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Compound Detail

CHEMBL444590

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COc1cccc2c1CCCC2CCCN1CCN(c2ccccn2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL444590
Phase Preclinical
Structure Type MOL
InChI Key KKPMYWNQZNRGIK-UHFFFAOYSA-N
11
Targets
27
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

365.5
MW (Da)
4.11
ALogP
4
HBA
0
HBD
28.6
PSA (Ų)
0.77
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H31N3O
MW 365.52
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -1.08

Activity Summary

IC50 18 meas. best 9.27
Ki 8 meas. best 10.1
EC50 1 meas. best 9.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 10.1 9.71 0.1 2
Alpha-1A adrenergic receptor
CHEMBL229
 Ki 9.48 9.48 0.3 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 9.32 9.32 0.5 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 IC50 9.27 9.2625 0.5 4
5-hydroxytryptamine receptor 1A
CHEMBL214
 EC50 9.11 9.11 0.8 1
Alpha-1D adrenergic receptor
CHEMBL223
 Ki 8.22 8.22 6.0 1
Alpha-1B adrenergic receptor
CHEMBL232
 Ki 8.1 8.1 7.9 1
Adrenergic receptor alpha-1
CHEMBL1907610
 IC50 7.5 7.26 31.4 4
Adrenergic receptor alpha-2
CHEMBL2093864
 IC50 7.32 7.32 48.0 2
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 7.26 7.26 55.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 IC50 7.17 7.17 67.5 1
D(2) dopamine receptor
CHEMBL339
 Ki 6.93 6.93 117.0 1
D(2) dopamine receptor
CHEMBL339
 IC50 6.85 6.825 140.0 4
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 IC50 6.6 6.54 250.0 2
5-hydroxytryptamine receptor 2A
CHEMBL322
 IC50 6.6 6.6 250.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 1A Ki = 0.08 nM 10.1 Binding affinity on human cloned 5-hydroxytryptamine 1A receptor transfected in ... 11728188
Alpha-1A adrenergic receptor Ki = 0.33 nM 9.48 Binding affinity was determined on human cloned Alpha-1A adrenoceptor 11728188
5-hydroxytryptamine receptor 1A Ki = 0.48 nM 9.32 Binding was determined on 5-hydroxytryptamine 1A receptor in rat hippocampal mem... 11728188
5-hydroxytryptamine receptor 1A Ki = 0.48 nM 9.32 Agonist activity at human 5-HT1A receptor expressed in human HeLa cell membranes... 26081758
5-hydroxytryptamine receptor 1A IC50 = 0.54 nM 9.27 Binding affinity against serotonin 5-hydroxytryptamine 1A receptor in rat hippoc... 8759642
5-hydroxytryptamine receptor 1A IC50 = 0.54 nM 9.27 Binding affinity towards rat 5-hydroxytryptamine 1A receptor was evaluated using... 8960552
5-hydroxytryptamine receptor 1A IC50 = 0.54 nM 9.27 In vitro inhibition of [3H]8-OH-DPAT binding to rat 5-HT 1a receptors. 9986719
5-hydroxytryptamine receptor 1A IC50 = 0.58 nM 9.24 In vitro binding affinity measured on serotonin 5-hydroxytryptamine 1A receptor ... 7699710
5-hydroxytryptamine receptor 1A EC50 = 0.7762 nM 9.11 Agonist activity at human 5-HT1A receptor expressed in CHO cells assessed as inh... 26081758
Alpha-1D adrenergic receptor Ki = 5.95 nM 8.22 Binding affinity towarda alpha-1D adrenergic receptor 11728188
Alpha-1B adrenergic receptor Ki = 7.88 nM 8.1 Binding affinity was determined on human cloned alpha-1B adrenergic receptor 11728188
Adrenergic receptor alpha-1 IC50 = 31.4 nM 7.5 In vitro binding affinity measured on alpha-1 adrenergic receptor using [3H]praz... 7699710
Adrenergic receptor alpha-2 IC50 = 48.0 nM 7.32 Binding affinity against Alpha-2 adrenergic receptor in rat brain membrane using... 8759642
Adrenergic receptor alpha-2 IC50 = 48.0 nM 7.32 Binding affinity towards rat Alpha-2 adrenergic receptor was evaluated using [3H... 8960552
Adrenergic receptor alpha-1 Ki = 55.0 nM 7.26 Binding affinity towards alpha-1 adrenergic receptor in rat cortical membranes 11728188
Adrenergic receptor alpha-1 IC50 = 66.0 nM 7.18 Binding affinity against Alpha-1 adrenergic receptor in rat brain membrane using... 8759642
Adrenergic receptor alpha-1 IC50 = 66.0 nM 7.18 In vitro inhibition of [3H]prazosin binding to rat alpha-1 adrenergic receptors. 9986719
Adrenergic receptor alpha-1 IC50 = 66.0 nM 7.18 Binding affinity towards rat Alpha-1 adrenergic receptor was evaluated using [3H... 8960552
Sigma non-opioid intracellular receptor 1 IC50 = 67.5 nM 7.17 In vitro binding affinity measured on sigma opioid receptor using [3H]DTG as rad... 7699710
D(2) dopamine receptor Ki = 117.0 nM 6.93 Binding affinity towards dopamine receptor D2 in rat striatal membranes 11728188

Literature References

PubMed DOI Target Context # Activities
26081758 10.1016/j.bmc.2015.05.042 5-hydroxytryptamine receptor 1A 6
11728188 10.1021/jm010866v 5-hydroxytryptamine receptor 1A 4
8960552 10.1021/jm9604538 Unchecked 3
8759642 10.1021/jm960087s Unchecked 3
11728188 10.1021/jm010866v Unchecked 3
9986719 10.1021/jm980420n Unchecked 2
8960552 10.1021/jm9604538 Adrenergic receptor alpha-1 2
7699710 10.1021/jm00006a013 Unchecked 2
9986719 10.1021/jm980420n D(2) dopamine receptor 1
9986719 10.1021/jm980420n Adrenergic receptor alpha-1 1
9986719 10.1021/jm980420n 5-hydroxytryptamine receptor 1A 1
7699710 10.1021/jm00006a013 5-hydroxytryptamine receptor 1A 1
7699710 10.1021/jm00006a013 Serotonin 2 (5-HT2) receptor 1
7699710 10.1021/jm00006a013 D(2) dopamine receptor 1
7699710 10.1021/jm00006a013 Adrenergic receptor alpha-1 1
8759642 10.1021/jm960087s Adrenergic receptor alpha-2 1
8759642 10.1021/jm960087s Adrenergic receptor alpha-1 1
7699710 10.1021/jm00006a013 Serotonin 1a (5-HT1a) receptor/Adrenergic receptor alpha-1 1
8960552 10.1021/jm9604538 5-hydroxytryptamine receptor 1A 1
8759642 10.1021/jm960087s D(2) dopamine receptor 1

Data from ChEMBL 36 via Core Engine