| Common Name |
Piperine
| Description |
Isopiperine is found in herbs and spices. Isopiperine is a constituent of pepper (Piper nigrum) (Piperaceae).Piperine belongs to the family of 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, slifur and more rarely other elements such as chlorine, bromine, and phosphorus[1]. (Reference: [1]Alkaloid: http://en.wikipedia.org/wiki/Alkaloid).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB29377 (Piperine)
| Synonyms |
| Value |
Source |
(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
| Chemical Formlia |
C17H19NO3
| Average Molecliar Weight |
285.3377
| Monoisotopic Molecliar Weight |
285.136493479
| IUPAC Name |
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
| Traditional Name |
bioperine
| CAS Registry Number |
94-62-2
| SMILES |
O=C(C=CC=CC1=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 Key |
MXXWOMGUGJBKIW-YPCIICBESA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities 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, slifur and more rarely other elements such as chlorine, bromine, and phosphorus.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Alkaloids and derivatives
| Sub Class |
Not Available
| Direct Parent |
Alkaloids and derivatives
| Alternative Parents |
N-acylpiperidines
Benzodioxoles
Styrenes
Tertiary carboxylic acid amides
Oxacyclic compounds
Azacyclic compounds
Acetals
Organopnictogen compounds
Organonitrogen compounds
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
N-acylpiperidine (CHEBI:28821 )
benzodioxoles (CHEBI:28821 )
piperidine alkaloid (CHEBI:28821 )
carboxamide (CHEBI:28821 )
Piperidine alkaloids (C03882 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Nutrient
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.04 mg/mL at 18 °CNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.15 mg/mLALOGPS
logP3.38ALOGPS
logP2.78ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)2.37ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.9 m3·mol-1ChemAxon
Polarizability32.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0udi-0090000000-6221df9a927cf5dae43fView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0udi-0090000000-f586ee65972a8599fb3eView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0udi-0190000000-9f77f056ac9f2e385656View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0udi-0090000000-d91bf95f43f53499a538View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0udi-0190000000-1f5b570135a2c33d60cbView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0udi-0190000000-c67e35d994bd1857d3b3View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0udi-0190000000-38727bddc27cc1f12b21View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-004r-0032950000-09b8545ba31f6fbf5243View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-01ti-0044970000-8efb835b518a1f9d631eView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-004r-0033960000-0ebcac3b31c8914732a9View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0a4i-0009700000-45fc15cfc95d4cb7619cView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0a4i-0009500000-356adf7cecbec3f587a1View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-004r-0022950000-438f2d66c26e4fad4df9View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| MS |
Mass Spectrum (Electron Ionization)splash10-0v4r-4970000000-d7ea6f47f4b46495acb4View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000452
| KNApSAcK ID |
Not Available
| Chemspider ID |
553590
| KEGG Compound ID |
C03882
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Piperine
| NuGOwiki Link |
HMDB29377
| Metagene Link |
HMDB29377
| METLIN ID |
Not Available
| PubChem Compound |
638024
| PDB ID |
Not Available
| ChEBI ID |
28821
Product: DprE1-IN-2
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 12112397
