Piplartine
Piplartine structure
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Common Name | Piplartine | ||
|---|---|---|---|---|
| CAS Number | 20069-09-4 | Molecular Weight | 317.336 | |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 475.6±45.0 °C at 760 mmHg | |
| Molecular Formula | C17H19NO5 | Melting Point | 124ºC | |
| MSDS | Chinese USA | Flash Point | 241.4±28.7 °C | |
Use of PiplartinePiperlongumine is a natural alkaloid isolated from Piper longum Linn[1], possesses ant-inflammatory, antibacterial, antiangiogenic, antioxidant, antitumor, and antidiabetic activities[2]. Piperlongumine induces ROS, and induces apoptosis in cancer cell lines[1]. Piperlongumine shows anti-cardiac fibrosis activity, suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway[2]. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | Piperlongumine |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | Piperlongumine is a natural alkaloid isolated from Piper longum Linn[1], possesses ant-inflammatory, antibacterial, antiangiogenic, antioxidant, antitumor, and antidiabetic activities[2]. Piperlongumine induces ROS, and induces apoptosis in cancer cell lines[1]. Piperlongumine shows anti-cardiac fibrosis activity, suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway[2]. |
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| Related Catalog | |
| Target |
ERK1 ERK2 |
| In Vitro | Piplartine (5, 10, and 15 μM) significantly decreases cell proliferation of 786-O, SKBR3, Panc1, A549, and L3.6pL cancer cells after treatment for 24 and 48 hours, induces apoptosis and ROS in these cell lines at 5 and 10 μM after 3 or 9 h of treatment[1]. Piplartine (5 or 10 μM) induces cleaved PARP and downregulates Sp1, Sp3, Sp4, and Sp-regulated genes[1]. Piplartine (20 μM) decreases the viability of cardiac fibroblasts (CFs). Piplartine (0-10 μM) suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway[2]. |
| In Vivo | Piperlongumine (30 mg/kg/day, i.p. for 3 weeks) exhibits potent anti-tumor effect in athymic nude mice bearing L3.6pL cells without body weight loss[1]. |
| References |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 475.6±45.0 °C at 760 mmHg |
| Melting Point | 124ºC |
| Molecular Formula | C17H19NO5 |
| Molecular Weight | 317.336 |
| Flash Point | 241.4±28.7 °C |
| Exact Mass | 317.126312 |
| PSA | 65.07000 |
| LogP | 2.34 |
| Appearance of Characters | white to beige |
| Vapour Pressure | 0.0±1.2 mmHg at 25°C |
| Index of Refraction | 1.581 |
| InChIKey | VABYUUZNAVQNPG-BQYQJAHWSA-N |
| SMILES | COc1cc(C=CC(=O)N2CCC=CC2=O)cc(OC)c1OC |
| Storage condition | 2-8°C |
| Water Solubility | DMSO: ≥5mg/mL at warmed to 60°C |
This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.
This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| RIDADR | NONH for all modes of transport |
|---|---|
| WGK Germany | 3 |
| RTECS | UU7785850 |
| HS Code | 2933399090 |
This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.
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~42%
Piplartine CAS#:20069-09-4 |
| Literature: Boll, Per M.; Hansen, Jesper; Simonsen, Ole; Thorup, Niels Tetrahedron, 1984 , vol. 40, # 1 p. 171 - 176 |
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~%
Piplartine CAS#:20069-09-4 |
| Literature: Tetrahedron, , vol. 40, # 1 p. 171 - 176 |
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~%
Piplartine CAS#:20069-09-4 |
| Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361 |
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~%
Piplartine CAS#:20069-09-4 |
| Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361 |
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~%
Piplartine CAS#:20069-09-4 |
| Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361 |
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~%
Piplartine CAS#:20069-09-4 |
| Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361 |
This table shows customs‑related data including HS‑code, tariff and regulatory conditions for import and export.
| HS Code | 2933399090 |
|---|---|
| Summary | 2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
This table lists relevant public references with title, journal and publication metadata for this compound.
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Serotonergic signalling suppresses ataxin 3 aggregation and neurotoxicity in animal models of Machado-Joseph disease.
Brain 138 , 3221-37, (2015) Polyglutamine diseases are a class of dominantly inherited neurodegenerative disorders for which there is no effective treatment. Here we provide evidence that activation of serotonergic signalling is... |
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Piperlongumine induces apoptotic and autophagic death of the primary myeloid leukemia cells from patients via activation of ROS-p38/JNK pathways.
Acta Pharmacol. Sin. 36(3) , 362-74, (2015) To investigate the effects of piperlongumine (PL), an anticancer alkaloid from long pepper plants, on the primary myeloid leukemia cells from patients and the mechanisms of action.Human BM samples wer... |
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Piperlongumine for Enhancing Oral Bioavailability and Cytotoxicity of Docetaxel in Triple-Negative Breast Cancer.
J. Pharm. Sci. 104 , 4417-26, (2016) Very low oral bioavailability due to extensive pre-systemic metabolism and P-gp efflux has constrained the oral metronomic chemotherapy of docetaxel (DTX). There is tremendous need of compounds facili... |
This table contains target information, in‑vitro & in‑vivo assay data for this compound.
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Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN
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Name: Antitrypanosomal activity against epimastigote forms of Trypanosoma cruzi Y after 72 ...
Source: ChEMBL
Target: Trypanosoma cruzi
External Id: CHEMBL3059482
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Name: Inhibition of MAPK/NFkappaB in ICR mouse RAW264.7 cells assessed as reduction in LPS-...
Source: ChEMBL
Target: N/A
External Id: CHEMBL4387890
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Name: Fluorescence-based cell-based primary high throughput screening assay to identify pos...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_PAM_FLUO8_1536_1X%ACT PRUN
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Name: Inhibition of MAPK/NFkappaB in ICR mouse RAW264.7 cells assessed as reduction in LPS-...
Source: ChEMBL
Target: N/A
External Id: CHEMBL4387892
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Name: Cytotoxicity against ICR mouse RAW264.7 cells assessed as effect on cell proliferatio...
Source: ChEMBL
Target: RAW264.7
External Id: CHEMBL4387894
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Name: Induction of autophagy in human MDA-MB-231 cells transfected with mRFP-eGFP-LC3 asses...
Source: ChEMBL
Target: MDA-MB-231
External Id: CHEMBL4773282
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Name: Induction of autophagy in human MDA-MB-231 cells transfected with mRFP-eGFP-LC3 asses...
Source: ChEMBL
Target: MDA-MB-231
External Id: CHEMBL4773281
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Name: Induction of autophagy in human MDA-MB-231 cells transfected with mRFP-eGFP-LC3 asses...
Source: ChEMBL
Target: MDA-MB-231
External Id: CHEMBL4773286
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Name: Induction of apoptosis in human MDA-MB-231 cells at 1.8 uM measured after 72 hrs by A...
Source: ChEMBL
Target: MDA-MB-231
External Id: CHEMBL4773274
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This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| Piperlongumine |
| 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one |
| (E)-Piplartine |
| 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone |
| piplartine |
| 1-[3-(3,4,5-Trimethoxy-phenyl)-acryloyl]-5,6-dihydro-1H-pyridin-2-one |
| 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: How is the water solubility of Piperlongumine? |
| A: Water solubility of Piperlongumine: DMSO: ≥5mg/mL at warmed to 60°C. |
| Q: What is the polar surface area (PSA) of Piperlongumine? |
| A: Polar surface area (PSA) of Piperlongumine is 65.07000. |
| Q: What is the molecular weight of Piperlongumine? |
| A: Molecular weight of Piperlongumine is 317.336. |
| Q: What is the InChIKey of Piperlongumine? |
| A: InChIKey of Piperlongumine is VABYUUZNAVQNPG-BQYQJAHWSA-N. |
| Q: What is the melting point of Piperlongumine? |
| A: Melting point of Piperlongumine is 124ºC. |
| Q: What is the boiling point of Piperlongumine? |
| A: Boiling point of Piperlongumine is 475.6±45.0 °C at 760 mmHg. |
| Q: What is the English name of Piperlongumine? |
| A: The English name of Piperlongumine is Piperlongumine. |
| Q: What is the LogP of Piperlongumine? |
| A: LogP of Piperlongumine is 2.34. |
| Q: What is the physical appearance of Piperlongumine? |
| A: Piperlongumine appears as white to beige. |
| Q: What is the SMILES notation of Piperlongumine? |
| A: SMILES notation of Piperlongumine is COc1cc(C=CC(=O)N2CCC=CC2=O)cc(OC)c1OC. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| BioBioPha |
| Henan Tianfu Chemical Co., Ltd. |