Page last updated: 2024-12-07

echinuline

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

Description

Echinuline is a mycotoxin produced by various fungi, including Aspergillus and Penicillium species. It has been isolated from different sources, such as food, soil, and air. Research has shown that echinuline possesses a wide range of biological activities, including cytotoxic, antibacterial, and antifungal properties. Its structure consists of a pyrrolo[1,2-a]indole ring system, which is believed to be responsible for its biological activity. Echinuline has been studied extensively due to its potential health effects, including its toxicity to humans and animals. Studies have investigated its effects on various biological systems, such as the nervous system, immune system, and reproductive system. The synthesis of echinuline has been achieved through various chemical methods, and its biosynthesis has been studied in detail. Understanding the biosynthesis and biological activities of echinuline is essential for assessing its potential risks and developing strategies for its control.'

echinuline: tri-isoprenylated cyclic dipeptide from Aspergillus amstelodami; structure; Rn given refers to (3S-cis)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

echinulin : An indole alkaloid with formula C29H39N3O2. It is a fungal metabolite found in several Aspergillus species. [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 CID115252
CHEMBL ID251450
CHEBI ID68193
MeSH IDM0041228

Synonyms (22)

Synonym
2,5-piperazinedione, 3-((2-(1,1-dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1h-indol-3-yl)methyl)-6-methyl-, (3s,6s)-
1859-87-6
echinuline
(3s,6s)-3-[[2-(1,1-dimethylallyl)-5,7-bis(3-methylbut-2-enyl)-1h-indol-3-yl]methyl]-6-methyl-piperazine-2,5-dione
bdbm50223401
CHEMBL251450 ,
echinulin
(3s,6s)-3-methyl-6-{[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}piperazine-2,5-dione
(3s,6s)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-enyl)-1h-indol-3-yl]methyl]piperazine-2,5-dione
unii-3dp19vpn8u
3-((2-(1,1-dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1h-indol-3-yl)methyl)-6-methyl-2,5-piperazinedione
3dp19vpn8u ,
(3s,6s)-3-[[2-(1,1-dimethyl-2-propen-1-yl)-5,7-bis(3-methyl-2-buten-1-yl)-1h-indol-3-yl]methyl]-6-methyl-2,5-piperazinedione
CHEBI:68193
echinuline [mi]
AKOS030213189
NCGC00386111-01
2,5-piperazinedione, 3-[[2-(1,1-dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1h-indol-3-yl]methyl]-6-methyl-, (3s,6s)-
Q27257084
CS-0024238
BAA85987
HY-N3796

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
Aspergillus metaboliteAny fungal metabolite produced during a metabolic reaction in the mould, Aspergillus.
marine metaboliteAny metabolite produced during a metabolic reaction in marine macro- and microorganisms.
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 (4)

ClassDescription
indolesAny compound containing an indole skeleton.
2,5-diketopiperazinesAny piperazinone that has a piperazine-2,5-dione skeleton.
olefinic compoundAny organic molecular entity that contains at least one C=C bond.
indole alkaloidAn alkaloid containing an indole 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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Nitric oxide synthase, inducibleMus musculus (house mouse)IC50 (µMol)50.00000.00103.39119.6000AID344829
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1085772Antibacterial activity against Mycobacterium intracellulare ATCC 230682012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID610904Binding affinity at human mu opioid receptor expressed in CHO-K1 cells at 10 uM2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
AID610905Binding affinity at human CB1 receptor expressed in CHO-K1 cells at 10 uM2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
AID610902Binding affinity at human delta opioid receptor expressed in CHO-K1 cells at 10 uM2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
AID1225534Toxicity in brine shrimp assessed as mortality2015Journal of natural products, Apr-24, Volume: 78, Issue:4
Rubrumazines A-C, Indolediketopiperazines of the Isoechinulin Class from Eurotium rubrum MA-150, a Fungus Obtained from Marine Mangrove-Derived Rhizospheric Soil.
AID311562DPPH radical scavenging activity2007Journal of natural products, Oct, Volume: 70, Issue:10
Isoechinulin-type alkaloids, variecolorins A-L, from halotolerant Aspergillus variecolor.
AID610906Binding affinity at human CB2 receptor expressed in CHO-K1 cells at 10 uM2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
AID1085767Antifungal activity against Pichia kudriavzevii ATCC 6258 at 20 ug/ml2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085765Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 33591 at 20 ug/ml2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085774Antibacterial activity against Escherichia coli ATCC 352182012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID610903Binding affinity at human kappa opioid receptor expressed in CHO-K1 cells at 10 uM2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
AID1085763Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 after 72 hr by plasmodial LDH assay2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID344829Inhibition of iNOS-mediated NO production in LPS-induced mouse BV2 cells2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
New diterpenoids and the bioactivity of Erythrophleum fordii.
AID1085766Antibacterial activity against Staphylococcus aureus ATCC 29213 at 20 ug/ml2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1320314Inhibition of melanogenesis in theophylline-stimulated mouse B16-4A5 cells assessed as reduction in melanin level incubated for 72 hrs2016Bioorganic & medicinal chemistry letters, 10-15, Volume: 26, Issue:20
Conditional changes enhanced production of bioactive metabolites of marine derived fungus Eurotium rubrum.
AID1085762Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 after 72 hr by plasmodial LDH assay2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085761Cytotoxicity against Chlorocebus aethiops (African green monkey) Vero cells after 48 hr by neutral red assay2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085764Antileishmanial activity against promastigote form of Leishmania donovani after 48 hr by alamar blue assay2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID344828Inhibition of NADPH oxidase in LPS-induced mouse BV2 cells assessed as NOX-dependent ROS production at 50 uM2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
New diterpenoids and the bioactivity of Erythrophleum fordii.
AID1085768Antifungal activity against Cryptococcus neoformans ATCC 90113 at 20 ug/ml2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID670892Antibacterial activity against Staphylococcus aureus assessed as inhibition zone at 100 ug/disc by well diffusion method2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Cristatumins A-D, new indole alkaloids from the marine-derived endophytic fungus Eurotium cristatum EN-220.
AID1085771Antifungal activity against Candida albicans ATCC 900282012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085769Antifungal activity against Candida glabrata ATCC 90030 at 20 ug/ml2012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1200482Antiviral activity against influenza A virus A/WSN/33 (H1N1) infected in MDCK cells assessed as reduction in cytopathic effect at 100 uM after 48 hrs by plaque assay2015European journal of medicinal chemistry, Mar-26, Volume: 93Neoechinulin B and its analogues as potential entry inhibitors of influenza viruses, targeting viral hemagglutinin.
AID1085770Antifungal activity against Aspergillus fumigatus ATCC 2043052012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1085773Antibacterial activity against Pseudomonas aeruginosa ATCC 278532012Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, Oct, Volume: 21, Issue:10
Antimicrobial and antiprotozoal activities of secondary metabolites from the fungus Eurotium repens.
AID1200484Cytotoxicity against MDCK cells assessed as cell growth after 40 hrs by CellTiter-Glo assay2015European journal of medicinal chemistry, Mar-26, Volume: 93Neoechinulin B and its analogues as potential entry inhibitors of influenza viruses, targeting viral hemagglutinin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (15.00)18.7374
1990's1 (5.00)18.2507
2000's2 (10.00)29.6817
2010's10 (50.00)24.3611
2020's4 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.33

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.33 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index5.38 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.33)

All Compounds (24.57)

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%
Other20 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]