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Compound Detail

CHEMBL3774655

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CCC(=O)N1CCOc2c(cc(-c3ccc(OC)c(OC)c3)cc2OC[C@H]2CCCN(C)C2)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3774655
Phase Preclinical
Structure Type MOL
InChI Key YKNAKDFZAWQEEO-IBGZPJMESA-N
4
Targets
25
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

468.6
MW (Da)
4.22
ALogP
6
HBA
0
HBD
60.5
PSA (Ų)
0.61
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C27H36N2O5
MW 468.59
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness -0.78

Activity Summary

Kd 15 meas. best 6.82
IC50 10 meas. best 6.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CREB-binding protein/Histone acetyltransferase p300
CHEMBL3883300
 Kd 6.82 6.82 151.0 1
CREB-binding protein
CHEMBL5747
 Kd 6.82 6.8117 151.0 6
Histone acetyltransferase p300
CHEMBL3784
 Kd 6.78 6.635 167.0 4
CREB-binding protein
CHEMBL5747
 IC50 6.77 6.495 170.0 6
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 6.22 5.3675 600.0 4
Bromodomain-containing protein 4
CHEMBL1163125
 Kd 5.25 5.25 5590.0 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CREB-binding protein Kd = 151.0 nM 6.82 Binding affinity to CBP (unknown origin) assessed as dissociation constant by IT... 38477974
CREB-binding protein Kd = 151.0 nM 6.82 Affinity Biochemical interaction (ITC) EUB0000195c CREBBP -
CREB-binding protein Kd = 151.0 nM 6.82 Binding affinity to C-terminally biotinylated N-terminal His10-tagged human CBP ... 29170712
CREB-binding protein/Histone acetyltransferase p300 Kd = 151.0 nM 6.82 Binding affinity to human CBP/P300 expressed in Escherichia coli BL21(DE3)-R3 by... 27673482
CREB-binding protein Kd = 151.0 nM 6.82 Binding affinity to CBP (unknown origin) by isothermal titration calorimetric an... 26572217
CREB-binding protein Kd = 151.0 nM 6.82 Inhibition of human CREBBP expressed in competent escherichia coli BL21(DE3)-R3-... 26701186
Histone acetyltransferase p300 Kd = 167.0 nM 6.78 Binding affinity to p300 (unknown origin) assessed as dissociation constant by I... 38477974
Histone acetyltransferase p300 Kd = 167.0 nM 6.78 Binding affinity to EP300 (unknown origin) by isothermal titration calorimetry 29170712
Histone acetyltransferase p300 Kd = 167.0 nM 6.78 Inhibition of human p300 expressed in competent escherichia coli BL21(DE3)-R3-pR... 26701186
CREB-binding protein IC50 = 170.0 nM 6.77 Selectivity interaction (AlphaScreen) EUB0000195c CREBBP -
CREB-binding protein Kd = 170.0 nM 6.77 Selectivity interaction (Biolayer Interferometry experiment) EUB0000195c CREBBP -
CREB-binding protein IC50 = 170.0 nM 6.77 Inhibition of CBP (unknown origin) by alphascreen assay 26572217
CREB-binding protein IC50 = 323.6 nM 6.49 Alphascreen assay. Binding to CREBBPA (domain start/stop: R1081-G1197) by alphas... 26552700
CREB-binding protein IC50 = 440.0 nM 6.36 Inhibition of His tagged recombinant CBP (unknown origin) by TR-FRET assay 29155580
CREB-binding protein IC50 = 440.0 nM 6.36 Displacement of biotinylated ligand from CBP (unknown origin) by TR-FRET assay 27682507
CREB-binding protein IC50 = 600.0 nM 6.22 Affinity On-target Cellular interaction (NanoBRET assay (HEK293T cells)) EUB0000... -
Bromodomain-containing protein 4 IC50 = 600.0 nM 6.22 Displacement of Halo-tagged histone H3.3 from Nluc-BRD4 (unknown origin) express... 29170712
Histone acetyltransferase p300 Kd = 625.0 nM 6.2 Affinity Biochemical interaction (ITC) EUB0000195c EP300 -
Bromodomain-containing protein 4 IC50 = 2456.1 nM 5.61 Alphascreen assay. Binding to BRD4A (domain start/stop: N44-E168) by alphascreen... 26552700
Bromodomain-containing protein 4 Kd = 5590.0 nM 5.25 Binding affinity to human BRD4 bromodomain1 by isothermal titration calorimetry 29170712

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 Fibroblast 10
- 10.6019/CHEMBL4689842 HEK-293T 9
- 10.6019/CHEMBL4689842 U2OS 8
26552700 10.1158/0008-5472.CAN-15-0236 Protein polybromo-1 7
31476112 10.15252/emmm.201809930 Histone acetyltransferase p300 5
26552700 10.1158/0008-5472.CAN-15-0236 Bromodomain-containing protein 4 5
26552700 10.1158/0008-5472.CAN-15-0236 CREB-binding protein 4
26552700 10.1158/0008-5472.CAN-15-0236 Bromodomain-containing protein 3 4
- 10.6019/CHEMBL5212743 Bromodomain-containing protein 4 4
26552700 10.1158/0008-5472.CAN-15-0236 PH-interacting protein 3
26552700 10.1158/0008-5472.CAN-15-0236 Bromodomain-containing protein 2 3
- 10.6019/CHEMBL5212743 CREB-binding protein 3
29170712 10.1039/C6MD00373G Bromodomain-containing protein 4 2
26552700 10.1158/0008-5472.CAN-15-0236 Bromodomain testis-specific protein 2
26552700 10.1158/0008-5472.CAN-15-0236 Transcription initiation factor TFIID subunit 1 2
26552700 10.1158/0008-5472.CAN-15-0236 Transcription intermediary factor 1-alpha 2
27682507 10.1021/acs.jmedchem.6b01022 CREB-binding protein 2
26552700 10.1158/0008-5472.CAN-15-0236 Bromodomain adjacent to zinc finger domain protein 2B 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
26552700 10.1158/0008-5472.CAN-15-0236 Histone acetyltransferase KAT2B 2

Data from ChEMBL 36 via Core Engine