Detailed information for compound 57229

Basic information

Technical information
  • TDR Targets ID: 57229
  • Name: ethyl 5-[3-(aminomethyl)-4-hydroxybenzoyl]-6, 7-dichloro-2,3-dihydro-1-benzofuran-2-carboxy late
  • MW: 410.248 | Formula: C19H17Cl2NO5
  • H donors: 2 H acceptors: 3 LogP: 3.9 Rotable bonds: 6
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCOC(=O)C1Cc2c(O1)c(Cl)c(c(c2)C(=O)c1ccc(c(c1)CN)O)Cl
  • InChi: 1S/C19H17Cl2NO5/c1-2-26-19(25)14-7-10-6-12(15(20)16(21)18(10)27-14)17(24)9-3-4-13(23)11(5-9)8-22/h3-6,14,23H,2,7-8,22H2,1H3
  • InChiKey: ARFHLVKVAQOBOU-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • ethyl 5-[3-(aminomethyl)-4-hydroxy-benzoyl]-6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylate
  • 5-[[3-(aminomethyl)-4-hydroxyphenyl]-oxomethyl]-6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid ethyl ester
  • ethyl 5-[3-(aminomethyl)-4-hydroxy-phenyl]carbonyl-6,7-dichloro-2,3-dihydro-1-benzofuran-2-carboxylate
  • 5-[3-(aminomethyl)-4-hydroxy-benzoyl]-6,7-dichloro-coumaran-2-carboxylic acid ethyl ester
  • 5-[3-(aminomethyl)-4-hydroxy-benzoyl]-6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid ethyl ester

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
Trypanosoma brucei calpain-like cysteine peptidase, putative 0.0109 0.0667 1
Plasmodium vivax GMP synthetase, putative 0.0033 0.0079 0.0168
Schistosoma mansoni lipoxygenase 0.0054 0.0238 0.06
Plasmodium vivax histone acetyltransferase GCN5, putative 0.0042 0.0143 0.0461
Trypanosoma brucei calpain-like cysteine peptidase, putative 0.0109 0.0667 1
Mycobacterium ulcerans beta-ketoacyl synthase-like protein 0.0309 0.2218 0.2218
Chlamydia trachomatis dihydrofolate reductase 0.0175 0.1174 0.52
Entamoeba histolytica fatty acid elongase, putative 0.004 0.0132 0.2058
Entamoeba histolytica glycosyl hydrolase, family 31 protein 0.0033 0.0076 0.119
Mycobacterium tuberculosis 3-oxoacyl-[acyl-carrier-protein] synthase III FabH (beta-ketoacyl-ACP synthase III) (KAS III) 0.0309 0.2218 0.2218
Trichomonas vaginalis alpha-glucosidase, putative 0.0033 0.0076 0.0314
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0067 0.0338 0.5075
Schistosoma mansoni alpha-glucosidase 0.0343 0.2483 0.8938
Trypanosoma brucei GMP synthase [glutamine-hydrolysing] 0.0033 0.0079 0.0049
Schistosoma mansoni alpha-l-fucosidase 0.038 0.2769 1
Trypanosoma brucei calpain-like cysteine peptidase, putative 0.0109 0.0667 1
Trichomonas vaginalis alpha-glucosidase, putative 0.0033 0.0076 0.0314
Entamoeba histolytica fatty acid elongase, putative 0.004 0.0132 0.2058
Plasmodium falciparum beta-ketoacyl-ACP synthase III 0.0309 0.2218 1
Onchocerca volvulus Uncharacterized family 31 glucosidase KIAA1161 homolog 0.0033 0.0076 0.0475
Brugia malayi dihydrofolate reductase family protein 0.0175 0.1174 0.424
Mycobacterium ulcerans 3-oxoacyl-ACP synthase 0.0309 0.2218 0.2218
Trypanosoma cruzi calpain-like cysteine peptidase, putative 0.0109 0.0667 1
Entamoeba histolytica NAD synthetase, putative 0.0083 0.0467 0.7278
Entamoeba histolytica glycosyl hydrolase, family 31 protein 0.0033 0.0076 0.119
Echinococcus granulosus GMP synthase glutamine hydrolyzing 0.0033 0.0079 0.0011
Mycobacterium leprae PROBABLE 6-PHOSPHOFRUCTOKINASE PFKA (PHOSPHOHEXOKINASE) (PHOSPHOFRUCTOKINASE) 0.0106 0.0642 0.5471
Entamoeba histolytica fatty acid elongase, putative 0.004 0.0132 0.2058
Brugia malayi phosphofructokinase 0.0106 0.0642 0.232
Trypanosoma cruzi NAD+ synthase, putative 0.0083 0.0467 0.6626
Loa Loa (eye worm) glycosyl hydrolase family 31 protein 0.0343 0.2483 0.8967
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0175 0.1174 0.1174
Giardia lamblia NH3-dependent NAD+ synthetase 0.0083 0.0467 1
Schistosoma mansoni alpha-glucosidase 0.0343 0.2483 0.8938
Trichomonas vaginalis maltase-glucoamylase, putative 0.0033 0.0076 0.0314
Trypanosoma cruzi ATP-dependent 6-phosphofructokinase, glycosomal 0.0106 0.0642 0.9589
Plasmodium vivax glutamine-dependent NAD(+) synthetase, putative 0.0083 0.0467 0.1952
Brugia malayi Glycosyl hydrolases family 31 protein 0.0033 0.0076 0.0276
Onchocerca volvulus 0.0231 0.161 1
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0067 0.0338 0.1358
Wolbachia endosymbiont of Brugia malayi 3-oxoacyl-ACP synthase 0.0309 0.2218 0.5
Trypanosoma brucei variant surface glycoprotein (VSG), putative 0.0109 0.0667 1
Mycobacterium ulcerans alpha-L-fucosidase 0.038 0.2769 0.2769
Loa Loa (eye worm) hypothetical protein 0.0033 0.0079 0.0287
Mycobacterium tuberculosis Glutamine-dependent NAD(+) synthetase NadE (NAD(+) synthase [glutamine-hydrolysing]) 0.0083 0.0467 0.0467
Trichomonas vaginalis cat eye syndrome critical region protein 2, cscr2, putative 0.0042 0.0143 0.0935
Echinococcus granulosus fucosidase alpha L 1 tissue 0.038 0.2769 1
Treponema pallidum diphosphate--fructose-6-phosphate 1-phosphotransferase 0.0106 0.0642 1
Trypanosoma brucei NAD+ synthase, putative 0.0083 0.0467 0.6626
Plasmodium falciparum histone acetyltransferase GCN5 0.0038 0.0116 0.0337
Trichomonas vaginalis maltase-glucoamylase, putative 0.0033 0.0076 0.0314
Entamoeba histolytica phosphofructokinase, putative 0.0106 0.0642 1
Trichomonas vaginalis phosphofructokinase, putative 0.0106 0.0642 0.5596
Brugia malayi GMP synthase 0.0033 0.0079 0.0287
Trypanosoma cruzi calpain cysteine peptidase, putative 0.0109 0.0667 1
Brugia malayi 6-phosphofructokinase 0.0106 0.0642 0.232
Echinococcus multilocularis dihydrofolate reductase 0.0175 0.1174 0.4076
Trichomonas vaginalis neutral alpha-glucosidase ab precursor, putative 0.0033 0.0076 0.0314
Echinococcus granulosus histone acetyltransferase KAT2B 0.0042 0.0143 0.0247
Trichomonas vaginalis alpha-glucosidase, putative 0.0033 0.0076 0.0314
Echinococcus granulosus 6 phosphofructokinase 0.0106 0.0642 0.2102
Schistosoma mansoni glutamine-dependent NAD(+) synthetase 0.0083 0.0467 0.1452
Mycobacterium ulcerans 6-phosphofructokinase 0.0106 0.0642 0.0642
Plasmodium falciparum glutamine-dependent NAD(+) synthetase, putative 0.0083 0.0467 0.1952
Trypanosoma cruzi cysteine peptidase, Clan CA, family C2, putative 0.0109 0.0667 1
Toxoplasma gondii histone lysine acetyltransferase GCN5-B 0.0042 0.0143 0.2359
Loa Loa (eye worm) hypothetical protein 0.0033 0.0076 0.0276
Mycobacterium ulcerans 3-oxoacyl-ACP synthase 0.0309 0.2218 0.2218
Echinococcus multilocularis 6 phosphofructokinase 0.0106 0.0642 0.2102
Echinococcus multilocularis lysosomal alpha glucosidase 0.0343 0.2483 0.8938
Trichomonas vaginalis alpha-glucosidase, putative 0.0033 0.0076 0.0314
Leishmania major calpain-like cysteine peptidase, putative,cysteine peptidase, Clan CA, family C2, putative 0.0109 0.0667 1
Leishmania major calpain-like cysteine peptidase, putative,cysteine peptidase, Clan CA, family C2, putative 0.0109 0.0667 1
Mycobacterium ulcerans NAD synthetase 0.0083 0.0467 0.0467
Trichomonas vaginalis phosphofructokinase, putative 0.0106 0.0642 0.5596
Echinococcus granulosus histone acetyltransferase KAT2B 0.0137 0.0885 0.3005
Trypanosoma cruzi calpain-like cysteine peptidase, putative 0.0109 0.0667 1
Mycobacterium leprae PROBABLE GLUTAMINE-DEPENDENT NAD(+) SYNTHETASE NADE (NAD(+) SYNTHASE [GLUTAMINE-HYDROLYSING]) 0.0083 0.0467 0.3981
Trypanosoma cruzi NAD+ synthase, putative 0.0083 0.0467 0.6626
Schistosoma mansoni 6-phosphofructokinase 0.0106 0.0642 0.2102
Brugia malayi Alpha-L-fucosidase family protein 0.038 0.2769 1
Echinococcus granulosus lysosomal alpha glucosidase 0.0343 0.2483 0.8938
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0175 0.1174 1
Leishmania major ATP-dependent phosphofructokinase 0.0106 0.0642 0.9636
Trichomonas vaginalis nh(3)-dependent NAD(+) synthetase, putative 0.0083 0.0467 0.3964
Treponema pallidum NAD synthetase 0.0083 0.0467 0.7084
Loa Loa (eye worm) glycosyl hydrolase family 31 protein 0.0033 0.0076 0.0276
Trichomonas vaginalis alpha-glucosidase, putative 0.0033 0.0076 0.0314
Echinococcus multilocularis arachidonate 5 lipoxygenase 0.0054 0.0238 0.06
Entamoeba histolytica fatty acid elongase, putative 0.004 0.0132 0.2058
Trichomonas vaginalis alpha-L-fucosidase, putative 0.0167 0.1114 1
Plasmodium vivax beta-ketoacyl-acyl carrier protein synthase III precursor, putative 0.0309 0.2218 1
Trypanosoma brucei hypothetical protein 0.0109 0.0667 1
Leishmania major GMP synthase, putative,glutamine amidotransferase, putative 0.0033 0.0079 0.1191
Loa Loa (eye worm) 6-phosphofructokinase 0.0106 0.0642 0.232
Echinococcus multilocularis GMP synthase (glutamine hydrolyzing) 0.0033 0.0079 0.0011
Trichomonas vaginalis alpha-glucosidase, putative 0.0033 0.0076 0.0314
Trichomonas vaginalis alpha-L-fucosidase, putative 0.0167 0.1114 1
Echinococcus granulosus dihydrofolate reductase 0.0175 0.1174 0.4076
Trypanosoma brucei calpain-like cysteine peptidase, putative 0.0109 0.0667 1
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0175 0.1174 0.1174
Echinococcus multilocularis fucosidase, alpha L 1, tissue 0.038 0.2769 1
Loa Loa (eye worm) alpha-L-fucosidase 0.038 0.2769 1
Trichomonas vaginalis phosphofructokinase, putative 0.0106 0.0642 0.5596
Echinococcus multilocularis lysosomal alpha glucosidase 0.0343 0.2483 0.8938
Plasmodium falciparum GMP synthase [glutamine-hydrolyzing] 0.0033 0.0079 0.0168
Trypanosoma brucei calpain-like protein, putative 0.0109 0.0667 1
Schistosoma mansoni 6-phosphofructokinase 0.0106 0.0642 0.2102
Leishmania major NAD synthase, putative 0.0083 0.0467 0.7013
Toxoplasma gondii glycosyl hydrolase, family 31 protein 0.0033 0.0076 0.0793
Leishmania major calpain-like cysteine peptidase, putative,cysteine peptidase, Clan CA, family C2, putative 0.0109 0.0667 1
Brugia malayi Dihydrofolate reductase 0.0175 0.1174 0.424
Toxoplasma gondii bifunctional GMP synthase/glutamine amidotransferase protein 0.0033 0.0079 0.0862
Trypanosoma brucei calpain, putative 0.0109 0.0667 1
Entamoeba histolytica acetyltransferase, GNAT family 0.0038 0.0116 0.1808
Leishmania major glycosyl hydrolase-like protein 0.0033 0.0076 0.1147
Trichomonas vaginalis neutral alpha-glucosidase ab precursor, putative 0.0033 0.0076 0.0314
Toxoplasma gondii glutamine-dependent NAD(+) synthetase protein, putative 0.0083 0.0467 1
Echinococcus multilocularis gcn5proteinral control of amino acid synthesis 0.0141 0.0916 0.3119
Trichomonas vaginalis bromodomain-containing protein, putative 0.0042 0.0143 0.0935
Trichomonas vaginalis phosphofructokinase, putative 0.0106 0.0642 0.5596
Trichomonas vaginalis alpha-glucosidase, putative 0.0033 0.0076 0.0314
Schistosoma mansoni gcn5proteinral control of amino-acid synthesis 5-like 2 gcnl2 0.0141 0.0916 0.3119
Loa Loa (eye worm) acetyltransferase 0.0141 0.0916 0.3309
Giardia lamblia Histone acetyltransferase GCN5 0.0038 0.0116 0.1727
Toxoplasma gondii histone lysine acetyltransferase GCN5-A 0.0042 0.0143 0.2359
Entamoeba histolytica phosphofructokinase, putative 0.0106 0.0642 1
Trichomonas vaginalis alpha-glucosidase, putative 0.0033 0.0076 0.0314
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0067 0.0338 0.6958
Echinococcus granulosus arachidonate 5 lipoxygenase 0.0054 0.0238 0.06
Mycobacterium tuberculosis Probable 6-phosphofructokinase PfkA (phosphohexokinase) (phosphofructokinase) 0.0106 0.0642 0.0642
Chlamydia trachomatis oxoacyl-ACP synthase III 0.0309 0.2218 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C2, putative 0.0109 0.0667 1
Mycobacterium ulcerans GMP synthase 0.0033 0.0079 0.0079
Entamoeba histolytica pyrophosphate-dependent phosphofructokinase 0.0029 0.0043 0.0666
Trichomonas vaginalis alpha-glucosidase, putative 0.0033 0.0076 0.0314
Entamoeba histolytica glycosyl hydrolase, family 31 protein 0.0033 0.0076 0.119
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0067 0.0338 0.4436
Schistosoma mansoni dihydrofolate reductase 0.0175 0.1174 0.4076
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0067 0.0338 0.4436
Brugia malayi Glycosyl hydrolases family 31 protein 0.0343 0.2483 0.8967
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0067 0.0338 0.1358
Trichomonas vaginalis neutral alpha-glucosidase ab precursor, putative 0.0033 0.0076 0.0314
Trypanosoma brucei calpain-like cysteine peptidase, putative 0.0109 0.0667 1
Brugia malayi Glycosyl hydrolases family 31 protein 0.0033 0.0076 0.0276
Loa Loa (eye worm) phosphofructokinase 0.0106 0.0642 0.232
Loa Loa (eye worm) dihydrofolate reductase 0.0175 0.1174 0.424
Schistosoma mansoni glutamine-dependent NAD(+) synthetase 0.005 0.0209 0.0492
Trypanosoma cruzi calpain-like cysteine peptidase, putative 0.0109 0.0667 1
Trichomonas vaginalis sucrase-isomaltase, putative 0.0033 0.0076 0.0314
Mycobacterium ulcerans arylamine N-acetyltransferase Nat 0.1313 1 1
Brugia malayi acetyltransferase, GNAT family protein 0.0141 0.0916 0.3309
Trypanosoma brucei ATP-dependent 6-phosphofructokinase, glycosomal 0.0106 0.0642 0.9589
Entamoeba histolytica fatty acid elongase, putative 0.004 0.0132 0.2058
Trichomonas vaginalis alpha-glucosidase, putative 0.0033 0.0076 0.0314
Loa Loa (eye worm) 6-phosphofructokinase 0.0106 0.0642 0.232
Brugia malayi 6-phosphofructokinase 0.0106 0.0642 0.232
Entamoeba histolytica phosphofructokinase, putative 0.0106 0.0642 1
Leishmania major alpha glucosidase II subunit, putative 0.0033 0.0076 0.1147
Trichomonas vaginalis neutral alpha-glucosidase ab precursor, putative 0.0033 0.0076 0.0314
Schistosoma mansoni GMP synthetase 0.0033 0.0079 0.0011

Activities

Activity type Activity value Assay description Source Reference
ED2 (ADMET) = 0.11 mg kg-1 Oral dose necessary to produce an excretion of 2 mequiv of Na+/kg in the rat urine in the 4-h period after peroral administration ChEMBL. 6502592
ED2 (functional) = 0.12 mg kg-1 Natriuretic potency was evaluated as oral dose required to produce an excretion of 2 mequiv of Na+/Kg of rat body weight, ED2 value based on N=4 rats/dose ChEMBL. 3989818
ED5 (functional) = 0.11 mg kg-1 Natriuretic potency was evaluated as oral dose required to produce an excretion of 2 mequiv of Na+/Kg of dog body weight, ED5 value based on N=2 dogs/dose ChEMBL. 3989818
FD (functional) = 8.1 % Fractional delivery of Na+ to puncture site (percent of filtered load) of late distal tubular segments in the exposed kidney ChEMBL. 3989818
FD (functional) = 13.6 % Fractional delivery of Na+ to puncture site (percent of filtered load) of early distal tubular segments in the exposed kidney ChEMBL. 3989818
FD (functional) = 23 % Fractional delivery of K+ to puncture site (percent of filtered load) of early distal tubular segments in the exposed kidney ChEMBL. 3989818
FD (functional) = 23.6 % Fractional delivery of K+ to puncture site (percent of filtered load) of late distal tubular segments in the exposed kidney ChEMBL. 3989818
FE (functional) = 6.3 % Fractional excretion of Na+ (percent of filtered load) in rat ChEMBL. 3989818
FE (functional) = 54.6 % Fractional excretion of K+ (percent of filtered load) in rat ChEMBL. 3989818
GFR (functional) = 0.46 ml min-1 Glomerular filtration rate (per one kidney) per 100 g body weight of rat ChEMBL. 3989818
N (functional) = 11 Ratio of number of tubules/number of rats of early distal tubular segments in the exposed kidney ChEMBL. 3989818
Plasma (functional) = 3.57 mM K+ concentration in plasma sample of rat ChEMBL. 3989818
Plasma (functional) = 144 mM Na+ concentration in plasma sample of rat ChEMBL. 3989818
Rate (functional) = 4.6 nl min-1 Urine flow rate of late distal tubular segments in the exposed kidney ChEMBL. 3989818
Rate (functional) = 8.2 nl min-1 Urine flow rate of early distal tubular segments in the exposed kidney ChEMBL. 3989818
Rate (functional) = 67.6 ul min-1 Urine flow rate per kidney was evaluated in rat ChEMBL. 3989818
Ratio (functional) = 8 Ratio of number of tubules/number of rats of late distal tubular segments in the exposed kidney ChEMBL. 3989818
SNGFR (functional) = 33.9 nl min-1 Single nephron glomerular filtration rate of late distal tubular segments in the exposed kidney ChEMBL. 3989818
SNGFR (functional) = 35.7 nl min-1 Single nephron glomerular filtration rate of early distal tubular segments in the exposed kidney ChEMBL. 3989818
TF/P (functional) = 4.39 Tubular fluid-to-plasma concentration ratio for inulin of early distal tubular segments in the exposed kidney ChEMBL. 3989818
TF/P (functional) = 8.48 Tubular fluid-to-plasma concentration ratio for inulin of late distal tubular segments in the exposed kidney ChEMBL. 3989818
U/P (functional) = 19.7 Urine-to-plasma concentration ratio for inulin in rat ChEMBL. 3989818

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

2 literature references were collected for this gene.

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