Detailed information for compound 409560

Basic information

Technical information
  • TDR Targets ID: 409560
  • Name: 2-hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-meth ylfuran-2-yl)ethyl]amino]-3,4-dioxocyclobuten -1-yl]amino]benzamide
  • MW: 383.398 | Formula: C20H21N3O5
  • H donors: 3 H acceptors: 4 LogP: 2.57 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: Cc1ccc(o1)[C@H](NC1=C(C(=O)C1=O)Nc1cccc(c1O)C(=O)N(C)C)C
  • InChi: 1S/C20H21N3O5/c1-10-8-9-14(28-10)11(2)21-15-16(19(26)18(15)25)22-13-7-5-6-12(17(13)24)20(27)23(3)4/h5-9,11,21-22,24H,1-4H3/t11-/m1/s1
  • InChiKey: ACYREHAZQPOKBX-LLVKDONJSA-N  

Network

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Synonyms

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

Obtained from network model

Ranking Plot


Putative Targets List


Species Potential target Raw Global Species
Brugia malayi Nuclear hormone receptor family member nhr-14 0.0224 0.0973 0.2785
Loa Loa (eye worm) nuclear hormone receptor family member nhr-31 0.0224 0.0973 0.2785
Schistosoma mansoni thyroid hormone receptor 0.0346 0.16 0.4725
Brugia malayi hypothetical protein 0.007 0.0175 0.0338
Echinococcus granulosus nuclear receptor nhr 48 0.0098 0.0323 0.0993
Brugia malayi hypothetical protein 0.0098 0.0323 0.0791
Echinococcus multilocularis nuclear receptor nhr 48 0.0098 0.0323 0.0993
Brugia malayi Nuclear hormone receptor family member nhr-3 0.0224 0.0973 0.2785
Brugia malayi hypothetical protein 0.0126 0.0467 0.1232
Brugia malayi Nuclear hormone receptor-like 1 0.0126 0.0467 0.1232
Brugia malayi Nuclear hormone receptor-like 1 0.0224 0.0973 0.2785
Schistosoma mansoni nuclear hormone receptor nor-1/nor-2 0.0224 0.0973 0.2724
Loa Loa (eye worm) gamma-secretase subunit pen-2 0.0186 0.0777 0.2184
Brugia malayi Nuclear hormone receptor family member nhr-19 0.0224 0.0973 0.2785
Brugia malayi Nuclear hormone receptor-like 1 0.0126 0.0467 0.1232
Brugia malayi photoreceptor-specific nuclear receptor 0.0224 0.0973 0.2785
Echinococcus multilocularis Nuclear hormone receptor family member nhr 41 0.0224 0.0973 0.2991
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Echinococcus granulosus aldehyde dehydrogenase mitochondrial 0.0059 0.0119 0.0366
Schistosoma mansoni nuclear hormone receptor 0.0098 0.0323 0.0651
Schistosoma mansoni gamma-secretase subunit aph-1 0.0473 0.2256 0.6819
Brugia malayi hypothetical protein 0.007 0.0175 0.0338
Brugia malayi Nuclear hormone receptor family member nhr-41 0.0224 0.0973 0.2785
Echinococcus multilocularis thyroid hormone receptor alpha 0.0346 0.16 0.4918
Echinococcus multilocularis microtubule associated protein 2 0.0667 0.3253 1
Brugia malayi hypothetical protein 0.0097 0.0315 0.0768
Echinococcus multilocularis nuclear receptor subfamily 1 group D 0.0126 0.0467 0.1434
Loa Loa (eye worm) nuclear hormone receptor 0.0098 0.0323 0.0791
Loa Loa (eye worm) gamma-secretase subunit aph-1 0.0473 0.2256 0.6721
Trichomonas vaginalis Clan AD, family A22, presenilin-like aspartic peptidase 0.0198 0.084 1
Loa Loa (eye worm) nuclear Hormone Receptor family member 0.0224 0.0973 0.2785
Echinococcus multilocularis Mitotic checkpoint protein PRCC, C terminal 0.0122 0.0444 0.1364
Echinococcus multilocularis FTZ F1 alpha 0.0224 0.0973 0.2991
Echinococcus granulosus nuclear receptor subfamily 1 group D 0.0126 0.0467 0.1434
Brugia malayi tailless protein 0.0098 0.0323 0.0791
Loa Loa (eye worm) presenilin spe-4 0.007 0.0175 0.0338
Schistosoma mansoni coup transcription factor 0.0224 0.0973 0.2724
Loa Loa (eye worm) nuclear hormone receptor family member nhr-1 0.0224 0.0973 0.2785
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Loa Loa (eye worm) hypothetical protein 0.0224 0.0973 0.2785
Echinococcus granulosus hepatocyte nuclear factor 4 alpha 0.0224 0.0973 0.2991
Brugia malayi nuclear receptor RXR 0.0098 0.0323 0.0791
Brugia malayi gamma-secretase subunit pen-2 0.0186 0.0777 0.2184
Echinococcus multilocularis Nicastrin 0.0097 0.0315 0.097
Loa Loa (eye worm) hypothetical protein 0.0126 0.0467 0.1232
Echinococcus granulosus presenilin enhancer 2 0.0186 0.0777 0.2389
Brugia malayi hypothetical protein 0.0097 0.0315 0.0768
Mycobacterium ulcerans short chain dehydrogenase 0.1975 1 1
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0098 0.0323 0.0993
Loa Loa (eye worm) nuclear receptor nhr-7B 0.0098 0.0323 0.0791
Echinococcus multilocularis retinoic acid receptor rxr beta a retinoic acid receptor rxr alpha a retinoic acid receptor rxr alpha 0.0193 0.0814 0.2502
Brugia malayi hypothetical protein 0.0126 0.0467 0.1232
Onchocerca volvulus Bile acid receptor homolog 0.0681 0.3326 1
Loa Loa (eye worm) hypothetical protein 0.0224 0.0973 0.2785
Echinococcus granulosus thyroid hormone receptor alpha 0.0386 0.1806 0.555
Loa Loa (eye worm) steroid hormone receptor 0.0512 0.2455 0.7331
Schistosoma mansoni photoreceptor-specific nuclear receptor related 0.0224 0.0973 0.2724
Schistosoma mansoni subfamily A22A unassigned peptidase (A22 family) 0.0198 0.084 0.23
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0098 0.0323 0.0993
Onchocerca volvulus Protein ultraspiracle homolog 0.0224 0.0973 0.2165
Brugia malayi Presenilin family protein 0.0198 0.084 0.2377
Loa Loa (eye worm) DR-78 0.0098 0.0323 0.0791
Echinococcus multilocularis aldehyde dehydrogenase, mitochondrial 0.0059 0.0119 0.0366
Loa Loa (eye worm) nuclear hormone receptor family member nhr-49 0.0224 0.0973 0.2785
Schistosoma mansoni zinc finger protein 0.0098 0.0323 0.0651
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Schistosoma mansoni retinoic acid receptor RXR 0.032 0.1464 0.4291
Loa Loa (eye worm) hypothetical protein 0.0126 0.0467 0.1232
Loa Loa (eye worm) nuclear receptor NHR-67 0.0098 0.0323 0.0791
Loa Loa (eye worm) hypothetical protein 0.0224 0.0973 0.2785
Brugia malayi conserved hypotetical protein 0.0098 0.0323 0.0791
Brugia malayi gamma-secretase subunit aph-1 0.0473 0.2256 0.6721
Loa Loa (eye worm) hypothetical protein 0.0126 0.0467 0.1232
Echinococcus multilocularis ecdysone induced protein 78C 0.0224 0.0973 0.2991
Brugia malayi orphan nuclear receptor NR2E1 0.0098 0.0323 0.0791
Brugia malayi hypothetical protein 0.007 0.0175 0.0338
Schistosoma mansoni FTZ-F1 nuclear receptor-like protein 0.0224 0.0973 0.2724
Echinococcus granulosus Nuclear hormone receptor family member nhr 41 0.0224 0.0973 0.2991
Brugia malayi ecdysteroid receptor 0.0681 0.3326 1
Loa Loa (eye worm) hypothetical protein 0.0224 0.0973 0.2785
Loa Loa (eye worm) hypothetical protein 0.0126 0.0467 0.1232
Echinococcus multilocularis presenilin 0.0198 0.084 0.2582
Echinococcus granulosus FTZ F1 alpha 0.0224 0.0973 0.2991
Loa Loa (eye worm) hypothetical protein 0.0097 0.0315 0.0768
Brugia malayi nuclear receptor subfamily 1, group D, member 1, putative 0.0098 0.0323 0.0791
Entamoeba histolytica presenilin 1 peptidase, putative 0.0198 0.084 1
Brugia malayi N-terminal motif family protein 0.0174 0.0716 0.1996
Schistosoma mansoni hepatocyte nuclear factor 4-alpha (hnf-4-alpha) 0.0098 0.0323 0.0651
Schistosoma mansoni nuclear receptor 2DBD-gamma 0.0224 0.0973 0.2724
Brugia malayi Nuclear hormone receptor E75 0.0098 0.0323 0.0791
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Echinococcus multilocularis presenilin enhancer 2 0.0186 0.0777 0.2389
Echinococcus granulosus Nicastrin 0.0097 0.0315 0.097
Loa Loa (eye worm) hypothetical protein 0.0681 0.3326 1
Brugia malayi Nuclear hormone receptor family member nhr-25 0.0224 0.0973 0.2785
Brugia malayi Nuclear hormone receptor family member nhr-25 0.0224 0.0973 0.2785
Schistosoma mansoni nuclear hormone receptor superfamily protein-related 0.0098 0.0323 0.0651
Brugia malayi Presenilin spe-4 0.007 0.0175 0.0338
Brugia malayi steroid hormone receptor 0.0512 0.2455 0.7331
Brugia malayi Presenilin-like protein At2g29900 0.007 0.0175 0.0338
Brugia malayi hypothetical protein 0.0098 0.0323 0.0791
Schistosoma mansoni nuclear receptor 0.0098 0.0323 0.0651
Leishmania major aldehyde dehydrogenase, mitochondrial precursor 0.0059 0.0119 0.0183
Schistosoma mansoni Tr4/Tr2 (homologue) 0.0224 0.0973 0.2724
Brugia malayi nuclear hormone receptor 0.0224 0.0973 0.2785
Brugia malayi Presenilin spe-4 0.007 0.0175 0.0338
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.0224 0.0973 0.2785
Schistosoma mansoni RAR-like nuclear receptor 0.0224 0.0973 0.2724
Echinococcus granulosus nuclear receptor subfamily 4 group A 0.0098 0.0323 0.0993
Echinococcus granulosus FTZ F1 nuclear receptor protein 0.0224 0.0973 0.2991
Echinococcus multilocularis Nuclear hormone receptor HR96 0.0098 0.0323 0.0993
Trypanosoma brucei Aph-1 protein, putative 0.0184 0.0767 0.9136
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Brugia malayi nuclear receptor NHR-67 0.0098 0.0323 0.0791
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0224 0.0973 0.2991
Echinococcus granulosus Nuclear hormone receptor HR96 0.0098 0.0323 0.0993
Echinococcus multilocularis gamma secretase subunit aph 1 0.0473 0.2256 0.6935
Trypanosoma brucei Presenilin enhancer-2 subunit of gamma secretase, putative 0.0056 0.0106 0.1259
Brugia malayi nuclear hormone receptor family member nhr-6 0.0098 0.0323 0.0791
Brugia malayi Nuclear hormone receptor family member nhr-49 0.0224 0.0973 0.2785
Loa Loa (eye worm) nuclear hormone receptor family member nhr-14 0.0224 0.0973 0.2785
Onchocerca volvulus Steroid hormone receptor family member cnr14 homolog 0.0224 0.0973 0.2165
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Brugia malayi Nuclear hormone receptor family member nhr-31 0.0224 0.0973 0.2785
Echinococcus multilocularis COUP TF:Svp nuclear hormone receptor 0.0224 0.0973 0.2991
Echinococcus multilocularis hepatocyte nuclear factor 4 alpha 0.0224 0.0973 0.2991
Brugia malayi nuclear receptor NHR-88 0.0098 0.0323 0.0791
Echinococcus granulosus presenilin 0.0198 0.084 0.2582
Onchocerca volvulus 0.0224 0.0973 0.2165
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Trypanosoma cruzi presenilin-like aspartic peptidase, putative 0.0198 0.084 1
Brugia malayi nuclear hormone receptor family member odr-7 0.0098 0.0323 0.0791
Schistosoma mansoni nuclear hormone receptor 0.0224 0.0973 0.2724
Loa Loa (eye worm) hypothetical protein 0.0174 0.0716 0.1996
Schistosoma mansoni nuclear receptor nhr-48 0.0098 0.0323 0.0651
Brugia malayi Nuclear hormone receptor family member nhr-40 0.0224 0.0973 0.2785
Brugia malayi Nuclear hormone receptor family member nhr-1 0.0224 0.0973 0.2785
Trypanosoma cruzi Aph-1 protein, putative 0.0184 0.0767 0.9136
Echinococcus granulosus ecdysone induced protein 78C 0.0224 0.0973 0.2991
Brugia malayi Presenilin spe-4 0.007 0.0175 0.0338
Schistosoma mansoni hypothetical protein 0.0097 0.0315 0.0626
Loa Loa (eye worm) hypothetical protein 0.0224 0.0973 0.2785
Trypanosoma cruzi Aph-1 protein, putative 0.0184 0.0767 0.9136
Brugia malayi Nuclear hormone receptor family member nhr-19 0.0224 0.0973 0.2785
Schistosoma mansoni ecdysone-induced protein 78c (dr-78) 0.0126 0.0467 0.1109
Loa Loa (eye worm) hypothetical protein 0.0224 0.0973 0.2785
Brugia malayi nuclear hormone receptor 0.0098 0.0323 0.0791
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Echinococcus granulosus gamma secretase subunit aph 1 0.0473 0.2256 0.6935
Schistosoma mansoni microtubule-associated protein tau 0.0667 0.3253 1
Schistosoma mansoni nuclear hormone receptor 0.0098 0.0323 0.0651
Schistosoma mansoni nuclear receptor 0.0098 0.0323 0.0651
Trichomonas vaginalis Clan AD, family A22, presenilin-like aspartic peptidase 0.0198 0.084 1
Echinococcus multilocularis Nuclear hormone receptor HR96 0.0098 0.0323 0.0993
Leishmania major presenilin-like aspartic peptidase, putative,presenilin-like aspartic peptidase, clan AD, family A22A, putative 0.0198 0.084 1
Schistosoma mansoni retinoid-x-receptor (RXR) 0.0126 0.0467 0.1109
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.0224 0.0973 0.2991
Echinococcus multilocularis nuclear receptor subfamily 4 group A 0.0098 0.0323 0.0993
Loa Loa (eye worm) hypothetical protein 0.0126 0.0467 0.1232
Toxoplasma gondii hypothetical protein 0.007 0.0175 1
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0224 0.0973 0.2991
Schistosoma mansoni hypothetical protein 0.0122 0.0444 0.1036
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Echinococcus multilocularis FTZ F1 nuclear receptor protein 0.0224 0.0973 0.2991
Trypanosoma brucei presenilin-like aspartic peptidase, putative 0.0198 0.084 1
Onchocerca volvulus Rap guanine nucleotide exchange factor 1 homolog 0.0174 0.0716 0.1308
Echinococcus granulosus retinoic acid receptor rxr beta a 0.032 0.1464 0.45
Brugia malayi ecdysone receptor 0.0098 0.0323 0.0791
Trichomonas vaginalis Clan AD, family A22, presenilin-like aspartic peptidase 0.0198 0.084 1
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Loa Loa (eye worm) nuclear hormone receptor family member nhr-41 0.0224 0.0973 0.2785
Echinococcus multilocularis Nicastrin 0.0097 0.0315 0.097
Brugia malayi Steroid receptor seven-up type 2 0.0224 0.0973 0.2785
Toxoplasma gondii aldehyde dehydrogenase 0.0059 0.0119 0.1936
Schistosoma mansoni thyroid hormone receptor 0.0346 0.16 0.4725
Brugia malayi nuclear receptor RXR 0.0126 0.0467 0.1232
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Echinococcus granulosus COUP TF:Svp nuclear hormone receptor 0.0224 0.0973 0.2991
Brugia malayi Nuclear hormone receptor E75 0.0098 0.0323 0.0791
Echinococcus granulosus nuclear receptor 2DBD gamma 0.0224 0.0973 0.2991
Echinococcus granulosus Mitotic checkpoint protein PRCC C terminal 0.0122 0.0444 0.1364
Echinococcus granulosus Nuclear hormone receptor HR96 0.0098 0.0323 0.0993
Brugia malayi nuclear receptor NHR-88 0.0224 0.0973 0.2785
Schistosoma mansoni steroid hormone receptor ad4bp 0.0224 0.0973 0.2724
Loa Loa (eye worm) nuclear hormone receptor family member nhr-40 0.0224 0.0973 0.2785
Echinococcus granulosus microtubule associated protein 2 0.0667 0.3253 1
Trypanosoma cruzi presenilin-like aspartic peptidase, putative 0.0198 0.084 1
Loa Loa (eye worm) hypothetical protein 0.0098 0.0323 0.0791
Loa Loa (eye worm) hypothetical protein 0.0224 0.0973 0.2785
Schistosoma mansoni retinoid-x-receptor (RXR) 0.0224 0.0973 0.2724
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.0224 0.0973 0.2785
Loa Loa (eye worm) nuclear hormone receptor-like 1 0.0126 0.0467 0.1232

Activities

Activity type Activity value Assay description Source Reference
AUC (ADMET) = 34 uM.hr AUC (0-6h) in rat at 10 mg/kg, po ChEMBL. 17181143
IC50 (functional) = 2.4 nM Inhibition of CXCL1-induced human neutrophil chemotaxis ChEMBL. 17181143
IC50 (functional) = 2.4 nM Inhibition of CXCL1-induced human neutrophil chemotaxis ChEMBL. 17181143
IC50 (binding) = 5.4 nM Displacement of [125I]hCXCL8 from human CXCR2 receptor expressed in BaF3 cells ChEMBL. 17181143
IC50 (binding) = 5.4 nM Displacement of [125I]hCXCL8 from human CXCR2 receptor expressed in BaF3 cells ChEMBL. 17181143
IC50 (functional) = 251 nM Inhibition of CXCL8-induced human neutrophil chemotaxis ChEMBL. 17181143
IC50 (functional) = 251 nM Inhibition of CXCL8-induced human neutrophil chemotaxis ChEMBL. 17181143
IC50 (binding) = 775 nM Displacement of [125I]hCXCL8 from human CXCR1 receptor expressed in BaF3 cells ChEMBL. 17181143
IC50 (binding) = 775 nM Displacement of [125I]hCXCL8 from human CXCR1 receptor expressed in BaF3 cells ChEMBL. 17181143
Ratio IC50 (binding) > 100 Selectivity for CXCR2 over CXCR1 ChEMBL. 17181143
Ratio IC50 (binding) > 100 Selectivity for CXCR2 over CXCR1 ChEMBL. 17181143

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

Bibliographic References

1 literature reference was collected for this gene.

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