Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-10-29 15:22:04 UTC
Update Date2021-09-14 15:46:19 UTC
HMDB IDHMDB0011175
Secondary Accession Numbers
  • HMDB0028937
  • HMDB11175
  • HMDB28937
Metabolite Identification
Common NameLeucylproline
DescriptionLeucylproline, also known as L-leu-L-pro or LP, 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. Leucylproline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Leucylproline.
Structure
Data?1582752876
Synonyms
ValueSource
L-Leu-L-proChEBI
L-PChEBI
LPChEBI
1-L-Leucyl-L-prolineHMDB
L-Leucyl-L-prolineHMDB
L-p DipeptideHMDB
LP DipeptideHMDB
Leu-proHMDB
Leucine proline dipeptideHMDB
Leucine-proline dipeptideHMDB
Leucyl-prolineHMDB
LeucylprolineChEBI
Chemical FormulaC11H20N2O3
Average Molecular Weight228.292
Monoisotopic Molecular Weight228.147392512
IUPAC Name(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidine-2-carboxylic acid
Traditional Name(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidine-2-carboxylic acid
CAS Registry Number6403-35-6
SMILES
CC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(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)/t8-,9-/m0/s1
InChI KeyVTJUNIYRYIAIHF-IUCAKERBSA-N
Chemical Taxonomy
Description 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
  • Leucine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility44.6 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.16 m³·mol⁻¹ChemAxon
Polarizability24.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+159.3730932474
DeepCCS[M-H]-157.01230932474
DeepCCS[M-2H]-189.89930932474
DeepCCS[M+Na]+165.46330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LeucylprolineCC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O2737.1Standard polar33892256
LeucylprolineCC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O1875.1Standard non polar33892256
LeucylprolineCC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O1937.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Leucylproline,1TMS,isomer #1CC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C1898.7Semi standard non polar33892256
Leucylproline,1TMS,isomer #2CC(C)C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O1934.1Semi standard non polar33892256
Leucylproline,2TMS,isomer #1CC(C)C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C1916.0Semi standard non polar33892256
Leucylproline,2TMS,isomer #1CC(C)C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C2003.5Standard non polar33892256
Leucylproline,2TMS,isomer #1CC(C)C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C2455.3Standard polar33892256
Leucylproline,2TMS,isomer #2CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2054.0Semi standard non polar33892256
Leucylproline,2TMS,isomer #2CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2055.0Standard non polar33892256
Leucylproline,2TMS,isomer #2CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2641.0Standard polar33892256
Leucylproline,3TMS,isomer #1CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2096.9Semi standard non polar33892256
Leucylproline,3TMS,isomer #1CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2130.5Standard non polar33892256
Leucylproline,3TMS,isomer #1CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2290.9Standard polar33892256
Leucylproline,1TBDMS,isomer #1CC(C)C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C2128.3Semi standard non polar33892256
Leucylproline,1TBDMS,isomer #2CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O2168.6Semi standard non polar33892256
Leucylproline,2TBDMS,isomer #1CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C2400.0Semi standard non polar33892256
Leucylproline,2TBDMS,isomer #1CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C2388.7Standard non polar33892256
Leucylproline,2TBDMS,isomer #1CC(C)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C2627.7Standard polar33892256
Leucylproline,2TBDMS,isomer #2CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2509.6Semi standard non polar33892256
Leucylproline,2TBDMS,isomer #2CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2469.7Standard non polar33892256
Leucylproline,2TBDMS,isomer #2CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2726.2Standard polar33892256
Leucylproline,3TBDMS,isomer #1CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2751.8Semi standard non polar33892256
Leucylproline,3TBDMS,isomer #1CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2695.6Standard non polar33892256
Leucylproline,3TBDMS,isomer #1CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2606.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Leucylproline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 10V, Positive-QTOFsplash10-01t9-1290000000-a7d4bfdd98e774a63ec62019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 20V, Positive-QTOFsplash10-02ti-9320000000-11c16428d6d853c82e2d2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 40V, Positive-QTOFsplash10-066r-9000000000-1f0cc62f9745c1b92db32019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 10V, Negative-QTOFsplash10-0059-0690000000-abfdecce35ead141486f2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 20V, Negative-QTOFsplash10-01si-3930000000-da0f5e7072ac2161b71e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 40V, Negative-QTOFsplash10-03mj-9600000000-7be81d5eb7b4a169cabc2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 10V, Negative-QTOFsplash10-004i-0290000000-eeda503ca1f26574eff92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 20V, Negative-QTOFsplash10-03di-5920000000-79943170b00abeee82ab2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 40V, Negative-QTOFsplash10-03dj-9400000000-af008c1e3b04514148442021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 10V, Positive-QTOFsplash10-004i-1290000000-a2306aff6fd871be8a622021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 20V, Positive-QTOFsplash10-016s-9440000000-8aba88214d533f7870e02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucylproline 40V, Positive-QTOFsplash10-00di-9000000000-db271194855430c100f92021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal
details
UrineDetected and Quantified0.03 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027947
KNApSAcK IDNot Available
Chemspider ID72971
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound80817
PDB IDNot Available
ChEBI ID73580
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]