TDR Targets

Basic information

Technical information

TDR Targets ID: 409057
Name: 2-hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-meth ylfuran-2-yl)propyl]amino]-3,4-dioxocyclobute n-1-yl]amino]benzamide
MW: 397.424 | Formula: C21H23N3O5
H donors: 3 H acceptors: 4 LogP: 3.1 Rotable bonds: 8
Rule of 5 violations (Lipinski): 1
SMILES: CC[C@H](c1ccc(o1)C)NC1=C(C(=O)C1=O)Nc1cccc(c1O)C(=O)N(C)C
InChi: 1S/C21H23N3O5/c1-5-13(15-10-9-11(2)29-15)22-16-17(20(27)19(16)26)23-14-8-6-7-12(18(14)25)21(28)24(3)4/h6-10,13,22-23,25H,5H2,1-4H3/t13-/m1/s1
InChiKey: RXIUEIPPLAFSDF-CYBMUJFWSA-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

2-hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methyl-2-furyl)propyl]amino]-3,4-dioxo-cyclobuten-1-yl]amino]benzamide
2-hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methyl-2-furyl)propyl]amino]-3,4-dioxo-1-cyclobutenyl]amino]benzamide
2-hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methylfuran-2-yl)propyl]amino]-3,4-dioxo-cyclobuten-1-yl]amino]benzamide
3-[[3,4-diketo-2-[[(1R)-1-(5-methyl-2-furyl)propyl]amino]cyclobuten-1-yl]amino]-2-hydroxy-N,N-dimethyl-benzamide
2-hydroxy-N,N-dimethyl-3-(2-((1-(5-methylfuran-2-yl)propyl)amino)-3,4-dioxocyclobut-1-enylamino)benzamide
2-hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methylfuran-2-yl)propyl]amino]-3,4-dioxo-1-cyclobutenyl]amino]benzamide
3-[[3,4-diketo-2-[[(1R)-1-(5-methyl-2-furyl)propyl]amino]-1-cyclobutenyl]amino]-2-hydroxy-N,N-dimethyl-benzamide

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	chemokine (C-X-C motif) receptor 2	Starlite/ChEMBL	References
Homo sapiens	chemokine (C-X-C motif) receptor 1	Starlite/ChEMBL	References

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 granulosus	slit 2 protein	0.0272	0.0372	0.035
Loa Loa (eye worm)	TK/ROR protein kinase	0.0479	0.1529	0.1202
Brugia malayi	Fibulin-1 precursor	0.0637	0.2406	0.2113
Echinococcus granulosus	subfamily S1A unassigned peptidase S01 family	0.035	0.0806	0.132
Loa Loa (eye worm)	hypothetical protein	0.035	0.0806	0.0451
Echinococcus multilocularis	neurogenic locus notch protein 4	0.0272	0.0372	0.0792
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.035	0.0806	0.0604
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.035	0.0806	0.0604
Schistosoma mansoni	hypothetical protein	0.0272	0.0372	0.016
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.035	0.0806	0.0604
Schistosoma mansoni	hypothetical protein	0.035	0.0806	0.0604
Echinococcus granulosus	enteropeptidase	0.035	0.0806	0.132
Echinococcus multilocularis	fat cadherin tumor suppressor	0.0272	0.0372	0.0792
Loa Loa (eye worm)	hypothetical protein	0.0637	0.2406	0.2113
Echinococcus multilocularis	fibropellin Ia	0.0272	0.0372	0.0792
Echinococcus multilocularis	glycoprotein Antigen 5	0.035	0.0806	0.1718
Trypanosoma cruzi	hypothetical protein, conserved	0.1092	0.4945	1
Loa Loa (eye worm)	hypothetical protein	0.0637	0.2406	0.2113
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Plasmodium vivax	cysteine repeat modular protein 1, putative	0.0479	0.1529	0.5
Schistosoma mansoni	notch	0.0272	0.0372	0.016
Schistosoma mansoni	notch	0.0272	0.0372	0.016
Echinococcus granulosus	neural cadherin	0.0272	0.0372	0.035
Schistosoma mansoni	aminopeptidase PILS (M01 family)	0.035	0.0806	0.0604
Echinococcus multilocularis	enteropeptidase	0.035	0.0806	0.1718
Schistosoma mansoni	hypothetical protein	0.0272	0.0372	0.016
Echinococcus granulosus	neurogenic locus notch protein	0.0272	0.0372	0.035
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Echinococcus granulosus	protein jagged 2	0.0272	0.0372	0.035
Onchocerca volvulus		0.035	0.0806	0.0451
Echinococcus multilocularis	notch	0.0272	0.0372	0.0792
Schistosoma mansoni	notch	0.0272	0.0372	0.016
Echinococcus multilocularis	subfamily S1A unassigned peptidase (S01 family)	0.035	0.0806	0.1718
Schistosoma mansoni	hypothetical protein	0.035	0.0806	0.0604
Echinococcus granulosus	protein jagged 1	0.0272	0.0372	0.035
Loa Loa (eye worm)	low-density lipoprotein receptor repeat class B containing protein	0.0637	0.2406	0.2113
Schistosoma mansoni	notch	0.0272	0.0372	0.016
Echinococcus granulosus	neurogenic locus notch protein	0.0272	0.0372	0.035
Echinococcus multilocularis	neural cadherin	0.0272	0.0372	0.0792
Echinococcus multilocularis	tissue type plasminogen activator	0.0479	0.1529	0.3257
Onchocerca volvulus		0.035	0.0806	0.0451
Schistosoma mansoni	hypothetical protein	0.0479	0.1529	0.1343
Onchocerca volvulus	Arrow homolog	0.0637	0.2406	0.2113
Echinococcus granulosus	laminin	0.0637	0.2406	0.4891
Schistosoma mansoni	Pro-neuregulin-4 membrane-bound isoform (Pro-NRG4) [Contains: Neuregulin-4 (NRG-4)]	0.0272	0.0372	0.016
Echinococcus multilocularis	neurogenic locus notch protein	0.0272	0.0372	0.0792
Loa Loa (eye worm)	hypothetical protein	0.035	0.0806	0.0451
Loa Loa (eye worm)	hypothetical protein	0.0637	0.2406	0.2113
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.1999	1	1
Loa Loa (eye worm)	hypothetical protein	0.1999	1	1
Brugia malayi	Trypsin family protein	0.035	0.0806	0.0451
Loa Loa (eye worm)	trypsin family protein	0.035	0.0806	0.0451
Brugia malayi	Protein kinase domain containing protein	0.0479	0.1529	0.1202
Echinococcus granulosus	fibropellin Ia	0.0272	0.0372	0.035
Toxoplasma gondii	kringle domain-containing protein	0.0479	0.1529	0.4507
Echinococcus multilocularis	tm gpcr rhodopsin gpcr rhodopsin superfamily	0.1047	0.4695	1
Schistosoma mansoni	hypothetical protein	0.0272	0.0372	0.016
Onchocerca volvulus		0.035	0.0806	0.0451
Onchocerca volvulus		0.1999	1	1
Schistosoma mansoni	notch	0.0272	0.0372	0.016
Echinococcus multilocularis	Peptidase S1 S6, chymotrypsin Hap	0.035	0.0806	0.1718
Echinococcus multilocularis	protein jagged 2	0.0272	0.0372	0.0792
Schistosoma mansoni	hypothetical protein	0.0272	0.0372	0.016
Entamoeba histolytica	hypothetical protein	0.1092	0.4945	0.5
Echinococcus granulosus	protein jagged 2	0.0272	0.0372	0.035
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Toxoplasma gondii	PAN domain-containing protein	0.0732	0.294	1
Echinococcus granulosus	neurogenic locus notch protein 4	0.0272	0.0372	0.035
Toxoplasma gondii	calcium binding egf domain-containing protein	0.0637	0.2406	0.7922
Echinococcus granulosus	protein jagged 1	0.0272	0.0372	0.035
Brugia malayi	Trypsin family protein	0.035	0.0806	0.0451
Schistosoma mansoni	hypothetical protein	0.0272	0.0372	0.016
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.035	0.0806	0.0604
Echinococcus granulosus	Peptidase S1 S6 chymotrypsin Hap	0.035	0.0806	0.132
Echinococcus multilocularis	fibrillin 1	0.0637	0.2406	0.5125
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Loa Loa (eye worm)	hypothetical protein	0.035	0.0806	0.0451
Schistosoma mansoni	slit	0.0272	0.0372	0.016
Schistosoma mansoni	notch	0.0272	0.0372	0.016
Onchocerca volvulus		0.035	0.0806	0.0451
Loa Loa (eye worm)	hypothetical protein	0.035	0.0806	0.0451
Schistosoma mansoni	cell polarity protein	0.0272	0.0372	0.016
Brugia malayi	Chymotrypsin-like protease CTRL-1 precursor	0.035	0.0806	0.0451
Echinococcus granulosus	tm gpcr rhodopsin	0.1047	0.4695	1
Onchocerca volvulus		0.035	0.0806	0.0451
Echinococcus granulosus	glycoprotein Antigen 5	0.035	0.0806	0.132
Schistosoma mansoni	egf-like domain protein	0.0637	0.2406	0.2239
Onchocerca volvulus		0.1649	0.805	0.7975
Loa Loa (eye worm)	hypothetical protein	0.0479	0.1529	0.1202
Echinococcus granulosus	transmembrane protease serine 3	0.035	0.0806	0.132
Trypanosoma cruzi	hypothetical protein, conserved	0.1092	0.4945	1
Echinococcus multilocularis	Tolloid protein 1	0.0637	0.2406	0.5125
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.035	0.0806	0.0604
Loa Loa (eye worm)	hypothetical protein	0.0637	0.2406	0.2113
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Echinococcus multilocularis	slit 2 protein	0.0272	0.0372	0.0792
Echinococcus multilocularis	transmembrane protease serine 3	0.035	0.0806	0.1718
Loa Loa (eye worm)	hypothetical protein	0.0643	0.2442	0.2151
Loa Loa (eye worm)	hypothetical protein	0.0675	0.2621	0.2336
Echinococcus multilocularis	protein jagged 1	0.0272	0.0372	0.0792
Loa Loa (eye worm)	multiple epidermal growth factor-like domains 6	0.0637	0.2406	0.2113
Echinococcus multilocularis	Coagulation factor 5 8 type, C terminal	0.0244	0.0215	0.0458
Echinococcus multilocularis	neurogenic locus protein delta	0.0272	0.0372	0.0792
Loa Loa (eye worm)	hypothetical protein	0.1213	0.5617	0.5448
Schistosoma mansoni	septate junction protein	0.031	0.0587	0.038
Leishmania major	hypothetical protein, conserved	0.0479	0.1529	0.5
Brugia malayi	Kringle domain containing protein	0.0479	0.1529	0.1202
Loa Loa (eye worm)	hypothetical protein	0.035	0.0806	0.0451
Echinococcus granulosus	tissue type plasminogen activator	0.0479	0.1529	0.2934
Echinococcus multilocularis	protein jagged 1	0.0272	0.0372	0.0792
Echinococcus granulosus	Tolloid protein 1	0.0637	0.2406	0.4891
Echinococcus granulosus	Mastin	0.035	0.0806	0.132
Echinococcus multilocularis	laminin	0.0637	0.2406	0.5125
Echinococcus multilocularis	neurogenic locus notch protein	0.0272	0.0372	0.0792
Loa Loa (eye worm)	hypothetical protein	0.0704	0.278	0.2501
Toxoplasma gondii	PAN domain-containing protein	0.0732	0.294	1
Onchocerca volvulus		0.0479	0.1529	0.1202
Schistosoma mansoni	laminin gamma-3 chain	0.0272	0.0372	0.016
Echinococcus granulosus	delta-like protein 1	0.0272	0.0372	0.035
Echinococcus multilocularis	neurogenic locus protein delta	0.0272	0.0372	0.0792
Schistosoma mansoni	subfamily M12A unassigned peptidase (M12 family)	0.0637	0.2406	0.2239
Brugia malayi	Trypsin-like protease protein 5	0.035	0.0806	0.0451
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Echinococcus multilocularis	Mastin	0.035	0.0806	0.1718
Giardia lamblia	High cysteine protein	0.0272	0.0372	0.5
Brugia malayi	gamma-aminobutyric-acid receptor beta subunit precursor	0.0704	0.278	0.2501
Toxoplasma gondii	calcium binding egf domain-containing protein	0.0637	0.2406	0.7922
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Brugia malayi	Calcium binding EGF domain containing protein	0.0637	0.2406	0.2113
Mycobacterium ulcerans	hypothetical protein	0.035	0.0806	0.5
Echinococcus granulosus	notch	0.0272	0.0372	0.035
Schistosoma mansoni	hypothetical protein	0.0272	0.0372	0.016
Brugia malayi	Low-density lipoprotein receptor repeat class B containing protein	0.0637	0.2406	0.2113
Brugia malayi	hypothetical protein	0.035	0.0806	0.0451
Schistosoma mansoni	hypothetical protein	0.0272	0.0372	0.016
Plasmodium falciparum	cysteine repeat modular protein 1	0.0479	0.1529	0.5
Schistosoma mansoni	subfamily S1A unassigned peptidase (S01 family)	0.1999	1	1
Schistosoma mansoni	cercarial elastase (S01 family)	0.035	0.0806	0.0604
Echinococcus granulosus	neurogenic locus protein delta	0.0272	0.0372	0.035
Brugia malayi	Trypsin family protein	0.035	0.0806	0.0451
Loa Loa (eye worm)	hypothetical protein	0.1999	1	1
Loa Loa (eye worm)	bone morphogenetic protein 1b	0.0637	0.2406	0.2113

Activities

Activity type	Activity value	Assay description	Source	Reference
Activity (functional)		Inhibition of fMLP-induced human neutrophil chemotaxis	ChEMBL.	17181143
Activity (functional)		Inhibition of CXCL1-induced human neutrophil chemotaxis at 2 nM	ChEMBL.	17181143
Activity (functional)		Inhibition of C5a-induced human neutrophil chemotaxis	ChEMBL.	17181143
Activity (functional)	0	Inhibition of CXCL1-induced human neutrophil chemotaxis at 2 nM	ChEMBL.	17181143
Activity (functional)	0	Inhibition of C5a-induced human neutrophil chemotaxis	ChEMBL.	17181143
Activity (functional)	0	Inhibition of fMLP-induced human neutrophil chemotaxis	ChEMBL.	17181143
AUC (ADMET)	= 2 uM.hr	AUC (0 to 24 hrs) in monkey at 3 mg/kg, po	ChEMBL.	18304809
AUC (ADMET)	= 22 uM.hr	AUC (0 to 24 hrs) in rat at 10 mg/kg, po	ChEMBL.	18304809
AUC (ADMET)	= 49 uM.hr	AUC (0-6h) in rat at 10 mg/kg, po	ChEMBL.	17181143
F (ADMET)	= 18 %	Oral bioavailability in monkey at 3 mg/kg	ChEMBL.	18304809
F (ADMET)	= 33 %	Oral bioavailability in rat at 10 mg/kg	ChEMBL.	18304809
IC50 (functional)	< 1 nM	Inhibition of CXCL1-induced human neutrophil chemotaxis	ChEMBL.	17181143
IC50 (functional)	< 1 nM	Inhibition of CXCL1-induced human neutrophil chemotaxis	ChEMBL.	17181143
IC50 (binding)	= 2.6 nM	Displacement of [125I]hCXCL8 from human CXCR2 receptor expressed in BaF3 cells	ChEMBL.	17181143
IC50 (binding)	= 2.6 nM	Displacement of [125I]hCXCL8 from human CXCR2 receptor expressed in BaF3 cells	ChEMBL.	17181143
IC50 (binding)	= 3.9 nM	Binding affinity to CXCR1	ChEMBL.	22931505
IC50 (functional)	= 16 nM	Inhibition of CXCL8-induced human neutrophil chemotaxis	ChEMBL.	17181143
IC50 (functional)	= 16 nM	Inhibition of CXCL8-induced human neutrophil chemotaxis	ChEMBL.	17181143
IC50 (binding)	= 36 nM	Displacement of [125I]hCXCL8 from human CXCR1 receptor expressed in BaF3 cells	ChEMBL.	17181143
IC50 (binding)	= 36 nM	Displacement of [125I]hCXCL8 from human CXCR1 receptor expressed in BaF3 cells	ChEMBL.	17181143
IC50 (binding)	= 49 pM	Binding affinity to CXCR2	ChEMBL.	22931505
IC50 (binding)	= 0.45 uM	Antagonist activity at CXCR2 in human whole blood by CD11b assay	ChEMBL.	25455491
Inhibition (binding)	< 15 %	Inhibition of CXCR3 receptor at 2 to 20 uM	ChEMBL.	17181143
Inhibition (binding)	< 15 %	Inhibition of CCR5 receptor at 2 to 20 uM	ChEMBL.	17181143
Inhibition (binding)	< 15 %	Inhibition of CXCR3 receptor at 2 to 20 uM	ChEMBL.	17181143
Inhibition (binding)	< 15 %	Inhibition of CCR5 receptor at 2 to 20 uM	ChEMBL.	17181143
Ki (binding)	= 4 nM	Binding affinity to CXCR2	ChEMBL.	19196511
Ki (binding)	= 5 nM	Displacement of [125I]IL8 from human CXCR2 expressed in CHO cells by SPA	ChEMBL.	17459706
Ki (binding)	= 5 nM	Displacement of [125I]IL8 from human CXCR2 expressed in CHO cells by SPA	ChEMBL.	17459706
Ki (binding)	= 5 nM	Displacement of human [125I]IL-8 from human CXCR2	ChEMBL.	19525110
Ki (binding)	= 18 nM	Displacement of [125I]IL8 from human CXCR1 expressed in CHO cells by SPA	ChEMBL.	17459706
Ki (binding)	= 18 nM	Displacement of [125I]IL8 from human CXCR1 expressed in CHO cells by SPA	ChEMBL.	17459706
Ki (binding)	= 20 nM	Binding affinity to CXCR1	ChEMBL.	19196511
MRT (ADMET)	= 2 hr	Mean residence time in monkey at 3 mg/kg, po	ChEMBL.	18304809
MRT (ADMET)	= 3.4 hr	Mean residence time in rat at 10 mg/kg, po	ChEMBL.	18304809
t1/2 (ADMET)	= 7.8 hr	Half life in rat at 10 mg/kg, po	ChEMBL.	18304809
t1/2 (ADMET)	= 23.3 hr	Half life in monkey at 3 mg/kg, po	ChEMBL.	18304809

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: CHEMBL216981
PubChem: 9865554

Bibliographic References

7 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 409057