Detailed information for compound 409057

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  


Substructure search Similarity search

Network

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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 1 Starlite/ChEMBL References
Homo sapiens chemokine (C-X-C motif) receptor 2 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
Obtained from network model

Ranking Plot

Putative Targets List

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

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.
 
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External resources for this compound

Bibliographic References

7 literature references were collected for this gene.

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