Compounds > 9-hydroxycanthin-6-one
Page last updated: 2024-11-12

9-hydroxycanthin-6-one

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Description

9-hydroxycanthin-6-one: from Eurycoma longifolia Jack (Simaroubaceae), induces penile erection and delays ejaculation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

9-hydroxycanthin-6-one : An indole alkaloid that is canthin-6-one substituted by a hydroxy group at position 9. Isolated from the roots of Eurycoma longifolia, it exhibits antineoplastic 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]

FloraRankFlora DefinitionFamilyFamily Definition
EurycomagenusA plant genus of the family SIMAROUBACEAE. Members contain quassinoids. There is Malaysian folk use of these plants for male virility.[MeSH]SimaroubaceaeA plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida. Leaves are alternate and compound. Most have small flowers, bitter bark, and fleshy fruits that are sometimes winged. Members contain QUASSINS.[MeSH]
Eurycoma longifoliaspecies[no description available]SimaroubaceaeA plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida. Leaves are alternate and compound. Most have small flowers, bitter bark, and fleshy fruits that are sometimes winged. Members contain QUASSINS.[MeSH]

Cross-References

ID SourceID
PubMed CID10263500
CHEMBL ID444160
CHEBI ID66041
MeSH IDM0576236

Synonyms (14)

Synonym
chebi:66041 ,
CHEMBL444160 ,
9-hydroxycanthin-6-one
9-hydroxy-6h-indolo[3,2,1-de][1,5]naphthyridin-6-one
bdbm50090907
138544-91-9
Q27134546
1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione
13-hydroxy-1,6-diazatetracyclo[7.6.1.0?,??.0??,??]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one
DTXSID601220900
AKOS040761293
FS-7527
HY-N7183
CS-0103815
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glycogen synthase kinase-3 betaHomo sapiens (human)IC50 (µMol)6.80000.00060.801310.0000AID1228418
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (73)

Processvia Protein(s)Taxonomy
positive regulation of gene expressionGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of gene expressionGlycogen synthase kinase-3 betaHomo sapiens (human)
ER overload responseGlycogen synthase kinase-3 betaHomo sapiens (human)
peptidyl-serine phosphorylationGlycogen synthase kinase-3 betaHomo sapiens (human)
intracellular signal transductionGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of apoptotic processGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein export from nucleusGlycogen synthase kinase-3 betaHomo sapiens (human)
epithelial to mesenchymal transitionGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of cell-matrix adhesionGlycogen synthase kinase-3 betaHomo sapiens (human)
glycogen metabolic processGlycogen synthase kinase-3 betaHomo sapiens (human)
protein phosphorylationGlycogen synthase kinase-3 betaHomo sapiens (human)
mitochondrion organizationGlycogen synthase kinase-3 betaHomo sapiens (human)
dopamine receptor signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
circadian rhythmGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of autophagyGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of gene expressionGlycogen synthase kinase-3 betaHomo sapiens (human)
peptidyl-serine phosphorylationGlycogen synthase kinase-3 betaHomo sapiens (human)
peptidyl-threonine phosphorylationGlycogen synthase kinase-3 betaHomo sapiens (human)
viral protein processingGlycogen synthase kinase-3 betaHomo sapiens (human)
hippocampus developmentGlycogen synthase kinase-3 betaHomo sapiens (human)
establishment of cell polarityGlycogen synthase kinase-3 betaHomo sapiens (human)
maintenance of cell polarityGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of cell migrationGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of axon extensionGlycogen synthase kinase-3 betaHomo sapiens (human)
neuron projection developmentGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of protein-containing complex assemblyGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein-containing complex assemblyGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein ubiquitinationGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of proteasomal ubiquitin-dependent protein catabolic processGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of phosphoprotein phosphatase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of microtubule-based processGlycogen synthase kinase-3 betaHomo sapiens (human)
intracellular signal transductionGlycogen synthase kinase-3 betaHomo sapiens (human)
cellular response to interleukin-3Glycogen synthase kinase-3 betaHomo sapiens (human)
regulation of circadian rhythmGlycogen synthase kinase-3 betaHomo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic processGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of GTPase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of cell differentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of osteoblast differentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of glycogen biosynthetic processGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of cilium assemblyGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein catabolic processGlycogen synthase kinase-3 betaHomo sapiens (human)
protein autophosphorylationGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of protein export from nucleusGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of dendrite morphogenesisGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of axonogenesisGlycogen synthase kinase-3 betaHomo sapiens (human)
canonical Wnt signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
excitatory postsynaptic potentialGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of microtubule cytoskeleton organizationGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of calcineurin-NFAT signaling cascadeGlycogen synthase kinase-3 betaHomo sapiens (human)
superior temporal gyrus developmentGlycogen synthase kinase-3 betaHomo sapiens (human)
cellular response to retinoic acidGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of canonical Wnt signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
extrinsic apoptotic signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
extrinsic apoptotic signaling pathway in absence of ligandGlycogen synthase kinase-3 betaHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionGlycogen synthase kinase-3 betaHomo sapiens (human)
neuron projection organizationGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of microtubule anchoring at centrosomeGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of cellular response to heatGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of protein localization to nucleusGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of long-term synaptic potentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of mitochondrial outer membrane permeabilization involved in apoptotic signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of protein acetylationGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathway via death domain receptorsGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein localization to ciliumGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of dopaminergic neuron differentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
cellular response to amyloid-betaGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein localization to centrosomeGlycogen synthase kinase-3 betaHomo sapiens (human)
beta-catenin destruction complex disassemblyGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of type B pancreatic cell developmentGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of glycogen (starch) synthase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of mesenchymal stem cell differentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of TOR signalingGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of neuron projection developmentGlycogen synthase kinase-3 betaHomo sapiens (human)
cell differentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
insulin receptor signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
protease bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
p53 bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
protein kinase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
protein serine/threonine kinase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
protein bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
ATP bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
beta-catenin bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
kinase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
protein kinase bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
ubiquitin protein ligase bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
protein kinase A catalytic subunit bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
dynactin bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
tau protein bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
tau-protein kinase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
NF-kappaB bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
protein serine kinase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
glutamatergic synapseGlycogen synthase kinase-3 betaHomo sapiens (human)
nucleusGlycogen synthase kinase-3 betaHomo sapiens (human)
nucleoplasmGlycogen synthase kinase-3 betaHomo sapiens (human)
cytoplasmGlycogen synthase kinase-3 betaHomo sapiens (human)
mitochondrionGlycogen synthase kinase-3 betaHomo sapiens (human)
centrosomeGlycogen synthase kinase-3 betaHomo sapiens (human)
cytosolGlycogen synthase kinase-3 betaHomo sapiens (human)
plasma membraneGlycogen synthase kinase-3 betaHomo sapiens (human)
axonGlycogen synthase kinase-3 betaHomo sapiens (human)
dendriteGlycogen synthase kinase-3 betaHomo sapiens (human)
beta-catenin destruction complexGlycogen synthase kinase-3 betaHomo sapiens (human)
presynapseGlycogen synthase kinase-3 betaHomo sapiens (human)
postsynapseGlycogen synthase kinase-3 betaHomo sapiens (human)
Wnt signalosomeGlycogen synthase kinase-3 betaHomo sapiens (human)
cytosolGlycogen synthase kinase-3 betaHomo sapiens (human)
axonGlycogen synthase kinase-3 betaHomo sapiens (human)
nucleusGlycogen synthase kinase-3 betaHomo sapiens (human)
cytoplasmGlycogen synthase kinase-3 betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (55)

Assay IDTitleYearJournalArticle
AID1228442Effect on CK1alpha expression in human SW480 cells at 10 to 30 uM after 24 hrs by Western blot analysis2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228436Activation of GSK-3beta in human SW480 cells assessed as downregulation of beta-catenin expression in cytosolic fraction at 10 to 30 uM after 24 hrs by Western blot analysis2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228428Cytotoxicity against Wnt-independent human SW480 cells assessed as cell viability after 24 hrs by fluorescence assay2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228439Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Ser37 at 10 to 30 uM after 24 hrs by Western blot analysis2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228429Cytotoxicity against Wnt-dependent human HCT116 cells assessed as cell viability after 24 hrs by fluorescence assay2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID356499Cytotoxicity against human MCF7 cells by SRB assay2003Journal of natural products, Oct, Volume: 66, Issue:10
Cytotoxic and antimalarial beta-carboline alkaloids from the roots of Eurycoma longifolia.
AID1070421Inhibition of NF-kappaB activity in TNF-alpha stimulated human HEK-293/NF-kB-luc cells incubated for 30 mins prior to TNF-alpha challenge for 4 hrs by luciferase reporter gene assay2014Journal of natural products, Mar-28, Volume: 77, Issue:3
NF-κB inhibitors from Eurycoma longifolia.
AID1228443Effect on GSK-3beta expression in human SW480 cells at 10 to 30 uM after 24 hrs by Western blot analysis2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228433Activation of GSK-3beta in zebrafish embryo assessed as suppression of zic2a gene expression in midbrain tectum at 300 uM measured 4 to 24 hrs post fertilization by in situ hybridization method in presence of MO, p53 MO2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228452Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Ser33 at 30 uM after 24 hrs by Western blot analysis in presence of CK1alpha siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1918730Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1228422Activation of GSK-3beta in HEK293T cells assessed as suppression of TCF/beta-catenin transcriptional activity at 5 to 20 uM after 24 hrs by SuperFOPFlash reporter gene assay2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID338762Cytotoxicity against human melanoma cells
AID356500Antimalarial activity against Plasmodium falciparum W22003Journal of natural products, Oct, Volume: 66, Issue:10
Cytotoxic and antimalarial beta-carboline alkaloids from the roots of Eurycoma longifolia.
AID1228419Cytotoxicity against HEK293 cells transfected with SuperTOPFlash reporter gene assessed as cell viability at 5 to 20 uM after 24 hrs by fluorescence assay2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228440Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Thr41 at 10 to 30 uM after 24 hrs by Western blot analysis2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228450Inhibition of GSK-3beta phosphorylation at Ser9 in human SW480 cells at 30 uM after 24 hrs by Western blot analysis in presence of control and GSK-3beta siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228418Activation of GSK-3beta in HEK293 cells assessed as suppression of TCF/beta-catenin transcriptional activity after 24 hrs by SuperTOPFlash reporter gene assay2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1070420Growth inhibition of TNF-alpha stimulated human HEK-293/NF-kB-luc cells assessed as cell viability at 30 uM incubated for 30 mins prior to TNF-alpha challenge for 4 hrs by CellTracker Green CMFDA staining2014Journal of natural products, Mar-28, Volume: 77, Issue:3
NF-κB inhibitors from Eurycoma longifolia.
AID1228438Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Ser33 at 10 to 30 uM after 24 hrs by Western blot analysis2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1070422Inhibition of NF-kappaB activity in TNF-alpha stimulated human HEK-293/NF-kB-luc cells at 30 uM incubated for 30 mins prior to TNF-alpha challenge for 4 hrs by luciferase reporter gene assay2014Journal of natural products, Mar-28, Volume: 77, Issue:3
NF-κB inhibitors from Eurycoma longifolia.
AID338760Cytotoxicity against human KBV1 cells
AID338765Cytotoxicity against human colon cancer cells
AID1228448Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Ser37 at 30 uM after 24 hrs by Western blot analysis in presence of GSK-3beta siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228430Cytotoxicity against Wnt-dependent human DLD1 cells assessed as cell viability after 24 hrs by fluorescence assay2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228435Activation of GSK-3beta in zebrafish embryo assessed as reduction of pigment cells on tail at 300 uM measured 4 to 30 hrs post fertilization2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228444Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Ser33 at 30 uM after 24 hrs by Western blot analysis in presence of control siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1918732Cytotoxicity against human Calu-3 cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1228445Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Ser37 at 30 uM after 24 hrs by Western blot analysis in presence of control siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228426Cytotoxicity against HEK293T cells assessed as cell viability after 24 hrs by fluorescence assay2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228432Induction of apoptosis in zebrafish embryo at 300 uM measured 10 to 24 hrs post fertilization by TUNEL assay in presence of MO, p53 MO2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228454Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Thr41 at 30 uM after 24 hrs by Western blot analysis in presence of CK1alpha siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228425Cytotoxicity against HEK293 cells assessed as cell viability after 24 hrs by fluorescence assay2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID338761Cytotoxicity against human fibrosarcoma cells
AID1228449Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Thr41 at 30 uM after 24 hrs by Western blot analysis in presence of GSK-3beta siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID338766Cytotoxicity against mouse P388 cells
AID1228431Activation of GSK-3beta in zebrafish embryo assessed as suppression of Wnt/beta-catenin signaling pathway at 300 uM measured 10 to 24 hrs post fertilization by TOPdGFP reporter gene-based fluorescence microscopic analysis in presence of MO, p53 MO2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID338764Cytotoxicity against human breast cancer cells
AID338759Cytotoxicity against human KB cells
AID1228437Activation of GSK-3beta in human SW480 cells assessed as downregulation of beta-catenin expression in nuclear fraction at 10 to 30 uM after 24 hrs by Western blot analysis2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228451Activation of GSK-3beta in zebrafish embryo assessed as reduction of BIO-induced eyeless phenotype appearance at 100 uM measured 4 to 30 hrs post fertilization2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228427Cytotoxicity against Wnt-independent human RKO cells assessed as cell viability after 24 hrs by fluorescence assay2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1918733Cytotoxicity against human MRC5 cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1228441Effect on CK1alpha in human SW480 cells assessed as change in phosphorylation of beta-catenin at Ser45 at 10 to 30 uM after 24 hrs by Western blot analysis2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1918725Cytotoxicity against human HCT-8 cells assessed as redcution in cell viability at 10 uM incubated for 96 hrs by PrestoBlue reagent based assay relative to control2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1918734Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1918727Cytotoxicity against human HCT-8 cells assessed as redcution in cell viability incubated for 96 hrs by PrestoBlue reagent based assay2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID338763Cytotoxicity against human lung cancer cells
AID1918724Antiviral activity against HCoV-OC43 infected in human HCT-8 cells assessed as inhibition of viral growth at 10 uM incubated for 4 days by ELISA analysis relative to control2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1228455Inhibition of GSK-3beta phosphorylation at Ser9 in human SW480 cells at 30 uM after 24 hrs by Western blot analysis in presence of CK1alpha siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228446Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Thr41 at 30 uM after 24 hrs by Western blot analysis in presence of control siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228434Activation of GSK-3beta in zebrafish embryo assessed as suppression of mitf gene expression in neural crest cells at 300 uM measured 24 hrs post fertilization by in situ hybridization method in presence of MO, p53 MO2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228453Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Ser37 at 30 uM after 24 hrs by Western blot analysis in presence of CK1alpha siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID1228447Activation of GSK-3beta in human SW480 cells assessed as increase in phosphorylation of beta-catenin at Ser33 at 30 uM after 24 hrs by Western blot analysis in presence of GSK-3beta siRNA2015Journal of natural products, May-22, Volume: 78, Issue:5
9-Hydroxycanthin-6-one, a β-Carboline Alkaloid from Eurycoma longifolia, Is the First Wnt Signal Inhibitor through Activation of Glycogen Synthase Kinase 3β without Depending on Casein Kinase 1α.
AID356498Cytotoxicity against human A549 cells by SRB assay2003Journal of natural products, Oct, Volume: 66, Issue:10
Cytotoxic and antimalarial beta-carboline alkaloids from the roots of Eurycoma longifolia.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (14.29)29.6817
2010's5 (71.43)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.72

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 Index30.72 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index5.24 (4.65)
Search Engine Demand Index27.81 (26.88)
Search Engine Supply Index1.75 (0.95)

This Compound (30.72)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
vanillin
Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).		2.110benzaldehydes;
monomethoxybenzene;
phenols		anti-inflammatory agent;
anticonvulsant;
antioxidant;
flavouring agent;
plant metabolite
vanillic acid
Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.		2.110methoxybenzoic acid;
monohydroxybenzoic acid		plant metabolite
syringic acid
syringic acid: RN given refers to parent cpd; structure in third source. syringic acid : A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid.		2.110benzoic acids;
dimethoxybenzene;
phenols		plant metabolite
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.1710acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
brusatol
brusatol: quassinoid from B. javanica; structure		2.4110triterpenoid
canthin-6-one
canthin-6-one: from Zanthoxylum usambarense; structure in first source. canthin-6-one : An indole alkaloid that is 6H-indolo[3,2,1-de][1,5]naphthyridine substituted by an oxo group at position 6.		2.4820enone;
indole alkaloid;
organic heterotetracyclic compound		antimycobacterial drug;
metabolite
parthenolide
[no description available]		2.110germacranolide
3,3',4',5,6,7,8-heptamethoxyflavone
3,3',4',5,6,7,8-heptamethoxyflavone: has anti-inflammatory activity; isolated from citrus fruit; exhibit antiadhesive action on platelets		2.110ether;
flavonoids
bruceine a
bruceine A: quassinoid which inhibits protein synthesis & DNA synthesis in cells; RN given refers to (11 beta,12 alpha,15 beta)-isomer; structure given in first source		2.4110quassinoid
eurylene
eurylene: structure in first source		2.110
scopoletin
[no description available]		2.110hydroxycoumarinplant growth regulator;
plant metabolite
andrographolide
[no description available]		2.4110carbobicyclic compound;
gamma-lactone;
labdane diterpenoid;
primary alcohol;
secondary alcohol		anti-HIV agent;
anti-inflammatory drug;
antineoplastic agent;
metabolite
beta-carboline-1-propionic acid
[no description available]		2.4820harmala alkaloid
9-methoxycanthin-6-one
9-methoxycanthin-6-one: from roots of Eurycoma longifolia (Simaroubaceae). 9-methoxycanthin-6-one : An indole alkaloid that is the 9-methoxy derivative of canthin-6-one. Isolated from Eurycoma longifolia and Simaba multiflora, it exhibits cytotoxic activity towards human cancer cell lines.		3.0140aromatic ether;
indole alkaloid;
organic heterotetracyclic compound		antineoplastic agent;
antiplasmodial drug;
metabolite
pedunculoside
pedunculoside: from leaves of Ilex chinensis; structure given in first source		2.110
eurycomanone
[no description available]		2.5820cyclic ether;
delta-lactone;
enone;
organic heteropentacyclic compound;
pentol;
quassinoid;
secondary alcohol;
secondary alpha-hydroxy ketone;
tertiary alcohol		antimalarial;
antineoplastic agent;
metabolite
s 8932
[no description available]		2.4110aromatic amine;
C-nucleoside;
carboxylic ester;
nitrile;
phosphoramidate ester;
pyrrolotriazine		anticoronaviral agent;
antiviral drug;
prodrug
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.0110
Cancer of Lung
[description not available]		02.0110
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.0110
Lung Neoplasms
Tumors or cancer of the LUNG.		02.0110
2019 Novel Coronavirus Disease
[description not available]		04.0290
Catarrh
Inflammation of a mucous membrane with increased flow of mucous in humans or animals. Catarrh is used mostly in a historical context.		04.0290
Common Cold
A catarrhal disorder of the upper respiratory tract, which may be viral or a mixed infection. It generally involves a runny nose, nasal congestion, and sneezing.		04.0290
Cancer of Ovary
[description not available]		02.1710
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.1710