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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:35:21 UTC
Update Date2022-09-22 18:35:09 UTC
HMDB IDHMDB0030187
Secondary Accession Numbers
  • HMDB30187
Metabolite Identification
Common Name(E,E)-Piperlonguminine
Description(E,E)-Piperlonguminine, also known as piperlongumine, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms (E,E)-Piperlonguminine has been detected, but not quantified in, herbs and spices. This could make (e,e)-piperlonguminine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E,E)-Piperlonguminine.
Structure
Data?1563861950
Synonyms
ValueSource
(2E,4E)-5-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidateHMDB
PiperlonguminineHMDB
PiperlongumineHMDB
Chemical FormulaC16H19NO3
Average Molecular Weight273.327
Monoisotopic Molecular Weight273.136493479
IUPAC Name(Z,2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidic acid
Traditional Name(Z,2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienimidic acid
CAS Registry Number5950-12-9
SMILES
CC(C)C\N=C(/O)\C=C\C=C\C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)/b5-3+,6-4+
InChI KeyWHAAPCGHVWVUEX-GGWOSOGESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Styrene
  • N-acyl-amine
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point167 - 169 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility17.36 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.006 g/LALOGPS
logP3.58ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)7.72ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.13 m³·mol⁻¹ChemAxon
Polarizability31.45 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+H]+171.23630932474
DeepCCS[M-H]-168.87830932474
DeepCCS[M-2H]-201.76430932474
DeepCCS[M+Na]+177.3330932474
AllCCS[M+H]+164.232859911
AllCCS[M+H-H2O]+160.732859911
AllCCS[M+NH4]+167.532859911
AllCCS[M+Na]+168.432859911
AllCCS[M-H]-169.732859911
AllCCS[M+Na-2H]-169.732859911
AllCCS[M+HCOO]-169.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(E,E)-PiperlonguminineCC(C)C\N=C(/O)\C=C\C=C\C1=CC2=C(OCO2)C=C13787.8Standard polar33892256
(E,E)-PiperlonguminineCC(C)C\N=C(/O)\C=C\C=C\C1=CC2=C(OCO2)C=C12247.1Standard non polar33892256
(E,E)-PiperlonguminineCC(C)C\N=C(/O)\C=C\C=C\C1=CC2=C(OCO2)C=C12513.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(E,E)-Piperlonguminine,1TMS,isomer #1CC(C)C/N=C(/C=C/C=C/C1=CC=C2OCOC2=C1)O[Si](C)(C)C2451.2Semi standard non polar33892256
(E,E)-Piperlonguminine,1TBDMS,isomer #1CC(C)C/N=C(/C=C/C=C/C1=CC=C2OCOC2=C1)O[Si](C)(C)C(C)(C)C2661.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (E,E)-Piperlonguminine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-4290000000-427cd8f96702f4d87b602017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E,E)-Piperlonguminine GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9375000000-df52f1f3e0600e0192c62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E,E)-Piperlonguminine 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 - (E,E)-Piperlonguminine LC-ESI-qTof , Positive-QTOFsplash10-0udi-0690000000-aa4a8e7d85b84fc68ba62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (E,E)-Piperlonguminine , positive-QTOFsplash10-00kr-0910000000-2e88b4e4a73fd8b3c4ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (E,E)-Piperlonguminine 0V, Positive-QTOFsplash10-00di-0090000000-2c5137df36f0ce8b47f62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (E,E)-Piperlonguminine 30V, Positive-QTOFsplash10-0a4r-4910000000-d0a82a1892f058f45b672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (E,E)-Piperlonguminine 0V, Positive-QTOFsplash10-00di-0090000000-5c4aa81e45c8f50e65342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Positive-QTOFsplash10-00di-0190000000-684772db3f325d77e9b42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (E,E)-Piperlonguminine 30V, Positive-QTOFsplash10-052r-5910000000-3670d53479869ebd58d12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Positive-QTOFsplash10-00di-0290000000-ce08f32a865fc569c4f32021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Positive-QTOFsplash10-00di-9140000000-e2b9ff384b615e68e4842016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 20V, Positive-QTOFsplash10-00di-9000000000-ce265384b494297a72332016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 40V, Positive-QTOFsplash10-0a4i-9000000000-a7a86f1ff4ed9259c1c72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Negative-QTOFsplash10-00di-0090000000-25db048f484dbe4caff52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 20V, Negative-QTOFsplash10-00di-4690000000-73a43e1e711ef3fcecfd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 40V, Negative-QTOFsplash10-00dm-7910000000-0a3050421629ca7cf18f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Positive-QTOFsplash10-00di-0090000000-4aad5806e19a0e184d442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 20V, Positive-QTOFsplash10-0h90-2790000000-99eac5e0140f785c87182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 40V, Positive-QTOFsplash10-00di-3910000000-609e969720c31ae23e442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 10V, Negative-QTOFsplash10-00di-0090000000-9a5ec9d1a8133eb075752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 20V, Negative-QTOFsplash10-00di-0290000000-45b698369ecf633548f92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E,E)-Piperlonguminine 40V, Negative-QTOFsplash10-006t-2910000000-0c3f1dbd52589070c55e2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002005
KNApSAcK IDC00042857
Chemspider ID4478660
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5320621
PDB IDNot Available
ChEBI ID520668
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1771521
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.. .