Detailed information for compound 343288

Basic information

Technical information
  • TDR Targets ID: 343288
  • Name: ethyl (Z)-4-(1-benzyl-5-methoxyindol-3-yl)-4- hydroxy-2-oxobut-3-enoate
  • MW: 379.406 | Formula: C22H21NO5
  • H donors: 1 H acceptors: 3 LogP: 4.08 Rotable bonds: 8
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCOC(=O)C(=O)/C=C(/c1cn(c2c1cc(OC)cc2)Cc1ccccc1)\O
  • InChi: 1S/C22H21NO5/c1-3-28-22(26)21(25)12-20(24)18-14-23(13-15-7-5-4-6-8-15)19-10-9-16(27-2)11-17(18)19/h4-12,14,24H,3,13H2,1-2H3/b20-12-
  • InChiKey: YHOHWUVBNQQPKE-NDENLUEZSA-N  

Network

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Synonyms

  • ethyl (Z)-4-(1-benzyl-5-methoxy-indol-3-yl)-4-hydroxy-2-oxo-but-3-enoate
  • (Z)-4-(1-benzyl-5-methoxy-3-indolyl)-4-hydroxy-2-oxo-3-butenoic acid ethyl ester
  • ethyl (Z)-4-hydroxy-4-[5-methoxy-1-(phenylmethyl)indol-3-yl]-2-oxo-but-3-enoate
  • (Z)-4-(1-benzyl-5-methoxy-indol-3-yl)-4-hydroxy-2-keto-but-3-enoic acid ethyl ester

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 integrase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Trypanosoma brucei RNA helicase, putative Get druggable targets OG5_139608 All targets in OG5_139608
Plasmodium yoelii integrase-related Get druggable targets OG5_139608 All targets in OG5_139608
Trypanosoma congolense RNA helicase, putative Get druggable targets OG5_139608 All targets in OG5_139608
Schistosoma mansoni hypothetical protein Get druggable targets OG5_139608 All targets in OG5_139608

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
Mycobacterium tuberculosis Probable thymidylate synthase ThyA (ts) (TSASE) 0.074 0.0961 0.0961
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.2604 0.5579 0.5
Leishmania major dihydrofolate reductase-thymidylate synthase 0.2604 0.5579 0.5
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.4389 1 1
Echinococcus granulosus dihydrofolate reductase 0.4389 1 1
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.2604 0.5579 0.5
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.4389 1 1
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.2604 0.5579 0.5
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.4389 1 1
Brugia malayi thymidylate synthase 0.074 0.0961 0.0961
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.2604 0.5579 1
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.2604 0.5579 0.5
Schistosoma mansoni dihydrofolate reductase 0.4389 1 1
Echinococcus multilocularis dihydrofolate reductase 0.4389 1 1
Chlamydia trachomatis dihydrofolate reductase 0.4389 1 0.5
Loa Loa (eye worm) dihydrofolate reductase 0.4389 1 1
Trichomonas vaginalis conserved hypothetical protein 0.0352 0 0.5
Onchocerca volvulus 0.074 0.0961 0.5
Brugia malayi Dihydrofolate reductase 0.4389 1 1

Activities

Activity type Activity value Assay description Source Reference
CC50 (functional) = 29.04 uM Cytotoxic concentration required to reduce MT-4 cell viability ChEMBL. 16250669
CC50 (functional) = 29.04 uM Cytotoxic concentration required to reduce MT-4 cell viability ChEMBL. 16250669
EC50 (functional) = 6.07 uM Effective concentration required to reduce HIV-1-induced cytopathic effect in MT-4 cells ChEMBL. 16250669
IC50 (binding) = 0.15 uM In vitro concentration required to inhibit the overall HIV-1 integrase strand transfer ChEMBL. 16250669
IC50 (binding) = 0.15 uM In vitro concentration required to inhibit the overall HIV-1 integrase strand transfer ChEMBL. 16250669
IC50 (binding) = 0.68 uM In vitro concentration required to inhibit the HIV-1 integrase strand transfer ChEMBL. 16250669
IC50 (binding) = 0.68 uM In vitro concentration required to inhibit the HIV-1 integrase strand transfer ChEMBL. 16250669
IC50 (binding) = 162.5 uM In vitro concentration required to inhibit the HIV-1 integrase 3' strand transfer ChEMBL. 16250669
IC50 (binding) = 162.5 uM In vitro concentration required to inhibit the HIV-1 integrase 3' strand transfer ChEMBL. 16250669
Selectivity index (functional) = 5 uM Selectivity index was measured by the ratio of CC50/EC50 ChEMBL. 16250669
Selectivity index (functional) = 5 uM Selectivity index was measured by the ratio of CC50/EC50 ChEMBL. 16250669

Phenotypes

Whole-cell/tissue/organism interactions

We have no records of whole-cell/tissue assays done with this compound What does this mean?

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.

External resources for this compound

Bibliographic References

1 literature reference was collected for this gene.

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