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Prolyl-Hydroxyproline

July 21, 2017
Common Name

Prolyl-Hydroxyproline Description

Prolyl-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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Structure for HMDB29018 (Prolyl-Hydroxyproline)

Synonyms

Value Source Proline hydroxyproline dipeptideHMDB L-Prolyl-L-hydroxyprolineHMDB P-HP DipeptideHMDB PHP DipeptideHMDB pro-HProHMDB Proline-hydroxyproline dipeptideHMDB ProlylhydroxyprolineHMDB Prolyl-4-hydroxyprolineMeSH

Chemical Formlia

C10H16N2O4 Average Molecliar Weight

228.245 Monoisotopic Molecliar Weight

228.11100701 IUPAC Name

4-hydroxy-1-(pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid Traditional Name

4-hydroxy-1-(pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid CAS Registry Number

Not 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 Key

ONPXCLZMBSJLSP-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dipeptides Alternative Parents

  • N-acyl-alpha amino acids
  • Proline and derivatives
  • Alpha amino acid amides
  • Pyrrolidinecarboxamides
  • Pyrrolidine carboxylic acids
  • N-acylpyrrolidines
  • Tertiary carboxylic acid amides
  • Amino acids
  • Secondary alcohols
  • Monocarboxylic acids and derivatives
  • Dialkylamines
  • Carboxylic acids
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • 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

    • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Detected but not Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-3.98Extrapolated

    Predicted Properties

    Property Value Source Water Solubility109.0 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity54.37 m3·mol-1ChemAxon Polarizability22.29 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

    Not Available Biofluid Locations

  • Sweat

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details SweatDetected but not Quantified Infant (0-1 year old)Not Specifiedscreen-positive CF

  • Adriana Nori…

    • details

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    Not Available KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB29018 Metagene Link

    HMDB29018 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: I-CBP112

    References Synthesis Reference Not 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 ]

    PMID: 19474172

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