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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:30:03 UTC
Update Date2019-01-11 19:37:54 UTC
HMDB IDHMDB0029377
Secondary Accession Numbers
  • HMDB29377
Metabolite Identification
Common NamePiperine
DescriptionConstit. of pepper (Piper nigrum) and many other Piper spp. (Piperaceae). Used to impart pungent taste to brandy. Responsible for the hot taste of pepper. Flavour ingredient.
Structure
Data?1547235474
Synonyms
ValueSource
(e,e)-1-PiperoylpiperidineChEBI
1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidineChEBI
1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidineChEBI
1-Piperoyl-piperidineChEBI
1-PiperoylpiperidineChEBI
N-[(e,e)-Piperoyl]piperidineChEBI
1-Piperoyl-(e,e)-piperidineHMDB
FEMA 2909HMDB
N-(e,e)-Piperoyl-piperidineHMDB
N-Ee-piperoyl-piperidineHMDB
PiperinHMDB
Piperine, (e,Z)-isomerMeSH
Piperine, (Z,e)-isomerMeSH
Piperine, (Z,Z)-isomerMeSH
((1-5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidineMeSH
(1-(5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidineMeSH
Piperine, (e,e)-isomerMeSH
BioperineCAS
Chemical FormulaC17H19NO3
Average Molecular Weight285.3377
Monoisotopic Molecular Weight285.136493479
IUPAC Name(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Traditional Namebioperine
CAS Registry Number94-62-2
SMILES
O=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Benzodioxole
  • N-acyl-piperidine
  • Alkaloid or derivatives
  • Styrene
  • Piperidine
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.04 mg/mL at 18 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP3.38ALOGPS
logP2.78ChemAxon
logS-3.3ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fe0-0590000000-49115b64f9d288ede20bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uki-1980000000-0d80d5bd56077694f4abView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fe0-0590000000-49115b64f9d288ede20bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uki-1980000000-0d80d5bd56077694f4abView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ru3-5490000000-47caa063ebe950468c83View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0910000000-28987f355a39728ed8e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-0090000000-6221df9a927cf5dae43fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0090000000-f586ee65972a8599fb3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-9f77f056ac9f2e385656View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0090000000-d91bf95f43f53499a538View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-1f5b570135a2c33d60cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-c67e35d994bd1857d3b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-38727bddc27cc1f12b21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0032950000-09b8545ba31f6fbf5243View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01ti-0044970000-8efb835b518a1f9d631eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0033960000-0ebcac3b31c8914732a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0009700000-45fc15cfc95d4cb7619cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0009500000-356adf7cecbec3f587a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0022950000-438f2d66c26e4fad4df9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uxr-0930000000-08188c35582e879e867fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2290000000-12a3336a15ec4f2d04adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-6960000000-cfbbefb16249f62a712dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05q3-9300000000-e0c13b92ad036042aa06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-2e45c46d9e273a3e57f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6490000000-03ac1126cea4a744d034View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9200000000-b9bed611c188499924d5View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0v4r-4970000000-d7ea6f47f4b46495acb4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000452
KNApSAcK IDC00002065
Chemspider ID553590
KEGG Compound IDC03882
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiperine
METLIN IDNot Available
PubChem Compound638024
PDB IDNot Available
ChEBI ID28821
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .