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Compound Detail

CHEMBL2204469

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Cc1c(Cc2ccc(=O)n(Cc3ccc(F)cc3F)n2)c2cc(F)ccc2n1CC(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2204469
Phase Preclinical
Structure Type MOL
InChI Key ZTPOWDSDKMQVBU-UHFFFAOYSA-N
12
Targets
16
Activities
1
Assay Types
25
PK Parameters
20
Publications
0
Known Names

Molecular Properties

441.4
MW (Da)
3.65
ALogP
5
HBA
1
HBD
77.1
PSA (Ų)
0.50
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H18F3N3O3
MW 441.41
Aromatic Rings 4
Heavy Atoms 32
NP-Likeness -1.48

Activity Summary

IC50 16 meas. best 9.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin D2 receptor 2
CHEMBL5071
 IC50 9.1 8.81 0.8 4
Eosinophil
CHEMBL614636
 IC50 8.52 8.52 3.0 1
Prostaglandin D2 receptor 2
CHEMBL2291
 IC50 8.15 8.15 7.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.8 4.8 16000.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.8 4.8 16000.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.8 4.8 16000.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.8 4.8 16000.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.8 4.8 16000.0 1
Cytochrome P450 2C8
CHEMBL3721
 IC50 4.8 4.8 16000.0 1
Cytochrome P450 2B6
CHEMBL4729
 IC50 4.8 4.8 16000.0 1
Cytochrome P450 2A6
CHEMBL5282
 IC50 4.8 4.8 16000.0 1
Prostaglandin D2 receptor
CHEMBL4427
 IC50 4.72 4.72 19000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 5066.0 hr.kg.ng/ml/mg Rattus norvegicus
AUC 1154.0 ng.hr.kg/ml/mg Macaca mulatta
AUC 678.0 ng.hr.kg/ml/mg Canis lupus familiaris
AUC 5066.0 ng.hr.kg/ml/mg Rattus norvegicus
CL 12.0 mL.min-1.kg-1 Rattus norvegicus
CL 1000.0 mL.min-1.g-1 Homo sapiens
CL 3.8 mL.min-1.kg-1 Rattus norvegicus
CL 2600.0 mL.min-1.g-1 Rattus norvegicus
CL 14.0 mL.min-1.kg-1 Rattus norvegicus
CL 21.0 mL.min-1.kg-1 Macaca mulatta
CL 20.0 mL.min-1.kg-1 Canis lupus familiaris
CL 12.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 1748.94 nM Rattus norvegicus
Cmax 557.3 nM Macaca mulatta
Cmax 1622.07 nM Canis lupus familiaris
Cmax 1748.94 nM Rattus norvegicus
F 37.0 % Rattus norvegicus
F 12.0 % Macaca mulatta
F 8.0 % Canis lupus familiaris
F 37.0 % Rattus norvegicus
Fu 0.02 - Homo sapiens
T1/2 3.0 hr Rattus norvegicus
T1/2 2.3 hr Macaca mulatta
T1/2 2.3 hr Canis lupus familiaris
T1/2 3.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin D2 receptor 2 IC50 = 0.8 nM 9.1 Binding affinity to human CRTH2 receptor 22651823
Prostaglandin D2 receptor 2 IC50 = 1.2 nM 8.92 Inhibition of CRTH2 receptor-mediated chemotaxis in human basophils 22651823
Prostaglandin D2 receptor 2 IC50 = 2.0 nM 8.7 Antagonist activity at human recombinant CRTh2 expressed in CHO-K1 cells by cAMP... 24512187
Eosinophil IC50 = 3.0 nM 8.52 Inhibition of eosinophil shape change in human whole blood after 10 mins by flow... 22651823
Prostaglandin D2 receptor 2 IC50 = 3.0 nM 8.52 Displacement of [3H]PGD2 from recombinant human CRTH2 receptor expressed in CHO-... 22651823
Prostaglandin D2 receptor 2 IC50 = 7.0 nM 8.15 Inhibition of mouse CRTH2 receptor 22651823
Cytochrome P450 2A6 IC50 = 16000.0 nM 4.8 Inhibition of CYP2A6 22651823
Cytochrome P450 1A2 IC50 = 16000.0 nM 4.8 Inhibition of CYP1A2 22651823
Cytochrome P450 2B6 IC50 = 16000.0 nM 4.8 Inhibition of CYP2B6 22651823
Cytochrome P450 2C8 IC50 = 16000.0 nM 4.8 Inhibition of CYP2C8 22651823
Cytochrome P450 2C19 IC50 = 16000.0 nM 4.8 Inhibition of CYP2C19 22651823
Cytochrome P450 2C9 IC50 = 16000.0 nM 4.8 Inhibition of CYP2C9 22651823
Cytochrome P450 2D6 IC50 = 16000.0 nM 4.8 Inhibition of CYP2D6 22651823
Cytochrome P450 3A4 IC50 = 16000.0 nM 4.8 Inhibition of CYP3A4 22651823
Prostaglandin D2 receptor IC50 = 19000.0 nM 4.72 Binding affinity to DP1 receptor by FRET assay 22651823

Literature References

PubMed DOI Target Context # Activities
22651823 10.1021/jm300007n Mus musculus 15
22651823 10.1021/jm300007n Ovis aries 11
24512187 10.1021/jm401509e Rattus norvegicus 7
24512187 10.1021/jm401509e Canis familiaris 6
22651823 10.1021/jm300007n Rattus norvegicus 6
24512187 10.1021/jm401509e Rhesus monkey 6
22651823 10.1021/jm300007n Prostaglandin D2 receptor 2 4
24512187 10.1021/jm401509e ADMET 4
24512187 10.1021/jm401509e Hepatocyte 3
24512187 10.1021/jm401509e NON-PROTEIN TARGET 3
22651823 10.1021/jm300007n Unchecked 3
22651823 10.1021/jm300007n Plasma 2
22651823 10.1021/jm300007n Caco-2 2
22651823 10.1021/jm300007n Cytochrome P450 2B6 1
22651823 10.1021/jm300007n Cytochrome P450 2C8 1
22651823 10.1021/jm300007n Cytochrome P450 2C19 1
22651823 10.1021/jm300007n Cytochrome P450 2C9 1
22651823 10.1021/jm300007n Cytochrome P450 2A6 1
22651823 10.1021/jm300007n Cytochrome P450 3A4 1
22651823 10.1021/jm300007n Salmonella typhimurium 1

Data from ChEMBL 36 via Core Engine