Detailed information for compound 509150

Basic information

Technical information
  • TDR Targets ID: 509150
  • Name: 3,4,5-trimethoxy-N-[2-[3-(piperazin-1-ylmethy l)imidazo[2,1-b][1,3]thiazol-6-yl]phenyl]benz amide
  • MW: 507.605 | Formula: C26H29N5O4S
  • H donors: 2 H acceptors: 2 LogP: 3.49 Rotable bonds: 9
    Rule of 5 violations (Lipinski): 2
  • SMILES: COc1cc(cc(c1OC)OC)C(=O)Nc1ccccc1c1cn2c(n1)scc2CN1CCNCC1
  • InChi: 1S/C26H29N5O4S/c1-33-22-12-17(13-23(34-2)24(22)35-3)25(32)28-20-7-5-4-6-19(20)21-15-31-18(16-36-26(31)29-21)14-30-10-8-27-9-11-30/h4-7,12-13,15-16,27H,8-11,14H2,1-3H3,(H,28,32)
  • InChiKey: SBEWVVLMFLTQFE-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • 3,4,5-trimethoxy-N-[2-[3-(piperazin-1-ylmethyl)imidazo[2,1-b]thiazol-6-yl]phenyl]benzamide
  • 3,4,5-trimethoxy-N-[2-[3-(1-piperazinylmethyl)-6-imidazo[2,1-b]thiazolyl]phenyl]benzamide
  • 3,4,5-trimethoxy-N-[2-[3-(piperazinomethyl)imidazo[2,1-b]thiazol-6-yl]phenyl]benzamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens sirtuin 1 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Candida albicans one of two genes similar to S. cerevisiae SIR2 (YDL042C) NAD+-dependent histone deacetylase Get druggable targets OG5_129944 All targets in OG5_129944
Brugia malayi NAD-dependent deacetylase SIRT1 Get druggable targets OG5_129944 All targets in OG5_129944
Trichomonas vaginalis chromatin regulatory protein sir2, putative Get druggable targets OG5_129944 All targets in OG5_129944
Echinococcus granulosus NAD dependent deacetylase sirtuin 1 Get druggable targets OG5_129944 All targets in OG5_129944
Schistosoma japonicum ko:K01463 sirtuin 1 (silent mating type information regulation 2, homolog) 1 [EC:3.5.1.-], putative Get druggable targets OG5_129944 All targets in OG5_129944
Giardia lamblia NAD-dependent histone deacetylase Sir2 Get druggable targets OG5_129944 All targets in OG5_129944
Candida albicans one of two genes similar to S. cerevisiae SIR2 (YDL042C) NAD+-dependent histone deacetylase Get druggable targets OG5_129944 All targets in OG5_129944
Schistosoma japonicum expressed protein Get druggable targets OG5_129944 All targets in OG5_129944
Trichomonas vaginalis chromatin regulatory protein sir2, putative Get druggable targets OG5_129944 All targets in OG5_129944
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_129944 All targets in OG5_129944
Echinococcus multilocularis NAD dependent deacetylase sirtuin 1 Get druggable targets OG5_129944 All targets in OG5_129944
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_129944 All targets in OG5_129944
Trichomonas vaginalis chromatin regulatory protein sir2, putative Get druggable targets OG5_129944 All targets in OG5_129944
Trichomonas vaginalis chromatin regulatory protein sir2, putative Get druggable targets OG5_129944 All targets in OG5_129944
Schistosoma mansoni chromatin regulatory protein sir2 Get druggable targets OG5_129944 All targets in OG5_129944
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 jmjC domain containing protein 0.006 0.1518 0.1625
Toxoplasma gondii histone lysine methyltransferase SET/SUV39 0.0031 0.0139 0.0568
Schistosoma mansoni hypothetical protein 0.0168 0.6544 1
Echinococcus granulosus peptidase Clp S14 family 0.0052 0.1158 0.166
Schistosoma mansoni hypothetical protein 0.0168 0.6544 1
Giardia lamblia NAD-dependent histone deacetylase Sir2 0.0151 0.5753 0.5
Echinococcus granulosus histone lysine methyltransferase setb 0.0031 0.0139 0.0081
Loa Loa (eye worm) pre-SET domain-containing protein family protein 0.0213 0.863 1
Loa Loa (eye worm) hypothetical protein 0.0131 0.4828 0.5522
Wolbachia endosymbiont of Brugia malayi ATP-dependent Clp protease proteolytic subunit 0.008 0.2442 0.5
Echinococcus granulosus NAD dependent deacetylase sirtuin 1 0.0151 0.5753 0.8776
Echinococcus granulosus Transcription factor JmjC domain containing protein 0.006 0.1518 0.2217
Mycobacterium leprae PROBABLE ATP-DEPENDENT CLP PROTEASE PROTEOLYTIC SUBUNIT 2 CLPP2 (ENDOPEPTIDASE CLP 2) 0.008 0.2442 1
Echinococcus multilocularis geminin 0.0168 0.6544 1
Chlamydia trachomatis ATP-dependent Clp protease proteolytic subunit 0.008 0.2442 0.5
Echinococcus multilocularis ATP dependent Clp protease proteolytic subunit 0.008 0.2442 0.3596
Mycobacterium leprae PROBABLE ATP-DEPENDENT CLP PROTEASE PROTEOLYTIC SUBUNIT 1 CLPP1 (ENDOPEPTIDASE CLP) 0.0052 0.1158 0.4744
Mycobacterium ulcerans ATP-dependent Clp protease proteolytic subunit 0.008 0.2442 0.5
Schistosoma mansoni peptidase Clp (S14 family) 0.008 0.2442 0.3596
Echinococcus multilocularis retinoic acid receptor rxr beta a retinoic acid receptor rxr alpha a retinoic acid receptor rxr alpha 0.0101 0.3435 0.5147
Plasmodium vivax SET domain protein, putative 0.0031 0.0139 0.0568
Echinococcus granulosus retinoic acid receptor rxr beta a 0.0105 0.362 0.5473
Toxoplasma gondii ATP-dependent Clp endopeptidase, proteolytic subunit ClpP domain-containing protein 0.008 0.2442 1
Brugia malayi NAD-dependent deacetylase SIRT1 0.0151 0.5753 0.6612
Echinococcus multilocularis peptidase Clp (S14 family) 0.0052 0.1158 0.1592
Toxoplasma gondii ATP-dependent Clp endopeptidase, proteolytic subunit ClpP domain-containing protein 0.008 0.2442 1
Mycobacterium tuberculosis Probable ATP-dependent CLP protease proteolytic subunit 1 ClpP1 (endopeptidase CLP) 0.0052 0.1158 0.5
Chlamydia trachomatis ATP-dependent Clp protease proteolytic subunit 0.008 0.2442 0.5
Brugia malayi Probable ClpP-like protease 0.008 0.2442 0.2712
Loa Loa (eye worm) hypothetical protein 0.008 0.2442 0.2712
Schistosoma mansoni jumonji/arid domain-containing protein 0.006 0.1518 0.2154
Plasmodium vivax ATP-dependent Clp protease proteolytic subunit, putative 0.008 0.2442 1
Brugia malayi jmjC domain containing protein 0.006 0.1518 0.1625
Echinococcus granulosus ATP dependent Clp protease proteolytic subunit 0.008 0.2442 0.3648
Loa Loa (eye worm) hypothetical protein 0.0151 0.5753 0.6612
Echinococcus granulosus geminin 0.0168 0.6544 1
Echinococcus multilocularis Transcription factor, JmjC domain containing protein 0.006 0.1518 0.2154
Treponema pallidum ATP-dependent Clp protease proteolytic subunit 0.008 0.2442 1
Echinococcus multilocularis NAD dependent deacetylase sirtuin 1 0.0151 0.5753 0.8766
Brugia malayi Pre-SET motif family protein 0.0213 0.863 1
Echinococcus granulosus lysine specific demethylase 5A 0.006 0.1518 0.2217
Plasmodium falciparum ATP-dependent Clp protease proteolytic subunit 0.008 0.2442 1
Trichomonas vaginalis set domain proteins, putative 0.0242 1 1
Schistosoma mansoni jumonji domain containing protein 0.006 0.1518 0.2154
Echinococcus multilocularis lysine specific demethylase 5A 0.006 0.1518 0.2154
Schistosoma mansoni retinoic acid receptor RXR 0.0105 0.362 0.5436
Schistosoma mansoni chromatin regulatory protein sir2 0.0151 0.5753 0.8766
Loa Loa (eye worm) jmjC domain-containing protein 0.006 0.1518 0.1625
Mycobacterium ulcerans ATP-dependent Clp protease proteolytic subunit 0.008 0.2442 0.5
Mycobacterium tuberculosis Probable ATP-dependent CLP protease proteolytic subunit 2 ClpP2 (endopeptidase CLP 2) 0.0052 0.1158 0.5
Schistosoma mansoni jumonji/arid domain-containing protein 0.006 0.1518 0.2154

Activities

Activity type Activity value Assay description Source Reference
Activity (binding) 0 Activation of SIRT1 in human U2OS cells assessed as decrease in deacetylation level at 10 uM ChEMBL. 18046409
Activity (binding) 0 Activation of human SIRT1 (unknown origin) assessed as decrease in Km of enzyme for acetylated peptide substrate by mass spectrometry assay ChEMBL. 18046409
Activity (binding) = 271 % Activation of human SIRT1 expressed in Escherichia coli BL21Start assessed as maximum activation of enzyme activity by mass spectrometry assay ChEMBL. 19199480
Activity (binding) = 447 % Activation of human SIRT1 expressed in Escherichia coli BL21 by mass spectrometry assay ChEMBL. 18046409
Activity (binding) = 447 % Activation of human SIRT1 expressed in Escherichia coli BL21 by mass spectrometry assay ChEMBL. 18046409
Activity (binding) = 1.8 uM Activation of human SIRT1 expressed in Escherichia coli BL21Start assessed as concentration required to increase 50% enzyme activity by mass spectrometry assay ChEMBL. 19199480
AUC (ADMET) = 45000 ng.hr/ml AUC in C57BL/6 mouse at 100 mg/kg, po or 10 mg/kg, iv ChEMBL. 19199480
Cmax (ADMET) = 14 uM Cmax in C57BL/6 mouse at 100 mg/kg, po or 10 mg/kg, iv ChEMBL. 19199480
EC50 (binding) = 1.8 uM Activation of N-terminal His6-tagged SIRT1 (156 to 664 amino acid residues) (unknown origin) expressed in Escherichia coli BL21(DE3) using ac-RHKKac-AMC as substrate after 45 mins by fluorometric analysis ChEMBL. 23316803
EC50 (binding) = 2.9 uM Activation of human SIRT1 expressed in Escherichia coli BL21 by mass spectrometry assay ChEMBL. 18046409
EC50 (binding) = 2.9 uM Activation of human SIRT1 expressed in Escherichia coli BL21 by mass spectrometry assay ChEMBL. 18046409
EC50 (binding) > 300 uM Activation of SIRT2 (unknown origin) by mass spectrometry assay ChEMBL. 18046409
EC50 (binding) > 300 uM Activation of SIRT3 (unknown origin) by mass spectrometry assay ChEMBL. 18046409
EC50 (binding) > 300 uM Activation of SIRT2 (unknown origin) by mass spectrometry assay ChEMBL. 18046409
EC50 (binding) > 300 uM Activation of SIRT3 (unknown origin) by mass spectrometry assay ChEMBL. 18046409
F (ADMET) = 40 % Oral bioavailability in C57BL/6 mouse at 100 mg/kg ChEMBL. 19199480
Kd (binding) = 16.2 uM Binding affinity to human SIRT1 by isothermal titration calorimetry ChEMBL. 18046409
Kd (binding) = 16.2 uM Binding affinity to human SIRT1 by isothermal titration calorimetry ChEMBL. 18046409
Kd (binding) = 16.2 uM Binding affinity to SIRT1 ChEMBL. 19199480
max activation (binding) = 271 % Activation of N-terminal His6-tagged SIRT1 (156 to 664 amino acid residues) (unknown origin) expressed in Escherichia coli BL21(DE3) using ac-RHKKac-AMC as substrate at 50 uM after 45 mins by fluorimetric analysis relative to control ChEMBL. 23316803
T1/2 (ADMET) = 6 hr Terminal half life in C57BL/6 mouse at 100 mg/kg, po or 10 mg/kg, iv ChEMBL. 19199480

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

3 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.