You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-10-29 15:22:04 UTC
Update Date2017-12-07 18:36:26 UTC
HMDB IDHMDB0011175
Secondary Accession Numbers
  • HMDB0028937
  • HMDB11175
  • HMDB28937
Metabolite Identification
Common NameLeucylproline
DescriptionL-leucyl-l-proline is a proteolytic breakdown product of larger proteins. 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 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
Thumb
Synonyms
ValueSource
LeucylprolineMeSH
Chemical FormulaC11H20N2O3
Average Molecular Weight228.2881
Monoisotopic Molecular Weight228.147392516
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
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 KeyVTJUNIYRYIAIHF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentDipeptides
Alternative Parents
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
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01px-9600000000-a4c6468eb25edaa2a713View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01wr-9430000000-72f289fdf0c486dc887dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-1290000000-a7d4bfdd98e774a63ec6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ti-9320000000-11c16428d6d853c82e2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9000000000-1f0cc62f9745c1b92db3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0690000000-abfdecce35ead141486fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-3930000000-da0f5e7072ac2161b71eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03mj-9600000000-7be81d5eb7b4a169cabcView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Not SpecifiedBoth
    Normal
    details
    UrineDetected and Quantified0.03 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Adult (>18 years old)Both
    Bladder cancer
    details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB027947
    KNApSAcK IDNot Available
    Chemspider ID3196828
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound44369311
    PDB IDNot Available
    ChEBI ID356659
    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 ]
    2. Guo K, Li L: Differential 12C-/13C-isotope dansylation labeling and fast liquid chromatography/mass spectrometry for absolute and relative quantification of the metabolome. Anal Chem. 2009 May 15;81(10):3919-32. doi: 10.1021/ac900166a. [PubMed:19309105 ]
    3. 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 ]
    4. 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 ]
    5. 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 ]
    6. 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 ]
    7. 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 ]
    8. 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 ]
    9. 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 ]
    10. 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 ]
    11. 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 ]
    12. 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 ]
    13. 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 ]
    14. Osugi T, Ukena K, Bentley GE, O'Brien S, Moore IT, Wingfield JC, Tsutsui K: Gonadotropin-inhibitory hormone in Gambel's 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 ]
    15. Huang Z, Lin L, Gao Y, Chen Y, Yan X, Xing J, Hang W: Bladder cancer determination via two urinary metabolites: a biomarker pattern approach. Mol Cell Proteomics. 2011 Oct;10(10):M111.007922. doi: 10.1074/mcp.M111.007922. Epub 2011 Jul 28. [PubMed:21799048 ]
    16. Xu W, Chen D, Wang N, Zhang T, Zhou R, Huan T, Lu Y, Su X, Xie Q, Li L, Li L: Development of high-performance chemical isotope labeling LC-MS for profiling the human fecal metabolome. Anal Chem. 2015 Jan 20;87(2):829-36. doi: 10.1021/ac503619q. Epub 2014 Dec 25. [PubMed:25486321 ]