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Compound Detail

CHEMBL3605564

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CC(=O)OC[C@]12CC[C@H]3[C@@H](CC=C4CC=CC(=O)[C@@]43C)[C@]1(O)CC[C@@]2(O)[C@@](C)(O)[C@H]1CC(C)=C(C)C(=O)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3605564
Phase Preclinical
Structure Type MOL
InChI Key RGHQRULWHKEQHE-GRVQADPTSA-N
10
Targets
16
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

528.6
MW (Da)
3.09
ALogP
8
HBA
3
HBD
130.4
PSA (Ų)
0.37
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C30H40O8
MW 528.64
Aromatic Rings 0
Heavy Atoms 38
NP-Likeness 3.29

Activity Summary

IC50 13 meas. best 7.75
EC50 3 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bromodomain-containing protein 3
CHEMBL1795186
 IC50 7.75 6.275 18.0 2
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 7.71 6.56 19.3 2
LNCaP
CHEMBL612518
 IC50 7.16 7.16 70.0 1
Unchecked
CHEMBL612545
 EC50 7.16 7.16 70.0 1
PC-3
CHEMBL390
 EC50 6.89 6.89 130.0 1
PC-3
CHEMBL390
 IC50 6.89 6.89 130.0 1
LNCaP
CHEMBL612518
 EC50 6.89 6.89 130.0 1
ACHN
CHEMBL614519
 IC50 6.25 6.25 564.0 1
Androgen receptor
CHEMBL1871
 IC50 6.24 6.1567 580.0 3
NCI-H460
CHEMBL396
 IC50 5.92 5.92 1200.0 1
MCF7
CHEMBL387
 IC50 5.72 5.72 1900.0 1
SF-268
CHEMBL613977
 IC50 5.47 5.47 3400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bromodomain-containing protein 3 IC50 = 18.0 nM 7.75 Inhibition of BRD3-BD1 (unknown origin) by fluorescence polarization assay 36577036
Bromodomain-containing protein 4 IC50 = 19.3 nM 7.71 Inhibition of BRD4-BD1 (unknown origin) by fluorescence polarization assay 36577036
Unchecked EC50 = 70.0 nM 7.16 Antiproliferative activity against human Androgen-resistant 22Rv1 cells assessed... 36577036
LNCaP IC50 = 70.0 nM 7.16 Cytotoxicity against human LNCAP cells assessed as inhibition of cell proliferat... 26305181
LNCaP EC50 = 130.0 nM 6.89 Antiproliferative activity against androgen-sensitive human LNCaP cells assessed... 36577036
PC-3 EC50 = 130.0 nM 6.89 Antiproliferative activity against androgen-insensitive human PC-3 cells assesse... 36577036
PC-3 IC50 = 130.0 nM 6.89 Cytotoxicity against human PC3 cells assessed as inhibition of cell proliferatio... 26305181
ACHN IC50 = 564.0 nM 6.25 Sensitization of TRAIL-induced apoptosis in human ACHN cells assessed as reducti... 28257574
Androgen receptor IC50 = 580.0 nM 6.24 Inhibition of androgen receptor in human LNCAP cells assessed as inhibition of D... 26305181
Androgen receptor IC50 = 750.0 nM 6.12 Inhibition of androgen receptor in human LNCAP cells assessed as inhibition of D... 26305181
Androgen receptor IC50 = 770.0 nM 6.11 Inhibition of androgen receptor in human LNCAP cells assessed as inhibition of D... 26305181
NCI-H460 IC50 = 1200.0 nM 5.92 Cytotoxicity against human NCI-H460 cells assessed as inhibition of cell prolife... 26305181
MCF7 IC50 = 1900.0 nM 5.72 Cytotoxicity against human MCF7 cells assessed as inhibition of cell proliferati... 26305181
SF-268 IC50 = 3400.0 nM 5.47 Cytotoxicity against human SF268 cells assessed as inhibition of cell proliferat... 26305181
Bromodomain-containing protein 4 IC50 = 3917.0 nM 5.41 Inhibition of BRD4-BD2 (unknown origin) by fluorescence polarization assay 36577036
Bromodomain-containing protein 3 IC50 = 15820.0 nM 4.8 Inhibition of BRD3-BD2 (unknown origin) by fluorescence polarization assay 36577036

Literature References

PubMed DOI Target Context # Activities
36577036 10.1021/acs.jmedchem.2c01770 Unchecked 5
26305181 10.1021/acs.jmedchem.5b00867 Androgen receptor 4
26305181 10.1021/acs.jmedchem.5b00867 PC-3 2
36577036 10.1021/acs.jmedchem.2c01770 Bromodomain-containing protein 3 2
36577036 10.1021/acs.jmedchem.2c01770 Bromodomain-containing protein 4 2
26305181 10.1021/acs.jmedchem.5b00867 LNCaP 1
26305181 10.1021/acs.jmedchem.5b00867 MCF7 1
26305181 10.1021/acs.jmedchem.5b00867 NCI-H460 1
26305181 10.1021/acs.jmedchem.5b00867 SF-268 1
26305181 10.1021/acs.jmedchem.5b00867 HFF 1
26305181 10.1021/acs.jmedchem.5b00867 Mus musculus 1
28257574 10.1021/acs.jmedchem.7b00069 ACHN 1
36577036 10.1021/acs.jmedchem.2c01770 LNCaP 1
36577036 10.1021/acs.jmedchem.2c01770 PC-3 1
36577036 10.1021/acs.jmedchem.2c01770 HFF 1

Data from ChEMBL 36 via Core Engine