Detailed information for compound 227821

Basic information

Technical information
  • TDR Targets ID: 227821
  • Name: methyl 3-chloro-5-[1-(3-chloro-4-methoxy-5-me thoxycarbonylphenyl)-6-ethoxy-6-oxohex-1-enyl ]-2-methoxybenzoate
  • MW: 539.402 | Formula: C26H28Cl2O8
  • H donors: 0 H acceptors: 3 LogP: 6.16 Rotable bonds: 14
    Rule of 5 violations (Lipinski): 2
  • SMILES: CCOC(=O)CCCC=C(c1cc(Cl)c(c(c1)C(=O)OC)OC)c1cc(Cl)c(c(c1)C(=O)OC)OC
  • InChi: 1S/C26H28Cl2O8/c1-6-36-22(29)10-8-7-9-17(15-11-18(25(30)34-4)23(32-2)20(27)13-15)16-12-19(26(31)35-5)24(33-3)21(28)14-16/h9,11-14H,6-8,10H2,1-5H3
  • InChiKey: LGVOXUUNQUMZBN-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • methyl 3-chloro-5-[1-(3-chloro-4-methoxy-5-methoxycarbonyl-phenyl)-6-ethoxy-6-oxo-hex-1-enyl]-2-methoxy-benzoate
  • 3-chloro-5-[1-(3-chloro-4-methoxy-5-methoxycarbonylphenyl)-6-ethoxy-6-oxohex-1-enyl]-2-methoxybenzoic acid methyl ester
  • 5-[1-(3-carbomethoxy-5-chloro-4-methoxy-phenyl)-6-ethoxy-6-keto-hex-1-enyl]-3-chloro-2-methoxy-benzoic acid methyl ester
  • Ethyl 6,6-bis[3-chloro-4-methoxy-5-(methoxycarbonyl)phenyl]hex-5-enoate
  • Alkenyldiarylmethanes (ADAM) 19a
  • AIDS-165202
  • AIDS165202

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Plasmodium yoelii integrase-related Get druggable targets OG5_139608 All targets in OG5_139608
Trypanosoma brucei RNA helicase, putative Get druggable targets OG5_139608 All targets in OG5_139608
Trypanosoma congolense RNA helicase, putative Get druggable targets OG5_139608 All targets in OG5_139608
Schistosoma mansoni hypothetical protein Get druggable targets OG5_139608 All targets in OG5_139608
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 inositol-1(or 4)-monophosphatase 1, putative 0.0039 0.0104 0.0104
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0458 0.3763 1
Onchocerca volvulus Ribonuclease H1 homolog 0.0027 0 0.5
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0054 0.0236 0.0627
Loa Loa (eye worm) hypothetical protein 0.0423 0.3459 0.9085
Trypanosoma cruzi cAMP specific phosphodiesterase, putative 0.0054 0.0236 0.0236
Trypanosoma brucei hypothetical protein, conserved 0.0029 0.002 0.002
Trichomonas vaginalis cyclic nucleotide phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis high-affinity cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Toxoplasma gondii dihydroorotate dehydrogenase reveal, putative 0.1173 1 1
Trichomonas vaginalis cone cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis cyclic nucleotide phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis cAMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis rod cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trypanosoma cruzi dihydroorotate dehydrogenase, putative 0.1173 1 1
Loa Loa (eye worm) hypothetical protein 0.0462 0.3797 1
Trichomonas vaginalis cyclic nucleotide phosphodiesterase, putative 0.0054 0.0236 0.0627
Echinococcus multilocularis cAMP and cAMP inhibited cGMP 3',5' cyclic 0.0477 0.3928 1
Brugia malayi 3'5'-cyclic nucleotide phosphodiesterase family protein 0.0054 0.0236 0.0236
Schistosoma mansoni cgmp-dependent 35-cyclic phosphodiesterase 0.0054 0.0236 0.0236
Trichomonas vaginalis cGMP-dependent 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Brugia malayi Dihydroorotate dehydrogenase, mitochondrial precursor, putative 0.1173 1 1
Trichomonas vaginalis cAMP-specific phosphodiesterase, putative 0.0054 0.0236 0.0627
Echinococcus granulosus dual 3'5' cyclic AMP and GMP phosphodiesterase 0.0054 0.0236 0.0601
Schistosoma mansoni camp/cgmp cyclic nucleotide phosphodiesterase 0.0054 0.0236 0.0236
Trichomonas vaginalis cGMP-inhibited 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis conserved hypothetical protein 0.0039 0.0105 0.028
Trypanosoma brucei RNA helicase, putative 0.01 0.064 0.064
Trypanosoma brucei retrotransposon hot spot protein 4 (RHS4), interrupted 0.0029 0.002 0.002
Trypanosoma brucei dihydroorotate dehydrogenase (fumarate) 0.1173 1 1
Trypanosoma brucei cAMP-specific phosphodiesterase 0.0054 0.0236 0.0236
Brugia malayi follicle stimulating hormone receptor 0.0242 0.1876 0.1876
Toxoplasma gondii hypothetical protein 0.0039 0.0105 0.0105
Trypanosoma brucei cAMP-specific phosphodiesterase 0.0054 0.0236 0.0236
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis myo inositol monophosphatase, putative 0.0039 0.0104 0.0276
Leishmania major dihydroorotate dehydrogenase 0.1173 1 1
Entamoeba histolytica dihydropyrimidine dehydrogenase, putative 0.0458 0.3763 1
Mycobacterium tuberculosis Two component sensor histidine kinase DosT 0.0039 0.0105 0.0037
Trichomonas vaginalis high-affinity cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Echinococcus granulosus inositol monophosphatase 1 0.0039 0.0104 0.0264
Toxoplasma gondii hypothetical protein 0.0039 0.0105 0.0105
Echinococcus multilocularis dihydropyrimidine dehydrogenase (NADP+) 0.0458 0.3763 0.9581
Wolbachia endosymbiont of Brugia malayi fructose-1,6-bisphosphatase 0.0039 0.0104 0.0104
Trypanosoma cruzi cAMP specific phosphodiesterase, putative 0.0054 0.0236 0.0236
Toxoplasma gondii GAF domain-containing protein 0.0039 0.0105 0.0105
Treponema pallidum ribonuclease H (rnhA) 0.0027 0 0.5
Schistosoma mansoni dihydroorotate dehydrogenase 0.1173 1 1
Echinococcus multilocularis dual 3',5' cyclic AMP and GMP phosphodiesterase 0.0054 0.0236 0.0601
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0054 0.0236 0.0627
Trypanosoma cruzi myo-inositol-1(or 4)-monophosphatase 1, putative 0.0039 0.0104 0.0104
Brugia malayi Zinc finger, C2H2 type family protein 0.0458 0.3763 0.3763
Schistosoma mansoni inositol monophosphatase 0.0039 0.0104 0.0104
Mycobacterium ulcerans dihydroorotate dehydrogenase 2 0.1173 1 1
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0054 0.0236 0.0627
Schistosoma mansoni hypothetical protein 0.01 0.064 0.064
Loa Loa (eye worm) hypothetical protein 0.0054 0.0236 0.0358
Giardia lamblia Ribonuclease H 0.0027 0 0.5
Trichomonas vaginalis cone cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Mycobacterium ulcerans putative regulatory protein 0.0039 0.0105 0.0002
Trypanosoma cruzi dihydroorotate dehydrogenase, putative 0.1173 1 1
Trichomonas vaginalis cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis conserved hypothetical protein 0.0039 0.0105 0.028
Plasmodium falciparum dihydroorotate dehydrogenase 0.1173 1 1
Toxoplasma gondii hypothetical protein 0.0039 0.0105 0.0105
Wolbachia endosymbiont of Brugia malayi dihydroorotate dehydrogenase 2 0.1173 1 1
Trypanosoma brucei unspecified product 0.0029 0.002 0.002
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0458 0.3763 1
Trichomonas vaginalis conserved hypothetical protein 0.0039 0.0105 0.028
Trichomonas vaginalis high-affinity cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis high-affinity cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis cAMP-specific phosphodiesterase, putative 0.0054 0.0236 0.0627
Trypanosoma brucei ingi protein (ORF1) 0.0029 0.002 0.002
Trichomonas vaginalis conserved hypothetical protein 0.0054 0.0236 0.0627
Trypanosoma cruzi myo-inositol-1(or 4)-monophosphatase 1, putative 0.0039 0.0104 0.0104
Leishmania major myo-inositol-1(or 4)-monophosphatase 1, putative 0.0039 0.0104 0.0104
Trichomonas vaginalis high-affinity cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trypanosoma brucei ingi protein (ORF1) 0.0029 0.002 0.002
Trichomonas vaginalis cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Echinococcus granulosus cAMP and cAMP inhibited cGMP 3'5' cyclic 0.0477 0.3928 1
Mycobacterium leprae Probable dihydroorotate dehydrogenase PyrD 0.1173 1 1
Mycobacterium ulcerans putative regulatory protein 0.0039 0.0105 0.0002
Loa Loa (eye worm) follicle stimulating hormone receptor 0.0242 0.1876 0.4799
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0458 0.3763 1
Echinococcus multilocularis dihydropyrimidine dehydrogenase (NADP+) 0.0458 0.3763 0.9581
Brugia malayi Probable 3',5'-cyclic phosphodiesterase C32E12.2, putative 0.0477 0.3928 0.3928
Trichomonas vaginalis rod cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Mycobacterium tuberculosis Probable dihydroorotate dehydrogenase PyrD 0.1173 1 1
Mycobacterium leprae conserved hypothetical protein 0.0039 0.0105 0.0037
Trichomonas vaginalis cGMP-dependent 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis cGMP-dependent 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Schistosoma mansoni inositol monophosphatase 0.0039 0.0104 0.0104
Trichomonas vaginalis myo inositol monophosphatase, putative 0.0039 0.0104 0.0276
Trichomonas vaginalis cAMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0458 0.3763 1
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0054 0.0236 0.0627
Trichomonas vaginalis conserved hypothetical protein 0.0039 0.0105 0.028
Trichomonas vaginalis inositol monophosphatase, putative 0.0039 0.0104 0.0276
Trichomonas vaginalis dihydropyrimidine dehydrogenase, putative 0.0458 0.3763 1
Toxoplasma gondii inositol(myo)-1(or 4)-monophosphatase 2, putative 0.0039 0.0104 0.0104
Echinococcus granulosus dihydropyrimidine dehydrogenase NADP 0.0458 0.3763 0.9581
Mycobacterium tuberculosis Two component sensor histidine kinase DevS 0.0039 0.0105 0.0037
Echinococcus granulosus dihydropyrimidine dehydrogenase NADP 0.0458 0.3763 0.9581
Trichomonas vaginalis cAMP/cGMP cyclic nucleotide phosphodiesterase, putative 0.0054 0.0236 0.0627
Mycobacterium ulcerans two component sensor histidine kinase DevS 0.0039 0.0105 0.0002
Plasmodium vivax dihydroorotate dehydrogenase, mitochondrial precursor, putative 0.1173 1 1
Trichomonas vaginalis cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Trypanosoma cruzi dihydroorotate dehydrogenase (fumarate), putative 0.1173 1 1
Trypanosoma cruzi cAMP specific phosphodiesterase, putative 0.0054 0.0236 0.0236
Trichomonas vaginalis rod cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0054 0.0236 0.0627
Echinococcus multilocularis inositol monophosphatase 1 0.0039 0.0104 0.0264
Brugia malayi Inositol-1 0.0039 0.0104 0.0104
Trypanosoma cruzi dihydroorotate dehydrogenase, putative 0.0458 0.3763 0.3763
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0458 0.3763 1

Activities

Activity type Activity value Assay description Source Reference
CC50 (functional) = 16 uM Concentration required for cytotoxicity against mock infected CEM-SS cells ChEMBL. 11708913
CC50 (functional) = 16 uM Concentration required for cytotoxicity against mock infected CEM-SS cells ChEMBL. 11708913
EC50 (functional) = 0.01 uM Inhibitory concentration for cytopathicity of HIV-1RF in CEM-SS cells ChEMBL. 11708913
IC50 (functional) = 0.013 uM Antiviral activity against site directed resistant isolates in HIV-1 A98G CEM cells ChEMBL. 11708913
IC50 (functional) = 0.013 uM Antiviral activity against site directed resistant isolates in HIV-1 A98G CEM cells ChEMBL. 11708913
IC50 (functional) = 0.076 uM Antiviral activity against site directed 4X AZT resistant isolate HIV-1 in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.076 uM Antiviral activity against site directed 4X AZT resistant isolate HIV-1 in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.08 uM Antiviral activity against site directed resistant isolate HIV-1 L100I in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.08 uM Antiviral activity against site directed resistant isolate HIV-1 L100I in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.15 uM Antiviral activity against subtype isolate D strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 0.164 uM Antiviral activity against site directed resistant isolate HIV-1 K101E in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.164 uM Antiviral activity against site directed resistant isolate HIV-1 K101E in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.2 uM Antiviral activity against subtype isolate A strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 0.2 uM Antiviral activity against subtype isolate E strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (binding) = 0.233 uM Inhibitory activity against HIV-1 Reverse Transcriptase with rCdG as the template primer ChEMBL. 11708913
IC50 (binding) = 0.233 uM Inhibitory activity against HIV-1 Reverse Transcriptase with rCdG as the template primer ChEMBL. 11708913
IC50 (functional) = 0.27 uM Antiviral activity against site directed resistant isolate HIV-1 K103N in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.27 uM Antiviral activity against site directed resistant isolate HIV-1 K103N in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.3 uM Antiviral activity against subtype isolate F strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 0.37 uM Antiviral activity against site directed 4X AZT resistant isolate HIV-1 L100I in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.37 uM Antiviral activity against site directed 4X AZT resistant isolate HIV-1 L100I in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.39 uM Antiviral activity against ROJO virus strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 0.58 uM Antiviral activity against site directed wild-type enzyme isolate HIV-1 NL4-3WT in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.58 uM Antiviral activity against site directed wild-type enzyme isolate HIV-1 NL4-3WT in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.7 uM Antiviral activity against WEJO virus strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 0.8 uM Antiviral activity against subtype isolate G strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 0.82 uM Antiviral activity against subtype isolate C strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 0.885 uM Antiviral activity against site directed resistant isolate HIV-1 L74V in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.885000000000002 uM Antiviral activity against site directed resistant isolate HIV-1 L74V in CEM cells ChEMBL. 11708913
IC50 (functional) = 0.9 uM Antiviral activity against SLKA virus strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 1 uM Antiviral activity against TEKI virus strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 2.3 uM Antiviral activity against site directed resistant isolate HIV-1 V179D in CEM cells ChEMBL. 11708913
IC50 (functional) = 2.3 uM Antiviral activity against site directed resistant isolate HIV-1 V179D in CEM cells ChEMBL. 11708913
IC50 (functional) = 4.1 uM Antiviral activity against site directed resistant isolate HIV-1 Y188C in CEM cells ChEMBL. 11708913
IC50 (functional) = 4.1 uM Antiviral activity against site directed resistant isolate HIV-1 Y188C in CEM cells ChEMBL. 11708913
IC50 (functional) = 8.9 uM Antiviral activity against Ba-L monocyte tropic isolate strain in monocyte ChEMBL. 11708913
IC50 (functional) = 10.3 uM Antiviral activity against site directed resistant isolate HIV-1 V106A in CEM cells ChEMBL. 11708913
IC50 (functional) = 10.3 uM Antiviral activity against site directed resistant isolate HIV-1 V106A in CEM cells ChEMBL. 11708913
IC50 (functional) = 12.5 uM Antiviral activity against subtype isolate B strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 19.1 uM Antiviral activity against site directed resistant isolate HIV-1 Y181C in CEM cells ChEMBL. 11708913
IC50 (functional) = 19.1 uM Antiviral activity against site directed resistant isolate HIV-1 Y181C in CEM cells ChEMBL. 11708913
IC50 (functional) = 30 uM Antiviral activity against subtype isolate O strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
IC50 (functional) = 45.2 uM Antiviral activity against multi drug resistant MDR 769 strain in PBLs (peripheral blood lymphocytes) ChEMBL. 11708913
TI (ADMET) = 1600 Ratio of CC50/EC50 was determined ChEMBL. 11708913

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 11708913

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

1 literature reference was collected for this gene.

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