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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:41:47 UTC

Update Date

2022-03-07 03:18:14 UTC

HMDB ID

HMDB0240238

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tolpropamine

Description

Tolpropamine, also known as pragman, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. In humans, tolpropamine is involved in the tolpropamine h1-antihistamine action pathway. Tolpropamine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Tolpropamine.

Structure

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

HMDB0240238
     RDKit          3D
Tolpropamine
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.8345   -2.9985    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949   -2.1756    0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -2.3212   -0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5282   -1.5295   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086   -0.6068    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    0.2162    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208   -0.6245    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    0.2897    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464   -0.4362   -0.1162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6407    0.5202   -0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8354   -1.4635    0.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2186    1.4253   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    1.4546   -1.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078    2.6254   -2.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009    3.8022   -1.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566    3.7968   -0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143    2.6277    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2342   -0.4546    1.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -1.2408    1.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864   -3.9668    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0684   -3.1462    1.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6280   -2.4388    0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8325   -3.0514   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244   -1.6917   -1.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765    0.5672    1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -1.0761   -0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2343   -1.4604    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3904    0.7342    1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    1.0623   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6333    0.0093   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5718    1.1626    0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5559    1.1419   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5145   -1.0990    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -2.4284    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9471   -1.6495    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    0.5235   -2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    2.6065   -3.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6159    4.7326   -2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    4.7106    0.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    2.6747    1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843    0.2823    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907   -1.1063    2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 17 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END

      
  Mrv1652301021820212D          

 19 20  0  0  0  0            999 V2000
   -0.4908    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2053    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4908    2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9197    1.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343    0.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6344    0.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9199   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2053    0.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6525    0.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6526    0.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9380    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    3.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4908    3.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9380    3.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3670   -0.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  5  2  0  0  0  0
  9  2  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  4 10  2  0  0  0  0
 14  4  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240238

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC(C1=CC=CC=C1)C1=CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H23N/c1-15-9-11-17(12-10-15)18(13-14-19(2)3)16-7-5-4-6-8-16/h4-12,18H,13-14H2,1-3H3

> <INCHI_KEY>
CINROOONPHQHPO-UHFFFAOYSA-N

> <FORMULA>
C18H23N

> <MOLECULAR_WEIGHT>
253.389

> <EXACT_MASS>
253.183049745

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.244185347825358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl[3-(4-methylphenyl)-3-phenylpropyl]amine

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
4.582116911333333

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.646124322851849

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
83.64150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pragman

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240238
     RDKit          3D
Tolpropamine
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.8345   -2.9985    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949   -2.1756    0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -2.3212   -0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5282   -1.5295   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086   -0.6068    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    0.2162    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208   -0.6245    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    0.2897    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464   -0.4362   -0.1162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6407    0.5202   -0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8354   -1.4635    0.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2186    1.4253   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    1.4546   -1.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078    2.6254   -2.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009    3.8022   -1.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566    3.7968   -0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143    2.6277    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2342   -0.4546    1.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -1.2408    1.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864   -3.9668    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0684   -3.1462    1.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6280   -2.4388    0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8325   -3.0514   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244   -1.6917   -1.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765    0.5672    1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -1.0761   -0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2343   -1.4604    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3904    0.7342    1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    1.0623   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6333    0.0093   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5718    1.1626    0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5559    1.1419   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5145   -1.0990    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -2.4284    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9471   -1.6495    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    0.5235   -2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    2.6065   -3.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6159    4.7326   -2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    4.7106    0.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    2.6747    1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843    0.2823    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907   -1.1063    2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 17 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END

HEADER    PROTEIN                                 02-JAN-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-JAN-18         0                                  
HETATM    1  C   UNK     0      -0.916   2.520   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.250   1.750   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.916   4.060   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.417   1.750   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.583   2.520   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.917   1.750   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.918   0.210   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.584  -0.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.250   0.210   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.417   0.210   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.751  -0.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.085   0.210   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.085   1.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.751   2.520   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.417   4.830   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.417   6.370   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.916   7.140   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.751   7.140   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.418  -0.560   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    9                                                  
CONECT    3    1   15                                                       
CONECT    4    1   10   14                                                  
CONECT    5    6    2                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    2                                                       
CONECT   10   11    4                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13    4                                                       
CONECT   15    3   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   12                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0240238
HETATM    1  C1  UNL     1       4.834  -2.998   0.581  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.595  -2.176   0.542  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.663  -2.321  -0.462  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.528  -1.529  -0.448  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.309  -0.607   0.536  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.089   0.216   0.518  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.121  -0.624   0.184  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.330   0.290   0.195  1.00  0.00           C  
HETATM    9  N1  UNL     1      -3.546  -0.436  -0.116  1.00  0.00           N  
HETATM   10  C9  UNL     1      -4.641   0.520  -0.082  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.835  -1.463   0.851  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.219   1.425  -0.312  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.035   1.455  -1.674  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.108   2.625  -2.389  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.501   3.802  -1.799  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.757   3.797  -0.454  1.00  0.00           C  
HETATM   17  C16 UNL     1       0.614   2.628   0.259  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.234  -0.455   1.542  1.00  0.00           C  
HETATM   19  C18 UNL     1       3.366  -1.241   1.533  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.586  -3.967   0.109  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.068  -3.146   1.668  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.628  -2.439   0.073  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.833  -3.051  -1.243  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.824  -1.692  -1.277  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.077   0.567   1.581  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.035  -1.076  -0.832  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.234  -1.460   0.897  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.390   0.734   1.199  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.183   1.062  -0.562  1.00  0.00           H  
HETATM   30  H11 UNL     1      -5.633   0.009  -0.035  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.572   1.163   0.844  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.556   1.142  -0.996  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.514  -1.099   1.845  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.347  -2.428   0.570  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.947  -1.649   0.818  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.347   0.523  -2.147  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.099   2.606  -3.450  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.616   4.733  -2.358  1.00  0.00           H  
HETATM   39  H20 UNL     1       1.068   4.711   0.038  1.00  0.00           H  
HETATM   40  H21 UNL     1       0.828   2.675   1.318  1.00  0.00           H  
HETATM   41  H22 UNL     1       2.084   0.282   2.350  1.00  0.00           H  
HETATM   42  H23 UNL     1       4.091  -1.106   2.340  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   19
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6   18
CONECT    6    7   12   25
CONECT    7    8   26   27
CONECT    8    9   28   29
CONECT    9   10   11
CONECT   10   30   31   32
CONECT   11   33   34   35
CONECT   12   13   13   17
CONECT   13   14   36
CONECT   14   15   15   37
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   40
CONECT   18   19   19   41
CONECT   19   42
END

HMDB0240238
     RDKit          3D
Tolpropamine
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.8345   -2.9985    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949   -2.1756    0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -2.3212   -0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5282   -1.5295   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086   -0.6068    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    0.2162    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208   -0.6245    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    0.2897    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464   -0.4362   -0.1162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6407    0.5202   -0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8354   -1.4635    0.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2186    1.4253   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347    1.4546   -1.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078    2.6254   -2.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009    3.8022   -1.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566    3.7968   -0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143    2.6277    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2342   -0.4546    1.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -1.2408    1.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864   -3.9668    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0684   -3.1462    1.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6280   -2.4388    0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8325   -3.0514   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244   -1.6917   -1.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765    0.5672    1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -1.0761   -0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2343   -1.4604    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3904    0.7342    1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828    1.0623   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6333    0.0093   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5718    1.1626    0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5559    1.1419   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5145   -1.0990    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -2.4284    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9471   -1.6495    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    0.5235   -2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    2.6065   -3.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6159    4.7326   -2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    4.7106    0.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    2.6747    1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843    0.2823    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907   -1.1063    2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 17 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N,N-4-Trimethyl-gamma-phenylbenzenepropan	MeSH
N,N-Dimethyl-3-phenyl-3-(p-tolyl)propylamine	MeSH
Pragman	MeSH
Tolpropamine hydrochloride	MeSH
Tolpropamine	HMDB

Chemical Formula

C₁₈H₂₃N

Average Molecular Weight

253.389

Monoisotopic Molecular Weight

253.183049745

IUPAC Name

dimethyl[3-(4-methylphenyl)-3-phenylpropyl]amine

Traditional Name

pragman

CAS Registry Number

5632-44-0

SMILES

CN(C)CCC(C1=CC=CC=C1)C1=CC=C(C)C=C1

InChI Identifier

InChI=1S/C18H23N/c1-15-9-11-17(12-10-15)18(13-14-19(2)3)16-7-5-4-6-8-16/h4-12,18H,13-14H2,1-3H3

InChI Key

CINROOONPHQHPO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Monoterpenoid
Monocyclic monoterpenoid
Aromatic monoterpenoid
P-cymene
Aralkylamine
Toluene
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

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	4.09	ALOGPS
logP	4.58	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	9.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.64 m³·mol⁻¹	ChemAxon
Polarizability	31.24 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M-H]-	169.326	31661259
AllCCS	[M+H]+	158.741	31661259
DeepCCS	[M+H]+	165.965	30932474
DeepCCS	[M-H]-	163.607	30932474
DeepCCS	[M-2H]-	196.493	30932474
DeepCCS	[M+Na]+	172.058	30932474
AllCCS	[M+H]+	158.7	32859911
AllCCS	[M+H-H2O]+	154.8	32859911
AllCCS	[M+NH4]+	162.4	32859911
AllCCS	[M+Na]+	163.4	32859911
AllCCS	[M-H]-	169.3	32859911
AllCCS	[M+Na-2H]-	169.3	32859911
AllCCS	[M+HCOO]-	169.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.31 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8454 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.96 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1221.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	283.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	117.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	435.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	478.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	477.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1171.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	367.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1293.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	252.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	350.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	315.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	259.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tolpropamine	CN(C)CCC(C1=CC=CC=C1)C1=CC=C(C)C=C1	2459.8	Standard polar	33892256
Tolpropamine	CN(C)CCC(C1=CC=CC=C1)C1=CC=C(C)C=C1	1927.2	Standard non polar	33892256
Tolpropamine	CN(C)CCC(C1=CC=CC=C1)C1=CC=C(C)C=C1	1877.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tolpropamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-7920000000-074dc79b1052dd0931e7	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolpropamine 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 - Tolpropamine 10V, Positive-QTOF	splash10-0udi-0090000000-20595ab35a506ecfe090	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 20V, Positive-QTOF	splash10-0zfr-0390000000-9599381daf54c96d5a9d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 40V, Positive-QTOF	splash10-0as0-2940000000-dfe2f5f1a9e8d0ba09de	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 10V, Negative-QTOF	splash10-0udi-0090000000-79b01f2515ae8fd30269	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 20V, Negative-QTOF	splash10-0udi-1090000000-f4ae73472da1c75ed569	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 40V, Negative-QTOF	splash10-054o-9650000000-2f9f305607425f11d0fa	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 10V, Positive-QTOF	splash10-0zfr-0090000000-801df037a10f4e3a6c49	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 20V, Positive-QTOF	splash10-0a4i-1590000000-fc42a496cced028107b6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 40V, Positive-QTOF	splash10-069u-3900000000-47e33e53c43a75628e31	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 10V, Negative-QTOF	splash10-0udi-0090000000-29f321564479847420fe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 20V, Negative-QTOF	splash10-0udl-8590000000-6abeda0a0ffd17982940	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolpropamine 40V, Negative-QTOF	splash10-0fc3-5910000000-b4ffcf73120a5957f2c7	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tolpropamine H1-Antihistamine Action		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13305

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

65115

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tolpropamine

METLIN ID

Not Available

PubChem Compound

72141

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

Montgomery LC, Deuster PA: Effects of antihistamine medications on exercise performance. Implications for sportspeople. Sports Med. 1993 Mar;15(3):179-95. [PubMed:7680815 ]

Showing metabocard for Tolpropamine (HMDB0240238)

MOL for HMDB0240238 (Tolpropamine)

3D MOL for HMDB0240238 (Tolpropamine)

3D SDF for HMDB0240238 (Tolpropamine)

3D-SDF for HMDB0240238 (Tolpropamine)

PDB for HMDB0240238 (Tolpropamine)

3D PDB for HMDB0240238 (Tolpropamine)

SMILES for HMDB0240238 (Tolpropamine)

INCHI for HMDB0240238 (Tolpropamine)

Structure for HMDB0240238 (Tolpropamine)

3D Structure for HMDB0240238 (Tolpropamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra