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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:44:22 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041858

Secondary Accession Numbers

HMDB41858

Metabolite Identification

Common Name

Clobenzorex

Description

Chemically, clobenzorex is an N-substituted amphetamine analog that is converted to d-amphetamine soon after ingestion. In commercial production, clobenzorex is supplied in 30 mg doses as the hydrochloride salt in green-tinted capsules. The drug gained use as a prescription anorectic in the 1970s; however, adverse reactions were eventually observed, which led to the prohibition of clobenzorex in the United States and certain other countries. Clobenzorex (Asenlix, Dinintel, Finedal, Rexigen) is a stimulant drug of the phenethylamine and amphetamine chemical classes used as an appetite suppressant. The drug is legally distributed in Mexico under the trade name Asenlix by Aventis.

Structure

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

HMDB0041858
     RDKit          3D
Clobenzorex
 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.7277    1.5631    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5460    0.3369   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5490   -0.7375    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9474   -0.3487    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    0.2095    1.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9643    0.5772    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6044    0.3927   -0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9164   -0.1652   -1.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -0.5295   -1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7671   -0.2496    0.1028 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7804    0.6882   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483    0.1336   -0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330   -1.1261    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -1.5509    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8036   -0.7550    0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067    0.5092   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2110    0.9275   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318    2.5501   -1.1799 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1837    2.4250    0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5205    1.3976    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158    1.8419    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.6483   -1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -1.6084   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344   -1.0863    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1924    0.3792    2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5381    1.0262    1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6480    0.6992   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4508   -0.2967   -2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004   -0.9685   -1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -1.1862   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286    0.8631   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7123    1.6003    0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6263   -1.7505    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9790   -2.5554    0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413   -1.1056    0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3214    1.1562   -0.7678 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  9  4  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
M  END


  Mrv0541 09131211442D          

 18 19  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   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
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    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    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 13  1  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 10  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041858

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CC1=CC=CC=C1)NCC1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C16H18ClN/c1-13(11-14-7-3-2-4-8-14)18-12-15-9-5-6-10-16(15)17/h2-10,13,18H,11-12H2,1H3

> <INCHI_KEY>
LRXXRIXDSAEIOR-UHFFFAOYSA-N

> <FORMULA>
C16H18ClN

> <MOLECULAR_WEIGHT>
259.774

> <EXACT_MASS>
259.112777288

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.683795541959288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2-chlorophenyl)methyl](1-phenylpropan-2-yl)amine

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
4.565348669

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.166460463584928

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
77.8972

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-clobenzorex

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0041858
     RDKit          3D
Clobenzorex
 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.7277    1.5631    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5460    0.3369   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5490   -0.7375    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9474   -0.3487    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    0.2095    1.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9643    0.5772    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6044    0.3927   -0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9164   -0.1652   -1.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -0.5295   -1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7671   -0.2496    0.1028 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7804    0.6882   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483    0.1336   -0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330   -1.1261    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -1.5509    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8036   -0.7550    0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067    0.5092   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2110    0.9275   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318    2.5501   -1.1799 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1837    2.4250    0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5205    1.3976    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158    1.8419    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.6483   -1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -1.6084   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344   -1.0863    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1924    0.3792    2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5381    1.0262    1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6480    0.6992   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4508   -0.2967   -2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004   -0.9685   -1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -1.1862   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286    0.8631   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7123    1.6003    0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6263   -1.7505    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9790   -2.5554    0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413   -1.1056    0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3214    1.1562   -0.7678 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  9  4  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       5.335   9.240   0.000  0.00  0.00          Cl+0
HETATM   18  N   UNK     0       4.001   6.930   0.000  0.00  0.00           N+0
CONECT    1   13                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    3   14                                                       
CONECT    8    4   14                                                       
CONECT    9    5   15                                                       
CONECT   10    6   16                                                       
CONECT   11   13   14                                                       
CONECT   12   15   18                                                       
CONECT   13    1   11   18                                                  
CONECT   14    7    8   11                                                  
CONECT   15    9   12   16                                                  
CONECT   16   10   15   17                                                  
CONECT   17   16                                                            
CONECT   18   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0041858
HETATM    1  C1  UNL     1      -0.728   1.563   0.807  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.546   0.337  -0.056  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.549  -0.737   0.263  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.947  -0.349   0.083  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.649   0.209   1.122  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.964   0.577   0.967  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.604   0.393  -0.235  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.916  -0.165  -1.287  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.596  -0.529  -1.116  1.00  0.00           C  
HETATM   10  N1  UNL     1       0.767  -0.250   0.103  1.00  0.00           N  
HETATM   11  C10 UNL     1       1.780   0.688  -0.324  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.148   0.134  -0.183  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.433  -1.126   0.297  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.742  -1.551   0.389  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.804  -0.755   0.015  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.507   0.509  -0.466  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.211   0.927  -0.557  1.00  0.00           C  
HETATM   18 CL1  UNL     1       3.932   2.550  -1.180  1.00  0.00          CL  
HETATM   19  H1  UNL     1      -0.184   2.425   0.368  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.520   1.398   1.868  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.816   1.842   0.734  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.702   0.648  -1.110  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.293  -1.608  -0.407  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.334  -1.086   1.295  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.192   0.379   2.097  1.00  0.00           H  
HETATM   26  H8  UNL     1      -5.538   1.026   1.792  1.00  0.00           H  
HETATM   27  H9  UNL     1      -6.648   0.699  -0.310  1.00  0.00           H  
HETATM   28  H10 UNL     1      -5.451  -0.297  -2.218  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.100  -0.969  -1.985  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.847  -1.186  -0.302  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.629   0.863  -1.422  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.712   1.600   0.272  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.626  -1.751   0.588  1.00  0.00           H  
HETATM   34  H16 UNL     1       4.979  -2.555   0.771  1.00  0.00           H  
HETATM   35  H17 UNL     1       6.841  -1.106   0.095  1.00  0.00           H  
HETATM   36  H18 UNL     1       6.321   1.156  -0.768  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   10   22
CONECT    3    4   23   24
CONECT    4    5    5    9
CONECT    5    6   25
CONECT    6    7    7   26
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   29
CONECT   10   11   30
CONECT   11   12   31   32
CONECT   12   13   13   17
CONECT   13   14   33
CONECT   14   15   15   34
CONECT   15   16   35
CONECT   16   17   17   36
CONECT   17   18
END

HMDB0041858
     RDKit          3D
Clobenzorex
 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.7277    1.5631    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5460    0.3369   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5490   -0.7375    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9474   -0.3487    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    0.2095    1.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9643    0.5772    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6044    0.3927   -0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9164   -0.1652   -1.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -0.5295   -1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7671   -0.2496    0.1028 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7804    0.6882   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483    0.1336   -0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330   -1.1261    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -1.5509    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8036   -0.7550    0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067    0.5092   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2110    0.9275   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318    2.5501   -1.1799 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1837    2.4250    0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5205    1.3976    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158    1.8419    0.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.6483   -1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -1.6084   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344   -1.0863    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1924    0.3792    2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5381    1.0262    1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6480    0.6992   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4508   -0.2967   -2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004   -0.9685   -1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -1.1862   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286    0.8631   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7123    1.6003    0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6263   -1.7505    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9790   -2.5554    0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8413   -1.1056    0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3214    1.1562   -0.7678 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  9  4  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-N-(O-Chlorobenzyl)-alpha-methylphenethylamine	HMDB
Asenlix	HMDB
Benzenemethanamine, 2'-chloro, N-(1-methyl-2-phenylethyl)	HMDB
Dinintel	HMDB
Finedal	HMDB
Clobenzorex hydrochloride	HMDB
Clobenzorex, (+-)-isomer	HMDB

Chemical Formula

C₁₆H₁₈ClN

Average Molecular Weight

259.774

Monoisotopic Molecular Weight

259.112777288

IUPAC Name

[(2-chlorophenyl)methyl](1-phenylpropan-2-yl)amine

Traditional Name

(+-)-clobenzorex

CAS Registry Number

13364-32-4

SMILES

CC(CC1=CC=CC=C1)NCC1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C16H18ClN/c1-13(11-14-7-3-2-4-8-14)18-12-15-9-5-6-10-16(15)17/h2-10,13,18H,11-12H2,1H3

InChI Key

LRXXRIXDSAEIOR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Amphetamines and derivatives

Alternative Parents

Substituents

Amphetamine or derivatives
Phenylpropane
Benzylamine
Phenylmethylamine
Chlorobenzene
Aralkylamine
Halobenzene
Aryl chloride
Aryl halide
Secondary amine
Secondary aliphatic amine
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Organochloride
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041858)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	133 °C	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	4.27	ALOGPS
logP	4.57	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	9.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.9 m³·mol⁻¹	ChemAxon
Polarizability	28.68 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
DeepCCS	[M+H]+	154.711	30932474
DeepCCS	[M-H]-	152.353	30932474
DeepCCS	[M-2H]-	185.582	30932474
DeepCCS	[M+Na]+	160.804	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	156.7	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	163.7	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clobenzorex	CC(CC1=CC=CC=C1)NCC1=CC=CC=C1Cl	2744.8	Standard polar	33892256
Clobenzorex	CC(CC1=CC=CC=C1)NCC1=CC=CC=C1Cl	1983.5	Standard non polar	33892256
Clobenzorex	CC(CC1=CC=CC=C1)NCC1=CC=CC=C1Cl	1951.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Clobenzorex,1TMS,isomer #1	CC(CC1=CC=CC=C1)N(CC1=CC=CC=C1Cl)[Si](C)(C)C	2042.0	Semi standard non polar	33892256
Clobenzorex,1TMS,isomer #1	CC(CC1=CC=CC=C1)N(CC1=CC=CC=C1Cl)[Si](C)(C)C	2255.9	Standard non polar	33892256
Clobenzorex,1TBDMS,isomer #1	CC(CC1=CC=CC=C1)N(CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C	2276.2	Semi standard non polar	33892256
Clobenzorex,1TBDMS,isomer #1	CC(CC1=CC=CC=C1)N(CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C	2452.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clobenzorex GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ou-2910000000-2ce5259d834683f743ab	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clobenzorex GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clobenzorex 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 - Clobenzorex 10V, Positive-QTOF	splash10-03fr-0690000000-27479dd865efcbfcebb0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 20V, Positive-QTOF	splash10-004i-0910000000-8497762b42c89e3e13e3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 40V, Positive-QTOF	splash10-004i-6900000000-dbf46aac4ce7c9672c82	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 10V, Negative-QTOF	splash10-0a4i-0090000000-929786dc24fddb2bed66	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 20V, Negative-QTOF	splash10-0a4i-0390000000-896ee55895a9b4a9fcb3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 40V, Negative-QTOF	splash10-01ox-1900000000-7824e09d0a34e1bda43f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 10V, Negative-QTOF	splash10-0a4i-4090000000-505a2b4e1ce254fba7c5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 20V, Negative-QTOF	splash10-001i-9030000000-a1609b1ee7b87789622f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 40V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 10V, Positive-QTOF	splash10-03di-0190000000-0680a3eef7b2b956063d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 20V, Positive-QTOF	splash10-01tc-5970000000-e8543c6ad5d13fedb132	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenzorex 40V, Positive-QTOF	splash10-002f-9800000000-1083a362eda2025bf3ed	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

64732

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clobenzorex

METLIN ID

Not Available

PubChem Compound

71675

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

Not Available

Showing metabocard for Clobenzorex (HMDB0041858)

MOL for HMDB0041858 (Clobenzorex)

3D MOL for HMDB0041858 (Clobenzorex)

3D SDF for HMDB0041858 (Clobenzorex)

3D-SDF for HMDB0041858 (Clobenzorex)

PDB for HMDB0041858 (Clobenzorex)

3D PDB for HMDB0041858 (Clobenzorex)

SMILES for HMDB0041858 (Clobenzorex)

INCHI for HMDB0041858 (Clobenzorex)

Structure for HMDB0041858 (Clobenzorex)

3D Structure for HMDB0041858 (Clobenzorex)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra