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CHEMBL123481

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C[C@]1(/C=C/C[n+]2ccccc2)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O.O=S(=O)([O-])C(F)(F)F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL123481
Phase Preclinical
Structure Type MOL
InChI Key GNFLSCHXXGDGTG-GHTMCSQZSA-N
Parent Compound CHEMBL1180354
Active Moiety CHEMBL1180354
9
Targets
18
Activities
1
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

337.4
MW (Da)
-0.27
ALogP
4
HBA
1
HBD
95.6
PSA (Ų)
0.46
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H17F3N2O8S2
MW 486.45
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 0.59

Activity Summary

IC50 18 meas. best 6.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.85 6.002 140.0 5
Beta-lactamase
CHEMBL5633
 IC50 5.75 5.75 1800.0 1
Penicillin-binding protein 2
CHEMBL3825
 IC50 5.41 5.1025 3900.0 4
Citrobacter freundii
CHEMBL612615
 IC50 5.4 5.4 4000.0 1
Enterobacter cloacae
CHEMBL349
 IC50 5.1 5.1 8000.0 1
Penicillin-binding protein 4
CHEMBL2549
 IC50 4.82 4.82 15000.0 1
Beta-lactamase
CHEMBL1255130
 IC50 4.8 4.8 16000.0 1
Penicillin-binding protein 2b
CHEMBL2565
 IC50 4.52 4.52 30000.0 1
Beta-lactamase
CHEMBL5031
 IC50 4.12 4.12 75000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 140.0 nM 6.85 Compound was tested for inhibition of TEM-3, class A of beta-lactamases. 8809160
Unchecked IC50 = 250.0 nM 6.6 Compound was tested for inhibition of pTEM-3 from Escherichia coli in combinatio... 8809160
Unchecked IC50 = 500.0 nM 6.3 Compound was tested for inhibition of pTEM-4 from Escherichia coli in combinatio... 8809160
Beta-lactamase IC50 = 1800.0 nM 5.75 Compound was tested for inhibition of Bacillus licheniformis 749/C, class A of B... 8809160
Unchecked IC50 = 3600.0 nM 5.44 Compound was tested for inhibition of TEM-1, class A of beta-lactamases. 8809160
Penicillin-binding protein 2 IC50 = 3900.0 nM 5.41 Compound was tested for inhibition of Penicillin-binding protein 2 from Streptoc... 8809160
Citrobacter freundii IC50 = 4000.0 nM 5.4 Compound was tested for inhibition of Citrobacter freundii 1928 in combination w... 8809160
Enterobacter cloacae IC50 = 8000.0 nM 5.1 Compound was tested for inhibition of Ent. cloacae 908R in combination with Ceft... 8809160
Penicillin-binding protein 2 IC50 = 8200.0 nM 5.09 Compound was tested for inhibition of 503 Cephalosporin resistant mutants of Pen... 8809160
Penicillin-binding protein 2 IC50 = 8100.0 nM 5.09 Compound was tested for inhibition of 604 Cephalosporin resistant mutants of Pen... 8809160
Unchecked IC50 = 15000.0 nM 4.82 Compound was tested for inhibition of Penicillin-binding protein 1 from Staphylo... 8809160
Penicillin-binding protein 2 IC50 = 15000.0 nM 4.82 Compound was tested for inhibition of Penicillin-binding protein 2 from Staphylo... 8809160
Penicillin-binding protein 4 IC50 = 15000.0 nM 4.82 Compound was tested for inhibition of Penicillin-binding protein 4 from Staphylo... 8809160
Beta-lactamase IC50 = 16000.0 nM 4.8 Compound was tested for inhibition of Citrobacter freundii 1928, class C of Beta... 8809160
Penicillin-binding protein 2b IC50 = 30000.0 nM 4.52 Compound was tested for inhibition of Penicillin-binding protein 3 from Staphylo... 8809160
Beta-lactamase IC50 = 75000.0 nM 4.12 Compound was tested for inhibition of Pseudomonas aeruginosa 18SH, class C of Be... 8809160

Literature References

PubMed DOI Target Context # Activities
8809160 10.1021/jm9601967 Unchecked 5
8809160 10.1021/jm9601967 Beta-lactamase 4
8809160 10.1021/jm9601967 Penicillin-binding protein 2 4
8809160 10.1021/jm9601967 Penicillin-binding protein 2b 2
8809160 10.1021/jm9601967 Enterobacter cloacae 1
8809160 10.1021/jm9601967 Citrobacter freundii 1
8809160 10.1021/jm9601967 Pseudomonas aeruginosa 1
8809160 10.1021/jm9601967 Penicillin-binding protein 1B 1
8809160 10.1021/jm9601967 Peptidoglycan D,D-transpeptidase MrdA 1
8809160 10.1021/jm9601967 Penicillin-binding protein 4 1

Data from ChEMBL 36 via Core Engine