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
SMILES
O=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N3CCCCC3
InChI
InChIKey=MXXWOMGUGJBKIW-YPCIICBESA-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+
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26560940 | https://www.ncbi.nlm.nih.gov/pubmed/26146123Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23625885
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26560940 | https://www.ncbi.nlm.nih.gov/pubmed/26146123
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27018328
Curator's Comment: Blood-brain barrier penetrant and CNS active
Originator
Sources: http://learnpiperine.weebly.com/history.html
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27821437 |
14.19 µM [IC50] | ||
Target ID: CHEMBL340 |
2.12 µM [IC50] | ||
Target ID: map04010 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25471891 |
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Target ID: CHEMBL2321614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24302912 |
133.3 µM [IC50] | ||
Target ID: CHEMBL2321613 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24302912 |
45.0 µM [IC50] | ||
Target ID: CHEMBL2331042 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24302912 |
230.7 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
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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 |
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Effects of xenobiotics and peroxisome proliferator-activated receptor-alpha on the human UDPglucose dehydrogenase gene expression. | 2005 |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27670974
A single dose of Piperine 20 mg was administered daily for 10 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25471891
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
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Record UNII |
U71XL721QK
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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DSLD |
2372 (Number of products:123)
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NCI_THESAURUS |
C257
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JECFA EVALUATION |
PIPERINE
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EPA PESTICIDE CODE |
43501
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CFR |
21 CFR 172.515
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Code System | Code | Type | Description | ||
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638024
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C72629
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U71XL721QK
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PRIMARY | |||
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28821
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SUB35136
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M8854
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DTXSID3021805
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U71XL721QK
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94-62-2
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DB12582
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C008922
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PIPERINE
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CHEMBL43185
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1543200
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21727
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1311146
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PRIMARY | RxNorm | ||
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474
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202-348-0
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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