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Compound Detail

CHEMBL4085780

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O=C1CCc2ccccc2N1CCCN1CCN(c2ccccc2)CC1

Basic Information

ChEMBL ID CHEMBL4085780
Phase Preclinical
Structure Type MOL
InChI Key ABOBMBIQQPJTMJ-UHFFFAOYSA-N
16
Targets
26
Activities
3
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

349.5
MW (Da)
3.18
ALogP
3
HBA
0
HBD
26.8
PSA (Ų)
0.83
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H27N3O
MW 349.48
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -1.36

Activity Summary

Ki 19 meas. best 8.54
IC50 4 meas. best 9.14
EC50 3 meas. best 9.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(4) dopamine receptor
CHEMBL219
EC50 9.8 9.8 0.2 1
D(4) dopamine receptor
CHEMBL219
IC50 9.14 8.575 0.7 2
D(4) dopamine receptor
CHEMBL219
Ki 8.54 8.54 2.9 2
Alpha-1A adrenergic receptor
CHEMBL229
Ki 7.27 7.27 53.7 1
Alpha-1B adrenergic receptor
CHEMBL232
Ki 7.13 7.13 74.1 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 7.04 7.04 91.2 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
Ki 6.57 6.57 269.1 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
EC50 6.23 6.23 588.8 1
Muscarinic acetylcholine receptor M1
CHEMBL216
EC50 6.19 6.19 645.6 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 6.08 6.08 831.8 1
D(2) dopamine receptor
CHEMBL217
Ki 5.96 5.96 1096.5 2
D(3) dopamine receptor
CHEMBL234
Ki 5.88 5.88 1318.3 2
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 5.37 5.37 4265.8 1
Sodium-dependent serotonin transporter
CHEMBL313
Ki 5.3 5.3 5011.9 1
Sodium-dependent dopamine transporter
CHEMBL338
Ki 5.06 5.06 8709.6 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 5.03 5.03 9332.5 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 4.92 4.92 12022.6 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 4.78 4.78 16595.9 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 4.75 4.75 17782.8 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 4.56 4.56 27542.3 1
Beta-1 adrenergic receptor
CHEMBL213
Ki 4.49 4.49 32359.4 1
Beta-2 adrenergic receptor
CHEMBL210
Ki 4.45 4.45 35481.3 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2384.0 ng.hr.mL-1 Mus musculus
AUC 518.0 ng.hr.mL-1 Mus musculus
Cmax 2046.0 ng/g Mus musculus
Cmax 1376.33 nM Mus musculus
Fu 0.033 - Homo sapiens
Fu 0.097 - Mus musculus
Fu 0.086 - Mus musculus
T1/2 0.1452 hr Mus musculus
T1/2 0.93 hr Mus musculus
T1/2 0.77 hr Mus musculus
Tmax 0.25 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(4) dopamine receptor EC50 = 0.1585 nM 9.8 Agonist activity at human SP/Myc epitope-tagged dopamine D4 receptor expressed i... 29589445
D(4) dopamine receptor IC50 = 0.7244 nM 9.14 Antagonist activity at human SP/Myc epitope-tagged dopamine D4 receptor expresse... 29589445
D(4) dopamine receptor Ki = 2.884 nM 8.54 Displacement of [3H]N-methylspiperone from human dopamine D4 receptor expressed ... 29589445
D(4) dopamine receptor Ki = 2.884 nM 8.54 Displacement of [3H]N-methylspiperone from human D4.4 receptor expressed in HEK2... 36098685
D(4) dopamine receptor IC50 = 9.772 nM 8.01 Antagonist activity at human SP/Myc epitope-tagged dopamine D4 receptor expresse... 29589445
Alpha-1A adrenergic receptor Ki = 53.7 nM 7.27 Displacement of [3H]prazosin from human recombinant alpha-1A adrenergic receptor... 29589445
Alpha-1B adrenergic receptor Ki = 74.13 nM 7.13 Displacement of [3H]prazosin from human recombinant alpha-1B adrenergic receptor... 29589445
Alpha-1D adrenergic receptor Ki = 91.2 nM 7.04 Displacement of [3H]prazosin from human recombinant alpha-1D adrenergic receptor... 29589445
Sigma non-opioid intracellular receptor 1 Ki = 269.15 nM 6.57 Displacement of [3H](+)-pentazocine from sigma1 receptor in Hartley guinea pig b... 29589445
Muscarinic acetylcholine receptor M4 EC50 = 588.84 nM 6.23 Agonist activity at human SP/Myc epitope-tagged muscarinic M4 receptor expressed... 29589445
Muscarinic acetylcholine receptor M1 EC50 = 645.65 nM 6.19 Agonist activity at human SP/Myc epitope-tagged muscarinic M1 receptor expressed... 29589445
Muscarinic acetylcholine receptor M1 IC50 = 831.76 nM 6.08 Antagonist activity at human SP/Myc epitope-tagged muscarinic M1 receptor expres... 29589445
D(2) dopamine receptor Ki = 1096.48 nM 5.96 Displacement of [3H]N-methylspiperone from human dopamine D2 receptor expressed ... 29589445
D(2) dopamine receptor Ki = 1096.48 nM 5.96 Displacement of [3H]N-methylspiperone from human D2L receptor expressed in HEK29... 36098685
D(3) dopamine receptor Ki = 1318.26 nM 5.88 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor expressed ... 29589445
D(3) dopamine receptor Ki = 1318.26 nM 5.88 Displacement of [3H]N-methylspiperone from human D3R receptor expressed in HEK29... 36098685
Muscarinic acetylcholine receptor M1 Ki = 4265.8 nM 5.37 Displacement of [3H]NMS from human muscarinic M1 receptor expressed in CHO cell ... 29589445
Sodium-dependent serotonin transporter Ki = 5011.87 nM 5.3 Displacement of [3H]-citalopram from SERT in Sprague-Dawley rat midbrain after 6... 29589445
Sodium-dependent dopamine transporter Ki = 8709.64 nM 5.06 Displacement of [3H]WIN 35,428 from DAT in Sprague-Dawley rat striatum after 120... 29589445
Muscarinic acetylcholine receptor M4 Ki = 9332.54 nM 5.03 Displacement of [3H]NMS from human muscarinic M4 receptor expressed in CHO cell ... 29589445

Literature References

PubMed DOI Target Context # Activities
29589445 10.1021/acs.jmedchem.8b00265 D(4) dopamine receptor 8
29589445 10.1021/acs.jmedchem.8b00265 Muscarinic acetylcholine receptor M1 8
29589445 10.1021/acs.jmedchem.8b00265 Muscarinic acetylcholine receptor M4 8
29589445 10.1021/acs.jmedchem.8b00265 Plasma 7
29589445 10.1021/acs.jmedchem.8b00265 Brain 6
29589445 10.1021/acs.jmedchem.8b00265 MDCK-II 5
29589445 10.1021/acs.jmedchem.8b00265 Liver 3
29589445 10.1021/acs.jmedchem.8b00265 ADMET 2
36098685 10.1021/acs.jmedchem.2c00840 Unchecked 2
29589445 10.1021/acs.jmedchem.8b00265 Alpha-1A adrenergic receptor 1
29589445 10.1021/acs.jmedchem.8b00265 Sigma non-opioid intracellular receptor 1 1
29589445 10.1021/acs.jmedchem.8b00265 Beta-2 adrenergic receptor 1
29589445 10.1021/acs.jmedchem.8b00265 Beta-1 adrenergic receptor 1
29589445 10.1021/acs.jmedchem.8b00265 Alpha-1D adrenergic receptor 1
29589445 10.1021/acs.jmedchem.8b00265 Alpha-1B adrenergic receptor 1
29589445 10.1021/acs.jmedchem.8b00265 D(2) dopamine receptor 1
29589445 10.1021/acs.jmedchem.8b00265 Muscarinic acetylcholine receptor M3 1
29589445 10.1021/acs.jmedchem.8b00265 Muscarinic acetylcholine receptor M2 1
29589445 10.1021/acs.jmedchem.8b00265 Dopamine receptors; D3 & D4 1
29589445 10.1021/acs.jmedchem.8b00265 Unchecked 1

Data from ChEMBL 36 via Core Engine