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Compound Detail

CHEMBL333078

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C[C@]1(/C=C\C#N)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL333078
Phase Preclinical
Structure Type MOL
InChI Key JYGFUXUBGZBBAC-BJTZKDDDSA-N
9
Targets
15
Activities
2
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

270.3
MW (Da)
-0.74
ALogP
5
HBA
1
HBD
115.5
PSA (Ų)
0.52
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C10H10N2O5S
MW 270.27
Aromatic Rings 0
Heavy Atoms 18
NP-Likeness 0.67

Activity Summary

IC50 13 meas. best 6.52
Ki 2 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 7.0 6.85 100.0 2
Efflux transporter
CHEMBL1641337
 IC50 6.52 6.52 300.0 1
Class C beta-lactamase CMY-36
CHEMBL1641338
 IC50 6.52 6.52 300.0 1
Unchecked
CHEMBL612545
 IC50 6.52 6.19 300.0 3
Bacillus licheniformis
CHEMBL612626
 IC50 6.5 6.5 320.0 1
Beta-lactamase
CHEMBL2725
 IC50 6.16 5.32 700.0 3
Citrobacter freundii
CHEMBL612615
 IC50 5.7 5.7 2000.0 1
Enterobacter cloacae
CHEMBL349
 IC50 5.4 5.4 4000.0 1
Beta-lactamase ACC-4
CHEMBL5305
 IC50 4.99 4.99 10300.0 1
Pseudomonas aeruginosa
CHEMBL348
 IC50 4.8 4.8 16000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 100.0 nM 7.0 Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-2 using cephalothin as ... 19470510
Unchecked Ki = 200.0 nM 6.7 Inhibition of Escherichia coli MC4100 Beta-Lactamase CMY-30 using cephalothin as... 19470510
Efflux transporter IC50 = 300.0 nM 6.52 Inhibition of Salmonella enterica serotype Newport AM17274 cephalosporinase CMY-... 19104021
Class C beta-lactamase CMY-36 IC50 = 300.0 nM 6.52 Inhibition of Klebsiella pneumoniae HP205 cephalosporinase CMY-36 by UV spectrop... 19104021
Unchecked IC50 = 300.0 nM 6.52 Inhibition of CMY-2 by UV spectrophotometer in presence of 100 uM of cephalothin 19104021
Bacillus licheniformis IC50 = 320.0 nM 6.5 Compound was tested for inhibition of Bacillus licheniformis 749/C, class A of b... 8809160
Unchecked IC50 = 690.0 nM 6.16 Compound was tested for inhibition of TEM-3, class A of beta-lactamases. 8809160
Beta-lactamase IC50 = 700.0 nM 6.16 Compound was tested for inhibition of Citrobacter freundii 1928, class C of Beta... 8809160
Unchecked IC50 = 1300.0 nM 5.89 Compound was tested for inhibition of TEM-1, class A of beta-lactamases. 8809160
Citrobacter freundii IC50 = 2000.0 nM 5.7 Compound was tested for inhibition of Citrobacter freundii 1928 in combination w... 8809160
Enterobacter cloacae IC50 = 4000.0 nM 5.4 Compound was tested for inhibition of Ent. cloacae 908R in combination with Ceft... 8809160
Beta-lactamase IC50 = 7500.0 nM 5.12 Compound was tested for inhibition of Pseudomonas aeruginosa 18SH, class C of Be... 8809160
Beta-lactamase ACC-4 IC50 = 10300.0 nM 4.99 Inhibition of Escherichia coli beta-lactamase ACC4 17664321
Pseudomonas aeruginosa IC50 = 16000.0 nM 4.8 Compound was tested for inhibition of Pseudomonas aeruginosa 18SH in combination... 8809160
Beta-lactamase IC50 = 21000.0 nM 4.68 Compound was tested for inhibition of Escherichia coli AmpC, class C of Beta-lac... 8809160

Literature References

PubMed DOI Target Context # Activities
8809160 10.1021/jm9601967 Unchecked 4
8809160 10.1021/jm9601967 Beta-lactamase 3
19470510 10.1128/aac.00219-09 Unchecked 2
8809160 10.1021/jm9601967 Bacillus licheniformis 1
8809160 10.1021/jm9601967 Enterobacter cloacae 1
8809160 10.1021/jm9601967 Citrobacter freundii 1
8809160 10.1021/jm9601967 Pseudomonas aeruginosa 1
17664321 10.1128/aac.00389-07 Beta-lactamase ACC-4 1
19104021 10.1128/aac.01284-08 Efflux transporter 1
19104021 10.1128/aac.01284-08 Class C beta-lactamase CMY-36 1
19104021 10.1128/aac.01284-08 Unchecked 1

Data from ChEMBL 36 via Core Engine