piperyline: amide alkaloid isolated from P. nigrum [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
piperyline : A N-acylpyrrolidine that is pyrollidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Piper | genus | A plant genus of the family PIPERACEAE that includes species used for spicy and stimulating qualities.[MeSH] | Piperaceae | A family of flowering plants in the order Piperales best known for the black pepper widely used in SPICES, and for KAVA and Betel used for neuroactive properties.[MeSH] |
| ID Source | ID |
|---|---|
| PubMed CID | 636537 |
| CHEMBL ID | 1087296 |
| CHEBI ID | 9691 |
| SCHEMBL ID | 16274586 |
| Synonym |
|---|
| pyrrolidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)- |
| 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)pyrrolidine |
| 54976-54-4 |
| MEGXP0_000203 |
| NCGC00180828-01 |
| ACON1_000155 |
| 25924-78-1 |
| piperyline |
| trichostachine |
| BRD-K64601708-001-01-6 |
| chebi:9691 , |
| CHEMBL1087296 |
| pyrroperine |
| gv0493sm38 , |
| trichostachin |
| unii-gv0493sm38 |
| 2e,4e)-5-(2h-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one |
| piperylin |
| piperiline |
| (2e,4e)-5-(1,3-benzodioxol-5-yl)-1-(1-pyrrolidinyl)-2,4-pentadien-1-one |
| (2e,4e)-5-(2h-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one |
| (2e,4e)-5-(1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one |
| 1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]pyrrolidine |
| pyrrolidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (e,e)- |
| pyrrolidine, 1-piperoyl-, (e,e)- |
| 1-[(2e,4e)-5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl]pyrrolidine # |
| pyrrolidine, 1-((2e,4e)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)- |
| piperyline (constituent of black pepper) [dsc] |
| DTXSID20180595 , |
| SCHEMBL16274586 |
| (e,e)-trichostachine |
| piperyline, analytical standard |
| dtxcid60103086 |
| piperyline (constituent of black pepper) |
| (2e,4e)-5-(benzo[d][1,3]dioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-diene-1-one |
| 1-piperoyl-(e,e)-pyrrolidine |
| Q27108470 |
| 5-(2h-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one |
Piperyline (PIPE) is a further amide alkaloid that has been isolated from P. Piperyline is an anti-inflammatory drug.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Piperyline (PIPE) is a further amide alkaloid that has been isolated from P." | ( Effects of the amide alkaloid piperyline on apoptosis, autophagy, and differentiation of pre-osteoblasts. Cho, M; Kang, SW; Leem, HH; Park, KR; Yun, HM, 2020) | 1.57 |
| Role | Description |
|---|---|
| plant metabolite | Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| apoptosis inducer | Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. |
| antifungal agent | An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| benzodioxoles | |
| N-acylpyrrolidine | |
| tertiary carboxamide | A carboxamide resulting from the formal condensation of a carboxylic acid with a secondary amine; formula RC(=O)NHR(1)R(2). |
| pyrrolidine alkaloid | |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Fatty-acid amide hydrolase 1 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 61.3000 | 0.0005 | 1.3313 | 8.0000 | AID1571447 |
| N-acylethanolamine-hydrolyzing acid amidase | Rattus norvegicus (Norway rat) | IC50 (µMol) | 4.1000 | 4.1000 | 4.1000 | 4.1000 | AID1571446 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1515249 | Potentiation of ciprofloxacin-induced antibacterial activity in Staphylococcus aureus 1199 assessed as reduction in ciprofloxacin MIC at 0.8 to 50 ug/ml by broth checkerboard microdilution method relative to control | 2019 | Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2 | Synthesis of amides from (E)-3-(1-chloro-3,4-dihydronaphthalen-2-yl)acrylic acid and substituted amino acid esters as NorA efflux pump inhibitors of Staphylococcus aureus. |
| AID465670 | Activation of rat GABA alpha-1-beta-2-gamma-2 receptor expressed in xenopus oocytes assessed as potentiation of GABA-induced chloride current at 100 uM after 90 secs by two microplate electrode voltage clamp assay | 2010 | Journal of natural products, Feb-26, Volume: 73, Issue:2 | HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site. |
| AID465673 | Activation of rat GABA alpha-1-beta-2-gamma-2 receptor expressed in xenopus oocytes assessed as potentiation of chloride current at 100 uM after 90 secs by two microplate electrode voltage clamp assay | 2010 | Journal of natural products, Feb-26, Volume: 73, Issue:2 | HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site. |
| AID1515246 | Inhibition of NorA in Staphylococcus aureus 1199B assessed as minimum concentration required to effectively reduce ciprofloxacin MIC by four fold by broth checkerboard microdilution method | 2019 | Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2 | Synthesis of amides from (E)-3-(1-chloro-3,4-dihydronaphthalen-2-yl)acrylic acid and substituted amino acid esters as NorA efflux pump inhibitors of Staphylococcus aureus. |
| AID1571446 | Inhibition of rat NAAA expressed in HEK293 cells using heptadecenoylethanolamide as substrate after 30 mins HPLC-MS/MS analysis | 2019 | MedChemComm, Feb-01, Volume: 10, Issue:2 | Synthesis, biological evaluation, and structure activity relationship (SAR) study of pyrrolidine amide derivatives as |
| AID1515248 | Inhibition of NorA in Staphylococcus aureus 1199B assessed as reduction in ethidium bromide efflux at 50 uM measured over 5 mins interval for 30 mins by fluorescence assay relative to control | 2019 | Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2 | Synthesis of amides from (E)-3-(1-chloro-3,4-dihydronaphthalen-2-yl)acrylic acid and substituted amino acid esters as NorA efflux pump inhibitors of Staphylococcus aureus. |
| AID1515256 | Growth inhibition of Staphylococcus aureus 1199 at 50 ug/ml by broth microdilution method | 2019 | Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2 | Synthesis of amides from (E)-3-(1-chloro-3,4-dihydronaphthalen-2-yl)acrylic acid and substituted amino acid esters as NorA efflux pump inhibitors of Staphylococcus aureus. |
| AID1866568 | Inhibition of PI3K/AKT signalling pathway in patient-derived MM121224 cells harboring BRAF V600E/NRAS Q61K mutant coexpressing mutated forkhead box protein 1 allele fused mNeonGreen fluorophore at 200 uM incubated for 2 hrs | 2022 | Journal of natural products, 04-22, Volume: 85, Issue:4 | High-Content Screening Pipeline for Natural Products Targeting Oncogenic Signaling in Melanoma. |
| AID1515257 | Growth inhibition of norA-deleted Staphylococcus aureus K1758 at 50 ug/ml by broth microdilution method | 2019 | Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2 | Synthesis of amides from (E)-3-(1-chloro-3,4-dihydronaphthalen-2-yl)acrylic acid and substituted amino acid esters as NorA efflux pump inhibitors of Staphylococcus aureus. |
| AID1515250 | Potentiation of ciprofloxacin-induced antibacterial activity in norA-deleted Staphylococcus aureus K1758 assessed as reduction in ciprofloxacin MIC at 0.8 to 50 ug/ml by broth checkerboard microdilution method relative to control | 2019 | Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2 | Synthesis of amides from (E)-3-(1-chloro-3,4-dihydronaphthalen-2-yl)acrylic acid and substituted amino acid esters as NorA efflux pump inhibitors of Staphylococcus aureus. |
| AID1515258 | Inhibition of NorA in Staphylococcus aureus 1199B assessed as reduction in ethidium bromide accumulation at 25 uM measured at 5 mins interval for 60 mins by fluorescence assay relative to control | 2019 | Bioorganic & medicinal chemistry, 01-15, Volume: 27, Issue:2 | Synthesis of amides from (E)-3-(1-chloro-3,4-dihydronaphthalen-2-yl)acrylic acid and substituted amino acid esters as NorA efflux pump inhibitors of Staphylococcus aureus. |
| AID1866565 | Inhibition of MAPK/ERK signalling pathway in human A2058 cells harbouring BRAF V600E and PTEN deletion mutant coexpressing ERK-KTR fused mScarlett fluorophore at 1.56 to 200 uM incubated for 2 hrs by high-content screening microscopic analysis | 2022 | Journal of natural products, 04-22, Volume: 85, Issue:4 | High-Content Screening Pipeline for Natural Products Targeting Oncogenic Signaling in Melanoma. |
| AID1571447 | Inhibition of rat FAAH expressed in HEK293 cells using [3H]AEA as substrate after 30 mins HPLC-MS/MS analysis | 2019 | MedChemComm, Feb-01, Volume: 10, Issue:2 | Synthesis, biological evaluation, and structure activity relationship (SAR) study of pyrrolidine amide derivatives as |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 0 (0.00) | 29.6817 |
| 2010's | 3 (60.00) | 24.3611 |
| 2020's | 2 (40.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (22.50) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (20.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 4 (80.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||