2-[6-(2-Hydroxy-2-phenyl-ethyl)-1-methyl-piperidin-2-yl]-1-phenyl-ethanone (lobeline)

ID: ALA2103769

Chembl Id: CHEMBL2103769

Cas Number: 90-69-7

PubChem CID: 736282

Max Phase: Preclinical

Molecular Formula: C22H27NO2

Molecular Weight: 337.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard 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+/m1/s1

Standard InChI Key:  MXYUKLILVYORSK-HKBOAZHASA-N

Alternative Forms

1. Parent:

   

   ALA2103769

   LOBELINE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 337.46

Molecular Weight (Monoisotopic): 337.2042

AlogP: 4.24

#Rotatable Bonds: 6

Polar Surface Area: 40.54

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.77

CX LogP: 3.78

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.80

Np Likeness Score: 0.51

References

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2. Sloan JW, Martin WR, Hook R, Hernandez J..  (1985)  Structure-activity relationships of some pyridine, piperidine, and pyrrolidine analogues for enhancing and inhibiting the binding of (+/-)-[3H]nicotine to the rat brain P2 preparation.,  28  (9): [PMID:4032427] [10.1021/jm00147a021]

3. Zheng G, Horton DB, Deaciuc AG, Dwoskin LP, Crooks PA..  (2006)  Des-keto lobeline analogs with increased potency and selectivity at dopamine and serotonin transporters.,  16  (19): [PMID:16905316] [10.1016/j.bmcl.2006.07.070]

4. Vartak AP, Nickell JR, Chagkutip J, Dwoskin LP, Crooks PA..  (2009)  Pyrrolidine analogues of lobelane: relationship of affinity for the dihydrotetrabenazine binding site with function of the vesicular monoamine transporter 2 (VMAT2).,  52  (23): [PMID:19691331] [10.1021/jm900770h]

5. Hojahmat M, Horton DB, Norrholm SD, Miller DK, Grinevich VP, Deaciuc AG, Dwoskin LP, Crooks PA..  (2010)  Lobeline esters as novel ligands for neuronal nicotinic acetylcholine receptors and neurotransmitter transporters.,  18  (2): [PMID:20036131] [10.1016/j.bmc.2009.12.002]

6. PubChem BioAssay data set, 

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9. TOMIZAWA M, YAMAMOTO I.  (1992)  Binding of Nicotinoids and the Related Compounds to the Insect Nicotinic Acetyicholine Receptor,  17  (4): [10.1584/jpestics.17.4_231]

10. TOMIZAWA M, OTSUKA H, MIYAMOTO T, YAMAMOTO I.  (1995)  Pharmacological Effects of Imidacloprid and Its Related Compounds on the Nicotinic Acetyicholine Receptor with Its Ion Channel from the Torpedo Electric Organ,  20  (1): [10.1584/jpestics.20.49]

11. TOMIZAWA M, OTSUKA H, MIYAMOTO T, ELDEFRAWI ME, YAMAMOTO I.  (1995)  Pharmacological Characteristics of Insect Nicotinic Acetyicholine Receptor with Its Ion Channel and the Comparison of the Effect of Nicotinoids and Neonicotinoids,  20  (1): [10.1584/jpestics.20.57]

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13. Bach TB, Jensen AA, Petersen JG, Sørensen TE, Della Volpe S, Liu J, Blaazer AR, van Muijlwijk-Koezen JE, Balle T, Frølund B..  (2015)  Exploration of the molecular architecture of the orthosteric binding site in the α4β2 nicotinic acetylcholine receptor with analogs of 3-(dimethylamino)butyl dimethylcarbamate (DMABC) and 1-(pyridin-3-yl)-1,4-diazepane.,  102  [PMID:26301559] [10.1016/j.ejmech.2015.07.024]

14. Wasilewicz A, Kirchweger B, Bojkova D, Abi Saad MJ, Langeder J, Bütikofer M, Adelsberger S, Grienke U, Cinatl J, Petermann O, Scapozza L, Orts J, Kirchmair J, Rabenau HF, Rollinger JM..  (2023)  Identification of Natural Products Inhibiting SARS-CoV-2 by Targeting Viral Proteases: A Combined in Silico and in Vitro Approach.,  86  (2.0): [PMID:36651644] [10.1021/acs.jnatprod.2c00843]

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Source

Source(2):

• Scientific Literature
• PubChem BioAssays