Page last updated: 2024-11-12

cannabidiol hydroxyquinone

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

Description

cannabidiol hydroxyquinone: structure given in first source; an air oxidation product of cannabidiol; inhibits the hepatic microsomal drug-metabolizing enzymes of mice through the decrease of cytochrome P-450 content; RN given refers to (1R-trans)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11393311
CHEMBL ID4635276
CHEBI ID197014
SCHEMBL ID13609377
MeSH IDM0199219

Synonyms (28)

Synonym
cbdhq
hu 331
hu331
cannabidiol hydroxyquinone
hu-331
137252-25-6
3-hydroxy-2-[(1r,6r)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylcyclohexa-2,5-diene-1,4-dione
CHEBI:197014
2,5-cyclohexadiene-1,4-dione, 3-hydroxy-2-(3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-, (1r-trans)-
i7q196l4au ,
unii-i7q196l4au
CCG-208732
2,5-cyclohexadiene-1,4-dione, 3-hydroxy-2-((1r,6r)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-
SCHEMBL13609377
HMS3649F22
AKOS030241459
J-006987
Q3825917
DTXSID10929758
vce 004
SR-01000946715-1
sr-01000946715
cannabidiol hydroxyquinone (cbdhq)
bdbm50541572
CHEMBL4635276 ,
FS-7319
cannabidiol hydroxyquinone (cbdhq) 100 microg/ml in acetonitrile
cannabidiol hydroxyquinone (cbdhq) 1000 microg/ml in acetonitrile

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" A comparative in vivo study in mice has shown HU-331 to be less toxic and more effective than the commonly used doxorubicin."( HU-331: a cannabinoid quinone, with uncommon cytotoxic properties and low toxicity.
Kogan, NM; Peters, M, 2007
)
0.34

Compound-Compound Interactions

ExcerptReferenceRelevance
"Topoisomerase II (Topo2) inhibitors in combination with cisplatin represent a common treatment modality used for glioma patients."( Comparison of the effect of three different topoisomerase II inhibitors combined with cisplatin in human glioblastoma cells sensitized with double strand break repair inhibitors.
Galita, G; Kopa, P; Macieja, A; Majsterek, I; Pastwa, E; Poplawski, T, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
prenylquinoneA quinone substituted by a polyprenyl-derived side-chain. Prenylquinones occur in all living cells. Due to their amphiphilic character, they are mainly located in biological membranes where they function as electron and proton carriers in the photosynthetic and respiratory electron transport chains. Some prenylquinones also perform more specialised roles sucy as antioxidants and enzyme cofactors. Prenylquinones are classified according to ring structure: the main classes are menaquinones, phylloquinones, ubiquinones and plastoquinones.
[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)
Peroxisome proliferator-activated receptor gammaHomo sapiens (human)EC50 (µMol)10.50000.00000.992210.0000AID1657599
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (73)

Processvia Protein(s)Taxonomy
negative regulation of gene expressionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of cholesterol effluxPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
long-chain fatty acid transportPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of osteoblast differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of smooth muscle cell proliferationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of receptor signaling pathway via STATPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of low-density lipoprotein receptor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of signaling receptor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of gene expressionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of BMP signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of MAP kinase activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of adiponectin secretionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of miRNA transcriptionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of cardiac muscle hypertrophy in response to stressPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of connective tissue replacement involved in inflammatory response wound healingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
placenta developmentPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
regulation of transcription by RNA polymerase IIPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
lipid metabolic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
signal transductionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
G protein-coupled receptor signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
response to nutrientPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
regulation of blood pressurePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of gene expressionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of gene expressionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
macrophage derived foam cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of macrophage derived foam cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of cholesterol storagePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of lipid storagePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of sequestering of triglyceridePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of angiogenesisPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
monocyte differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
BMP signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
epithelial cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cellular response to insulin stimulusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
response to lipidPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
peroxisome proliferator activated receptor signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
glucose homeostasisPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
regulation of circadian rhythmPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
mRNA transcription by RNA polymerase IIPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
lipoprotein transportPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of blood vessel endothelial cell migrationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
innate immune responsePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cell fate commitmentPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of fat cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of DNA-templated transcriptionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of DNA-templated transcriptionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
retinoic acid receptor signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cell maturationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
rhythmic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
white fat cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
lipid homeostasisPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of type II interferon-mediated signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of SMAD protein signal transductionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
regulation of cholesterol transporter activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cellular response to low-density lipoprotein particle stimulusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cellular response to hypoxiaPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of mitochondrial fissionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
regulation of cellular response to insulin stimulusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of extracellular matrix assemblyPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of miRNA transcriptionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of miRNA transcriptionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of cellular response to transforming growth factor beta stimulusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of adipose tissue developmentPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of vascular associated smooth muscle cell proliferationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of vascular associated smooth muscle cell apoptotic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of vascular endothelial cell proliferationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of fatty acid metabolic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
fatty acid metabolic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of inflammatory responsePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
hormone-mediated signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (28)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
transcription coregulator bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
nucleic acid bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
chromatin bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
double-stranded DNA bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA-binding transcription factor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
nuclear receptor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
prostaglandin receptor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
protein bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
zinc ion bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
enzyme bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
peptide bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
identical protein bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
sequence-specific DNA bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
nuclear retinoid X receptor bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
arachidonic acid bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA binding domain bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
LBD domain bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
alpha-actinin bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
R-SMAD bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
E-box bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
STAT family protein bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA-binding transcription factor bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
nucleusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
nucleusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
nucleoplasmPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cytosolPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
intracellular membrane-bounded organellePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
RNA polymerase II transcription regulator complexPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
chromatinPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
receptor complexPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1657599Agonist activity at GAL4-tagged PPARgamma (unknown origin) transiently expressed in HEK293T cells co-transfected with GAL4-tagged luc incubated for 6 hrs by dual luciferase reporter gene assay2020Journal of natural products, 05-22, Volume: 83, Issue:5
The Oxidation of Phytocannabinoids to Cannabinoquinoids.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (6.67)18.2507
2000's5 (33.33)29.6817
2010's6 (40.00)24.3611
2020's3 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.71

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

MetricThis Compound (vs All)
Research Demand Index21.71 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index5.18 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.71)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (13.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (86.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]