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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 of PELLITORINE

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

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 TargetPharmacologyConditionPotency
0.69 mM [IC50]
14.5 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

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.