AFCDB: Piperine (FDB000449)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:34 UTC

Update date

2020-02-24 19:10:07 UTC

Primary ID

FDB000449

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Piperine

Description

Piperine 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. Piperine is an animal and pepper tasting compound. Piperine is found, on average, in the highest concentration within pepper (spice). Piperine has also been detected, but not quantified in, a few different foods, such as dills (Anethum graveolens), herbs and spices, and peppers (Capsicum annuum). This could make piperine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Piperine.

CAS Number

94-62-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
logP	2.78	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.9 m³·mol⁻¹	ChemAxon
Polarizability	32.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H19NO3

IUPAC name

(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

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

Isomeric SMILES

O=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1

Average Molecular Weight

285.3377

Monoisotopic Molecular Weight

285.136493479

Classification

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-acylpiperidine (CHEBI:28821 )
benzodioxoles (CHEBI:28821 )
piperidine alkaloid (CHEBI:28821 )
carboxamide (CHEBI:28821 )
Piperidine alkaloids (C03882 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	pKa 1.98 (15°)	DFC
Experimental Water Solubility	0.04 mg/mL at 18 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Isoelectric point	Not Available
Mass Composition	C 71.56%; H 6.71%; N 4.91%; O 16.82%	DFC
Melting Point	Mp 129°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0v4r-4970000000-d7ea6f47f4b46495acb4	2015-03-01	View Spectrum
GC-MS	Piperine, non-derivatized, GC-MS Spectrum	splash10-0fe0-0590000000-49115b64f9d288ede20b	Spectrum
GC-MS	Piperine, non-derivatized, GC-MS Spectrum	splash10-0uki-1980000000-0d80d5bd56077694f4ab	Spectrum
GC-MS	Piperine, non-derivatized, GC-MS Spectrum	splash10-0fe0-0590000000-49115b64f9d288ede20b	Spectrum
GC-MS	Piperine, non-derivatized, GC-MS Spectrum	splash10-0uki-1980000000-0d80d5bd56077694f4ab	Spectrum
Predicted GC-MS	Piperine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ru3-5490000000-47caa063ebe950468c83	Spectrum
Predicted GC-MS	Piperine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-0910000000-28987f355a39728ed8e4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0udi-0090000000-6221df9a927cf5dae43f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0090000000-f586ee65972a8599fb3e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0190000000-9f77f056ac9f2e385656	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0090000000-d91bf95f43f53499a538	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0190000000-1f5b570135a2c33d60cb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0190000000-c67e35d994bd1857d3b3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0190000000-38727bddc27cc1f12b21	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-004r-0032950000-09b8545ba31f6fbf5243	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-01ti-0044970000-8efb835b518a1f9d631e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-004r-0033960000-0ebcac3b31c8914732a9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-0009700000-45fc15cfc95d4cb7619c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-0009500000-356adf7cecbec3f587a1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-004r-0022950000-438f2d66c26e4fad4df9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0uxr-0930000000-08188c35582e879e867f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1900000000-8556d96344dd58005484	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0gbl-0910000000-0cc6374f3392d452f5fa	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udr-0190000000-1fd31902ba916f49f5c0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-000i-0090000000-d9688e24ce807650b12c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2290000000-12a3336a15ec4f2d04ad	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-6960000000-cfbbefb16249f62a712d	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05q3-9300000000-e0c13b92ad036042aa06	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0190000000-2e45c46d9e273a3e57f4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-6490000000-03ac1126cea4a744d034	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9200000000-b9bed611c188499924d5	2016-08-03	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C03882

Pubchem Compound ID

638024

Pubchem Substance ID

Not Available

ChEBI ID

28821

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BCK67-T:BCK69-V

EAFUS ID

3054

Dr. Duke ID

PIPERINE|TRANS-TRANS-PIPERINE

BIGG ID

Not Available

KNApSAcK ID

C00002065

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

638024

Wikipedia ID

Piperine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Dill	Expected but not quantified	Not Available	DUKE

Showing 1 to 1 of 1 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
adrenergic	37962	Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.	DUKE
analeptic	35337	Any drug that enhances the activity of the central nervous system.	DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anesthetic			DUKE
anti aflatoxin	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti clastogen			DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti edemic			DUKE

Showing 1 to 10 of 57 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
animal	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
pepper	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695

Showing 1 to 2 of 2 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not 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.

Piperine (FDB000449)

Structure for FDB000449 (Piperine)