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Compound Detail

CHEMBL4072818

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O=C1CCc2ccccc2N1CCCN1CCC(Cc2ccccc2)CC1

Basic Information

ChEMBL ID CHEMBL4072818
Phase Preclinical
Structure Type MOL
InChI Key YCGXHEJETHPGPD-UHFFFAOYSA-N
16
Targets
24
Activities
3
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

362.5
MW (Da)
4.31
ALogP
2
HBA
0
HBD
23.6
PSA (Ų)
0.76
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 C24H30N2O
MW 362.52
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.86

Activity Summary

Ki 16 meas. best 8.9
IC50 6 meas. best 6.77
EC50 2 meas. best 6.83

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(4) dopamine receptor
CHEMBL219
Ki 8.9 8.9 1.3 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
Ki 8.0 8.0 10.0 1
Sodium-dependent serotonin transporter
CHEMBL313
Ki 7.33 7.33 46.8 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
EC50 6.83 6.83 147.9 1
D(4) dopamine receptor
CHEMBL219
IC50 6.77 6.505 169.8 2
Muscarinic acetylcholine receptor M1
CHEMBL216
EC50 6.73 6.73 186.2 1
Alpha-1B adrenergic receptor
CHEMBL232
Ki 6.65 6.65 223.9 1
Alpha-1A adrenergic receptor
CHEMBL229
Ki 6.59 6.59 257.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.52 6.52 302.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 6.44 6.44 363.1 1
Sodium-dependent dopamine transporter
CHEMBL338
Ki 6.35 6.35 446.7 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 6.14 6.14 724.4 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.1 6.1 794.3 1
D(2) dopamine receptor
CHEMBL217
Ki 6.04 6.04 912.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 5.92 5.75 1202.3 2
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 5.91 5.49 1230.3 2
D(3) dopamine receptor
CHEMBL234
Ki 5.74 5.74 1819.7 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 5.52 5.52 3019.9 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 5.43 5.43 3715.3 1
Beta-2 adrenergic receptor
CHEMBL210
Ki 5.02 5.02 9549.9 1
Beta-1 adrenergic receptor
CHEMBL213
Ki 4.99 4.99 10232.9 1

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.057 - Homo sapiens
Fu 0.1 - Mus musculus
Fu 0.051 - Mus musculus
T1/2 0.05833 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(4) dopamine receptor Ki = 1.259 nM 8.9 Displacement of [3H]N-methylspiperone from human dopamine D4 receptor expressed ... 29589445
Sigma non-opioid intracellular receptor 1 Ki = 10.0 nM 8.0 Displacement of [3H](+)-pentazocine from sigma1 receptor in Hartley guinea pig b... 29589445
Sodium-dependent serotonin transporter Ki = 46.77 nM 7.33 Displacement of [3H]-citalopram from SERT in Sprague-Dawley rat midbrain after 6... 29589445
Muscarinic acetylcholine receptor M4 EC50 = 147.91 nM 6.83 Agonist activity at human SP/Myc epitope-tagged muscarinic M4 receptor expressed... 29589445
D(4) dopamine receptor IC50 = 169.82 nM 6.77 Antagonist activity at human SP/Myc epitope-tagged dopamine D4 receptor expresse... 29589445
Muscarinic acetylcholine receptor M1 EC50 = 186.21 nM 6.73 Agonist activity at human SP/Myc epitope-tagged muscarinic M1 receptor expressed... 29589445
Alpha-1B adrenergic receptor Ki = 223.87 nM 6.65 Displacement of [3H]prazosin from human recombinant alpha-1B adrenergic receptor... 29589445
Alpha-1A adrenergic receptor Ki = 257.04 nM 6.59 Displacement of [3H]prazosin from human recombinant alpha-1A adrenergic receptor... 29589445
Alpha-1D adrenergic receptor Ki = 302.0 nM 6.52 Displacement of [3H]prazosin from human recombinant alpha-1D adrenergic receptor... 29589445
Muscarinic acetylcholine receptor M1 Ki = 363.08 nM 6.44 Displacement of [3H]NMS from human muscarinic M1 receptor expressed in CHO cell ... 29589445
Sodium-dependent dopamine transporter Ki = 446.68 nM 6.35 Displacement of [3H]WIN 35,428 from DAT in Sprague-Dawley rat striatum after 120... 29589445
D(4) dopamine receptor IC50 = 575.44 nM 6.24 Antagonist activity at human SP/Myc epitope-tagged dopamine D4 receptor expresse... 29589445
Muscarinic acetylcholine receptor M4 Ki = 724.44 nM 6.14 Displacement of [3H]NMS from human muscarinic M4 receptor expressed in CHO cell ... 29589445
Muscarinic acetylcholine receptor M2 Ki = 794.33 nM 6.1 Displacement of [3H]NMS from human muscarinic M2 receptor expressed in CHO cell ... 29589445
D(2) dopamine receptor Ki = 912.01 nM 6.04 Displacement of [3H]N-methylspiperone from human dopamine D2 receptor expressed ... 29589445
Muscarinic acetylcholine receptor M1 IC50 = 1202.26 nM 5.92 Antagonist activity at human SP/Myc epitope-tagged muscarinic M1 receptor expres... 29589445
Muscarinic acetylcholine receptor M4 IC50 = 1230.27 nM 5.91 Antagonist activity at human SP/Myc epitope-tagged muscarinic M4 receptor expres... 29589445
D(3) dopamine receptor Ki = 1819.7 nM 5.74 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor expressed ... 29589445
Muscarinic acetylcholine receptor M1 IC50 = 2630.27 nM 5.58 Antagonist activity at human SP/Myc epitope-tagged muscarinic M1 receptor expres... 29589445
Muscarinic acetylcholine receptor M3 Ki = 3019.95 nM 5.52 Displacement of [3H]NMS from human muscarinic M3 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 MDCK-II 5
29589445 10.1021/acs.jmedchem.8b00265 Liver 3
29589445 10.1021/acs.jmedchem.8b00265 Plasma 2
29589445 10.1021/acs.jmedchem.8b00265 Alpha-1A adrenergic receptor 1
29589445 10.1021/acs.jmedchem.8b00265 Sodium-dependent serotonin transporter 1
29589445 10.1021/acs.jmedchem.8b00265 Sodium-dependent dopamine transporter 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 M5 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