Page last updated: 2024-11-13

antroquinonol d

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

Description

antroquinonol: isolated from Antrodia camphorata [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

antroquinonol : An enone that is cyclohex-2-en-1-one substituted by a hydroxy group at position 4, methoxy groups at positions 2 and 3, a methyl group at position 6 and a (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl group at position 5 (the 4R,5R,6R stereoisomer). It is isolated from the solid-state fermented mycelium of the fungus Antrodia camphorata and has been found to exhibit potent cytotoxicity against a number of human cancer cell lines. However, a synthesis-enabled biological re-examination published in 2016, revealed minimal in vitro and in vivo antitumour activity in preclinical models. [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 CID24875259
CHEMBL ID3235620
CHEBI ID65415
SCHEMBL ID16919581
MeSH IDM000607680

Synonyms (27)

Synonym
antroquinonol
(+)-antroquinonol a
antroquinonol d
antroquinonol a
(4r,5r,6r)-4-hydroxy-2,3-dimethoxy-6-methyl-5-[(2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]cyclohex-2-en-1-one
CHEBI:65415 ,
j3.387.174k
hocena
CHEMBL3235620
(4r)-2,3-dimethoxy-4.alpha.-hydroxy-5.alpha.-((2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrienyl)-6.beta.-methyl-2-cyclohexene-1-one
antroquinonol [who-dd]
2-cyclohexen-1-one, 4-hydroxy-2,3-dimethoxy-6-methyl-5-((2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)-, (4r,5r,6r)-
AX9P92T7JZ ,
(+)-antroquinonol
1010081-09-0
unii-ax9p92t7jz
(4r)-2,3-dimethoxy-4alpha-hydroxy-5alpha-((2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrienyl)-6beta-methyl-2-cyclohexene-1-one
SCHEMBL16919581
LJTSIMVOOOLKOL-FNRDIUJOSA-N
DB12326
Q27133859
(4r,5r,6r)-4-hydroxy-2,3-dimethoxy-6-methyl-5-((2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)cyclohex-2-enone
(4r,5r,6r)-4-hydroxy-2,3-dimethoxy-6-methyl-5-((2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)cyclohex-2-en-1-one
(4r,5r,6r)-4-hydroxy-2,3-dimethoxy-6-methyl-5-[(2e,6e)-3,7,11-trimethyldodeca-2,6,10-trienyl]cyclohex-2-en-1-one
CS-0016956
HY-19893
AKOS040750532
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
fungal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
[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
enoneAn alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
enol etherEthers ROR' where R has a double bond adjacent to the oxygen of the ether linkage.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Protein farnesyltransferase subunit betaRattus norvegicus (Norway rat)IC50 (µMol)2.98600.00190.65072.9860AID1415844
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaRattus norvegicus (Norway rat)IC50 (µMol)2.98600.00190.54512.9860AID1415844
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1129217Drug excretion in Wistar rat urine assessed as (E)-6-((1R,2R,6R)-2-Hydroxy-3,4-dimethoxy-6-methyl-5-oxocyclo-hex-3-enyl)-4-methylhex-4-enoic acid level at 200 mg/kg, po administered via gavage measured after 24 hrs by HPLC-SPE-TT-NMR analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Metabolites of antroquinonol found in rat urine following oral administration.
AID1129219Drug excretion in Wistar rat urine assessed as (E)-6-((1R,2R6R)-2,5-Dihy droxy-4-methoxy-6-methyl-3-oxocyclo-hex-4-enyl)-4-methylhex-3-enoic acid level at 200 mg/kg, po administered via gavage measured after 24 hrs by HPLC-SPE-TT-NMR analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Metabolites of antroquinonol found in rat urine following oral administration.
AID1129218Drug excretion in Wistar rat urine assessed as (E)-6-((1R,2R,6R)-2-Hydroxy-3,4-dimethoxy-6-methyl-5-oxocyclo-hex-3-enyl)-4-methylhex-3-enoic acid level at 200 mg/kg, po administered via gavage measured after 24 hrs by HPLC-SPE-TT-NMR analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Metabolites of antroquinonol found in rat urine following oral administration.
AID1415844Inhibition of recombinant rat FTase alpha/beta expressed in Escherichia coli using NBD-FPP/GST-tagged H-Ras as substrate incubated for 2 hrs by SDS-PAGE method2017MedChemComm, May-01, Volume: 8, Issue:5
New tricks for human farnesyltransferase inhibitor: cancer and beyond.
AID1501978Growth inhibition of human A549 cells after 48 hrs by SRB assay2017Journal of natural products, 09-22, Volume: 80, Issue:9
Meroterpenoids from a Medicinal Fungus Antrodia cinnamomea.
AID1501979Growth inhibition of human PC3 cells after 48 hrs by SRB assay2017Journal of natural products, 09-22, Volume: 80, Issue:9
Meroterpenoids from a Medicinal Fungus Antrodia cinnamomea.
AID1129220Drug excretion in Wistar rat urine assessed as (E)-6-((1R,2R6R)-2,5-Dihy droxy-4-methoxy-6-methyl-3-oxocyclo-hex-4-enyl)-4-methylhex-4-enoic acid level at 200 mg/kg, po administered via gavage measured after 24 hrs by HPLC-SPE-TT-NMR analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Metabolites of antroquinonol found in rat urine following oral administration.
AID1415843Cytotoxicity against human A549 cells assessed as decrease in cell viability after 48 hrs by MTT assay2017MedChemComm, May-01, Volume: 8, Issue:5
New tricks for human farnesyltransferase inhibitor: cancer and beyond.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (41)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (2.44)29.6817
2010's32 (78.05)24.3611
2020's8 (19.51)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.43

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 Index12.43 (24.57)
Research Supply Index3.74 (2.92)
Research Growth Index6.16 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.43)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (4.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other39 (95.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]