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cannabidiol hydroxyquinone

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 [MeSH]

HU-331 : no description available [CHeBI]

Cross-References

ID SourceID
PubMed CID11393311
CHEMBL ID4635276
SCHEMBL ID13609377
CHEBI ID197014
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

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.

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Peroxisome proliferator-activated receptor gammaHomo sapiens (human)EC5010.5000AID1657599

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
ISSN: 1520-6025
The Oxidation of Phytocannabinoids to Cannabinoquinoids.

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

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%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
illimaquinonemonohydroxy-1,4-benzoquinones;
prenylquinone
metabolite00low000000
5-demethoxyubiquinone-9prenylquinone00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
cannabinoldibenzopyran202020204.0low000010
cannabichromene1-benzopyran202020204.0low000010
rosiglitazoneaminopyridine;
thiazolidinediones
EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor;
ferroptosis inhibitor;
insulin-sensitizing drug
202020204.0low000010
cannabidiololefinic compound;
phytocannabinoid;
resorcinols
antimicrobial agent;
plant metabolite
202020204.0low000010
cannabigerolphytocannabinoid;
resorcinols
anti-inflammatory agent;
antibacterial agent;
antioxidant;
appetite enhancer;
cannabinoid receptor agonist;
neuroprotective agent;
plant metabolite
202020204.0low000010
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
quinone1,4-benzoquinonescofactor;
human xenobiotic metabolite;
mouse metabolite
2006201314.5low000110
malondialdehydedialdehydebiomarker2007200717.0low000100
etoposidebeta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound
antineoplastic agent;
DNA synthesis inhibitor
201920195.0low000010
cannabielsoin202220222.0medium000001
cannabidiololefinic compound;
phytocannabinoid;
resorcinols
antimicrobial agent;
plant metabolite
1991202212.6high001652
nu 7441dibenzothiophenes201920195.0low000010
nk314201920195.0medium000010
phenanthrenes201920195.0low000010
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Akinetic-Rigid Variant of Huntington Disease0201720177.0low000010
Angiogenesis, Pathologic02006200618.0low000100
Astrocytoma, Grade IV0201920195.0low000010
Benign Neoplasms02007200717.0low000100
Benign Neoplasms, Brain0201920195.0low000010
Body Weight02007200717.0low000100
Brain Neoplasms0201920195.0low000010
Experimental Neoplasms0202120213.0low000001
Glioblastoma0201920195.0low000010
Huntington Disease0201720177.0low000010
Neoplasms02007200717.0low000100

Safety/Toxicity (1)

ArticleYear
HU-331: a cannabinoid quinone, with uncommon cytotoxic properties and low toxicity.
Expert opinion on investigational drugs, , Volume: 16, Issue:9
2007

Interactions (1)

ArticleYear
Comparison of the effect of three different topoisomerase II inhibitors combined with cisplatin in human glioblastoma cells sensitized with double strand break repair inhibitors.
Molecular biology reports, , Volume: 46, Issue:4
2019