Page last updated: 2024-12-07

piperic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

piperinic acid: from Piper longum; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(E,E)-piperic acid : A monocarboxylic acid that is (E)-penta-2,4-dienoic acid substituted by a 1,3-benzodioxol-5-yl group at position 5. It has been isolated from black pepper (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]

Cross-References

ID SourceID
PubMed CID5370536
CHEMBL ID332122
CHEBI ID37316
SCHEMBL ID447578
MeSH IDM0068574

Synonyms (40)

Synonym
2, 5-(1,3-benzodioxol-5-yl)-
piperic acid
nsc129538 ,
nsc-129538
piperic acid (e,e)-form
136-72-1
trans,trans-piperinic acid
CHEBI:37316 ,
(2e,4e)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoic acid
(e,e)-piperic acid
NCI129538
CHEMBL332122
AKOS005084354
bdbm50381226
CCG-37574
gfg3fla9ur ,
unii-gfg3fla9ur
2,4-pentadienoic acid, 5-(1,3-benzodioxol-5-yl)-, (e,e)-
piperinic acid
(e,e)-piperonic acid
SCHEMBL447578
1X-0937
(2e,4e)-5-(2h-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid
piperic acid [mi]
(e,e)-5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid
piperic acid, (e,e)-
5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid
5-(1,3-benzodioxol-5-yl)-2,4-pentadienoic acid, 97%
SR-01000309042-2
SR-01000309042-1
sr-01000309042
piperinsaure
J-006896
(2e,4e)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoic acid
Q1111585
DTXSID801016979
5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoicacid
5-(3,4-methylenedioxyphenyl)-2,4-pentadienoicacid
(2e,4e)-5-(1,3-dioxaindan-5-yl)penta-2,4-dienoic acid
EN300-7461567

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" A liquid chromatography-tandem mass spectrometry method was applied to determine the oral bioavailability of ethyl piperate."( Contribution of carboxylesterase in hamster to the intestinal first-pass loss and low bioavailability of ethyl piperate, an effective lipid-lowering drug candidate.
Bao, N; Borjihan, G; Hu, M; Jia, J; Li, S; Lu, Y; Ma, Y; Wang, Y; Yang, D; Yu, C, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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]

Drug Classes (2)

ClassDescription
benzodioxoles
alpha,beta-unsaturated monocarboxylic acidA monocarboxylic acid in which the carbon of the carboxy group is directly attached to a C=C or C#C bond.
[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]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID364269Antibacterial activity against Klebsiella aerogenes after 18 hrs by broth microdilution susceptibility test2008European journal of medicinal chemistry, Sep, Volume: 43, Issue:9
Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties.
AID364270Antibacterial activity against Staphylococcus saprophyticus after 18 hrs by broth microdilution susceptibility test2008European journal of medicinal chemistry, Sep, Volume: 43, Issue:9
Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties.
AID1519693Inhibition of human microsomal MAO-A expressed in baculovirus infected BTI-TN-5B1-4 cells assessed as reduction in 4-hydroxyquinoline formation at 10 uM using kynuramine as substrate preincubated with substrate for 10 mins followed by enzyme inhibition by2020European journal of medicinal chemistry, Jan-01, Volume: 185Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID609508Cytotoxicity against human HCT116 cells after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16
Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.
AID213669In vitro growth inhibition of epimastigotes of Trypanosoma cruzi2004Bioorganic & medicinal chemistry letters, Jul-05, Volume: 14, Issue:13
Toxic effects of natural piperine and its derivatives on epimastigotes and amastigotes of Trypanosoma cruzi.
AID1220529Drug metabolism in hamster assessed as appearance rate of compound in intestine treated with 400 uM of ethyl piperate administered as intestinal single-pass perfusion up to 1 hr by LC-MS/MS analysis in presence of BNPP2011Drug metabolism and disposition: the biological fate of chemicals, May, Volume: 39, Issue:5
Contribution of carboxylesterase in hamster to the intestinal first-pass loss and low bioavailability of ethyl piperate, an effective lipid-lowering drug candidate.
AID494525Cytotoxicity against human PBMC at 2 times IC50 concentration after 48 hrs by MTT assay2010European journal of medicinal chemistry, Aug, Volume: 45, Issue:8
Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID609509Inhibition of human recombinant HDAC1 expressed in baculovirus infected insect High5 cells using Ac-Lys-Tyr-Lys(epsilon-acetyl)-AMC as substrate at 20 ug/ml by fluorescence assay2011Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16
Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.
AID657239Selectivity ratio of IC50 for Sprague-Dawley rat MAO-B to IC50 for Sprague-Dawley rat MAO-A2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Synthesis and inhibitory effect of piperine derivates on monoamine oxidase.
AID496817Antimicrobial activity against Trypanosoma cruzi2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID494522Antileishmanial activity against Leishmania donovani amastigotes after 48 hrs by MTT assay2010European journal of medicinal chemistry, Aug, Volume: 45, Issue:8
Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID1220548Drug metabolism in hamster assessed as appearance rate of compound in portal vein treated with 400 uM of ethyl piperate administered as intestinal single-pass perfusion up to 1 hr by LC-MS/MS analysis2011Drug metabolism and disposition: the biological fate of chemicals, May, Volume: 39, Issue:5
Contribution of carboxylesterase in hamster to the intestinal first-pass loss and low bioavailability of ethyl piperate, an effective lipid-lowering drug candidate.
AID436579Inhibition of NorA efflux pump in Staphylococcus aureus 1199B assessed as accumulation of ethidium bromide after 24 hrs by broth checkerboard method2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Quantitative structure activity relationship (QSAR) of piperine analogs for bacterial NorA efflux pump inhibitors.
AID1637507Inhibition of NorA efflux pump overexpressed in Staphylococcus aureus 1199B assessed as concentration required for four-fold reduction in ciprofloxacin MIC measured after 24 hrs by broth checkerboard method relative to control2016Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17
Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID494524Cytotoxicity against human PBMC at IC50 concentration after 48 hrs by MTT assay2010European journal of medicinal chemistry, Aug, Volume: 45, Issue:8
Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID1637508Inhibition of NorA efflux pump overexpressed in Staphylococcus aureus 1199B assessed as fold reduction in ciprofloxacin MIC at 12.5 ug/ml measured after 24 hrs by broth checkerboard method2016Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17
Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID1220523Apparent permeability coefficient of compound in hamster treated with 400 uM of ethyl piperate administered as intestinal single-pass perfusion up to 1 hr by LC-MS/MS analysis2011Drug metabolism and disposition: the biological fate of chemicals, May, Volume: 39, Issue:5
Contribution of carboxylesterase in hamster to the intestinal first-pass loss and low bioavailability of ethyl piperate, an effective lipid-lowering drug candidate.
AID1519694Inhibition of human microsomal MAO-B expressed in baculovirus infected BTI-TN-5B1-4 cells assessed as reduction in 4-hydroxyquinoline formation at 10 uM using kynuramine as substrate preincubated with substrate for 10 mins followed by enzyme addition by s2020European journal of medicinal chemistry, Jan-01, Volume: 185Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.
AID364074Antibacterial activity against Klebsiella aerogenes at 20 umol/ml after 24 hrs by Kirby-Bauer's disk diffusion assay2008European journal of medicinal chemistry, Sep, Volume: 43, Issue:9
Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties.
AID609510Inhibition of human recombinant HDAC3 expressed in baculovirus infected insect High5 cells using Ac-Lys-Tyr-Lys(epsilon-acetyl)-AMC as substrate at 20 ug/ml by fluorescence assay2011Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16
Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.
AID213668In vitro growth inhibition of amastigotes of Trypanosoma cruzi; Not tested2004Bioorganic & medicinal chemistry letters, Jul-05, Volume: 14, Issue:13
Toxic effects of natural piperine and its derivatives on epimastigotes and amastigotes of Trypanosoma cruzi.
AID1220520Drug metabolism in hamster assessed as appearance rate of compound in intestine treated with 400 uM of ethyl piperate administered as intestinal single-pass perfusion up to 1 hr by LC-MS/MS analysis2011Drug metabolism and disposition: the biological fate of chemicals, May, Volume: 39, Issue:5
Contribution of carboxylesterase in hamster to the intestinal first-pass loss and low bioavailability of ethyl piperate, an effective lipid-lowering drug candidate.
AID436580Inhibition of NorA efflux pump in Staphylococcus aureus 1199B assessed as reduction of ciprofloxacin MIC after 24 hrs by broth checkerboard method2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Quantitative structure activity relationship (QSAR) of piperine analogs for bacterial NorA efflux pump inhibitors.
AID609511Inhibition of human recombinant HDAC6 expressed in baculovirus infected insect High5 cells using Boc-Lys(epsilon-acetyl)-AMC as substrate at 20 ug/ml by fluorescence assay2011Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16
Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.
AID1220526Drug metabolism in hamster assessed as appearance rate of compound in portal vein treated with 400 uM of ethyl piperate administered as intestinal single-pass perfusion up to 1 hr by LC-MS/MS analysis in presence of BNPP2011Drug metabolism and disposition: the biological fate of chemicals, May, Volume: 39, Issue:5
Contribution of carboxylesterase in hamster to the intestinal first-pass loss and low bioavailability of ethyl piperate, an effective lipid-lowering drug candidate.
AID364272Antibacterial activity against Escherichia coli after 18 hrs by broth microdilution susceptibility test2008European journal of medicinal chemistry, Sep, Volume: 43, Issue:9
Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties.
AID657237Inhibition of MAO-A in Sprague-Dawley rat brain homogenate using kynuramine as substrate preincubated for 10 mins measured by fluorimetric assay2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Synthesis and inhibitory effect of piperine derivates on monoamine oxidase.
AID1220553Apparent permeability coefficient of compound in hamster treated with 400 uM of ethyl piperate administered as intestinal single-pass perfusion up to 1 hr by LC-MS/MS analysis in presence of BNPP2011Drug metabolism and disposition: the biological fate of chemicals, May, Volume: 39, Issue:5
Contribution of carboxylesterase in hamster to the intestinal first-pass loss and low bioavailability of ethyl piperate, an effective lipid-lowering drug candidate.
AID1637509Antibacterial activity against Staphylococcus aureus 1199B overexpressing NorA efflux pump measured after 24 hrs by broth checkerboard method2016Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17
Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus.
AID657238Inhibition of MAO-B in Sprague-Dawley rat brain homogenate using kynuramine as substrate preincubated for 10 mins measured by fluorimetric assay2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
Synthesis and inhibitory effect of piperine derivates on monoamine oxidase.
AID494523Antileishmanial activity against Leishmania donovani promastigotes after 48 hrs by MTT assay2010European journal of medicinal chemistry, Aug, Volume: 45, Issue:8
Synthesis and antileishmanial activity of piperoyl-amino acid conjugates.
AID1224817Assays to identify small molecules inhibitory for eIF4E expression2015Chemistry & biology, Jul-23, Volume: 22, Issue:7
Internal Ribosome Entry Site-Based Bicistronic In Situ Reporter Assays for Discovery of Transcription-Targeted Lead Compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.03)18.7374
1990's0 (0.00)18.2507
2000's5 (15.15)29.6817
2010's17 (51.52)24.3611
2020's10 (30.30)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other33 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]