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Leucyl-Proline

July 21, 2017
Common Name

Leucyl-Proline Description

Leucyl-Proline is a dipeptide composed of leucine and proline. 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 HMDB28937 (Leucyl-Proline)

Synonyms

Value Source LeucylprolineMeSH

Chemical Formlia

C11H20N2O3 Average Molecliar Weight

228.2881 Monoisotopic Molecliar Weight

228.147392516 IUPAC Name

1-(2-amino-4-methylpentanoyl)pyrrolidine-2-carboxylic acid Traditional Name

leu-pro CAS Registry Number

Not Available SMILES

CC(C)CC(N)C(=O)N1CCCC1C(O)=O

InChI Identifier

InChI=1S/C11H20N2O3/c1-7(2)6-8(12)10(14)13-5-3-4-9(13)11(15)16/h7-9H,3-6,12H2,1-2H3,(H,15,16)

InChI Key

VTJUNIYRYIAIHF-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

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

    • Substituents

  • Alpha-dipeptide
  • Leucine or derivatives
  • 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
  • Carboxamide group
  • Amino acid or derivatives
  • Amino acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen 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-1.85Extrapolated

    Predicted Properties

    Property Value Source Water Solubility44.6 mg/mLALOGPS logP-0.78ALOGPS logP-1.9ChemAxon logS-0.71ALOGPS pKa (Strongest Acidic)3.92ChemAxon pKa (Strongest Basic)8.43ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area83.63 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity59.16 m3·mol-1ChemAxon Polarizability24.37 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

  • Feces
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details FecesDetected but not Quantified Not SpecifiedBoth

    Normal

  • 25486321

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details UrineDetected but not Quantified Adlit (>18 years old)Both

    Bladder cancer

  • 21799048

    • 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

    HMDB28937 Metagene Link

    HMDB28937 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: CCT196969

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Lacha J, Hubacek JA, Potmesil P, Viklicky O, Malek I, Vitko S: TGF-beta I gene polymorphism in heart transplant recipients–effect on renal function. Ann Transplant. 2001;6(1):39-43. [PubMed:11803605 ]
    2. Hebert EM, Mamone G, Picariello G, Raya RR, Savoy G, Ferranti P, Addeo F: Characterization of the pattern of alphas1- and beta-casein breakdown and release of a bioactive peptide by a cell envelope proteinase from Lactobacillus delbrueckii subsp. lactis CRL 581. Appl Environ Microbiol. 2008 Jun;74(12):3682-9. doi: 10.1128/AEM.00247-08. Epub 2008 Apr 18. [PubMed:18424544 ]
    3. Hebert EM, Raya RR, De Giori GS: Nutritional requirements and nitrogen-dependent regulation of proteinase activity of Lactobacillus helveticus CRL 1062. Appl Environ Microbiol. 2000 Dec;66(12):5316-21. [PubMed:11097908 ]
    4. Liu X, Jin W, Theil EC: Opening protein pores with chaotropes enhances Fe reduction and chelation of Fe from the ferritin biomineral. Proc Natl Acad Sci U S A. 2003 Apr 1;100(7):3653-8. Epub 2003 Mar 12. [PubMed:12634425 ]
    5. Cole A, Mendelblatt D, Aguayo J, Mathew A, Martin E, Vesely DL: Metastatic prostate cancer (with prostate-specific antigen of 9996) presenting as obstructive jaundice. Am J Med Sci. 2000 Feb;319(2):118-22. [PubMed:10698097 ]
    6. Zhang F, Jia Z, Gao P, Kong H, Li X, Lu X, Wu Y, Xu G: Metabonomics study of urine and plasma in depression and excess fatigue rats by ultra fast liquid chromatography coupled with ion trap-time of flight mass spectrometry. Mol Biosyst. 2010 May;6(5):852-61. doi: 10.1039/b914751a. Epub 2010 Feb 9. [PubMed:20567771 ]
    7. Martichonok V, Plouffe C, Storer AC, Menard R, Jones JB: Aziridine analogs of [[trans-(epoxysuccinyl)-L-leucyl]amino]-4-guanidinobutane (E-64) as inhibitors of cysteine proteases. J Med Chem. 1995 Aug 4;38(16):3078-85. [PubMed:7636871 ]
    8. Guedon E, Renault P, Ehrlich SD, Delorme C: Transcriptional pattern of genes coding for the proteolytic system of Lactococcus lactis and evidence for coordinated regulation of key enzymes by peptide supply. J Bacteriol. 2001 Jun;183(12):3614-22. [PubMed:11371525 ]
    9. Marugg JD, Meijer W, van Kranenburg R, Laverman P, Bruinenberg PG, de Vos WM: Medium-dependent regulation of proteinase gene expression in Lactococcus lactis: control of transcription initiation by specific dipeptides. J Bacteriol. 1995 Jun;177(11):2982-9. [PubMed:7768792 ]
    10. Zhang F, Jia Z, Gao P, Kong H, Li X, Chen J, Yang Q, Yin P, Wang J, Lu X, Li F, Wu Y, Xu G: Metabonomics study of atherosclerosis rats by ultra fast liquid chromatography coupled with ion trap-time of flight mass spectrometry. Talanta. 2009 Aug 15;79(3):836-44. doi: 10.1016/j.talanta.2009.05.010. Epub 2009 May 19. [PubMed:19576453 ]
    11. Pongracz E, Tordai A, Csornai M, Nagy Z: [Platelet glycoprotein IIb/IIIa (LeuPro 33) polymorphism in stroke patients]. Orv Hetil. 2001 Apr 15;142(15):781-5. [PubMed:11367863 ]
    12. Osugi T, Ukena K, Bentley GE, OBrien S, Moore IT, Wingfield JC, Tsutsui K: Gonadotropin-inhibitory hormone in Gambels white-crowned sparrow (Zonotrichia leucophrys gambelii): cDNA identification, transcript localization and functional effects in laboratory and field experiments. J Endocrinol. 2004 Jul;182(1):33-42. [PubMed:15225129 ]

    PMID: 9200664

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