Showing Compound Isopiperine (FDB000452)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:34 UTC

Update date

2019-11-26 02:54:49 UTC

Primary ID

FDB000452

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Isopiperine

Description

Isopiperine 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. Isopiperine is an extremely weak basic (essentially neutral) compound (based on its pKa). Isopiperine has been detected, but not quantified in, herbs and spices and pepper (spice). This could make isopiperine a potential biomarker for the consumption of these foods.

CAS Number

94-62-2

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
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-(e,e)-piperidine	HMDB
1-Piperoyl-piperidine	ChEBI
1-Piperoylpiperidine	ChEBI
Isopiperine	db_source

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	30.81 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

(2Z,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

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 71.56%; H 6.71%; N 4.91%; O 16.82%	DFC
Melting Point	Mp 89° (86°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2190000000-123438c71fcdece644dd	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-5940000000-dbaef921c2f0c6024fc9	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052u-9300000000-ba6d114da6339639b828	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-0b72a9d5834256ea6afa	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-6490000000-0d7d6d3228e177fa65d1	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9200000000-0275fa71d28b3007b121	2019-02-23	View Spectrum