eckstolonol profile

eckstolonol: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

eckstolonol : A phlorotannin that is [1,4]benzodioxino[2,3-a]oxanthrene substituted by hydroxy groups at positions 1, 3, 6, 9 and 11. Isolated from the brown alga Ecklonia stolonifera, it exhibits radical scavenging 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]

ID Source	ID
PubMed CID	10429214
CHEMBL ID	559870
CHEBI ID	65820
SCHEMBL ID	14848420
MeSH ID	M0494616

Synonym
dioxinodehydroeckol
chebi:65820 ,
CHEMBL559870 ,
5,8,13,14-tetraoxa-pentaphene-1,3,6,9,11-pentaol
bdbm50319629
eckstolonol
5,8,13,14-tetraoxa-pentaphene-1,3,6,9,11-pentol
[1,4]benzodioxino[2,3-a]oxanthrene-1,3,6,9,11-pentol
SCHEMBL14848420
Q5332937
N5P71K0GE3 ,
benzo(1,2-b:3,4-b')bis(1,4)benzodioxin-1,3,6,9,11-pentol
unii-n5p71k0ge3
639514-05-9
DTXSID801030416

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
radical scavenger	A role played by a substance that can react readily with, and thereby eliminate, radicals.
[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]

Class	Description
phlorotannin	A 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.
organic heteropentacyclic compound
oxacycle	Any organic heterocyclic compound containing at least one ring oxygen atom.
[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	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus	IC50 (µMol)	152.4000	0.0040	2.9266	9.9600	AID753301; AID753310
Beta-secretase 1	Homo sapiens (human)	IC50 (µMol)	5.3500	0.0006	1.6194	10.0000	AID483707
Beta-secretase 1	Homo sapiens (human)	Ki	8.0000	0.0003	1.3524	8.0000	AID483708
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
symbiont-mediated perturbation of host ubiquitin-like protein modification	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
proteolysis	Beta-secretase 1	Homo sapiens (human)
membrane protein ectodomain proteolysis	Beta-secretase 1	Homo sapiens (human)
response to lead ion	Beta-secretase 1	Homo sapiens (human)
protein processing	Beta-secretase 1	Homo sapiens (human)
amyloid-beta formation	Beta-secretase 1	Homo sapiens (human)
amyloid precursor protein catabolic process	Beta-secretase 1	Homo sapiens (human)
positive regulation of neuron apoptotic process	Beta-secretase 1	Homo sapiens (human)
amyloid-beta metabolic process	Beta-secretase 1	Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of pain	Beta-secretase 1	Homo sapiens (human)
prepulse inhibition	Beta-secretase 1	Homo sapiens (human)
cellular response to copper ion	Beta-secretase 1	Homo sapiens (human)
cellular response to manganese ion	Beta-secretase 1	Homo sapiens (human)
presynaptic modulation of chemical synaptic transmission	Beta-secretase 1	Homo sapiens (human)
signaling receptor ligand precursor processing	Beta-secretase 1	Homo sapiens (human)
cellular response to amyloid-beta	Beta-secretase 1	Homo sapiens (human)
amyloid fibril formation	Beta-secretase 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

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

Process	via Protein(s)	Taxonomy
double membrane vesicle viral factory outer membrane	Replicase polyprotein 1ab	Severe acute respiratory syndrome-related coronavirus
lysosome	Beta-secretase 1	Homo sapiens (human)
endosome	Beta-secretase 1	Homo sapiens (human)
early endosome	Beta-secretase 1	Homo sapiens (human)
late endosome	Beta-secretase 1	Homo sapiens (human)
multivesicular body	Beta-secretase 1	Homo sapiens (human)
endoplasmic reticulum lumen	Beta-secretase 1	Homo sapiens (human)
Golgi apparatus	Beta-secretase 1	Homo sapiens (human)
trans-Golgi network	Beta-secretase 1	Homo sapiens (human)
plasma membrane	Beta-secretase 1	Homo sapiens (human)
synaptic vesicle	Beta-secretase 1	Homo sapiens (human)
cell surface	Beta-secretase 1	Homo sapiens (human)
endosome membrane	Beta-secretase 1	Homo sapiens (human)
membrane	Beta-secretase 1	Homo sapiens (human)
axon	Beta-secretase 1	Homo sapiens (human)
dendrite	Beta-secretase 1	Homo sapiens (human)
neuronal cell body	Beta-secretase 1	Homo sapiens (human)
membrane raft	Beta-secretase 1	Homo sapiens (human)
recycling endosome	Beta-secretase 1	Homo sapiens (human)
Golgi-associated vesicle lumen	Beta-secretase 1	Homo sapiens (human)
hippocampal mossy fiber to CA3 synapse	Beta-secretase 1	Homo sapiens (human)
endosome	Beta-secretase 1	Homo sapiens (human)
plasma membrane	Beta-secretase 1	Homo sapiens (human)
trans-Golgi network	Beta-secretase 1	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay ID	Title	Year	Journal	Article
AID753310	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 FRET assay	2013	Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13	Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID427081	Inhibition of Fc-epsilonR1-mediated histamine release in anti-human Fc-epsilonR1 antibody-stimulated human KU-812F cells by spectrofluorimetry	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on Fc(epsilon)RI expression.
AID427076	Inhibition of Fc-epsilonR1 expression in anti-human Fc-epsilonR1 antibody-stimulated human KU-812F cells at 10 uM after 24 hrs by flow cytometry	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on Fc(epsilon)RI expression.
AID753304	Selectivity 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 cells	2013	Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13	Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID427079	Inhibition of Fc-epsilonR1 alpha mRNA expression in anti-human Fc-epsilonR1 antibody-stimulated human KU-812F cells after 24 hrs by RT-PCR	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on Fc(epsilon)RI expression.
AID753301	Inhibition 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 assay	2013	Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13	Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID753309	Competitive 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 analysis	2013	Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13	Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID753302	Cytotoxicity against african green monkey Vero cells assessed as cell death by MTT assay	2013	Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13	Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
AID483707	Inhibition of human recombinant BACE1 after 60 mins by FRET assay	2010	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11	Molecular docking studies of phlorotannins from Eisenia bicyclis with BACE1 inhibitory activity.
AID427077	Inhibition of Fc-epsilonR1 expression in anti-human Fc-epsilonR1 antibody-stimulated human KU-812F cells at 25 uM after 24 hrs by flow cytometry	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on Fc(epsilon)RI expression.
AID427080	Inhibition of Fc-epsilonR1-mediated [Ca2+]i elevation in anti-human Fc-epsilonR1 antibody-stimulated human KU-812F cells	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on Fc(epsilon)RI expression.
AID483708	Noncompetitive inhibition of human recombinant BACE1 after 60 mins by Dixon plot analysis	2010	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 20, Issue:11	Molecular docking studies of phlorotannins from Eisenia bicyclis with BACE1 inhibitory activity.
AID427078	Inhibition of Fc-epsilonR1 protein expression in anti-human Fc-epsilonR1 antibody-stimulated human KU-812F cells after 24 hrs by Western blotting	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on Fc(epsilon)RI expression.
AID427074	Inhibition of Fc-epsilonR1 expression in anti-human Fc-epsilonR1 antibody-stimulated human KU-812F cells at 50 uM after 24 hrs by flow cytometry	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on Fc(epsilon)RI expression.
AID427082	Cytotoxicity against human KU-812F cells assessed as reduction in cell viability at 1 to 50 uM after 24 hrs by MTS assay	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on Fc(epsilon)RI expression.
AID427075	Inhibition of Fc-epsilonR1 expression in anti-human Fc-epsilonR1 antibody-stimulated human KU-812F cells at 5 uM after 24 hrs by flow cytometry	2009	Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13	Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on Fc(epsilon)RI expression.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	3 (17.65)	29.6817
2010's	14 (82.35)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	17 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
phloroglucinol Phloroglucinol: A trinitrobenzene derivative with antispasmodic properties that is used primarily as a laboratory reagent.. phloroglucinol : A benzenetriol with hydroxy groups at position 1, 3 and 5.	3.45	7	benzenetriol; phenolic donor	algal metabolite
tacrine Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.	2.02	1	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2.1	1	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
flumazenil Flumazenil: A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.. flumazenil : An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.	2.1	1	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
aloe emodin aloe emodin: structure distinct from emodin; this does not mean emodin from aloe. Aloe emodin : A dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe.	2.08	1	aromatic primary alcohol; dihydroxyanthraquinone	antineoplastic agent; plant metabolite
hesperetin [no description available]	2.08	1	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
phlorofucofuroeckol a phlorofucofuroeckol A: phlorotannin from Ecklonia kurome; structure given in first source	3.32	6
eckol eckol: structure given in first source; isolated from brown alga Ecklonia kurome Okamura; inhibitor of alpha 2-antiplasmin. eckol : A phlorotannin that is oxanthrene-1,3,6,8-tetrol substituted by a 3,5-dihydroxyphenoxy moiety at position 4. Isolated from the marine brown alga, Ecklonia cava, it exhibits antioxidant activity.	3.19	5	phlorotannin	antioxidant; metabolite
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.17	5
dieckol dieckol: found in brown Eisenia and Ecklonia algae, have several pharmacologically beneficial effects such as anti-inflammation; structure in first source. dieckol : A phlorotannin isolated from a brown alga Ecklonia cava which exhibits antioxidant, hepatoprotective and anticoagulant activities.	3.19	5	aromatic ether; oxacycle; phlorotannin	anticoagulant; EC 3.2.1.20 (alpha-glucosidase) inhibitor; hepatoprotective agent; metabolite; radical scavenger
quercetin [no description available]	2.05	1	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
daidzein [no description available]	2.08	1	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite
7-phloroeckol 7-phloroeckol: isolated from Ecklonia cava; structure in first source. 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.	2.98	4	aromatic ether; phlorotannin	antioxidant; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; metabolite
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	3.16	5
silybin Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.	2.02	1

Condition	Relationship Strength	Studies
Respiratory Syndrome, Acute, Severe [description not available]	2.08	1
Severe Acute Respiratory Syndrome A viral disorder characterized by high FEVER, dry COUGH, shortness of breath (DYSPNEA) or breathing difficulties, and atypical PNEUMONIA. A virus in the genus CORONAVIRUS is the suspected agent.	2.08	1
Protein Aggregation, Pathological A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.	2.21	1
Age-Related Osteoporosis [description not available]	2.13	1
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	2.13	1
B16 Melanoma [description not available]	2.05	1
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.06	1
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	2.06	1
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.06	1

eckstolonol

Description

Cross-References

Synonyms (15)

Roles (2)

Drug Classes (3)

Protein Targets (2)

Inhibition Measurements

Biological Processes (17)

Molecular Functions (16)

Ceullar Components (21)

Bioassays (16)

Research

Studies (17)

Market Indicators

Research Demand Index: 11.92

Study Types

eckstolonol

Description

Cross-References

Synonyms (15)

Roles (2)

Drug Classes (3)

Protein Targets (2)

Inhibition Measurements

Biological Processes (17)

Molecular Functions (16)

Ceullar Components (21)

Bioassays (16)

Research

Studies (17)

Market Indicators

Research Demand Index: 11.92

Study Types

Related Drugs (15)

Related Conditions (9)