L-Leucyl-L-proline (CHEM040001)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 19:26:48 UTC
Update Date2016-11-09 01:22:10 UTC
Accession NumberCHEM040001
Identification
Common NameL-Leucyl-L-proline
ClassSmall Molecule
DescriptionA dipeptide formed from L-leucine and L-proline residues.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass228.288 g/mol
Monoisotopic Mass228.147 g/mol
CAS Registry NumberNot Available
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
SMILESCC(C)CC(N)C(=O)N1CCCC1C(O)=O
InChI IdentifierInChI=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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-1290000000-a7d4bfdd98e774a63ec6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ti-9320000000-11c16428d6d853c82e2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9000000000-1f0cc62f9745c1b92db3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0690000000-abfdecce35ead141486fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-3930000000-da0f5e7072ac2161b71eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03mj-9600000000-7be81d5eb7b4a169cabcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0290000000-eeda503ca1f26574eff9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-5920000000-79943170b00abeee82abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-9400000000-af008c1e3b0451414844Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1290000000-a2306aff6fd871be8a62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016s-9440000000-8aba88214d533f7870e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-db271194855430c100f9Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0011175
FooDB IDFDB027947
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID72971
ChEBI ID73580
PubChem Compound ID80817
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.