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Compound Detail

CHEMBL333465

LOBELANE
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CN1[C@@H](CCc2ccccc2)CCC[C@H]1CCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL333465
Name LOBELANE
Phase Preclinical
Structure Type MOL
InChI Key ISVBJSRQEBWKPB-SZPZYZBQSA-N
6
Targets
19
Activities
1
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

307.5
MW (Da)
5.10
ALogP
1
HBA
0
HBD
3.2
PSA (Ų)
0.72
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H29N
MW 307.48
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.04

Activity Summary

Ki 19 meas. best 7.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Synaptic vesicular amine transporter
CHEMBL4828
 Ki 7.48 6.4657 33.0 14
Synaptic vesicular amine transporter
CHEMBL1893
 Ki 6.01 6.01 970.0 1
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 5.98 5.98 1050.0 1
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 5.44 5.44 3600.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 Ki 4.83 4.83 14900.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
 Ki 4.58 4.58 26000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Synaptic vesicular amine transporter Ki = 33.0 nM 7.48 Inhibition of [3H]dopamine uptake at VMAT2 in rat brain synaptic vesicle by liqu... 19691331
Synaptic vesicular amine transporter Ki = 45.0 nM 7.35 Inhibition of VMAT2-mediated [3H]-dopamine uptake in rat striata isolated synapt... 23993667
Synaptic vesicular amine transporter Ki = 45.0 nM 7.35 Inhibition of [3H]DA uptake at VMAT2 in rat striatal synaptic vesicles 23527317
Synaptic vesicular amine transporter Ki = 45.0 nM 7.35 Inhibition of VMAT2-mediated [3H]DA uptake in rat brain synaptic vesicles by liq... 25991431
Synaptic vesicular amine transporter Ki = 45.0 nM 7.35 Inhibition of [3H]dopamine uptake at VMAT2 in rat synaptic vesicles after 8 mins... 29153425
Synaptic vesicular amine transporter Ki = 67.0 nM 7.17 Inhibition of VMAT2 in rat striatal synaptic vesicle assessed as reduction of [3... 27080180
Synaptic vesicular amine transporter Ki = 970.0 nM 6.01 Displacement of [3H]DTBZ from VMAT2 dihydrotetrabenazine binding site in rat bra... 19691331
Synaptic vesicular amine transporter Ki = 970.0 nM 6.01 Displacement of [3H]DTBZ from VMAT2 in rat whole brain by liquid scintillation s... 25991431
Synaptic vesicular amine transporter Ki = 970.0 nM 6.01 Inhibition of [3H]DTBZ binding to VMAT2 in rat synaptic vesicle membranes 23527317
Synaptic vesicular amine transporter Ki = 970.0 nM 6.01 Binding affinity to VMAT2 receptor 20036131
Synaptic vesicular amine transporter Ki = 970.0 nM 6.01 Displacement of [3H]dihydrotetrabenazine from vesicular monoamine transporter-2 ... 18976906
Synaptic vesicular amine transporter Ki = 970.0 nM 6.01 Inhibition constant against [3H]dihydrotetrabenazine binding to vesicular monoam... 16112864
Synaptic vesicular amine transporter Ki = 970.0 nM 6.01 Inhibition of 5 nM [3H]DTBZ binding to Vesicular Monoamine Transporter (VAMT2) o... 16107155
Sodium-dependent dopamine transporter Ki = 1050.0 nM 5.98 Inhibition of DAT in rat striatal synaptosomes assessed as reduction of [3H]dopa... 27080180
Synaptic vesicular amine transporter Ki = 2600.0 nM 5.58 Inhibition constant against [3H]methyllycaconitine binding to vesicular monoamin... 16112864
Sodium-dependent serotonin transporter Ki = 3600.0 nM 5.44 Inhibition of SERT in rat striatal synaptosomes assessed as reduction of [3H]5-H... 27080180
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 14900.0 nM 4.83 Inhibition of 3 nM [3H]NIC binding to Nicotinic acetylcholine receptor alpha4-be... 16107155
Synaptic vesicular amine transporter Ki = 14900.0 nM 4.83 Inhibition constant against [3H]nicotine binding to vesicular monoamine transpor... 16112864
Neuronal acetylcholine receptor subunit alpha-7 Ki = 26000.0 nM 4.58 Inhibition of 3 nM [3H]-MLA binding to Nicotinic acetylcholine receptor alpha7 o... 16107155

Literature References

PubMed DOI Target Context # Activities
29153425 10.1016/j.bmcl.2017.10.039 Unchecked 3
16112864 10.1016/j.bmcl.2005.07.032 Synaptic vesicular amine transporter 3
19691331 10.1021/jm900770h Synaptic vesicular amine transporter 3
25991431 10.1016/j.bmcl.2015.04.105 Synaptic vesicular amine transporter 3
16107155 10.1021/jm0501228 Unchecked 2
23527317 10.1039/c3md20374c Synaptic vesicular amine transporter 2
23993667 10.1016/j.bmc.2013.08.001 Synaptic vesicular amine transporter 1
29153425 10.1016/j.bmcl.2017.10.039 Synaptic vesicular amine transporter 1
27212067 10.1016/j.bmcl.2016.05.025 Unchecked 1
27080180 10.1016/j.bmcl.2016.03.119 Sodium-dependent serotonin transporter 1
27080180 10.1016/j.bmcl.2016.03.119 Sodium-dependent dopamine transporter 1
27080180 10.1016/j.bmcl.2016.03.119 Synaptic vesicular amine transporter 1
10479304 10.1021/jm990286m Neuronal acetylcholine receptor 1
20036131 10.1016/j.bmc.2009.12.002 Synaptic vesicular amine transporter 1
18976906 10.1016/j.bmcl.2008.10.042 Synaptic vesicular amine transporter 1
16107155 10.1021/jm0501228 Synaptic vesicular amine transporter 1
16107155 10.1021/jm0501228 Neuronal acetylcholine receptor subunit alpha-7 1
16107155 10.1021/jm0501228 Neuronal acetylcholine receptor; alpha4/beta2 1

Data from ChEMBL 36 via Core Engine