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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:04:50 UTC
Update Date2022-03-07 02:54:02 UTC
HMDB IDHMDB0034276
Secondary Accession Numbers
  • HMDB34276
Metabolite Identification
Common NameL,L-Cyclo(leucylprolyl)
DescriptionL,L-Cyclo(leucylprolyl), also known as cyclo(leu-pro) or cyclo(L-prolyl-L-leucyl), belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. L,L-Cyclo(leucylprolyl) 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 L,L-Cyclo(leucylprolyl).
Structure
Data?1563862538
Synonyms
ValueSource
Cyclo(L-leucyl-L-prolyl)ChEBI
Cyclo(L-pro-L-leu)ChEBI
Cyclo(L-prolyl-L-leucyl)ChEBI
Cyclo(leu-pro)ChEBI
Cyclo(pro-leu)ChEBI
Cyclo-L-leu-L-proChEBI
Gancidin WChEBI
L-Cyclo(leu-pro)ChEBI
L-Cyclo(leucyloprolyl)ChEBI
L-Leucyl-L-proline lactamChEBI
Cyclo(S-leucyl-S-prolyl)HMDB
Cyclo(leucyl-prolyl)HMDB
Cyclo(L-leu-L-pro)HMDB
Cyclo(proline-leucine)HMDB
Cyclo-L-prolyl-L-leucineHMDB
L-Leucyl-L-prolyl lactamHMDB
Maculosin 6HMDB
cis-Cyclo(L-leu-L-pro)HMDB
L,L-cyclo(Leucylprolyl)ChEBI
L,L-Cyclo(leucylprolyl)HMDB
Chemical FormulaC11H18N2O2
Average Molecular Weight210.277
Monoisotopic Molecular Weight210.136827828
IUPAC Name(3S,8aS)-1-hydroxy-3-(2-methylpropyl)-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one
Traditional Name(3S,8aS)-1-hydroxy-3-(2-methylpropyl)-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one
CAS Registry Number2873-36-1
SMILES
[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)NC2=O
InChI Identifier
InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)/t8-,9-/m0/s1
InChI KeySZJNCZMRZAUNQT-IUCAKERBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point168 - 172 °CNot 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
logP0.61ALOGPS
logP1.27ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.8ChemAxon
pKa (Strongest Basic)1.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.48 m³·mol⁻¹ChemAxon
Polarizability22.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-182.17830932474
DeepCCS[M+Na]+156.99130932474
AllCCS[M+H]+148.432859911
AllCCS[M+H-H2O]+144.632859911
AllCCS[M+NH4]+152.032859911
AllCCS[M+Na]+153.032859911
AllCCS[M-H]-151.132859911
AllCCS[M+Na-2H]-151.532859911
AllCCS[M+HCOO]-152.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L,L-Cyclo(leucylprolyl)[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)NC2=O2808.8Standard polar33892256
L,L-Cyclo(leucylprolyl)[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)NC2=O1618.6Standard non polar33892256
L,L-Cyclo(leucylprolyl)[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)NC2=O1958.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L,L-Cyclo(leucylprolyl),1TMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=O)N1[Si](C)(C)C1800.3Semi standard non polar33892256
L,L-Cyclo(leucylprolyl),1TMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=O)N1[Si](C)(C)C1850.9Standard non polar33892256
L,L-Cyclo(leucylprolyl),1TBDMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=O)N1[Si](C)(C)C(C)(C)C2021.1Semi standard non polar33892256
L,L-Cyclo(leucylprolyl),1TBDMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=O)N1[Si](C)(C)C(C)(C)C2120.4Standard non polar33892256
Spectra

GC-MS Spectra

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

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) , positive-QTOFsplash10-03k9-7970000000-995c2fe3f83730e940dc2019-05-16HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) , positive-QTOFsplash10-03k9-4950000000-327189e6a49090508fca2019-05-16HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) , positive-QTOFsplash10-0fwl-0920000000-e1dc27828630ca176f2c2019-05-16HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 35V, Positive-QTOFsplash10-00di-9410000000-0cf0537e03d60ce593542021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 10V, Positive-QTOFsplash10-03di-0090000000-eb9001f792e6e54198602019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 20V, Positive-QTOFsplash10-03di-3290000000-68aae20dc8ea6289a74a2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 40V, Positive-QTOFsplash10-0603-9000000000-f92521c806732fe0bf3e2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 10V, Negative-QTOFsplash10-0a4i-0190000000-04de6efd098f4d8b9c2b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 20V, Negative-QTOFsplash10-0aou-9210000000-d251726d15faaf1489272019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 40V, Negative-QTOFsplash10-1000-9100000000-213ecebbd718c39905c32019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 10V, Positive-QTOFsplash10-03di-0090000000-d21d6775448881318bd62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 20V, Positive-QTOFsplash10-03di-8390000000-83409e46a4b2e1d76db32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 40V, Positive-QTOFsplash10-00di-9000000000-d422c9c1874a732356612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 10V, Negative-QTOFsplash10-0a4i-0090000000-b31e4b4ae49103bba07c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 20V, Negative-QTOFsplash10-0a4i-0090000000-98eb3f95fa203c20ca6a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L,L-Cyclo(leucylprolyl) 40V, Negative-QTOFsplash10-0006-9100000000-7eafcc22317d1159e7342021-09-22Wishart 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 Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB093682
KNApSAcK IDC00018662
Chemspider ID5428292
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7074739
PDB IDNot Available
ChEBI ID133094
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .