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Compound Detail

CHEMBL1230001

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O=C(O)c1ccccc1NC(=O)N1CCC(c2ccccc2C(F)(F)F)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1230001
Phase Preclinical
Structure Type MOL
InChI Key MEAQCLPMSVEOQF-UHFFFAOYSA-N
5
Targets
12
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

392.4
MW (Da)
4.82
ALogP
2
HBA
2
HBD
69.6
PSA (Ų)
0.79
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 C20H19F3N2O3
MW 392.38
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -1.22

Activity Summary

IC50 10 meas. best 9.81
EC50 2 meas. best 6.01

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Retinol-binding protein 4
CHEMBL3100
 IC50 9.81 7.87 0.2 7
Unchecked
CHEMBL612545
 IC50 6.91 6.91 122.0 1
Mus musculus
CHEMBL375
 EC50 6.01 5.985 980.0 2
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.28 4.28 52000.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 10700.0 ng.hr.mL-1 Rattus norvegicus
AUC 17200.0 ng.hr.mL-1 Mus musculus
CL 0.08333 mL.min-1.kg-1 Rattus norvegicus
Cmax 7518.22 nM Mus musculus
MRT 5.4 hr Mus musculus
MRT 9.7 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Retinol-binding protein 4 IC50 = 0.155 nM 9.81 Antagonist activity at maltose binding protein-tagged RBP4 (unknown origin) expr... 25210858
Retinol-binding protein 4 IC50 = 14.0 nM 7.85 Inhibition of human recombinant RBP4-transthyretin interaction by FRET analysis 24835984
Retinol-binding protein 4 IC50 = 14.8 nM 7.83 Displacement of [3H]retinol from biotinylated human RBP4 by scintillation proxim... 25210858
Retinol-binding protein 4 IC50 = 15.0 nM 7.82 Displacement of [3H]-retinol from RBP4 (unknown origin) by scintillation proximi... 26181715
Retinol-binding protein 4 IC50 = 15.0 nM 7.82 Competitive displacement of 3[H]retinol from biotinylated RBP4 (unknown origin) ... 31079449
Retinol-binding protein 4 IC50 = 89.0 nM 7.05 Displacement of [3H]-retinol from human recombinant RBP4 by scintillation proxim... 24835984
Retinol-binding protein 4 IC50 = 122.0 nM 6.91 Inhibition of retinol-induced interaction of bacterially expressed MBP-tagged RB... 26181715
Unchecked IC50 = 122.0 nM 6.91 Antagonist activity at retinol-induced MBP-tagged RBP4 (unknown origin) expresse... 31079449
Mus musculus EC50 = 980.0 nM 6.01 Reduction in RBP4 level in chow-fed B6D2F1 mouse after 4 hrs 24835984
Mus musculus EC50 = 1100.0 nM 5.96 Reduction in retinol level in chow-fed B6D2F1 mouse after 4 hrs 24835984
Cytochrome P450 2C19 IC50 = 52000.0 nM 4.28 Inhibition of CYP2C19 (unknown origin) 25210858
Cytochrome P450 2D6 IC50 = 100000.0 nM 4.0 Inhibition of CYP2D6 (unknown origin) 25210858

Literature References

PubMed DOI Target Context # Activities
24835984 10.1016/j.bmcl.2014.04.089 Mus musculus 7
24835984 10.1016/j.bmcl.2014.04.089 Rattus norvegicus 4
24835984 10.1016/j.bmcl.2014.04.089 Liver microsome 3
31079449 10.1021/acs.jmedchem.9b00352 ADMET 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
24835984 10.1016/j.bmcl.2014.04.089 Retinol-binding protein 4 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
26181715 10.1021/acs.jmedchem.5b00423 Retinol-binding protein 4 2
26181715 10.1021/acs.jmedchem.5b00423 Liver microsome 2
25210858 10.1021/jm5010013 Liver microsome 2
25210858 10.1021/jm5010013 Retinol-binding protein 4 2
25210858 10.1021/jm5010013 Cytochrome P450 2D6 1
25210858 10.1021/jm5010013 Cytochrome P450 3A4 1
25210858 10.1021/jm5010013 Cytochrome P450 2C19 1
25210858 10.1021/jm5010013 Cytochrome P450 2C9 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
31079449 10.1021/acs.jmedchem.9b00352 Retinol-binding protein 4 1
31079449 10.1021/acs.jmedchem.9b00352 Unchecked 1
31079449 10.1021/acs.jmedchem.9b00352 No relevant target 1
25210858 10.1021/jm5010013 No relevant target 1

Data from ChEMBL 36 via Core Engine