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Compound Detail

CHEMBL3823101

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COc1cc(-c2cn(C)c(=O)c3cnccc23)c(OC)cc1CN(C)C

Basic Information

ChEMBL ID CHEMBL3823101
Phase Preclinical
Structure Type MOL
InChI Key BJFSUDWKXGMUKA-UHFFFAOYSA-N
16
Targets
39
Activities
3
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

353.4
MW (Da)
2.68
ALogP
6
HBA
0
HBD
56.6
PSA (Ų)
0.71
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C20H23N3O3
MW 353.42
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.32

Activity Summary

IC50 18 meas. best 7.12
Kd 18 meas. best 8.23
EC50 3 meas. best 6.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bromodomain-containing protein 9
CHEMBL3108640
Kd 8.23 7.9483 5.9 6
Bromodomain-containing protein 7
CHEMBL3085622
Kd 7.14 6.8333 73.0 6
Bromodomain-containing protein 9
CHEMBL3108640
IC50 7.12 7.12 75.0 2
Chromatin remodeling regulator CECR2
CHEMBL3108639
Kd 7.11 6.905 77.0 4
EOL1
CHEMBL614489
IC50 6.47 6.47 339.2 1
Bromodomain-containing protein 7
CHEMBL3085622
EC50 6.1 6.1 800.0 1
Bromodomain-containing protein 9
CHEMBL3108640
EC50 6.1 6.1 800.0 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 6.1 6.1 800.0 1
CREB-binding protein
CHEMBL5747
Kd 5.57 5.57 2700.0 1
Bromodomain-containing protein 7
CHEMBL3085622
IC50 5.47 5.47 3410.0 3
A204
CHEMBL614514
IC50 5.45 5.45 3550.0 1
Transcription initiation factor TFIID subunit 1
CHEMBL3217390
Kd 5.42 5.42 3800.0 1
TGF-beta receptor type-1
CHEMBL4439
IC50 5.29 5.29 5140.0 1
Activin receptor type-1
CHEMBL5903
IC50 5.29 5.29 5090.0 1
Activin receptor type-2B
CHEMBL5466
IC50 5.12 5.12 7680.0 1
Unchecked
CHEMBL612545
IC50 4.97 4.8067 10800.0 3
G-401
CHEMBL613509
IC50 4.97 4.935 10800.0 2
BT-12
CHEMBL6066736
IC50 4.76 4.76 17200.0 1
CHLA-266
CHEMBL6066737
IC50 4.47 4.47 33700.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 4.31 4.31 49000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 5301.3 ng.hr.mL-1 Mus musculus
AUC 79872.92 ng.hr.mL-1 Mus musculus
AUC 94716.56 ng.hr.mL-1 Mus musculus
CL 65.0 % Mus musculus
Cmax 5400.0 nM Mus musculus
Cmax 35000.0 nM Mus musculus
F 88.0 % Mus musculus
F 151.0 % Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bromodomain-containing protein 9 Kd = 5.9 nM 8.23 Affinity Biochemical interaction (Competition binding assay (DiscoverX)) EUB0000... -
Bromodomain-containing protein 9 Kd = 5.9 nM 8.23 Binding affinity to human BRD9 isoform 1 by BROMOScan analysis 26914985
Bromodomain-containing protein 9 Kd = 6.31 nM 8.2 Binding affinity to BRD9 (unknown origin) 32410449
Bromodomain-containing protein 9 Kd = 14.0 nM 7.85 Selectivity interaction (ITC) EUB0000004c BRD9 -
Bromodomain-containing protein 9 Kd = 14.0 nM 7.85 Binding affinity to human BRD9 expressed in Escherichia coli L21(DE3)-R3-pRARE2 ... 26914985
Bromodomain-containing protein 9 Kd = 47.0 nM 7.33 Binding affinity to recombinant human His-tagged BRD9 (134 to 239 residues) expr... 32091206
Bromodomain-containing protein 7 Kd = 73.0 nM 7.14 Binding affinity to human BRD7 by BROMOScan analysis 26914985
Bromodomain-containing protein 7 Kd = 73.0 nM 7.14 Affinity Biochemical interaction (Competition binding assay (DiscoverX)) EUB0000... -
Bromodomain-containing protein 9 IC50 = 75.0 nM 7.12 Inhibition of human N-terminal GST-tagged BRD9 isoform 1 expressed in Escherichi... 26914985
Bromodomain-containing protein 9 IC50 = 75.0 nM 7.12 Selectivity interaction (Alpha Assay) EUB0000004c BRD9 -
Chromatin remodeling regulator CECR2 Kd = 77.0 nM 7.11 Binding affinity to human CECR2 expressed in Escherichia coli L21(DE3)-R3-pRARE2... 26914985
Chromatin remodeling regulator CECR2 Kd = 77.0 nM 7.11 Selectivity interaction (BromoKdELECT (DiscoverX)) EUB0000004c CECR2 -
Bromodomain-containing protein 7 Kd = 79.43 nM 7.1 Binding affinity to BRD7 (unknown origin) 32410449
Chromatin remodeling regulator CECR2 Kd = 200.0 nM 6.7 Binding affinity to human CECR2 expressed in Escherichia coli L21(DE3)-R3-pRARE2... 26914985
Chromatin remodeling regulator CECR2 Kd = 200.0 nM 6.7 Selectivity interaction (ITC) EUB0000004c CECR2 -
Bromodomain-containing protein 7 Kd = 239.0 nM 6.62 Binding affinity to human BRD7 expressed in Escherichia coli L21(DE3)-R3-pRARE2 ... 26914985
Bromodomain-containing protein 7 Kd = 239.0 nM 6.62 Selectivity interaction (ITC) EUB0000004c BRD7 -
EOL1 IC50 = 339.2 nM 6.47 Antiproliferative activity against human EOL1 cells assessed as inhibition of ce... 30540463
Bromodomain-containing protein 7 Kd = 418.0 nM 6.38 Binding affinity to recombinant human His-tagged BRD7 (129 to 250 residues) expr... 32091206
NON-PROTEIN TARGET EC50 = 800.0 nM 6.1 Antiproliferative activity against human EOL-1 cells by cell titre glo assay 26914985

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5303304 Fibroblast 15
26914985 10.1021/acs.jmedchem.5b01865 Mus musculus 12
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
28714904 10.3390/ijms18071537 CHLA-266 11
- 10.6019/CHEMBL4689842 U2OS 10
- 10.6019/CHEMBL4689842 Fibroblast 10
28714904 10.3390/ijms18071537 BT-12 10
28714904 10.3390/ijms18071537 G-401 9
- 10.6019/CHEMBL4689842 HEK-293T 8
- 10.6019/CHEMBL5303304 HEK-293T 7
26914985 10.1021/acs.jmedchem.5b01865 Bromodomain-containing protein 7 6
26914985 10.1021/acs.jmedchem.5b01865 Bromodomain-containing protein 4 6
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
26914985 10.1021/acs.jmedchem.5b01865 Bromodomain-containing protein 9 5
- 10.6019/CHEMBL5212743 Chromatin remodeling regulator CECR2 4
26914985 10.1021/acs.jmedchem.5b01865 NON-PROTEIN TARGET 4
26914985 10.1021/acs.jmedchem.5b01865 Chromatin remodeling regulator CECR2 4
- 10.6019/CHEMBL5303304 U2OS 4

Data from ChEMBL 36 via Core Engine