TDR Targets

Basic information

Technical information

TDR Targets ID: 69154
Name: ethyl (E)-6-[1-[(4-chlorophenyl)methyl]pyrrol -2-yl]-2,4-dioxohex-5-enoate
MW: 359.804 | Formula: C19H18ClNO4
H donors: 0 H acceptors: 3 LogP: 3.3 Rotable bonds: 9
Rule of 5 violations (Lipinski): 1
SMILES: CCOC(=O)C(=O)CC(=O)/C=C/c1cccn1Cc1ccc(cc1)Cl
InChi: 1S/C19H18ClNO4/c1-2-25-19(24)18(23)12-17(22)10-9-16-4-3-11-21(16)13-14-5-7-15(20)8-6-14/h3-11H,2,12-13H2,1H3/b10-9+
InChiKey: ZCILPXHVBKEIQK-MDZDMXLPSA-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

ethyl (E)-6-[1-[(4-chlorophenyl)methyl]pyrrol-2-yl]-2,4-dioxo-hex-5-enoate
(E)-6-[1-[(4-chlorophenyl)methyl]-2-pyrrolyl]-2,4-dioxo-5-hexenoic acid ethyl ester
(E)-6-[1-(4-chlorobenzyl)pyrrol-2-yl]-2,4-diketo-hex-5-enoic acid ethyl ester

Targets

Known targets for this compound

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

Predicted pathogen targets for this compound

By orthology

Species	Potential target	Known druggable target/s	Ortholog Group
Trypanosoma congolense	RNA helicase, putative	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
Plasmodium yoelii	integrase-related	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

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Echinococcus multilocularis	RNA directed DNA polymerase (reverse transcriptase)	Reverse transcriptase	259 aa	227 aa	26.4 %
Dictyostelium discoideum	hypothetical protein	Reverse transcriptase	259 aa	222 aa	22.5 %
Echinococcus multilocularis	RNA directed DNA polymerase (reverse transcriptase)	Reverse transcriptase	259 aa	208 aa	26.4 %
Dictyostelium discoideum	hypothetical protein	Reverse transcriptase	259 aa	226 aa	24.3 %
Trypanosoma congolense	Retroviral aspartyl protease/Reverse transcriptase (RNA-dependent DNA polymerase)/RNase H, putative	Reverse transcriptase	259 aa	237 aa	29.1 %
Dictyostelium discoideum	hypothetical protein	Reverse transcriptase	259 aa	245 aa	25.7 %
Candida albicans	polyprotein of retrotransposon Tca8	Reverse transcriptase	259 aa	238 aa	26.5 %
Candida albicans	hypothetical protein	Reverse transcriptase	259 aa	223 aa	29.1 %
Candida albicans	ReverseTranscriptase similar to fruit fly Tom element	Reverse transcriptase	259 aa	244 aa	27.9 %
Echinococcus multilocularis	RNA directed DNA polymerase (reverse transcriptase)	Reverse transcriptase	259 aa	227 aa	26.4 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Mycobacterium ulcerans	membrane-anchored mycosin MycP3	0.0032	0.0111	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0032	0.0111	0.0289
Echinococcus multilocularis	Furin 1	0.02	0.2297	0.2275
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Echinococcus multilocularis	neuroendocrine convertase 2	0.0493	0.6113	0.6102
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Schistosoma mansoni	hypothetical protein	0.0792	1	1
Mycobacterium ulcerans	membrane-anchored serine protease (mycosin), MycP4	0.0032	0.0111	0.5
Schistosoma mansoni	hypothetical protein	0.0309	0.3717	0.3671
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Giardia lamblia	Furin precursor putative serine protease	0.0168	0.1881	1
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Brugia malayi	Hypothetical subtilase-type proteinase F21H12.6 in chromosome II	0.0032	0.0111	0.0049
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Brugia malayi	Subtilase family protein	0.0032	0.0111	0.0049
Trichomonas vaginalis	conserved hypothetical protein	0.0032	0.0111	0.0289
Trichomonas vaginalis	conserved hypothetical protein	0.0032	0.0111	0.0289
Loa Loa (eye worm)	endoprotease bli-4	0.0611	0.764	1
Plasmodium falciparum	subtilisin-like protease 2	0.0032	0.0111	1
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Brugia malayi	celfurPC protein	0.0466	0.5758	0.7141
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Brugia malayi	Furin-like cysteine rich region family protein	0.0123	0.129	0.1529
Toxoplasma gondii	subtilisin SUB11	0.0032	0.0111	1
Trypanosoma brucei	serine peptidase, clan SB, family S8-like protein	0.0032	0.0111	0.0219
Loa Loa (eye worm)	hypothetical protein	0.0317	0.3816	0.4947
Trypanosoma cruzi	subtilisin-like serine peptidase, putative	0.0032	0.0111	1
Trichomonas vaginalis	hypothetical protein	0.0145	0.1577	0.4124
Echinococcus multilocularis		0.0466	0.5758	0.5746
Echinococcus granulosus	peptidase s8 s53 subtilisin kexin sedolisin	0.0032	0.0111	0.0083
Toxoplasma gondii	subtilisin SUB12	0.0032	0.0111	1
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Trypanosoma cruzi	subtilisin-like serine peptidase, putative	0.0032	0.0111	1
Plasmodium vivax	subtilisin-like serine protease, putative	0.0032	0.0111	1
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Mycobacterium tuberculosis	Probable alanine and proline rich membrane-anchored mycosin MycP2 (serine protease) (subtilisin-like protease) (subtilase-like)	0.0032	0.0111	0.5
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Brugia malayi	RNA, U transporter 1	0.0082	0.0767	0.0872
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.02	0.2297	0.6007
Toxoplasma gondii	subtilisin SUB8	0.0032	0.0111	1
Plasmodium falciparum	subtilisin-like protease 3	0.0032	0.0111	1
Echinococcus multilocularis	membrane bound transcription factor site 1	0.0032	0.0111	0.0083
Brugia malayi	endoprotease bli-4 precursor	0.0611	0.764	0.9504
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Loa Loa (eye worm)	hypothetical protein	0.0171	0.1921	0.2443
Entamoeba histolytica	hypothetical protein	0.0023	0.0001	0.5
Schistosoma mansoni	tyrosine kinase	0.0123	0.129	0.1226
Brugia malayi	proprotein convertase 2	0.0493	0.6113	0.7587
Echinococcus granulosus	Furin 1	0.02	0.2297	0.2275
Brugia malayi	neuroendocrine convertase 1 precursor	0.0641	0.8035	1
Trichomonas vaginalis	conserved hypothetical protein	0.0032	0.0111	0.0289
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Brugia malayi	Membrane-bound transcription factor site-1 protease precursor	0.0032	0.0111	0.0049
Leishmania major	subtilisin-like serine peptidase	0.0032	0.0111	1
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.02	0.2297	0.6007
Echinococcus granulosus	neuroendocrine convertase 2	0.0493	0.6113	0.6102
Echinococcus multilocularis	epidermal growth factor receptor	0.0123	0.129	0.1265
Schistosoma mansoni	hypothetical protein	0.0145	0.1577	0.1516
Loa Loa (eye worm)	hypothetical protein	0.0032	0.0111	0.0052
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0055	0.0415	0.1084
Toxoplasma gondii	subtilisin SUB6	0.0032	0.0111	1
Toxoplasma gondii	subtilisin SUB5	0.0032	0.0111	1
Toxoplasma gondii	subtilisin SUB1	0.0032	0.0111	1
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.02	0.2297	0.6007
Trichomonas vaginalis	leucine-rich repeat protein, BspA family	0.0145	0.1577	0.4124
Echinococcus multilocularis	dnaJ subfamily B	0.0792	1	1
Toxoplasma gondii	subtilisin SUB4	0.0032	0.0111	1
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Echinococcus multilocularis	tm gpcr rhodopsin gpcr rhodopsin superfamily	0.0522	0.6488	0.6478
Plasmodium vivax	subtilisin-like protease 1	0.0032	0.0111	1
Schistosoma mansoni	site-1 peptidase (S08 family)	0.0032	0.0111	0.0039
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Loa Loa (eye worm)	hypothetical protein	0.0611	0.764	1
Echinococcus granulosus	furin	0.0611	0.764	0.7633
Loa Loa (eye worm)	proprotein convertase 2	0.02	0.2297	0.294
Trypanosoma cruzi	serine peptidase, clan SB, family S8-like protein	0.0032	0.0111	1
Plasmodium falciparum	subtilisin-like protease 1	0.0032	0.0111	1
Plasmodium vivax	subtilisin-like protease 2, putative	0.0032	0.0111	1
Echinococcus granulosus	snurportin 1	0.0309	0.3717	0.3699
Echinococcus granulosus	epidermal growth factor receptor	0.0123	0.129	0.1265
Echinococcus granulosus	membrane bound transcription factor site 1	0.0032	0.0111	0.0083
Toxoplasma gondii	subtilisin SUB2	0.0032	0.0111	1
Toxoplasma gondii	subtilisin SUB7	0.0032	0.0111	1
Loa Loa (eye worm)	TK/EGFR protein kinase	0.0123	0.129	0.1609
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0317	0.3824	1
Toxoplasma gondii	subtilisin SUB10	0.0032	0.0111	1
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Loa Loa (eye worm)	nucleolar RNA-associated protein alpha	0.0309	0.3717	0.4816
Mycobacterium tuberculosis	Probable proline rich membrane-anchored mycosin MycP5 (serine protease) (subtilisin-like protease) (subtilase-like) (mycosin-5)	0.0032	0.0111	0.5
Trypanosoma brucei	subtilisin peptidase	0.0032	0.0111	0.0219
Echinococcus granulosus	importin subunit beta 1	0.0029	0.0072	0.0044
Mycobacterium tuberculosis	Probable membrane-anchored mycosin MycP3 (serine protease) (subtilisin-like protease) (subtilase-like) (mycosin-3)	0.0032	0.0111	0.5
Echinococcus multilocularis	snurportin 1	0.0309	0.3717	0.3699
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Schistosoma mansoni	subfamily S8B unassigned peptidase (S08 family)	0.0611	0.764	0.7623
Mycobacterium leprae	Possible secreted protease	0.0032	0.0111	0.5
Schistosoma mansoni	tripeptidyl-peptidase II (S08 family)	0.0032	0.0111	0.0039
Trichomonas vaginalis	proprotein convertase subtilisin/kexin type, putative	0.0168	0.1881	0.4919
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.02	0.2297	0.6007
Trichomonas vaginalis	conserved hypothetical protein	0.0032	0.0111	0.0289
Trypanosoma cruzi	subtilisin peptidase	0.0032	0.0111	1
Schistosoma mansoni	furin-1 (S08 family)	0.0325	0.3927	0.3883
Onchocerca volvulus		0.0032	0.0111	1
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Schistosoma mansoni	subfamily S8B non-peptidase homologue (S08 family)	0.02	0.2297	0.2241
Trypanosoma brucei	RNA helicase, putative	0.0167	0.1864	1
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.02	0.2297	0.6007
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Mycobacterium leprae	PROBABLE PROLINE RICH MEMBRANE-ANCHORED MYCOSIN MYCP5 (SERINE PROTEASE) (SUBTILISIN-LIKE PROTEASE) (SUBTILASE-LIKE) (MYCOSIN-5)	0.0032	0.0111	0.5
Schistosoma mansoni	subfamily S8B unassigned peptidase (S08 family)	0.0055	0.0415	0.0346
Echinococcus multilocularis	proprotein convertase subtilisin:kexin type 5	0.0317	0.3824	0.3806
Echinococcus multilocularis	importin subunit beta 1	0.0029	0.0072	0.0044
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Toxoplasma gondii	subtilisin SUB9	0.0032	0.0111	1
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.02	0.2297	0.6007
Mycobacterium leprae	PROBABLE MEMBRANE-ANCHORED MYCOSIN MYCP3 (SERINE PROTEASE) (SUBTILISIN-LIKE PROTEASE) (SUBTILASE-LIKE) (MYCOSIN-3)	0.0032	0.0111	0.5
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Echinococcus granulosus	proprotein convertase subtilisin:kexin type 5	0.0317	0.3824	0.3806
Echinococcus granulosus	tm gpcr rhodopsin	0.0522	0.6488	0.6478
Loa Loa (eye worm)	subtilase	0.0032	0.0111	0.0052
Trichomonas vaginalis	conserved hypothetical protein	0.0145	0.1577	0.4124
Echinococcus multilocularis	Peptidase S8 S53, subtilisin kexin sedolisin	0.0032	0.0111	0.0083
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0032	0.0111	0.0289
Schistosoma mansoni	hypothetical protein	0.0167	0.1864	0.1804
Trichomonas vaginalis	Clan SB, family S8, subtilisin-like serine peptidase	0.0317	0.3824	1
Mycobacterium tuberculosis	Probable membrane-anchored mycosin MycP4 (serine protease) (subtilisin-like protease) (subtilase-like) (mycosin-4)	0.0032	0.0111	0.5
Trichomonas vaginalis	neuroendocrine convertase 2 precursor, putative	0.0168	0.1881	0.4919
Schistosoma mansoni	site-1 peptidase (S08 family)	0.0032	0.0111	0.0039
Mycobacterium ulcerans	proline rich membrane-anchored mycosin MycP5	0.0032	0.0111	0.5

Activities

Activity type	Activity value	Assay description	Source	Reference
CC50 (ADMET)	> 50 uM	Cytotoxicity against human HeLa cells expressing CD4 after 24 hrs by beta-galactosidase reporter gene assay	ChEMBL.	24124919
CC50 (ADMET)	= 52 uM	Cytotoxic concentration required to reduce the viability of mock-infected cells was determined by using MTT assay	ChEMBL.	15026063
EC50 (functional)	> 52 uM	Effective concentration required to reduce the exponential growth of MT-4/KB cells	ChEMBL.	15026063
EC50 (functional)	> 52 uM	Effective concentration required to reduce the exponential growth of MT-4/KB cells	ChEMBL.	15026063
IC50 (binding)	= 8 uM	Inhibition of RNase H activity of recombinant HIV1 reverse transcriptase using poly(dC)-[3H]poly(rG) as substrate	ChEMBL.	24124919
IC50 (binding)	= 42 uM	Inhibition of strand transfer activity of recombinant HIV1 integrase using 5'-end-labeled 21-mer double-stranded DNA as substrate after 60 mins by electrochemiluminescent plate-based assay	ChEMBL.	24124919
IC50 (binding)	= 50 uM	Inhibitory activity against HIV-1 integrase.	ChEMBL.	15026063
IC50 (binding)	= 50 uM	Inhibitory activity against HIV-1 integrase.	ChEMBL.	15026063
IC50 (binding)	= 65 uM	Inhibitory activity against HIV-1 integrase.	ChEMBL.	15026063
IC50 (binding)	= 65 uM	Inhibitory activity against HIV-1 integrase.	ChEMBL.	15026063
S.I (functional)	0	Selectivity index of the compound was determined; ND=No data	ChEMBL.	15026063

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: CHEMBL417356
PubChem: 6479504

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 69154