9-methoxycanthin-6-one: from roots of Eurycoma longifolia (Simaroubaceae) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
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. [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]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Simaba | genus | A plant genus. Members contain QUASSINOIDS.[MeSH] | Simaroubaceae | A 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 | genus | A plant genus of the family SIMAROUBACEAE. Members contain quassinoids. There is Malaysian folk use of these plants for male virility.[MeSH] | Simaroubaceae | A 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] |
| Simaba multiflora | species | [no description available] | Simaroubaceae | A 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 longifolia | species | [no description available] | Simaroubaceae | A 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] |
| ID Source | ID |
|---|---|
| PubMed CID | 9881423 |
| CHEMBL ID | 504978 |
| CHEBI ID | 66699 |
| MeSH ID | M0430866 |
| Synonym |
|---|
| chebi:66699 , |
| CHEMBL504978 |
| 74991-91-6 |
| 8-methoxycanthin-6-one |
| 9-methoxycanthin-6-one |
| 13-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 |
| 9-methoxy-6h-indolo[3,2,1-de][1,5]naphthyridin-6-one |
| c15h10n2o2 |
| DTXSID90432290 |
| 13-methoxy-1,6-diazatetracyclo[7.6.1.0?,(1)?.0(1)?,(1)?]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one |
| AS-57655 |
| NCGC00385518-01 |
| 13-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one |
| Q27135320 |
| HY-112642 |
| BCP33217 |
| CS-0058761 |
| D93564 |
| AKOS037515610 |
| ZCA99191 |
| 13-methoxy-1,6-diazatetracyclo[7.6.1.0?,??.0??,??]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one |
| PD098532 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
| Role | Description |
|---|---|
| metabolite | Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. |
| antineoplastic agent | A substance that inhibits or prevents the proliferation of neoplasms. |
| antiplasmodial drug | An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria. |
| [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. |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| 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] | |
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1347160 | Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1347159 | Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1070421 | Inhibition 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 assay | 2014 | Journal of natural products, Mar-28, Volume: 77, Issue:3 | NF-κB inhibitors from Eurycoma longifolia. |
| AID338762 | Cytotoxicity against human melanoma cells | |||
| 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 |
| AID338764 | Cytotoxicity against human breast cancer cells | |||
| AID338760 | Cytotoxicity against human KBV1 cells | |||
| 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 |
| AID338765 | Cytotoxicity against human colon cancer cells | |||
| 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. |
| AID338766 | Cytotoxicity against mouse P388 cells | |||
| 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 |
| 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. |
| 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 |
| AID1070420 | Growth 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 staining | 2014 | Journal of natural products, Mar-28, Volume: 77, Issue:3 | NF-κB inhibitors from Eurycoma longifolia. |
| AID338759 | Cytotoxicity against human KB cells | |||
| 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. |
| AID338761 | Cytotoxicity against human fibrosarcoma cells | |||
| 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 |
| 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 |
| 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 |
| AID338763 | Cytotoxicity against human lung cancer cells | |||
| AID1070422 | Inhibition 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 assay | 2014 | Journal of natural products, Mar-28, Volume: 77, Issue:3 | NF-κB inhibitors from Eurycoma longifolia. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 5 (38.46) | 29.6817 |
| 2010's | 5 (38.46) | 24.3611 |
| 2020's | 3 (23.08) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (11.94) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 14 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||