Detailed information for compound 422661
Basic information
Technical information
- TDR Targets ID: 422661
- Name: 3-hydroxy-8-methoxy-9-methyl-5,6-dihydrobenzo [b][1]benzoxepine-7,10-dione
- MW: 286.279 | Formula: C16H14O5
-
H donors: 1
H acceptors: 3
LogP: 2.27
Rotable bonds: 1
Rule of 5 violations (Lipinski): 1 - SMILES: COC1=C(C)C(=O)C2=C(C1=O)CCc1c(O2)ccc(c1)O
- InChi: 1S/C16H14O5/c1-8-13(18)16-11(14(19)15(8)20-2)5-3-9-7-10(17)4-6-12(9)21-16/h4,6-7,17H,3,5H2,1-2H3
- InChiKey: ATBQBNKWWGOEFJ-UHFFFAOYSA-N
Network
Hover on a compound node to display the structore
Synonyms
- 3-hydroxy-8-methoxy-9-methyl-5,6-dihydrobenzo[b][1]benzoxepine-7,10-quinone
Targets
Known targets for this compound
| Species | Target name | Source | Bibliographic reference |
|---|---|---|---|
| Homo sapiens | prostaglandin-endoperoxide synthase 2 (prostaglandin G/H synthase and cyclooxygenase) | Starlite/ChEMBL | References |
Predicted pathogen targets for this compound
By orthology
No druggable targets predicted by orthology data
By sequence similarity to non orthologous known druggable targets
No druggable targets predicted by sequence similarity
Obtained from network model
Ranking Plot
Putative Targets List
| Species | Potential target | Raw | Global | Species |
|---|---|---|---|---|
| Loa Loa (eye worm) | hypothetical protein | 0.0057 | 1 | 1 |
| Echinococcus multilocularis | ecdysone induced protein 78C | 0.0057 | 1 | 1 |
| Schistosoma mansoni | retinoic acid receptor RXR | 0.00572278 | 1 | 1 |
| Echinococcus granulosus | nuclear receptor 2DBD gamma | 0.0057 | 1 | 1 |
| Echinococcus multilocularis | nuclear receptor 2DBD gamma | 0.0057 | 1 | 1 |
| Schistosoma mansoni | thyroid hormone receptor | 0.00572278 | 1 | 1 |
| Onchocerca volvulus | Bile acid receptor homolog | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-41 | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-31 | 0.00572278 | 1 | 1 |
| Echinococcus multilocularis | FTZ F1 alpha | 0.0057 | 1 | 1 |
| Echinococcus granulosus | FTZ F1 alpha | 0.00572278 | 1 | 1 |
| Brugia malayi | Ligand-binding domain of nuclear hormone receptor family protein | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | coup transcription factor | 0.00572278 | 1 | 1 |
| Echinococcus granulosus | nuclear receptor 2DBD gamma | 0.00572278 | 1 | 1 |
| Brugia malayi | nuclear receptor NHR-88 | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-31 | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-19 | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-14 | 0.00572278 | 1 | 1 |
| Brugia malayi | steroid hormone receptor | 0.00572278 | 1 | 1 |
| Echinococcus granulosus | hepatocyte nuclear factor 4 alpha | 0.00572278 | 1 | 1 |
| Echinococcus granulosus | retinoic acid receptor rxr beta a | 0.0057 | 1 | 1 |
| Echinococcus granulosus | hepatocyte nuclear factor 4 alpha | 0.0057 | 1 | 1 |
| Echinococcus granulosus | COUP TF:Svp nuclear hormone receptor | 0.00572278 | 1 | 1 |
| Echinococcus multilocularis | hepatocyte nuclear factor 4 alpha | 0.0057 | 1 | 1 |
| Schistosoma mansoni | thyroid hormone receptor | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | steroid hormone receptor ad4bp | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-3 | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.00572278 | 1 | 1 |
| Echinococcus multilocularis | nuclear receptor 2DBD gamma | 0.00572278 | 1 | 1 |
| Brugia malayi | Steroid receptor seven-up type 2 | 0.00572278 | 1 | 1 |
| Brugia malayi | Ligand-binding domain of nuclear hormone receptor family protein | 0.0057 | 1 | 1 |
| Echinococcus multilocularis | FTZ F1 alpha | 0.00572278 | 1 | 1 |
| Brugia malayi | Ligand-binding domain of nuclear hormone receptor family protein | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | nuclear Hormone Receptor family member | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-25 | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-40 | 0.00572278 | 1 | 1 |
| Echinococcus granulosus | ecdysone induced protein 78C | 0.00572278 | 1 | 1 |
| Echinococcus multilocularis | nuclear receptor 2DBD gamma | 0.00572278 | 1 | 1 |
| Brugia malayi | ecdysteroid receptor | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.0057 | 1 | 1 |
| Schistosoma mansoni | retinoid-x-receptor (RXR) | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-3 | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-1 | 0.0057 | 1 | 1 |
| Onchocerca volvulus | Protein ultraspiracle homolog | 0.0057 | 1 | 1 |
| Brugia malayi | photoreceptor-specific nuclear receptor | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-25 | 0.00572278 | 1 | 1 |
| Onchocerca volvulus | Steroid hormone receptor family member cnr14 homolog | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-49 | 0.0057 | 1 | 1 |
| Echinococcus multilocularis | ecdysone induced protein 78C | 0.00572278 | 1 | 1 |
| Echinococcus multilocularis | nuclear receptor 2DBD gamma | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.0057 | 1 | 1 |
| Schistosoma mansoni | RAR-like nuclear receptor | 0.0057 | 1 | 1 |
| Schistosoma mansoni | nuclear receptor 2DBD-gamma | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-31 | 0.00572278 | 1 | 1 |
| Onchocerca volvulus | 0.0057 | 1 | 1 | |
| Brugia malayi | nuclear hormone receptor | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | nuclear hormone receptor nor-1/nor-2 | 0.0057 | 1 | 1 |
| Brugia malayi | nuclear hormone receptor | 0.0057 | 1 | 1 |
| Onchocerca volvulus | Bile acid receptor homolog | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | nuclear Hormone Receptor family member | 0.0057 | 1 | 1 |
| Schistosoma mansoni | coup transcription factor | 0.0057 | 1 | 1 |
| Echinococcus granulosus | ecdysone induced protein 78C | 0.0057 | 1 | 1 |
| Onchocerca volvulus | 0.00572278 | 1 | 1 | |
| Echinococcus multilocularis | FTZ F1 nuclear receptor protein | 0.0057 | 1 | 1 |
| Echinococcus multilocularis | COUP TF:Svp nuclear hormone receptor | 0.0057 | 1 | 1 |
| Brugia malayi | Steroid receptor seven-up type 2 | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-1 | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-40 | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.0057 | 1 | 1 |
| Echinococcus granulosus | retinoic acid receptor rxr beta a | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-41 | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.0057 | 1 | 1 |
| Schistosoma mansoni | nuclear hormone receptor nor-1/nor-2 | 0.00572278 | 1 | 1 |
| Echinococcus multilocularis | thyroid hormone receptor alpha | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-41 | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-49 | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | steroid hormone receptor | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | steroid hormone receptor ad4bp | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-25 | 0.0057 | 1 | 1 |
| Echinococcus granulosus | FTZ F1 nuclear receptor protein | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-14 | 0.00572278 | 1 | 1 |
| Echinococcus granulosus | COUP TF:Svp nuclear hormone receptor | 0.0057 | 1 | 1 |
| Echinococcus multilocularis | thyroid hormone receptor alpha | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-19 | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | Tr4/Tr2 (homologue) | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-1 | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-14 | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | steroid hormone receptor | 0.0057 | 1 | 1 |
| Echinococcus granulosus | FTZ F1 nuclear receptor protein | 0.0057 | 1 | 1 |
| Echinococcus multilocularis | COUP TF:Svp nuclear hormone receptor | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | nuclear hormone receptor | 0.00572278 | 1 | 1 |
| Brugia malayi | nuclear receptor NHR-88 | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-31 | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor-like 1 | 0.00572278 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-14 | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-19 | 0.0057 | 1 | 1 |
| Echinococcus granulosus | FTZ F1 alpha | 0.0057 | 1 | 1 |
| Schistosoma mansoni | nuclear receptor 2DBD-gamma | 0.00572278 | 1 | 1 |
| Echinococcus multilocularis | hepatocyte nuclear factor 4 alpha | 0.00572278 | 1 | 1 |
| Echinococcus granulosus | Nuclear hormone receptor family member nhr 41 | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.0057 | 1 | 1 |
| Onchocerca volvulus | Steroid hormone receptor family member cnr14 homolog | 0.00572278 | 1 | 1 |
| Echinococcus granulosus | nuclear receptor 2DBD gamma | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.00572278 | 1 | 1 |
| Brugia malayi | Ligand-binding domain of nuclear hormone receptor family protein | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-40 | 0.0057 | 1 | 1 |
| Schistosoma mansoni | FTZ-F1 nuclear receptor-like protein | 0.00572278 | 1 | 1 |
| Echinococcus granulosus | Nuclear hormone receptor family member nhr 41 | 0.0057 | 1 | 1 |
| Brugia malayi | steroid hormone receptor | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor-like 1 | 0.0057 | 1 | 1 |
| Schistosoma mansoni | thyroid hormone receptor | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-19 | 0.0057 | 1 | 1 |
| Onchocerca volvulus | Protein ultraspiracle homolog | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | retinoid-x-receptor (RXR) | 0.0057 | 1 | 1 |
| Echinococcus multilocularis | FTZ F1 nuclear receptor protein | 0.00572278 | 1 | 1 |
| Brugia malayi | photoreceptor-specific nuclear receptor | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-25 | 0.00572278 | 1 | 1 |
| Echinococcus multilocularis | Nuclear hormone receptor family member nhr 41 | 0.0057 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | thyroid hormone receptor | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.0057 | 1 | 1 |
| Schistosoma mansoni | Tr4/Tr2 (homologue) | 0.0057 | 1 | 1 |
| Schistosoma mansoni | RAR-like nuclear receptor | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | photoreceptor-specific nuclear receptor related | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-1 | 0.0057 | 1 | 1 |
| Schistosoma mansoni | retinoic acid receptor RXR | 0.0057 | 1 | 1 |
| Echinococcus granulosus | nuclear receptor 2DBD gamma | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-49 | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | FTZ-F1 nuclear receptor-like protein | 0.0057 | 1 | 1 |
| Schistosoma mansoni | photoreceptor-specific nuclear receptor related | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-41 | 0.0057 | 1 | 1 |
| Echinococcus multilocularis | Nuclear hormone receptor family member nhr 41 | 0.00572278 | 1 | 1 |
| Loa Loa (eye worm) | nuclear hormone receptor family member nhr-49 | 0.00572278 | 1 | 1 |
| Schistosoma mansoni | nuclear hormone receptor | 0.0057 | 1 | 1 |
| Brugia malayi | Nuclear hormone receptor family member nhr-40 | 0.0057 | 1 | 1 |
Activities
| Activity type | Activity value | Assay description | Source | Reference |
|---|---|---|---|---|
| IC50 (binding) | = 10.1 uM | Inhibition of COX2 by radioimmunoassay method | ChEMBL. | 17480099 |
| IC50 (binding) | = 10.1 uM | Inhibition of COX2 by radioimmunoassay method | ChEMBL. | 17480099 |
| IC50 (functional) | = 10.5 uM | Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 by microculture radioisotope technique | ChEMBL. | 17480099 |
| IC50 (functional) | = 10.5 uM | Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 by microculture radioisotope technique | ChEMBL. | 17480099 |
| IC50 (binding) | > 34.9 uM | Inhibition of COX1 by radioimmunoassay method | ChEMBL. | 17480099 |
| IC50 (binding) | > 34.9 uM | Inhibition of COX1 by radioimmunoassay method | ChEMBL. | 17480099 |
| IC50 (ADMET) | = 38.8 uM | Cytotoxicity against KB cells by colorimetric method | ChEMBL. | 17480099 |
| IC50 (ADMET) | = 38.8 uM | Cytotoxicity against KB cells by colorimetric method | ChEMBL. | 17480099 |
| IC50 (ADMET) | = 41.9 uM | Cytotoxicity against BC cells by colorimetric method | ChEMBL. | 17480099 |
| IC50 (functional) | > 174.8 uM | Antifungal activity against Candida albicans by colorimetric method | ChEMBL. | 17480099 |
| IC50 (functional) | > 174.8 uM | Antifungal activity against Candida albicans by colorimetric method | ChEMBL. | 17480099 |
| MIC (functional) | = 174.8 uM | Antimycobacterial activity against Mycobacterium tuberculosis H37Ra by microplate Alamar Blue assay | ChEMBL. | 17480099 |
| MIC (functional) | = 174.8 uM | Antimycobacterial activity against Mycobacterium tuberculosis H37Ra by microplate Alamar Blue assay | ChEMBL. | 17480099 |
Phenotypes
Whole-cell/tissue/organism interactions
| Species name | Source | Reference | Is orphan |
|---|---|---|---|
| Plasmodium falciparum | ChEMBL23 | 17480099 |
Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.
Annotated phenotypes:
We have no manually annotated phenotypes for this drug.
What does this mean? / Care to help?
In TDR Targets, information about phenotypes that are caused by
drugs, or by genetic manipulation of cells (e.g. gene knockouts or
knockdowns) is manually curated from the literature. These
descriptions help to describe the potential of the target for drug
development. If no information is available for this gene or if the
information is incomplete, this may mean that i) the papers
containing this information either appeared after the curation
effort for this organism was carried out or they were inadvertently
missed by curators; or that ii) the curation effort for this
organism has not yet started.
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.
External resources for this compound
- ChEMBL: CHEMBL389398
- PubChem: 16679966
Bibliographic References
1 literature reference was collected for this gene.
If you have references for this compound, please enter them in a user comment (below) or Contact us.