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Compound Detail

CHEMBL564481

CYCLODOXAZOSIN
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COc1cc2nc(N3CCN(C(=O)C4COc5ccccc5O4)[C@H]4CCCC[C@H]43)nc(N)c2cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL564481
Name CYCLODOXAZOSIN
Phase Preclinical
Structure Type MOL
InChI Key RZKGYUBITDXCBT-ZJWBFHOUSA-N
9
Targets
17
Activities
4
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

505.6
MW (Da)
3.03
ALogP
9
HBA
1
HBD
112.3
PSA (Ų)
0.57
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H31N5O5
MW 505.58
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -0.42

Activity Summary

Ki 6 meas. best 9.77
EC50 5 meas. best 5.85
IC50 4 meas. best 6.24
Kd 2 meas. best 7.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-1D adrenergic receptor
CHEMBL223
 Ki 9.77 9.09 0.2 2
Alpha-1B adrenergic receptor
CHEMBL232
 Ki 9.38 9.115 0.4 2
Alpha-1A adrenergic receptor
CHEMBL229
 Ki 8.55 8.51 2.8 2
Alpha-1D adrenergic receptor
CHEMBL326
 Kd 7.39 7.39 40.7 1
Alpha-1A adrenergic receptor
CHEMBL319
 Kd 6.7 6.7 199.5 1
LNCaP
CHEMBL612518
 IC50 6.24 6.24 570.0 1
PC-3
CHEMBL390
 IC50 6.07 6.07 850.0 1
DU-145
CHEMBL613508
 IC50 6.02 6.02 960.0 1
LNCaP
CHEMBL612518
 EC50 5.85 5.85 1420.0 1
NHDF
CHEMBL614200
 IC50 5.84 5.84 1460.0 1
PC-3
CHEMBL390
 EC50 5.73 5.365 1860.0 2
DU-145
CHEMBL613508
 EC50 5.58 5.58 2600.0 1
NHDF
CHEMBL614200
 EC50 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-1D adrenergic receptor Ki = 0.1698 nM 9.77 Displacement of [3H]prazosin from human Alpha-1D adrenoceptor expressed in CHO c... 19719240
Alpha-1B adrenergic receptor Ki = 0.4169 nM 9.38 Displacement of [3H]prazosin from human Alpha-1B adrenoceptor expressed in CHO c... 19719240
Alpha-1B adrenergic receptor Ki = 1.413 nM 8.85 Binding affinity to alpha1B adrenergic receptor (unknown origin) 29784274
Alpha-1A adrenergic receptor Ki = 2.818 nM 8.55 Displacement of [3H]prazosin from human alpha1A adrenoceptor expressed in CHO ce... 19719240
Alpha-1A adrenergic receptor Ki = 3.388 nM 8.47 Binding affinity to alpha1A adrenergic receptor (unknown origin) 29784274
Alpha-1D adrenergic receptor Ki = 3.89 nM 8.41 Binding affinity to alpha1D adrenergic receptor (unknown origin) 29784274
Alpha-1D adrenergic receptor Kd = 40.74 nM 7.39 Antagonist activity at rat Alpha-1D adrenoceptor assessed as inhibition if norep... 19719240
Alpha-1A adrenergic receptor Kd = 199.53 nM 6.7 Antagonist activity at alpha1A adrenergic receptor in Wistar rat prostatic rat v... 29784274
LNCaP IC50 = 570.0 nM 6.24 Cytotoxicity against human LNCAP cells after 72 hrs by CellTitter-Glo luminescen... 19719240
PC-3 IC50 = 850.0 nM 6.07 Cytotoxicity against human PC3 cells after 72 hrs by CellTitter-Glo luminescent ... 19719240
DU-145 IC50 = 960.0 nM 6.02 Cytotoxicity against human DU145 cells after 72 hrs by CellTitter-Glo luminescen... 19719240
LNCaP EC50 = 1420.0 nM 5.85 Cytotoxicity against human LNCAP cells after 72 hrs by CellTitter-Glo luminescen... 19719240
NHDF IC50 = 1460.0 nM 5.84 Cytotoxicity against human NHDF cells after 72 hrs by CellTitter-Glo luminescent... 19719240
PC-3 EC50 = 1860.0 nM 5.73 Cytotoxicity against human PC3 cells after 72 hrs by CellTitter-Glo luminescent ... 19719240
DU-145 EC50 = 2600.0 nM 5.58 Cytotoxicity against human DU145 cells after 72 hrs by CellTitter-Glo luminescen... 19719240
NHDF EC50 = 10000.0 nM 5.0 Induction of apoptosis in human NHDF cells assessed as caspase 3/7 activation af... 19719240
PC-3 EC50 = 10000.0 nM 5.0 Induction of apoptosis in human PC3 cells assessed as caspase 3/7 activation aft... 19719240

Literature References

PubMed DOI Target Context # Activities
19719240 10.1021/jm8016046 PC-3 9
29784274 10.1016/j.bmc.2018.05.023 Unchecked 6
19719240 10.1021/jm8016046 DU-145 3
19719240 10.1021/jm8016046 LNCaP 3
19719240 10.1021/jm8016046 NHDF 3
19719240 10.1021/jm8016046 Alpha-1A adrenergic receptor 2
19719240 10.1021/jm8016046 Alpha-1B adrenergic receptor 2
19719240 10.1021/jm8016046 Alpha-1D adrenergic receptor 2
29784274 10.1016/j.bmc.2018.05.023 Alpha-1A adrenergic receptor 2
29784274 10.1016/j.bmc.2018.05.023 Alpha-1B adrenergic receptor 2
29784274 10.1016/j.bmc.2018.05.023 Alpha-1D adrenergic receptor 2

Data from ChEMBL 36 via Core Engine