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Compound Detail

CHEMBL254370

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CC[C@@H](Nc1c(Nc2cccc(C(=O)N(C)C)c2O)c(=O)c1=O)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL254370
Phase Preclinical
Structure Type MOL
InChI Key ILEJORXRDPNPIM-OAHLLOKOSA-N
3
Targets
11
Activities
2
Assay Types
5
PK Parameters
14
Publications
0
Known Names

Molecular Properties

393.4
MW (Da)
3.00
ALogP
6
HBA
3
HBD
98.7
PSA (Ų)
0.42
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H23N3O4
MW 393.44
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.82

Activity Summary

IC50 6 meas. best 8.17
Ki 5 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-X-C chemokine receptor type 2
CHEMBL2434
 Ki 8.4 8.3633 4.0 3
C-X-C chemokine receptor type 2
CHEMBL2434
 IC50 8.17 7.8867 6.8 3
C-X-C chemokine receptor type 1
CHEMBL4029
 IC50 8.17 7.38 6.8 2
C-X-C chemokine receptor type 1
CHEMBL4029
 Ki 7.4 7.4 40.0 2
Interleukin-8 receptors, CXCR1/CXCR2
CHEMBL2096909
 IC50 6.4 6.4 398.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6845.86 ng.hr.mL-1 Rattus norvegicus
AUC 6845.86 ng.hr.mL-1 Rattus norvegicus
AUC 6845.86 ng.hr.mL-1 Rattus norvegicus
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 65.0 uL.min-1.(10^6cells)-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-X-C chemokine receptor type 2 Ki = 4.0 nM 8.4 Binding affinity to CXCR2 19196511
C-X-C chemokine receptor type 2 Ki = 4.4 nM 8.36 Displacement of human [125I]IL-8 from human CXCR2 19525110
C-X-C chemokine receptor type 2 Ki = 4.7 nM 8.33 Displacement of [125I]IL8 from human CXCR2 by SPA assay 18304809
C-X-C chemokine receptor type 2 IC50 = 6.8 nM 8.17 Displacement of [125I]hCXCL8 from human CXCR2 receptor expressed in BaF3 cells 17181143
C-X-C chemokine receptor type 2 IC50 = 6.8 nM 8.17 Displacement of [125I]IL8 from human CXCR2 by SPA assay 18304809
C-X-C chemokine receptor type 1 IC50 = 6.8 nM 8.17 Inhibition of human CXCR1 33035923
C-X-C chemokine receptor type 1 Ki = 40.0 nM 7.4 Binding affinity to CXCR1 19196511
C-X-C chemokine receptor type 1 Ki = 40.0 nM 7.4 Displacement of human [125I]IL-8 from human CXCR1 19525110
C-X-C chemokine receptor type 2 IC50 = 48.0 nM 7.32 Inhibition of CXCL1-induced human neutrophil chemotaxis 17181143
C-X-C chemokine receptor type 1 IC50 = 254.0 nM 6.59 Displacement of [125I]hCXCL8 from human CXCR1 receptor expressed in BaF3 cells 17181143
Interleukin-8 receptors, CXCR1/CXCR2 IC50 = 398.0 nM 6.4 Inhibition of CXCL8-induced human neutrophil chemotaxis 17181143

Literature References

PubMed DOI Target Context # Activities
17181143 10.1021/jm0609622 C-X-C chemokine receptor type 2 2
18304809 10.1016/j.bmcl.2008.02.010 C-X-C chemokine receptor type 2 2
- 10.6019/CHEMBL3301361 ADMET 2
- 10.6019/CHEMBL3301361 No relevant target 2
17181143 10.1021/jm0609622 C-X-C chemokine receptor type 1 1
17181143 10.1021/jm0609622 Rattus norvegicus 1
17181143 10.1021/jm0609622 Interleukin-8 receptors, CXCR1/CXCR2 1
19196511 10.1016/j.bmcl.2009.01.033 C-X-C chemokine receptor type 2 1
19196511 10.1016/j.bmcl.2009.01.033 Rattus norvegicus 1
19196511 10.1016/j.bmcl.2009.01.033 C-X-C chemokine receptor type 1 1
19525110 10.1016/j.bmcl.2009.05.049 C-X-C chemokine receptor type 1 1
19525110 10.1016/j.bmcl.2009.05.049 C-X-C chemokine receptor type 2 1
19525110 10.1016/j.bmcl.2009.05.049 Rattus norvegicus 1
33035923 10.1016/j.ejmech.2020.112872 C-X-C chemokine receptor type 1 1

Data from ChEMBL 36 via Core Engine