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Compound Detail

CHEMBL2172374

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O=C(O)[C@H]1CC[C@H](c2cc3cccnc3c(-c3cccc(F)c3)n2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2172374
Phase Preclinical
Structure Type MOL
InChI Key XWVBOPKUSVZZPJ-HDJSIYSDSA-N
5
Targets
11
Activities
2
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

350.4
MW (Da)
4.79
ALogP
3
HBA
1
HBD
63.1
PSA (Ų)
0.74
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H19FN2O2
MW 350.39
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -1.03

Activity Summary

IC50 10 meas. best 7.5
EC50 1 meas. best 6.9

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 7.5 7.4633 32.0 3
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 7.47 7.47 34.0 3
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 6.91 6.91 123.0 3
Phosphodiesterase 4
CHEMBL2093863
 IC50 6.9 6.9 126.0 1
Unchecked
CHEMBL612545
 EC50 6.9 6.9 126.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 20788.64 ng.hr.mL-1 Mustela putorius furo
AUC 25746.66 ng.hr.mL-1 Rattus norvegicus
CL 0.64 mL.min-1.kg-1 Rattus norvegicus
Cmax 12300.0 nM Mustela putorius furo
Cmax 4600.0 nM Rattus norvegicus
F 51.5 % Rattus norvegicus
T1/2 3.2 hr Mustela putorius furo
T1/2 8.7 hr Rattus norvegicus
Tmax 1.5 hr Mustela putorius furo
Tmax 3.333 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 32.0 nM 7.5 Inhibition of human PDE4D-mediated [3H]CAMP hydrolysis after 30 to 60 mins by sc... 22889281
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 32.0 nM 7.5 Inhibition of human PDE4D 26288344
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 34.0 nM 7.47 Inhibition of human PDE4B-mediated [3H]CAMP hydrolysis after 30 to 60 mins by sc... 22889281
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 34.0 nM 7.47 Inhibition of PDE4B (unknown origin) 26288344
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 34.0 nM 7.47 Inhibition of human recombinant PDE4B 33569941
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 41.0 nM 7.39 Inhibition of human recombinant PDE4D 33569941
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 123.0 nM 6.91 Inhibition of human PDE4A-mediated [3H]CAMP hydrolysis after 30 to 60 mins by sc... 22889281
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 123.0 nM 6.91 Inhibition of PDE4A (unknown origin) 26288344
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 123.0 nM 6.91 Inhibition of human recombinant PDE4A 33569941
Unchecked EC50 = 126.0 nM 6.9 Anti-inflammatory activity against human PBMCs assessed as reduction in LPS-indu... 33569941
Phosphodiesterase 4 IC50 = 126.0 nM 6.9 Inhibition of PDE4 in human PBMC assessed as inhibition of LPS-induced TNFalpha ... 22889281

Literature References

PubMed DOI Target Context # Activities
26288344 10.1021/acs.jmedchem.5b00902 Rattus norvegicus 7
22889281 10.1021/jm300459a Mustela putorius furo 5
26288344 10.1021/acs.jmedchem.5b00902 No relevant target 2
22889281 10.1021/jm300459a Rattus norvegicus 2
22889281 10.1021/jm300459a No relevant target 1
22889281 10.1021/jm300459a Phosphodiesterase 4 1
22889281 10.1021/jm300459a 3',5'-cyclic-AMP phosphodiesterase 4D 1
22889281 10.1021/jm300459a 3',5'-cyclic-AMP phosphodiesterase 4B 1
22889281 10.1021/jm300459a 3',5'-cyclic-AMP phosphodiesterase 4A 1
22889281 10.1021/jm300459a ADMET 1
22889281 10.1021/jm300459a Mus musculus 1
26288344 10.1021/acs.jmedchem.5b00902 3',5'-cyclic-AMP phosphodiesterase 4D 1
26288344 10.1021/acs.jmedchem.5b00902 3',5'-cyclic-AMP phosphodiesterase 4B 1
26288344 10.1021/acs.jmedchem.5b00902 3',5'-cyclic-AMP phosphodiesterase 4A 1
33569941 10.1021/acs.jmedchem.0c01901 3',5'-cyclic-AMP phosphodiesterase 4D 1
33569941 10.1021/acs.jmedchem.0c01901 3',5'-cyclic-AMP phosphodiesterase 4A 1
33569941 10.1021/acs.jmedchem.0c01901 3',5'-cyclic-AMP phosphodiesterase 4B 1
33569941 10.1021/acs.jmedchem.0c01901 Unchecked 1
33569941 10.1021/acs.jmedchem.0c01901 Mus musculus 1
33569941 10.1021/acs.jmedchem.0c01901 Rattus norvegicus 1

Data from ChEMBL 36 via Core Engine