Detailed information for compound 1492782

Basic information

Technical information
  • TDR Targets ID: 1492782
  • Name: (E)-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)m ethyl]-3-(7-oxo-6,8-dihydro-5H-1,8-naphthyrid in-3-yl)prop-2-enamide
  • MW: 375.42 | Formula: C22H21N3O3
  • H donors: 1 H acceptors: 3 LogP: 2.51 Rotable bonds: 5
    Rule of 5 violations (Lipinski): 1
  • SMILES: O=C1CCc2c(N1)ncc(c2)/C=C/C(=O)N(Cc1oc2c(c1C)cccc2)C
  • InChi: 1S/C22H21N3O3/c1-14-17-5-3-4-6-18(17)28-19(14)13-25(2)21(27)10-7-15-11-16-8-9-20(26)24-22(16)23-12-15/h3-7,10-12H,8-9,13H2,1-2H3,(H,23,24,26)/b10-7+
  • InChiKey: QXTWSUQCXCWEHF-JXMROGBWSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (E)-N-methyl-N-[(3-methylbenzofuran-2-yl)methyl]-3-(7-oxo-6,8-dihydro-5H-1,8-naphthyridin-3-yl)prop-2-enamide
  • (E)-N-methyl-N-[(3-methyl-2-benzofuranyl)methyl]-3-(7-oxo-6,8-dihydro-5H-1,8-naphthyridin-3-yl)prop-2-enamide
  • (E)-3-(7-keto-6,8-dihydro-5H-1,8-naphthyridin-3-yl)-N-methyl-N-[(3-methylbenzofuran-2-yl)methyl]acrylamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Staphylococcus aureus Enoyl-ACP reductase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Plasmodium yoelii enoyl-acyl carrier reductase Get druggable targets OG5_130466 All targets in OG5_130466
Plasmodium berghei enoyl-acyl carrier reductase Get druggable targets OG5_130466 All targets in OG5_130466
Mycobacterium ulcerans enoyl-(acyl carrier protein) reductase Get druggable targets OG5_130466 All targets in OG5_130466
Mycobacterium tuberculosis NADH-dependent enoyl-[acyl-carrier-protein] reductase InhA (NADH-dependent enoyl-ACP reductase) Get druggable targets OG5_130466 All targets in OG5_130466
Plasmodium vivax enoyl-acyl carrier protein reductase Get druggable targets OG5_130466 All targets in OG5_130466
Mycobacterium leprae NADH-DEPENDENT ENOYL-[ACYL-CARRIER-PROTEIN] REDUCTASE INHA (NADH-DEPENDENT ENOYL-ACP REDUCTASE) Get druggable targets OG5_130466 All targets in OG5_130466
Chlamydia trachomatis enoyl-acyl-carrier protein reductase Get druggable targets OG5_130466 All targets in OG5_130466
Wolbachia endosymbiont of Brugia malayi enoyl-ACP reductase Get druggable targets OG5_130466 All targets in OG5_130466
Plasmodium falciparum enoyl-acyl carrier reductase Get druggable targets OG5_130466 All targets in OG5_130466
Toxoplasma gondii enoyl-acyl carrier reductase ENR Get druggable targets OG5_130466 All targets in OG5_130466
Neospora caninum enoyl-acyl carrier reductase, putative Get druggable targets OG5_130466 All targets in OG5_130466
Plasmodium knowlesi enoyl-acyl carrier reductase, putative Get druggable targets OG5_130466 All targets in OG5_130466
Trichomonas vaginalis hypothetical protein Get druggable targets OG5_130466 All targets in OG5_130466
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Mycobacterium ulcerans 3-oxoacyl-ACP reductase Enoyl-ACP reductase   243 aa 241 aa 22.0 %
Neospora caninum hypothetical protein Enoyl-ACP reductase   243 aa 198 aa 26.8 %
Mycobacterium ulcerans carveol-like dehydrogenase Enoyl-ACP reductase   243 aa 231 aa 22.5 %
Onchocerca volvulus Enoyl-ACP reductase   243 aa 248 aa 26.6 %
Mycobacterium tuberculosis 3-oxoacyl-[acyl-carrier protein] reductase FabG1 (3-ketoacyl-acyl carrier protein reductase) (mycolic acid biosynthesis a protei Enoyl-ACP reductase   243 aa 244 aa 21.7 %
Drosophila melanogaster CG31548 gene product from transcript CG31548-RA Enoyl-ACP reductase   243 aa 229 aa 21.8 %
Schistosoma mansoni short chain dehydrogenase Enoyl-ACP reductase   243 aa 204 aa 21.1 %
Candida albicans sorbose utilization/short-chain alcohol dehydrogenase Enoyl-ACP reductase   243 aa 241 aa 27.0 %
Mycobacterium ulcerans short chain dehydrogenase Enoyl-ACP reductase   243 aa 232 aa 27.2 %
Mycobacterium tuberculosis Probable short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 201 aa 25.4 %
Candida albicans similar to bacterial reductase Enoyl-ACP reductase   243 aa 242 aa 26.0 %
Candida albicans similar to Sou1p but not required for sorbose utilization Enoyl-ACP reductase   243 aa 240 aa 23.8 %
Mycobacterium ulcerans short chain dehydrogenase Enoyl-ACP reductase   243 aa 247 aa 24.7 %
Candida albicans SPS19-like orf, peroxisomal 2,4-dienoyl-CoA reductase Enoyl-ACP reductase   243 aa 235 aa 25.5 %
Chlamydia trachomatis oxoacy-ACP reductase Enoyl-ACP reductase   243 aa 237 aa 25.7 %
Mycobacterium tuberculosis Probable short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 206 aa 25.7 %
Mycobacterium leprae PROBABLE 3-OXOACYL-[ACYL-CARRIER PROTEIN] REDUCTASE FABG4 (3-KETOACYL-ACYL CARRIER PROTEIN REDUCTASE) Enoyl-ACP reductase   243 aa 247 aa 24.3 %
Mycobacterium ulcerans short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 208 aa 26.0 %
Loa Loa (eye worm) dehydrogenase Enoyl-ACP reductase   243 aa 238 aa 26.9 %
Dictyostelium discoideum short-chain dehydrogenase/reductase family protein Enoyl-ACP reductase   243 aa 236 aa 23.7 %
Trypanosoma brucei pteridine reductase 1 Enoyl-ACP reductase   243 aa 269 aa 24.5 %
Mycobacterium tuberculosis Probable short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 234 aa 25.6 %
Plasmodium yoelii 3-oxoacyl-acyl-carrier protein reductase precursor Enoyl-ACP reductase   243 aa 244 aa 23.8 %
Brugia malayi oxidoreductase, short chain dehydrogenase/reductase family protein Enoyl-ACP reductase   243 aa 244 aa 26.2 %
Mycobacterium ulcerans short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 235 aa 23.4 %
Mycobacterium ulcerans 3-ketoacyl-ACP reductase Enoyl-ACP reductase   243 aa 245 aa 27.3 %
Mycobacterium ulcerans short chain dehydrogenase Enoyl-ACP reductase   243 aa 245 aa 27.3 %
Mycobacterium ulcerans short chain dehydrogenase Enoyl-ACP reductase   243 aa 222 aa 23.0 %
Drosophila melanogaster CG31549 gene product from transcript CG31549-RA Enoyl-ACP reductase   243 aa 231 aa 28.1 %
Wolbachia endosymbiont of Brugia malayi Short-chain alcohol dehydrogenase family enzyme Enoyl-ACP reductase   243 aa 242 aa 24.0 %
Mycobacterium tuberculosis Possible oxidoreductase Enoyl-ACP reductase   243 aa 232 aa 25.9 %
Schistosoma mansoni 3-oxoacyl-[ACP] reductase Enoyl-ACP reductase   243 aa 251 aa 24.7 %
Mycobacterium tuberculosis Probable short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 211 aa 22.7 %
Mycobacterium ulcerans short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 255 aa 25.1 %
Plasmodium berghei 3-oxoacyl-[acyl-carrier-protein] reductase, putative Enoyl-ACP reductase   243 aa 248 aa 24.2 %
Schistosoma japonicum ko:K00065 2-deoxy-D-gluconate 3-dehydrogenase [EC1.1.1.125], putative Enoyl-ACP reductase   243 aa 244 aa 24.2 %
Mycobacterium ulcerans oxidoreductase Enoyl-ACP reductase   243 aa 242 aa 28.9 %
Mycobacterium tuberculosis Probable short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 252 aa 23.4 %
Trypanosoma brucei beta-D-hydroxybutyrate dehydrogenase Enoyl-ACP reductase   243 aa 250 aa 22.0 %
Mycobacterium ulcerans short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 205 aa 21.0 %
Candida albicans similar to peroxisomal 2,4-dienoyl-CoA reductase Enoyl-ACP reductase   243 aa 238 aa 27.3 %
Trypanosoma cruzi NAD(P)-dependent oxidoreductase, putative Enoyl-ACP reductase   243 aa 254 aa 21.3 %
Mycobacterium tuberculosis Probable 3-oxoacyl-[acyl-carrier protein] reductase FabG4 (3-ketoacyl-acyl carrier protein reductase) Enoyl-ACP reductase   243 aa 249 aa 23.3 %
Mycobacterium tuberculosis Probable short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 247 aa 27.1 %
Trypanosoma congolense short chain dehydrogenase, putative Enoyl-ACP reductase   243 aa 250 aa 19.6 %
Dictyostelium discoideum hypothetical protein Enoyl-ACP reductase   243 aa 198 aa 23.7 %
Candida albicans SPS19-like orf, peroxisomal 2,4-dienoyl-CoA reductase Enoyl-ACP reductase   243 aa 235 aa 25.5 %
Mycobacterium ulcerans short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 241 aa 26.1 %
Toxoplasma gondii short chain dehydrogenase family protein, putative Enoyl-ACP reductase   243 aa 247 aa 23.1 %
Drosophila melanogaster CG3603 gene product from transcript CG3603-RB Enoyl-ACP reductase   243 aa 246 aa 24.0 %
Dictyostelium discoideum short-chain dehydrogenase/reductase family protein Enoyl-ACP reductase   243 aa 212 aa 23.1 %
Trypanosoma brucei gambiense NAD or NADP dependent oxidoreductase,putative Enoyl-ACP reductase   243 aa 255 aa 23.1 %
Candida albicans similar to SOU1 but not required for sorbose utilization Enoyl-ACP reductase   243 aa 240 aa 23.8 %
Mycobacterium tuberculosis Probable short-chain type dehydrogenase/reductase Enoyl-ACP reductase   243 aa 217 aa 26.3 %
Mycobacterium ulcerans short chain dehydrogenase Enoyl-ACP reductase   243 aa 248 aa 25.4 %
Mycobacterium tuberculosis Probable oxidoreductase Enoyl-ACP reductase   243 aa 231 aa 26.0 %
Candida albicans sorbose utilization/short-chain alcohol dehydrogenase Enoyl-ACP reductase   243 aa 241 aa 27.0 %
Candida albicans short-chain alcohol dehydrogenase superfamily Enoyl-ACP reductase   243 aa 242 aa 26.0 %
Dictyostelium discoideum glucose/ribitol dehydrogenase family protein Enoyl-ACP reductase   243 aa 208 aa 23.6 %
Schistosoma japonicum ko:K00100 retinol dehydrogenase 14 (all-trans/9-cis/11-cis) [EC:1.1.1.-], putative Enoyl-ACP reductase   243 aa 206 aa 21.8 %
Trypanosoma cruzi NAD(P)-dependent oxidoreductase, putative Enoyl-ACP reductase   243 aa 254 aa 20.9 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Trypanosoma cruzi hypothetical protein, conserved 0.021 0.8891 1
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.0029 0.0485 0.1866
Plasmodium falciparum enoyl-acyl carrier reductase 0.0223 0.9515 1
Schistosoma mansoni histone-lysine n-methyltransferase suv9 0.0029 0.0485 0.1866
Brugia malayi PHD-finger family protein 0.0029 0.0453 0.0522
Mycobacterium ulcerans hypothetical protein 0.0024 0.0239 0.0251
Wolbachia endosymbiont of Brugia malayi enoyl-ACP reductase 0.0223 0.9515 0.5
Toxoplasma gondii histone lysine methyltransferase SET/SUV39 0.0029 0.0485 0.0035
Schistosoma mansoni bromodomain-containing nuclear protein 1 brd1 0.0029 0.0453 0.1742
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1215 0.4675
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0045 0.1215 0.3471
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0045 0.1215 0.3471
Trypanosoma brucei hypothetical protein, conserved 0.021 0.8891 1
Loa Loa (eye worm) jmjC domain-containing protein 0.0059 0.188 0.2166
Echinococcus granulosus citrate lyase subunit beta protein 0.0024 0.0239 0.0683
Trichomonas vaginalis hypothetical protein 0.0223 0.9515 0.9515
Echinococcus multilocularis Transcription factor, JmjC domain containing protein 0.0094 0.3502 1
Echinococcus granulosus jumonji domain containing protein 0.004 0.0978 0.2792
Loa Loa (eye worm) PHD-finger family protein 0.0029 0.0453 0.0522
Leishmania major 2,4-dihydroxyhept-2-ene-1,7-dioic acid aldolase, putative 0.0024 0.0239 0.0269
Brugia malayi Pre-SET motif family protein 0.0205 0.8678 1
Echinococcus granulosus peregrin 0.0029 0.0453 0.1294
Brugia malayi Pre-SET motif family protein 0.0029 0.0485 0.0559
Echinococcus granulosus histone lysine methyltransferase setb 0.0029 0.0485 0.1385
Echinococcus multilocularis PHD finger protein rhinoceros 0.0029 0.0453 0.1294
Loa Loa (eye worm) GTP-binding regulatory protein Gs alpha-S chain 0.0045 0.1215 0.14
Echinococcus granulosus Transcription factor JmjC domain containing protein 0.0094 0.3502 1
Echinococcus granulosus lysine specific demethylase 5A 0.0035 0.0735 0.2099
Mycobacterium ulcerans enoyl-(acyl carrier protein) reductase 0.0223 0.9515 1
Echinococcus multilocularis jumonji domain containing protein 0.004 0.0978 0.2792
Loa Loa (eye worm) hypothetical protein 0.0029 0.0453 0.0522
Trypanosoma cruzi hypothetical protein, conserved 0.021 0.8891 1
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1215 0.4675
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0045 0.1215 0.3471
Mycobacterium ulcerans citrate (pro-3S)-lyase subunit beta 0.0024 0.0239 0.0251
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.0029 0.0485 0.1866
Schistosoma mansoni jumonji/arid domain-containing protein 0.0035 0.0735 0.2827
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.0029 0.0485 0.1866
Mycobacterium ulcerans hypothetical protein 0.0024 0.0239 0.0251
Trypanosoma cruzi 2,4-dihydroxyhept-2-ene-1,7-dioic acid aldolase, putative 0.0024 0.0239 0.0269
Plasmodium vivax enoyl-acyl carrier protein reductase 0.0223 0.9515 1
Toxoplasma gondii enoyl-acyl carrier reductase ENR 0.0223 0.9515 1
Mycobacterium tuberculosis Probable citrate (pro-3S)-lyase (beta subunit) CitE (citrase) (citratase) (citritase) (citridesmolase) (citrase aldolase) 0.0024 0.0239 0.0251
Echinococcus multilocularis histone lysine N methyltransferase SETMAR 0.0029 0.0485 0.1385
Loa Loa (eye worm) hypothetical protein 0.0049 0.141 0.1625
Loa Loa (eye worm) pre-SET domain-containing protein family protein 0.0205 0.8678 1
Leishmania major hypothetical protein, conserved 0.021 0.8891 1
Echinococcus multilocularis lysine specific demethylase 5A 0.0035 0.0735 0.2099
Mycobacterium tuberculosis NADH-dependent enoyl-[acyl-carrier-protein] reductase InhA (NADH-dependent enoyl-ACP reductase) 0.0223 0.9515 1
Echinococcus multilocularis peregrin 0.0029 0.0453 0.1294
Mycobacterium leprae NADH-DEPENDENT ENOYL-[ACYL-CARRIER-PROTEIN] REDUCTASE INHA (NADH-DEPENDENT ENOYL-ACP REDUCTASE) 0.0223 0.9515 0.5
Mycobacterium tuberculosis Conserved protein 0.0024 0.0239 0.0251
Mycobacterium ulcerans citrate lyase beta subunit, CitE_2 0.0024 0.0239 0.0251
Loa Loa (eye worm) hypothetical protein 0.0029 0.0485 0.0559
Trichomonas vaginalis Citrate lyase beta chain, putative 0.0024 0.0239 0.0239
Echinococcus multilocularis histone lysine methyltransferase setb histone lysine methyltransferase eggless 0.0029 0.0485 0.1385
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0045 0.1215 0.3471
Echinococcus multilocularis citrate lyase subunit beta protein 0.0024 0.0239 0.0683
Echinococcus granulosus PHD finger protein rhinoceros 0.0029 0.0453 0.1294
Mycobacterium ulcerans citrate (pro-3S)-lyase subunit beta 0.0024 0.0239 0.0251
Trypanosoma cruzi 2,4-dihydroxyhept-2-ene-1,7-dioic acid aldolase, putative 0.0024 0.0239 0.0269
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0045 0.1215 0.4675
Chlamydia trachomatis enoyl-acyl-carrier protein reductase 0.0223 0.9515 0.5
Plasmodium vivax SET domain protein, putative 0.0029 0.0485 0.0035
Echinococcus granulosus 5'partial|histone lysine N methyltransferase SETDB2 0.0028 0.0435 0.1241
Brugia malayi GTP-binding regulatory protein Gs alpha-S chain, putative 0.0045 0.1215 0.14
Brugia malayi jmjC domain containing protein 0.0035 0.0735 0.0847
Entamoeba histolytica deoxycytidyl transferase, putative 0.0019 0 0.5
Schistosoma mansoni jumonji domain containing protein 0.0075 0.26 1
Trichomonas vaginalis set domain proteins, putative 0.0234 1 1
Schistosoma mansoni hypothetical protein 0.0029 0.0453 0.1742
Schistosoma mansoni jumonji/arid domain-containing protein 0.0035 0.0735 0.2827
Brugia malayi jmjC domain containing protein 0.0094 0.3502 0.4035
Brugia malayi Bromodomain containing protein 0.0029 0.0453 0.0522
Giardia lamblia PHD finger protein 15 0.0029 0.0453 1
Onchocerca volvulus 0.0029 0.0485 0.0034
Loa Loa (eye worm) jmjC domain-containing protein 0.0035 0.0735 0.0847

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 0.029 uM Inhibition of Staphylococcus aureus FabI-mediated reduction of enoyl-ACP preincubated for 30 mins measured after 2 hrs by spectrophotometry ChEMBL. 25036796
Inhibition (binding) = 100 % Inhibition of Staphylococcus aureus FabI-mediated reduction of enoyl-ACP preincubated at 1 uM for 30 mins measured after 2 hrs by spectrophotometry ChEMBL. 25036796
MIC (functional) = 0.016 ug ml-1 Antibacterial activity against acrAB-deficient Escherichia coli AG100a ChEMBL. 19487444
MIC (functional) = 0.5 ug ml-1 Antibacterial activity against Escherichia coli by CLSI M100-S17 method ChEMBL. 19487444
MIC (functional) > 32 ug ml-1 Antibacterial activity against Escherichia coli AG100 ChEMBL. 19487444
MIC50 (functional) = 4 ug ml-1 Antibacterial activity against Escherichia coli by CLSI M100-S17 method ChEMBL. 19487444
MIC90 (functional) > 4 ug ml-1 Antibacterial activity against Escherichia coli by CLSI M100-S17 method ChEMBL. 19487444
Stabilty (ADMET) = 55.4 % Metabolic stability in mouse liver mirosomes assessed as compound remaining at 1 uM after 15 mins by LC-MS/MS analysis ChEMBL. 25036796

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.
 
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External resources for this compound

Bibliographic References

No literature references available for this target.

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