Detailed information for compound 1493721

Basic information

Technical information
  • TDR Targets ID: 1493721
  • Name: (3E)-3-[5-(5-hydroxy-1H-indol-3-yl)-2-oxo-1H- pyrrol-3-ylidene]-1H-indol-2-one
  • MW: 343.336 | Formula: C20H13N3O3
  • H donors: 4 H acceptors: 3 LogP: 1.88 Rotable bonds: 1
    Rule of 5 violations (Lipinski): 1
  • SMILES: Oc1ccc2c(c1)c(c[nH]2)C1=C/C(=C/2\C(=O)Nc3c2cccc3)/C(=O)N1
  • InChi: 1S/C20H13N3O3/c24-10-5-6-15-12(7-10)14(9-21-15)17-8-13(19(25)23-17)18-11-3-1-2-4-16(11)22-20(18)26/h1-9,21,24H,(H,22,26)(H,23,25)/b18-13+
  • InChiKey: XAPNKXIRQFHCHN-QGOAFFKASA-N  


Substructure search Similarity search

Network

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Synonyms

  • (3E)-3-[5-(5-hydroxy-1H-indol-3-yl)-2-oxo-1H-pyrrol-3-ylidene]indolin-2-one
  • (3E)-3-[5-(5-hydroxy-1H-indol-3-yl)-2-oxo-1H-pyrrol-3-ylidene]-2-indolinone
  • (3E)-3-[5-(5-hydroxy-1H-indol-3-yl)-2-keto-2-pyrrolin-3-ylidene]oxindole
  • NChemBio.2007.20-comp21

Targets

Known targets for this compound

No curated genes were found associated with this compound

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
Mycobacterium ulcerans hypothetical protein 0.0024 0.1149 1
Entamoeba histolytica acyl-CoA synthetase, putative 0.0024 0.1149 0.5
Mycobacterium tuberculosis Probable fatty-acid-CoA ligase FadD2 (fatty-acid-CoA synthetase) (fatty-acid-CoA synthase) 0.0024 0.1149 1
Loa Loa (eye worm) bromodomain containing protein 0.0018 0.0106 0.0114
Brugia malayi Bromodomain containing protein 0.0038 0.3667 0.2845
Chlamydia trachomatis acylglycerophosphoethanolamine acyltransferase 0.0018 0.0114 0.5
Mycobacterium ulcerans long-chain-fatty-acid-CoA ligase 0.0024 0.1149 1
Onchocerca volvulus 0.0024 0.1149 0.5
Schistosoma mansoni bromodomain containing protein 0.0063 0.7978 1
Echinococcus multilocularis fetal alzheimer antigen, falz 0.0022 0.0947 0.1287
Loa Loa (eye worm) hypothetical protein 0.0018 0.0114 0.0123
Loa Loa (eye worm) hypothetical protein 0.0041 0.4087 0.4413
Echinococcus granulosus bromodomain adjacent to zinc finger domain 0.0036 0.3258 0.4427
Echinococcus granulosus bromodomain adjacent to zinc finger domain 0.006 0.736 1
Loa Loa (eye worm) hypothetical protein 0.0018 0.0114 0.0123
Plasmodium falciparum acyl-CoA synthetase 0.0018 0.0114 0.5
Mycobacterium ulcerans acyl-CoA synthetase 0.0024 0.1149 1
Mycobacterium tuberculosis Probable chain -fatty-acid-CoA ligase FadD13 (fatty-acyl-CoA synthetase) 0.0024 0.1149 1
Leishmania major 4-coumarate:coa ligase-like protein 0.0024 0.1149 0.5
Loa Loa (eye worm) hypothetical protein 0.0018 0.0114 0.0123
Leishmania major 4-coumarate:coa ligase-like protein 0.0024 0.1149 0.5
Brugia malayi PHD-finger family protein 0.0025 0.1356 0.0234
Mycobacterium ulcerans acyl-CoA synthetase 0.0024 0.1149 1
Loa Loa (eye worm) hypothetical protein 0.0038 0.3679 0.3972
Loa Loa (eye worm) PHD-finger family protein 0.0021 0.0618 0.0667
Loa Loa (eye worm) hypothetical protein 0.0071 0.9262 1
Schistosoma mansoni hypothetical protein 0.0021 0.0618 0.0774
Echinococcus multilocularis bromodomain adjacent to zinc finger domain 0.006 0.736 1
Echinococcus multilocularis bromodomain adjacent to zinc finger domain 0.0036 0.3258 0.4427
Loa Loa (eye worm) hypothetical protein 0.0024 0.1149 0.124
Echinococcus multilocularis zinc finger protein 0.002 0.0435 0.0592
Loa Loa (eye worm) hypothetical protein 0.0018 0.0114 0.0123
Schistosoma mansoni zinc finger protein 0.002 0.0435 0.0546
Mycobacterium ulcerans long-chain-fatty-acid--CoA ligase 0.0024 0.1149 1
Loa Loa (eye worm) hypothetical protein 0.0024 0.1149 0.124
Echinococcus granulosus fetal alzheimer antigen falz 0.0022 0.0947 0.1287
Loa Loa (eye worm) hypothetical protein 0.0024 0.1149 0.124
Loa Loa (eye worm) hypothetical protein 0.0018 0.0114 0.0123
Entamoeba histolytica acyl-CoA synthetase, putative 0.0024 0.1149 0.5
Entamoeba histolytica acyl-coA synthetase, putative 0.0024 0.1149 0.5
Echinococcus granulosus zinc finger protein 0.002 0.0435 0.0592
Schistosoma mansoni acetyl-CoA C-acetyltransferase 0.0022 0.0947 0.1188
Mycobacterium ulcerans acyl-CoA synthetase 0.0024 0.1149 1
Loa Loa (eye worm) hypothetical protein 0.0043 0.4417 0.4769
Plasmodium vivax acyl-CoA synthetase, putative 0.0018 0.0114 0.5
Mycobacterium ulcerans fatty-acid-CoA ligase 0.0024 0.1149 1
Mycobacterium leprae PROBABLE FATTY-ACID-CoA LIGASE FADD2 (FATTY-ACID-CoA SYNTHETASE) (FATTY-ACID-CoA SYNTHASE) 0.0024 0.1149 0.5
Mycobacterium leprae PROBABLE FATTY-ACID-CoA LIGASE FADD7 (FATTY-ACID-CoA SYNTHETASE) (FATTY-ACID-CoA SYNTHASE) 0.0024 0.1149 0.5
Mycobacterium ulcerans long-chain fatty-acid CoA ligase 0.0024 0.1149 1
Leishmania major 4-coumarate:coa ligase-like protein 0.0024 0.1149 0.5

Activities

Activity type Activity value Assay description Source Reference
GI50 (functional) = 0.03 uM Cytotoxicity against Homo sapiens (human) KM12 cells ChEMBL. No reference
IC50 (functional) = 0.63 uM Antimalarial activity against chloroquine-resistant Plasmodium falciparum S20 infected in erythrocytes after 48 hrs by [3H]hypoxanthine incorporation assay ChEMBL. 19273690
IC50 (functional) = 0.85 uM Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 infected in erythrocytes after 48 hrs by [3H]hypoxanthine incorporation assay ChEMBL. 19273690
IC50 (ADMET) = 2.2 uM Cytotoxicity against Homo sapiens (human) Hep2 cells ChEMBL. No reference
Inhibition (functional) Antimalarial activity against Plasmodium falciparum young blood forms (0 to 24 hrs ring stage) infected in erythrocytes after 24 hrs by [3H]hypoxanthine incorporation assay ChEMBL. 19273690
Inhibition (functional) Antimalarial activity against Plasmodium falciparum mature blood forms (24 to 48 hrs ring stage) infected in erythrocytes after 24 hrs by [3H]hypoxanthine incorporation assay ChEMBL. 19273690
Inhibition (functional) = 3.58 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 0.75 mg/kg/day, ip administered 1 hr post-infection and measured on day 5 post-infection ChEMBL. 19273690
Inhibition (functional) = 4 % Antitrypanosomal activity against trypomastigote of Trypanosoma cruzi Y infected in albino mouse assessed as reduction in parasitemia at 100 mg/kg, ip for 7 days ChEMBL. No reference
Inhibition (functional) = 12.04 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 0.075 mg/kg/day, ip administered 1 hr post-infection and measured on day 8 post-infection ChEMBL. 19273690
Inhibition (functional) = 20.42 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 0.75 mg/kg/day, ip administered 1 hr post-infection and measured on day 6 post-infection ChEMBL. 19273690
Inhibition (functional) = 33.23 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 3.75 mg/kg/day, ip administered 1 hr post-infection and measured on day 5 post-infection ChEMBL. 19273690
Inhibition (functional) = 39.25 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 0.75 mg/kg/day, ip administered 1 hr post-infection and measured on day 7 post-infection ChEMBL. 19273690
Inhibition (functional) = 48.85 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 0.75 mg/kg/day, ip administered 1 hr post-infection and measured on day 8 post-infection ChEMBL. 19273690
Inhibition (functional) = 50.1 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 7.5 mg/kg/day, ip administered 5 days post-infection and measured on day 7 post-infection ChEMBL. 19273690
Inhibition (functional) = 56.48 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 7.5 mg/kg/day, ip administered 1 hr post-infection and measured on day 5 post-infection ChEMBL. 19273690
Inhibition (functional) = 59 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed inhibition of parasitemia at 7.5 mg/kg/day, ip for 10 days followed by compound withdrawal and measured on day 16 post-infection ChEMBL. 19273690
Inhibition (functional) = 64.89 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 3.75 mg/kg/day, ip administered 1 hr post-infection and measured on day 6 post-infection ChEMBL. 19273690
Inhibition (functional) = 75.4 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 7.5 mg/kg/day, ip administered 1 hr post-infection and measured on day 6 post-infection ChEMBL. 19273690
Inhibition (functional) = 75.73 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 3.75 mg/kg/day, ip administered 1 hr post-infection and measured on day 8 post-infection ChEMBL. 19273690
Inhibition (functional) = 82.12 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 3.75 mg/kg/day, ip administered 1 hr post-infection and measured on day 7 post-infection ChEMBL. 19273690
Inhibition (functional) = 84.67 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 7.5 mg/kg/day, ip administered 1 hr post-infection and measured on day 8 post-infection ChEMBL. 19273690
Inhibition (functional) = 85 % Inhibition of HCl/ethanol- induced gastric damage in Mus musculus (mouse) at 10 mg/kg, po, sd ChEMBL. No reference
Inhibition (functional) = 86.9 % Antimalarial activity against nonlethal Plasmodium chabaudi chabaudi AS infected in C57BL/6 mouse assessed as inhibition of parasitemia at 7.5 mg/kg/day, ip administered 1 hr post-infection and measured on day 7 post-infection ChEMBL. 19273690
MBC (functional) = 128 ug ml-1 Antimycobacterial activity against Mycobacterium tuberculosis H37Rv LITERATURE. No reference
MIC (functional) = 64 ug ml-1 Antimycobacterial activity against Mycobacterium tuberculosis H37Rv LITERATURE. No reference
Survival (functional) = 10 % Antimalarial activity against lethal Plasmodium chabaudi chabaudi AJ infected in C57BL/6 mouse assessed as mouse survival rate at 7.5 mg/kg/day, ip administered 1 hr post-infection and measured on day 9 post-infection ChEMBL. 19273690
Survival (functional) = 14 % Antimalarial activity against lethal Plasmodium chabaudi chabaudi AJ infected in C57BL/6 mouse assessed as mouse survival rate at 7.5 mg/kg/day, ip administered 1 hr post-infection and measured on day 14 post-infection ChEMBL. 19273690
Survival (functional) = 80 % Antimalarial activity against lethal Plasmodium chabaudi chabaudi AJ infected in C57BL/6 mouse assessed as mouse survival rate at 7.5 mg/kg/day, ip administered 1 hr post-infection and measured on day 16 post-infection ChEMBL. 19273690

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23
Plasmodium falciparum ChEMBL23 19273690

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.
 
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External resources for this compound

Bibliographic References

No literature references available for this target.

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