CHEBI:48723 - (−)-lobeline

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ChEBI Name (−)-lobeline
ChEBI ID CHEBI:48723
ChEBI ASCII Name (-)-lobeline
Definition An optically active piperidine alkaloid having a 2-oxo-2-phenylethyl substituent at the 2-position and a 2-hydroxy-2-phenylethyl group at the 6-position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43901, CHEBI:6509
Supplier Information
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Formula C22H27NO2
Net Charge 0
Average Mass 337.45530
Monoisotopic Mass 337.20418
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
InChIKey MXYUKLILVYORSK-HBMCJLEFSA-N
SMILES [H][C@]1(CCC[C@]([H])(CC(=O)c2ccccc2)N1C)C[C@H](O)c1ccccc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): nicotinic acetylcholine receptor agonist
An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): nicotinic acetylcholine receptor agonist
An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-lobeline (CHEBI:48723) has role nicotinic acetylcholine receptor agonist (CHEBI:47958)
(−)-lobeline (CHEBI:48723) is a aromatic ketone (CHEBI:76224)
(−)-lobeline (CHEBI:48723) is a piperidine alkaloid (CHEBI:26147)
(−)-lobeline (CHEBI:48723) is a tertiary amine (CHEBI:32876)
IUPAC Name
2-{(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethanone
INNs Sources
Lobelina ChemIDplus
Lobelinum ChemIDplus
Synonyms Sources
(-)-Lobeline KEGG COMPOUND
2-(6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone ChemIDplus
2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone ChemIDplus
8,10-Diphenyllobelionol ChemIDplus
α-Lobeline NIST Chemistry WebBook
Lobelin ChemIDplus
Lobeline KEGG COMPOUND
LOBELINE PDBeChem
Lobnico NIST Chemistry WebBook
Brand Name Source
Inflatine ChemIDplus
Manual Xrefs Databases
C00002053 KNApSAcK
C07475 KEGG COMPOUND
D02364 KEGG DRUG
L0B PDBeChem
LSM-5744 LINCS
View more database links
Registry Numbers Types Sources
90-69-7 CAS Registry Number KEGG COMPOUND
90-69-7 CAS Registry Number NIST Chemistry WebBook
90-69-7 CAS Registry Number ChemIDplus
91532 Beilstein Registry Number Beilstein
Last Modified
25 November 2019