Page last updated: 2024-11-10

eupatoriopicrine

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Description

eupatoriopicrine: sesquiterpene lactone [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6438139
MeSH IDM0101809
PubMed CID5281461
CHEMBL ID221283
CHEMBL ID490011
CHEBI ID4937
MeSH IDM0101809

Synonyms (18)

Synonym
germacra-1(10),4,11(13)-trien-12-oic acid, 6-beta,8-alpha-dihydroxy-, 12,6-lactone, 4-hydroxy-2-(hydroxymethyl)crotonate
2-butaenoic acid, 4-hydroxy-2-(hydroxymethyl)-, (3ar,4r,6e,10e,11ar)-2,3,3a,4,5,8,9,11a-octahydro-8,10-dimethyl-3-methylene-2-oxocyclodeca(b)furan-4-yl ester, (2e)-
nsc 295427
eupatoriopicrine
6856-01-5
[(3ar,4r,6z,10z,11ar)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (e)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
C09442
eupatoriopicrin
bdbm50194428
CHEMBL221283 ,
CHEMBL490011 ,
chebi:4937 ,
[(3ar,4r,6e,10e,11ar)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (e)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
Q27106570
AKOS040761721
CS-0134007
HY-N7572
bdbm50586769
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
germacranolideA sesquiterpene lactone based on germacrane skeleton.
[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 Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Maltase-glucoamylase, intestinalHomo sapiens (human)IC50 (µMol)28.00000.04003.46529.0000AID1830872
UDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12IC50 (µMol)32.70000.10004.21698.8000AID276339
Tyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)IC50 (µMol)28.00000.70004.58049.4500AID1830871
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)28.00000.00053.49849.7600AID1830870
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (62)

Processvia Protein(s)Taxonomy
maltose catabolic processMaltase-glucoamylase, intestinalHomo sapiens (human)
starch catabolic processMaltase-glucoamylase, intestinalHomo sapiens (human)
dextrin catabolic processMaltase-glucoamylase, intestinalHomo sapiens (human)
peptidoglycan biosynthetic processUDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12
regulation of cell shapeUDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12
peptidoglycan biosynthetic processUDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12
UDP-N-acetylgalactosamine biosynthetic processUDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12
cell divisionUDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12
cell wall organizationUDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12
negative regulation of transcription by RNA polymerase IITyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of cell population proliferationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of tumor necrosis factor-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of lipid storageTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
B cell differentiationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
T cell differentiationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
erythrocyte differentiationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of epidermal growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of tyrosine phosphorylation of STAT proteinTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
glucose homeostasisTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of macrophage differentiationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
positive regulation of gluconeogenesisTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of inflammatory responseTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of T cell receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of chemotaxisTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
regulation of type II interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of type II interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of interleukin-6-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of interleukin-2-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of interleukin-4-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of macrophage colony-stimulating factor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of positive thymic T cell selectionTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
positive regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
positive regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
positive regulation of JUN kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
actin cytoskeleton organizationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of endocytosisTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulum unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of intracellular protein transportTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cellular response to unfolded proteinTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of MAP kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of protein tyrosine kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of receptor catabolic processTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
catalytic activityMaltase-glucoamylase, intestinalHomo sapiens (human)
glucan 1,4-alpha-glucosidase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
alpha-1,4-glucosidase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
protein bindingMaltase-glucoamylase, intestinalHomo sapiens (human)
amylase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
carbohydrate bindingMaltase-glucoamylase, intestinalHomo sapiens (human)
maltose alpha-glucosidase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
UDP-N-acetylglucosamine 1-carboxyvinyltransferase activityUDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12
transferase activityUDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
integrin bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
syntaxin bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
STAT family protein bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
RNA bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
zinc ion bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
enzyme bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cadherin bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
ephrin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein phosphatase 2A bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
plasma membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
apical plasma membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
extracellular exosomeMaltase-glucoamylase, intestinalHomo sapiens (human)
tertiary granule membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
ficolin-1-rich granule membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
cytoplasmUDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12
cytosolUDP-N-acetylglucosamine 1-carboxyvinyltransferaseEscherichia coli K-12
plasma membraneTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
nucleoplasmTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartmentTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
nucleusTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
plasma membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial matrixTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial cristaTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
sorting endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein-containing complexTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1830872Inhibition of alpha-glucosidase (unknown origin) using p-nitrophenyl-alpha-D-glucopyranoside as substrate incubated for 50 mins by microplate reader analysis2021Bioorganic & medicinal chemistry letters, 12-01, Volume: 53Germacrane sesquiterpenes from leaves of Eupatorium chinense inhibit protein tyrosine phosphatase.
AID1504892Cytotoxicity against rat L6 cells after 72 hrs by alamar blue staining based fluorescence assay2018Journal of natural products, 01-26, Volume: 81, Issue:1
Antiprotozoal Sesquiterpene Lactones and Other Constituents from Tarchonanthus camphoratus and Schkuhria pinnata.
AID1830870Inhibition of human recombinant PTP1B using pNPP as substrate assessed as reduction in p-nitrophenol release incubated for 30 mins by absorbance based analysis2021Bioorganic & medicinal chemistry letters, 12-01, Volume: 53Germacrane sesquiterpenes from leaves of Eupatorium chinense inhibit protein tyrosine phosphatase.
AID1830871Inhibition of human recombinant TCPTP using pNPP as substrate assessed as reduction in p-nitrophenol release incubated for 30 mins by absorbance based analysis2021Bioorganic & medicinal chemistry letters, 12-01, Volume: 53Germacrane sesquiterpenes from leaves of Eupatorium chinense inhibit protein tyrosine phosphatase.
AID1504893Selectivity index, ratio of IC50 for rat L6 cells to IC50 for Trypanosoma brucei rhodesiense STIB 900 bloodstream forms2018Journal of natural products, 01-26, Volume: 81, Issue:1
Antiprotozoal Sesquiterpene Lactones and Other Constituents from Tarchonanthus camphoratus and Schkuhria pinnata.
AID1504891Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB 900 bloodstream forms after 72 hrs by alamar blue staining based fluorescence assay2018Journal of natural products, 01-26, Volume: 81, Issue:1
Antiprotozoal Sesquiterpene Lactones and Other Constituents from Tarchonanthus camphoratus and Schkuhria pinnata.
AID276340Inhibition of Pseudomonas aeruginosa PAO1293 MurA in presence of UNAG2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA.
AID276343Inhibition of MurA at 10 uM2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA.
AID387024Cytotoxicity against human KB cells2008European journal of medicinal chemistry, Oct, Volume: 43, Issue:10
Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones.
AID276341Inhibition of Escherichia coli K12 Mur A C115D at 50 uM in presence of UNAG2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA.
AID338835Cytotoxicity against mouse EAC after 3 days by MTT assay1993Journal of natural products, Jun, Volume: 56, Issue:6
Cytotoxicity of artemisinin-related endoperoxides to Ehrlich ascites tumor cells.
AID276339Inhibition of Escherichia coli K12 Mur A in presence of UNAG2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (46.15)18.7374
1990's1 (7.69)18.2507
2000's2 (15.38)29.6817
2010's2 (15.38)24.3611
2020's2 (15.38)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%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]