NP-MRD: Showing NP-Card for lobeline (NP0034231)

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Record Information

Version

2.0

Created at

2021-06-20 18:01:12 UTC

Updated at

2021-08-20 00:00:29 UTC

NP-MRD ID

NP0034231

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lobeline

Provided By

JEOL Database JEOL Logo

Description

Lobeline is also known as alpha-lobeline or lobelinum. Lobeline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. lobeline is found in ampanula medium and Lobelia siphilitica. lobeline was first documented in 2020 (PMID: 33111502). Based on a literature review a small amount of articles have been published on Lobeline (PMID: 33897801) (PMID: 34298167) (PMID: 33762957) (PMID: 32186243).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120013D          

 52 54  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202120013D          

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   -1.2158   -1.2870    2.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3524   -1.7708    5.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294   -2.9549    7.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2970   -3.1948    7.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1056   -2.2323    6.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5543   -1.0313    4.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0  0  0  0
 15 14  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 17  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 13  3  1  0  0  0  0
  7  5  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
  7  8  2  0  0  0  0
 13 14  1  0  0  0  0
  8  9  1  0  0  0  0
  3  4  1  0  0  0  0
  9 10  2  0  0  0  0
  4  5  1  0  0  0  0
 10 11  1  0  0  0  0
  3  2  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  2 16  1  0  0  0  0
 18 19  2  0  0  0  0
 25 20  1  0  0  0  0
  2  1  1  0  0  0  0
 16 15  1  0  0  0  0
  5  6  1  0  0  0  0
 13 39  1  0  0  0  0
 13 40  1  0  0  0  0
  3 29  1  6  0  0  0
 16 45  1  6  0  0  0
 15 43  1  0  0  0  0
 15 44  1  0  0  0  0
 14 41  1  0  0  0  0
 14 42  1  0  0  0  0
 17 46  1  0  0  0  0
 17 47  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
 25 52  1  0  0  0  0
 21 48  1  0  0  0  0
 22 49  1  0  0  0  0
 23 50  1  0  0  0  0
 24 51  1  0  0  0  0
  5 32  1  1  0  0  0
  8 34  1  0  0  0  0
  9 35  1  0  0  0  0
 10 36  1  0  0  0  0
 11 37  1  0  0  0  0
 12 38  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  6 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034231

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])[C@@]1([H])N(C([H])([H])[H])[C@@]([H])(C([H])([H])C(=O)C2=C([H])C([H])=C([H])C([H])=C2[H])C([H])([H])C([H])([H])C1([H])[H]

> <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-/m0/s1

> <INCHI_KEY>
MXYUKLILVYORSK-HBMCJLEFSA-N

> <FORMULA>
C22H27NO2

> <MOLECULAR_WEIGHT>
337.4553

> <EXACT_MASS>
337.204179113

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.265079612139125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2R,6S)-6-[(2S)-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>
8.771676927729146

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
101.51210000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-lobeline

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    0.9244    0.7781    2.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    0.4270    1.1220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1196    1.1670   -0.1661 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1920    0.9940   -0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5563   -0.4650   -1.2647 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8543   -0.4815   -1.8743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706   -1.1637   -2.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065   -2.1279   -1.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -2.7683   -2.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2848   -2.4520   -3.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4233   -1.4923   -4.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4974   -0.8496   -3.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408    2.6638    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855    2.8626    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959    2.0279    1.9823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5230    0.5525    1.7233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6782   -0.3072    2.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1294   -0.5653    3.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0715   -0.1976    2.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148   -1.3021    4.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996   -1.8505    5.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -2.5293    6.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0508   -2.6655    7.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0666   -2.1257    6.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7506   -1.4473    5.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    0.5869    1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049    0.1462    2.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013    1.8223    2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9155    0.7522   -0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0279    1.4746   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1120    1.5486   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629   -1.0316   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377   -1.3403   -2.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -2.3744   -0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072   -3.5092   -2.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0050   -2.9492   -4.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707   -1.2408   -5.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -0.0974   -3.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4716    3.1605   -0.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485    3.1624    0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    2.5739    0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334    3.9229    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    2.4579    2.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9213    2.1060    2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284    0.1531    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1836    0.1839    3.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158   -1.2870    2.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3524   -1.7708    5.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294   -2.9549    7.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2970   -3.1948    7.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1056   -2.2323    6.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5543   -1.0313    4.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0
 15 14  1  0
 21 22  1  0
 22 23  2  0
 16 17  1  0
 23 24  1  0
 24 25  2  0
 13  3  1  0
  7  5  1  0
 17 18  1  0
 18 20  1  0
  7  8  2  0
 13 14  1  0
  8  9  1  0
  3  4  1  0
  9 10  2  0
  4  5  1  0
 10 11  1  0
  3  2  1  0
 11 12  2  0
 12  7  1  0
  2 16  1  0
 18 19  2  0
 25 20  1  0
  2  1  1  0
 16 15  1  0
  5  6  1  0
 13 39  1  0
 13 40  1  0
  3 29  1  6
 16 45  1  6
 15 43  1  0
 15 44  1  0
 14 41  1  0
 14 42  1  0
 17 46  1  0
 17 47  1  0
  4 30  1  0
  4 31  1  0
 25 52  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
  5 32  1  1
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 33  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.924   0.778   2.040  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.163   0.427   1.122  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.120   1.167  -0.166  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.192   0.994  -0.962  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.556  -0.465  -1.265  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.854  -0.482  -1.874  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.571  -1.164  -2.179  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.307  -2.128  -1.661  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.228  -2.768  -2.491  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.285  -2.452  -3.847  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.423  -1.492  -4.374  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.497  -0.850  -3.545  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.441   2.664   0.016  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.786   2.863   0.709  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.896   2.028   1.982  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.523   0.553   1.723  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.678  -0.307   2.994  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.129  -0.565   3.372  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.072  -0.198   2.672  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.415  -1.302   4.642  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.400  -1.851   5.437  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.720  -2.529   6.616  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.051  -2.666   7.008  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.067  -2.126   6.222  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.751  -1.447   5.043  0.00  0.00           C+0
HETATM   26  H   UNK     0       1.903   0.587   1.588  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.905   0.146   2.933  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.901   1.822   2.364  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.916   0.752  -0.800  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.028   1.475  -0.437  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.112   1.549  -1.907  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.663  -1.032  -0.333  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.938  -1.340  -2.324  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.286  -2.374  -0.601  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.907  -3.509  -2.077  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.005  -2.949  -4.491  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.471  -1.241  -5.430  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.161  -0.097  -3.968  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.472   3.160  -0.962  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.349   3.162   0.591  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.590   2.574   0.021  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.933   3.923   0.942  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.252   2.458   2.759  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.921   2.106   2.360  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.228   0.153   0.981  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.184   0.184   3.840  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.216  -1.287   2.821  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.352  -1.771   5.161  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.929  -2.955   7.230  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.297  -3.195   7.926  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.106  -2.232   6.524  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.554  -1.031   4.438  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3   16    1                                                  
CONECT    3   13    4    2   29                                             
CONECT    4    3    5   30   31                                             
CONECT    5    7    4    6   32                                             
CONECT    6    5   33                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9   34                                                  
CONECT    9    8   10   35                                                  
CONECT   10    9   11   36                                                  
CONECT   11   10   12   37                                                  
CONECT   12   11    7   38                                                  
CONECT   13    3   14   39   40                                             
CONECT   14   15   13   41   42                                             
CONECT   15   14   16   43   44                                             
CONECT   16   17    2   15   45                                             
CONECT   17   16   18   46   47                                             
CONECT   18   17   20   19                                                  
CONECT   19   18                                                            
CONECT   20   21   18   25                                                  
CONECT   21   20   22   48                                                  
CONECT   22   21   23   49                                                  
CONECT   23   22   24   50                                                  
CONECT   24   23   25   51                                                  
CONECT   25   24   20   52                                                  
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  108    0
END

RDKit          3D

52 54  0  0  0  0  0  0  0  0999 V2000
    0.9244    0.7781    2.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    0.4270    1.1220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1196    1.1670   -0.1661 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1920    0.9940   -0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5563   -0.4650   -1.2647 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8543   -0.4815   -1.8743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706   -1.1637   -2.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065   -2.1279   -1.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -2.7683   -2.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2848   -2.4520   -3.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4233   -1.4923   -4.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4974   -0.8496   -3.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408    2.6638    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855    2.8626    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959    2.0279    1.9823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5230    0.5525    1.7233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6782   -0.3072    2.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1294   -0.5653    3.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0715   -0.1976    2.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148   -1.3021    4.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996   -1.8505    5.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -2.5293    6.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0508   -2.6655    7.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0666   -2.1257    6.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7506   -1.4473    5.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025    0.5869    1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049    0.1462    2.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013    1.8223    2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9155    0.7522   -0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0279    1.4746   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1120    1.5486   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629   -1.0316   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377   -1.3403   -2.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2862   -2.3744   -0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072   -3.5092   -2.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0050   -2.9492   -4.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707   -1.2408   -5.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -0.0974   -3.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4716    3.1605   -0.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485    3.1624    0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    2.5739    0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334    3.9229    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    2.4579    2.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9213    2.1060    2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284    0.1531    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1836    0.1839    3.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158   -1.2870    2.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3524   -1.7708    5.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294   -2.9549    7.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2970   -3.1948    7.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1056   -2.2323    6.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5543   -1.0313    4.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0
 15 14  1  0
 21 22  1  0
 22 23  2  0
 16 17  1  0
 23 24  1  0
 24 25  2  0
 13  3  1  0
  7  5  1  0
 17 18  1  0
 18 20  1  0
  7  8  2  0
 13 14  1  0
  8  9  1  0
  3  4  1  0
  9 10  2  0
  4  5  1  0
 10 11  1  0
  3  2  1  0
 11 12  2  0
 12  7  1  0
  2 16  1  0
 18 19  2  0
 25 20  1  0
  2  1  1  0
 16 15  1  0
  5  6  1  0
 13 39  1  0
 13 40  1  0
  3 29  1  6
 16 45  1  6
 15 43  1  0
 15 44  1  0
 14 41  1  0
 14 42  1  0
 17 46  1  0
 17 47  1  0
  4 30  1  0
  4 31  1  0
 25 52  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
  5 32  1  1
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-(6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone	ChEBI
2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone	ChEBI
8,10-Diphenyllobelionol	ChEBI
alpha-Lobeline	ChEBI
Lobelin	ChEBI
Lobelina	ChEBI
Lobelinum	ChEBI
Lobnico	ChEBI
(-)-Lobeline	Kegg
2-(6-(b-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone	Generator
2-(6-(Β-hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone	Generator
a-Lobeline	Generator
Α-lobeline	Generator
Sulfate, lobeline	MeSH
Lobeline sulfate	MeSH
Smokeless	MeSH
Inibsa brand OF lobelin sulfate	MeSH
Lobeline	ChEBI

Chemical Formula

C₂₂H₂₇NO₂

Average Mass

337.4553 Da

Monoisotopic Mass

337.20418 Da

IUPAC Name

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

Traditional Name

(-)-lobeline

CAS Registry Number

Not Available

SMILES

[H]O[C@]([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])[C@@]1([H])N(C([H])([H])[H])[C@@]([H])(C([H])([H])C(=O)C2=C([H])C([H])=C([H])C([H])=C2[H])C([H])([H])C([H])([H])C1([H])[H]

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-/m0/s1

InChI Key

MXYUKLILVYORSK-HBMCJLEFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
ampanula medium	-	KNApSAcK
Campanula medium	KNApSAcK Database	22123792
Hippobroma longiflora	KNApSAcK Database	22123792
Lobelia chinensis	KNApSAcK Database	22123792
Lobelia hassleri	KNApSAcK Database	22123792
Lobelia inflata	KNApSAcK Database	22123792
Lobelia nicotianaefolia	KNApSAcK Database	22123792
Lobelia sessilifolia	KNApSAcK Database	22123792
Lobelia siphilitica	JEOL database	Kesting, J. R., et al, J. Nat. Prod. 72, 312 (2009)
Lobelia urens	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound 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
Organopnictogen compound
Aromatic alcohol
Amine
Organonitrogen compound
Alcohol
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amine (CHEBI:48723 )
aromatic ketone (CHEBI:48723 )
piperidine alkaloid (CHEBI:48723 )
Piperidine alkaloids (C07475 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	130.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	Not Available	Not Available
Water Solubility	48.37 mg/L @ 25 °C (est)	The Good Scents Company Information System
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	39.27 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

DB05137

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002053

Chemspider ID

91814

KEGG Compound ID

C07475

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lobeline

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

48723

Good Scents ID

rw1398201

References

General References

Kulkarni AM, Rampogu S, Lee KW: Computer-Aided Drug Discovery Identifies Alkaloid Inhibitors of Parkinson's Disease Associated Protein, Prolyl Oligopeptidase. Evid Based Complement Alternat Med. 2021 Apr 8;2021:6687572. doi: 10.1155/2021/6687572. eCollection 2021. [PubMed:33897801 ]
Anand A, Sharma R, Srivastava N, Ramakrishnan S: J receptor activity in idiopathic pulmonary hypertension and its expected change in the presence of pulmonary bed vasodilators. Respir Physiol Neurobiol. 2021 Dec;294:103742. doi: 10.1016/j.resp.2021.103742. Epub 2021 Jul 21. [PubMed:34298167 ]
Zheng Q, Wang Y, Zhang S: Beyond Alkaloids: Novel Bioactive Natural Products From Lobelia Species. Front Pharmacol. 2021 Mar 8;12:638210. doi: 10.3389/fphar.2021.638210. eCollection 2021. [PubMed:33762957 ]
Ni C, Li Y, Li Z, Tian L, Fu J, Wu K, Wang Y, Yao M, Ge RS: Cisatracurium stimulates testosterone synthesis in rat and mouse Leydig cells via nicotinic acetylcholine receptor. J Cell Mol Med. 2020 Dec;24(24):14184-14194. doi: 10.1111/jcmm.16029. Epub 2020 Oct 27. [PubMed:33111502 ]
D TK, Jain N, Kumar S U, Jena PP, Ramamoorthy S, Priya Doss C G, Zayed H: Molecular dynamics simulations to decipher the structural and functional consequences of pathogenic missense mutations in the galactosylceramidase (GALC) protein causing Krabbe's disease. J Biomol Struct Dyn. 2021 Mar;39(5):1795-1810. doi: 10.1080/07391102.2020.1742790. Epub 2020 Mar 31. [PubMed:32186243 ]
Kesting, J. R., et al. (2009). Kesting, J. R., et al, J. Nat. Prod. 72, 312 (2009). J. Nat. Prod..

Showing NP-Card for lobeline (NP0034231)

MOL for NP0034231 (lobeline)

3D MOL for NP0034231 (lobeline)

3D SDF for NP0034231 (lobeline)

3D-SDF for NP0034231 (lobeline)

PDB for NP0034231 (lobeline)

3D PDB for NP0034231 (lobeline)

SMILES for NP0034231 (lobeline)

INCHI for NP0034231 (lobeline)

Structure for NP0034231 (lobeline)

3D Structure for NP0034231 (lobeline)