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Compound Detail

CHEMBL260091

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C[C@@H](O)[C@H](NC(=O)c1ccc(C#Cc2ccc(CN3CCOCC3)cc2)cc1)C(=O)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL260091
Phase Preclinical
Structure Type MOL
InChI Key FQYBTYFKOHPWQT-VGSWGCGISA-N
4
Targets
20
Activities
3
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

437.5
MW (Da)
0.90
ALogP
6
HBA
4
HBD
111.1
PSA (Ų)
0.30
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C24H27N3O5
MW 437.50
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness -0.86

Activity Summary

Ki 12 meas. best 9.3
IC50 7 meas. best 8.68
Kd 1 meas. best 9.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
UDP-3-O-acyl-N-acetylglucosamine deacetylase
CHEMBL3855
 Kd 9.32 9.32 0.5 1
UDP-3-O-acyl-N-acetylglucosamine deacetylase
CHEMBL5244
 Ki 9.3 8.6429 0.5 7
Unchecked
CHEMBL612545
 Ki 9.0 8.0567 1.0 3
Unchecked
CHEMBL612545
 IC50 8.68 7.9 2.1 2
UDP-3-O-acyl-N-acetylglucosamine deacetylase
CHEMBL4296297
 Ki 8.52 8.49 3.0 2
UDP-3-O-acyl-N-acetylglucosamine deacetylase
CHEMBL5244
 IC50 8.52 7.88 3.0 4
UDP-3-O-acyl-N-acetylglucosamine deacetylase
CHEMBL3855
 IC50 6.51 6.51 310.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 15.14 uL.min-1.(10^6cells)-1 Homo sapiens
CL 38.9 uL.min-1.(10^6cells)-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
UDP-3-O-acyl-N-acetylglucosamine deacetylase Kd = 0.48 nM 9.32 Binding affinity to Pseudomonas aeruginosa PAO1 NB52019 LpxC after 60 to 420 sec... 30226381
UDP-3-O-acyl-N-acetylglucosamine deacetylase Ki = 0.5 nM 9.3 Inhibition of Escherichia coli LpxC 18025458
UDP-3-O-acyl-N-acetylglucosamine deacetylase Ki = 0.5 nM 9.3 Inhibition of Escherichia coli LpxC enzyme 23914798
Unchecked Ki = 1.0 nM 9.0 Binding affinity to Pseudomonas aeruginosa LpxC assessed as inhibition constant 33538159
Unchecked Ki = 2.0 nM 8.7 Binding affinity to Escherichia coli LpxC assessed as inhibition constant 33538159
UDP-3-O-acyl-N-acetylglucosamine deacetylase Ki = 2.0 nM 8.7 Inhibition of Escherichia coli LpxC 22401863
UDP-3-O-acyl-N-acetylglucosamine deacetylase Ki = 2.0 nM 8.7 Inhibition of Escherichia coli LpxC 21273067
Unchecked IC50 = 2.1 nM 8.68 Inhibition of Pseudomonas aeruginosa LpxC 33538159
UDP-3-O-acyl-N-acetylglucosamine deacetylase IC50 = 3.0 nM 8.52 Inhibition of Escherichia coli LpxC using UDP-3-O-(R-3-hydroxymyristoyl)GlcNAc a... 27326338
UDP-3-O-acyl-N-acetylglucosamine deacetylase Ki = 3.0 nM 8.52 Inhibition of Rhizobium leguminosarum LpxC W206Q/S214G mutant 18025458
UDP-3-O-acyl-N-acetylglucosamine deacetylase IC50 = 3.0 nM 8.52 Inhibition of Escherichia coli LpxC using UDP-3-O-(R-3-hydroxymyristoyl)GlcNAc a... 28082037
UDP-3-O-acyl-N-acetylglucosamine deacetylase Ki = 3.5 nM 8.46 Inhibition of Rhizobium leguminosarum LpxC S214G mutant 18025458
UDP-3-O-acyl-N-acetylglucosamine deacetylase Ki = 5.0 nM 8.3 Inhibition of Escherichia coli LpxC Q202W/G210S mutant 18025458
UDP-3-O-acyl-N-acetylglucosamine deacetylase Ki = 8.0 nM 8.1 Inhibition of Escherichia coli LpxC using UDP-3-O-[(R)-3-hydroxymyristoyl]-N-ace... 24412340
UDP-3-O-acyl-N-acetylglucosamine deacetylase Ki = 8.0 nM 8.1 Inhibition of Escherichia coli LpxC C63A mutant using UDP-3-O-[(R)-3-hydroxymyri... 26827141
UDP-3-O-acyl-N-acetylglucosamine deacetylase IC50 = 58.0 nM 7.24 Inhibition of Escherichia coli LpxC C63A mutant using UDP-3-O-[(R)-3-hydroxymyri... 26827141
UDP-3-O-acyl-N-acetylglucosamine deacetylase IC50 = 58.0 nM 7.24 Inhibition of Escherichia coli LpxC using UDP-3-O-[(R)-3-hydroxymyristoyl]-N-ace... 24412340
Unchecked IC50 = 76.0 nM 7.12 Inhibition of LpxC C63A mutant in Escherichia coli assessed as reduction in bact... 32386952
UDP-3-O-acyl-N-acetylglucosamine deacetylase IC50 = 310.0 nM 6.51 Inhibition of Pseudomonas aeruginosa LpxC using UDP-3-O-(R-3-hydroxydecanoyl)-N-... 25408833
Unchecked Ki = 340.0 nM 6.47 Inhibition of Rhizobium leguminosarum LpxC 18025458

Literature References

PubMed DOI Target Context # Activities
20516283 10.1128/aac.01600-09 NON-PROTEIN TARGET 23
18025458 10.1073/pnas.0709412104 UDP-3-O-acyl-N-acetylglucosamine deacetylase 18
20516283 10.1128/aac.01600-09 Burkholderia multivorans 16
20516283 10.1128/aac.01600-09 Burkholderia cenocepacia 10
34569791 10.1021/acs.jmedchem.1c00888 Pseudomonas aeruginosa 7
18025458 10.1073/pnas.0709412104 Unchecked 5
- 10.6019/CHEMBL3301361 ADMET 4
32386952 10.1016/j.bmc.2020.115529 Escherichia coli 4
26827141 10.1016/j.bmc.2016.01.029 Escherichia coli 4
23914798 10.1021/jm4007774 Escherichia coli 4
21194954 10.1016/j.bmc.2010.12.017 Escherichia coli 3
20516283 10.1128/aac.01600-09 Burkholderia cepacia 3
29233653 10.1016/j.bmcl.2017.12.005 UDP-3-O-acyl-N-acetylglucosamine deacetylase 3
33538159 10.1021/acs.jmedchem.0c02185 Unchecked 3
27326338 10.1021/acsmedchemlett.6b00057 Escherichia coli 2
20516283 10.1128/aac.01600-09 Pseudomonas aeruginosa 2
22175825 10.1021/jm2014748 Pseudomonas aeruginosa 2
25408833 10.1021/ml500210x Escherichia coli 2
25408833 10.1021/ml500210x Pseudomonas aeruginosa 2
24412340 10.1016/j.bmc.2013.12.057 UDP-3-O-acyl-N-acetylglucosamine deacetylase 2

Data from ChEMBL 36 via Core Engine