Compounds > flavoglaucin
Page last updated: 2024-11-07

flavoglaucin

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

Description

Flavoglaucin is a yellow-greenish pigment produced by various fungal species, notably Aspergillus glaucus. It exhibits potent antimicrobial and antioxidant properties, making it a promising candidate for pharmaceutical and food applications. Research has focused on its synthesis, both natural and synthetic routes, to explore its potential as a therapeutic agent. Its antifungal activity against various pathogenic fungi, including Candida albicans and Aspergillus fumigatus, is particularly noteworthy. The compound has also demonstrated antiviral effects against influenza virus and herpes simplex virus. Its antioxidant properties are attributed to its ability to scavenge free radicals, contributing to its potential in protecting cells from oxidative damage. Flavoglaucin is studied extensively for its potential to treat infections and inflammatory conditions, as well as its potential applications in the food industry as a natural preservative and colorant.'

flavoglaucin: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID119037
CHEMBL ID1813664
CHEBI ID68188
MeSH IDM0046265

Synonyms (17)

Synonym
6-heptyl-3-(3-methyl-2-butenyl)gentisaldehyde
flavoglaucin
523-73-9
2-heptyl-3,6-dihydroxy-5-(3-methylbut-2-enyl)benzaldehyde
chebi:68188 ,
CHEMBL1813664
ccris 6491
benzaldehyde, 2-heptyl-3,6-dihydroxy-5-(3-methyl-2-butenyl)-
2-heptyl-3,6-dihydroxy-5-(3-methyl-2-butenyl)benzaldehyde
DTXSID60200327
ncgc00381406-01!2-heptyl-3,6-dihydroxy-5-(3-methylbut-2-enyl)benzaldehyde
Q27136682
BS-1106
AKOS040761739
2-heptyl-3,6-dihydroxy-5-(3-methyl-2-buten-1-yl)benzaldehyde
7TTH54XZQ5
benzaldehyde, 2-heptyl-3,6-dihydroxy-5-(3-methyl-2-buten-1-yl)-

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (1)

ClassDescription
hydroquinonesBenzenediols that have the hydroxy substituents in the 1- and 4-positions.
[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]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID1085776Antibacterial activity against Staphylococcus aureus ATCC 292132012Medicinal 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.
AID610910Displacement of [3H]nor-Binaltorphimine from human kappa opioid receptor expressed in CHO-K1 cells after 60 mins by scintillation counting2011Journal 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.
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.
AID610909Displacement of [3H]DPDPE from human delta opioid receptor expressed in CHO-K1 cells after 60 mins by scintillation counting2011Journal 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.
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.
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.
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.
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.
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.
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.
AID1085775Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 335912012Medicinal 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.
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.
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.
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.
AID610911Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO-K1 cells after 60 mins by scintillation counting2011Journal 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.
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.
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.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (25.00)18.7374
1990's1 (8.33)18.2507
2000's1 (8.33)29.6817
2010's5 (41.67)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.39

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 Index12.39 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.96 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.39)

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%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
benzaldehyde
[no description available]		2.110benzaldehydesEC 3.1.1.3 (triacylglycerol lipase) inhibitor;
EC 3.5.5.1 (nitrilase) inhibitor;
flavouring agent;
fragrance;
odorant receptor agonist;
plant metabolite
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		1.9610sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.0710aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
ciprofloxacin
Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.		2.0710aminoquinoline;
cyclopropanes;
fluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone;
zwitterion		antibacterial drug;
antiinfective agent;
antimicrobial agent;
DNA synthesis inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
environmental contaminant;
topoisomerase IV inhibitor;
xenobiotic
pentamidine
Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.		2.0710aromatic ether;
carboxamidine;
diether		anti-inflammatory agent;
antifungal agent;
calmodulin antagonist;
chemokine receptor 5 antagonist;
EC 2.3.1.48 (histone acetyltransferase) inhibitor;
NMDA receptor antagonist;
S100 calcium-binding protein B inhibitor;
trypanocidal drug;
xenobiotic
salicyl alcohol
salicyl alcohol: RN given refers to parent cpd; saligenin is the aglycone of salicin; structure; it is oxidatively metabolized to gentisic acid. salicyl alcohol : A hydroxybenzyl alcohol that is phenol substituted by a hydroxymethyl group at C-2.		7.2510aromatic primary alcohol;
hydroxybenzyl alcohol		human urinary metabolite
salicylaldehyde
o-hydroxybenzaldehyde: structure in first source		7.2510hydroxybenzaldehydenematicide;
plant metabolite
oleanolic acid
[no description available]		1.9810hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
azoxymethane
Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.		1.9810
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		1.9810D-glucopyranoseepitope;
mouse metabolite
cyclopenol
cyclopenol: RN given refers to cis-(-)-isomer		2.0810
cp-55,940
[no description available]		2.0610
echinuline
echinuline: tri-isoprenylated cyclic dipeptide from Aspergillus amstelodami; structure; Rn given refers to (3S-cis)-isomer. echinulin : An indole alkaloid with formula C29H39N3O2. It is a fungal metabolite found in several Aspergillus species.		2.77302,5-diketopiperazines;
indole alkaloid;
indoles;
olefinic compound		Aspergillus metabolite;
marine metabolite;
plant metabolite
gingerol
gingerol: an active ingredient in GINGER along with SHOGAOL. a nonvolatile methoxy phenyl decanone. gingerol : A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger.		1.9810beta-hydroxy ketone;
guaiacols		antineoplastic agent;
plant metabolite
shikonin
shikonin: a naphthazarin; has antineoplastic and angiogenesis inhibiting activities		1.9810hydroxy-1,4-naphthoquinone
naphthoquinones
Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.		1.9810
amphotericin b
Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.		2.0710antibiotic antifungal drug;
macrolide antibiotic;
polyene antibiotic		antiamoebic agent;
antiprotozoal drug;
bacterial metabolite
naloxone
Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.		2.0610morphinane alkaloid;
organic heteropentacyclic compound;
tertiary alcohol		antidote to opioid poisoning;
central nervous system depressant;
mu-opioid receptor antagonist
(E)-5-hydroxy-6-(3-methylbut-2-enyl)-2-(pent-1-enyl)benzofuran-4-carbaldehyde
[no description available]		2.47201-benzofurans;
aldehyde;
phenols		Aspergillus metabolite;
Chaetomium metabolite;
radical scavenger
peoniflorin
peoniflorin: from Radix and of Paeonia suffruticosa		1.9810
neoechinulin
neoechinulin: structure		2.0510
ConditionIndicatedRelationship StrengthStudiesTrials
Skin Aging
The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.		02.2510
Cancer of Skin
[description not available]		02.0510
Skin Neoplasms
Tumors or cancer of the SKIN.		02.0510
Cancer of Intestines
[description not available]		01.9810
Intestinal Neoplasms
Tumors or cancer of the INTESTINES.		01.9810