Navigation

name Structure Reference Source Properties Activities Metabolism

(-)-lobeline

AlkaPlorer ID: AK002663

Synonym: '(-)-Lobeline', '8,10-Diphenyllobelionol', '2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone', 'MLS000536557', 'LOBELINE', 'MLS006011485', 'Lobeline', 'Lobelin', 'lobeline', 'SMR000151480', 'Lobnico', 'Inflatine', 'alpha-Lobeline', '2-(6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone'

IUPAC Name: 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone

Structure

SMILES: CN1[C@@H](CC(=O)C2=CC=CC=C2)CCC[C@H]1C[C@H](O)C1=CC=CC=C1

copy

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

copy

InChIKey: MXYUKLILVYORSK-HBMCJLEFSA-N

copy

Reference

Über die Alkaloide der Lobelia‐Pflanze. I

PubChem CID: 101616

CAS: 6299-05-4

LOTUS: LTS0073840

SuperNatural Ⅲ: SN0238374-01

NPASS: NPC285394

data_source: manually

Properties Information

Molecule Weight: 337.463

TPSA？: 40.540000000000006

MolLogP？: 4.236000000000003

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Aplysia californica Soluble acetylcholine receptor Ki 2.512 nM 10.1016/j.bmcl.2011.12.008
Homo sapiens Arachidonate 15-lipoxygenase, type II Potency 35481.3 nM None
Homo sapiens Ataxin-2 Potency 22387.2 nM None
Homo sapiens Ataxin-2 Potency 28183.8 nM None
Homo sapiens Cerebroside-sulfatase Potency 47.8 nM None
Homo sapiens HEK293 Potency 3262.9 nM None
Homo sapiens Histone deacetylase 6 Inhibition -9.37 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 18.77 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 25118.9 nM None
Homo sapiens Neuronal acetylcholine receptor; alpha4/beta2 Ki 5.012 nM 10.1016/j.bmcl.2011.12.008
Homo sapiens Neuronal acetylcholine receptor protein alpha-7 subunit Ki 7943.28 nM 10.1016/j.bmcl.2011.12.008
Homo sapiens Prelamin-A/C Potency 631.0 nM None
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki 7400.0 nM 10.1021/acs.jmedchem.8b00542
Homo sapiens SH-SY5Y Potency 28183.8 nM None
Homo sapiens Synaptic vesicular amine transporter IC50 4200.0 nM 10.1021/acs.jmedchem.8b00542
Homo sapiens Synaptic vesicular amine transporter Ki 1840.0 nM 10.1021/acs.jmedchem.8b00542
Homo sapiens Synaptic vesicular amine transporter Ki 1950.0 nM 10.1021/acs.jmedchem.8b00542
Homo sapiens Synaptic vesicular amine transporter Ki 10000.0 nM 10.1021/acs.jmedchem.8b00542
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 20596.2 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 23715.0 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 29092.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 29855.4 nM None
Lymnaea stagnalis Acetylcholine-binding protein Ki 630.96 nM 10.1016/j.bmcl.2011.12.008
Mus musculus Synaptic vesicular amine transporter IC50 381.0 nM 10.1021/acs.jmedchem.8b00542
Plasmodium falciparum Plasmodium falciparum Potency 13459.1 nM None
Plasmodium falciparum Plasmodium falciparum Potency 16944.1 nM None
Rattus norvegicus Neuronal acetylcholine receptor IC50 87.0 nM 10.1016/s0960-894x(03)00728-5
Rattus norvegicus Neuronal acetylcholine receptor IC50 18100.0 nM 10.1016/s0960-894x(03)00728-5
Rattus norvegicus Neuronal acetylcholine receptor Ki 4.0 nM 10.1021/jm990286m
Rattus norvegicus Neuronal acetylcholine receptor; alpha4/beta2 Ki 40.0 nM 10.1021/jm0501228
Rattus norvegicus Neuronal acetylcholine receptor protein alpha-7 subunit Ki 6260.0 nM 10.1021/jm0501228
Rattus norvegicus Synaptic vesicular amine transporter Ki 4.0 nM 10.1016/j.bmcl.2005.07.032
Rattus norvegicus Synaptic vesicular amine transporter Ki 470.0 nM 10.1039/c3md20374c
Rattus norvegicus Synaptic vesicular amine transporter Ki 2760.0 nM 10.1016/j.bmcl.2005.07.032
Rattus norvegicus Synaptic vesicular amine transporter Ki 2760.0 nM 10.1016/j.bmcl.2008.10.042
Rattus norvegicus Synaptic vesicular amine transporter Ki 2760.0 nM 10.1021/jm0501228
Rattus norvegicus Synaptic vesicular amine transporter Ki 2760.0 nM 10.1039/c3md20374c
Rattus norvegicus Synaptic vesicular amine transporter Ki 6260.0 nM 10.1016/j.bmcl.2005.07.032
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 631.0 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 3.19 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.19 % 10.6019/CHEMBL4495565
Trypanosoma brucei 6-phospho-1-fructokinase Potency 8492.1 nM None
None ADMET T1/2 0.8333 hr 10.1016/j.bmcl.2017.10.039
None Unchecked Activity 50.0 % 10.1021/jm301557k
None Unchecked Ki ratio 0.001 None 10.1021/jm0501228
None Unchecked Ki ratio 2.3 None 10.1021/jm0501228
None Unchecked Potency 5623.4 nM None
None Unchecked Potency 23099.9 nM None
None Unchecked Potency 25118.9 nM None
None Unchecked Potency 28183.8 nM None
None Unchecked Potency 31622.8 nM None
None Unchecked Potency 35481.3 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010590 CN1[C@H](CC(=O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1>>CN1[C@H](C[C@H](O)c2ccccc2)CCC[C@@H]1CC(=O)c1ccccc1 R08424