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Compound Detail

CHEMBL561851

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COc1cc2nc(N(C)CCCCCCN(C)C(=O)C3COc4ccccc4O3)nc(N)c2cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL561851
Phase Preclinical
Structure Type MOL
InChI Key NXJYLDGTQWINTD-UHFFFAOYSA-N
7
Targets
9
Activities
3
Assay Types
0
PK Parameters
7
Publications
0
Known Names

Molecular Properties

509.6
MW (Da)
3.52
ALogP
9
HBA
1
HBD
112.3
PSA (Ų)
0.39
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H35N5O5
MW 509.61
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -0.55

Activity Summary

IC50 4 meas. best 5.34
Ki 3 meas. best 9.03
EC50 2 meas. best 5.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-1B adrenergic receptor
CHEMBL232
 Ki 9.03 9.03 0.9 1
Alpha-1D adrenergic receptor
CHEMBL223
 Ki 8.8 8.8 1.6 1
Alpha-1A adrenergic receptor
CHEMBL229
 Ki 8.73 8.73 1.9 1
LNCaP
CHEMBL612518
 IC50 5.34 5.34 4610.0 1
PC-3
CHEMBL390
 IC50 5.08 5.08 8400.0 1
DU-145
CHEMBL613508
 IC50 5.03 5.03 9250.0 1
NHDF
CHEMBL614200
 IC50 5.01 5.01 9800.0 1
PC-3
CHEMBL390
 EC50 5.0 5.0 10000.0 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-1B adrenergic receptor Ki = 0.9333 nM 9.03 Displacement of [3H]prazosin from human Alpha-1B adrenoceptor expressed in CHO c... 19719240
Alpha-1D adrenergic receptor Ki = 1.585 nM 8.8 Displacement of [3H]prazosin from human Alpha-1D adrenoceptor expressed in CHO c... 19719240
Alpha-1A adrenergic receptor Ki = 1.862 nM 8.73 Displacement of [3H]prazosin from human alpha1A adrenoceptor expressed in CHO ce... 19719240
LNCaP IC50 = 4610.0 nM 5.34 Cytotoxicity against human LNCAP cells after 72 hrs by CellTitter-Glo luminescen... 19719240
PC-3 IC50 = 8400.0 nM 5.08 Cytotoxicity against human PC3 cells after 72 hrs by CellTitter-Glo luminescent ... 19719240
DU-145 IC50 = 9250.0 nM 5.03 Cytotoxicity against human DU145 cells after 72 hrs by CellTitter-Glo luminescen... 19719240
NHDF IC50 = 9800.0 nM 5.01 Cytotoxicity against human NHDF cells after 72 hrs by CellTitter-Glo luminescent... 19719240
PC-3 EC50 = 10000.0 nM 5.0 Induction of apoptosis in human PC3 cells assessed as caspase 3/7 activation aft... 19719240
NHDF EC50 = 10000.0 nM 5.0 Induction of apoptosis in human NHDF cells assessed as caspase 3/7 activation af... 19719240

Literature References

PubMed DOI Target Context # Activities
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
19719240 10.1021/jm8016046 PC-3 2
19719240 10.1021/jm8016046 DU-145 2
19719240 10.1021/jm8016046 LNCaP 2
19719240 10.1021/jm8016046 NHDF 2

Data from ChEMBL 36 via Core Engine