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

Molecular Formula	C14H25NO
Molecular Weight	223.3544
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	2
Optical Activity	NONE

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

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:01:15 GMT 2023` Edited by `admin` on `Fri Dec 15 19:01:15 GMT 2023`
Record UNII	8IS5231171
Record Status	`Validated (UNII)`
Record Version

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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