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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:03:23 UTC
Update Date2019-01-11 19:37:07 UTC
HMDB IDHMDB0029018
Secondary Accession Numbers
  • HMDB29018
Metabolite Identification
Common NameProlyl-Hydroxyproline
DescriptionProlyl-Hydroxyproline is a dipeptide composed of proline and hydroxyproline. 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?1547235427
Synonyms
ValueSource
Proline hydroxyproline dipeptideHMDB
L-Prolyl-L-hydroxyprolineHMDB
P-HP DipeptideHMDB
PHP DipeptideHMDB
pro-HProHMDB
Proline-hydroxyproline dipeptideHMDB
ProlylhydroxyprolineHMDB
Prolyl-4-hydroxyprolineMeSH
Chemical FormulaC10H16N2O4
Average Molecular Weight228.245
Monoisotopic Molecular Weight228.11100701
IUPAC Name4-hydroxy-1-(pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid
Traditional Name4-hydroxy-1-(pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC1CC(N(C1)C(=O)C1CCCN1)C(O)=O
InChI Identifier
InChI=1S/C10H16N2O4/c13-6-4-8(10(15)16)12(5-6)9(14)7-2-1-3-11-7/h6-8,11,13H,1-5H2,(H,15,16)
InChI KeyONPXCLZMBSJLSP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Organic nitrogen compound
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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-3.98Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility109 g/LALOGPS
logP-3ALOGPS
logP-4ChemAxon
logS-0.32ALOGPS
pKa (Strongest Acidic)3.54ChemAxon
pKa (Strongest Basic)9.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.87 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.37 m³·mol⁻¹ChemAxon
Polarizability22.29 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-9200000000-cefb6332c4f93d2283b3JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-9181000000-9dc13377c8269ef7020aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-2ab2a7cf304870a2e31fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-2900000000-61eb4bd5f2f1b2b9e6f2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1390000000-a90332787d698ae48b30JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-9520000000-9d66da5bd5b4f668794dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-eabc9dd778120ea68837JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0590000000-36eb40d7a5a8db7c8931JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05o0-3930000000-0a38333092801ce5d708JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0230-9200000000-d8bd00288e909bfe0b1bJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Sweat
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SweatDetected but not Quantified Infant (0-1 year old)Not Specifiedscreen-positive CF details
Associated Disorders and Diseases
Disease References
Cystic fibrosis
  1. Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
Associated OMIM IDs
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 Compound3952518
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lowry M, Hall DE, Brosnan JT: Metabolism of glycine- and hydroxyproline-containing peptides by the isolated perfused rat kidney. Biochem J. 1985 Jul 15;229(2):545-9. [PubMed:4038280 ]
  2. Kawaguchi T, Nanbu PN, Kurokawa M: Distribution of prolylhydroxyproline and its metabolites after oral administration in rats. Biol Pharm Bull. 2012;35(3):422-7. [PubMed:22382331 ]
  3. Lampiaho K, Nikkari T, Pikkarainen J, Karkkainen J, Kulonen E: Unexpected occurrence of prolylhydroxyproline during the analysis of collagen-bound carbohydrates by gas-liquid chromatography. J Chromatogr. 1972 Feb 2;64(2):211-8. [PubMed:5013106 ]
  4. Bienenstock HKIBRICK AC: Urinary excretion of prolylhydroxyproline in rheumatic diseases. Ann Rheum Dis. 1969 Jan;28(1):28-30. [PubMed:5305862 ]
  5. Codini M, Palmerini CA, Fini C, Lucarelli C, Floridi A: High-performance liquid chromatographic method for the determination of prolyl peptides in urine. J Chromatogr. 1991 Jan 4;536(1-2):337-41. [PubMed:2050773 ]
  6. KIBRICK AC, HASHIRO CQ, SCHULTZ RS, WALTERS MI, MILHORAT AT: PROLYLHYDROXYPROLINE IN URINE: ITS DETERMINATION AND OBSERVATIONS IN MUSCULAR DYSTROPHY. Clin Chim Acta. 1964 Oct;10:344-51. [PubMed:14219579 ]
  7. Hueckel HJ, Rogers QR: Prolylhydroxyproline absorption in hamsters. Can J Biochem. 1972 Jul;50(7):782-90. [PubMed:5050935 ]
  8. Kibrick AC, Power HL, Sevendal E, Milhorat AT: Prolylhydroxyproline in urine: improved method for detecting radioactivity with a scanner on full sheets of chromatography paper. Anal Biochem. 1968 Oct 24;25(1):40-5. [PubMed:5704756 ]
  9. KIBRICK AC, HASHIRO CQ, WALTERS MI, MILHORAT AT: DIKETOPIPERAZINE OF PROLYLHYDROXYPROLINE IN NORMAL HUMAN URINE. Proc Soc Exp Biol Med. 1965 Jan;118:62-4. [PubMed:14254586 ]
  10. Zhang A, Sun H, Han Y, Yuan Y, Wang P, Song G, Yuan X, Zhang M, Xie N, Wang X: Exploratory urinary metabolic biomarkers and pathways using UPLC-Q-TOF-HDMS coupled with pattern recognition approach. Analyst. 2012 Sep 21;137(18):4200-8. doi: 10.1039/c2an35780a. Epub 2012 Jul 31. [PubMed:22852134 ]