Page last updated: 2024-11-12

7-phloroeckol

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

Description

7-phloroeckol: isolated from Ecklonia cava; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

7-phloroeckol : A phlorotannin that is eckol in which the hydroxy group at position 7 is replaced by a 2,4,6-trihydroxyphenoxy group. Isolated from the marine brown alga, Ecklonia cava, it exhibits antioxidant activity. [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 CID10480940
CHEMBL ID456228
CHEBI ID65790
SCHEMBL ID10271928
MeSH IDM0557841

Synonyms (19)

Synonym
1-(3',5'-dihydroxyphenoxy)-7-(2'',4'',6''-trihydroxyphenoxy)-2,4,9-trihydroxydibenzo-1,4-dioxin
4-(3,5-dihydroxyphenoxy)-8-(2,4,6-trihydroxyphenoxy)oxanthrene-1,3,6-triol
(1-(3'',5''-dihydroxyphenoxy)-7-(2'''',4'''',6-trihydro-xyphenoxy)-2,4,9-trihydroxydibenzo-1,4-dioxin)
bdbm50276826
7-phloroethol
CHEMBL456228 ,
chebi:65790 ,
7-phloroeckol
SCHEMBL10271928
Q4642878
dibenzo(b,e)(1,4)dioxin-1,3,6-triol, 4-(3,5-dihydroxyphenoxy)-8-(2,4,6-trihydroxyphenoxy)-
97GCC12YF0 ,
unii-97gcc12yf0
4-(3,5-dihydroxyphenoxy)-8-(2,4,6-trihydroxyphenoxy)dibenzo(b,e)(1,4)dioxin-1,3,6-triol
662165-35-7
7-phloroglucinoleckol
4-(3,5-dihydroxyphenoxy)-8-(2,4,6-trihydroxyphenoxy)dibenzo-p-dioxin-1,3,6-triol
DTXSID201030418
PD183177
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
EC 3.1.1.3 (triacylglycerol lipase) inhibitorAny EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of triacylglycerol lipase (EC 3.1.1.3).
[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
phlorotanninA type of tannin usually found in brown algae such as kelps and rockweeds. Unlike the hydrolysable or condensed tannins, these compounds are oligomers of phloroglucinol.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Replicase polyprotein 1abSevere acute respiratory syndrome-related coronavirusIC50 (µMol)77.05000.00402.92669.9600AID753301; AID753310
Replicase polyprotein 1abSevere acute respiratory syndrome-related coronavirusKi19.30000.00753.00839.1100AID753309
Beta-secretase 1Homo sapiens (human)IC50 (µMol)8.59000.00061.619410.0000AID483707
Beta-secretase 1Homo sapiens (human)Ki7.20000.00031.35248.0000AID483708
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
symbiont-mediated perturbation of host ubiquitin-like protein modificationReplicase polyprotein 1abSevere acute respiratory syndrome-related coronavirus
proteolysisBeta-secretase 1Homo sapiens (human)
membrane protein ectodomain proteolysisBeta-secretase 1Homo sapiens (human)
response to lead ionBeta-secretase 1Homo sapiens (human)
protein processingBeta-secretase 1Homo sapiens (human)
amyloid-beta formationBeta-secretase 1Homo sapiens (human)
amyloid precursor protein catabolic processBeta-secretase 1Homo sapiens (human)
positive regulation of neuron apoptotic processBeta-secretase 1Homo sapiens (human)
amyloid-beta metabolic processBeta-secretase 1Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painBeta-secretase 1Homo sapiens (human)
prepulse inhibitionBeta-secretase 1Homo sapiens (human)
cellular response to copper ionBeta-secretase 1Homo sapiens (human)
cellular response to manganese ionBeta-secretase 1Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionBeta-secretase 1Homo sapiens (human)
signaling receptor ligand precursor processingBeta-secretase 1Homo sapiens (human)
cellular response to amyloid-betaBeta-secretase 1Homo sapiens (human)
amyloid fibril formationBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
3'-5'-RNA exonuclease activityReplicase polyprotein 1abSevere acute respiratory syndrome-related coronavirus
RNA-dependent RNA polymerase activityReplicase polyprotein 1abSevere acute respiratory syndrome-related coronavirus
cysteine-type endopeptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome-related coronavirus
mRNA 5'-cap (guanine-N7-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome-related coronavirus
mRNA (nucleoside-2'-O-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome-related coronavirus
5'-3' RNA helicase activityReplicase polyprotein 1abSevere acute respiratory syndrome-related coronavirus
K63-linked deubiquitinase activityReplicase polyprotein 1abSevere acute respiratory syndrome-related coronavirus
K48-linked deubiquitinase activityReplicase polyprotein 1abSevere acute respiratory syndrome-related coronavirus
amyloid-beta bindingBeta-secretase 1Homo sapiens (human)
endopeptidase activityBeta-secretase 1Homo sapiens (human)
aspartic-type endopeptidase activityBeta-secretase 1Homo sapiens (human)
protein bindingBeta-secretase 1Homo sapiens (human)
peptidase activityBeta-secretase 1Homo sapiens (human)
beta-aspartyl-peptidase activityBeta-secretase 1Homo sapiens (human)
enzyme bindingBeta-secretase 1Homo sapiens (human)
protein serine/threonine kinase bindingBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (21)

Processvia Protein(s)Taxonomy
double membrane vesicle viral factory outer membraneReplicase polyprotein 1abSevere acute respiratory syndrome-related coronavirus
lysosomeBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
early endosomeBeta-secretase 1Homo sapiens (human)
late endosomeBeta-secretase 1Homo sapiens (human)
multivesicular bodyBeta-secretase 1Homo sapiens (human)
endoplasmic reticulum lumenBeta-secretase 1Homo sapiens (human)
Golgi apparatusBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
synaptic vesicleBeta-secretase 1Homo sapiens (human)
cell surfaceBeta-secretase 1Homo sapiens (human)
endosome membraneBeta-secretase 1Homo sapiens (human)
membraneBeta-secretase 1Homo sapiens (human)
axonBeta-secretase 1Homo sapiens (human)
dendriteBeta-secretase 1Homo sapiens (human)
neuronal cell bodyBeta-secretase 1Homo sapiens (human)
membrane raftBeta-secretase 1Homo sapiens (human)
recycling endosomeBeta-secretase 1Homo sapiens (human)
Golgi-associated vesicle lumenBeta-secretase 1Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID483708Noncompetitive inhibition of human recombinant BACE1 after 60 mins by Dixon plot analysis2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Molecular docking studies of phlorotannins from Eisenia bicyclis with BACE1 inhibitory activity.
AID393271Antioxidant activity assessed as DPPH radical scavenging activity2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID393276Cytotoxicity against human HL60 cells at 100 uM after 24 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID393272Antioxidant activity assessed as superoxide radical scavenging activity2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID393278Antioxidant activity against mouse RAW264.7 cells assessed as reduction of ROS production after 200 mins measured by fluorescent dichlorofluorescein using DCFH-DA substrate2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID483707Inhibition of human recombinant BACE1 after 60 mins by FRET assay2010Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11
Molecular docking studies of phlorotannins from Eisenia bicyclis with BACE1 inhibitory activity.
AID753298Competitive inhibition of C-terminal His6-tagged recombinant SARS coronavirus 3C-like protease trans-cleavage activity expressed in Escherichia coli BL21 (DE3) using Dabcyl-KTSAVLQSGFRKME as substrate after 60 mins by Lineweaver-Burk plot analysis2013Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13
Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID753310Inhibition of C-terminal His6-tagged recombinant SARS coronavirus 3C-like protease trans-cleavage activity expressed in Escherichia coli BL21 (DE3) using Dabcyl-KTSAVLQSGFRKME as substrate after 60 mins by FRET assay2013Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13
Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID753309Competitive inhibition of C-terminal His6-tagged recombinant SARS coronavirus 3C-like protease trans-cleavage activity expressed in Escherichia coli BL21 (DE3) using Dabcyl-KTSAVLQSGFRKME as substrate after 60 mins by Dixon plot analysis2013Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13
Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID393270Antioxidant activity assessed as Fenton system generated hydroxyl radical scavenging activity by ESR spectrometer2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID1704263Inhibition of SARS-CoV-2 3c-like protease2020European journal of medicinal chemistry, Nov-15, Volume: 206The development of Coronavirus 3C-Like protease (3CL
AID753301Inhibition of SARS coronavirus 3C-like protease cis-cleavage activity transfected in african green monkey Vero cells using SAVLQSGFRK as substrate after 5 hrs by luciferase reporter gene assay2013Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13
Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID393275Cytotoxicity against mouse RAW264.7 cells at 100 uM after 24 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID753302Cytotoxicity against african green monkey Vero cells assessed as cell death by MTT assay2013Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13
Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID753304Selectivity index, ratio of CC50 for african green monkey Vero cells to IC50 for SARS coronavirus 3C-like protease cis-cleavage activity transfected in african green monkey Vero cells2013Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13
Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID393282Inhibition of Fe(2+)/H2O2-generated hydroxyl radical induced membrane protein oxidation in mouse RAW264.7 cells at 1 uM to 50 uM relative to control2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID393274Cytotoxicity against human MRC5 cells at 100 uM after 24 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID393273Antioxidant activity assessed as APPH generated peroxyl radical scavenging formation by ESR spectrometer2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID393277Antioxidant activity against mouse RAW264.7 cells assessed as reduction of ROS production measured by fluorescent dichlorofluorescein using DCFH-DA substrate2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (22.22)29.6817
2010's5 (55.56)24.3611
2020's2 (22.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.42

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 Index12.42 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.72 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (11.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]