Detailed information for compound 278274

Basic information

Technical information
  • TDR Targets ID: 278274
  • Name: N-[(2R)-1-(dimethylamino)propan-2-yl]-4-metho xybenzo[a]phenazine-11-carboxamide
  • MW: 388.462 | Formula: C23H24N4O2
  • H donors: 1 H acceptors: 3 LogP: 3.6 Rotable bonds: 6
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1cccc2c1ccc1c2nc2c(n1)cccc2C(=O)N[C@@H](CN(C)C)C
  • InChi: 1S/C23H24N4O2/c1-14(13-27(2)3)24-23(28)17-8-5-9-18-22(17)26-21-16-7-6-10-20(29-4)15(16)11-12-19(21)25-18/h5-12,14H,13H2,1-4H3,(H,24,28)/t14-/m1/s1
  • InChiKey: ACAXGYADTLFREX-CQSZACIVSA-N  


Substructure search Similarity search

Network

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Synonyms

  • N-[(1R)-2-(dimethylamino)-1-methyl-ethyl]-4-methoxy-benzo[a]phenazine-11-carboxamide
  • N-[(1R)-2-(dimethylamino)-1-methylethyl]-4-methoxy-11-benzo[a]phenazinecarboxamide
  • N-[(2R)-1-(dimethylamino)propan-2-yl]-4-methoxy-benzo[a]phenazine-11-carboxamide
  • N-[(2R)-1-dimethylaminopropan-2-yl]-4-methoxybenzo[j]phenazine-11-carboxamide
  • N-[(1R)-2-dimethylamino-1-methyl-ethyl]-4-methoxy-benzo[j]phenazine-11-carboxamide
  • N-[(1R)-2-dimethylamino-1-methylethyl]-4-methoxy-11-benzo[j]phenazinecarboxamide
  • N-[(2R)-1-dimethylaminopropan-2-yl]-4-methoxy-benzo[j]phenazine-11-carboxamide

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
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Brugia malayi Variant SH3 domain containing protein 0.026 0.1845 0.1845
Echinococcus granulosus tyrosine protein kinase Fyn 0.055 0.7695 0.7695
Echinococcus multilocularis NCK adaptor protein 0.026 0.1845 0.1845
Schistosoma mansoni nck2/grb4 0.026 0.1845 0.1845
Echinococcus multilocularis tyrosine protein kinase Src42A 0.0385 0.4359 0.4359
Schistosoma mansoni proto-oncogene tyrosine-protein kinase abl1 0.026 0.1845 0.1845
Schistosoma mansoni proto-oncogene tyrosine-protein kinase src 0.0297 0.259 0.259
Echinococcus granulosus tyrosine protein kinase Src42A 0.0385 0.4359 0.4359
Schistosoma mansoni growth factor receptor-bound protein 0.026 0.1845 0.1845
Echinococcus granulosus tyrosine protein kinase Src64B 0.055 0.7695 0.7695
Loa Loa (eye worm) variant SH3 domain-containing protein 0.026 0.1845 0.1845
Loa Loa (eye worm) SRC-1 0.055 0.7695 0.7695
Echinococcus multilocularis tyrosine protein kinase Blk 0.0422 0.5105 0.5105
Loa Loa (eye worm) TK protein kinase 0.0422 0.5105 0.5105
Schistosoma mansoni growth factor receptor-bound protein 0.026 0.1845 0.1845
Echinococcus granulosus tyrosine protein kinase Fyn 0.055 0.7695 0.7695
Brugia malayi Variant SH3 domain containing protein 0.026 0.1845 0.1845
Echinococcus multilocularis tyrosine protein kinase Fyn 0.0422 0.5105 0.5105
Brugia malayi Sex muscle abnormal protein 5 0.026 0.1845 0.1845
Echinococcus granulosus NCK adaptor protein 0.026 0.1845 0.1845
Loa Loa (eye worm) hypothetical protein 0.026 0.1845 0.1845
Echinococcus multilocularis proto oncogene tyrosine protein kinase LCK 0.055 0.7695 0.7695
Echinococcus multilocularis tyrosine protein kinase Src64B 0.055 0.7695 0.7695
Echinococcus multilocularis tyrosine protein kinase Fgr 0.055 0.7695 0.7695
Loa Loa (eye worm) TK protein kinase 0.029 0.2448 0.2448
Schistosoma mansoni tyrosine kinase 0.055 0.7695 0.7695
Schistosoma mansoni adapter molecule crk 0.026 0.1845 0.1845
Schistosoma mansoni tyrosine kinase 0.0297 0.259 0.259
Echinococcus multilocularis tyrosine protein kinase lyn tyrosine protein kinase blk 0.055 0.7695 0.7695
Brugia malayi SRC-1 0.055 0.7695 0.7695
Echinococcus multilocularis tyrosine protein kinase Abl 0.0297 0.259 0.259
Echinococcus granulosus tyrosine protein kinase Src42A 0.055 0.7695 0.7695
Echinococcus granulosus c src tyrosine kinase 0.0297 0.259 0.259
Schistosoma mansoni tyrosine kinase 0.0297 0.259 0.259
Loa Loa (eye worm) sex muscle abnormal protein 5 0.026 0.1845 0.1845
Echinococcus granulosus growth factor receptor bound protein 2 0.026 0.1845 0.1845
Echinococcus multilocularis tyrosine protein kinase Fyn 0.055 0.7695 0.7695
Echinococcus multilocularis tyrosine protein kinase Src42A 0.055 0.7695 0.7695
Echinococcus granulosus tyrosine protein kinase Fyn 0.055 0.7695 0.7695
Echinococcus multilocularis tyrosine protein kinase Btk29A 0.0297 0.259 0.259
Entamoeba histolytica protein kinase, putative 0.029 0.2448 1
Schistosoma mansoni tyrosine kinase 0.055 0.7695 0.7695
Echinococcus granulosus tyrosine kinase|tyrosine protein kinase Fyn 0.0422 0.5105 0.5105
Echinococcus granulosus tyrosine protein kinase Btk29A 0.0297 0.259 0.259
Echinococcus multilocularis growth factor receptor bound protein 2 0.026 0.1845 0.1845
Echinococcus multilocularis tyrosine protein kinase Fyn 0.055 0.7695 0.7695
Echinococcus granulosus tyrosine protein kinase Lyn 0.055 0.7695 0.7695
Brugia malayi Tyrosine-protein kinase abl-1 0.0297 0.259 0.259
Echinococcus granulosus tyrosine protein kinase HCK 0.029 0.2448 0.2448
Echinococcus granulosus proto oncogene tyrosine protein kinase LCK 0.055 0.7695 0.7695
Echinococcus multilocularis tyrosine protein kinase Srms 0.0422 0.5105 0.5105
Onchocerca volvulus Vesicular acetylcholine transporter homolog 0.0664 1 1
Schistosoma mansoni vesicular acetylcholine transporter 0.0664 1 1
Echinococcus granulosus 3'partial|tyrosine protein kinase Fgr 0.055 0.7695 0.7695
Echinococcus granulosus tyrosine protein kinase Blk 0.0422 0.5105 0.5105
Echinococcus multilocularis tyrosine protein kinase Fyn 0.055 0.7695 0.7695
Echinococcus multilocularis tyrosine protein kinase HCK 0.029 0.2448 0.2448
Echinococcus granulosus vesicular acetylcholine transporter 0.0664 1 1
Echinococcus multilocularis c src tyrosine kinase 0.0297 0.259 0.259
Loa Loa (eye worm) vesicular acetylcholine transporter unc-17 0.0664 1 1
Brugia malayi protein-tyrosine kinase 0.0422 0.5105 0.5105
Echinococcus multilocularis vesicular acetylcholine transporter 0.0664 1 1
Echinococcus multilocularis tyrosine protein kinase lyn lyn a protein tyrosine kinase lymphocyte specific protein tyrosine kinase 0.055 0.7695 0.7695
Echinococcus granulosus tyrosine kinase 0.0422 0.5105 0.5105

Activities

Activity type Activity value Assay description Source Reference
AUC (functional) = 64 ug min m-1 pharmacokinetics in female BALB/c mice measured as AUC after 20 mg/kg iv administration ChEMBL. 11806724
AUC (functional) = 64 ug min m-1 pharmacokinetics in female BALB/c mice measured as AUC after 20 mg/kg iv administration ChEMBL. 11806724
AUC (functional) = 114 ug min m-1 pharmacokinetics in female BALB/c mice measured as AUC after 50 mg/kg Preoral administration ChEMBL. 11806724
AUC (functional) = 114 ug min m-1 pharmacokinetics in female BALB/c mice measured as AUC after 50 mg/kg Preoral administration ChEMBL. 11806724
AUC (functional) = 156 ug min m-1 pharmacokinetics in female BALB/c mice measured as AUC after 50 mg/kg iv administration ChEMBL. 11806724
AUC (functional) = 156 ug min m-1 pharmacokinetics in female BALB/c mice measured as AUC after 50 mg/kg iv administration ChEMBL. 11806724
Cl (functional) = 6.3 ml min-1 pharmacokinetics in female BALB/c mice measured as Cl after 20 mg/kg iv administration ChEMBL. 11806724
Cl (functional) = 6.3 ml min-1 pharmacokinetics in female BALB/c mice measured as Cl after 20 mg/kg iv administration ChEMBL. 11806724
Cl (functional) = 6.4 ml min-1 pharmacokinetics in female BALB/c mice measured as Cl after 50 mg/kg iv administration ChEMBL. 11806724
Cl (functional) = 6.4 ml min-1 pharmacokinetics in female BALB/c mice measured as Cl after 50 mg/kg iv administration ChEMBL. 11806724
Cmax (functional) = 0.35 ug ml-1 pharmacokinetics in female BALB/c mice measured as Cmax after 50 mg/kg Preoral administration ChEMBL. 11806724
Cmax (functional) = 0.35 ug ml-1 pharmacokinetics in female BALB/c mice measured as Cmax after 50 mg/kg Preoral administration ChEMBL. 11806724
Cmax (functional) = 0.8 ug ml-1 pharmacokinetics in female BALB/c mice measured as Cmax after 20 mg/kg iv administration ChEMBL. 11806724
Cmax (functional) = 0.8 ug ml-1 pharmacokinetics in female BALB/c mice measured as Cmax after 20 mg/kg iv administration ChEMBL. 11806724
Cmax (functional) = 2.9 ug ml-1 pharmacokinetics in female BALB/c mice measured as Cmax after 50 mg/kg iv administration ChEMBL. 11806724
Cmax (functional) = 2.9 ug ml-1 pharmacokinetics in female BALB/c mice measured as Cmax after 50 mg/kg iv administration ChEMBL. 11806724
F (functional) = 72 % pharmacokinetics in female BALB/c mice measured as bioavailability (F) after 50 mg/kg peroral administration ChEMBL. 11806724
F (functional) = 72 % pharmacokinetics in female BALB/c mice measured as bioavailability (F) after 50 mg/kg peroral administration ChEMBL. 11806724
IC50 (functional) = 1.2 nM Inhibitory activity against drug resistant H69/LX4 line overexpressing P-glycoprotein ChEMBL. 11806725
IC50 (functional) = 1.2 nM Inhibitory activity against drug resistant H69/LX4 line overexpressing P-glycoprotein ChEMBL. 11806725
IC50 (functional) = 10 nM Inhibitory activity against murine P388 leukemia (P388) cells. ChEMBL. 11806725
IC50 (functional) = 10 nM Inhibitory activity against murine P388 leukemia (P388) cells. ChEMBL. 11806725
IC50 (functional) = 10.1 nM Cytotoxicity measured using the COR-L23 parental (COR-L23/P) human non small cell lung carcinoma cell line ChEMBL. 11806724
IC50 (functional) = 10.1 nM Cytotoxicity measured using the COR-L23 parental (COR-L23/P) human non small cell lung carcinoma cell line ChEMBL. 11806724
IC50 (functional) = 12.1 nM Cytotoxicity measured with the drug resistant human non small cell lung carcinoma cell line COR-L23 (COR-L23/R) which over expresses multidrug resistance associated with protein(MRP) ChEMBL. 11806724
IC50 (functional) = 12.1 nM Cytotoxicity measured with the drug resistant human non small cell lung carcinoma cell line COR-L23 (COR-L23/R) which over expresses multidrug resistance associated with protein(MRP) ChEMBL. 11806724
IC50 (functional) = 23 nM Cytotoxicity measured using the H69 parental (H69/P) human small cell lung carcinoma cell line ChEMBL. 11806724
IC50 (functional) = 23 nM Inhibitory activity against parental human small cell lung carcinoma cell line (H69P) ChEMBL. 11806725
IC50 (functional) = 23 nM Cytotoxicity measured using the H69 parental (H69/P) human small cell lung carcinoma cell line ChEMBL. 11806724
IC50 (functional) = 23 nM Inhibitory activity against parental human small cell lung carcinoma cell line (H69P) ChEMBL. 11806725
IC50 (functional) = 29 nM Cytotoxicity measured using the drug resistant, P-glycoprotein (Pgp) expressing human small cell lung carcinoma cell line H69/LX4 ChEMBL. 11806724
IC50 (functional) = 29 nM Cytotoxicity measured using the drug resistant, P-glycoprotein (Pgp) expressing human small cell lung carcinoma cell line H69/LX4 ChEMBL. 11806724
Kel (functional) = 0.002 min-1 pharmacokinetics in female BALB/c mice measured as Kel after 50 mg/kg Preoral administration ChEMBL. 11806724
Kel (functional) = 0.002 min-1 pharmacokinetics in female BALB/c mice measured as Kel after 50 mg/kg Preoral administration ChEMBL. 11806724
Kel (functional) = 0.003 min-1 pharmacokinetics in female BALB/c mice measured as Kel after 50 mg/kg iv administration ChEMBL. 11806724
Kel (functional) = 0.003 min-1 pharmacokinetics in female BALB/c mice measured as Kel after 50 mg/kg iv administration ChEMBL. 11806724
Kel (functional) = 0.0044 min-1 pharmacokinetics in female BALB/c mice measured as Kel after 20 mg/kg iv administration ChEMBL. 11806724
Kel (functional) = 0.0044 min-1 pharmacokinetics in female BALB/c mice measured as Kel after 20 mg/kg iv administration ChEMBL. 11806724
Rf (functional) = 1.2 Rf is the resistance factor and is the ratio of the IC50 on the resistant cell line over the IC50 on the parental H69/P cell line ChEMBL. 11806724
Rf (ADMET) = 1.2 Rf is the resistance factor and is the ratio of the IC50 on the resistant cell line over the IC50 on the parental COR-L23/P cell line ChEMBL. 11806724
Vss (functional) = 1.3 l pharmacokinetics in female BALB/c mice measured as Vss after 20 mg/kg iv administration ChEMBL. 11806724
Vss (functional) = 1.3 l pharmacokinetics in female BALB/c mice measured as Vss after 20 mg/kg iv administration ChEMBL. 11806724
Vss (functional) = 1.9 l pharmacokinetics in female BALB/c mice measured as Vss after 50 mg/kg iv administration ChEMBL. 11806724
Vss (functional) = 1.9 l pharmacokinetics in female BALB/c mice measured as Vss after 50 mg/kg iv administration ChEMBL. 11806724

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Mus musculus ChEMBL23 11806725
Homo sapiens ChEMBL23 11806724

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

2 literature references were collected for this gene.

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