Page last updated: 2024-11-08

5-methoxycanthin-6-one

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Description

5-methoxycanthin-6-one: isolated from Zanthoxylum chiloperone; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
ZanthoxylumgenusA plant genus of the family RUTACEAE. Some members of Zanthoxylum are reclassified from ELEUTHEROCOCCUS, Melicope, and EVODIA. The twigs are used as dental brushing sticks (TOOTHBRUSHING). Most plants that are called Fagara have been reclassified as Zanthoxylum, however some Fagara were reclassified to MELICOPE (also in the Rutacea family) or to GLEDITSIA (a genus in the FABACEAE family).[MeSH]RutaceaeA plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]

Cross-References

ID SourceID
PubMed CID259218
CHEMBL ID508649
CHEBI ID174289
SCHEMBL ID12762810
MeSH IDM0442797

Synonyms (29)

Synonym
canthin-6-one, 5-methoxy-
nsc88929
methoxycanthin-6-one,5-
nsc-88929
15071-56-4
5-methoxy-6h-indolo[3,2,1-de][1,5]naphthyridin-6-one
CHEBI:174289
3-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
5-methoxycanthin-6-one
6h-indolo[3,2,1-de][1,5]naphthyridin-6-one, 5-methoxy-
CHEMBL508649
5-methoxycanthinone
bdbm50067500
5-methoxy-6h-indolo(3,2,1-de)(1,5)naphthyridin-6-one
5-methoxy-canthin-6-one
unii-vvm1a8lm35
vvm1a8lm35 ,
nsc 88929
6h-indolo(3,2,1-de)(1,5)naphthyridin-6-one, 5-methoxy-
SCHEMBL12762810
TXEFUSAHPIYZHD-UHFFFAOYSA-N
DTXSID6074544
3-methoxy-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
5-methoxy-6h-indolo[3,2,1-de][1,5]naphthyridin-6-one, 9ci
Q27292037
3-methoxy-1,6-diazatetracyclo[7.6.1.0?,??.0??,??]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one
PD130606
methoxycanthinone, 5-
AKOS040761180
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
alkaloidAny of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
organic heterotetracyclic compound
[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)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)20.30000.00053.49849.7600AID1194589
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)Ki10.33000.19004.83279.6000AID1194591
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
positive regulation of JUN kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
actin cytoskeleton organizationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of endocytosisTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulum unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of intracellular protein transportTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cellular response to unfolded proteinTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of MAP kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of protein tyrosine kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of receptor catabolic processTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
RNA bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
zinc ion bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
enzyme bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cadherin bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
ephrin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein phosphatase 2A bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
plasma membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial matrixTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial cristaTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
sorting endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein-containing complexTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (54)

Assay IDTitleYearJournalArticle
AID333875Phototoxicity against Streptococcus faecalis at 16.7 ug/disk after irradiation with W/m'2 UV light
AID378654Cytotoxicity against human HCT8 cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID378656Cytotoxicity against human MCF7 cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID333944Genotoxicity in CHO cells assessed as mitotic inhibition at 2.6 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID1194592Inhibition of PTP1B (unknown origin) assessed as inhibition rate at 75 uM2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID404141Antifungal activity against Aspergillus fumigatus 04-4862005Journal of natural products, Nov, Volume: 68, Issue:11
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID404140Antifungal activity against Trichophyton mentagrophytes var. interdigitale CPCM 06.992005Journal of natural products, Nov, Volume: 68, Issue:11
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID333869Phototoxicity against Bacillus subtilis at 16.7 ug/disk after irradiation with W/m'2 UV light
AID333882Phototoxicity against Staphylococcus aureus at 16.7 ug/disk in dark
AID1080739Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana tabacum cv. K326 leaves assessed as inhibition of viral replication at 50 ug/mL in presence of 25 ug/mL quassinoid nigakilactone B measured 48 hr after compound exposure by leaf-d2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID378655Cytotoxicity against human CAKI1 cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID333887Phototoxicity against Candida albicans at 16.7 ug/disk after irradiation with W/m'2 UV light
AID333851Phototoxicity against Escherichia coli at 16.7 ug/disk after irradiation with W/m'2 UV light
AID378653Cytotoxicity against human A549 cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID1194591Non-competitive inhibition of PTP1B (unknown origin) assessed as hydrolysis of para-nitrophenylphosphate by Lineweaver-Burk plot2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID333881Phototoxicity against Staphylococcus aureus at 16.7 ug/disk after irradiation with W/m'2 UV light
AID1080742Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana glutinosa leaves assessed as inhibition of viral replication at 50 ug/mL measured 48 hr after compound exposure by half leaf method2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID1080741Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana glutinosa leaves assessed as inhibition of viral replication at 50 ug/mL in presence of 25 ug/mL quassinoid nigakilactone B measured 48 hr after compound exposure by half leaf met2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID1194609Ratio of inhibition rate for PTP1B (unknown origin) at 75 uM to inhibition rate for SHP1 (unknown origin) at 75 uM2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID333907Genotoxicity in CHO cells assessed as chromosomal aberrations at 1.3 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID333863Phototoxicity against Pseudomonas fluorescens at 16.7 ug/disk after irradiation with W/m'2 UV light
AID1194610Ratio of inhibition rate for PTP1B (unknown origin) at 75 uM to inhibition rate for SHP2 (unknown origin) at 75 uM2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID1194596Inhibition of SHP2 (unknown origin) assessed as inhibition rate at 75 uM2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID378657Cytotoxicity against human SK-MEL-2 cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID378652Cytotoxicity against human KB cells after 3 days by SRB assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
AID333893Phototoxicity against Saccharomyces cerevisiae at 16.7 ug/disk after irradiation with W/m'2 UV light
AID1194595Inhibition of SHP1 (unknown origin) assessed as inhibition rate at 75 uM2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID404138Antifungal activity against Cryptococcus neoformans H992005Journal of natural products, Nov, Volume: 68, Issue:11
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID333870Phototoxicity against Bacillus subtilis at 16.7 ug/disk in dark
AID404139Antifungal activity against Saccharomyces cerevisiae ATCC 26.012005Journal of natural products, Nov, Volume: 68, Issue:11
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID1194608Ratio of inhibition rate for PTP1B (unknown origin) at 75 uM to inhibition rate for VHR (unknown origin) at 75 uM2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID333857Phototoxicity against Pseudomonas aeruginosa at 16.7 ug/disk after irradiation with W/m'2 UV light
AID333864Phototoxicity against Pseudomonas fluorescens at 16.7 ug/disk in dark
AID333876Phototoxicity against Streptococcus faecalis at 16.7 ug/disk in dark
AID404137Antifungal activity against Candida albicans ATCC 102312005Journal of natural products, Nov, Volume: 68, Issue:11
Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID1080740Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana tabacum cv. K326 leaves assessed as inhibition of viral replication at 50 ug/mL measured 48 hr after compound exposure by leaf-disk method2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID333943Genotoxicity in CHO cells assessed as chromosomal aberrations at 5.2 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID1194589Inhibition of PTP1B (unknown origin)2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID1194594Inhibition of VHR (unknown origin) assessed as inhibition rate at 75 uM2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID333894Phototoxicity against Saccharomyces cerevisiae at 16.7 ug/disk in dark
AID1080737Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana glutinosa leaves assessed as inhibition of viral infection at 50 ug/mL using compound pre-treated virus suspension measured 5 to 6 days after compound exposure2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID333942Genotoxicity in CHO cells assessed as chromosomal aberrations at 10.4 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID333940Genotoxicity in CHO cells assessed as chromosomal aberrations at 41.7 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID400858Cytotoxicity against GPK cells by [3H]thymidine incorporation assay
AID333941Genotoxicity in CHO cells assessed as chromosomal aberrations at 20.8 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID1194593Inhibition of TCPTP (unknown origin) assessed as inhibition rate at 75 uM2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID333939Genotoxicity in CHO cells assessed as chromosomal aberrations at 83.5 ppm after 90 mins in dark
AID1080738Antiviral activity against Tobacco mosaic virus U1 (TMV) infected Nicotiana glutinosa leaves assessed as inhibition of viral infection at 50 ug/mL using compound pre-treated virus suspension in presence of 25 ug/mL quassinoid nigakilactone B measured 5 to2009Journal of agricultural and food chemistry, Aug-12, Volume: 57, Issue:15
Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn.
AID1194607Ratio of inhibition rate for PTP1B (unknown origin) at 75 uM to inhibition rate for TCPTP (unknown origin) at 75 uM2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID333852Phototoxicity against Escherichia coli at 16.7 ug/disk in dark
AID1194619Induction of Akt phosphorylation in insulin-stimulated human HepG2 cells assessed as pAkt/Akt ratio at 50 uM after 5 mins by western blotting analysis relative to control2015Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9
Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID333858Phototoxicity against Pseudomonas aeruginosa at 16.7 ug/disk in dark
AID333888Phototoxicity against Candida albicans at 16.7 ug/disk in dark
AID333938Genotoxicity in CHO cells assessed as chromosomal aberrations at 83.5 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (55.56)29.6817
2010's4 (44.44)24.3611
2020's0 (0.00)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 Index2.48 (2.92)
Research Growth Index4.92 (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%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]