UCSF

ZINC00001624

Draw Identity 99% 90% 80% 70%

Substance Information

In ZINC since Heavy atoms Benign functionality
September 30th, 2005 25 Yes

Popular Name: lobeline hydrochloride lobeline hydrochloride

Find On: PubMed — Wikipedia — Google

CAS Numbers: 134-63-4 , 134-63-4, 90-69-7 [lobeli , 134-63-4; 98-96-4 , 134-64-5 , 90-69-7 , [134-63-4]

Other Names:

(-)-lobeline

(-)-Lobeline HCl

(-)-Lobeline Hydrochloride

(-)-Lobeline; 90-69-7; C07475; Lobeline

134-64-5; D08138; Lobeline sulfate; Smokeless (TN)

2-(6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone; 2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone; 8,10-Diphenyllobelionol; Lobelin; Lobnico; alpha-Lobeline

2-(6-(2-Hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone hydrochloride

2-(6-(2-Hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone sulfate

2-(6-(2-Hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanonehydrochloride

2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone hydrochloride; Acetophenone, 2-(6-(beta-hydroxyphenethyl)-1-methyl-2-piperidyl)-, hydrochloride; Ethanone, 2-(6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, hydrochloride; HSDB

90-69-7; D02364; Lobeline (INN)

a-Lobeline Hydrochloride [134-63-4]

alpha-LOBELINE HYDROCHLORIDE; [134-63-4]

alpha-Lobelinehydrochloride

Bantron; C22H27NO2.H2O4S; EINECS 205-151-8; Ethanone, 2-(6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, (2theta-(2alpha,6alpha(S)))-, sulfate (2:1) (salt); LS-88109; Lobelin sulfate; Lobeline sulfate; Lobeline sulphate; Lobeline, sulfate (

BRD-K66206289-003-03-1

CHEBI:43901; CHEBI:6509

CPD000058465; LOBELINE HYDROCHLORIDE

CPD000058465; LOBELINE HYDROCHLORIDE; Lobeline; SAM001247050

CPD000058465; LOBELINE HYDROCHLORIDE; SAM001247050

Ethanone, 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenyl-, hydrochloride (1:1)

Inflatine

Lobelina; Lobelinum

Lobeline

Lobeline (hydrochloride)

Lobeline HCl

Lobeline sulfate

Lobeline sulfate, 99%

MFCD00082455

MFCD00135592

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 3.73 10.48 -45.25 2 3 1 42 338.471 6 ↓
Hi High (pH 8-9.5) 3.73 8.25 -8.89 1 3 0 41 337.463 6 ↓

Vendor Notes

Note Type Comments Provided By
MP 182-185o C Indofine
MP 183-185 °C (dec.)(lit.) Indofine
Therapy antiasthmatic, respiratory stimulant SMDC MicroSource
Target Bcl-2-like protein 1(Q07817)&Bcl-2-related protein A1(Q16548) Herbal Ingredients Targets
UniProt Database Links GR33A_DROME ChEBI
SOLUBILITY H2O: 25 mg/mL Indofine
PUBCHEM_SUBSTANCE_COMMENT NCC_SAMPLE_SUPPLIER : Tocris Cookson Ltd.; NCC_SUPPLIER_STRUCTURE_ID : 100344; 1 hydrogen chloride NIH Clinical Collection via PubChem
PUBCHEM_SUBSTANCE_COMMENT SAMPLE_SUPPLIER: Tocris Bioscience; SUPPLIER_STRUCTURE_ID: 100344; SALT: 1 hydrogen chloride NIH Clinical Collection via PubChem

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
ACH10-2-E Neuronal Acetylcholine Receptor Protein Alpha-10 Subunit (cluster #2 Of 4), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHA-2-E Acetylcholine Receptor Protein Alpha Chain (cluster #2 Of 4), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHA2-5-E Neuronal Acetylcholine Receptor Protein Alpha-2 Subunit (cluster #5 Of 6), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHA3-3-E Neuronal Acetylcholine Receptor Protein Alpha-3 Subunit (cluster #3 Of 5), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHA4-1-E Neuronal Acetylcholine Receptor Protein Alpha-4 Subunit (cluster #1 Of 5), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHA5-3-E Neuronal Acetylcholine Receptor Protein Alpha-5 Subunit (cluster #3 Of 4), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHA6-3-E Neuronal Acetylcholine Receptor Subunit Alpha-6 (cluster #3 Of 4), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHA7-6-E Neuronal Acetylcholine Receptor Protein Alpha-7 Subunit (cluster #6 Of 6), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHA7-6-E Neuronal Acetylcholine Receptor Protein Alpha-7 Subunit (cluster #6 Of 6), Eukaryotic Eukaryotes 6260 0.29 Binding ≤ 10μM
ACHA9-3-E Neuronal Acetylcholine Receptor Protein Alpha-9 Subunit (cluster #3 Of 4), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHB-1-E Acetylcholine Receptor Protein Beta Chain (cluster #1 Of 4), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHB2-5-E Neuronal Acetylcholine Receptor Protein Beta-2 Subunit (cluster #5 Of 7), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHB3-3-E Neuronal Acetylcholine Receptor Subunit Beta-3 (cluster #3 Of 4), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
ACHB4-2-E Neuronal Acetylcholine Receptor Subunit Beta-4 (cluster #2 Of 7), Eukaryotic Eukaryotes 87 0.40 Binding ≤ 10μM
VMAT2-1-E Synaptic Vesicular Amine Transporter (cluster #1 Of 2), Eukaryotic Eukaryotes 2760 0.31 Binding ≤ 10μM
VMAT2-1-E Synaptic Vesicular Amine Transporter (cluster #1 Of 2), Eukaryotic Eukaryotes 6260 0.29 Binding ≤ 10μM
CP2D6-3-E Cytochrome P450 2D6 (cluster #3 Of 3), Eukaryotic Eukaryotes 120 0.39 ADME/T ≤ 10μM
Z104290-1-O Neuronal Acetylcholine Receptor; Alpha4/beta2 (cluster #1 Of 4), Other Other 4 0.47 Binding ≤ 10μM
Z104290-1-O Neuronal Acetylcholine Receptor; Alpha4/beta2 (cluster #1 Of 4), Other Other 40 0.41 Binding ≤ 10μM
Z50425-3-O Plasmodium Falciparum (cluster #3 Of 22), Other Other 3981 0.30 Functional ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
ACHA_RAT P25108 Acetylcholine Receptor Protein Alpha Chain, Rat 4 0.47 Binding ≤ 1μM
ACHB_RAT P25109 Acetylcholine Receptor Protein Beta Chain, Rat 4 0.47 Binding ≤ 1μM
ACH10_RAT Q9JLB5 Neuronal Acetylcholine Receptor Protein Alpha-10 Subunit, Rat 4 0.47 Binding ≤ 1μM
ACHA2_RAT P12389 Neuronal Acetylcholine Receptor Protein Alpha-2 Subunit, Rat 4 0.47 Binding ≤ 1μM
ACHA3_RAT P04757 Neuronal Acetylcholine Receptor Protein Alpha-3 Subunit, Rat 4 0.47 Binding ≤ 1μM
ACHA4_RAT P09483 Neuronal Acetylcholine Receptor Protein Alpha-4 Subunit, Rat 4 0.47 Binding ≤ 1μM
ACHA5_RAT P20420 Neuronal Acetylcholine Receptor Protein Alpha-5 Subunit, Rat 4 0.47 Binding ≤ 1μM
ACHA6_RAT P43143 Neuronal Acetylcholine Receptor Protein Alpha-6 Subunit, Rat 4 0.47 Binding ≤ 1μM
ACHA7_RAT Q05941 Neuronal Acetylcholine Receptor Protein Alpha-7 Subunit, Rat 4 0.47 Binding ≤ 1μM
ACHA9_RAT P43144 Neuronal Acetylcholine Receptor Protein Alpha-9 Subunit, Rat 4 0.47 Binding ≤ 1μM
ACHB2_RAT P12390 Neuronal Acetylcholine Receptor Protein Beta-2 Subunit, Rat 4 0.47 Binding ≤ 1μM
ACHB3_RAT P12391 Neuronal Acetylcholine Receptor Protein Beta-3 Subunit, Rat 4 0.47 Binding ≤ 1μM
ACHB4_RAT P12392 Neuronal Acetylcholine Receptor Protein Beta-4 Subunit, Rat 4 0.47 Binding ≤ 1μM
Z104290 Z104290 Neuronal Acetylcholine Receptor; Alpha4/beta2 40 0.41 Binding ≤ 1μM
VMAT2_RAT Q01827 Synaptic Vesicular Amine Transporter, Rat 4 0.47 Binding ≤ 1μM
ACHA_RAT P25108 Acetylcholine Receptor Protein Alpha Chain, Rat 4 0.47 Binding ≤ 10μM
ACHB_RAT P25109 Acetylcholine Receptor Protein Beta Chain, Rat 4 0.47 Binding ≤ 10μM
ACH10_RAT Q9JLB5 Neuronal Acetylcholine Receptor Protein Alpha-10 Subunit, Rat 4 0.47 Binding ≤ 10μM
ACHA2_RAT P12389 Neuronal Acetylcholine Receptor Protein Alpha-2 Subunit, Rat 4 0.47 Binding ≤ 10μM
ACHA3_RAT P04757 Neuronal Acetylcholine Receptor Protein Alpha-3 Subunit, Rat 4 0.47 Binding ≤ 10μM
ACHA4_RAT P09483 Neuronal Acetylcholine Receptor Protein Alpha-4 Subunit, Rat 4 0.47 Binding ≤ 10μM
ACHA5_RAT P20420 Neuronal Acetylcholine Receptor Protein Alpha-5 Subunit, Rat 4 0.47 Binding ≤ 10μM
ACHA6_RAT P43143 Neuronal Acetylcholine Receptor Protein Alpha-6 Subunit, Rat 4 0.47 Binding ≤ 10μM
ACHA7_RAT Q05941 Neuronal Acetylcholine Receptor Protein Alpha-7 Subunit, Rat 4 0.47 Binding ≤ 10μM
ACHA9_RAT P43144 Neuronal Acetylcholine Receptor Protein Alpha-9 Subunit, Rat 4 0.47 Binding ≤ 10μM
ACHB2_RAT P12390 Neuronal Acetylcholine Receptor Protein Beta-2 Subunit, Rat 4 0.47 Binding ≤ 10μM
ACHB3_RAT P12391 Neuronal Acetylcholine Receptor Protein Beta-3 Subunit, Rat 4 0.47 Binding ≤ 10μM
ACHB4_RAT P12392 Neuronal Acetylcholine Receptor Protein Beta-4 Subunit, Rat 4 0.47 Binding ≤ 10μM
Z104290 Z104290 Neuronal Acetylcholine Receptor; Alpha4/beta2 40 0.41 Binding ≤ 10μM
VMAT2_HUMAN Q05940 Synaptic Vesicular Amine Transporter, Human 2760 0.31 Binding ≤ 10μM
VMAT2_RAT Q01827 Synaptic Vesicular Amine Transporter, Rat 2760 0.31 Binding ≤ 10μM
Z50425 Z50425 Plasmodium Falciparum 10000 0.28 Functional ≤ 10μM
CP2D6_HUMAN P10635 Cytochrome P450 2D6, Human 120 0.39 ADME/T ≤ 10μM

Reactome Annotations from Targets (via Uniprot)

Description Species
CYP2E1 reactions
Dopamine Neurotransmitter Release Cycle
Fatty acids
Highly calcium permeable nicotinic acetylcholine receptors
Highly calcium permeable postsynaptic nicotinic acetylcholine receptors
Highly sodium permeable acetylcholine nicotinic receptors
Miscellaneous substrates
Na+/Cl- dependent neurotransmitter transporters
Norepinephrine Neurotransmitter Release Cycle
Serotonin Neurotransmitter Release Cycle
Xenobiotics

Analogs ( Draw Identity 99% 90% 80% 70% )