ContaminantDB: Piperlongine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 21:33:53 UTC

Update Date

2016-11-09 01:17:51 UTC

Accession Number

CHEM024212

Identification

Common Name

Piperlongine

Class

Small Molecule

Description

Piplartine is found in herbs and spices. Piplartine is an alkaloid from the roots of Piper longum (long pepper

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Piperlongumine	Kegg
5,6-Dihydro-1-(3,4,5-trimethoxycinnamoyl)-2(1H)-pyridinone	HMDB
5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone, 9ci	HMDB
N-(3,4,5-Trimethoxycinnamoyl)-D3-piperidin-2-one	HMDB
Piperlonguminine	HMDB

Chemical Formula

C₁₇H₁₉NO₅

Average Molecular Mass

317.337 g/mol

Monoisotopic Mass

317.126 g/mol

CAS Registry Number

20069-09-4

IUPAC Name

1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one

Traditional Name

piperlongumine

SMILES

COC1=CC(\C=C\C(=O)N2CCC=CC2=O)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+

InChI Key

VABYUUZNAVQNPG-BQYQJAHWSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Hydropyridine
Benzenoid
Carboxylic acid imide, n-substituted
Carboxylic acid imide
Dicarboximide
Carboxylic acid derivative
Azacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cinnamamides (CHEBI:8241 )
Piperidine alkaloids (C10166 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	2.32	ALOGPS
logP	1.74	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	17.77	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.32 m³·mol⁻¹	ChemAxon
Polarizability	33.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-8696000000-1b169be7f9827d7d5bb9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-006x-2920000000-d1b540d4ec0c4f0488b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-006x-2920000000-d1b540d4ec0c4f0488b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00xr-0095000000-893ac7feee23d135f48f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0490000000-9bfa59dabc3856292b2d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00xr-0095000000-9ce911783fc7fee41f72	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0691000000-f25b002ae4f7d0b949c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-0094000000-893ac7feee23d135f48f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0490000000-1caef8816d72c8b3ed31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-01p2-1900000000-78c9457ea36bb5f39548	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0094000000-f13710ea1ae4605875e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-0920000000-3b5ae74c1ff52ea177e2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0490000000-b037dc0f31c179d7ffcf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-0095000000-90ecae44d143ba28ff4e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0691000000-3919a66965da314b796b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-0920000000-036fa5848d79b8e9cc7b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0f72-1900000000-2f07ed81f41453d1345b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0f72-1900000000-926af03c5b2bb1c4be9d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0006-0920000000-ee6613da7c274bef4f9a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0o6r-1900000000-159da23824e105e3f5bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-3129000000-e8f337c9dcd6328a666a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00r2-9766000000-04c2336d1dc5322a75b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gwf-9820000000-e13571d089d563c5dfc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0019000000-31c4ea7df9de2482d546	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-9278000000-870683a5557a7e8eac4e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9110000000-bac2f04584920167606f	Spectrum