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Details

Stereochemistry ACHIRAL
Molecular Formula C17H19NO3
Molecular Weight 285.3377
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of ISOCHAVICINE

SMILES

O=C(\C=C\C=C/C1=CC2=C(OCO2)C=C1)N3CCCCC3

InChI

InChIKey=MXXWOMGUGJBKIW-MFDSWNTHSA-N
InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2-,7-3+

HIDE SMILES / InChI
Molecular Formula C17H19NO3
Molecular Weight 285.3377
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23625885

Piperine is a simple and pungent alkaloid found in the seeds of black pepper (Piper nigrum). Following its isolation and full characterization, the biological properties of piperine have been extensively studied, and piperine-like derivatives have shown an interesting range of pharmacological activities. Piperine is currently paving its way to become a privileged scaffold for the development of bioactive compounds with therapeutic application in multiple human diseases. In particular, piperine derivatives were shown to modulate the activity of several targets related to neurological disorders, including epilepsy, Parkinson's disease, depression and pain related disorders. Moreover, the efflux pump inhibitory ability of piperine and its analogues tackles important drug resistance mechanisms and may improve the clinical efficacy of antibiotic and anticancer drugs. Piperine has been found to have immunomodulatory, anti-oxidant, anti-asthmatic, anti-carcinogenic, anti-inflammatory, anti-ulcer, and anti-amoebic properties.

CNS Activity

CNS Penetrant
2554
Curator's Comment: Blood-brain barrier penetrant and CNS active

Originator

Ørsted, H.C.
3
Curator's Comment: Piperine was discovered in 1819, when Hans Christian Ørsted isolated it from the fruits of the source plant of black and white pepper, piper nigrum. Piperine's chemical constitution was established by laboritory synthesis in 1882 and 1894.

Approval Year

2011
587
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 14.19 µM [IC50]
Inhibitor
8297
 2.12 µM [IC50]
Inhibitor
8297
Inhibitor
8297
 133.3 µM [IC50]
Inhibitor
8297
 45.0 µM [IC50]
Inhibitor
8297
 230.7 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Palliative
Phase I
428
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Action of intrathecal capsaicin and its structural analogues on the content and release of spinal substance P: selectivity of action and relationship to analgesia.
1984 Jul 23
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
Role of cytochrome P450 2B1 in puromycin aminonucleoside-induced cytotoxicity to glomerular epithelial cells.
2003
Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.
2003 Dec
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.
2004 Apr
Piperine is a potent inhibitor of nuclear factor-kappaB (NF-kappaB), c-Fos, CREB, ATF-2 and proinflammatory cytokine gene expression in B16F-10 melanoma cells.
2004 Dec 20
Effects of xenobiotics and peroxisome proliferator-activated receptor-alpha on the human UDPglucose dehydrogenase gene expression.
2005
Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1).
2005 Mar
Modulation of cadmium induced alterations in murine thymocytes by piperine: oxidative stress, apoptosis, phenotyping and blastogenesis.
2006 Aug 14
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Identification of kaempferol as an inhibitor of cigarette smoke-induced activation of the aryl hydrocarbon receptor and cell transformation.
2007 Mar
Antioxidant effects of a Rhodobryum roseum extract and its active components in isoproterenol-induced myocardial injury in rats and cardiac myocytes against oxidative stress-triggered damage.
2009 Jan
Piperine as an inhibitor of Rv1258c, a putative multidrug efflux pump of Mycobacterium tuberculosis.
2010 Aug
Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening.
2011
The plant alkaloid piperine as a potential inhibitor of ethidium bromide efflux in Mycobacterium smegmatis.
2011 Feb
Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by piperine via the inhibition of PKCα/ERK1/2-dependent matrix metalloproteinase-9 expression.
2011 May 30
Piperine inhibits PMA-induced cyclooxygenase-2 expression through downregulating NF-κB, C/EBP and AP-1 signaling pathways in murine macrophages.
2012 Jul
Anti-HBV active constituents from Piper longum.
2013 Apr 1
Piperine potentiates the antidepressant-like effect of trans-resveratrol: involvement of monoaminergic system.
2013 Dec
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.
2013 Oct
Piperine activates human pregnane X receptor to induce the expression of cytochrome P450 3A4 and multidrug resistance protein 1.
2013 Oct 1
Mitigating efficacy of piperine in the physiological derangements of high fat diet induced obesity in Sprague Dawley rats.
2014 Sep 25
Piperine blocks interleukin-2-driven cell cycle progression in CTLL-2 T lymphocytes by inhibiting multiple signal transduction pathways.
2015 Apr 2
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Patents

Patents

JP2005112846A
3
JP2011105715A
3
JPH08173083A
4

Sample Use Guides

In Vivo Use Guide
A single dose of Piperine 20 mg was administered daily for 10 days
Route of Administration: Oral
In Vitro Use Guide
Piperine inhibited the proliferation of SW480 and HT-29 cells in a dose-dependent manner, it had low cytotoxicity on these cell lines with 50 % inhibiting concentration (IC50) values greater than 100 uM. Pretreatment of the cells with 40 uM piperine for 1 h significantly inhibited the mRNA production of CXCL8 in response to LPS stimulation in SW480 and HT-29 cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 00:11:33 GMT 2023
Edited
by admin
on Sat Dec 16 00:11:33 GMT 2023
Record UNII
QTK8MIO5Z7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOCHAVICINE
Common Name English
PIPERIDINE, 1-(5-(1,3-BENZODIOXOL-5-YL)-1-OXO-2,4-PENTADIENYL)-, (E,Z)-
Common Name English
PIPERIDINE, 1-((2E,4Z)-5-(1,3-BENZODIOXOL-5-YL)-1-OXO-2,4-PENTADIENYL)-
Systematic Name English
2,4-PENTADIEN-1-ONE, 5-(1,3-BENZODIOXOL-5-YL)-1-(1-PIPERIDINYL)-, (2E,4Z)-
Systematic Name English
Code System Code Type Description
FDA UNII
QTK8MIO5Z7
Created by admin on Sat Dec 16 00:11:33 GMT 2023 , Edited by admin on Sat Dec 16 00:11:33 GMT 2023
PRIMARY
CAS
30511-77-4
Created by admin on Sat Dec 16 00:11:33 GMT 2023 , Edited by admin on Sat Dec 16 00:11:33 GMT 2023
PRIMARY
PUBCHEM
1548914
Created by admin on Sat Dec 16 00:11:33 GMT 2023 , Edited by admin on Sat Dec 16 00:11:33 GMT 2023
PRIMARY
NIH
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