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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (1) Show 2 proteins XML

enzymes (1)transporters (1) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:23 UTC

HMDB ID

HMDB0015072

Secondary Accession Numbers

HMDB15072

Metabolite Identification

Common Name

Diethylpropion

Description

Diethylpropion is only found in individuals that have used or taken this drug. It is a appetite depressant considered to produce less central nervous system disturbance than most drugs in this therapeutic category. It is also considered to be among the safest for patients with hypertension. (From AMA Drug Evaluations Annual, 1994, p2290)Diethylpropion is an amphetamine that stimulates neurons to release or maintain high levels of a particular group of neurotransmitters known as catecholamines; these include dopamine and norepinephrine. High levels of these catecholamines tend to suppress hunger signals and appetite. Diethylpropion (through catecholamine elevation) may also indirectly affect leptin levels in the brain. It is theorized that diethylpropion can raise levels of leptin which signal satiety. It is also theorized that increased levels of the catecholamines are partially responsible for halting another chemical messenger known as neuropeptide Y. This peptide initiates eating, decreases energy expenditure, and increases fat storage.

Structure

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

HMDB0015072
     RDKit          3D
Diethylpropion
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.0367   -0.1327   -0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684   -0.7802   -0.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449    0.1515   -0.1034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    0.0893    1.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339    1.2889    2.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -0.3811   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1389   -1.7059    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5956    0.6555   -0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883    1.8466   -0.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.5041   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736    1.6099   -0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2440    1.5503   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8087    0.3488   -0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310   -0.7408   -0.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6303   -0.6822   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9082    0.9687   -0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5938   -0.4102   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414   -0.4853    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6746   -1.7630   -0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246   -0.7584   -1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690   -0.8000    1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -0.1662    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820    1.3725    3.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    1.2170    2.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479    2.2536    1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4917   -0.6177   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1315   -2.5091   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607   -2.1871    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -1.7422    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    2.5624    0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8686    2.4330    0.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8933    0.2900   -0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4523   -1.6974   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -1.5824   -0.8868 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
  3  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
M  END

937
  Mrv0541 02231215072D          

 15 15  0  0  1  0            999 V2000
    1.6500    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015072

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)C(C)C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3

> <INCHI_KEY>
XXEPPPIWZFICOJ-UHFFFAOYSA-N

> <FORMULA>
C13H19NO

> <MOLECULAR_WEIGHT>
205.2961

> <EXACT_MASS>
205.146664235

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.124410458659263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(diethylamino)-1-phenylpropan-1-one

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
2.7047719746666665

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.427207749681955

> <JCHEM_PKA_STRONGEST_BASIC>
7.441676162944761

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
63.880900000000025

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diethylpropion

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015072
     RDKit          3D
Diethylpropion
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.0367   -0.1327   -0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684   -0.7802   -0.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449    0.1515   -0.1034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    0.0893    1.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339    1.2889    2.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -0.3811   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1389   -1.7059    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5956    0.6555   -0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883    1.8466   -0.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.5041   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736    1.6099   -0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2440    1.5503   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8087    0.3488   -0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310   -0.7408   -0.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6303   -0.6822   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9082    0.9687   -0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5938   -0.4102   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414   -0.4853    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6746   -1.7630   -0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246   -0.7584   -1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690   -0.8000    1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -0.1662    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820    1.3725    3.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    1.2170    2.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479    2.2536    1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4917   -0.6177   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1315   -2.5091   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607   -2.1871    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -1.7422    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    2.5624    0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8686    2.4330    0.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8933    0.2900   -0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4523   -1.6974   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -1.5824   -0.8868 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
  3  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 937                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   0.770   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.747   2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.747   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.081   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -4.620   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    3    4    5                                                  
CONECT    3    2    6    7                                                  
CONECT    4    2    8                                                       
CONECT    5    2    9                                                       
CONECT    6    1    3   10                                                  
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    6   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   15                                                       
CONECT   15   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0015072
HETATM    1  C1  UNL     1      -4.037  -0.133  -0.764  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.668  -0.780  -0.837  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.745   0.151  -0.103  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.115   0.089   1.292  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.634   1.289   2.060  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.392  -0.381  -0.377  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.139  -1.706   0.223  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.596   0.655  -0.226  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.188   1.847  -0.003  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.054   0.504  -0.303  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.874   1.610  -0.044  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.244   1.550  -0.129  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.809   0.349  -0.485  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.031  -0.741  -0.742  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.630  -0.682  -0.655  1.00  0.00           C  
HETATM   16  H1  UNL     1      -3.908   0.969  -0.775  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.594  -0.410  -1.677  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.641  -0.485   0.094  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.675  -1.763  -0.422  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.325  -0.758  -1.873  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.569  -0.800   1.744  1.00  0.00           H  
HETATM   22  H7  UNL     1      -3.183  -0.166   1.469  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.282   1.373   3.004  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.590   1.217   2.405  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.848   2.254   1.558  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.492  -0.618  -1.520  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.132  -2.509  -0.551  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.061  -2.187   0.665  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.651  -1.742   0.987  1.00  0.00           H  
HETATM   30  H15 UNL     1       2.402   2.562   0.237  1.00  0.00           H  
HETATM   31  H16 UNL     1       4.869   2.433   0.086  1.00  0.00           H  
HETATM   32  H17 UNL     1       5.893   0.290  -0.553  1.00  0.00           H  
HETATM   33  H18 UNL     1       4.452  -1.697  -1.020  1.00  0.00           H  
HETATM   34  H19 UNL     1       2.073  -1.582  -0.887  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4    6
CONECT    4    5   21   22
CONECT    5   23   24   25
CONECT    6    7    8   26
CONECT    7   27   28   29
CONECT    8    9    9   10
CONECT   10   11   11   15
CONECT   11   12   30
CONECT   12   13   13   31
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   34
END

HMDB0015072
     RDKit          3D
Diethylpropion
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.0367   -0.1327   -0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684   -0.7802   -0.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449    0.1515   -0.1034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    0.0893    1.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339    1.2889    2.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -0.3811   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1389   -1.7059    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5956    0.6555   -0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883    1.8466   -0.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.5041   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736    1.6099   -0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2440    1.5503   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8087    0.3488   -0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310   -0.7408   -0.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6303   -0.6822   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9082    0.9687   -0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5938   -0.4102   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414   -0.4853    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6746   -1.7630   -0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246   -0.7584   -1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690   -0.8000    1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -0.1662    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820    1.3725    3.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    1.2170    2.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479    2.2536    1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4917   -0.6177   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1315   -2.5091   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607   -2.1871    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -1.7422    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    2.5624    0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8686    2.4330    0.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8933    0.2900   -0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4523   -1.6974   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -1.5824   -0.8868 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
  3  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Diethylpropion	ChEBI
1-Phenyl-2-diethylamino-1-propanone	ChEBI
2-(Diethylamino)-1-phenyl-1-propanone	ChEBI
2-(Diethylamino)propiophenone	ChEBI
alpha-Benzoyltriethylamine	ChEBI
alpha-Diethylaminopropiophenone	ChEBI
Amfepramone	ChEBI
Amfepramonum	ChEBI
Anfepramona	ChEBI
a-Benzoyltriethylamine	Generator
Α-benzoyltriethylamine	Generator
a-Diethylaminopropiophenone	Generator
Α-diethylaminopropiophenone	Generator
DEA no. 1610	HMDB
Diethylcathinone	HMDB
Diethylpropione	HMDB
3m Brand OF amfepramone hydrochloride	HMDB
Anorex	HMDB
Crinex brand OF amfepramone hydrochloride	HMDB
Delgamer	HMDB
Lipomin	HMDB
Marion merrell dow brand OF amfepramone hydrochloride	HMDB
Nobesine	HMDB
Préfamone	HMDB
Théranol brand OF amfepramone hydrochloride	HMDB
Uriach brand OF amfepramone hydrochloride	HMDB
2-Diethylaminopropiophenone	HMDB
Dexo brand OF amfepramone hydrochloride	HMDB
Ifa norex	HMDB
Medic brand OF amfepramone hydrochloride	HMDB
Neobes	HMDB
Regibon	HMDB
Dietil retard	HMDB
Dietilretard	HMDB
Hydrochloride, diethylpropion	HMDB
Maruate	HMDB
Medix brand OF amfepramone hydrochloride	HMDB
Norex, ifa	HMDB
Propion	HMDB
Vortech brand OF amfepramone hydrochloride	HMDB
Amfepramon	HMDB
Artegodan brand OF amfepramone hydrochloride	HMDB
Diethylpropion hydrochloride	HMDB
Dietil-retard	HMDB
Hoechst brand OF amfepramone hydrochloride	HMDB
Investigacion farmaceutica brand OF amfepramone hydrochloride	HMDB
Marion merrell brand OF amfepramone hydrochloride	HMDB
Modératan	HMDB
Nadeau brand OF amfepramone hydrochloride	HMDB
Phepranon	HMDB
Pro DOC brand OF amfepramone hydrochloride	HMDB
Regenon	HMDB
Temmler brand OF amfepramone hydrochloride	HMDB
Tenuate	HMDB
Tepanil	HMDB

Chemical Formula

C₁₃H₁₉NO

Average Molecular Weight

205.2961

Monoisotopic Molecular Weight

205.146664235

IUPAC Name

2-(diethylamino)-1-phenylpropan-1-one

Traditional Name

diethylpropion

CAS Registry Number

134-80-5

SMILES

CCN(CC)C(C)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3

InChI Key

XXEPPPIWZFICOJ-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
Phenylpropane
Benzoyl
Aryl alkyl ketone
Benzenoid
Monocyclic benzene moiety
Alpha-aminoketone
Tertiary aliphatic amine
Tertiary amine
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amine (CHEBI:4530 )
aromatic ketone (CHEBI:4530 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015072)

Source

Exogenous

Exogenous (HMDB: HMDB0015072)

Process

Not Available

Role

Industrial application

Appetite depressant (HMDB: HMDB0015072)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.22 g/L	Not Available
LogP	2.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	148.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.22 g/L	ALOGPS
logP	2.8	ALOGPS
logP	2.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	17.43	ChemAxon
pKa (Strongest Basic)	7.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	63.88 m³·mol⁻¹	ChemAxon
Polarizability	24.12 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	148.209	31661259
DarkChem	[M-H]-	145.781	31661259
DeepCCS	[M+H]+	148.701	30932474
DeepCCS	[M-H]-	146.343	30932474
DeepCCS	[M-2H]-	180.82	30932474
DeepCCS	[M+Na]+	156.051	30932474
AllCCS	[M+H]+	147.2	32859911
AllCCS	[M+H-H2O]+	143.1	32859911
AllCCS	[M+NH4]+	150.9	32859911
AllCCS	[M+Na]+	152.0	32859911
AllCCS	[M-H]-	152.3	32859911
AllCCS	[M+Na-2H]-	153.0	32859911
AllCCS	[M+HCOO]-	153.9	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.	4.92 minutes	32390414
Predicted by Siyang on May 30, 2022	10.084 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.81 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	45.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1307.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	253.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	309.9 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	344.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	800.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	319.7 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	970.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	284.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	269.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	297.3 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	29.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diethylpropion	CCN(CC)C(C)C(=O)C1=CC=CC=C1	1960.5	Standard polar	33892256
Diethylpropion	CCN(CC)C(C)C(=O)C1=CC=CC=C1	1542.2	Standard non polar	33892256
Diethylpropion	CCN(CC)C(C)C(=O)C1=CC=CC=C1	1507.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Diethylpropion EI-B (Non-derivatized)	splash10-0udi-9600000000-6ee5a640521355e9e385	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethylpropion EI-B (Non-derivatized)	splash10-0udi-9600000000-6ee5a640521355e9e385	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethylpropion GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pb9-4900000000-dfe406cfb26414d42c91	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethylpropion GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-2900000000-43214c102b76f59ba4d1	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 10V, Positive-QTOF	splash10-0a4i-0390000000-ce898493104c3b4c2c47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 20V, Positive-QTOF	splash10-0pb9-1920000000-96569e0397bae3f7dad7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 40V, Positive-QTOF	splash10-0kor-9400000000-099deea1407beaa58a50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 10V, Negative-QTOF	splash10-0udi-0190000000-95dcba361e53234bdef9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 20V, Negative-QTOF	splash10-0udi-5590000000-1b565cac019e1aaf4095	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 40V, Negative-QTOF	splash10-0kl0-8900000000-7a17ddfd7a2fe78351c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 10V, Positive-QTOF	splash10-0a4i-0290000000-e6b4a514d0501abfde52	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 20V, Positive-QTOF	splash10-0zfr-1920000000-454738ae8af99f176428	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 40V, Positive-QTOF	splash10-0fb9-9500000000-1d8dda4d3070e4f07ca5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 10V, Negative-QTOF	splash10-0udi-0090000000-cd886772587c719fa7c6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 20V, Negative-QTOF	splash10-0ufr-6690000000-31723177ed3fe7247254	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylpropion 40V, Negative-QTOF	splash10-004i-9100000000-96fa4edb3fe7918f8909	2021-10-11	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00937	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00937	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00937

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6762

KEGG Compound ID

C06954

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diethylpropion

METLIN ID

Not Available

PubChem Compound

7029

PDB ID

Not Available

ChEBI ID

4530

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

Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. doi: 10.1016/S0074-7742(09)88009-4. [PubMed:19897080 ]
Adan RA, Vanderschuren LJ, la Fleur SE: Anti-obesity drugs and neural circuits of feeding. Trends Pharmacol Sci. 2008 Apr;29(4):208-17. doi: 10.1016/j.tips.2008.01.008. Epub 2008 Mar 18. [PubMed:18353447 ]

Enzymes

Enzyme Details

1. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Yu H, Rothman RB, Dersch CM, Partilla JS, Rice KC: Uptake and release effects of diethylpropion and its metabolites with biogenic amine transporters. Bioorg Med Chem. 2000 Dec;8(12):2689-92. [PubMed:11131159 ]
Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. doi: 10.1016/S0074-7742(09)88009-4. [PubMed:19897080 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. doi: 10.1016/S0074-7742(09)88009-4. [PubMed:19897080 ]

Showing metabocard for Diethylpropion (HMDB0015072)

MOL for HMDB0015072 (Diethylpropion)

3D MOL for HMDB0015072 (Diethylpropion)

3D SDF for HMDB0015072 (Diethylpropion)

3D-SDF for HMDB0015072 (Diethylpropion)

PDB for HMDB0015072 (Diethylpropion)

3D PDB for HMDB0015072 (Diethylpropion)

SMILES for HMDB0015072 (Diethylpropion)

INCHI for HMDB0015072 (Diethylpropion)

Structure for HMDB0015072 (Diethylpropion)

3D Structure for HMDB0015072 (Diethylpropion)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

References

Transporters

References