Page last updated: 2024-12-06

avarol

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Description

Avarol is a natural product isolated from the marine sponge Dysidea avara. It exhibits potent cytotoxic activity against various cancer cell lines. Its unique structure, featuring a bridged bicyclic ring system with a fused furan ring, has sparked interest in its synthesis and biological activity. Researchers are investigating its potential as a lead compound for the development of novel anticancer drugs. Avarol's mechanism of action is believed to involve the disruption of microtubule polymerization, leading to cell cycle arrest and apoptosis. The compound's biological activity and structural complexity have made it a target for synthetic chemists, who have developed several methods for its synthesis. These synthetic approaches provide access to analogues and derivatives of avarol, enabling structure-activity relationship studies and the exploration of new therapeutic applications.'

avarol: RN given refers to parent cpd; extract from Dysidea avara(sea sponge) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72185
CHEMBL ID459814
SCHEMBL ID186460
MeSH IDM0081136

Synonyms (22)

Synonym
55303-98-5
nsc-306951
avarol
1,4-benzenediol, 2-((1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl)methyl)-, (1r-(1-alpha,2-beta,4a-beta,8a-alpha))-
nsc 306951
(1r-(1alpha,2beta,4abeta,8abeta))-2-((1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl)methyl)-1,4-benzenediol
1,4-benzenediol,2-[(1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl)methyl]-,[1r-(1.alpha.,2.beta.,4a.beta.,8a.alpha.)]-
2-[[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]benzene-1,4-diol
bdbm50242257
2-(1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzene-1,4-diol(avarol)(avarol)
2-((1r,2s,4as)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzene-1,4-diol
CHEMBL459814 ,
avrol
unii-kzx416vn2b
kzx416vn2b ,
SCHEMBL186460
1,4-benzenediol, 2-(((1r,2s,4as,8as)-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl)methyl)-
(+)-avarol
JSPUCPNQXKTYRO-LWILDLIXSA-N
DTXSID80203850
Q27282525
1,4-benzenediol, 2-[[(1r,2s,4as,8as)-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl]methyl]-

Research Excerpts

Overview

Avarol is a marine sesquiterpenoid hydroquinone, previously isolated from the marine sponge Dysidea avara Schmidt (Dictyoceratida) Avarol has antiinflammatory, antitumor, antioxidant, antiplatelet, anti-HIV, and antipsoriatic effects.

ExcerptReferenceRelevance
"Avarol is a marine sesquiterpenoid hydroquinone, previously isolated from the marine sponge Dysidea avara Schmidt (Dictyoceratida), with antiinflammatory, antitumor, antioxidant, antiplatelet, anti-HIV, and antipsoriatic effects. "( Avarol derivatives as competitive AChE inhibitors, non hepatotoxic and neuroprotective agents for Alzheimer's disease.
Cañadas, S; García-Font, N; Iodice, C; Marco-Contelles, J; Oset-Gasque, MJ; Pejin, B; Tommonaro, G; Vitale, RM, 2016
)
3.32
"Avarol is a sesquiterpenoid hydroquinone with potent cytotoxicity. "( Avarol induces apoptosis in pancreatic ductal adenocarcinoma cells by activating PERK-eIF2α-CHOP signaling.
Kodama, R; Namba, T, 2015
)
3.3
"Avarol is a marine sesquiterpenoid hydroquinone with interesting pharmacological properties including anti-inflammatory and antipsoriatic effects. "( Avarol inhibits TNF-alpha generation and NF-kappaB activation in human cells and in animal models.
Amigó, M; Braza-Boïls, A; De Rosa, S; Payá, M; Terencio, MC, 2008
)
3.23
"Avarol is a sesquiterpenoid hydroquinone, which displays no inhibitory potencies on mammalian DNA polymerases alpha, beta, and gamma, on mammalian RNA polymerases I, II, and III, or on reverse transcriptases from Moloney murine leukemia virus (Mo-MuLV) and from HIV. "( Selective inhibition of formation of suppressor glutamine tRNA in Moloney murine leukemia virus-infected NIH-3T3 cells by Avarol.
Kuchino, Y; Müller, WE; Nishimura, S; Rottmann, M; Schröder, HC, 1988
)
1.93
"Avarol is a cytostatic and anti-human immunodeficiency virus (HIV) agent. "( Induction of gamma-interferon by avarol in human peripheral blood lymphocytes.
Bachmann, M; Hess, G; Laubenstein, HP; Meyer zum Büschenfelde, KH; Müller, WE; Reuter, P; Rossol, S; Schröder, HC; Voth, R, 1988
)
2

Effects

ExcerptReferenceRelevance
"Avarol has been shown to be able to modulate posttranscriptional events of mRNA synthesis, resulting in an increase of the base-sequence complexities of the nonabundant and rare mRNA classes."( Suppression of the modulatory effects of the antileukemic and anti-human immunodeficiency virus compound avarol on gene expression by tryptophan.
Gerner, H; Kuchino, Y; Müller, WE; Reuter, P; Schröder, HC; Sladić, D; Wenger, R, 1989
)
1.21

Actions

ExcerptReferenceRelevance
"Only avarol was able to inhibit human recombinant synovial phospholipase A2 activity with an IC50 = 158 microM, and thus this compound showed a potency higher than that of mepacrine."( Avarol and avarone, two new anti-inflammatory agents of marine origin.
Alcaraz, MJ; Bustos, G; De Rosa, S; Ferrándiz, ML; Payá, M; Sanz, MJ, 1994
)
2.19

Treatment

ExcerptReferenceRelevance
"Avarol treated cells did not show "unbalanced growth"."( Avarol, a cytostatically active compound from the marine sponge Dysidea avara.
Becker, C; Diehl-Seifert, B; Dogović, N; Eich, E; Gasić, MJ; Maidhof, A; Müller, WE; Zahn, RK, 1985
)
2.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)285.63000.00000.94539.9400AID1328951
Cytochrome P450 1A2Homo sapiens (human)IC50 (µMol)12.00000.00011.774010.0000AID1552374
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)12.00000.00053.49849.7600AID1321049
Prostaglandin G/H synthase 2Homo sapiens (human)IC50 (µMol)2.30000.00010.995010.0000AID403340
Sigma intracellular receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)14.80000.01431.37567.5000AID1552373
Sterol O-acyltransferase 1Cricetulus griseus (Chinese hamster)IC50 (µMol)12.00001.80001.80001.8000AID1552374
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (110)

Processvia Protein(s)Taxonomy
steroid catabolic processCytochrome P450 1A2Homo sapiens (human)
porphyrin-containing compound metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 1A2Homo sapiens (human)
cholesterol metabolic processCytochrome P450 1A2Homo sapiens (human)
estrogen metabolic processCytochrome P450 1A2Homo sapiens (human)
toxin biosynthetic processCytochrome P450 1A2Homo sapiens (human)
post-embryonic developmentCytochrome P450 1A2Homo sapiens (human)
alkaloid metabolic processCytochrome P450 1A2Homo sapiens (human)
regulation of gene expressionCytochrome P450 1A2Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 1A2Homo sapiens (human)
dibenzo-p-dioxin metabolic processCytochrome P450 1A2Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
lung developmentCytochrome P450 1A2Homo sapiens (human)
methylationCytochrome P450 1A2Homo sapiens (human)
monocarboxylic acid metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 1A2Homo sapiens (human)
retinol metabolic processCytochrome P450 1A2Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 1A2Homo sapiens (human)
cellular respirationCytochrome P450 1A2Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 1A2Homo sapiens (human)
hydrogen peroxide biosynthetic processCytochrome P450 1A2Homo sapiens (human)
oxidative demethylationCytochrome P450 1A2Homo sapiens (human)
cellular response to cadmium ionCytochrome P450 1A2Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 1A2Homo 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)
prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
response to oxidative stressProstaglandin G/H synthase 2Homo sapiens (human)
embryo implantationProstaglandin G/H synthase 2Homo sapiens (human)
learningProstaglandin G/H synthase 2Homo sapiens (human)
memoryProstaglandin G/H synthase 2Homo sapiens (human)
regulation of blood pressureProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell population proliferationProstaglandin G/H synthase 2Homo sapiens (human)
response to xenobiotic stimulusProstaglandin G/H synthase 2Homo sapiens (human)
response to nematodeProstaglandin G/H synthase 2Homo sapiens (human)
response to fructoseProstaglandin G/H synthase 2Homo sapiens (human)
response to manganese ionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vascular endothelial growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cyclooxygenase pathwayProstaglandin G/H synthase 2Homo sapiens (human)
bone mineralizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fever generationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic plasticityProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of synaptic transmission, dopaminergicProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin secretionProstaglandin G/H synthase 2Homo sapiens (human)
response to estradiolProstaglandin G/H synthase 2Homo sapiens (human)
response to lipopolysaccharideProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylationProstaglandin G/H synthase 2Homo sapiens (human)
response to vitamin DProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to heatProstaglandin G/H synthase 2Homo sapiens (human)
response to tumor necrosis factorProstaglandin G/H synthase 2Homo sapiens (human)
maintenance of blood-brain barrierProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of protein import into nucleusProstaglandin G/H synthase 2Homo sapiens (human)
hair cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of apoptotic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vasoconstrictionProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
decidualizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle cell proliferationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of inflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
response to glucocorticoidProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of calcium ion transportProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergicProstaglandin G/H synthase 2Homo sapiens (human)
response to fatty acidProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to mechanical stimulusProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to lead ionProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to ATPProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to hypoxiaProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to non-ionic osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to fluid shear stressProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of transforming growth factor beta productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of cell migration involved in sprouting angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fibroblast growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of platelet-derived growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cellular oxidant detoxificationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of neuroinflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to homocysteineProstaglandin G/H synthase 2Homo sapiens (human)
response to angiotensinProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (29)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 1A2Homo sapiens (human)
iron ion bindingCytochrome P450 1A2Homo sapiens (human)
protein bindingCytochrome P450 1A2Homo sapiens (human)
electron transfer activityCytochrome P450 1A2Homo sapiens (human)
oxidoreductase activityCytochrome P450 1A2Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 1A2Homo sapiens (human)
enzyme bindingCytochrome P450 1A2Homo sapiens (human)
heme bindingCytochrome P450 1A2Homo sapiens (human)
demethylase activityCytochrome P450 1A2Homo sapiens (human)
caffeine oxidase activityCytochrome P450 1A2Homo sapiens (human)
aromatase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activityCytochrome P450 1A2Homo 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)
peroxidase activityProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 2Homo sapiens (human)
protein bindingProstaglandin G/H synthase 2Homo sapiens (human)
enzyme bindingProstaglandin G/H synthase 2Homo sapiens (human)
heme bindingProstaglandin G/H synthase 2Homo sapiens (human)
protein homodimerization activityProstaglandin G/H synthase 2Homo sapiens (human)
metal ion bindingProstaglandin G/H synthase 2Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygenProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo 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)
nuclear inner membraneProstaglandin G/H synthase 2Homo sapiens (human)
nuclear outer membraneProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulumProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum lumenProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum membraneProstaglandin G/H synthase 2Homo sapiens (human)
caveolaProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
protein-containing complexProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (53)

Assay IDTitleYearJournalArticle
AID466601Antibacterial activity against Escherichia coli ATCC 35218 by serial dilution method2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID1552370Inhibition of SOAT in CHOK1 cell microsomal fraction using [1-14C]oleoyl-CoA as substrate measured after 5 mins by TLC based method2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Inhibition of neutral lipid synthesis by avarols from a marine sponge.
AID106308Cytotoxic activity against cultured cells of MEL-28 malign human melanoma.2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.
AID333171Inhibition of TPA-induced ROS production in human neutrophils at 5 uM by chemiluminescence2004Journal of natural products, Sep, Volume: 67, Issue:9
Potential antipsoriatic avarol derivatives as antioxidants and inhibitors of PGE(2) generation and proliferation in the HaCaT cell line.
AID392420Antiviral activity against HIV12009Bioorganic & medicinal chemistry letters, Jan-15, Volume: 19, Issue:2
A novel sesquiterpene quinone from Hainan sponge Dysidea villosa.
AID338271Antimicrobial activity against Escherichia coli DSM 1103 after 18 hrs by twofold serial dilution method1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID466581Cytotoxicity against human K562 cells by MTT assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID355616Toxicity in brine shrimp
AID1328975Neurotoxicity in human SH-SY5Y cells assessed as decrease in cell viability at 1 uM after 24 hrs by XTT assay2016European journal of medicinal chemistry, Oct-21, Volume: 122Avarol derivatives as competitive AChE inhibitors, non hepatotoxic and neuroprotective agents for Alzheimer's disease.
AID436265Toxicity against Artemia salina after 24 hrs2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID436261Antimicrobial activity against Bacillus subtilis subsp. spizizenii DMS 347 after 48 hrs by serial dilution method2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID333172Inhibition of TPA-induced ROS production in human neutrophils by chemiluminescence2004Journal of natural products, Sep, Volume: 67, Issue:9
Potential antipsoriatic avarol derivatives as antioxidants and inhibitors of PGE(2) generation and proliferation in the HaCaT cell line.
AID9027Cytotoxic activity against cultured cells of A-549 human lung carcinoma.2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.
AID333175Inhibition of PGE2 production in human HaCaT cells at 5 uM after 24 hrs by RIA2004Journal of natural products, Sep, Volume: 67, Issue:9
Potential antipsoriatic avarol derivatives as antioxidants and inhibitors of PGE(2) generation and proliferation in the HaCaT cell line.
AID338269Antimicrobial activity against Micrococcus luteus DSM 348 after 18 hrs by twofold serial dilution method1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID436260Antioxidant activity assessed as DPPH radical scavenging activity2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID355617Antitumor activity against Agrobacterium tumefaciens-induced crown gall tumors in potato tubers by potato disk assay
AID436263Antimicrobial activity against Saccharomyces cerevisiae DMS 70449 after 48 hrs by serial dilution method2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID466604Toxicity against freshly hatched nauplii of brine shrimp after 24 hrs2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID436262Antimicrobial activity against Micrococcus luteus DMS 348 after 48 hrs by serial dilution method2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID338268Antimicrobial activity against Bacillus subtilis DSM 347 after 18 hrs by twofold serial dilution method1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID83585Cytotoxic activity against cultured cells of HT-29 human colon carcinoma.2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.
AID338270Antimicrobial activity against Candida albicans DSM 1665 after 18 hrs by twofold serial dilution method1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID1328952Inhibition of equine serum BuChE using butyrylthiocholine iodide as substrate at 10 uM incubated for 15 mins followed by substrate addition by Ellman's method2016European journal of medicinal chemistry, Oct-21, Volume: 122Avarol derivatives as competitive AChE inhibitors, non hepatotoxic and neuroprotective agents for Alzheimer's disease.
AID436264Antimicrobial activity against Escherichia coli DSM 498 after 48 hrs by serial dilution method2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID333173Antiproliferative activity against human HaCaT cells assessed as [3H]thymidine incorporation at 5 uM after 24 hrs2004Journal of natural products, Sep, Volume: 67, Issue:9
Potential antipsoriatic avarol derivatives as antioxidants and inhibitors of PGE(2) generation and proliferation in the HaCaT cell line.
AID1552371Inhibition of DGAT in CHOK1 cell microsomal fraction using [14C]palmitoyl-CoA as substrate measured after 15 mins TLC based method2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Inhibition of neutral lipid synthesis by avarols from a marine sponge.
AID1552373Inhibition of African green monkey SOAT2 expressed in CHO cells using [1-14C]oleic acid incubated for 6 hrs by TLC based method2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Inhibition of neutral lipid synthesis by avarols from a marine sponge.
AID1552369Cytotoxicity against CHOK1 cells assessed as reduction in cell viability2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Inhibition of neutral lipid synthesis by avarols from a marine sponge.
AID466600Antibacterial activity against Staphylococcus aureus ATCC 25923 by serial dilution method2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID403340Inhibition of COX22005Journal of natural products, Jul, Volume: 68, Issue:7
Expanding the ChemGPS chemical space with natural products.
AID338274Toxicity against Gambusia affinis1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID1552372Inhibition of African green monkey SOAT1 expressed in CHO cells using [1-14C]oleic acid incubated for 6 hrs by TLC based method2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Inhibition of neutral lipid synthesis by avarols from a marine sponge.
AID338273Toxicity against Artemia salina after 24 hrs1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID152264Cytotoxic Activity against cultured cells of P-388 murine leukemia.2001Journal of medicinal chemistry, Apr-12, Volume: 44, Issue:8
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.
AID1552368Inhibition of DGAT-mediated oleic acid-induced [14C]neutral lipid synthesis in CHOK1 cells after 6 hrs using [14C]oleic acid by Oil Red O staining-based microscopic analysis2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Inhibition of neutral lipid synthesis by avarols from a marine sponge.
AID466579Cytotoxicity against human HeLa cells assessed as decrease in total cellular protein by kenacid blue R binding method2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID466583Cytotoxicity against human phytohemagglutininin-stimulated PBMC cells assessed as growth inhibition by MTT assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID1321049Inhibition of recombinant human PTP1B (1 to 322 residues) expressed in Escherichia coli using pNPP as substrate preincubated for 10 mins followed by substrate addition measured after 30 mins2016Journal of natural products, 07-22, Volume: 79, Issue:7
Sesquiterpene Hydroquinones with Protein Tyrosine Phosphatase 1B Inhibitory Activities from a Dysidea sp. Marine Sponge Collected in Okinawa.
AID1328951Inhibition of Electrophorus electricus AChE using acetylthiocholine iodide as substrate incubated for 15 mins followed by substrate addition by Ellman's method2016European journal of medicinal chemistry, Oct-21, Volume: 122Avarol derivatives as competitive AChE inhibitors, non hepatotoxic and neuroprotective agents for Alzheimer's disease.
AID436266Inhibition of acetylcholinesterase2008Journal of natural products, Nov, Volume: 71, Issue:11
Synthesis and biological activities of thio-avarol derivatives.
AID1328976Neurotoxicity in human SH-SY5Y cells assessed as decrease in cell viability at 25 to 50 uM after 24 hrs by XTT assay2016European journal of medicinal chemistry, Oct-21, Volume: 122Avarol derivatives as competitive AChE inhibitors, non hepatotoxic and neuroprotective agents for Alzheimer's disease.
AID1666597Induction of DNA damage in human SU8686 cells assessed as increase in gammaH2AX phosphorylation at ser193 at cytotoxic IC50 in presence of 0.3 uM doxorubicin by fluorometry method2020Bioorganic & medicinal chemistry, 02-15, Volume: 28, Issue:4
Targeting the DNA damage response (DDR) by natural compounds.
AID466582Cytotoxicity against human PBMC cells by MTT assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID466580Cytotoxicity against human Fem-X cells assessed as decrease in total cellular protein by kenacid blue R binding method2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Synthesis and biological activity of derivatives of the marine quinone avarone.
AID1552375Inhibition of SOAT2 in CHO cell microsomal fraction using [1-14C]oleoyl-CoA as substrate measured after 5 mins by TLC based method2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Inhibition of neutral lipid synthesis by avarols from a marine sponge.
AID1295995Inhibition of TNF alpha-induced NF-kappaB (unknown origin) activation in HEK293 cells after 6 hrs by luciferase reporter gene assay2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Dysiherbols A-C and Dysideanone E, Cytotoxic and NF-κB Inhibitory Tetracyclic Meroterpenes from a Dysidea sp. Marine Sponge.
AID1552367Inhibition of SOAT-mediated oleic acid-induced [14C]cholesterol ester accumulation in CHOK1 cells after 6 hrs using [14C]oleic acid by Oil Red O staining-based microscopic analysis2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Inhibition of neutral lipid synthesis by avarols from a marine sponge.
AID1552374Inhibition of SOAT1 in CHO cell microsomal fraction using [1-14C]oleoyl-CoA as substrate measured after 5 mins by TLC based method2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Inhibition of neutral lipid synthesis by avarols from a marine sponge.
AID333177Cytotoxicity against human HaCaT cells assessed as LDH release at 5 uM after 24 hrs2004Journal of natural products, Sep, Volume: 67, Issue:9
Potential antipsoriatic avarol derivatives as antioxidants and inhibitors of PGE(2) generation and proliferation in the HaCaT cell line.
AID338272Antimicrobial activity against Pseudomonas aeruginosa DSM 1117 after 18 hrs by twofold serial dilution method1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID333170Antioxidant activity assessed as DPPH free radical scavenging activity after 30 mins by TLC autographic assay2004Journal of natural products, Sep, Volume: 67, Issue:9
Potential antipsoriatic avarol derivatives as antioxidants and inhibitors of PGE(2) generation and proliferation in the HaCaT cell line.
AID1295996Cytotoxicity against human NCI-H929 cells after 48 hrs by MTS assay2016Journal of natural products, Feb-26, Volume: 79, Issue:2
Dysiherbols A-C and Dysideanone E, Cytotoxic and NF-κB Inhibitory Tetracyclic Meroterpenes from a Dysidea sp. Marine Sponge.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (64)

TimeframeStudies, This Drug (%)All Drugs %
pre-199018 (28.13)18.7374
1990's9 (14.06)18.2507
2000's17 (26.56)29.6817
2010's16 (25.00)24.3611
2020's4 (6.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 37.09

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

MetricThis Compound (vs All)
Research Demand Index37.09 (24.57)
Research Supply Index4.22 (2.92)
Research Growth Index4.56 (4.65)
Search Engine Demand Index53.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (37.09)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (4.48%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other64 (95.52%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]