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BDBM50080818 (-)-lobeline::2-(6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone::2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone::2-{(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethanone::8,10-Diphenyllobelionol::CHEMBL122270::Lobelin::Lobnico::alpha-Lobeline

SMILES: CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1

InChI Key: InChIKey=MXYUKLILVYORSK-HBMCJLEFSA-N

Data: 16 KI  2 IC50

PDB links: 9 PDB IDs match this monomer.

Find this compound or compounds like it in BindingDB or PDB:
   Substructure
Similarity at least:  must be >=0.5
Exact match

Activity Spreadsheet -- Enzyme Inhibition Constant Data from BindingDB

Found 18 hits for monomerid = 50080818   
Target/Host
(Institution)
LigandTarget/Host
Links
Ligand
Links
Trg + Lig
Links
Ki
nM
ΔG°
kcal/mole
IC50
nM
Kd
nM
EC50/IC50
nM
koff
s-1
kon
M-1s-1
pHTemp
°C
Synaptic vesicular amine transporter


(Rattus norvegicus (Rat))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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4n/an/an/an/an/an/an/an/a



University of Kentucky

Curated by ChEMBL


Assay Description
Inhibition constant against [3H]-nicotine binding to vesicular monoamine transporter-2 of rat brain membranes


Bioorg Med Chem Lett 15: 4463-6 (2005)


Article DOI: 10.1016/j.bmcl.2005.07.032
BindingDB Entry DOI: 10.7270/Q2J38S3H
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Rattus norvegicus (Rat))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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2.76E+3n/an/an/an/an/an/an/an/a



University of Arkansas for Medical Sciences

Curated by ChEMBL


Assay Description
Inhibition of [3H]DTBZ binding to VMAT2 in rat synaptic vesicle membranes


Medchemcomm 4: 564-568 (2013)


Article DOI: 10.1039/c3md20374c
BindingDB Entry DOI: 10.7270/Q2KD21VD
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Rattus norvegicus (Rat))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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2.76E+3n/an/an/an/an/an/an/an/a



University of Kentucky

Curated by ChEMBL


Assay Description
Inhibition constant against [3H]-dihydrotetrabenazine binding to vesicular monoamine transporter-2 of rat synaptic vesicle membranes


Bioorg Med Chem Lett 15: 4463-6 (2005)


Article DOI: 10.1016/j.bmcl.2005.07.032
BindingDB Entry DOI: 10.7270/Q2J38S3H
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Rattus norvegicus (Rat))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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2.76E+3n/an/an/an/an/an/an/an/a



University of Kentucky

Curated by ChEMBL


Assay Description
Displacement of [3H]dihydrotetrabenazine from vesicular monoamine transporter-2 in rat brain synaptosome


Bioorg Med Chem Lett 18: 6509-12 (2008)


Article DOI: 10.1016/j.bmcl.2008.10.042
BindingDB Entry DOI: 10.7270/Q2NK3DW4
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Rattus norvegicus (Rat))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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2.76E+3n/an/an/an/an/an/an/an/a



University of Kentucky

Curated by ChEMBL


Assay Description
Inhibition of 5 nM [3H]DTBZ binding to Vesicular Monoamine Transporter (VAMT2) of rat vesicle membranes


J Med Chem 48: 5551-60 (2005)


Article DOI: 10.1021/jm0501228
BindingDB Entry DOI: 10.7270/Q2CN74Q9
More data for this
Ligand-Target Pair
Neuronal acetylcholine receptor subunit alpha-7


(Rattus norvegicus (Rat))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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6.26E+3n/an/an/an/an/an/an/an/a



University of Kentucky

Curated by ChEMBL


Assay Description
Inhibition of 3 nM [3H]-MLA binding to Nicotinic acetylcholine receptor alpha7 of rat brain membranes


J Med Chem 48: 5551-60 (2005)


Article DOI: 10.1021/jm0501228
BindingDB Entry DOI: 10.7270/Q2CN74Q9
More data for this
Ligand-Target Pair
Neuronal acetylcholine receptor subunit alpha-4/beta-2


(Homo sapiens (Human))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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5.01n/an/an/an/an/an/an/an/a



VU University Amsterdam

Curated by ChEMBL


Assay Description
Displacement of [3H]epibatidine from human nAChR alpha4beta2 receptor expressed in human HEK293T cells by scintillation counting


Bioorg Med Chem Lett 22: 1448-54 (2012)


Article DOI: 10.1016/j.bmcl.2011.12.008
BindingDB Entry DOI: 10.7270/Q26Q1ZHD
More data for this
Ligand-Target Pair
Acetylcholine-binding protein


(Lymnaea stagnalis)
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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631n/an/an/an/an/an/an/an/a



VU University Amsterdam

Curated by ChEMBL


Assay Description
Displacement of [3H]epibatidine from Lymnaea stagnalis acetylcholine binding protein expressed using baculoviral system after 1.5 hrs by scintillatio...


Bioorg Med Chem Lett 22: 1448-54 (2012)


Article DOI: 10.1016/j.bmcl.2011.12.008
BindingDB Entry DOI: 10.7270/Q26Q1ZHD
More data for this
Ligand-Target Pair
Soluble acetylcholine receptor


(Aplysia Californica)
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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2.51n/an/an/an/an/an/an/an/a



VU University Amsterdam

Curated by ChEMBL


Assay Description
Displacement of [3H]epibatidine from Aplysia californica acetylcholine binding protein expressed using baculoviral system after 1.5 hrs by scintillat...


Bioorg Med Chem Lett 22: 1448-54 (2012)


Article DOI: 10.1016/j.bmcl.2011.12.008
BindingDB Entry DOI: 10.7270/Q26Q1ZHD
More data for this
Ligand-Target Pair
Neuronal acetylcholine receptor subunit alpha-7


(Homo sapiens (Human))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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7.94E+3n/an/an/an/an/an/an/an/a



VU University Amsterdam

Curated by ChEMBL


Assay Description
Displacement of [3H]MLA from nAChR alpha7 receptor in human SH-SY5Y cells by scintillation counting


Bioorg Med Chem Lett 22: 1448-54 (2012)


Article DOI: 10.1016/j.bmcl.2011.12.008
BindingDB Entry DOI: 10.7270/Q26Q1ZHD
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Homo sapiens (Human))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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1.84E+3n/an/an/an/an/an/an/an/a



Organix Inc

Curated by ChEMBL


Assay Description
Displacement of [3H]reserpine from human VMAT2 expressed in HEK293 cell membranes incubated for 60 mins by scintillation counting method


J Med Chem 61: 9121-9131 (2018)


Article DOI: 10.1021/acs.jmedchem.8b00542
BindingDB Entry DOI: 10.7270/Q2KH0QZ9
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Mus musculus)
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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n/an/a 381n/an/an/an/an/an/a



Organix Inc

Curated by ChEMBL


Assay Description
Inhibition of VMAT2 in C57Bl/6J mouse striatal membranes assessed as reduction in [3H[-5HT uptake pre-incubated for 10 mins before [3H[-5HT addition ...


J Med Chem 61: 9121-9131 (2018)


Article DOI: 10.1021/acs.jmedchem.8b00542
BindingDB Entry DOI: 10.7270/Q2KH0QZ9
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Homo sapiens (Human))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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n/an/a 4.20E+3n/an/an/an/an/an/a



Organix Inc

Curated by ChEMBL


Assay Description
Inhibition of human VMAT2 expressed in HEK293 cell membranes assessed as reduction in [3H[-5HT uptake pre-incubated for 10 mins before [3H[-5HT addit...


J Med Chem 61: 9121-9131 (2018)


Article DOI: 10.1021/acs.jmedchem.8b00542
BindingDB Entry DOI: 10.7270/Q2KH0QZ9
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Homo sapiens (Human))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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>1.00E+4n/an/an/an/an/an/an/an/a



Organix Inc

Curated by ChEMBL


Assay Description
Displacement of [3H]DHTB from human VMAT2 expressed in HEK293 cell membranes incubated for 90 mins by microbeta scintillation counting method


J Med Chem 61: 9121-9131 (2018)


Article DOI: 10.1021/acs.jmedchem.8b00542
BindingDB Entry DOI: 10.7270/Q2KH0QZ9
More data for this
Ligand-Target Pair
5-hydroxytryptamine receptor 2A


(Homo sapiens (Human))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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7.40E+3n/an/an/an/an/an/an/an/a



Organix Inc

Curated by ChEMBL


Assay Description
Displacement of [125I]DOI from human 5HT2A receptor expressed in HEK293 cell membranes


J Med Chem 61: 9121-9131 (2018)


Article DOI: 10.1021/acs.jmedchem.8b00542
BindingDB Entry DOI: 10.7270/Q2KH0QZ9
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Homo sapiens (Human))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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1.95E+3n/an/an/an/an/an/an/an/a



Organix Inc

Curated by ChEMBL


Assay Description
Displacement of [3H](+)-syn-Ethyl 1-(2-(2,4-Dioxo-1,2-dihydroquinazolin-3(4H)-yl)ethyl)-4-(4-fluorophenyl)piperidine-3-carboxylate from human VMAT2 e...


J Med Chem 61: 9121-9131 (2018)


Article DOI: 10.1021/acs.jmedchem.8b00542
BindingDB Entry DOI: 10.7270/Q2KH0QZ9
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Rattus norvegicus (Rat))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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PubMed
470n/an/an/an/an/an/an/an/a



University of Arkansas for Medical Sciences

Curated by ChEMBL


Assay Description
Inhibition of [3H]DA uptake at VMAT2 in rat striatal synaptic vesicles


Medchemcomm 4: 564-568 (2013)


Article DOI: 10.1039/c3md20374c
BindingDB Entry DOI: 10.7270/Q2KD21VD
More data for this
Ligand-Target Pair
Synaptic vesicular amine transporter


(Rattus norvegicus (Rat))
BDBM50080818
PNG
((-)-lobeline | 2-(6-(2-Hydroxy-2-phenylethyl)-1-me...)
Show SMILES CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 |r|
Show InChI InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
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Similars

Article
PubMed
6.26E+3n/an/an/an/an/an/an/an/a



University of Kentucky

Curated by ChEMBL


Assay Description
Inhibition constant against [3H]-methyllycaconitine binding to vesicular monoamine transporter-2 of rat brain membranes


Bioorg Med Chem Lett 15: 4463-6 (2005)


Article DOI: 10.1016/j.bmcl.2005.07.032
BindingDB Entry DOI: 10.7270/Q2J38S3H
More data for this
Ligand-Target Pair