Page last updated: 2024-12-08

6,6'-bieckol

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

Description

6,6'-bieckol: structure given in first source; antiplasmin antag [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

6,6'-bieckol : A phlorotanin that is 1,1'-bioxanthrene substituted by 3,5-dihydroxyphenoxy groups at position 6 and 6' and hydroxy groups at positions 2, 2', 4, 4', 7, 7', 9 and 9' respectively. It is isolated from an edible marine brown alga Ecklonia cava and 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 CID137388
CHEMBL ID502202
CHEBI ID65496
SCHEMBL ID1353030
MeSH IDM0172656

Synonyms (17)

Synonym
(1,1'-bidibenzo(b,e)(1,4)dioxin)-2,2',4,4',7,7',9,9'-octol, 6,6'-bis(3,5-dihydroxyphenoxy)-
unii-87u82w6ifi
88095-81-2
87u82w6ifi ,
6,6'-bieckol
4-(3,5-dihydroxyphenoxy)-9-[6-(3,5-dihydroxyphenoxy)-2,4,7,9-tetrahydroxy-dibenzo-p-dioxin-1-yl]dibenzo-p-dioxin-1,3,6,8-tetrol
CHEMBL502202 ,
chebi:65496 ,
6,6'-bis(3,5-dihydroxyphenoxy)-(1,1'-bidibenzo[b,e][1,4]dioxin)-2,2',4,4',7,7',9,9'-octol
6,6'-bis(3,5-dihydroxyphenoxy)-1,1'-bioxanthrene-2,2',4,4',7,7',9,9'-octol
4-(3,5-dihydroxyphenoxy)-9-[6-(3,5-dihydroxyphenoxy)-2,4,7,9-tetrahydroxyoxanthren-1-yl]oxanthrene-1,3,6,8-tetrol
SCHEMBL1353030
DTXSID50236812
bdbm50479418
6,6''''-bieckol
Q4641520
6,6-bieckol
[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.
radical scavengerA role played by a substance that can react readily with, and thereby eliminate, radicals.
anti-HIV-1 agentAn anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
[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 (3)

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.
oxacycleAny 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 Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1EC50 (µMol)1.07000.00040.61539.7000AID363916
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (37)

Assay IDTitleYearJournalArticle
AID364086Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of p24 antigen production at 10 uM by ELISA2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID363928Inhibition of HIV1 3B recombinant protease2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from 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.
AID363916Inhibition of HIV1 3B reverse transcriptase activity2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from 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.
AID363929Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of p55 gag protein production after 4 days by Western blot analysis2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID363926Antiviral activity against HIV1 3B in human C8166 co-cultivated with H9 cells assessed as inhibition of cell-virus fusion after 72 hrs2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID393285Inhibition of MPO activity in TNF-alpha-stimulated human HL60 cells measured enzyme activity per 10'6 cells at 10 uM by spectrophotometrically2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID363918Antiviral activity against HIV1 3B in human C8166 cells assessed as inhibition of viral-induced syncytia formation after 72 hrs2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID363924Inhibition of HIV1 3B reverse transcriptase activity at 10 uM2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID363923Inhibition of HIV1 3B reverse transcriptase activity at 1 uM2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID393281Antioxidant activity against mouse RAW264.7 cells assessed as reduction of ROS production at 50 uM after 210 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.
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.
AID364083Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of p24 gag protein production after 4 days by Western blot analysis2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID363925Antiviral activity against HIV1 3B in human C8166 co-cultivated with H9 cells assessed as inhibition of cell-cell fusion after 72 hrs2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID364085Cytotoxicity against human CEM-SS cells up to 500 by MTT assay2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from 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.
AID363930Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of p41 gag protein production after 4 days by Western blot analysis2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID363922Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of p24 antigen production by ELISA2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID363919Antiviral activity against HIV1 3B in human C8166 cells assessed as inhibition of viral-induced syncytia formation at 25 uM after 72 hrs2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from 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.
AID393284Inhibition of MPO activity in TNF-alpha-stimulated human HL60 cells measured enzyme activity per 10'6 cells by spectrophotometrically2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava.
AID364084Therapeutic index, ratio of CC50 for human CEM-SS cells to IC50 for HIV1 induced lytic effect2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID393283Increase in intracellular GSH level in mouse RAW264.7 cells assessed as monobromobimane-GSH fluorescence intensity at 20 uM after 120 mins2009Bioorganic & 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.
AID364087Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of p24 antigen production at 25 uM by ELISA2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID363917Cytotoxicity against human CEM-SS cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from 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.
AID363927Antiviral activity against HIV13B in human C8166 co-cultivated with H9 cells assessed as inhibition of viral-induced syncytia formation at 25 uM after 72 hrs2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID363920Antiviral activity against HIV1 3B in human CEM-SS cells assessed as inhibition of viral-induced lytic effect after 7 days by MTT assay2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from 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.
AID363921Antiviral activity against HIV1 3B in human CEM-SS cells assessed as inhibition of viral-induced lytic effect at 25 uM after 7 days by MTT assay2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Anti-HIV-1 activity of phloroglucinol derivative, 6,6'-bieckol, from Ecklonia cava.
AID393279Antioxidant activity against mouse RAW264.7 cells assessed as reduction of ROS production at 1 uM 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.
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.
AID393280Antioxidant activity against mouse RAW264.7 cells assessed as reduction of ROS production at 50 uM 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.
AID393286Inhibition of MPO activity in TNF-alpha-stimulated human HL60 cells measured enzyme activity per 10'6 cells at 50 uM by spectrophotometrically2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Chemical components and its antioxidant properties in vitro: an edible marine brown alga, 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.88)18.7374
1990's0 (0.00)18.2507
2000's4 (23.53)29.6817
2010's11 (64.71)24.3611
2020's1 (5.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.73

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 Index11.73 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.73)

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%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]