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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:36:33 UTC

Update Date

2022-03-07 03:18:13 UTC

HMDB ID

HMDB0240223

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Chlorphenoxamine

Description

Chlorphenoxamine, also known as systral or phenoxene, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. In humans, chlorphenoxamine is involved in the chlorphenoxamine h1-antihistamine action pathway. Chlorphenoxamine 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 Chlorphenoxamine.

Structure

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

HMDB0240223
     RDKit          3D
Chlorphenoxamine
 43 44  0  0  0  0  0  0  0  0999 V2000
    5.0869    0.2960   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8637   -0.4877   -0.6499 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7785   -1.5123    0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7596    0.4387   -0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282   -0.3114   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349    0.6110   -0.5184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    0.0940   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999   -0.6133   -1.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    1.2361   -0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3803    2.5334   -0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2612    3.6052   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6058    3.3624   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0635    2.0869   -0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1614    1.0218   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1542   -0.7770    0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9888   -0.3769    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723   -1.1947    2.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392   -2.4630    2.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1215   -3.5585    4.0543 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9182   -2.9013    1.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6239   -2.0533    0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8833    1.2737   -0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958   -0.2536   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3870    0.5481   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0877   -1.2589    1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772   -1.8208    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196   -2.4112   -0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774    1.0506    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.1024   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3886   -1.1467    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -0.7653   -1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693    0.0982   -2.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -0.7576   -2.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578   -1.5781   -1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    2.7568   -0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9062    4.6197   -0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2806    4.1991   -0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1222    1.8936   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5388    0.0152   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164    0.6349    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.8984    3.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889   -3.9076    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7772   -2.4300   -0.6237 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 14  9  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
 21 43  1  0
M  END


  Mrv1652309181721572D          

 21 22  0  0  0  0            999 V2000
    0.1105    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1269    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1269    3.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9519    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9519    3.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    3.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    3.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1894    4.3164    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    4.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 14 13  1  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18  1  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240223

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H22ClNO/c1-18(21-14-13-20(2)3,15-7-5-4-6-8-15)16-9-11-17(19)12-10-16/h4-12H,13-14H2,1-3H3

> <INCHI_KEY>
KKHPNPMTPORSQE-UHFFFAOYSA-N

> <FORMULA>
C18H22ClNO

> <MOLECULAR_WEIGHT>
303.826

> <EXACT_MASS>
303.138992038

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.03136075683058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl}dimethylamine

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
4.397809001333334

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.866470050489616

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
89.571

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
systral

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240223
     RDKit          3D
Chlorphenoxamine
 43 44  0  0  0  0  0  0  0  0999 V2000
    5.0869    0.2960   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8637   -0.4877   -0.6499 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7785   -1.5123    0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7596    0.4387   -0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282   -0.3114   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349    0.6110   -0.5184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    0.0940   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999   -0.6133   -1.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    1.2361   -0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3803    2.5334   -0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2612    3.6052   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6058    3.3624   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0635    2.0869   -0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1614    1.0218   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1542   -0.7770    0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9888   -0.3769    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723   -1.1947    2.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392   -2.4630    2.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1215   -3.5585    4.0543 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9182   -2.9013    1.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6239   -2.0533    0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8833    1.2737   -0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958   -0.2536   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3870    0.5481   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0877   -1.2589    1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772   -1.8208    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196   -2.4112   -0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774    1.0506    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.1024   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3886   -1.1467    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -0.7653   -1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693    0.0982   -2.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -0.7576   -2.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578   -1.5781   -1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    2.7568   -0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9062    4.6197   -0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2806    4.1991   -0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1222    1.8936   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5388    0.0152   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164    0.6349    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.8984    3.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889   -3.9076    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7772   -2.4300   -0.6237 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 14  9  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 18-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-17         0                                  
HETATM    1  C   UNK     0       0.206   9.597   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.366   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.056   4.056   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.206   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   4.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.127   4.207   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   5.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.127   5.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.104   9.391   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.104   6.724   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.644   9.391   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.644   6.724   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.056   6.724   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.516   6.724   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.206   6.517   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   8.057   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.414   8.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.206   8.057   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      -5.954   8.057   0.000  0.00  0.00          Cl+0
HETATM   20  N   UNK     0       4.826   5.390   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       1.746   8.057   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   15                                                       
CONECT    8    6   15                                                       
CONECT    9   11   16                                                       
CONECT   10   12   16                                                       
CONECT   11    9   17                                                       
CONECT   12   10   17                                                       
CONECT   13   14   20                                                       
CONECT   14   13   21                                                       
CONECT   15    7    8   18                                                  
CONECT   16    9   10   18                                                  
CONECT   17   11   12   19                                                  
CONECT   18    1   15   16   21                                             
CONECT   19   17                                                            
CONECT   20    2    3   13                                                  
CONECT   21   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0240223
HETATM    1  C1  UNL     1       5.087   0.296  -0.564  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.864  -0.488  -0.650  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.779  -1.512   0.349  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.760   0.439  -0.546  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.428  -0.311  -0.622  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.435   0.611  -0.518  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.855   0.094  -0.555  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.000  -0.613  -1.886  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.812   1.236  -0.575  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.380   2.533  -0.422  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.261   3.605  -0.433  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.606   3.362  -0.602  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.063   2.087  -0.756  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.161   1.022  -0.742  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.154  -0.777   0.586  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.989  -0.377   1.893  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.272  -1.195   2.959  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.739  -2.463   2.730  1.00  0.00           C  
HETATM   19 CL1  UNL     1      -2.122  -3.559   4.054  1.00  0.00          CL  
HETATM   20  C17 UNL     1      -1.918  -2.901   1.450  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.624  -2.053   0.374  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.883   1.274  -0.046  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.896  -0.254  -0.026  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.387   0.548  -1.597  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.088  -1.259   1.188  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.777  -1.821   0.739  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.320  -2.411  -0.152  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.777   1.051   0.357  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.796   1.102  -1.445  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.389  -1.147   0.070  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.386  -0.765  -1.654  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.569   0.098  -2.651  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.068  -0.758  -2.137  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.458  -1.578  -1.914  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.318   2.757  -0.286  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.906   4.620  -0.310  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.281   4.199  -0.609  1.00  0.00           H  
HETATM   38  H17 UNL     1      -5.122   1.894  -0.889  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.539   0.015  -0.866  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.616   0.635   2.078  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.150  -0.898   3.990  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.289  -3.908   1.260  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.777  -2.430  -0.624  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4
CONECT    3   25   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7
CONECT    7    8    9   15
CONECT    8   32   33   34
CONECT    9   10   10   14
CONECT   10   11   35
CONECT   11   12   12   36
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   39
CONECT   15   16   16   21
CONECT   16   17   40
CONECT   17   18   18   41
CONECT   18   19   20
CONECT   20   21   21   42
CONECT   21   43
END

HMDB0240223
     RDKit          3D
Chlorphenoxamine
 43 44  0  0  0  0  0  0  0  0999 V2000
    5.0869    0.2960   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8637   -0.4877   -0.6499 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7785   -1.5123    0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7596    0.4387   -0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282   -0.3114   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4349    0.6110   -0.5184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    0.0940   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999   -0.6133   -1.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    1.2361   -0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3803    2.5334   -0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2612    3.6052   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6058    3.3624   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0635    2.0869   -0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1614    1.0218   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1542   -0.7770    0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9888   -0.3769    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723   -1.1947    2.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392   -2.4630    2.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1215   -3.5585    4.0543 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9182   -2.9013    1.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6239   -2.0533    0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8833    1.2737   -0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958   -0.2536   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3870    0.5481   -1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0877   -1.2589    1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772   -1.8208    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196   -2.4112   -0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774    1.0506    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.1024   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3886   -1.1467    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -0.7653   -1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693    0.0982   -2.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -0.7576   -2.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578   -1.5781   -1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    2.7568   -0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9062    4.6197   -0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2806    4.1991   -0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1222    1.8936   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5388    0.0152   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164    0.6349    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.8984    3.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889   -3.9076    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7772   -2.4300   -0.6237 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 14  9  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Chlorphenoxamine hydrochloride	HMDB
Systral	HMDB
Phenoxene	HMDB
p-Chloro-α-methyldiphenhydramine	HMDB
p-Chloro-alpha-methyldiphenhydramine	HMDB
Chlorphenoxamine	HMDB

Chemical Formula

C₁₈H₂₂ClNO

Average Molecular Weight

303.826

Monoisotopic Molecular Weight

303.138992038

IUPAC Name

{2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl}dimethylamine

Traditional Name

systral

CAS Registry Number

77-38-3

SMILES

CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C18H22ClNO/c1-18(21-14-13-20(2)3,15-7-5-4-6-8-15)16-9-11-17(19)12-10-16/h4-12H,13-14H2,1-3H3

InChI Key

KKHPNPMTPORSQE-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Benzylether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Tertiary aliphatic amine
Tertiary amine
Ether
Dialkyl ether
Organochloride
Organohalogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240223)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Chlorphenoxamine H1-Antihistamine Action (PathBank: SMP0058903)

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	4.45	ALOGPS
logP	4.4	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	89.57 m³·mol⁻¹	ChemAxon
Polarizability	34.03 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]+	168.94	31661259
AllCCS	[M-H]-	175.765	31661259
DeepCCS	[M+H]+	174.071	30932474
DeepCCS	[M-H]-	171.713	30932474
DeepCCS	[M-2H]-	204.599	30932474
DeepCCS	[M+Na]+	180.164	30932474
AllCCS	[M+H]+	168.9	32859911
AllCCS	[M+H-H2O]+	165.4	32859911
AllCCS	[M+NH4]+	172.2	32859911
AllCCS	[M+Na]+	173.1	32859911
AllCCS	[M-H]-	175.8	32859911
AllCCS	[M+Na-2H]-	175.6	32859911
AllCCS	[M+HCOO]-	175.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.37 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6945 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.94 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1440.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	279.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	192.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	109.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	477.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	528.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	456.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	998.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	381.7 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	1285.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	252.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	286.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	251.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorphenoxamine	CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	2800.8	Standard polar	33892256
Chlorphenoxamine	CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	2154.4	Standard non polar	33892256
Chlorphenoxamine	CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	2082.9	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 - Chlorphenoxamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-9270000000-0d583146e734001ab2de	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorphenoxamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorphenoxamine 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 - Chlorphenoxamine 10V, Positive-QTOF	splash10-0udi-1019000000-8bf961c8b305d3d2cd18	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 20V, Positive-QTOF	splash10-0uk9-6197000000-e3bac9734f5caf72ae3f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 40V, Positive-QTOF	splash10-00xr-9330000000-4695fc77e61182f67db6	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 10V, Negative-QTOF	splash10-0udi-1029000000-4903b35120dfe8c709ac	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 20V, Negative-QTOF	splash10-0udi-2289000000-24171bc1dfc4aff63337	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 40V, Negative-QTOF	splash10-02w9-6790000000-ff8ef12e4f5540ab3a53	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 10V, Negative-QTOF	splash10-001i-0092000000-473936b9be1c1340c42e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 20V, Negative-QTOF	splash10-0uxr-2930000000-c505b9c8940792445776	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 40V, Negative-QTOF	splash10-014i-1790000000-c7003c2131a3eed98d97	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 10V, Positive-QTOF	splash10-014i-0092000000-a380a0b11a2a9f81a5d9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 20V, Positive-QTOF	splash10-014i-1190000000-bc07e4f6573ce6b17560	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorphenoxamine 40V, Positive-QTOF	splash10-00di-9220000000-ca728e674e0edc2236ea	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Chlorphenoxamine 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

DB09007

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6230

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorphenoxamine

METLIN ID

Not Available

PubChem Compound

6475

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

BAZEX A, DUPRE A, CHRISTOL B: [Trial treatment of urticaria with chlorphenoxamine]. Clinique (Paris). 1963 Jul-Aug;58:447-50. [PubMed:13967113 ]

Showing metabocard for Chlorphenoxamine (HMDB0240223)

MOL for HMDB0240223 (Chlorphenoxamine)

3D MOL for HMDB0240223 (Chlorphenoxamine)

3D SDF for HMDB0240223 (Chlorphenoxamine)

3D-SDF for HMDB0240223 (Chlorphenoxamine)

PDB for HMDB0240223 (Chlorphenoxamine)

3D PDB for HMDB0240223 (Chlorphenoxamine)

SMILES for HMDB0240223 (Chlorphenoxamine)

INCHI for HMDB0240223 (Chlorphenoxamine)

Structure for HMDB0240223 (Chlorphenoxamine)

3D Structure for HMDB0240223 (Chlorphenoxamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra