canthin-6-one profile

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

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. [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]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Zanthoxylum	genus	A 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]	Rutaceae	A plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]

ID Source	ID
PubMed CID	97176
CHEMBL ID	156897
CHEBI ID	3363
SCHEMBL ID	1515412
MeSH ID	M0422650

Synonym
6h-indolo[3,2,1-de][1,5]naphthyridin-6-one
ACON0_001416
MEGXP0_000046
nsc103003
canthin-6-one
nsc-103003
479-43-6
C09098 ,
6h-indolo(3,2,1-de)(1,5)naphthyridin-6-one
NCIOPEN2_007333
CHEMBL156897
chebi:3363 ,
M03828
indolo[3,2,1-de][1,5]naphthyridin-6-one
unii-3fk17s759n
nsc 103003
3fk17s759n ,
canthinone
SCHEMBL1515412
ZERVJPYNQLONEK-UHFFFAOYSA-N
AKOS026745853
DTXSID40197322
1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
ncgc00380132-01!
Q27106045
1,6-diazatetracyclo[7.6.1.0^{5,16.0^{10,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
C15843
MS-23224
B0005-188445
ldn-0022506
A872006
1,6-diazatetracyclo[7.6.1.0?,??.0??,??]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
CS-0023793
HY-N3536
GLXC-25937

Excerpt	Reference	Relevance
" MESf was shown to be relatively safe with NOAEL (100 mg/kg) when administrate in mice."	( Assessment of toxicity and differential antimicrobial activity of methanol extract of rhizome of Simaba ferruginea A. St.-Hil. and its isolate canthin-6-one. Arunachalam, K; Ascêncio, SD; Balogun, SO; Colodel, EM; Filho, VC; Gazoni, VF; Lima, SR; Martins, DTO; Oliveira, DM; Soares, IM, 2018)	0.68

Excerpt	Reference	Relevance
" The validated method was successfully applied to pharmacokinetic study in rats after intravenous (5 mg/kg) and oral (10, 25, 50 mg/kg) administration of 5-hydroxy-4-methoxycanthin-6-one."	( Pharmacokinetic and bioavailability study of 5-hydroxy-4-methoxycanthin-6-one, a typical canthinone alkaloid, in rats using ultra-high performance liquid chromatography/electrospray ionization tandem mass spectrometry. Guo, L; Zhang, L; Zhao, L; Zhao, Y, 2020)	0.99

Excerpt	Reference	Relevance
"11 h) and low bioavailability (16."	( Pharmacokinetic and bioavailability study of 5-hydroxy-4-methoxycanthin-6-one, a typical canthinone alkaloid, in rats using ultra-high performance liquid chromatography/electrospray ionization tandem mass spectrometry. Guo, L; Zhang, L; Zhao, L; Zhao, Y, 2020)	0.8

Excerpt	Relevance	Reference
" Chronic model of the disease showed that both canthin-6-one (1) and the alkaloidal extract at the above dosage induced 80-100% animal survival compared to untreated controls."	( Effects of canthin-6-one alkaloids from Zanthoxylum chiloperone on Trypanosoma cruzi-infected mice. de Arias, AR; de Bilbao, NV; Ferreira, ME; Fournet, A; Hocquemiller, R; Lagoutte, D; Nakayama, H; Poupon, E; Schinini, A; Serna, E; Soriano-Agatón, F, 2007)	0.99

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimycobacterial drug	A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.
[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]

Class	Description
indole alkaloid	An alkaloid containing an indole skeleton.
organic heterotetracyclic compound
enone	An 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.
[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	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Gamma-aminobutyric acid receptor subunit pi	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6561	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit beta-1	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6561	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit delta	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6561	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit gamma-2	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.5614	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit alpha-5	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6352	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit alpha-3	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6217	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit gamma-1	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6758	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit alpha-2	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6469	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit alpha-4	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6561	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit gamma-3	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6561	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit alpha-6	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6712	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit alpha-1	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.5577	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit beta-3	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6403	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit beta-2	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.5708	10.0000	AID40971
GABA theta subunit	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6561	10.0000	AID40971
Gamma-aminobutyric acid receptor subunit epsilon	Rattus norvegicus (Norway rat)	Ki	10.0000	0.0002	0.6561	10.0000	AID40971
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
plasma membrane	Gamma-aminobutyric acid receptor subunit gamma-2	Rattus norvegicus (Norway rat)
plasma membrane	Gamma-aminobutyric acid receptor subunit alpha-1	Rattus norvegicus (Norway rat)
plasma membrane	Gamma-aminobutyric acid receptor subunit beta-2	Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (102)

Assay ID	Title	Year	Journal	Article
AID1170713	Antiproliferative activity against rat C6 cells assessed as inhibition of cell growth at 10 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID404138	Antifungal activity against Cryptococcus neoformans H99	2005	Journal of natural products, Nov, Volume: 68, Issue:11	Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID1466361	Antibacterial activity against Staphylococcus aureus	2017	European journal of medicinal chemistry, Jul-07, Volume: 134	Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view.
AID1170704	Antiproliferative activity against human Jurkat cells assessed as inhibition of cell growth at 40 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170734	Reduction in mitotic spindles formation in human PC3 cells at 40 uM incubated for 48 hrs by tubulin immunofluorescence assay	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170716	Antiproliferative activity against human HT-29 cells assessed as induction of cell death at 40 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1918732	Cytotoxicity against human Calu-3 cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay	2022	Journal of natural products, 12-23, Volume: 85, Issue:12	Evaluating the
AID377125	Antiplatelet activity against rabbit platelets assessed as inhibition of arachidonic acid-induced platelet aggregation at 100 ug/ml preincubated for 3 mins by turbidimetric method	1999	Journal of natural products, Jun, Volume: 62, Issue:6	Chemical constituents and biological activities of the fruit of Zanthoxylum integrifoliolum.
AID333931	Genotoxicity in CHO cells assessed as chromosomal aberrations at 125 ppm after 90 mins in dark
AID333936	Genotoxicity in CHO cells assessed as mitotic inhibition at 3.9 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID333891	Phototoxicity against Saccharomyces cerevisiae at 10 ug/disk after irradiation with W/m'2 UV light
AID1529812	Antibacterial activity against multidrug-resistant Staphylococcus aureus 1199B after 24 hrs	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	Design, synthesis and biological evaluations of quaternization harman analogues as potential antibacterial agents.
AID333862	Phototoxicity against Pseudomonas fluorescens at 10 ug/disk in dark
AID333932	Genotoxicity in CHO cells assessed as chromosomal aberrations at 62.5 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID333874	Phototoxicity against Streptococcus faecalis at 10 ug/disk in dark
AID356499	Cytotoxicity against human MCF7 cells by SRB assay	2003	Journal of natural products, Oct, Volume: 66, Issue:10	Cytotoxic and antimalarial beta-carboline alkaloids from the roots of Eurycoma longifolia.
AID333930	Genotoxicity in CHO cells assessed as chromosomal aberrations at 125 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID377126	Antiplatelet activity against rabbit platelets assessed as inhibition of arachidonic acid-induced platelet aggregation at 50 ug/ml preincubated for 3 mins by turbidimetric method	1999	Journal of natural products, Jun, Volume: 62, Issue:6	Chemical constituents and biological activities of the fruit of Zanthoxylum integrifoliolum.
AID1268768	Antibacterial activity against Staphylococcus aureus after 12 to 16 hrs by plate reader analysis	2016	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2	Synthesis, in vitro antibacterial activities of a series of 3-N-substituted canthin-6-ones.
AID1170712	Antiproliferative activity against human HeLa cells assessed as inhibition of cell growth at 10 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID333850	Phototoxicity against Escherichia coli at 10 ug/disk in dark
AID1170702	Antiproliferative activity against human PC3 cells assessed as inhibition of cell growth at 40 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID333873	Phototoxicity against Streptococcus faecalis at 10 ug/disk after irradiation with W/m'2 UV light
AID404141	Antifungal activity against Aspergillus fumigatus 04-486	2005	Journal of natural products, Nov, Volume: 68, Issue:11	Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID333892	Phototoxicity against Saccharomyces cerevisiae at 10 ug/disk in dark
AID377136	Antiplatelet activity against rabbit platelets assessed as inhibition of PAF-induced platelet aggregation at 100 ug/ml preincubated for 3 mins by turbidimetric method	1999	Journal of natural products, Jun, Volume: 62, Issue:6	Chemical constituents and biological activities of the fruit of Zanthoxylum integrifoliolum.
AID332844	Cytotoxicity against human KB cells
AID1268770	Antibacterial activity against Pseudomonas solanacearum after 12 to 16 hrs by plate reader analysis	2016	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2	Synthesis, in vitro antibacterial activities of a series of 3-N-substituted canthin-6-ones.
AID400858	Cytotoxicity against GPK cells by [3H]thymidine incorporation assay
AID1918730	Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay	2022	Journal of natural products, 12-23, Volume: 85, Issue:12	Evaluating the
AID1529814	Antibacterial activity against methicillin-resistant Staphylococcus aureus EMRSA15 after 24 hrs	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	Design, synthesis and biological evaluations of quaternization harman analogues as potential antibacterial agents.
AID1170710	Antiproliferative activity against human HT-29 cells assessed as inhibition of cell growth at 10 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID333856	Phototoxicity against Pseudomonas aeruginosa at 10 ug/disk in dark
AID1170711	Antiproliferative activity against human Jurkat cells assessed as inhibition of cell growth at 10 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID333880	Phototoxicity against Staphylococcus aureus at 10 ug/disk in dark
AID404139	Antifungal activity against Saccharomyces cerevisiae ATCC 26.01	2005	Journal of natural products, Nov, Volume: 68, Issue:11	Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID1918733	Cytotoxicity against human MRC5 cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay	2022	Journal of natural products, 12-23, Volume: 85, Issue:12	Evaluating the
AID333935	Genotoxicity in CHO cells assessed as chromosomal aberrations at 7.8 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID356500	Antimalarial activity against Plasmodium falciparum W2	2003	Journal of natural products, Oct, Volume: 66, Issue:10	Cytotoxic and antimalarial beta-carboline alkaloids from the roots of Eurycoma longifolia.
AID394502	Inhibition of Escherichia coli recombinant DNA gyrase assessed as enzyme-mediated supercoiling of relaxed pRSET A-DNA at 170 uM by agarose gel electrophoresis in presence of 0.01% Triton X-100	2007	Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10	Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening.
AID333849	Phototoxicity against Escherichia coli at 10 ug/disk after irradiation with W/m'2 UV light
AID333879	Phototoxicity against Staphylococcus aureus at 10 ug/disk after irradiation with W/m'2 UV light
AID394507	Binding affinity to pGEM2 DNA assessed as DNA intercalation at >=50 uM by DNA unwinding assay	2007	Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10	Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening.
AID377120	Antiplatelet activity against rabbit platelets assessed as inhibition of thrombin-induced platelet aggregation at 100 ug/ml preincubated for 3 mins by turbidimetric method	1999	Journal of natural products, Jun, Volume: 62, Issue:6	Chemical constituents and biological activities of the fruit of Zanthoxylum integrifoliolum.
AID394500	Inhibition of Escherichia coli recombinant DNA gyrase assessed as enzyme-mediated supercoiling of relaxed pRSET A-DNA at 170 uM by agarose gel electrophoresis	2007	Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10	Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening.
AID1170714	Antiproliferative activity against mouse NIH/3T3 cells assessed as inhibition of cell growth at 10 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID333861	Phototoxicity against Pseudomonas fluorescens at 10 ug/disk after irradiation with W/m'2 UV light
AID1918734	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay	2022	Journal of natural products, 12-23, Volume: 85, Issue:12	Evaluating the
AID1170721	Induction of apoptosis in human PC3 cells assessed as induction of procaspase-3 cleavage at 40 uM after 48 hrs by Western blot method	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170732	Induction of cell cycle arrest in human PC3 cells assessed as accumulation at S phase at 40 uM incubated for 48 hrs by propidium iodide staining based flow cytometry (Rvb = 21.6 +/- 0.2%)	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170715	Antiproliferative activity against human PC3 cells assessed as induction of cell death at 40 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170722	Induction of apoptosis in human PC3 cells assessed as induction of procaspase-3 cleavage at 40 uM after 96 hrs by Western blot method	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170703	Antiproliferative activity against human HT-29 cells assessed as inhibition of cell growth at 40 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170718	Antiproliferative activity against human HeLa cells assessed as induction of cell death at 40 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID333885	Phototoxicity against Candida albicans at 10 ug/disk after irradiation with W/m'2 UV light
AID394504	Inhibition of Escherichia coli recombinant DNA gyrase assessed as enzyme-mediated supercoiling of relaxed pRSET A-DNA at 170 uM by agarose gel electrophoresis in presence of 0.025% Triton X-100	2007	Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10	Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening.
AID1170739	Toxicity against human NHDF assessed as reduction in cell viability incubated for 3 days by MTT assay	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID404140	Antifungal activity against Trichophyton mentagrophytes var. interdigitale CPCM 06.99	2005	Journal of natural products, Nov, Volume: 68, Issue:11	Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID1170735	Toxicity against human NHDF assessed as cell viability up to 20 uM incubated for 3 days by MTT assay	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID333867	Phototoxicity against Bacillus subtilis at 10 ug/disk after irradiation with W/m'2 UV light
AID1170720	Antiproliferative activity against mouse NIH/3T3 cells assessed as induction of cell death at 40 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1466365	Antibacterial activity against Mycobacterium	2017	European journal of medicinal chemistry, Jul-07, Volume: 134	Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view.
AID333934	Genotoxicity in CHO cells assessed as chromosomal aberrations at 15.6 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID333933	Genotoxicity in CHO cells assessed as chromosomal aberrations at 31.2 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID1170707	Antiproliferative activity against human HeLa cells assessed as inhibition of cell growth at 40 uM after 2 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170706	Antiproliferative activity against mouse NIH/3T3 cells assessed as inhibition of cell growth at 40 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1529813	Antibacterial activity against multidrug-resistant Staphylococcus aureus XU212 after 24 hrs	2018	European journal of medicinal chemistry, Dec-05, Volume: 160	Design, synthesis and biological evaluations of quaternization harman analogues as potential antibacterial agents.
AID1170726	Induction of apoptosis in human Jurkat cells assessed as induction of procaspase-3 cleavage at 40 uM after 48 hrs by Western blot method	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID394498	Inhibition of Escherichia coli recombinant DNA gyrase-mediated supercoiling of relaxed pRSET A-DNA by agarose gel electrophoresis	2007	Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10	Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening.
AID333937	Genotoxicity in CHO cells assessed as chromosomal aberrations at 1.9 ppm after 60 mins in dark followed by 5 W/m'2 UV irradiation for 30 mins
AID1170736	Toxicity against human NHDF assessed as cell viability at 40 uM incubated for 3 days by MTT assay	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170737	Toxicity against human NHDF assessed as cell viability at 80 uM incubated for 3 days by MTT assay	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID333886	Phototoxicity against Candida albicans at 10 ug/disk in dark
AID1170708	Antiproliferative activity against human HeLa cells assessed as inhibition of cell growth at 10 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170729	Inhibition of DNA synthesis in human PC3 cells assessed as reduction in BrdU incorporation at 40 uM pre-incubated for 30 hrs by Southern blotting method	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID356498	Cytotoxicity against human A549 cells by SRB assay	2003	Journal of natural products, Oct, Volume: 66, Issue:10	Cytotoxic and antimalarial beta-carboline alkaloids from the roots of Eurycoma longifolia.
AID1918725	Cytotoxicity 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 control	2022	Journal of natural products, 12-23, Volume: 85, Issue:12	Evaluating the
AID1170724	Induction of apoptosis in human HeLa cells assessed as induction of procaspase-3 cleavage at 10 uM after 48 hrs by Western blot method	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170738	Toxicity against human NHDF assessed as cell viability at 160 uM incubated for 3 days by MTT assay	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID404137	Antifungal activity against Candida albicans ATCC 10231	2005	Journal of natural products, Nov, Volume: 68, Issue:11	Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.
AID1170723	Induction of apoptosis in human HT-29 cells assessed as induction of procaspase-3 cleavage at 40 uM after 48 hrs by Western blot method	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID333855	Phototoxicity against Pseudomonas aeruginosa at 10 ug/disk after irradiation with W/m'2 UV light
AID1170717	Antiproliferative activity against human Jurkat cells assessed as induction of cell death at 40 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID40971	In vitro inhibition of [3H]diazepam binding to rat cerebral cortical membrane benzodiazepine receptors	1984	Journal of medicinal chemistry, May, Volume: 27, Issue:5	Biomimetic approach to potential benzodiazepine receptor agonists and antagonists.
AID1170733	Induction of cell cycle arrest in human PC3 cells assessed as accumulation at G2/M phase at 40 uM incubated for 48 hrs by flow propidium iodide staining based flow cytometry (Rvb = 20 +/- 0.6%)	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170727	Induction of apoptosis in rat C6 cells assessed as induction of procaspase-3 cleavage at 40 uM after 48 hrs by Western blot method	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1918727	Cytotoxicity against human HCT-8 cells assessed as redcution in cell viability incubated for 96 hrs by PrestoBlue reagent based assay	2022	Journal of natural products, 12-23, Volume: 85, Issue:12	Evaluating the
AID1170719	Antiproliferative activity against rat C6 cells assessed as induction of cell death at 40 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170731	Induction of cell cycle arrest in human PC3 cells assessed as accumulation at G1 phase at 40 uM incubated for 48 hrs by propidium iodide staining based flow cytometry (Rvb = 57.8 +/- 0.6%)	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID377131	Antiplatelet activity against rabbit platelets assessed as inhibition of collagen-induced platelet aggregation at 100 ug/ml preincubated for 3 mins by turbidimetric method	1999	Journal of natural products, Jun, Volume: 62, Issue:6	Chemical constituents and biological activities of the fruit of Zanthoxylum integrifoliolum.
AID1194597	Inhibition of PTP1B (unknown origin) assessed as inhibition rate at 100 uM	2015	Bioorganic & medicinal chemistry letters, May-01, Volume: 25, Issue:9	Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.
AID1268771	Antibacterial activity against Ralstonia solanacearum after 12 to 16 hrs by plate reader analysis	2016	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2	Synthesis, in vitro antibacterial activities of a series of 3-N-substituted canthin-6-ones.
AID1170709	Antiproliferative activity against human PC3 cells assessed as inhibition of cell growth at 10 to 60 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170705	Antiproliferative activity against rat C6 cells assessed as inhibition of cell growth at 40 uM after 4 days	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170730	Inhibition of DNA synthesis in human PC3 cells assessed as reduction in post-mitotic nuclei level at 40 uM pre-incubated for 30 hrs by immunofluorescence microscopy (Rvb = 85%)	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1170725	Induction of apoptosis in human HeLa cells assessed as induction of procaspase-3 cleavage at 30 uM after 48 hrs by Western blot method	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID333868	Phototoxicity against Bacillus subtilis at 10 ug/disk in dark
AID1268769	Antibacterial activity against Bacillus cereus after 12 to 16 hrs by plate reader analysis	2016	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 26, Issue:2	Synthesis, in vitro antibacterial activities of a series of 3-N-substituted canthin-6-ones.
AID1918724	Antiviral 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 control	2022	Journal of natural products, 12-23, Volume: 85, Issue:12	Evaluating the
AID1170728	Induction of apoptosis in mouse NIH/3T3 cells assessed as induction of procaspase-3 cleavage at 40 uM after 48 hrs by Western blot method	2014	Journal of natural products, Nov-26, Volume: 77, Issue:11	Canthin-6-one displays antiproliferative activity and causes accumulation of cancer cells in the G2/M phase.
AID1794808	Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).	2014	Journal of biomolecular screening, Jul, Volume: 19, Issue:6	A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808	Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (2.00)	18.7374
1990's	1 (2.00)	18.2507
2000's	8 (16.00)	29.6817
2010's	29 (58.00)	24.3611
2020's	11 (22.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	4 (7.41%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	50 (92.59%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.51	2	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
mandelic acid SAMMA: mandelic acid condensation polymer	2.03	1	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	2.03	1	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	1.96	1	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	2.72	3	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
2-phenylglycine 2-phenylglycine: RN given refers to cpd without isomeric designation; structure. alpha-phenylglycine : An amino acid with a structure in which a phenyl ring is bonded to the alpha-carbon of glycine.	2.03	1	non-proteinogenic alpha-amino acid	human metabolite
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2	1	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	2	1	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
pregnenolone [no description available]	2	1	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
aminoimidazole carboxamide Aminoimidazole Carboxamide: An imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases.. 5-aminoimidazole-4-carboxamide : An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4.	2.03	1	aminoimidazole; monocarboxylic acid amide	mouse metabolite
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.03	1	C-nitro compound; imidazoles	antitubercular agent
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.06	1	dialdehyde	biomarker
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	2.31	1	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
2-tridecanone tridecan-2-one : A methyl ketone that is tridecane in which the methylene hydrogens at position 2 are replaced by an oxo group.	2	1	methyl ketone	flavouring agent; plant metabolite
2-hydroxybenzothiazole 2-hydroxybenzothiazole : Benzothiazole substituted with a hydroxy group at the 2-position.	2.03	1	benzothiazole
canadine, (s)-isomer (S)-canadine : The (S)-enantiomer of canadine.	2	1	an (S)-7,8,13,14-tetrahydroprotoberberine; canadine	plant metabolite
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.05	1	metal allergen; nickel group element atom; platinum group metal atom
benzonidazole benzonidazole: used in treatment of Chagas' disease. benznidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.	2.03	1	C-nitro compound; imidazoles; monocarboxylic acid amide	antiprotozoal drug
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	3.25	1	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
permethrin hemoglobin Atlanta-Coventry: Leu replaced by Pro at beta75 and Leu deleted at beta141	2.01	1	cyclopropanecarboxylate ester; cyclopropanes	agrochemical; ectoparasiticide; pyrethroid ester acaricide; pyrethroid ester insecticide; scabicide
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.11	1	D-glucopyranose	epitope; mouse metabolite
7-methylxanthine [no description available]	2.03	1	oxopurine; purine alkaloid	human xenobiotic metabolite; mouse metabolite; plant metabolite
sesamin (+)-sesamin : A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.	2	1	benzodioxoles; furofuran; lignan	antineoplastic agent; neuroprotective agent; plant metabolite
brusatol brusatol: quassinoid from B. javanica; structure	2.41	1	triterpenoid
1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid: precursor of mutagenic nitroso cpd in soy sauce; structure given in first source	2.11	1	harmala alkaloid
cryptolepine cryptolepine: fused indole-quinoline; structure in first source; from CRYPTOLEPIS sanguinolenta. cryptolepine : An organic heterotetracyclic compound that is 5H-indolo[3,2-b]quinoline in which the hydrogen at position N-5 is replaced by a methyl group.	3.25	1	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound	anti-inflammatory agent; antimalarial; antineoplastic agent; cysteine protease inhibitor; plant metabolite
inermin inermin: phytoalexin produced in plants after injection with fungi; RN given refers to (cis-(+-))-isomer; RN for cpd without isomeric designation; structure. (-)-maackiain : The (-)-enantiomer of maackiain.	2.1	1	maackiain
1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid: structure given in first source; RN given refers to cpd without isomeric designation. 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid : A member of the class of beta-carbolines that is 1,2,3,4-tetrahydro-beta-carboline substituted at position 3 by a carboxy group.	2.11	1	alpha-amino acid; aromatic amino acid; beta-carboline alkaloid	human urinary metabolite; human xenobiotic metabolite; plant metabolite; rat metabolite
beta-carboline-3-carboxylic acid ethyl ester beta-carboline-3-carboxylic acid ethyl ester: isolated from brain tissue & urine; extremely potent displacer of diazepam from brain benzodiazepam receptors; structure in first source	1.96	1	beta-carbolines
beta-carboline-3-carboxylic acid methyl ester beta-carboline-3-carboxylic acid methyl ester: structure given in first source	2.4	2	beta-carbolines
cryptolepine monohydrochloride [no description available]	3.25	1
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	2.41	1	quassinoid
eurylene eurylene: structure in first source	2.1	1
uleine uleine: from the bark of Plumeria lancifolia; structure in first source	3.25	1
5-methoxycanthin-6-one 5-methoxycanthin-6-one: isolated from Zanthoxylum chiloperone; structure in first source	3.14	5	alkaloid; organic heterotetracyclic compound
Amalorin [no description available]	2.11	1	alkaloid; organic heterotetracyclic compound
neocryptolepine neocryptolepine: isolated from the roots of the African plant Cryptolepis sanguinolenta; structure in first source	3.25	1
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	2.1	1	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.21	1	stilbene
Methyl nigakinone 4,5-dimethoxycanthin-6-one: an active metabolite of Picrasma quassiodes; structure in first source	2.11	1	beta-carbolines
1-acetyl-beta-carboline 1-acetyl-beta-carboline: structure in first source	2.11	1	harmala alkaloid	metabolite
methyl isoquinoline-3-carboxylate [no description available]	1.96	1	isoquinolines
2,4-dithiobiuret 2,4-dithiobiuret: structure	2.03	1
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.06	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
scopoletin [no description available]	7.46	2	hydroxycoumarin	plant growth regulator; plant metabolite
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	2.04	1	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
harman harman: a beta-carboline; RN given refers to parent cpd; structure. harman : An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.	2.54	2	harmala alkaloid; indole alkaloid fundamental parent; indole alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
pellitorine pellitorine: consists of piper sylvaticum Roxb.; structure	2.01	1	fatty amide	metabolite
andrographolide [no description available]	2.41	1	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
dehydrocrenatidine dehydrocrenatidine: a janus kinase inhibitor; structure in first source	2.11	1
nigakinone nigakinone: an NSAID that may be useful in treating ulcerative colitis; structure in first source	2.57	2	beta-carbolines
1-Ethyl-9H-pyrido[3,4-b]indole [no description available]	2.11	1	harmala alkaloid
3-hydroxymethyl-beta-carboline 3-hydroxymethyl-beta-carboline: antagonizes anticonvulsant & anxiolytic actions of diazepam at doses which do not elicit overt behavioral effects in mice	1.96	1	beta-carbolines
beta-carboline-1-propionic acid [no description available]	2.78	3	harmala alkaloid
1-methyl-beta-carboline-3-carboxylic acid 1-methyl-beta-carboline-3-carboxylic acid: metabolite from cows fed with corn silage; structure in first source	2.11	1
laq824 LAQ824: Histone deacetylase inhibitor	3.25	1
manzamine a manzamine A: RN given refers to (1R-(1R,9Z,13S,13aR,20aR,21aR*)-isomer; RN for cpd without isomeric designation not avail 12/92. manzamine A : An alkaloid of the class of beta-carbolines isolated from Haliclona and Acanthostrongylophora. It exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).	3.25	1	alkaloid; beta-carbolines; isoquinolines	animal metabolite; anti-HSV-1 agent; antimalarial; antineoplastic agent; EC 2.7.11.26 (tau-protein kinase) inhibitor; marine metabolite
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	2.06	1	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
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.	3.01	4	aromatic ether; indole alkaloid; organic heterotetracyclic compound	antineoplastic agent; antiplasmodial drug; metabolite
9-hydroxycanthin-6-one 9-hydroxycanthin-6-one: from Eurycoma longifolia Jack (Simaroubaceae), induces penile erection and delays ejaculation. 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.	2.48	2
cefotaxime sodium [no description available]	2.17	1	organic sodium salt
drymaritin drymaritin: anti-HIV alkaloid from Drymaria diandra; structure in first source. drymaritin : An indole alkaloid that is canthin-6-one substituted by a methoxy group at position 4. Isolated from the whole plants of Drymaria diandra, it exhibits anti-HIV activity.	2.1	1	enol ether; enone; indole alkaloid; organic heterotetracyclic compound	anti-HIV agent; metabolite
pf-562,271 [no description available]	3.25	1	indoles
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	2.07	1
trans-avicennol trans-avicennol: from Zanthoxylum chiloperone var. angustifolium; structure in first source	2.47	2
ampicillin sodium [no description available]	2.55	2	organic sodium salt
eurycomanone [no description available]	2.41	1	cyclic ether; delta-lactone; enone; organic heteropentacyclic compound; pentol; quassinoid; secondary alcohol; secondary alpha-hydroxy ketone; tertiary alcohol	antimalarial; antineoplastic agent; metabolite
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.52	2	benzenes; hydroxycoumarin; methyl ketone
rk 682 [no description available]	2.11	1
s 8932 [no description available]	2.41	1	aromatic amine; C-nucleoside; carboxylic ester; nitrile; phosphoramidate ester; pyrrolotriazine	anticoronaviral agent; antiviral drug; prodrug
indolmycin indolmycin: produced by a strain of Streptomyces griseus; RN given refers to cpd without isomeric designation; structure. indolmycin : A member of the class of 1,3-oxazoles that is 1,3-oxazol-4(5H)-one which is substituted at the 2 and 5-pro-S positions by methylamino and [(1R)-1-(1H-indol-3-yl)ethyl] groups, respectively.	3.25	1	1,3-oxazoles; indoles; secondary amino compound	antibacterial agent; antimicrobial agent; bacterial metabolite; EC 6.1.1.2 (tryptophan--tRNA ligase) inhibitor
trigonoliimine a trigonoliimine A: from the leaves of Trigonostemon lii; structure in first source	3.25	1

Condition	Relationship Strength	Studies
Breast Cancer [description not available]	2.01	1
Cancer of Lung [description not available]	2.01	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.01	1
Lung Neoplasms Tumors or cancer of the LUNG.	2.01	1
Plasmodium falciparum Malaria [description not available]	2.1	1
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	2.1	1
Cancer of Prostate [description not available]	2.49	2
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.49	2
Infections, Staphylococcal [description not available]	2.13	1
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2.13	1
Bacterial Disease [description not available]	3.06	1
Abdominal Migraine [description not available]	3.06	1
Fungal Diseases [description not available]	3.06	1
Benign Neoplasms [description not available]	3.42	2
Viral Diseases [description not available]	3.06	1
Bacterial Infections Infections by bacteria, general or unspecified.	3.06	1
Migraine Disorders A class of disabling primary headache disorders, characterized by recurrent unilateral pulsatile headaches. The two major subtypes are common migraine (without aura) and classic migraine (with aura or neurological symptoms). (International Classification of Headache Disorders, 2nd ed. Cephalalgia 2004: suppl 1)	3.06	1
Mycoses Diseases caused by FUNGI.	3.06	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.42	2
Virus Diseases A general term for diseases caused by viruses.	3.06	1
2019 Novel Coronavirus Disease [description not available]	4.02	9
Catarrh Inflammation of a mucous membrane with increased flow of mucous in humans or animals. Catarrh is used mostly in a historical context.	4.02	9
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.	4.02	9
Acute Myelogenous Leukemia [description not available]	2.41	1
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	2.41	1
Innate Inflammatory Response [description not available]	2.63	2
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	7.31	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	7.63	2
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.45	2
Gastric Ulcer [description not available]	2.06	1
Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	2.06	1
Leishmania Infection [description not available]	2.44	2
American Trypanosomiasis [description not available]	2.46	2
Leishmaniasis A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).	2.44	2
Chagas Disease Infection with the protozoan parasite TRYPANOSOMA CRUZI, a form of TRYPANOSOMIASIS endemic in Central and South America. It is named after the Brazilian physician Carlos Chagas, who discovered the parasite. Infection by the parasite (positive serologic result only) is distinguished from the clinical manifestations that develop years later, such as destruction of PARASYMPATHETIC GANGLIA; CHAGAS CARDIOMYOPATHY; and dysfunction of the ESOPHAGUS or COLON.	2.46	2
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.25	1

canthin-6-one

Description

Cross-References

Synonyms (35)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Roles (2)

Drug Classes (3)

Protein Targets (16)

Inhibition Measurements

Ceullar Components (1)

Bioassays (102)

Research

Studies (50)

Market Indicators

Research Demand Index: 24.95

Study Types

canthin-6-one

Description

Related Flora

Cross-References

Synonyms (35)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Roles (2)

Drug Classes (3)

Protein Targets (16)

Inhibition Measurements

Ceullar Components (1)

Bioassays (102)

Research

Studies (50)

Market Indicators

Research Demand Index: 24.95

Study Types

Related Drugs (73)

Related Conditions (36)