Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:38:50 UTC
Update Date2022-03-07 02:53:53 UTC
HMDB IDHMDB0033874
Secondary Accession Numbers
  • HMDB33874
Metabolite Identification
Common NamePiperanine
DescriptionPiperanine 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. Piperanine has been detected, but not quantified in, herbs and spices and pepper (spice). This could make piperanine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Piperanine.
Structure
Data?1563862474
Synonyms
ValueSource
Delata-AlphaChEMBL, HMDB
Beta-DihydropiperineChEMBL, HMDB
DalphaChEMBL, HMDB
Delata-aGenerator, HMDB
Delata-αGenerator, HMDB
b-DihydropiperineGenerator, HMDB
β-dihydropiperineGenerator, HMDB
1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2-pentenyl]piperidineHMDB
5-(3,4-Methylenedioxyphenyl)-2-pentenoic acid piperidideHMDB
b-HydropiperylpiperidineHMDB
Da,b-dihydropiperineHMDB
Chemical FormulaC17H21NO3
Average Molecular Weight287.3535
Monoisotopic Molecular Weight287.152143543
IUPAC Name(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one
Traditional Name(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one
CAS Registry Number23512-46-1
SMILES
O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC1
InChI Identifier
InChI=1S/C17H21NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h3,7-9,12H,1-2,4-6,10-11,13H2/b7-3+
InChI KeyQHWOFMXDKFORMO-XVNBXDOJSA-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
  • N-acyl-piperidine
  • Piperidine
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point79 - 80 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.74 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP3.48ALOGPS
logP3.06ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)2.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity81.79 m³·mol⁻¹ChemAxon
Polarizability32.72 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.50131661259
DarkChem[M-H]-170.17131661259
DeepCCS[M+H]+165.50530932474
DeepCCS[M-H]-163.12330932474
DeepCCS[M-2H]-196.15930932474
DeepCCS[M+Na]+171.57430932474
AllCCS[M+H]+169.632859911
AllCCS[M+H-H2O]+166.132859911
AllCCS[M+NH4]+172.932859911
AllCCS[M+Na]+173.832859911
AllCCS[M-H]-174.032859911
AllCCS[M+Na-2H]-174.032859911
AllCCS[M+HCOO]-174.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PiperanineO=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC13667.3Standard polar33892256
PiperanineO=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC12343.6Standard non polar33892256
PiperanineO=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC12634.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Piperanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-3950000000-bcd7117a5db53c825b492017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piperanine 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 - Piperanine LC-ESI-qTof , Positive-QTOFsplash10-067i-0900000000-501111d1497bebd731752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piperanine , positive-QTOFsplash10-000i-0910000000-02c27ecc1fbd166614312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piperanine , positive-QTOFsplash10-000i-0910000000-6c87b10e6d03efc371202017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 10V, Positive-QTOFsplash10-000i-2290000000-50752c83b7a1b2c769312016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 20V, Positive-QTOFsplash10-000i-6960000000-4f522a781663933a605f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 40V, Positive-QTOFsplash10-052r-9300000000-a48b20e34a96fc77a1a82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 10V, Negative-QTOFsplash10-000i-0090000000-a6c24185982a09c089f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 20V, Negative-QTOFsplash10-001r-5490000000-b721e5b0b0d32bc8f89b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 40V, Negative-QTOFsplash10-001i-9310000000-8edaeb5f6a0de61f4f872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 10V, Positive-QTOFsplash10-000i-0090000000-3724bfaaf393a959b2f82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 20V, Positive-QTOFsplash10-000i-1490000000-b8e8c9fb7b120dedf3572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 40V, Positive-QTOFsplash10-01sr-4920000000-be8efcea844fe5793c152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 10V, Negative-QTOFsplash10-000i-0090000000-32affc6af32f5da1d2572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 20V, Negative-QTOFsplash10-000i-0290000000-28e9199aca5bd12b6b592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperanine 40V, Negative-QTOFsplash10-001i-2590000000-8e9636d54485b7ff81132021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012066
KNApSAcK IDNot Available
Chemspider ID4478657
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5320618
PDB IDNot Available
ChEBI ID167837
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1629081
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.. .