TDR Targets

Basic information

Technical information

TDR Targets ID: 1659594
Name: N-[2-(3,4-dihydroxyphenyl)ethyl]-5,6-dihydrox y-1H-indole-2-carboxamide
MW: 328.319 | Formula: C17H16N2O5
H donors: 6 H acceptors: 5 LogP: 2.19 Rotable bonds: 5
Rule of 5 violations (Lipinski): 2
SMILES: Oc1cc(CCNC(=O)c2[nH]c3c(c2)cc(c(c3)O)O)ccc1O
InChi: 1S/C17H16N2O5/c20-13-2-1-9(5-14(13)21)3-4-18-17(24)12-6-10-7-15(22)16(23)8-11(10)19-12/h1-2,5-8,19-23H,3-4H2,(H,18,24)
InChiKey: TUBOBKVJOSIWIU-UHFFFAOYSA-N

Network

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Target Layer

Model Organisms

Species	Viewmode
Arabidopsis thaliana
Caenorhabditis elegans
Dictyostelium discoideum
Drosophila melanogaster
Escherichia coli
Homo sapiens
Mus musculus
Oryza sativa
Saccharomyces cerevisiae
Schmidtea mediterranea
Other organisms

TDR Pathogens:

Species	Viewmode
Brugia malayi
Chlamydia trachomatis
Echinococcus granulosus
Entamoeba histolytica
Echinococcus multilocularis
Giardia lamblia
Leishmania major
Loa Loa (eye worm)
Mycobacterium leprae
Mycobacterium tuberculosis
Mycobacterium ulcerans
Onchocerca volvulus
Plasmodium falciparum
Plasmodium vivax
Schistosoma mansoni
Trypanosoma brucei
Trypanosoma cruzi
Toxoplasma gondii
Treponema pallidum
Trichomonas vaginalis
Wolbachia endosymbiont of Brugia malayi

Other Pathogens:

Species	Viewmode
Babesia bovis
Candida albicans
Cryptosporidium hominis
Cryptosporidium parvum
Leishmania braziliensis
Leishmania donovani
Leishmania infantum
Leishmania mexicana
Neospora caninum
Plasmodium berghei
Plasmodium knowlesi
Plasmodium yoelii
Schistosoma japonicum
Trypanosoma brucei gambiense
Trypanosoma congolense
Theileria parva

Compound Layer

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Clustering layers

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Synonyms

AIDS356391
1H-Indole-2-carboxamide, 5,6-dihydroxy-N-[(3,4-dihydroxy)phenylethyl]-
AIDS-356391

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	carbonic anhydrase II	Starlite/ChEMBL	References
Homo sapiens	carbonic anhydrase IX	Starlite/ChEMBL	References
Homo sapiens	carbonic anhydrase XII	Starlite/ChEMBL	References
Influenza A virus (strain A/X-31 H3N2)	Polymerase acidic protein	Starlite/ChEMBL	References
Homo sapiens	carbonic anhydrase I	Starlite/ChEMBL	References

Predicted pathogen targets for this compound

By orthology

Species	Potential target	Known druggable target/s	Ortholog Group
Trypanosoma cruzi	carbonic anhydrase-like protein, putative	Get druggable targets OG5_127628	All targets in OG5_127628
Echinococcus multilocularis	carbonic anhydrase II	Get druggable targets OG5_127628	All targets in OG5_127628
Trypanosoma congolense	carbonic anhydrase-like protein	Get druggable targets OG5_127628	All targets in OG5_127628
Leishmania braziliensis	carbonic anhydrase-like protein	Get druggable targets OG5_127628	All targets in OG5_127628
Leishmania donovani	carbonic anhydrase-like protein	Get druggable targets OG5_127628	All targets in OG5_127628
Leishmania major	carbonic anhydrase-like protein	Get druggable targets OG5_127628	All targets in OG5_127628
Brugia malayi	Eukaryotic-type carbonic anhydrase family protein	Get druggable targets OG5_127628	All targets in OG5_127628
Schistosoma japonicum	ko:K01672 carbonic anhydrase [EC4.2.1.1], putative	Get druggable targets OG5_127628	All targets in OG5_127628
Schistosoma mansoni	carbonic anhydrase II (carbonate dehydratase II)	Get druggable targets OG5_127628	All targets in OG5_127628
Trypanosoma brucei gambiense	carbonic anhydrase-like protein	Get druggable targets OG5_127628	All targets in OG5_127628
Echinococcus granulosus	carbonic anhydrase II	Get druggable targets OG5_127628	All targets in OG5_127628
Trypanosoma brucei	carbonic anhydrase-like protein	Get druggable targets OG5_127628	All targets in OG5_127628
Leishmania mexicana	carbonic anhydrase-like protein	Get druggable targets OG5_127628	All targets in OG5_127628
Brugia malayi	Putative carbonic anhydrase 5 precursor	Get druggable targets OG5_127628	All targets in OG5_127628
Loa Loa (eye worm)	eukaryotic-type carbonic anhydrase	Get druggable targets OG5_127628	All targets in OG5_127628
Leishmania infantum	carbonic anhydrase-like protein	Get druggable targets OG5_127628	All targets in OG5_127628
Loa Loa (eye worm)	carbonic anhydrase 3	Get druggable targets OG5_127628	All targets in OG5_127628
Schistosoma mansoni	carbonic anhydrase II (carbonate dehydratase II)	Get druggable targets OG5_127628	All targets in OG5_127628
Trypanosoma cruzi	carbonic anhydrase-like protein, putative	Get druggable targets OG5_127628	All targets in OG5_127628
Trypanosoma congolense	carbonic anhydrase-like protein	Get druggable targets OG5_127628	All targets in OG5_127628

By sequence similarity to non orthologous known druggable targets

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Trypanosoma brucei	carbonic anhydrase-like protein	carbonic anhydrase I	261 aa	281 aa	25.3 %
Brugia malayi	Carbonic anhydrase like protein 2 precursor	carbonic anhydrase II	260 aa	259 aa	32.0 %
Trypanosoma cruzi	carbonic anhydrase-like protein, putative	carbonic anhydrase XII	354 aa	295 aa	23.1 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Brugia malayi	calcium-independent alpha-latrotoxin receptor 2, putative	0.0066	0.0558	0.0696
Toxoplasma gondii	hypothetical protein	0.0134	0.3136	1
Echinococcus multilocularis	survival motor neuron protein 1	0.0263	0.8011	1
Leishmania major	carbonic anhydrase-like protein	0.0248	0.7445	0.7445
Loa Loa (eye worm)	hypothetical protein	0.0128	0.2895	0.3614
Loa Loa (eye worm)	hypothetical protein	0.0128	0.2895	0.3614
Echinococcus granulosus	carbonic anhydrase II	0.0248	0.7445	0.9239
Schistosoma mansoni	hypothetical protein	0.0066	0.0558	0.0651
Schistosoma mansoni	tar DNA-binding protein	0.0137	0.3223	0.4269
Brugia malayi	hypothetical protein	0.0128	0.2895	0.3614
Onchocerca volvulus	Huntingtin homolog	0.0128	0.2895	1
Leishmania major	mitochondrial DNA polymerase beta-PAK, putative	0.0149	0.3703	0.3703
Loa Loa (eye worm)	latrophilin receptor protein 2	0.0066	0.0558	0.0696
Loa Loa (eye worm)	hypothetical protein	0.0209	0.5984	0.747
Schistosoma mansoni	hypothetical protein	0.0143	0.3473	0.4608
Loa Loa (eye worm)	TAR-binding protein	0.0137	0.3223	0.4023
Brugia malayi	Putative carbonic anhydrase 5 precursor	0.0248	0.7445	0.9292
Schistosoma mansoni	carbonic anhydrase-related	0.0134	0.3136	0.415
Schistosoma mansoni	carbonic anhydrase-related	0.0134	0.3136	0.415
Schistosoma mansoni	tar DNA-binding protein	0.0137	0.3223	0.4269
Schistosoma mansoni	carbonic anhydrase-related	0.0134	0.3136	0.415
Echinococcus granulosus	carbonic anhydrase	0.0134	0.3136	0.3459
Brugia malayi	Eukaryotic-type carbonic anhydrase family protein	0.0248	0.7445	0.9292
Echinococcus multilocularis	carbonic anhydrase	0.0134	0.3136	0.3459
Schistosoma mansoni	carbonic anhydrase	0.0134	0.3136	0.415
Echinococcus granulosus	carbonic anhydrase	0.0134	0.3136	0.3459
Loa Loa (eye worm)	RNA recognition domain-containing protein domain-containing protein	0.0137	0.3223	0.4023
Trypanosoma brucei	carbonic anhydrase-like protein	0.0248	0.7445	0.7445
Brugia malayi	RNA recognition motif domain containing protein	0.0137	0.3223	0.4023
Brugia malayi	RNA binding protein	0.0137	0.3223	0.4023
Loa Loa (eye worm)	hypothetical protein	0.0066	0.0558	0.0696
Brugia malayi	hypothetical protein	0.0263	0.8011	1
Mycobacterium ulcerans	hypothetical protein	0.0166	0.4343	0.5
Brugia malayi	Latrophilin receptor protein 2	0.0066	0.0558	0.0696
Plasmodium falciparum	carbonic anhydrase	0.0134	0.3136	1
Schistosoma mansoni	hypothetical protein	0.0188	0.5187	0.6935
Loa Loa (eye worm)	carbonic anhydrase 3	0.0248	0.7445	0.9292
Brugia malayi	Iron-sulfur cluster assembly accessory protein	0.0054	0.0079	0.0098
Loa Loa (eye worm)	hypothetical protein	0.0134	0.3136	0.3914
Schistosoma mansoni	tar DNA-binding protein	0.0137	0.3223	0.4269
Loa Loa (eye worm)	hypothetical protein	0.0134	0.3136	0.3914
Brugia malayi	Carbonic anhydrase like protein 2 precursor	0.0134	0.3136	0.3914
Echinococcus granulosus	carbonic anhydrase	0.0134	0.3136	0.3459
Loa Loa (eye worm)	hypothetical protein	0.0143	0.3473	0.4335
Schistosoma mansoni	hypothetical protein	0.0134	0.3136	0.415
Schistosoma mansoni	hypothetical protein	0.0066	0.0558	0.0651
Trypanosoma brucei	mitochondrial DNA polymerase beta-PAK	0.0149	0.3703	0.3703
Schistosoma mansoni	carbonic anhydrase II (carbonate dehydratase II)	0.0248	0.7445	1
Loa Loa (eye worm)	hypothetical protein	0.0263	0.8011	1
Trypanosoma brucei	mitochondrial DNA polymerase beta	0.0315	1	1
Trypanosoma cruzi	mitochondrial DNA polymerase beta, putative	0.0315	1	1
Loa Loa (eye worm)	eukaryotic-type carbonic anhydrase	0.0134	0.3136	0.3914
Echinococcus multilocularis	carbonic anhydrase II	0.0248	0.7445	0.9239
Loa Loa (eye worm)	eukaryotic-type carbonic anhydrase	0.0248	0.7445	0.9292
Schistosoma mansoni	tar DNA-binding protein	0.0137	0.3223	0.4269
Loa Loa (eye worm)	RNA binding protein	0.0137	0.3223	0.4023
Brugia malayi	Eukaryotic-type carbonic anhydrase family protein	0.0134	0.3136	0.3914
Plasmodium vivax	ataxin-2 like protein, putative	0.0052	0	0.5
Brugia malayi	Eukaryotic-type carbonic anhydrase family protein	0.0134	0.3136	0.3914
Echinococcus granulosus	tar DNA binding protein	0.0137	0.3223	0.3575
Brugia malayi	TAR-binding protein	0.0137	0.3223	0.4023
Loa Loa (eye worm)	pigment dispersing factor receptor c	0.0209	0.5984	0.747
Trypanosoma cruzi	carbonic anhydrase-like protein, putative	0.0248	0.7445	0.7445
Loa Loa (eye worm)	hypothetical protein	0.0134	0.3136	0.3914
Schistosoma mansoni	hypothetical protein	0.0066	0.0558	0.0651
Echinococcus multilocularis	carbonic anhydrase	0.0134	0.3136	0.3459
Schistosoma mansoni	hypothetical protein	0.0066	0.0558	0.0651
Schistosoma mansoni	carbonic anhydrase II (carbonate dehydratase II)	0.0248	0.7445	1
Echinococcus multilocularis	tar DNA binding protein	0.0137	0.3223	0.3575
Trypanosoma cruzi	carbonic anhydrase-like protein, putative	0.0248	0.7445	0.7445
Brugia malayi	latrophilin 2 splice variant baaae	0.0143	0.3473	0.4335
Echinococcus granulosus	geminin	0.0188	0.5187	0.6211
Mycobacterium tuberculosis	Conserved hypothetical protein	0.0166	0.4343	0.5
Trypanosoma cruzi	mitochondrial DNA polymerase beta-PAK, putative	0.0149	0.3703	0.3703
Trypanosoma cruzi	mitochondrial DNA polymerase beta, putative	0.0315	1	1
Onchocerca volvulus	Huntingtin homolog	0.0128	0.2895	1
Brugia malayi	Eukaryotic-type carbonic anhydrase family protein	0.0134	0.3136	0.3914
Echinococcus multilocularis	geminin	0.0188	0.5187	0.6211
Echinococcus multilocularis	carbonic anhydrase	0.0134	0.3136	0.3459
Brugia malayi	Calcitonin receptor-like protein seb-1	0.0209	0.5984	0.747
Schistosoma mansoni	tar DNA-binding protein	0.0137	0.3223	0.4269
Echinococcus granulosus	survival motor neuron protein 1	0.0263	0.8011	1
Trypanosoma cruzi	mitochondrial DNA polymerase beta-PAK, putative	0.0054	0.0095	0.0095
Schistosoma mansoni	hypothetical protein	0.0188	0.5187	0.6935
Brugia malayi	Corticotropin releasing factor receptor 2 precursor, putative	0.0209	0.5984	0.747
Brugia malayi	Carbonic anhydrase like protein 2 precursor	0.0134	0.3136	0.3914

Activities

Activity type	Activity value	Assay description	Source	Reference
CC50 (ADMET)	= 110 uM	Cytotoxicity against HEK293T cells assessed as cell viability measured at 24 hrs by MTS assay	ChEMBL.	26288686
IC50 (binding)	= 0.94 uM	Inhibition of recombinant Influenza virus A/X-31 N-terminal RdRp PA subunit (1 to 217) expressed in Escherichia coli using single-stranded circular DNA plasmid M13mp18 as substrate after 2 hrs by agarose gel electrophoresis	ChEMBL.	26288686
Ki (binding)	= 1.85 uM	Inhibition of human CA1 using CO2 as substrate incubated for 6 hrs prior to substrate addition measured for 10 to 100 secs by stopped flow technique	ChEMBL.	22901388
Ki (binding)	= 3.02 uM	Inhibition of human CA2 using CO2 as substrate incubated for 6 hrs prior to substrate addition measured for 10 to 100 secs by stopped flow technique	ChEMBL.	22901388
Ki (binding)	= 9.24 uM	Inhibition of human CA12 using CO2 as substrate incubated for 6 hrs prior to substrate addition measured for 10 to 100 secs by stopped flow technique	ChEMBL.	22901388
Ki (binding)	= 15.1 uM	Inhibition of human CA9 using CO2 as substrate incubated for 6 hrs prior to substrate addition measured for 10 to 100 secs by stopped flow technique	ChEMBL.	22901388

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

ChEMBL: CHEMBL2070214

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.

Detailed information for compound 1659594