NP-MRD: Showing NP-Card for 2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone (NP0220511)

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Record Information

Version

2.0

Created at

2022-09-05 21:50:39 UTC

Updated at

2022-09-05 21:50:39 UTC

NP-MRD ID

NP0220511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone

Description

Lobeline, also known as lobeline sulfate or sulfate, lobeline, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. It also inhibits the reuptake of dopamine and serotonin, and acts as a mixed agonist–antagonist at nicotinic acetylcholine receptors to which it binds at the subunit interfaces of the extracellular domain. Analogous compounds, such as lobelane (a minor alkaloid found in the same plants) and its synthetic derivatives have similar biological effects with somewhat different relative affinities to VMAT and other proteins. Lobeline is a pyridine alkaloid found in a variety of plants, particularly those in the genus Lobelia, including Indian tobacco (Lobelia inflata), Devil's tobacco (Lobelia tupa), cardinal flower (Lobelia cardinalis), great lobelia (Lobelia siphilitica), Lobelia chinensis, and Hippobroma longiflora. Lobeline is a very strong basic compound (based on its pKa). Lobeline has a narrow therapeutic index; the potentially beneficial dose of lobeline is very close to the toxic dose. In its pure form, it is a white amorphous powder which is freely soluble in water. It seems to be a P-glycoprotein inhibitor, according to at least one study. Ingestion of lobeline may cause nausea, vomiting, diarrhea, coughing, dizziness, visual disturbances, hearing disturbances, mental confusion, weakness, slowed heart rate, increased blood pressure, increased breathing rate, tremors, and seizures. 2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone is found in Hippobroma longiflora and Lobelia inflata. It has been hypothesized that P-glycoprotein inhibition reduces chemotherapeutic resistance in cancer, presumably affecting any substrates of P-gp.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041407042D          

 28 30  0  0  1  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  8  1  0  0  0  0
 17  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  1  0  0  0
 20 14  1  0  0  0  0
 20 16  1  1  0  0  0
 21 15  1  0  0  0  0
 21 17  1  0  0  0  0
 22 16  1  0  0  0  0
 22 18  1  0  0  0  0
 23  1  1  0  0  0  0
 23 19  1  0  0  0  0
 23 20  1  0  0  0  0
 21 24  1  1  0  0  0
 25 22  2  0  0  0  0
 19 26  1  6  0  0  0
 20 27  1  6  0  0  0
 21 28  1  1  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    0.9392   -1.9626   -0.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772   -0.7883   -0.3160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1651   -0.9339   -0.5004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7850   -1.7821    0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2479   -1.8844    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7142   -2.7759   -0.4218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2243   -0.9984    1.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5627   -1.1362    0.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4614   -0.3021    1.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0295    0.6971    2.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6757    0.8306    2.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -0.0141    1.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3646   -1.4619   -1.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7960   -0.5622   -2.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709    0.2577   -2.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221    0.4072   -1.0673 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0433    0.8453   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197    1.0083    0.6704 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1492   -0.1211    1.4345 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485    1.4124    0.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7321    0.4525    0.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0695    0.7875    0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4223    2.1044    1.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4425    3.0594    1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1161    2.7141    1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9887   -2.0442   -0.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9955   -1.9551   -1.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4189   -2.8539   -0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6023    0.0827   -0.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3536   -2.8276    0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5717   -1.4166    1.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9581   -1.9048    0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5489   -0.4029    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7509    1.3590    2.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3251    1.6193    3.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356    0.1656    2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623   -2.5152   -1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4774   -1.6083   -2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -1.1978   -3.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399    0.1075   -3.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2774    1.2707   -3.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2824   -0.1903   -2.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0350    1.2111   -0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.1827   -1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1612    1.8489   -1.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    1.8015    1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254    0.0624    2.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4439   -0.5876    0.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8475    0.0350    0.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4841    2.3459    1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938    4.0951    1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196    3.4635    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  3  2  1  0
  2  1  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  2 16  1  0
 25 20  1  0
 12  7  1  0
 18 46  1  1
 19 47  1  0
 17 44  1  0
 17 45  1  0
 16 43  1  1
 15 41  1  0
 15 42  1  0
 14 39  1  0
 14 40  1  0
 13 37  1  0
 13 38  1  0
  3 29  1  6
  4 30  1  0
  4 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
M  END


  Mrv0541 05041407042D          

 28 30  0  0  1  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  8  1  0  0  0  0
 17  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  1  0  0  0
 20 14  1  0  0  0  0
 20 16  1  1  0  0  0
 21 15  1  0  0  0  0
 21 17  1  0  0  0  0
 22 16  1  0  0  0  0
 22 18  1  0  0  0  0
 23  1  1  0  0  0  0
 23 19  1  0  0  0  0
 23 20  1  0  0  0  0
 21 24  1  1  0  0  0
 25 22  2  0  0  0  0
 19 26  1  6  0  0  0
 20 27  1  6  0  0  0
 21 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0220511

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(C[C@@]1([H])CCC[C@@]([H])(CC(=O)C2=CC=CC=C2)N1C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
MXYUKLILVYORSK-QHAWAJNXSA-N

> <FORMULA>
C22H27NO2

> <MOLECULAR_WEIGHT>
337.4553

> <EXACT_MASS>
337.204179113

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.98568440365199

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S,6R)-6-[(2R)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethan-1-one

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
3.7834027453333317

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.998159116300062

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.42222242568753

> <JCHEM_PKA_STRONGEST_BASIC>
8.771676927729155

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
101.51209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2S,6R)-6-[(2R)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   23                                                            
CONECT    2    4    5                                                       
CONECT    3    6    7                                                       
CONECT    4    2    9                                                       
CONECT    5    2   10                                                       
CONECT    6    3   11                                                       
CONECT    7    3   12                                                       
CONECT    8   13   14                                                       
CONECT    9    4   17                                                       
CONECT   10    5   17                                                       
CONECT   11    6   18                                                       
CONECT   12    7   18                                                       
CONECT   13    8   19                                                       
CONECT   14    8   20                                                       
CONECT   15   19   21                                                       
CONECT   16   20   22                                                       
CONECT   17    9   10   21                                                  
CONECT   18   11   12   22                                                  
CONECT   19   13   15   23   26                                             
CONECT   20   14   16   23   27                                             
CONECT   21   15   17   24   28                                             
CONECT   22   16   18   25                                                  
CONECT   23    1   19   20                                                  
CONECT   24   21                                                            
CONECT   25   22                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   21                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
Lobeline sulfate	MeSH
Sulfate, lobeline	MeSH
Smokeless	MeSH
Inibsa brand OF lobelin sulfate	MeSH

Chemical Formula

C₂₂H₂₇NO₂

Average Mass

337.4553 Da

Monoisotopic Mass

337.20418 Da

IUPAC Name

2-[(2S,6R)-6-[(2R)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethan-1-one

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(C[C@@]1([H])CCC[C@@]([H])(CC(=O)C2=CC=CC=C2)N1C)C1=CC=CC=C1

InChI Identifier

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

InChI Key

MXYUKLILVYORSK-QHAWAJNXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hippobroma longiflora	LOTUS Database	35616633
Lobelia inflata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Benzoyl
Aryl alkyl ketone
Aralkylamine
Monocyclic benzene moiety
Beta-aminoketone
Piperidine
Benzenoid
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Organoheterocyclic compound
Azacycle
Aromatic alcohol
Amine
Organonitrogen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.73	ALOGPS
logP	3.78	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	101.51 m³·mol⁻¹	ChemAxon
Polarizability	37.99 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lobeline

METLIN ID

Not Available

PubChem Compound

5288703

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone (NP0220511)

MOL for NP0220511 (2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone)

3D MOL for NP0220511 (2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone)

3D SDF for NP0220511 (2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone)

3D-SDF for NP0220511 (2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone)

PDB for NP0220511 (2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone)

3D PDB for NP0220511 (2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone)

SMILES for NP0220511 (2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone)

INCHI for NP0220511 (2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone)

Structure for NP0220511 (2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone)

3D Structure for NP0220511 (2-[(2s,6r)-6-[(2r)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone)