ChemFOnt: Showing chemical card for Piperine (CFc000010621)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:58:07 UTC

Chemfont ID

CFc000010621

Molecule Identification

Common Name

Piperine

Definition

Piperine, also known as fema 2909, 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 a pepper tasting compound. Piperine is found in the highest concentration within pepper (Piper nigrum) and many other Piper species. Piperine has also been detected, but not quantified, in dills and herbs and spices. Piperine is responsible for the hot taste of pepper. Piperine has been used in trials studying the treatment of Multiple Myeloma and Deglutition Disorders. It is used to impart pungent taste to brandy.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e,e)-1-Piperoylpiperidine	ChEBI
1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine	ChEBI
1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine	ChEBI
1-Piperoyl-piperidine	ChEBI
1-Piperoylpiperidine	ChEBI
N-[(e,e)-Piperoyl]piperidine	ChEBI
Bioperine	HMDB
1-Piperoyl-(e,e)-piperidine	HMDB
FEMA 2909	HMDB
N-(e,e)-Piperoyl-piperidine	HMDB
N-Ee-piperoyl-piperidine	HMDB
Piperin	HMDB
Piperine, (e,Z)-isomer	MeSH, HMDB
Piperine, (Z,e)-isomer	MeSH, HMDB
Piperine, (Z,Z)-isomer	MeSH, HMDB
((1-5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine	MeSH, HMDB
(1-(5-(1,3)-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine	MeSH, HMDB
Piperine, (e,e)-isomer	MeSH, HMDB

Chemical Formula

C₁₇H₁₉NO₃

Average Molecular Weight

285.3377

Monoisotopic Molecular 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=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 Key

MXXWOMGUGJBKIW-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.

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 )

Functional Ontology

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 27355821)

Cellular substructure

Membrane (HMDB: HMDB0029377)
Cell membrane (HMDB: HMDB0029377)

Organ

Placenta (HMDB: HMDB0029377)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029377)

Source

Exogenous

Exogenous (HMDB: HMDB0029377)

Food

Food (HMDB: HMDB0029377)

Herb and spice

Herb

Dill (FooDB: FOOD00013)

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)

Endogenous

Endogenous (HMDB: HMDB0029377)

Plant

Plant (HMDB: HMDB0029377)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0029377)
Hepatoprotective (HMDB: HMDB0029377)

Antineoplastic agent

Cancer preventive (HMDB: HMDB0029377)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Analgesic (HMDB: HMDB0029377)

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0029377)
Antioxidant (HMDB: HMDB0029377)

Abortifacient (HMDB: HMDB0029377)
Antipyretic (HMDB: HMDB0029377)
Central nervous system stimulant (HMDB: HMDB0029377)
Hepatoprotective agent (HMDB: HMDB0029377)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0029377)

Agriculture

Pesticide

Insecticide (HMDB: HMDB0029377)
Parasiticide (HMDB: HMDB0029377)

Pesticide (HMDB: HMDB0029377)

Biological role

Adrenergic agent (HMDB: HMDB0029377)
Analeptic (HMDB: HMDB0029377)
Anesthetic (HMDB: HMDB0029377)
Anti aflatoxin (HMDB: HMDB0029377)
Anti bacterial (HMDB: HMDB0029377)
Anti clastogen (HMDB: HMDB0029377)
Anti convulsant (HMDB: HMDB0029377)
Anti edemic (HMDB: HMDB0029377)
Anti fertility (HMDB: HMDB0029377)
Anti implantation (HMDB: HMDB0029377)
Anti-inflammatory (HMDB: HMDB0029377)
Anti leishmanic (HMDB: HMDB0029377)
Anti mutagenic (HMDB: HMDB0029377)
Anti narcotic (HMDB: HMDB0029377)
Anti nociceptive (HMDB: HMDB0029377)
Anti plasmodial (HMDB: HMDB0029377)
Anti septic (HMDB: HMDB0029377)
Anti spasmodic (HMDB: HMDB0029377)
Anti substance-P (HMDB: HMDB0029377)
ATPase stimulant (HMDB: HMDB0029377)
Carcinogenic (HMDB: HMDB0029377)
Cardiotonic (HMDB: HMDB0029377)
Carminative (HMDB: HMDB0029377)
Catecholaminogenic (HMDB: HMDB0029377)
Cytochrome-p450 inducer (HMDB: HMDB0029377)
Diaphoretic (HMDB: HMDB0029377)
Endorphinogenic (HMDB: HMDB0029377)
Epinephrininergic (HMDB: HMDB0029377)
Hypertensive (HMDB: HMDB0029377)
Hypotensive (HMDB: HMDB0029377)
Insectifuge (HMDB: HMDB0029377)
Mutagenic (HMDB: HMDB0029377)
Myocontractant (HMDB: HMDB0029377)
Myorelaxant (HMDB: HMDB0029377)
Peristaltic (HMDB: HMDB0029377)
Respirostimulant (HMDB: HMDB0029377)
Secretogogue (HMDB: HMDB0029377)
Serotoninergic (HMDB: HMDB0029377)
Spermigenic (HMDB: HMDB0029377)
Stimulant (HMDB: HMDB0029377)
Thermogenic (HMDB: HMDB0029377)
Thyrostimulant (HMDB: HMDB0029377)

Modulator

Inhibitor

Enzyme inhibitor

Aryl-hydrocarbon-hydroxylase inhibitor (HMDB: HMDB0029377)
Antiglucuronidase (HMDB: HMDB0029377)

Cytochrome-P450 inhibitor (HMDB: HMDB0029377)

Physical Properties

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