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Compound Detail

CHEMBL4076748

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CC(=O)N1CCc2c(c(N3CCCc4cc(-c5cnn(C)c5)c(C(F)F)cc43)nn2C2CCOCC2)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4076748
Phase Preclinical
Structure Type MOL
InChI Key LWXLECMNBTVASW-UHFFFAOYSA-N
6
Targets
11
Activities
3
Assay Types
20
PK Parameters
20
Publications
0
Known Names

Molecular Properties

510.6
MW (Da)
4.56
ALogP
7
HBA
0
HBD
68.4
PSA (Ų)
0.51
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C27H32F2N6O2
MW 510.59
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -1.62

Activity Summary

IC50 7 meas. best 8.96
Kd 3 meas. best 8.96
EC50 1 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CREB-binding protein
CHEMBL5747
 IC50 8.96 8.44 1.1 2
CREB-binding protein
CHEMBL5747
 Kd 8.96 8.96 1.1 1
Histone acetyltransferase p300
CHEMBL3784
 IC50 8.89 8.89 1.3 1
Histone acetyltransferase p300
CHEMBL3784
 Kd 8.89 8.89 1.3 1
CREB-binding protein
CHEMBL5747
 EC50 7.85 7.85 14.0 1
Bromodomain-containing protein 4
CHEMBL1163125
 Kd 6.7 6.7 200.0 1
VCaP
CHEMBL4296508
 IC50 6.67 6.67 216.0 1
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 5.38 5.38 4200.0 1
LNCaP
CHEMBL612518
 IC50 5.16 5.16 7000.0 1
Chromatin remodeling regulator CECR2
CHEMBL3108639
 IC50 4.85 4.85 14000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6995.08 ng.hr.mL-1 Mus musculus
AUC 4799.55 ng.hr.mL-1 Rattus norvegicus
AUC 15828.29 ng.hr.mL-1 Canis lupus familiaris
AUC 4340.01 ng.hr.mL-1 Macaca fascicularis
CL 7.4 mL.min-1.kg-1 Macaca fascicularis
CL 4.6 mL.min-1.kg-1 Canis lupus familiaris
CL 16.0 mL.min-1.kg-1 Rattus norvegicus
CL 8.8 mL.min-1.kg-1 Mus musculus
Cmax 5100.0 nM Canis lupus familiaris
Cmax 1600.0 nM Macaca fascicularis
Cmax 3200.0 nM Rattus norvegicus
Cmax 4200.0 nM Mus musculus
F 39.0 % Macaca fascicularis
F 94.0 % Canis lupus familiaris
F 93.0 % Rattus norvegicus
F 72.0 % Mus musculus
T1/2 2.8 hr Macaca fascicularis
T1/2 4.2 hr Canis lupus familiaris
T1/2 0.66 hr Rattus norvegicus
T1/2 1.1 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CREB-binding protein IC50 = 1.1 nM 8.96 Displacement of biotinylated histone H3K14 peptide ligand from human recombinant... 28892380
CREB-binding protein Kd = 1.1 nM 8.96 Binding affinity to CBP (unknown origin) assessed as dissociation constant by IT... 38477974
Histone acetyltransferase p300 IC50 = 1.3 nM 8.89 Displacement of biotinylated histone H3K14 peptide ligand from human recombinant... 28892380
Histone acetyltransferase p300 Kd = 1.3 nM 8.89 Binding affinity to p300 (unknown origin) assessed as dissociation constant by I... 38477974
CREB-binding protein IC50 = 12.0 nM 7.92 Inhibition of Halo-tagged histone H3.3 binding to NanoLuc luciferase conjugated ... 28892380
CREB-binding protein EC50 = 14.0 nM 7.85 Inhibition of CBP in human MV-4-11 cells assessed as decrease in MYC expression ... 28892380
Bromodomain-containing protein 4 Kd = 200.0 nM 6.7 Binding affinity to BRD4 (unknown origin) assessed as dissociation constant by I... 38477974
VCaP IC50 = 216.0 nM 6.67 Antiproliferative activity against AR positive human VCaP cells assessed inhibit... 38530938
Bromodomain-containing protein 4 IC50 = 4200.0 nM 5.38 Displacement of biotinylated histone H3K14 peptide ligand from human recombinant... 28892380
LNCaP IC50 = 7000.0 nM 5.16 Antiproliferative activity against AR positive human LNCaP cells assessed inhibi... 38530938
Chromatin remodeling regulator CECR2 IC50 = 14000.0 nM 4.85 Displacement of biotinylated histone H3K14 peptide ligand from human recombinant... 28892380

Literature References

PubMed DOI Target Context # Activities
38530938 10.1021/acs.jmedchem.3c01789 Unchecked 9
28892380 10.1021/acs.jmedchem.7b00796 Rattus norvegicus 7
28892380 10.1021/acs.jmedchem.7b00796 Cynomolgus monkey 6
28892380 10.1021/acs.jmedchem.7b00796 Mus musculus 6
28892380 10.1021/acs.jmedchem.7b00796 Canis familiaris 6
28892380 10.1021/acs.jmedchem.7b00796 Plasma 5
28892380 10.1021/acs.jmedchem.7b00796 CREB-binding protein 3
38530938 10.1021/acs.jmedchem.3c01789 VCaP 2
- 10.6019/CHEMBL5724709 HEK-293T 2
- 10.6019/CHEMBL5724709 U2OS 2
28892380 10.1021/acs.jmedchem.7b00796 Transcription initiation factor TFIID subunit 1 2
28892380 10.1021/acs.jmedchem.7b00796 ADMET 2
- 10.6019/CHEMBL5724709 Fibroblast 2
28892380 10.1021/acs.jmedchem.7b00796 Bromodomain-containing protein 4 2
28892380 10.1021/acs.jmedchem.7b00796 Histone acetyltransferase KAT2B 1
28892380 10.1021/acs.jmedchem.7b00796 Histone acetyltransferase KAT2A 1
28892380 10.1021/acs.jmedchem.7b00796 Chromatin remodeling regulator CECR2 1
28892380 10.1021/acs.jmedchem.7b00796 Peregrin 1
28892380 10.1021/acs.jmedchem.7b00796 Bromodomain-containing protein 9 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1

Data from ChEMBL 36 via Core Engine