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
Network
Hover on a compound node to display the structore
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 |
|---|---|---|---|
| Treponema pallidum | penicillin-binding protein (pbp-2) | Get druggable targets OG5_129763 | All targets in OG5_129763 |
| Neospora caninum | 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 |
| 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 |
| Trichomonas vaginalis | conserved hypothetical protein | 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
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.
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
- ChEMBL: CHEMBL422426
- PubChem: 9890833
Bibliographic References
1 literature reference was collected for this gene.
If you have references for this compound, please enter them in a user comment (below) or Contact us.