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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:38:11 UTC

Update Date

2022-03-07 03:18:13 UTC

HMDB ID

HMDB0240227

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phenbenzamine

Description

Phenbenzamine, also known as antergan or viternum, belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine. In humans, phenbenzamine is involved in the phenbenzamine h1-antihistamine action pathway. Phenbenzamine 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 Phenbenzamine.

Structure

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

HMDB0240227
     RDKit          3D
Phenbenzamine
 41 42  0  0  0  0  0  0  0  0999 V2000
   -4.4511   -1.3752   -0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8112   -0.5542    0.1514 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0035   -1.2804    1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3907   -0.6116   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402    0.2408    0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140    0.1816    0.5642 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4571   -1.0699    0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8434   -1.0914    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9072   -0.7377    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2197   -0.7578    0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4937   -1.1376   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4284   -1.4936   -1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352   -1.4748   -1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    1.3592    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7800    2.3627    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4144    3.5316    0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6802    3.6927   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177    2.6986   -1.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    1.5793   -1.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7178   -2.0244   -1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9284   -0.7584   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1901   -2.0909   -0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686   -0.6096    2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9741   -1.8179    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2122   -2.0499    1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -0.2174   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -1.6975   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.1873    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397    1.2729    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1262   -1.8665    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871   -1.2753    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7157   -0.4374    2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0588   -0.4738    1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5269   -1.1557   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103   -1.7922   -2.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2658   -1.7500   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5860    2.2725    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    4.3117    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1796    4.6146   -1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449    2.8569   -2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249    0.8133   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13  8  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv1652309191719362D          

 19 20  0  0  0  0            999 V2000
   -3.4149    1.3053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    1.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1294    1.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4149    0.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860    1.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715    1.7178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715    2.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5571    1.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5571    2.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1573    2.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718    2.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8719    3.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1574    4.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570    3.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570    0.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1574    0.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718    0.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8719    1.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1573    1.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0  0  0  0
  7  9  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
  9 10  2  0  0  0  0
 14  9  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  8 15  2  0  0  0  0
 19  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240227

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCN(CC1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2/c1-18(2)13-14-19(17-11-7-4-8-12-17)15-16-9-5-3-6-10-16/h3-12H,13-15H2,1-2H3

> <INCHI_KEY>
CHOBRHHOYQKCOU-UHFFFAOYSA-N

> <FORMULA>
C17H22N2

> <MOLECULAR_WEIGHT>
254.377

> <EXACT_MASS>
254.178298716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.75134986895668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-benzyl-N-[2-(dimethylamino)ethyl]aniline

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
3.8244073143333326

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.902668921407775

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
83.11830000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-benzyl-N-[2-(dimethylamino)ethyl]aniline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240227
     RDKit          3D
Phenbenzamine
 41 42  0  0  0  0  0  0  0  0999 V2000
   -4.4511   -1.3752   -0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8112   -0.5542    0.1514 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0035   -1.2804    1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3907   -0.6116   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402    0.2408    0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140    0.1816    0.5642 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4571   -1.0699    0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8434   -1.0914    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9072   -0.7377    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2197   -0.7578    0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4937   -1.1376   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4284   -1.4936   -1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352   -1.4748   -1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    1.3592    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7800    2.3627    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4144    3.5316    0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6802    3.6927   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177    2.6986   -1.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    1.5793   -1.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7178   -2.0244   -1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9284   -0.7584   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1901   -2.0909   -0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686   -0.6096    2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9741   -1.8179    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2122   -2.0499    1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -0.2174   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -1.6975   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.1873    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397    1.2729    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1262   -1.8665    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871   -1.2753    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7157   -0.4374    2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0588   -0.4738    1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5269   -1.1557   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103   -1.7922   -2.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2658   -1.7500   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5860    2.2725    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    4.3117    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1796    4.6146   -1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449    2.8569   -2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249    0.8133   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13  8  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 19-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-SEP-17         0                                  
HETATM    1  N   UNK     0      -6.374   2.437   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -5.041   3.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.708   3.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.374   0.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.707   2.437   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.373   3.207   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -2.373   4.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.040   2.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.040   5.517   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.294   4.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.627   5.517   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.628   7.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.294   7.827   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.040   7.057   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.040   0.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.294   0.127   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.627   0.896   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.628   2.436   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.294   3.207   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    5    1                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    9    6                                                       
CONECT    8   15   19    6                                                  
CONECT    9    7   10   14                                                  
CONECT   10   11    9                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   16    8                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    8                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0240227
HETATM    1  C1  UNL     1      -4.451  -1.375  -0.877  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.811  -0.554   0.151  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.004  -1.280   1.417  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.391  -0.612  -0.136  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.640   0.241   0.860  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.214   0.182   0.564  1.00  0.00           N  
HETATM    7  C5  UNL     1       0.457  -1.070   0.784  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.843  -1.091   0.284  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.907  -0.738   1.073  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.220  -0.758   0.590  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.494  -1.138  -0.705  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.428  -1.494  -1.500  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.135  -1.475  -1.029  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.411   1.359   0.080  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.780   2.363   0.966  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.414   3.532   0.526  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.680   3.693  -0.819  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.318   2.699  -1.718  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.704   1.579  -1.250  1.00  0.00           C  
HETATM   20  H1  UNL     1      -3.718  -2.024  -1.407  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.928  -0.758  -1.657  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.190  -2.091  -0.429  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.969  -0.610   2.296  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.974  -1.818   1.330  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.212  -2.050   1.514  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.162  -0.217  -1.139  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.122  -1.697  -0.044  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.841  -0.187   1.884  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.040   1.273   0.810  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.126  -1.866   0.275  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.387  -1.275   1.874  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.716  -0.437   2.091  1.00  0.00           H  
HETATM   33  H14 UNL     1       5.059  -0.474   1.227  1.00  0.00           H  
HETATM   34  H15 UNL     1       5.527  -1.156  -1.088  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.610  -1.792  -2.511  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.266  -1.750  -1.628  1.00  0.00           H  
HETATM   37  H18 UNL     1       0.586   2.273   2.021  1.00  0.00           H  
HETATM   38  H19 UNL     1       1.701   4.312   1.213  1.00  0.00           H  
HETATM   39  H20 UNL     1       2.180   4.615  -1.153  1.00  0.00           H  
HETATM   40  H21 UNL     1       1.545   2.857  -2.783  1.00  0.00           H  
HETATM   41  H22 UNL     1       0.425   0.813  -1.962  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4
CONECT    3   23   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   14
CONECT    7    8   30   31
CONECT    8    9    9   13
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12   34
CONECT   12   13   13   35
CONECT   13   36
CONECT   14   15   15   19
CONECT   15   16   37
CONECT   16   17   17   38
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   41
END

HMDB0240227
     RDKit          3D
Phenbenzamine
 41 42  0  0  0  0  0  0  0  0999 V2000
   -4.4511   -1.3752   -0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8112   -0.5542    0.1514 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0035   -1.2804    1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3907   -0.6116   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402    0.2408    0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140    0.1816    0.5642 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4571   -1.0699    0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8434   -1.0914    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9072   -0.7377    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2197   -0.7578    0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4937   -1.1376   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4284   -1.4936   -1.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352   -1.4748   -1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    1.3592    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7800    2.3627    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4144    3.5316    0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6802    3.6927   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177    2.6986   -1.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    1.5793   -1.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7178   -2.0244   -1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9284   -0.7584   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1901   -2.0909   -0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686   -0.6096    2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9741   -1.8179    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2122   -2.0499    1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -0.2174   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -1.6975   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.1873    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397    1.2729    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1262   -1.8665    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871   -1.2753    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7157   -0.4374    2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0588   -0.4738    1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5269   -1.1557   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103   -1.7922   -2.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2658   -1.7500   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5860    2.2725    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    4.3117    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1796    4.6146   -1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449    2.8569   -2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249    0.8133   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13  8  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2339 RP	HMDB
Antergan	HMDB
Bridal	HMDB
Dimetina	HMDB
Lergitin	HMDB
N-Benzyl-n',n'-dimethyl-N-phenylethylenediamine	HMDB
PM 245	HMDB
Viternum	HMDB
Cyproheptadine	HMDB
Peritol	HMDB
Dihexazin	HMDB
Periactin	HMDB
Phenbenzamine	HMDB

Chemical Formula

C₁₇H₂₂N₂

Average Molecular Weight

254.377

Monoisotopic Molecular Weight

254.178298716

IUPAC Name

N-benzyl-N-[2-(dimethylamino)ethyl]aniline

Traditional Name

N-benzyl-N-[2-(dimethylamino)ethyl]aniline

CAS Registry Number

961-71-7

SMILES

CN(C)CCN(CC1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H22N2/c1-18(2)13-14-19(17-11-7-4-8-12-17)15-16-9-5-3-6-10-16/h3-12H,13-15H2,1-2H3

InChI Key

CHOBRHHOYQKCOU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylbenzamines

Alternative Parents

Substituents

Phenylbenzamine
Aniline or substituted anilines
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Benzylamine
Aralkylamine
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

Exogenous (HMDB: HMDB0240227)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Phenbenzamine H1-Antihistamine Action (PathBank: SMP0059702)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.78	ALOGPS
logP	3.82	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	8.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.12 m³·mol⁻¹	ChemAxon
Polarizability	30.75 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]-	167.276	31661259
AllCCS	[M+H]+	159.389	31661259
DeepCCS	[M+H]+	160.054	30932474
DeepCCS	[M-H]-	157.696	30932474
DeepCCS	[M-2H]-	190.582	30932474
DeepCCS	[M+Na]+	166.147	30932474
AllCCS	[M+H]+	159.4	32859911
AllCCS	[M+H-H2O]+	155.6	32859911
AllCCS	[M+NH4]+	162.9	32859911
AllCCS	[M+Na]+	163.9	32859911
AllCCS	[M-H]-	167.3	32859911
AllCCS	[M+Na-2H]-	167.1	32859911
AllCCS	[M+HCOO]-	167.0	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.	5.03 minutes	32390414
Predicted by Siyang on May 30, 2022	11.1673 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.02 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1117.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	268.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	374.8 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	392.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	455.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	998.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	267.1 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	1205.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	243.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	326.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	335.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	315.8 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	7.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenbenzamine	CN(C)CCN(CC1=CC=CC=C1)C1=CC=CC=C1	2624.8	Standard polar	33892256
Phenbenzamine	CN(C)CCN(CC1=CC=CC=C1)C1=CC=CC=C1	1981.4	Standard non polar	33892256
Phenbenzamine	CN(C)CCN(CC1=CC=CC=C1)C1=CC=CC=C1	1963.9	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 - Phenbenzamine 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 - Phenbenzamine 10V, Positive-QTOF	splash10-0a4i-4090000000-70e24910df56da2bc8c6	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 20V, Positive-QTOF	splash10-006x-9020000000-8be29ee1402c65f03acd	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 40V, Positive-QTOF	splash10-0006-9000000000-3e076c4e54e6ec3d4098	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 10V, Negative-QTOF	splash10-0udi-0090000000-eb7c98d3ee27a8791371	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 20V, Negative-QTOF	splash10-0udi-1290000000-1bcdc626772405d2a5a2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 40V, Negative-QTOF	splash10-004i-9700000000-4e0e6fe5eb1ea2764454	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 10V, Negative-QTOF	splash10-0udi-0190000000-8f5e498bade72e89484d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 20V, Negative-QTOF	splash10-0f89-6930000000-4a0caa92f68cc46f0094	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 40V, Negative-QTOF	splash10-0059-6900000000-ed1c977753a4d1bfbb52	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 10V, Positive-QTOF	splash10-0a4i-0090000000-720dd99a0e66142a4884	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 20V, Positive-QTOF	splash10-052f-9060000000-7a292b63f84fd19ba1a2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenbenzamine 40V, Positive-QTOF	splash10-0a4i-9000000000-386725c19c78a2120b29	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Phenbenzamine 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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13155

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenbenzamine

METLIN ID

Not Available

PubChem Compound

13751

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

Wang XY, Lim-Jurado M, Prepageran N, Tantilipikorn P, Wang de Y: Treatment of allergic rhinitis and urticaria: a review of the newest antihistamine drug bilastine. Ther Clin Risk Manag. 2016 Apr 13;12:585-97. doi: 10.2147/TCRM.S105189. eCollection 2016. [PubMed:27110120 ]

Showing metabocard for Phenbenzamine (HMDB0240227)

MOL for HMDB0240227 (Phenbenzamine)

3D MOL for HMDB0240227 (Phenbenzamine)

3D SDF for HMDB0240227 (Phenbenzamine)

3D-SDF for HMDB0240227 (Phenbenzamine)

PDB for HMDB0240227 (Phenbenzamine)

3D PDB for HMDB0240227 (Phenbenzamine)

SMILES for HMDB0240227 (Phenbenzamine)

INCHI for HMDB0240227 (Phenbenzamine)

Structure for HMDB0240227 (Phenbenzamine)

3D Structure for HMDB0240227 (Phenbenzamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra