TDR Targets

Basic information

Technical information

TDR Targets ID: 265364
Name: (3E,5E)-3,5-bis[(4-chlorophenyl)methylidene]p iperidin-4-one
MW: 344.235 | Formula: C19H15Cl2NO
H donors: 1 H acceptors: 1 LogP: 4.42 Rotable bonds: 2
Rule of 5 violations (Lipinski): 1
SMILES: O=C1/C(=C/c2ccc(cc2)Cl)/CNC/C/1=C\c1ccc(cc1)Cl
InChi: 1S/C19H15Cl2NO/c20-17-5-1-13(2-6-17)9-15-11-22-12-16(19(15)23)10-14-3-7-18(21)8-4-14/h1-10,22H,11-12H2/b15-9+,16-10+
InChiKey: LBNHBGZGFHYLAA-KAVGSWPWSA-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

(3E,5E)-3,5-bis[(4-chlorophenyl)methylene]piperidin-4-one
(3E,5E)-3,5-bis[(4-chlorophenyl)methylene]-4-piperidinone
(3E,5E)-3,5-bis(4-chlorobenzylidene)-4-piperidone
3,5-bis[(4-chlorophenyl)methylidene]piperidin-4-one
3,5-bis[(4-chlorophenyl)methylene]piperidin-4-one
3,5-bis[(4-chlorophenyl)methylene]-4-piperidinone
3,5-bis(4-chlorobenzylidene)-4-piperidone
NSC685124
Neuro_000421
NSC632838 (HYDROCHLORIDE SALT)
3,5-Bis(4-chlorobenzylidene)-4-piperidinone
AIDS-160491
AIDS160491
NCI60_010799
NCI60_030637
4-Piperidinone, 3,5-bis[(4-chlorophenyl)methylene]-, (E,E)-

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

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Echinococcus multilocularis	transmembrane protease serine 3	0.00533414	0.0263164	0.37661
Onchocerca volvulus		0.00533414	0.0263164	0.0263164
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.0285291	0.6733	1
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Loa Loa (eye worm)	hypothetical protein	0.00533414	0.0263164	0.0390857
Onchocerca volvulus		0.00533414	0.0263164	0.0263164
Loa Loa (eye worm)	trypsin family protein	0.00533414	0.0263164	0.0390857
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Plasmodium vivax	cysteine repeat modular protein 1, putative	0.00689584	0.0698771	0.5
Brugia malayi	Chymotrypsin-like protease CTRL-1 precursor	0.00533414	0.0263164	0.0390857
Loa Loa (eye worm)	TK/ROR protein kinase	0.00689584	0.0698771	0.103783
Leishmania major	hypothetical protein, conserved	0.00689584	0.0698771	0.5
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Schistosoma mansoni	aminopeptidase PILS (M01 family)	0.00533414	0.0263164	0.0390857
Brugia malayi	Trypsin family protein	0.0285291	0.6733	1
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.0285291	0.6733	1
Brugia malayi	Trypsin family protein	0.00533414	0.0263164	0.0390857
Onchocerca volvulus		0.023195	0.524513	0.524513
Schistosoma mansoni	hypothetical protein	0.00689584	0.0698771	0.103783
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.00533414	0.0263164	0.0390857
Brugia malayi	Kringle domain containing protein	0.00689584	0.0698771	0.103783
Loa Loa (eye worm)	hypothetical protein	0.0285291	0.6733	1
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.00533414	0.0263164	0.0390857
Brugia malayi	hypothetical protein	0.00533414	0.0263164	0.0390857
Giardia lamblia	High cysteine protein	0.00439068	0	0.5
Loa Loa (eye worm)	variant SH3 domain-containing protein	0.0111874	0.189582	0.281572
Plasmodium falciparum	cysteine repeat modular protein 1	0.00689584	0.0698771	0.5
Brugia malayi	Trypsin-like protease protein 5	0.00533414	0.0263164	0.0390857
Toxoplasma gondii	PAN domain-containing protein	0.0309062	0.739606	1
Loa Loa (eye worm)	hypothetical protein	0.00533414	0.0263164	0.0390857
Echinococcus granulosus	transmembrane protease serine 3	0.00533414	0.0263164	0.37661
Onchocerca volvulus		0.00533414	0.0263164	0.0263164
Echinococcus multilocularis	subfamily S1A unassigned peptidase (S01 family)	0.00533414	0.0263164	0.37661
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.00533414	0.0263164	0.0390857
Echinococcus multilocularis	Mastin	0.00533414	0.0263164	0.37661
Loa Loa (eye worm)	hypothetical protein	0.00689584	0.0698771	0.103783
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Loa Loa (eye worm)	hypothetical protein	0.00533414	0.0263164	0.0390857
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.00533414	0.0263164	0.0390857
Schistosoma mansoni	hypothetical protein	0.00533414	0.0263164	0.0390857
Echinococcus multilocularis	glycoprotein Antigen 5	0.00533414	0.0263164	0.37661
Echinococcus granulosus	Peptidase S1 S6 chymotrypsin Hap	0.00533414	0.0263164	0.37661
Schistosoma mansoni	hypothetical protein	0.00533414	0.0263164	0.0390857
Brugia malayi	Variant SH3 domain containing protein	0.0111874	0.189582	0.281572
Onchocerca volvulus		0.0285291	0.6733	0.6733
Echinococcus granulosus	Mastin	0.00533414	0.0263164	0.37661
Trypanosoma cruzi	hypothetical protein, conserved	0.00689584	0.0698771	0.5
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.00533414	0.0263164	0.0390857
Echinococcus granulosus	glycoprotein Antigen 5	0.00533414	0.0263164	0.37661
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Onchocerca volvulus		0.0402416	1	1
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Toxoplasma gondii	PAN domain-containing protein	0.0309062	0.739606	1
Echinococcus granulosus	tissue type plasminogen activator	0.00689584	0.0698771	1
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Echinococcus multilocularis	enteropeptidase	0.00533414	0.0263164	0.37661
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Schistosoma mansoni	cercarial elastase (S01 family)	0.00533414	0.0263164	0.0390857
Echinococcus granulosus	enteropeptidase	0.00533414	0.0263164	0.37661
Brugia malayi	Trypsin family protein	0.00533414	0.0263164	0.0390857
Echinococcus granulosus	subfamily S1A unassigned peptidase S01 family	0.00533414	0.0263164	0.37661
Echinococcus multilocularis	Peptidase S1 S6, chymotrypsin Hap	0.00533414	0.0263164	0.37661
Loa Loa (eye worm)	hypothetical protein	0.00533414	0.0263164	0.0390857
Toxoplasma gondii	kringle domain-containing protein	0.00689584	0.0698771	0.0944788
Brugia malayi	Protein kinase domain containing protein	0.00689584	0.0698771	0.103783
Loa Loa (eye worm)	hypothetical protein	0.0285291	0.6733	1
Brugia malayi	Trypsin family protein	0.00533414	0.0263164	0.0390857
Onchocerca volvulus		0.00533414	0.0263164	0.0263164
Onchocerca volvulus		0.00689584	0.0698771	0.0698771
Loa Loa (eye worm)	hypothetical protein	0.00533414	0.0263164	0.0390857
Echinococcus multilocularis	tissue type plasminogen activator	0.00689584	0.0698771	1
Mycobacterium ulcerans	hypothetical protein	0.00533414	0.0263164	0.5
Onchocerca volvulus		0.00533414	0.0263164	0.0263164

Activities

Activity type	Activity value	Assay description	Source	Reference
AP (functional)	= 16.1	Average potency of all four cell lines (P388 cell line, L1210 cell line, Molt 4/C8 cell line, CEM T-lymphocytes)	ChEMBL.	11170648
CC50 (functional)	= 18 uM	Cytotoxicity against human HSC2 by MTT method	ChEMBL.	17499885
CC50 (functional)	= 20 uM	Cytotoxicity against human HSC4 cells by MTT method	ChEMBL.	17499885
CC50 (functional)	= 22 uM	Cytotoxicity against human HL60 cells in presence of RPMI1640 containing 10% fetal bovine serum by trypan blue exclusion test	ChEMBL.	17499885
GI50 (functional)	-5.939	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SF-539 Central Nervous System cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-5.724	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the NCI-H23 Non-Small Cell Lung cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-5.586	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SN12C Renal cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-5.577	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the DU-145 Prostate cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-5.567	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the MDA-N Breast cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-5.484	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the ACHN Renal cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-5.458	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the UO-31 Renal cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-5.353	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SK-MEL-5 Melanoma cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-5.216	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the MALME-3M Melanoma cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-5.026	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the HL-60(TB) Leukemia cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-4.804	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the HOP-92 Non-Small Cell Lung cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
IC50 (functional)	= 128 ng/ml	Antimalarial activity against drug-resistant Plasmodium falciparum C235 after 72 hrs by SYBR green I staining-based fluorescence assay	ChEMBL.	24139941
IC50 (functional)	= 597 ng/ml	Antimalarial activity against liver stage Plasmodium berghei ANKA sporozoites infected in human HepG2 cells after 48 hrs by luciferase reporter gene assay	ChEMBL.	24139941
IC50 (ADMET)	> 2000 ng/ml	Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay	ChEMBL.	24139941
IC50 (functional)	= 0.74 uM	Cytotoxicity against murine P388 cells.	ChEMBL.	11170648
IC50 (functional)	= 0.74 uM	Cytotoxicity against murine P388 cells.	ChEMBL.	11170648
IC50 (functional)	= 7 uM	Cytotoxicity against Mus musculus (mouse) L1210 cells assessed as growth inhibition after 72 hr by MTT assay	ChEMBL.	No reference
IC50 (functional)	= 8.63 uM	Cytotoxicity against CEM T-lymphocytes.	ChEMBL.	11170648
IC50 (functional)	= 8.63 uM	Cytotoxicity against CEM T-lymphocytes.	ChEMBL.	11170648
IC50 (functional)	= 13.4 uM	Cytotoxicity against human Molt 4/C8 cells.	ChEMBL.	11170648
IC50 (functional)	= 41.5 uM	Cytotoxicity against murine L1210 cells.	ChEMBL.	11170648
IC50 (functional)	= 41.5 uM	Cytotoxicity against murine L1210 cells.	ChEMBL.	11170648
LogP	= 4.71	Lipophilicity, log P of the compound	ChEMBL.	18513966
Ratio (binding)	= 0.91	Reversal of P-glycoprotein-mediated multidrug resistance in human MDR1 gene transfected mouse L5178Y cells assessed as fluorescence activity ratio at 40 ug/ml by flow cytometry	ChEMBL.	18513966
Ratio (binding)	= 1.25	Reversal of P-glycoprotein-mediated multidrug resistance in human MDR1 gene transfected mouse L5178Y cells assessed as fluorescence activity ratio at 4 ug/ml by flow cytometry	ChEMBL.	18513966
Ratio (binding)	= 0.91	Reversal of P-glycoprotein-mediated multidrug resistance in human MDR1 gene transfected mouse L5178Y cells assessed as fluorescence activity ratio at 40 ug/ml by flow cytometry	ChEMBL.	18513966
Ratio (binding)	= 1.25	Reversal of P-glycoprotein-mediated multidrug resistance in human MDR1 gene transfected mouse L5178Y cells assessed as fluorescence activity ratio at 4 ug/ml by flow cytometry	ChEMBL.	18513966
Ratio IC50 (functional)	= 1.24	Ratio of IC50 for drug-resistant Plasmodium falciparum C235 to IC50 for drug-sensitive Plasmodium falciparum D6	ChEMBL.	24139941
T1/2 (ADMET)	> 60 min	Half life in mouse plasma at 1 mM by LC/MS analysis	ChEMBL.	24139941
T1/2 (ADMET)	> 60 min	Half life in human plasma at 1 mM by LC/MS analysis	ChEMBL.	24139941

Phenotypes

Whole-cell/tissue/organism interactions

Species name	Source	Reference
Mus musculus	ChEMBL23	11170648
Homo sapiens	ChEMBL23	11170648
Plasmodium falciparum	ChEMBL23	24139941
Plasmodium berghei	ChEMBL23	24139941

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: CHEMBL347880
PubChem: 5469265

Bibliographic References

2 literature references were 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 265364