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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:19:20 UTC

Update Date

2021-09-26 23:07:56 UTC

HMDB ID

HMDB0254137

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Inflatine

Description

lobeline, also known as smokeless or lobeline sulfate, 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. 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. 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. 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. It has been hypothesized that P-glycoprotein inhibition reduces chemotherapeutic resistance in cancer, presumably affecting any substrates of P-gp. 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. This compound has been identified in human blood as reported by (PMID: 31557052 ). Inflatine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Inflatine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0254139
     RDKit          3D
Lobeline
 52 54  0  0  0  0  0  0  0  0999 V2000
    0.6224   -0.3137   -1.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3642   -1.0821   -0.5242 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -0.8018    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0744    0.1832    0.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.1800   -0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268   -1.2548   -0.6777 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3927    0.7789   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5182    0.5071   -0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5445    1.4107   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915    2.6263   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3506    2.8920    0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097    1.9948    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -2.1325    1.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020   -3.0525    1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0925   -2.4553    0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9519   -1.6475   -0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9494   -0.5166   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3680   -0.9603   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -1.6847    0.8859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417    0.2368   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5840    0.0761    0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4625    1.1297    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0273    2.4111    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7128    2.6028   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8288    1.5192   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793   -0.3947   -2.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4343   -0.6837   -2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    0.7847   -1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -0.4052    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389    0.2981    1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7671    1.2068    0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019   -0.4479   -1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4256    1.1800   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3013    3.3490   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2865    3.8515    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4203    2.1969    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -2.6178    0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -1.9860    2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4155   -4.0056    0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0625   -3.4316    2.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388   -1.7968    1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268   -3.2659    0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1467   -2.2829   -1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8946    0.0772   -1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7081    0.1886    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681   -1.5798   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7908   -1.0734    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9180   -0.9298    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5098    0.9591    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7461    3.2258    0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708    3.6008   -0.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7897    1.6955   -0.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  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 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  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
 16  2  1  0
 25 20  1  0
 12  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  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
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
M  END

  Mrv1533004171505122D          

 25 27  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    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
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254137

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(CC(O)C2=CC=CC=C2)CCCC1CC(=O)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

> <INCHI_KEY>
MXYUKLILVYORSK-UHFFFAOYSA-N

> <FORMULA>
C22H27NO2

> <MOLECULAR_WEIGHT>
337.463

> <EXACT_MASS>
337.204179113

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.905896106526384

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[6-(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>
101.5121

> <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

$$$$

HMDB0254139
     RDKit          3D
Lobeline
 52 54  0  0  0  0  0  0  0  0999 V2000
    0.6224   -0.3137   -1.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3642   -1.0821   -0.5242 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -0.8018    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0744    0.1832    0.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.1800   -0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268   -1.2548   -0.6777 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3927    0.7789   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5182    0.5071   -0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5445    1.4107   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915    2.6263   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3506    2.8920    0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097    1.9948    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -2.1325    1.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020   -3.0525    1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0925   -2.4553    0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9519   -1.6475   -0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9494   -0.5166   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3680   -0.9603   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -1.6847    0.8859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417    0.2368   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5840    0.0761    0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4625    1.1297    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0273    2.4111    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7128    2.6028   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8288    1.5192   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793   -0.3947   -2.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4343   -0.6837   -2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    0.7847   -1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -0.4052    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389    0.2981    1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7671    1.2068    0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019   -0.4479   -1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4256    1.1800   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3013    3.3490   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2865    3.8515    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4203    2.1969    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -2.6178    0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -1.9860    2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4155   -4.0056    0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0625   -3.4316    2.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388   -1.7968    1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268   -3.2659    0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1467   -2.2829   -1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8946    0.0772   -1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7081    0.1886    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681   -1.5798   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7908   -1.0734    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9180   -0.9298    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5098    0.9591    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7461    3.2258    0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708    3.6008   -0.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7897    1.6955   -0.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  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 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  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
 16  2  1  0
 25 20  1  0
 12  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  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
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    3   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0254139
HETATM    1  C1  UNL     1       0.622  -0.314  -1.656  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.364  -1.082  -0.524  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.967  -0.802   0.725  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.074   0.183   0.746  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.267  -0.180  -0.052  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.427  -1.255  -0.678  1.00  0.00           O  
HETATM    7  C5  UNL     1       4.393   0.779  -0.149  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.518   0.507  -0.868  1.00  0.00           C  
HETATM    9  C7  UNL     1       6.544   1.411  -0.938  1.00  0.00           C  
HETATM   10  C8  UNL     1       6.492   2.626  -0.293  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.351   2.892   0.431  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.310   1.995   0.513  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.379  -2.133   1.345  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.202  -3.052   1.332  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.092  -2.455   0.862  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.952  -1.648  -0.397  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.949  -0.517  -0.387  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.368  -0.960  -0.279  1.00  0.00           C  
HETATM   19  O2  UNL     1      -3.560  -1.685   0.886  1.00  0.00           O  
HETATM   20  C17 UNL     1      -4.242   0.237  -0.197  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.584   0.076   0.150  1.00  0.00           C  
HETATM   22  C19 UNL     1      -6.462   1.130   0.255  1.00  0.00           C  
HETATM   23  C20 UNL     1      -6.027   2.411   0.014  1.00  0.00           C  
HETATM   24  C21 UNL     1      -4.713   2.603  -0.329  1.00  0.00           C  
HETATM   25  C22 UNL     1      -3.829   1.519  -0.433  1.00  0.00           C  
HETATM   26  H1  UNL     1      -0.279  -0.395  -2.344  1.00  0.00           H  
HETATM   27  H2  UNL     1       1.434  -0.684  -2.349  1.00  0.00           H  
HETATM   28  H3  UNL     1       0.727   0.785  -1.492  1.00  0.00           H  
HETATM   29  H4  UNL     1       0.164  -0.405   1.394  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.439   0.298   1.805  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.767   1.207   0.446  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.602  -0.448  -1.397  1.00  0.00           H  
HETATM   33  H8  UNL     1       7.426   1.180  -1.511  1.00  0.00           H  
HETATM   34  H9  UNL     1       7.301   3.349  -0.343  1.00  0.00           H  
HETATM   35  H10 UNL     1       5.286   3.851   0.952  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.420   2.197   1.077  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.170  -2.618   0.718  1.00  0.00           H  
HETATM   38  H13 UNL     1       1.742  -1.986   2.388  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.416  -4.006   0.757  1.00  0.00           H  
HETATM   40  H15 UNL     1       0.062  -3.432   2.381  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.439  -1.797   1.685  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.827  -3.266   0.761  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.147  -2.283  -1.262  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.895   0.077  -1.344  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.708   0.189   0.423  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.668  -1.580  -1.159  1.00  0.00           H  
HETATM   47  H22 UNL     1      -3.791  -1.073   1.609  1.00  0.00           H  
HETATM   48  H23 UNL     1      -5.918  -0.930   0.338  1.00  0.00           H  
HETATM   49  H24 UNL     1      -7.510   0.959   0.531  1.00  0.00           H  
HETATM   50  H25 UNL     1      -6.746   3.226   0.105  1.00  0.00           H  
HETATM   51  H26 UNL     1      -4.371   3.601  -0.518  1.00  0.00           H  
HETATM   52  H27 UNL     1      -2.790   1.696  -0.701  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   16
CONECT    3    4   13   29
CONECT    4    5   30   31
CONECT    5    6    6    7
CONECT    7    8    8   12
CONECT    8    9   32
CONECT    9   10   10   33
CONECT   10   11   34
CONECT   11   12   12   35
CONECT   12   36
CONECT   13   14   37   38
CONECT   14   15   39   40
CONECT   15   16   41   42
CONECT   16   17   43
CONECT   17   18   44   45
CONECT   18   19   20   46
CONECT   19   47
CONECT   20   21   21   25
CONECT   21   22   48
CONECT   22   23   23   49
CONECT   23   24   50
CONECT   24   25   25   51
CONECT   25   52
END

HMDB0254139
     RDKit          3D
Lobeline
 52 54  0  0  0  0  0  0  0  0999 V2000
    0.6224   -0.3137   -1.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3642   -1.0821   -0.5242 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -0.8018    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0744    0.1832    0.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -0.1800   -0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268   -1.2548   -0.6777 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3927    0.7789   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5182    0.5071   -0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5445    1.4107   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915    2.6263   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3506    2.8920    0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097    1.9948    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -2.1325    1.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020   -3.0525    1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0925   -2.4553    0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9519   -1.6475   -0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9494   -0.5166   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3680   -0.9603   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -1.6847    0.8859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417    0.2368   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5840    0.0761    0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4625    1.1297    0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0273    2.4111    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7128    2.6028   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8288    1.5192   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793   -0.3947   -2.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4343   -0.6837   -2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    0.7847   -1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -0.4052    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389    0.2981    1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7671    1.2068    0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019   -0.4479   -1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4256    1.1800   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3013    3.3490   -0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2865    3.8515    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4203    2.1969    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -2.6178    0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -1.9860    2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4155   -4.0056    0.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0625   -3.4316    2.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388   -1.7968    1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268   -3.2659    0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1467   -2.2829   -1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8946    0.0772   -1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7081    0.1886    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6681   -1.5798   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7908   -1.0734    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9180   -0.9298    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5098    0.9591    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7461    3.2258    0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708    3.6008   -0.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7897    1.6955   -0.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  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 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  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
 16  2  1  0
 25 20  1  0
 12  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  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
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₂₂H₂₇NO₂

Average Molecular Weight

337.463

Monoisotopic Molecular Weight

337.204179113

IUPAC Name

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

Traditional Name

lobeline

CAS Registry Number

Not Available

SMILES

CN1C(CC(O)C2=CC=CC=C2)CCCC1CC(=O)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

InChI Key

MXYUKLILVYORSK-UHFFFAOYSA-N

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
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	38.91 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	180.343	30932474
DeepCCS	[M-H]-	177.985	30932474
DeepCCS	[M-2H]-	211.602	30932474
DeepCCS	[M+Na]+	186.953	30932474
AllCCS	[M+H]+	187.6	32859911
AllCCS	[M+H-H2O]+	184.6	32859911
AllCCS	[M+NH4]+	190.4	32859911
AllCCS	[M+Na]+	191.2	32859911
AllCCS	[M-H]-	186.3	32859911
AllCCS	[M+Na-2H]-	186.6	32859911
AllCCS	[M+HCOO]-	187.1	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Inflatine,1TMS,isomer #1	CN1C(CC(=O)C2=CC=CC=C2)CCCC1CC(O[Si](C)(C)C)C1=CC=CC=C1	2684.3	Semi standard non polar	33892256
Inflatine,1TMS,isomer #1	CN1C(CC(=O)C2=CC=CC=C2)CCCC1CC(O[Si](C)(C)C)C1=CC=CC=C1	2666.5	Standard non polar	33892256
Inflatine,1TMS,isomer #1	CN1C(CC(=O)C2=CC=CC=C2)CCCC1CC(O[Si](C)(C)C)C1=CC=CC=C1	3453.5	Standard polar	33892256
Inflatine,1TBDMS,isomer #1	CN1C(CC(=O)C2=CC=CC=C2)CCCC1CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2891.6	Semi standard non polar	33892256
Inflatine,1TBDMS,isomer #1	CN1C(CC(=O)C2=CC=CC=C2)CCCC1CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2942.3	Standard non polar	33892256
Inflatine,1TBDMS,isomer #1	CN1C(CC(=O)C2=CC=CC=C2)CCCC1CC(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3542.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Inflatine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4940000000-148c0748633d7ad64c21	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inflatine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inflatine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Inflatine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Inflatine 10V, Positive-QTOF	splash10-000i-0009000000-236260bc12143449d69e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Inflatine 20V, Positive-QTOF	splash10-00ri-2269000000-f7b9c996cc9906806990	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Inflatine 40V, Positive-QTOF	splash10-01ot-8931000000-58733f4314e3ffdaf198	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Inflatine 10V, Negative-QTOF	splash10-000i-0009000000-531288296b3f3048e10e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Inflatine 20V, Negative-QTOF	splash10-014i-2639000000-ba9701c97d2311c70d26	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Inflatine 40V, Negative-QTOF	splash10-00b9-6940000000-49e69a6a2a2d1716c3ff	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

3945

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Inflatine (HMDB0254137)

MOL for HMDB0254137 (Inflatine)

3D MOL for HMDB0254137 (Inflatine)

3D SDF for HMDB0254137 (Inflatine)

3D-SDF for HMDB0254137 (Inflatine)

PDB for HMDB0254137 (Inflatine)

3D PDB for HMDB0254137 (Inflatine)

SMILES for HMDB0254137 (Inflatine)

INCHI for HMDB0254137 (Inflatine)

Structure for HMDB0254137 (Inflatine)

3D Structure for HMDB0254137 (Inflatine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra