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Compound Detail

CHEMBL4476784

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COc1ccc(OCCN2CCN(C(=O)c3cc4ccccc4[nH]3)CC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4476784
Phase Preclinical
Structure Type MOL
InChI Key HAZPAMUWUHDPDA-UHFFFAOYSA-N
7
Targets
23
Activities
2
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

379.5
MW (Da)
3.01
ALogP
4
HBA
1
HBD
57.8
PSA (Ų)
0.72
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H25N3O3
MW 379.46
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -1.29

Activity Summary

Ki 15 meas. best 7.9
EC50 8 meas. best 9.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(3) dopamine receptor
CHEMBL234
 EC50 9.74 7.79 0.2 8
D(3) dopamine receptor
CHEMBL234
 Ki 7.9 6.5438 12.5 8
Beta-1 adrenergic receptor
CHEMBL213
 Ki 7.11 7.11 77.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 6.42 6.42 383.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.17 5.695 674.0 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 5.68 5.68 2108.0 1
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 5.56 5.56 2750.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 5.55 5.55 2841.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 17129.61 nM Mus musculus
Cmax 73789.07 nM Mus musculus
T1/2 0.3533 hr Not specified
T1/2 3.44 hr Mus musculus
T1/2 4.23 hr Mus musculus
Tmax 0.5 hr Mus musculus
Tmax 0.25 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(3) dopamine receptor EC50 = 0.18 nM 9.74 Agonist activity at RLuc8-fused Go-coupled human D3R expressed in HEK293 cells u... 32342685
D(3) dopamine receptor EC50 = 1.2 nM 8.92 Agonist activity at RLuc8-fused human D3R expressed in HEK293 cells co-expressin... 32342685
D(3) dopamine receptor Ki = 12.5 nM 7.9 Displacement of [3H]-7-OH-DPAT from human D3R expressed in HEK293 cell membranes... 32342685
D(3) dopamine receptor EC50 = 17.0 nM 7.77 Agonist activity at RLuc8-fused human D3R Y198A mutant expressed in HEK293 cells... 32342685
D(3) dopamine receptor EC50 = 21.0 nM 7.68 Agonist activity at human D3R stably expressed in CHOK1 cells assessed as increa... 32342685
D(3) dopamine receptor Ki = 22.0 nM 7.66 Displacement of [3H]-7-OH-DPAT from human D3R expressed in HEK293 cell membranes... 32342685
D(3) dopamine receptor EC50 = 36.0 nM 7.44 D3 Radioligand Binding Assay: Compounds were tested for their ability to compete... -
D(3) dopamine receptor EC50 = 38.0 nM 7.42 Agonist activity at human D3R expressed in CHOK1 cells assessed as induction of ... 32342685
Beta-1 adrenergic receptor Ki = 77.0 nM 7.11 Displacement of [125I]-pindolol from recombinant human beta1 adrenergic receptor... 32342685
D(3) dopamine receptor EC50 = 86.0 nM 7.07 Agonist activity at human D3R expressed in HEK293 cells assessed as inhibition o... 32342685
D(3) dopamine receptor Ki = 94.0 nM 7.03 Displacement of [3H]-7-OH-DPAT from human D3R expressed in HEK293 cell membranes... 32342685
D(3) dopamine receptor Ki = 350.0 nM 6.46 Displacement of [3H]-methylspiperon from human D3R expressed in HEK293 cell memb... 32342685
Sigma non-opioid intracellular receptor 1 Ki = 383.0 nM 6.42 Displacement of [3H]-pentazocine from sigma1 receptor (unknown origin) after 90 ... 32342685
D(3) dopamine receptor EC50 = 520.0 nM 6.28 Agonist activity at RLuc8-fused human D3R Y365A mutant expressed in HEK293 cells... 32342685
5-hydroxytryptamine receptor 2B Ki = 674.0 nM 6.17 Displacement of [3H]-LSD from recombinant human 5HT2B receptor stably expressed ... 32342685
D(3) dopamine receptor Ki = 720.0 nM 6.14 Displacement of [3H]-7-OH-DPAT from human D3R expressed in HEK293 cell membranes... 32342685
D(3) dopamine receptor Ki = 1240.0 nM 5.91 Displacement of [3H]-N-methylspiperone from D3 receptor (unknown origin) measure... 32342685
D(3) dopamine receptor Ki = 1500.0 nM 5.82 Displacement of [3H]-methylspiperon from human D3R expressed in HEK293 cell memb... 32342685
5-hydroxytryptamine receptor 1A Ki = 2108.0 nM 5.68 Displacement of [3H]-Way100635 from recombinant human 5HT1A receptor stably expr... 32342685
Sigma intracellular receptor 2 Ki = 2750.0 nM 5.56 Displacement of [3H]-DTG from sigma 2 receptor (unknown origin) measured after 9... 32342685

Literature References

PubMed DOI Target Context # Activities
32342685 10.1021/acs.jmedchem.0c00424 D(3) dopamine receptor 25
32342685 10.1021/acs.jmedchem.0c00424 D(2) dopamine receptor 8
32342685 10.1021/acs.jmedchem.0c00424 ADMET 8
32342685 10.1021/acs.jmedchem.0c00424 HepG2 6
32342685 10.1021/acs.jmedchem.0c00424 5-hydroxytryptamine receptor 2B 6
32342685 10.1021/acs.jmedchem.0c00424 Unchecked 6
32342685 10.1021/acs.jmedchem.0c00424 D(4) dopamine receptor 4
32342685 10.1021/acs.jmedchem.0c00424 D(1A) dopamine receptor 4
32342685 10.1021/acs.jmedchem.0c00424 D(1B) dopamine receptor 4
32342685 10.1021/acs.jmedchem.0c00424 5-hydroxytryptamine receptor 2A 3
32342685 10.1021/acs.jmedchem.0c00424 Alpha-1B adrenergic receptor 3
32342685 10.1021/acs.jmedchem.0c00424 Histamine H1 receptor 3
32342685 10.1021/acs.jmedchem.0c00424 Histamine H2 receptor 3
32342685 10.1021/acs.jmedchem.0c00424 Histamine H3 receptor 3
32342685 10.1021/acs.jmedchem.0c00424 Mu-type opioid receptor 3
32342685 10.1021/acs.jmedchem.0c00424 Alpha-2A adrenergic receptor 3
32342685 10.1021/acs.jmedchem.0c00424 Alpha-2B adrenergic receptor 3
32342685 10.1021/acs.jmedchem.0c00424 Alpha-2C adrenergic receptor 3
32342685 10.1021/acs.jmedchem.0c00424 5-hydroxytryptamine receptor 1A 2
32342685 10.1021/acs.jmedchem.0c00424 Sigma intracellular receptor 2 2

Data from ChEMBL 36 via Core Engine