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Compound Detail

CHEMBL4545044

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CCn1cnc2c(-c3ccc(F)c(-c4cc5c(cc4OC)C(=O)N(C)C5)c3)cnnc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4545044
Phase Preclinical
Structure Type MOL
InChI Key XPSAGIQSESMIJK-UHFFFAOYSA-N
9
Targets
12
Activities
2
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

417.4
MW (Da)
3.91
ALogP
6
HBA
0
HBD
73.1
PSA (Ų)
0.50
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H20FN5O2
MW 417.44
Aromatic Rings 4
Heavy Atoms 31
NP-Likeness -0.63

Activity Summary

IC50 6 meas. best 5.18
Ki 6 meas. best 9.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.3 8.5533 0.5 3
GABA-A receptor; alpha-1/beta-3/gamma-2
CHEMBL2094121
 Ki 9.19 9.19 0.6 1
GABA-A receptor; alpha-3/beta-3/gamma-2
CHEMBL2094120
 Ki 8.6 8.6 2.5 1
Gamma-aminobutyric acid receptor subunit alpha-5/beta-2/gamma-2
CHEMBL4523641
 Ki 7.48 7.48 33.0 1
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 5.18 5.18 6600.0 1
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 5.06 5.06 8700.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.84 4.84 14500.0 1
Cytochrome P450 2C8
CHEMBL3721
 IC50 4.82 4.82 15200.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.64 4.64 22800.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 14.0 mL.min-1.g-1 Homo sapiens
CL 14.0 mL.min-1.g-1 Rattus norvegicus
CL 27.0 mL.min-1.g-1 Canis lupus familiaris
CL 2.2 mL.min-1.kg-1 Rattus norvegicus
CL 33.0 mL.min-1.kg-1 Canis lupus familiaris
F 76.0 % Rattus norvegicus
F 43.0 % Canis lupus familiaris
Fu 0.79 - Homo sapiens
Fu 0.028 - Rattus norvegicus
Fu 0.18 - Canis lupus familiaris
T1/2 4.0 hr Rattus norvegicus
T1/2 0.75 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.5 nM 9.3 Displacement of [3H]-flumazenil from rat GABAA alpha1beta3gamma2 receptor expres... 30964988
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 0.64 nM 9.19 Displacement of [3H]-flumazenil from human GABAA alpha1beta3gamma2 receptor expr... 30964988
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 2.5 nM 8.6 Displacement of [3H]-flumazenil from human GABAA alpha3beta3gamma2 receptor expr... 30964988
Unchecked Ki = 6.6 nM 8.18 Displacement of [3H]Ro-15-1788 from human GABA alpha2/beta2/gamma2 receptor expr... 30964988
Unchecked Ki = 6.6 nM 8.18 Displacement of [3H]-flumazenil from human GABAA alpha2beta2gamma2 receptor expr... 30964988
Gamma-aminobutyric acid receptor subunit alpha-5/beta-2/gamma-2 Ki = 33.0 nM 7.48 Displacement of [3H]-flumazenil from human GABAA alpha5beta2gamma2 receptor expr... 30964988
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 6600.0 nM 5.18 Inhibition of recombinant human PDE4D2 using [3H]cAMP as substrate measured afte... 30964988
Tyrosine-protein kinase ABL1 IC50 = 8700.0 nM 5.06 Inhibition of recombinant human ABL using Ulight-TK peptide as substrate measure... 30964988
Cytochrome P450 2C9 IC50 = 14500.0 nM 4.84 Inhibition of CYP2C9 (unknown origin) 30964988
Cytochrome P450 2C8 IC50 = 15200.0 nM 4.82 Inhibition of CYP2C8 (unknown origin) 30964988
Cytochrome P450 2C19 IC50 = 22800.0 nM 4.64 Inhibition of CYP2C19 (unknown origin) 30964988

Literature References

PubMed DOI Target Context # Activities
30964988 10.1021/acs.jmedchem.9b00322 ADMET 25
30964988 10.1021/acs.jmedchem.9b00322 Unchecked 10
30964988 10.1021/acs.jmedchem.9b00322 Rattus norvegicus 9
30964988 10.1021/acs.jmedchem.9b00322 GABA-A receptor; alpha-3/beta-3/gamma-2 3
30964988 10.1021/acs.jmedchem.9b00322 GABA-A receptor; alpha-1/beta-3/gamma-2 2
30964988 10.1021/acs.jmedchem.9b00322 No relevant target 2
30964988 10.1021/acs.jmedchem.9b00322 ATP-dependent translocase ABCB1 2
30964988 10.1021/acs.jmedchem.9b00322 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
30964988 10.1021/acs.jmedchem.9b00322 Sodium channel protein type 5 subunit alpha 1
30964988 10.1021/acs.jmedchem.9b00322 Mus musculus 1
30964988 10.1021/acs.jmedchem.9b00322 Cytochrome P450 3A4 1
30964988 10.1021/acs.jmedchem.9b00322 Cytochrome P450 2D6 1
30964988 10.1021/acs.jmedchem.9b00322 Cytochrome P450 2C19 1
30964988 10.1021/acs.jmedchem.9b00322 Cytochrome P450 2C9 1
30964988 10.1021/acs.jmedchem.9b00322 Cytochrome P450 2C8 1
30964988 10.1021/acs.jmedchem.9b00322 Cytochrome P450 2B6 1
30964988 10.1021/acs.jmedchem.9b00322 Cytochrome P450 1A2 1
30964988 10.1021/acs.jmedchem.9b00322 Solute carrier family 22 member 2 1
30964988 10.1021/acs.jmedchem.9b00322 Organic anion transporter 3 1
30964988 10.1021/acs.jmedchem.9b00322 Solute carrier family 22 member 6 1

Data from ChEMBL 36 via Core Engine