PELLITORINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H25NO
Molecular Weight	223.3544
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC\C=C\C=C\C(=O)NCC(C)C

InChI

InChIKey=MAGQQZHFHJDIRE-BNFZFUHLSA-N

InChI=1S/C14H25NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h8-11,13H,4-7,12H2,1-3H3,(H,15,16)/b9-8+,11-10+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28899508 | https://www.ncbi.nlm.nih.gov/pubmed/28185326 | https://www.ncbi.nlm.nih.gov/pubmed/27493960 | https://www.ncbi.nlm.nih.gov/pubmed/20428051 | https://www.ncbi.nlm.nih.gov/pubmed/23973654

Pellitorine is a major amide alkaloid, isolated from Piper longum, Zanthoxylum piperitum or heitzii, Anacyclus pyrethrum, Piper nigrum. Pellitorine can serve as an antagonist of the TRPV1 and may inhibit exovanilloid-induced pain. It exhibits anti-inflammatory activity via activating the Nrf2/HO-1 pathway. Pellitorine shows a good gut permeation and rapidly permeates the BBB once in the blood, indicating a possible role in the treatment of central nervous system diseases. Pellitorine, which was isolated from the roots of Piper nigrum, showed strong cytotoxic activities against HL60 and MCT-7 cancer cell lines. The drug possesses antithrombotic activities and offers bases for development of a novel anticoagulant.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Vanilloid receptor 53 Target ID: CHEMBL5102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28899508	Antagonist 2778	0.69 mM [IC50]
nitric oxide production involved in inflammatory response 17 Target ID: GO:0002537 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28185326	Inhibitor 8297	14.5 µM [IC50]
Acetyl-coenzyme A synthetase (Human) 1 Target ID: Acetyl-coenzyme A synthetase (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25422952	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28899508	Primary	Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20428051	Primary	Basic research	Unknown Approved Use Unknown
Severe vascular inflammatory diseases 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24077682	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides.	2003 Apr	12709897

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 4.5 or 9 ug per animal

Route of Administration: Intravenous

In Vitro Use Guide

Trans-pellitorine was found to suppress mean lipid accumulation in 3T3-L1 cells, when applied during differentiation and maturation, but also during maturation phase solely of 3T3-L1 cells in a concentration range between 1 nM and 1 uM by up to 8.84 or 7.49, respectively.

Name

Type

Language

PELLITORINE

Common Name

English

(E,E)-N-ISOBUTYL-2,4-DECADIENAMIDE

Systematic Name

English

METHYLPROPYL)-2,4-DECADIENAMIDE, (E,E)-N-(2-

Common Name

English

N-ISOBUTYL-2,4-DECADIENAMIDE, TRANS,TRANS-

Systematic Name

English

FEMA NO. 4148

Code

English

(2E,4E)-N-(2-METHYLPROPYL)-2,4-DECADIENAMIDE

Systematic Name

English

N-ISOBUTYL (E,E)-2,4-DECADIENAMIDE

Systematic Name

English

PELLITORINE [MI]

Common Name

English

Code System Code Type Description

JECFA MONOGRAPH

1587