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Compound Detail

CHEMBL3605565

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CC(=O)OC[C@]12CC[C@H]3[C@@H](C[C@H]4O[C@]45CC=CC(=O)[C@]35C)[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 CHEMBL3605565
Phase Preclinical
Structure Type MOL
InChI Key GKMMNQCWGZRQTN-XVRWHRFDSA-N
14
Targets
25
Activities
3
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

544.6
MW (Da)
2.30
ALogP
9
HBA
3
HBD
142.9
PSA (Ų)
0.36
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 C30H40O9
MW 544.64
Aromatic Rings 0
Heavy Atoms 39
NP-Likeness 3.49

Activity Summary

IC50 18 meas. best 8.15
EC50 5 meas. best 7.67
Kd 2 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bromodomain-containing protein 3
CHEMBL1795186
 IC50 8.15 7.56 7.1 2
Bromodomain-containing protein 3
CHEMBL1795186
 Kd 7.85 7.34 14.1 2
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 7.75 7.3 17.9 2
LNCaP
CHEMBL612518
 IC50 7.7 7.7 20.0 2
LNCaP
CHEMBL612518
 EC50 7.67 7.67 21.6 1
CWR22R
CHEMBL612657
 IC50 7.52 7.52 30.0 1
Unchecked
CHEMBL612545
 EC50 7.52 7.52 30.3 1
VCaP
CHEMBL4296508
 EC50 7.52 7.52 30.5 1
PC-3
CHEMBL390
 EC50 7.2 7.2 63.0 1
PC-3
CHEMBL390
 IC50 7.05 7.05 90.0 1
Bromodomain-containing protein 2
CHEMBL1293289
 IC50 6.99 6.8 103.0 2
ACHN
CHEMBL614519
 IC50 6.93 6.6533 117.0 3
Bromodomain testis-specific protein
CHEMBL1795185
 IC50 6.92 6.655 119.0 2
MCF7
CHEMBL387
 IC50 6.68 6.68 210.0 1
DU-145
CHEMBL613508
 EC50 6.58 6.58 263.0 1
NCI-H460
CHEMBL396
 IC50 6.1 6.1 800.0 1
SF-268
CHEMBL613977
 IC50 5.58 5.58 2600.0 1

Pharmacokinetic Data

Parameter Value Units Species
Tmax 0.25 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bromodomain-containing protein 3 IC50 = 7.11 nM 8.15 Binding affinity to human partial length BRD3 BD1 (P24 to E144 residues) express... 36577036
Bromodomain-containing protein 3 Kd = 14.1 nM 7.85 Binding affinity to 6His-tagged BRD3-BD1 (unknown origin) by MST assay 36577036
Bromodomain-containing protein 4 IC50 = 17.9 nM 7.75 Binding affinity to human partial length BRD4 BD1 (N44 to E168 residues) express... 36577036
LNCaP IC50 = 20.0 nM 7.7 Cytotoxicity against human LNCAP cells assessed as inhibition of cell proliferat... 26305181
LNCaP IC50 = 20.0 nM 7.7 Cytotoxicity against human LNCAP cells assessed as reduction in cell viability a... 28617598
LNCaP EC50 = 21.6 nM 7.67 Antiproliferative activity against androgen-sensitive human LNCaP cells assessed... 36577036
VCaP EC50 = 30.5 nM 7.52 Antiproliferative activity against AR-positive human VCaP cells assessed as redu... 36577036
Unchecked EC50 = 30.3 nM 7.52 Antiproliferative activity against human Androgen-resistant 22Rv1 cells assessed... 36577036
CWR22R IC50 = 30.0 nM 7.52 Cytotoxicity against human 22Rv1 cells assessed as reduction in cell viability a... 28617598
PC-3 EC50 = 63.0 nM 7.2 Antiproliferative activity against androgen-insensitive human PC-3 cells assesse... 36577036
PC-3 IC50 = 90.0 nM 7.05 Cytotoxicity against human PC3 cells assessed as inhibition of cell proliferatio... 26305181
Bromodomain-containing protein 2 IC50 = 103.0 nM 6.99 Binding affinity to human partial length BRD2 BD1 (K71 to N194 residues) express... 36577036
Bromodomain-containing protein 3 IC50 = 108.0 nM 6.97 Binding affinity to human partial length BRD3 BD2 (G306 to P416 residues) expres... 36577036
ACHN IC50 = 117.0 nM 6.93 Induction of TRAIL induced apoptosis in human ACHN cells assessed as reduction i... 38278080
Bromodomain testis-specific protein IC50 = 119.0 nM 6.92 Binding affinity to human partial length BRDT BD2 (K250 to E382 residues) expres... 36577036
Bromodomain-containing protein 4 IC50 = 142.0 nM 6.85 Binding affinity to human partial length BRD4 BD2 (K333 to E460 residues) expres... 36577036
Bromodomain-containing protein 3 Kd = 149.0 nM 6.83 Binding affinity to 6His-tagged BRD3-BD2 (unknown origin) by MST assay 36577036
ACHN IC50 = 164.0 nM 6.79 Sensitization of TRAIL-induced apoptosis in human ACHN cells assessed as reducti... 28257574
MCF7 IC50 = 210.0 nM 6.68 Cytotoxicity against human MCF7 cells assessed as inhibition of cell proliferati... 26305181
Bromodomain-containing protein 2 IC50 = 244.0 nM 6.61 Binding affinity to human partial length BRD2 BD2 (E348to D455 residues) express... 36577036

Literature References

PubMed DOI Target Context # Activities
36577036 10.1021/acs.jmedchem.2c01770 Bromodomain-containing protein 3 14
36577036 10.1021/acs.jmedchem.2c01770 Bromodomain-containing protein 4 12
28257574 10.1021/acs.jmedchem.7b00069 ACHN 10
36577036 10.1021/acs.jmedchem.2c01770 Unchecked 10
36577036 10.1021/acs.jmedchem.2c01770 Bromodomain-containing protein 2 8
36577036 10.1021/acs.jmedchem.2c01770 Bromodomain testis-specific protein 4
26305181 10.1021/acs.jmedchem.5b00867 Mus musculus 4
26305181 10.1021/acs.jmedchem.5b00867 PC-3 3
26305181 10.1021/acs.jmedchem.5b00867 LNCaP 3
26305181 10.1021/acs.jmedchem.5b00867 Plasma 2
26305181 10.1021/acs.jmedchem.5b00867 HFF 1
28257574 10.1021/acs.jmedchem.7b00069 SN12C 1
28257574 10.1021/acs.jmedchem.7b00069 UO-31 1
28257574 10.1021/acs.jmedchem.7b00069 No relevant target 1
28257574 10.1021/acs.jmedchem.7b00069 CAKI-1 1
28617598 10.1021/acs.jnatprod.6b01129 LNCaP 1
28617598 10.1021/acs.jnatprod.6b01129 CWR22R 1
26305181 10.1021/acs.jmedchem.5b00867 SF-268 1
28617598 10.1021/acs.jnatprod.6b01129 M14 1
38278080 10.1016/j.ejmech.2024.116158 ACHN 1

Data from ChEMBL 36 via Core Engine