Detailed information for compound 13768

Basic information

Technical information
  • TDR Targets ID: 13768
  • Name: 5-methoxy-N-[6-(2-methylpyridin-3-yl)oxypyrid in-3-yl]-6-(trifluoromethyl)-2,3-dihydroindol e-1-carboxamide
  • MW: 444.406 | Formula: C22H19F3N4O3
  • H donors: 1 H acceptors: 3 LogP: 3.68 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1cc2CCN(c2cc1C(F)(F)F)C(=O)Nc1ccc(nc1)Oc1cccnc1C
  • InChi: 1S/C22H19F3N4O3/c1-13-18(4-3-8-26-13)32-20-6-5-15(12-27-20)28-21(30)29-9-7-14-10-19(31-2)16(11-17(14)29)22(23,24)25/h3-6,8,10-12H,7,9H2,1-2H3,(H,28,30)
  • InChiKey: WBGZTUVFDUVQKY-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5-methoxy-N-[6-[(2-methyl-3-pyridyl)oxy]-3-pyridyl]-6-(trifluoromethyl)indoline-1-carboxamide
  • 5-methoxy-N-[6-[(2-methyl-3-pyridyl)oxy]-3-pyridyl]-6-(trifluoromethyl)-1-indolinecarboxamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens 5-hydroxytryptamine (serotonin) receptor 2B, G protein-coupled Starlite/ChEMBL References
Homo sapiens 5-hydroxytryptamine (serotonin) receptor 2A, G protein-coupled Starlite/ChEMBL References
Homo sapiens 5-hydroxytryptamine (serotonin) receptor 2C, G protein-coupled Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Brugia malayi Serotonin receptor Get druggable targets OG5_135430 All targets in OG5_135430
Echinococcus multilocularis conserved hypothetical protein Get druggable targets OG5_144688 All targets in OG5_144688
Echinococcus granulosus hypothetical protein Get druggable targets OG5_144688 All targets in OG5_144688
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
Leishmania major xanthine phosphoribosyltransferase 0.0216 0.0958 1
Treponema pallidum penicillin-binding protein (pbp-1) 0.1858 1 1
Mycobacterium ulcerans hypoxanthine-guanine phosphoribosyltransferase Hpt 0.0216 0.0958 0.1068
Mycobacterium leprae Probable hypoxanthine-guanine phosphoribosyltransferase Hpt (HGPRT) (HGPRTase) (hypoxanthine phosphoribosyltransferase) (IMP pho 0.0166 0.0679 0.111
Trypanosoma brucei beta lactamase 0.0127 0.0467 0.4708
Schistosoma mansoni high voltage-activated calcium channel Cav1 0.0079 0.02 0.2092
Treponema pallidum penicillin-binding protein (pbp-2) 0.0985 0.5192 0.517
Trichomonas vaginalis set domain proteins, putative 0.0241 0.1091 0.2031
Schistosoma mansoni Adenine phosphoribosyltransferase 0.0051 0.0045 0.047
Mycobacterium tuberculosis Probable bifunctional penicillin-binding protein 1A/1B PonA1 (murein polymerase) (PBP1): penicillin-insensitive transglycosylase 0.0284 0.1329 0.2249
Mycobacterium tuberculosis Transmembrane serine/threonine-protein kinase B PknB (protein kinase B) (STPK B) 0.0159 0.0642 0.1046
Trichomonas vaginalis conserved hypothetical protein 0.0985 0.5192 1
Brugia malayi hypothetical protein 0.0523 0.2646 0.9209
Schistosoma mansoni Adenine phosphoribosyltransferase 0.0051 0.0045 0.047
Mycobacterium tuberculosis Probable bifunctional membrane-associated penicillin-binding protein 1A/1B PonA2 (murein polymerase) [includes: penicillin-insen 0.086 0.4505 0.7813
Trypanosoma cruzi Adenine phosphoribosyltransferase, putative 0.0051 0.0045 0.016
Brugia malayi orotate phosphoribosyltransferase family protein 0.0051 0.0045 0.0157
Echinococcus granulosus hypoxanthine guanine phosphoribosyltransferase 0.0216 0.0958 0.2175
Schistosoma mansoni hypoxanthine-guanine phosphoribosyltransferase 0.0216 0.0958 1
Echinococcus multilocularis Protein lozenge 0.0066 0.0127 0.0292
Loa Loa (eye worm) hypothetical protein 0.0523 0.2646 1
Mycobacterium ulcerans penicillin-binding lipoprotein 0.0739 0.3838 0.4438
Mycobacterium leprae PROBABLE CONSERVED LIPOPROTEIN LPQF 0.0127 0.0467 0.0739
Brugia malayi Voltage-gated calcium channel, L-type, alpha subunit. C. elegans egl-19 ortholog 0.0079 0.02 0.0697
Echinococcus multilocularis voltage dependent L type calcium channel subunit 0.0079 0.02 0.046
Loa Loa (eye worm) calcium channel 0.0079 0.02 0.0597
Loa Loa (eye worm) hypothetical protein 0.0317 0.1511 0.5636
Mycobacterium leprae POSSIBLE PENICILLIN-BINDING LIPOPROTEIN 0.0739 0.3838 0.6645
Treponema pallidum hypothetical protein 0.0159 0.0642 0.06
Toxoplasma gondii hypoxanthine-xanthine-guanine phosphoribosyl transferase HXGPRT 0.0216 0.0958 1
Onchocerca volvulus 0.0241 0.1091 0.402
Trypanosoma cruzi hypoxanthine-guanine phosphoribosyltransferase, putative 0.0216 0.0958 1
Entamoeba histolytica hypothetical protein 0.0042 0 0.5
Trypanosoma brucei orotidine-5-phosphate decarboxylase/orotate phosphoribosyltransferase, putative 0.0051 0.0045 0.016
Trypanosoma brucei Adenine phosphoribosyltransferase, putative 0.0051 0.0045 0.016
Echinococcus multilocularis voltage dependent L type calcium channel subunit 0.0079 0.02 0.046
Treponema pallidum penicillin-binding protein (pbp-3) 0.1762 0.9468 0.9465
Loa Loa (eye worm) runx1 0.0066 0.0127 0.0316
Mycobacterium leprae PROBABLE BIFUNCTIONAL PENICILLIN-BINDING PROTEIN 1A/1B PONA1 (MUREIN POLYMERASE) (PBP1): PENICILLIN-INSENSITIVE TRANSGLYCOSYLASE 0.0985 0.5192 0.9017
Mycobacterium ulcerans bifunctional penicillin-binding protein 1A/1B PonA1 0.0985 0.5192 0.6022
Mycobacterium tuberculosis Possible penicillin-binding lipoprotein 0.0739 0.3838 0.6645
Trypanosoma cruzi Adenine phosphoribosyltransferase, putative 0.0051 0.0045 0.016
Plasmodium falciparum hypoxanthine-guanine phosphoribosyltransferase 0.0216 0.0958 1
Schistosoma mansoni uracil phosphoribosyltransferase 0.0051 0.0045 0.047
Giardia lamblia Guanine phosphoribosyltransferase 0.0216 0.0958 1
Trypanosoma cruzi orotidine-5-phosphate decarboxylase/orotate phosphoribosyltransferase, putative 0.0051 0.0045 0.016
Entamoeba histolytica hypothetical protein 0.0042 0 0.5
Trypanosoma brucei Adenine phosphoribosyltransferase, putative 0.0051 0.0045 0.016
Echinococcus multilocularis voltage dependent calcium channel type d subunit 0.0079 0.02 0.046
Wolbachia endosymbiont of Brugia malayi cell division protein FtsI 0.1858 1 1
Loa Loa (eye worm) pre-SET domain-containing protein family protein 0.0211 0.093 0.3402
Echinococcus granulosus uridine 5' monophosphate synthase 0.0051 0.0045 0.0102
Mycobacterium ulcerans penicillin-binding protein PbpA 0.1087 0.5753 0.6678
Schistosoma mansoni hypoxanthine-guanine phosphoribosyltransferase 0.0216 0.0958 1
Trypanosoma brucei hypoxanthine-guanine phosphoribosyltransferase, putative 0.0216 0.0958 1
Onchocerca volvulus 0.0523 0.2646 1
Echinococcus granulosus voltage dependent calcium channel 0.0079 0.02 0.0455
Schistosoma mansoni lozenge 0.0066 0.0127 0.133
Brugia malayi Serotonin receptor 0.0564 0.2873 1
Trypanosoma cruzi orotidine-5-phosphate decarboxylase/orotate phosphoribosyltransferase, putative 0.0051 0.0045 0.016
Mycobacterium tuberculosis Class a beta-lactamase BlaC 0.0265 0.1226 0.2069
Mycobacterium leprae Probable penicillin-binding protein PbpA 0.1087 0.5753 1
Leishmania major hypoxanthine-guanine phosphoribosyltransferase 0.0216 0.0958 1
Echinococcus multilocularis voltage dependent calcium channel type d subunit 0.0079 0.02 0.046
Schistosoma mansoni hypoxanthine-guanine phosphoribosyltransferase 0.0051 0.0045 0.047
Brugia malayi Phosphoribosyl transferase domain containing protein 0.0216 0.0958 0.3333
Echinococcus multilocularis adenine phosphoribosyltransferase 0.0051 0.0045 0.0103
Mycobacterium ulcerans penicillin-binding membrane protein PbpB 0.1603 0.8592 1
Echinococcus multilocularis uridine 5' monophosphate synthase 0.0051 0.0045 0.0103
Brugia malayi hypothetical protein 0.0122 0.0436 0.1516
Mycobacterium tuberculosis Hypoxanthine-guanine phosphoribosyltransferase Hpt (HGPRT) (HGPRTase) (hypoxanthine phosphoribosyltransferase) (imp pyrophosphor 0.0166 0.0679 0.111
Entamoeba histolytica hypothetical protein 0.0042 0 0.5
Mycobacterium ulcerans serine/threonine-protein kinase B PknB 0.0159 0.0642 0.0698
Plasmodium vivax hypoxanthine-guanine phosphoribosyltransferase, putative 0.0216 0.0958 1
Echinococcus multilocularis hypoxanthine guanine phosphoribosyltransferase 0.0216 0.0958 0.2199
Mycobacterium ulcerans bifunctional membrane-associated penicillin-binding protein 1A/1B PonA2 0.086 0.4505 0.5218
Echinococcus multilocularis voltage dependent calcium channel 0.0079 0.02 0.046
Trypanosoma cruzi Adenine phosphoribosyltransferase, putative 0.0051 0.0045 0.016
Echinococcus granulosus hypothetical protein 0.0842 0.4403 1
Brugia malayi Pre-SET motif family protein 0.0211 0.093 0.3236
Mycobacterium leprae Probable transmembrane serine/threonine-protein kinase B PknB (protein kinase B) (STPK B) 0.0159 0.0642 0.1046
Trypanosoma brucei hypoxanthine-guanine phosphoribosyltransferase 0.0216 0.0958 1
Entamoeba histolytica hypothetical protein 0.0042 0 0.5
Mycobacterium ulcerans lipoprotein LpqF 0.0127 0.0467 0.0493
Echinococcus granulosus voltage dependent calcium channel type d subunit|voltage dependent calcium channel alpha 1 0.0079 0.02 0.0455
Echinococcus granulosus hypoxanthine guanine phosphoribosyltransferase 0.0216 0.0958 0.2175
Echinococcus granulosus voltage dependent calcium channel type d subunit|voltage dependent calcium channel|voltage dependent L type calcium channel subu 0.0079 0.02 0.0455
Echinococcus multilocularis hypoxanthine guanine phosphoribosyltransferase 0.0216 0.0958 0.2199
Brugia malayi Adenine phosphoribosyltransferase 0.0051 0.0045 0.0157
Echinococcus granulosus adenine phosphoribosyltransferase 0.0051 0.0045 0.0102
Trypanosoma cruzi hypoxanthine-guanine phosphoribosyltransferase, putative 0.0216 0.0958 1
Mycobacterium ulcerans class a beta-lactamase, BlaC 0.0265 0.1226 0.1382
Schistosoma mansoni hypoxanthine-guanine phosphoribosyltransferase 0.0051 0.0045 0.047
Loa Loa (eye worm) hypothetical protein 0.0079 0.02 0.0597
Mycobacterium leprae PROBABLE BIFUNCTIONAL MEMBRANE-ASSOCIATED PENICILLIN-BINDING PROTEIN 1A/1B PONA2 (MUREIN POLYMERASE) [INCLUDES: PENICILLIN-INSEN 0.086 0.4505 0.7813
Schistosoma mansoni high voltage-activated calcium channel Cav2A 0.0079 0.02 0.2092
Loa Loa (eye worm) hypothetical protein 0.0523 0.2646 1
Trichomonas vaginalis hypoxanthine-guanine phosphoribosyltransferase, putative 0.0216 0.0958 0.1773
Trypanosoma brucei hypoxanthine-guanine phosphoribosyltransferase 0.0216 0.0958 1
Schistosoma mansoni orotidine 5'-phosphate decarboxylase 0.0051 0.0045 0.047
Trypanosoma cruzi hypoxanthine-guanine phosphoribosyltransferase, putative 0.0216 0.0958 1
Mycobacterium tuberculosis Probable penicillin-binding membrane protein PbpB 0.0398 0.1958 0.3351
Mycobacterium leprae Probable penicillin-binding membrane protein PbpB 0.0398 0.1958 0.3351
Echinococcus multilocularis voltage dependent calcium channel 0.0079 0.02 0.046
Onchocerca volvulus 0.0216 0.0958 0.3509
Trypanosoma cruzi Adenine phosphoribosyltransferase, putative 0.0051 0.0045 0.016
Trypanosoma cruzi hypoxanthine-guanine phosphoribosyltransferase, putative 0.0216 0.0958 1
Echinococcus granulosus voltage dependent L type calcium channel subunit|voltage dependent calcium channel 0.0079 0.02 0.0455
Schistosoma mansoni voltage-gated cation channel 0.0079 0.02 0.2092
Mycobacterium tuberculosis Probable penicillin-binding protein PbpA 0.1087 0.5753 1
Mycobacterium tuberculosis Probable conserved lipoprotein LpqF 0.0127 0.0467 0.0739
Echinococcus multilocularis conserved hypothetical protein 0.0833 0.4355 1

Activities

Activity type Activity value Assay description Source Reference
IC50 (ADMET) > 100 uM Inhibition of heterologously expressed human cytochrome P450 1A2. ChEMBL. 10737744
IC50 (ADMET) > 100 uM Inhibition of heterologously expressed human cytochrome P450 1A2. ChEMBL. 10737744
ID50 (functional) = 2.8 mg kg-1 Dose required to reverse mCPP induced hypolocomotion in rat after oral administration. ChEMBL. 10737744
ID50 (functional) = 2.8 mg kg-1 Dose required to reverse mCPP induced hypolocomotion by 50% at 7 mg/kg, ip administration 30 min pretest ChEMBL. 10969986
Ki (binding) = -9.2 Binding affinity towards human cloned 5-hydroxytryptamine receptor 2C in HEK293 cells, using [3H]-mesulergine as radioligand. ChEMBL. 10737744
Ki (binding) = -9.2 Binding affinity towards human cloned 5-hydroxytryptamine 2C receptor of HEK293 cells by displacement of [3H]-mesulergine ChEMBL. 10969986
Ki (binding) = -7.3 Binding affinities towards human cloned 5-hydroxytryptamine 2B receptor in HEK293 cells using [3H]-5-HT as radioligand. ChEMBL. 10737744
Ki (binding) = -7.3 Binding affinity towards human cloned 5-HT2B receptor of HEK293 cells by displacement of [3H]-5-HT ChEMBL. 10969986
Ki (binding) = -6.1 Binding affinity towards human cloned 5-hydroxytryptamine receptor 2A in HEK293 cells, using [3H]-ketanserin as radioligand. ChEMBL. 10737744
Ki (binding) = -6.1 Binding affinity towards human cloned 5-hydroxytryptamine 2A receptor of HEK293 cells by displacement of [3H]-ketanserin ChEMBL. 10969986
Log Ki (binding) = 6.1 Binding affinity towards human cloned 5-hydroxytryptamine receptor 2A in HEK293 cells, using [3H]-ketanserin as radioligand. ChEMBL. 10737744
Log Ki (binding) = 6.1 Binding affinity towards human cloned 5-hydroxytryptamine 2A receptor of HEK293 cells by displacement of [3H]-ketanserin ChEMBL. 10969986
Log Ki (binding) = 7.3 Binding affinities towards human cloned 5-hydroxytryptamine 2B receptor in HEK293 cells using [3H]-5-HT as radioligand. ChEMBL. 10737744
Log Ki (binding) = 7.3 Binding affinity towards human cloned 5-HT2B receptor of HEK293 cells by displacement of [3H]-5-HT ChEMBL. 10969986
Log Ki (binding) = 9.2 Binding affinity towards human cloned 5-hydroxytryptamine receptor 2C in HEK293 cells, using [3H]-mesulergine as radioligand. ChEMBL. 10737744
Log Ki (binding) = 9.2 Binding affinity towards human cloned 5-hydroxytryptamine 2C receptor of HEK293 cells by displacement of [3H]-mesulergine ChEMBL. 10969986
Selectivity (binding) = 80 Selectivity index for binding affinities for 5-HT2C and 5-HT2B recetptors ChEMBL. 10737744
Selectivity (binding) = 80 Selectivity expressed as ratio of serotonin 5-HT2C receptor over serotonin 5-HT2B receptor ChEMBL. 10969986
Selectivity (binding) = 1300 Selectivity index for binding affinities for 5-HT2C and 5-HT2A receptors ChEMBL. 10737744
Selectivity (binding) = 1300 Selectivity expressed as ratio of serotonin 5-HT2C receptor over serotonin 5-HT2A receptor ChEMBL. 10969986

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

2 literature references were collected for this gene.

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