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Lysyl-Hydroxyproline

July 21, 2017
Common Name

Lysyl-Hydroxyproline Description

Lysyl-Hydroxyproline is a dipeptide composed of lysine 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

MOLSDFPDBSMILESInChI

Structure for HMDB28952 (Lysyl-Hydroxyproline)

Synonyms

Value Source Lysine hydroxyproline dipeptideHMDB K-HP DipeptideHMDB KHP DipeptideHMDB L-Lysyl-L-hydroxyprolineHMDB Lys-hproHMDB Lysine-hydroxyproline dipeptideHMDB LysylhydroxyprolineHMDB

Chemical Formlia

C11H21N3O4 Average Molecliar Weight

259.3021 Monoisotopic Molecliar Weight

259.153206175 IUPAC Name

1-(2,6-diaminohexanoyl)-4-hydroxypyrrolidine-2-carboxylic acid Traditional Name

1-(2,6-diaminohexanoyl)-4-hydroxypyrrolidine-2-carboxylic acid CAS Registry Number

Not Available SMILES

NCCCCC(N)C(=O)N1CC(O)CC1C(O)=O

InChI Identifier

InChI=1S/C11H21N3O4/c12-4-2-1-3-8(13)10(16)14-6-7(15)5-9(14)11(17)18/h7-9,15H,1-6,12-13H2,(H,17,18)

InChI Key

BFDLYDRHDPSQHM-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
  • Pyrrolidine carboxylic acids
  • N-acylpyrrolidines
  • Tertiary carboxylic acid amides
  • Amino acids
  • Secondary alcohols
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Monoalkylamines
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Alpha-dipeptide
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Proline or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary alcohol
  • Carboxamide group
  • Amino acid or derivatives
  • Amino acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound

    • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected 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-4.4Extrapolated

    Predicted Properties

    Property Value Source Water Solubility29.8 mg/mLALOGPS logP-3.4ALOGPS logP-4.5ChemAxon logS-0.94ALOGPS pKa (Strongest Acidic)3.53ChemAxon pKa (Strongest Basic)10.21ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area129.88 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity64.11 m3·mol-1ChemAxon Polarizability26.87 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

    Not Available Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available 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

    HMDB28952 Metagene Link

    HMDB28952 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: PNU-74654

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    PMID: 20228179

    Last updated on