Detailed information for compound 182241

Basic information

Technical information
  • TDR Targets ID: 182241
  • Name: (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[7-[(3-meth ylimidazol-3-ium-1-yl)methyl]-9-oxofluoren-3- yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-car boxylate
  • MW: 469.489 | Formula: C27H23N3O5
  • H donors: 1 H acceptors: 5 LogP: 2.81 Rotable bonds: 5
    Rule of 5 violations (Lipinski): 1
  • SMILES: Cn1cc[n+](c1)Cc1ccc2c(c1)C(=O)c1c2cc(cc1)C1=C(C(=O)[O-])N2[C@H](C1)[C@H](C2=O)[C@H](O)C
  • InChi: 1S/C27H23N3O5/c1-14(31)23-22-11-19(24(27(34)35)30(22)26(23)33)16-4-6-18-20(10-16)17-5-3-15(9-21(17)25(18)32)12-29-8-7-28(2)13-29/h3-10,13-14,22-23,31H,11-12H2,1-2H3/t14-,22-,23-/m1/s1
  • InChiKey: ZPXTVRPOCJUEHR-BQKRCXSJSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[7-[(3-methylimidazol-3-ium-1-yl)methyl]-9-oxo-fluoren-3-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  • (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[7-[(3-methyl-1-imidazol-3-iumyl)methyl]-9-oxo-3-fluorenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  • (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-keto-3-[9-keto-7-[(3-methylimidazol-3-ium-1-yl)methyl]fluoren-3-yl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  • L 695256
  • (5R,6S)-6-(1-hydroxyethyl)-3-[7-[(3-methylimidazol-3-ium-1-yl)methyl]-9-oxofluoren-3-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  • (5R,6S)-6-(1-hydroxyethyl)-3-[7-[(3-methylimidazol-3-ium-1-yl)methyl]-9-oxo-fluoren-3-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  • (5R,6S)-6-(1-hydroxyethyl)-3-[7-[(3-methyl-1-imidazol-3-iumyl)methyl]-9-oxo-3-fluorenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  • (5R,6S)-6-(1-hydroxyethyl)-7-keto-3-[9-keto-7-[(3-methylimidazol-3-ium-1-yl)methyl]fluoren-3-yl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Staphylococcus aureus PBP2 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Neospora caninum hypothetical protein Get druggable targets OG5_129763 All targets in OG5_129763
Mycobacterium tuberculosis Probable bifunctional penicillin-binding protein 1A/1B PonA1 (murein polymerase) (PBP1): penicillin-insensitive transglycosylase Get druggable targets OG5_129763 All targets in OG5_129763
Treponema pallidum penicillin-binding protein (pbp-2) Get druggable targets OG5_129763 All targets in OG5_129763
Trichomonas vaginalis conserved hypothetical protein Get druggable targets OG5_129763 All targets in OG5_129763
Mycobacterium ulcerans bifunctional penicillin-binding protein 1A/1B PonA1 Get druggable targets OG5_129763 All targets in OG5_129763
Mycobacterium leprae PROBABLE BIFUNCTIONAL PENICILLIN-BINDING PROTEIN 1A/1B PONA1 (MUREIN POLYMERASE) (PBP1): PENICILLIN-INSENSITIVE TRANSGLYCOSYLASE Get druggable targets OG5_129763 All targets in OG5_129763
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Mycobacterium leprae PROBABLE BIFUNCTIONAL MEMBRANE-ASSOCIATED PENICILLIN-BINDING PROTEIN 1A/1B PONA2 (MUREIN POLYMERASE) [INCLUDES: PENICILLIN-INSEN PBP2   727 aa 593 aa 22.9 %
Mycobacterium ulcerans bifunctional membrane-associated penicillin-binding protein 1A/1B PonA2 PBP2   727 aa 587 aa 23.2 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Trypanosoma cruzi glyceraldehyde 3-phosphate dehydrogenase, putative 0.0284 0.388 1
Leishmania major glyceraldehyde 3-phosphate dehydrogenase, glycosomal 0.0284 0.388 1
Trichomonas vaginalis glyceraldehyde 3-phosphate dehydrogenase, putative 0.0284 0.388 0.3877
Schistosoma mansoni glyceraldehyde-3-phosphate dehydrogenase (phosphorylating) 0.0284 0.388 0.5
Schistosoma mansoni glyceraldehyde-3-phosphate dehydrogenase (phosphorylating) 0.0284 0.388 0.5
Toxoplasma gondii glyceraldehyde-3-phosphate dehydrogenase GAPDH1 0.0284 0.388 0.5
Trypanosoma cruzi glyceraldehyde 3-phosphate dehydrogenase, cytosolic, putative 0.0284 0.388 1
Entamoeba histolytica glyceraldehyde-3-phosphate dehydrogenase, putative 0.0284 0.388 0.5
Plasmodium falciparum glyceraldehyde-3-phosphate dehydrogenase 0.0284 0.388 0.5
Mycobacterium ulcerans bifunctional penicillin-binding protein 1A/1B PonA1 0.0439 1 1
Trypanosoma brucei glyceraldehyde 3-phosphate dehydrogenase, cytosolic 0.0284 0.388 1
Trichomonas vaginalis glyceraldehyde 3-phosphate dehydrogenase, putative 0.0284 0.388 0.3877
Toxoplasma gondii glyceraldehyde-3-phosphate dehydrogenase GAPDH2 0.0284 0.388 0.5
Leishmania major glyceraldehyde 3-phosphate dehydrogenase, glycosomal 0.0284 0.388 1
Trypanosoma brucei glyceraldehyde 3-phosphate dehydrogenase, glycosomal 0.0284 0.388 1
Trichomonas vaginalis glyceraldehyde 3-phosphate dehydrogenase, putative 0.0284 0.388 0.3877
Loa Loa (eye worm) glyceraldehyde-3-phosphate dehydrogenase 0.0196 0.04 1
Trichomonas vaginalis glyceraldehyde 3-phosphate dehydrogenase, putative 0.0284 0.388 0.3877
Trypanosoma cruzi glyceraldehyde 3-phosphate dehydrogenase, putative 0.0284 0.388 1
Trypanosoma brucei glyceraldehyde 3-phosphate dehydrogenase, glycosomal 0.0284 0.388 1
Mycobacterium ulcerans glyceraldehyde 3-phosphate dehydrogenase Gap 0.0284 0.388 0.211
Mycobacterium tuberculosis Probable bifunctional membrane-associated penicillin-binding protein 1A/1B PonA2 (murein polymerase) [includes: penicillin-insen 0.0243 0.2244 1
Entamoeba histolytica glyceraldehyde-3-phosphate dehydrogenase, putative 0.0284 0.388 0.5
Schistosoma mansoni glyceraldehyde-3-phosphate dehydrogenase (phosphorylating) 0.0284 0.388 0.5
Chlamydia trachomatis glyceraldehyde-3-phosphate dehydrogenase 0.0284 0.388 0.5
Plasmodium vivax glyceraldehyde-3-phosphate dehydrogenase, putative 0.0284 0.388 0.5
Trypanosoma cruzi glyceraldehyde 3-phosphate dehydrogenase, cytosolic, putative 0.0284 0.388 1
Trichomonas vaginalis glyceraldehyde 3-phosphate dehydrogenase, putative 0.0284 0.388 0.3877
Echinococcus granulosus glyceraldehyde 3 phosphate dehydrogenase 0.0284 0.388 1
Schistosoma mansoni glyceraldehyde-3-phosphate dehydrogenase (phosphorylating) 0.0284 0.388 0.5
Brugia malayi Glyceraldehyde 3-phosphate dehydrogenase 0.0284 0.388 0.5
Trypanosoma cruzi glyceraldehyde 3-phosphate dehydrogenase, putative 0.0284 0.388 1
Echinococcus multilocularis glyceraldehyde 3 phosphate dehydrogenase 0.0284 0.388 1
Loa Loa (eye worm) glyceraldehyde-3-phosphate dehydrogenase 0.0196 0.04 1
Trypanosoma cruzi glyceraldehyde 3-phosphate dehydrogenase, putative 0.0284 0.388 1
Trypanosoma cruzi glyceraldehyde 3-phosphate dehydrogenase, cytosolic, putative 0.0284 0.388 1
Treponema pallidum penicillin-binding protein (pbp-2) 0.0439 1 1
Wolbachia endosymbiont of Brugia malayi glyceraldehyde-3-phosphate dehydrogenase, GapA 0.0284 0.388 0.5
Echinococcus granulosus glyceraldehyde 3 phosphate dehydrogenase 0.0284 0.388 1
Trichomonas vaginalis conserved hypothetical protein 0.0439 1 1
Echinococcus multilocularis glyceraldehyde 3 phosphate dehydrogenase 0.0284 0.388 1
Giardia lamblia Glyceraldehyde 3-phosphate dehydrogenase 0.0284 0.388 1
Entamoeba histolytica glyceraldehyde-3-phosphate dehydrogenase, putative 0.0284 0.388 0.5

Activities

Activity type Activity value Assay description Source Reference
AUC (ADMET) = 30.4 ug hr ml-1 AUC (area under curve) evaluated in Rhesus monkeys at the dose of 10 mg/kg by iv bolus injection ChEMBL. 10576693
Beta t1/2 (ADMET) = 1.17 hr Half life of the compound evaluated in Rhesus monkeys at the dose of 10 mg/kg by iv bolus injection ChEMBL. 10576693
ED50 (functional) = 0.034 mg kg-1 In vivo antibacterial activity against MSSA MB 2985 strain at the dose ~4 *10e7 cfu in brain heart broth along with antibiotic by sc administration at 0 hour in mice ChEMBL. 10576693
ED50 (functional) = 0.034 mg kg-1 In vivo antibacterial activity against MSSA MB 2985 strain at the dose ~4 *10e7 cfu in brain heart broth along with antibiotic by sc administration at 0 hour in mice ChEMBL. 10576693
ED50 (functional) = 0.92 mg kg-1 dose-1 In vivo antibacterial activity against MRSA 76 virginia strain at the dose ~1 *10e7 cfu in 5 percent hog gastric mucin along with antibiotic by sc administration at 0 and +4 hrs in mice ChEMBL. 10576693
ED50 (functional) = 0.92 mg kg-1 dose-1 In vivo antibacterial activity against MRSA 76 virginia strain at the dose ~1 *10e7 cfu in 5 percent hog gastric mucin along with antibiotic by sc administration at 0 and +4 hrs in mice ChEMBL. 10576693
GFR (ADMET) = 3.19 ml min-1 kg-1 Glomerular Filteration Rate(GFR) evaluated in Rhesus monkeys at the dose of 10 mg/kg by iv bolus injection ChEMBL. 10576693
IC50 (binding) = 0.5 ug ml-1 Binding affinity against PBP2a receptor by competition analysis with [3H]-benzylpenicillin using cell membrane fractions from the MRSA COL strain. ChEMBL. 10576693
IC50 (binding) = 0.5 ug ml-1 Binding affinity against PBP2a receptor by competition analysis with [3H]-benzylpenicillin using cell membrane fractions from the MRSA COL strain. ChEMBL. 10576693
MIC (functional) = 0.008 ug ml-1 In vivo antibacterial activity against MSSA MB 2985 strain at the dose ~4 *10e7 cfu in brain heart broth along with antibiotic by administration at 0 hour in mice ChEMBL. 10576693
MIC (functional) = 0.008 ug ml-1 In vivo antibacterial activity against MSSA MB 2985 strain at the dose ~4 *10e7 cfu in brain heart broth along with antibiotic by administration at 0 hour in mice ChEMBL. 10576693
MIC (functional) = 0.03 ug ml-1 Antibacterial activity against MSSA (Methicillin-sensitive Staphylococcus aureus) ChEMBL. 10576693
MIC (functional) < 0.03 ug ml-1 Antibacterial activity against penicillin-resistant S. pneumoniae ChEMBL. 10576693
MIC (functional) < 0.031 ug ml-1 Antibacterial activity against S. pyogenes ChEMBL. 10576693
MIC (functional) = 0.125 ug ml-1 Antibacterial activity against Enterococcus faecalis ChEMBL. 10576693
MIC (functional) = 1 ug ml-1 Antibacterial activity against vancomycin-resistant Enterococcus faecalis strain ChEMBL. 10576693
MIC (functional) = 1 ug ml-1 In vivo antibacterial activity against MRSA 76 virginia strain at the dose ~1 *10e7 cfu in 5 percent hog gastric mucin along with antibiotic by sc administration at 0 and +4 hrs in mice ChEMBL. 10576693
MIC (functional) = 1 ug ml-1 In vivo antibacterial activity against MRSA 76 virginia strain at the dose ~1 *10e7 cfu in 5 percent hog gastric mucin along with antibiotic by sc administration at 0 and +4 hrs in mice ChEMBL. 10576693
MIC (functional) = 1.37 ug ml-1 Antibacterial activity against Gram negative bacteria ChEMBL. 10576693
MIC (functional) = 4 ug ml-1 Antibacterial activity activity against vancomycin-resistant Enterococcal faecium strain ChEMBL. 10576693
MIC50 (functional) = 1 ug ml-1 Antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) ChEMBL. 10576693
MIC50 (functional) = 2 ug ml-1 Antibacterial activity against methicillin-resistant coagulase negative Staphylococci (MRCNS) ChEMBL. 10576693
MIC90 (functional) = 2 ug ml-1 Antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) ChEMBL. 10576693
MIC90 (functional) = 4 ug ml-1 Antibacterial activity against methicillin-resistant coagulase negative Staphylococci (MRCNS) ChEMBL. 10576693
Plasma clearance (ADMET) = 5.56 ml min-1 kg-1 Plasma clearance evaluated in Rhesus monkeys at the dose of 10 mg/kg by iv bolus injection ChEMBL. 10576693
Rate of hydrolysis (binding) = 0.078 Susceptibility of the compound to mammalian dehydropeptidas, DHP-1(Porcine) ChEMBL. 10576693
Rate of hydrolysis (binding) = 0.078 Susceptibility of the compound to mammalian dehydropeptidas, DHP-1(Porcine) ChEMBL. 10576693
Renal clearance (ADMET) = 2.34 ml min-1 kg-1 Renal clearance evaluated in Rhesus monkeys at the dose of 10 mg/kg by iv bolus injection ChEMBL. 10576693
Urinary recovery (ADMET) = 41 Urinary recovery evaluated in Rhesus monkeys at the dose of 10 mg/kg by iv bolus injection ChEMBL. 10576693

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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