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InChI=1S/CH4O/c1-2/h2H,1H3
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> Main
CHEBI:48723 - (−)-lobeline
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ChEBI Ontology
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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 (Br
o
nsted 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-
{(2
R
,6
S
)-
6-
[(2
S
)-
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