Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2020-02-24 19:10:07 UTC
Primary IDFDB000449
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePiperine
DescriptionConstituent of pepper (Piper nigrum) and many other Piper subspecies (Piperaceae). It is used to impart pungent taste to brandy. Responsible for the hot taste of pepper. Flavour ingredient. Piperine is found in dill, herbs and spices, and pepper (spice).
CAS Number94-62-2
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
logP2.78ChemAxon
pKa (Strongest Basic)-0.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.9 m³·mol⁻¹ChemAxon
Polarizability32.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H19NO3
IUPAC name(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
InChI IdentifierInChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
InChI KeyMXXWOMGUGJBKIW-YPCIICBESA-N
Isomeric SMILESO=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1
Average Molecular Weight285.3377
Monoisotopic Molecular Weight285.136493479
Classification
ClassificationNot classified
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0v4r-4970000000-d7ea6f47f4b46495acb42015-03-01View Spectrum
GC-MSPiperine, non-derivatized, GC-MS Spectrumsplash10-0fe0-0590000000-49115b64f9d288ede20bSpectrum
GC-MSPiperine, non-derivatized, GC-MS Spectrumsplash10-0uki-1980000000-0d80d5bd56077694f4abSpectrum
GC-MSPiperine, non-derivatized, GC-MS Spectrumsplash10-0fe0-0590000000-49115b64f9d288ede20bSpectrum
GC-MSPiperine, non-derivatized, GC-MS Spectrumsplash10-0uki-1980000000-0d80d5bd56077694f4abSpectrum
Predicted GC-MSPiperine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ru3-5490000000-47caa063ebe950468c83Spectrum
Predicted GC-MSPiperine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0910000000-28987f355a39728ed8e42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-0090000000-6221df9a927cf5dae43f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0090000000-f586ee65972a8599fb3e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-9f77f056ac9f2e3856562017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0090000000-d91bf95f43f53499a5382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-1f5b570135a2c33d60cb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-c67e35d994bd1857d3b32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-38727bddc27cc1f12b212017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0032950000-09b8545ba31f6fbf52432017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01ti-0044970000-8efb835b518a1f9d631e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0033960000-0ebcac3b31c8914732a92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0009700000-45fc15cfc95d4cb7619c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0009500000-356adf7cecbec3f587a12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0022950000-438f2d66c26e4fad4df92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0uxr-0930000000-08188c35582e879e867f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-8556d96344dd580054842021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0gbl-0910000000-0cc6374f3392d452f5fa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udr-0190000000-1fd31902ba916f49f5c02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-000i-0090000000-d9688e24ce807650b12c2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2290000000-12a3336a15ec4f2d04ad2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-6960000000-cfbbefb16249f62a712d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05q3-9300000000-e0c13b92ad036042aa062016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-2e45c46d9e273a3e57f42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6490000000-03ac1126cea4a744d0342016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9200000000-b9bed611c188499924d52016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC03882
Pubchem Compound ID638024
Pubchem Substance IDNot Available
ChEBI ID28821
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBCK67-T:BCK69-V
EAFUS ID3054
Dr. Duke IDPIPERINE|TRANS-TRANS-PIPERINE
BIGG IDNot Available
KNApSAcK IDC00002065
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent ID638024
Wikipedia IDPiperine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
DillExpected but not quantifiedNot AvailableDUKE
PepperExpected but not quantifiedNot AvailablePHYTOHUB
Pepper (Spice)5350.000 - 5350.000 mg/100 g5350.000 mg/100 gDUKE, KNAPSACK
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Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.