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Compound Detail

CHEMBL249854

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CC(=O)c1sc(NC(=O)N[C@@H]2CN(C(C)=O)CC[C@H]2CN2CCC[C@@H](Cc3ccc(F)cc3)C2)nc1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL249854
Phase Preclinical
Structure Type MOL
InChI Key ZFRLEPMXXGKKBN-WPFOTENUSA-N
9
Targets
12
Activities
2
Assay Types
10
PK Parameters
15
Publications
0
Known Names

Molecular Properties

529.7
MW (Da)
4.11
ALogP
6
HBA
2
HBD
94.6
PSA (Ų)
0.53
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H36FN5O3S
MW 529.68
Aromatic Rings 2
Heavy Atoms 37
NP-Likeness -1.63

Activity Summary

IC50 9 meas. best 10.17
Ki 3 meas. best 5.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-C chemokine receptor type 3
CHEMBL3473
 IC50 10.17 9.16 0.1 3
Probable C-C chemokine receptor type 3
CHEMBL3406
 IC50 8.44 8.295 3.6 2
D(2) dopamine receptor
CHEMBL217
 IC50 6.19 6.19 640.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.89 5.89 1300.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 IC50 5.28 5.28 5300.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.22 5.22 6000.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 5.19 5.19 6500.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 5.11 5.11 7700.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 4.54 4.54 29000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 41.67 mL.min-1.kg-1 Mus musculus
CL 14.5 mL.min-1.kg-1 Macaca fascicularis
CL 21.67 mL.min-1.kg-1 Pan troglodytes
CL 16.0 mL.min-1.kg-1 Homo sapiens
F 25.0 % Mus musculus
F 18.0 % Macaca fascicularis
F 7.0 % Pan troglodytes
T1/2 1.2 hr Mus musculus
T1/2 5.5 hr Macaca fascicularis
T1/2 4.5 hr Pan troglodytes

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-C chemokine receptor type 3 IC50 = 0.068 nM 10.17 Antagonist activity at CCR3 assessed as eotaxin-induced chemotaxis in human eosi... 17418570
C-C chemokine receptor type 3 IC50 = 1.9 nM 8.72 Displacement of [125I]eotaxin from human CCR3 expressed in CHO cells after 30 mi... 17418570
C-C chemokine receptor type 3 IC50 = 2.6 nM 8.59 Antagonist activity at CCR3 in human eosinophils assessed as eotaxin-induced cal... 17418570
Probable C-C chemokine receptor type 3 IC50 = 3.6 nM 8.44 Displacement of [125I]eotaxin from BALB/c mouse CCR3 expressed in CHO cells afte... 17418570
Probable C-C chemokine receptor type 3 IC50 = 7.0 nM 8.15 Antagonist activity at CCR3 assessed as eotaxin-induced chemotaxis in BALB/c mou... 17418570
D(2) dopamine receptor IC50 = 640.0 nM 6.19 Inhibition of dopamine D2 receptor 17418570
Cytochrome P450 2D6 IC50 = 1300.0 nM 5.89 Inhibition of human recombinant CYP2D6 17418570
5-hydroxytryptamine receptor 2A IC50 = 5300.0 nM 5.28 Inhibition of 5HT2A receptor 17418570
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 6000.0 nM 5.22 Inhibition of hERG 17418570
Sodium-dependent dopamine transporter Ki = 6500.0 nM 5.19 Binding affinity to dopamine transporter 17418570
Sodium-dependent noradrenaline transporter Ki = 7700.0 nM 5.11 Binding affinity to norepinephrine transporter 17418570
Sodium-dependent serotonin transporter Ki = 29000.0 nM 4.54 Binding affinity to serotonin transporter 17418570

Literature References

PubMed DOI Target Context # Activities
17418570 10.1016/j.bmcl.2007.03.065 Mus musculus 5
17418570 10.1016/j.bmcl.2007.03.065 C-C chemokine receptor type 3 3
17418570 10.1016/j.bmcl.2007.03.065 Cynomolgus monkey 3
17418570 10.1016/j.bmcl.2007.03.065 Pan troglodytes 3
17418570 10.1016/j.bmcl.2007.03.065 Probable C-C chemokine receptor type 3 2
17418570 10.1016/j.bmcl.2007.03.065 Sodium-dependent noradrenaline transporter 1
17418570 10.1016/j.bmcl.2007.03.065 Cytochrome P450 2D6 1
17418570 10.1016/j.bmcl.2007.03.065 5-hydroxytryptamine receptor 2A 1
17418570 10.1016/j.bmcl.2007.03.065 D(2) dopamine receptor 1
17418570 10.1016/j.bmcl.2007.03.065 Sodium-dependent serotonin transporter 1
17418570 10.1016/j.bmcl.2007.03.065 Sodium-dependent dopamine transporter 1
17418570 10.1016/j.bmcl.2007.03.065 Voltage-gated inwardly rectifying potassium channel KCNH2 1
17418570 10.1016/j.bmcl.2007.03.065 Serum 1
17418570 10.1016/j.bmcl.2007.03.065 Caco-2 1
17418570 10.1016/j.bmcl.2007.03.065 Liver microsomes 1

Data from ChEMBL 36 via Core Engine