHMDB
Phenylalanyl-hydroxyprolineHMDB
PhenylalanylhydroxyprolineHMDB
Phenylalanine hydroxyproline dipeptideHMDB
Phenylalanine-hydroxyproline dipeptideHMDB
Chemical FormulaC14H18N2O4
Average Molecular Weight278.308
Monoisotopic Molecular Weight278.126657068
IUPAC Name(2S,4R)-1-[(2S)-2-amino-3-phenylpropanoyl]-4-hydroxypyrrolidine-2-carboxylic acid
Traditional Name(2S,4R)-1-[(2S)-2-amino-3-phenylpropanoyl]-4-hydroxypyrrolidine-2-carboxylic acid
CAS Registry Number90965-82-5
SMILES
N[C@@H](CC1=CC=CC=C1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O
InChI Identifier
InChI=1S/C14H18N2O4/c15-11(6-9-4-2-1-3-5-9)13(18)16-8-10(17)7-12(16)14(19)20/h1-5,10-12,17H,6-8,15H2,(H,19,20)/t10-,11+,12+/m1/s1
InChI KeyWJSNJMXOBDSZDL-WOPDTQHZSA-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
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary alcohol
  • Carboxamide group
  • Amino acid or derivatives
  • Amino acid
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen 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
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.72 g/LALOGPS
logP-2.6ChemAxon
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.42 m³·mol⁻¹ChemAxon
Polarizability27.87 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 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 IDFDB027948
KNApSAcK IDNot Available
Chemspider ID29322585
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480675
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. Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. [PubMed:3782411 ]