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+
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 |
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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 |
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Primary | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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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 |
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Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
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Role of cytochrome P450 2B1 in puromycin aminonucleoside-induced cytotoxicity to glomerular epithelial cells. | 2003 |
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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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Identification of kaempferol as an inhibitor of cigarette smoke-induced activation of the aryl hydrocarbon receptor and cell transformation. | 2007 Mar |
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Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening. | 2011 |
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Anti-HBV active constituents from Piper longum. | 2013 Apr 1 |
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Piperine potentiates the antidepressant-like effect of trans-resveratrol: involvement of monoaminergic system. | 2013 Dec |
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Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells. | 2013 Oct |
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Mitigating efficacy of piperine in the physiological derangements of high fat diet induced obesity in Sprague Dawley rats. | 2014 Sep 25 |
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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.
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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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638024
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C72629
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U71XL721QK
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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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100000128291
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1311146
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474
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202-348-0
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ACTIVE MOIETY