PIPERINE (CHEM007217)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:22:43 UTC
Update Date2016-11-09 01:09:53 UTC
Accession NumberCHEM007217
Identification
Common NamePIPERINE
ClassSmall Molecule
DescriptionA N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
BioperineHMDB
1-Piperoyl-(e,e)-piperidineHMDB
FEMA 2909HMDB
N-(e,e)-Piperoyl-piperidineHMDB
N-Ee-piperoyl-piperidineHMDB
PiperinHMDB
Piperine, (e,Z)-isomerMeSH, HMDB
Piperine, (Z,e)-isomerMeSH, HMDB
Piperine, (Z,Z)-isomerMeSH, HMDB
((1-5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidineMeSH, HMDB
(1-(5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidineMeSH, HMDB
Piperine, (e,e)-isomerMeSH, HMDB
Chemical FormulaC17H19NO3
Average Molecular Mass285.338 g/mol
Monoisotopic Mass285.136 g/mol
CAS Registry Number94-62-2
IUPAC Name(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Traditional Namebioperine
SMILESO=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1
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
Chemical Taxonomy
Description 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fe0-0590000000-49115b64f9d288ede20bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uki-1980000000-0d80d5bd56077694f4abSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fe0-0590000000-49115b64f9d288ede20bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uki-1980000000-0d80d5bd56077694f4abSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ru3-5490000000-47caa063ebe950468c83Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0910000000-28987f355a39728ed8e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-0090000000-6221df9a927cf5dae43fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0090000000-f586ee65972a8599fb3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-9f77f056ac9f2e385656Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0090000000-d91bf95f43f53499a538Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-1f5b570135a2c33d60cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-c67e35d994bd1857d3b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0190000000-38727bddc27cc1f12b21Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0032950000-09b8545ba31f6fbf5243Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01ti-0044970000-8efb835b518a1f9d631eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0033960000-0ebcac3b31c8914732a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0009700000-45fc15cfc95d4cb7619cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0009500000-356adf7cecbec3f587a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004r-0022950000-438f2d66c26e4fad4df9Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uxr-0930000000-08188c35582e879e867fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-8556d96344dd58005484Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0gbl-0910000000-0cc6374f3392d452f5faSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udr-0190000000-1fd31902ba916f49f5c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-000i-0090000000-d9688e24ce807650b12cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2290000000-12a3336a15ec4f2d04adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-6960000000-cfbbefb16249f62a712dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05q3-9300000000-e0c13b92ad036042aa06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-2e45c46d9e273a3e57f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6490000000-03ac1126cea4a744d034Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9200000000-b9bed611c188499924d5Spectrum
MSMass Spectrum (Electron Ionization)splash10-0v4r-4970000000-d7ea6f47f4b46495acb4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB12582
HMDB IDHMDB0029377
FooDB IDFDB000449
Phenol Explorer IDNot Available
KNApSAcK IDC00002065
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPiperine
Chemspider ID553590
ChEBI ID28821
PubChem Compound ID638024
Kegg Compound IDC03882
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10575373
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15531295
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18639606
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19110999
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24272201
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25645812
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=8347144
8. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.