Piperanine

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H21NO3
Molecular Weight	287.3535
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(\C=C\CCC1=CC=C2OCOC2=C1)N3CCCCC3

InChI

InChIKey=QHWOFMXDKFORMO-XVNBXDOJSA-N

InChI=1S/C17H21NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h3,7-9,12H,1-2,4-6,10-11,13H2/b7-3+

HIDE SMILES / InChI

Molecular Formula	C17H21NO3
Molecular Weight	287.3535
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20460725	Agonist 2752		6.0 µM [EC50]
Transient receptor potential cation channel subfamily A member 1 38 Target ID: CHEMBL6007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20460725	Agonist 2752		148.3 µM [EC50]

PubMed

Title	Date	PubMed
Direct from solid natural products to pure compounds in a single step: Coupling online extraction with high-speed counter-current chromatography.	2018-09	30073789
The Possibility of Using Isolated Alkaloid Compounds and Crude Extracts of Piper retrofractum (Piperaceae) as Larvicidal Control Agents for Culex quinquefasciatus (Diptera: Culicidae) Larvae.	2018-08-29	29796657
[Identify metabolites of Piper longum alkaloids in feces and urine of rat by HPLC-FT-MS].	2018-05	29902888
Identification and simultaneous quantification of five alkaloids in Piper longum L. by HPLC-ESI-MS(n) and UFLC-ESI-MS/MS and their application to Piper nigrum L.	2015-06-15	25660876
Activation of TRPV1 and TRPA1 by black pepper components.	2010	20460725
Analysis by HPLC and LC/MS of pungent piperamides in commercial black, white, green, and red whole and ground peppercorns.	2008-05-14	18386929
Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.	2008-03-15	18289853
In vivo and in vitro activities of the seed extract of Piper guineense Schum. and Thonn. against skin and gill monogenean parasites of gold fish (Carassius auratus auratus).	2004-10	15551399
Preparative isolation and purification of amides from the fruits of Piper longum L. by upright counter-current chromatography and reversed-phase liquid chromatography.	2004-06-25	15230526
New amides and gastroprotective constituents from the fruit of Piper chaba.	2004-02	14994194
Constituents of Chinese Piper species and their inhibitory activity on prostaglandin and leukotriene biosynthesis in vitro.	2001-05	11297843

Substance Class	Chemical Created by `admin` on `Tue Apr 01 16:49:58 GMT 2025` Edited by `admin` on `Tue Apr 01 16:49:58 GMT 2025`
Record UNII	GZC2LZ46CZ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Piperanine

Common Name

English

NSC-125180

Preferred Name

English

(2E)-5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2-penten-1-one

Systematic Name

English

2-Penten-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-

Systematic Name

English

Piperidine, 1-[5-[3,4-(methylenedioxy)phenyl]-2-pentenoyl]-, (E)-

Systematic Name

English

4,5-Dihydroxypiperine

Common Name

English

2-Penten-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E)-

Systematic Name

English

(E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpent-2-en-1-one

Systematic Name

English

Piperidine, 1-[(2E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2-pentenyl]-

Systematic Name

English

5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2-penten-1-one

Systematic Name

English

Piperanin

Common Name

English

Code System Code Type Description

CAS

65937-41-9