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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:37:10 UTC

Update Date

2022-03-07 03:18:13 UTC

HMDB ID

HMDB0240224

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Chlorcyclizine

Description

Chlorcyclizine, also known as histachlorazine, 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, chlorcyclizine is involved in the chlorcyclizine h1-antihistamine action pathway. Chlorcyclizine 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 a significant number of articles have been published on Chlorcyclizine.

Structure

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

HMDB0240224
     RDKit          3D
Chlorcyclizine
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.8381   -0.3154    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5133    0.2003    0.2335 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -0.7638    0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253   -1.0186   -0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6449    0.1972   -0.4797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    0.3436    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1088   -0.9982    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4618   -1.6828    1.5651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050   -2.8871    1.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845   -3.3865    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256   -2.6905   -0.9788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3809   -1.4838   -0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    1.3440    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7948    0.9716    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380    1.8111    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5372    3.1241   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8374    4.2600   -0.5893 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130    3.5284   -0.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1653    2.6561   -0.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5711    1.2690   -0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9629    0.7047   -1.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3698   -0.2137    1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4031    0.2084   -0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8132   -1.3938   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376   -0.4672    1.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1133   -1.7215    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740   -1.7859    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7522   -1.5046   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    0.4827    1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2362   -1.2787    2.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988   -3.4556    2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8945   -4.3420    0.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2680   -3.1267   -1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046   -0.9475   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0305   -0.0773    0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8738    1.5205    0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    4.5557   -0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1514    3.0467   -0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166    1.8902   -1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    1.8395    0.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448    1.5879   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9201   -0.0002   -1.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  5 20  1  0
 20 21  1  0
 21  2  1  0
 12  7  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END


  Mrv1652309191700202D          

 21 23  0  0  0  0            999 V2000
    0.7576    0.3618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433   -0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    1.1903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6649    0.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7576    1.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748   -0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433   -0.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3852   -0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6649    1.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748    1.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    0.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964    1.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3852    1.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964    0.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8107    1.6031    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9092    1.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6649   -1.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7576   -1.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6649   -2.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7576   -2.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433   -2.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3 11  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12 13  2  0  0  0  0
 13  9  1  0  0  0  0
 14  8  2  0  0  0  0
 15 12  1  0  0  0  0
 16  3  1  0  0  0  0
 17  7  2  0  0  0  0
 18  7  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 19  2  0  0  0  0
 10  3  1  0  0  0  0
 14 12  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240224

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H21ClN2/c1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16/h2-10,18H,11-14H2,1H3

> <INCHI_KEY>
WFNAKBGANONZEQ-UHFFFAOYSA-N

> <FORMULA>
C18H21ClN2

> <MOLECULAR_WEIGHT>
300.826

> <EXACT_MASS>
300.139326389

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.88614496099698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(4-chlorophenyl)(phenyl)methyl]-4-methylpiperazine

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
4.150047025666667

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.628581289773091

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
89.73840000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorcyclizine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240224
     RDKit          3D
Chlorcyclizine
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.8381   -0.3154    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5133    0.2003    0.2335 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -0.7638    0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253   -1.0186   -0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6449    0.1972   -0.4797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    0.3436    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1088   -0.9982    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4618   -1.6828    1.5651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050   -2.8871    1.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845   -3.3865    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256   -2.6905   -0.9788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3809   -1.4838   -0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    1.3440    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7948    0.9716    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380    1.8111    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5372    3.1241   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8374    4.2600   -0.5893 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130    3.5284   -0.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1653    2.6561   -0.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5711    1.2690   -0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9629    0.7047   -1.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3698   -0.2137    1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4031    0.2084   -0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8132   -1.3938   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376   -0.4672    1.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1133   -1.7215    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740   -1.7859    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7522   -1.5046   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    0.4827    1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2362   -1.2787    2.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988   -3.4556    2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8945   -4.3420    0.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2680   -3.1267   -1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046   -0.9475   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0305   -0.0773    0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8738    1.5205    0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    4.5557   -0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1514    3.0467   -0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166    1.8902   -1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    1.8395    0.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448    1.5879   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9201   -0.0002   -1.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  5 20  1  0
 20 21  1  0
 21  2  1  0
 12  7  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  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       1.414   0.675   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.081  -0.062   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.086   2.222   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.241   0.675   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.414   2.222   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.753  -0.062   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.081  -1.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.586  -0.062   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.241   2.222   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.753   2.993   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.086   0.675   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.913   2.222   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.586   2.993   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.913   0.675   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -5.247   2.993   0.000  0.00  0.00          Cl+0
HETATM   16  C   UNK     0       5.431   2.993   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.241  -2.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.414  -2.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.241  -3.931   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.414  -3.931   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.081  -4.701   0.000  0.00  0.00           C+0
CONECT    1    2    5    6                                                  
CONECT    2    1    4    7                                                  
CONECT    3   11   16   10                                                  
CONECT    4    2    8    9                                                  
CONECT    5    1   10                                                       
CONECT    6    1   11                                                       
CONECT    7    2   17   18                                                  
CONECT    8    4   14                                                       
CONECT    9    4   13                                                       
CONECT   10    5    3                                                       
CONECT   11    3    6                                                       
CONECT   12   13   15   14                                                  
CONECT   13   12    9                                                       
CONECT   14    8   12                                                       
CONECT   15   12                                                            
CONECT   16    3                                                            
CONECT   17    7   19                                                       
CONECT   18    7   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   21                                                       
CONECT   21   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0240224
HETATM    1  C1  UNL     1       4.838  -0.315   0.099  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.513   0.200   0.233  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.565  -0.764   0.746  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.425  -1.019  -0.185  1.00  0.00           C  
HETATM    5  N2  UNL     1       0.645   0.197  -0.480  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.398   0.344   0.484  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.109  -0.998   0.447  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.462  -1.683   1.565  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.105  -2.887   1.422  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.384  -3.387   0.154  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.026  -2.690  -0.979  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.381  -1.484  -0.816  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.443   1.344   0.198  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.795   0.972   0.242  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.838   1.811   0.014  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.537   3.124  -0.283  1.00  0.00           C  
HETATM   17 CL1  UNL     1      -4.837   4.260  -0.589  1.00  0.00          CL  
HETATM   18  C15 UNL     1      -2.213   3.528  -0.336  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.165   2.656  -0.099  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.571   1.269  -0.625  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.963   0.705  -1.001  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.370  -0.214   1.089  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.403   0.208  -0.706  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.813  -1.394  -0.145  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.238  -0.467   1.744  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.113  -1.722   0.852  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.774  -1.786   0.326  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.752  -1.505  -1.124  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.064   0.483   1.484  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.236  -1.279   2.542  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.399  -3.456   2.284  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.894  -4.342   0.070  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.268  -3.127  -1.933  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.105  -0.947  -1.712  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.031  -0.077   0.481  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.874   1.521   0.049  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.966   4.556  -0.568  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.151   3.047  -0.146  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.317   1.890  -1.510  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.788   1.839   0.296  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.545   1.588  -1.351  1.00  0.00           H  
HETATM   42  H21 UNL     1       2.920  -0.000  -1.825  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   20
CONECT    6    7   13   29
CONECT    7    8    8   12
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   34
CONECT   13   14   14   19
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   17   18
CONECT   18   19   19   37
CONECT   19   38
CONECT   20   21   39   40
CONECT   21   41   42
END

HMDB0240224
     RDKit          3D
Chlorcyclizine
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.8381   -0.3154    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5133    0.2003    0.2335 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -0.7638    0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253   -1.0186   -0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6449    0.1972   -0.4797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979    0.3436    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1088   -0.9982    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4618   -1.6828    1.5651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050   -2.8871    1.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845   -3.3865    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256   -2.6905   -0.9788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3809   -1.4838   -0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    1.3440    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7948    0.9716    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380    1.8111    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5372    3.1241   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8374    4.2600   -0.5893 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130    3.5284   -0.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1653    2.6561   -0.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5711    1.2690   -0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9629    0.7047   -1.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3698   -0.2137    1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4031    0.2084   -0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8132   -1.3938   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376   -0.4672    1.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1133   -1.7215    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740   -1.7859    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7522   -1.5046   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    0.4827    1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2362   -1.2787    2.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988   -3.4556    2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8945   -4.3420    0.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2680   -3.1267   -1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046   -0.9475   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0305   -0.0773    0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8738    1.5205    0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    4.5557   -0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1514    3.0467   -0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166    1.8902   -1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    1.8395    0.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448    1.5879   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9201   -0.0002   -1.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  5 20  1  0
 20 21  1  0
 21  2  1  0
 12  7  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Histachlorazine	MeSH
Chlorcycline	MeSH
Chlorocyclizin	MeSH
Alergicide	HMDB
Chlorocycline	HMDB
(±)-Chlorcyclizine	HMDB
Compound 47-282	HMDB
Di-Paralen	HMDB
N-Methyl-N'-(4-chlorobenzhydryl)piperazine	HMDB
NSC 25246	HMDB
Perazyl	HMDB
Trihistan	HMDB, ChEMBL
Chlorcyclizine	HMDB
Di-paralene	ChEMBL, HMDB
Mantadil	ChEMBL, HMDB
Pruresidine	ChEMBL, HMDB

Chemical Formula

C₁₈H₂₁ClN₂

Average Molecular Weight

300.826

Monoisotopic Molecular Weight

300.139326389

IUPAC Name

1-[(4-chlorophenyl)(phenyl)methyl]-4-methylpiperazine

Traditional Name

chlorcyclizine

CAS Registry Number

82-93-9

SMILES

CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C18H21ClN2/c1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16/h2-10,18H,11-14H2,1H3

InChI Key

WFNAKBGANONZEQ-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
Chlorobenzene
Halobenzene
N-methylpiperazine
Aralkylamine
N-alkylpiperazine
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240224)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Chlorcyclizine H1-Antihistamine Action (PathBank: SMP0058931)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	173.374	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000781

Predicted Molecular Properties

Property	Value	Source
logP	4.16	ALOGPS
logP	4.15	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	7.63	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	3	ChemAxon
Refractivity	89.74 m³·mol⁻¹	ChemAxon
Polarizability	33.89 Å³	ChemAxon
Number of Rings	3	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]+	170.503	30932474
DeepCCS	[M-H]-	168.146	30932474
DeepCCS	[M-2H]-	201.031	30932474
DeepCCS	[M+Na]+	176.597	30932474
AllCCS	[M+H]+	170.1	32859911
AllCCS	[M+H-H2O]+	166.5	32859911
AllCCS	[M+NH4]+	173.4	32859911
AllCCS	[M+Na]+	174.3	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	175.2	32859911
AllCCS	[M+HCOO]-	174.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorcyclizine	CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	2976.1	Standard polar	33892256
Chlorcyclizine	CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	2260.7	Standard non polar	33892256
Chlorcyclizine	CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	2258.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Chlorcyclizine EI-B (Non-derivatized)	splash10-006t-9261000000-d789fa33e2113c522133	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorcyclizine EI-B (Non-derivatized)	splash10-006t-9261000000-d789fa33e2113c522133	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorcyclizine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-8790000000-55311c996650b7e8c280	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorcyclizine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-0udi-0090000000-b26de1d44bba1bbba71d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-0udi-0090000000-cd86d2a7b60fba9a8093	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-0udi-0490000000-d2ef728df7bda2d67974	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-014i-0920000000-6337d2bca22bf828e822	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-cb2916a03edaa19b1b71	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-26236f7b47a790c10e10	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-3c7d8992d76da5c7bd63	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-a5c6cf14866d0a23a877	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-02t9-2900000000-5462dc3ded9a8297443e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-0udi-0090000000-c4ac9541a144f323398e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-0uxr-0590000000-ce9f2e2451aeb092dd88	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-014i-0920000000-587c135265c1fbd939db	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-2788ec685444238cbb77	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-300ed2322e3d24ba24cd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-014i-0009000000-6b6c6de087e1c9ad671e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-0udl-1192000000-2e1124f2124d4e765271	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-0udl-1290000000-cf510eabf20fd368c6d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-0gdi-2890000000-77c12238ddf4cb2c7502	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOF	splash10-014i-1930000000-89c336a1c9b2a2f0a9b7	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorcyclizine 10V, Positive-QTOF	splash10-0udi-0019000000-cd18f1e6a9392e477758	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorcyclizine 20V, Positive-QTOF	splash10-0udi-1195000000-56f33fe9d96ff1da46d0	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorcyclizine 40V, Positive-QTOF	splash10-0udi-6980000000-931f090bcc929d51f9f7	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorcyclizine 10V, Negative-QTOF	splash10-0002-0090000000-897899954ed2f06ae95b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorcyclizine 20V, Negative-QTOF	splash10-0002-1090000000-4be8b22bd980ebc5f053	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorcyclizine 40V, Negative-QTOF	splash10-00mx-7590000000-e863060ef85ea8728681	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Chlorcyclizine 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

DB08936

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2609

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorcyclizine

METLIN ID

Not Available

PubChem Compound

2710

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

He S, Lin B, Chu V, Hu Z, Hu X, Xiao J, Wang AQ, Schweitzer CJ, Li Q, Imamura M, Hiraga N, Southall N, Ferrer M, Zheng W, Chayama K, Marugan JJ, Liang TJ: Repurposing of the antihistamine chlorcyclizine and related compounds for treatment of hepatitis C virus infection. Sci Transl Med. 2015 Apr 8;7(282):282ra49. doi: 10.1126/scitranslmed.3010286. [PubMed:25855495 ]

Showing metabocard for Chlorcyclizine (HMDB0240224)

MOL for HMDB0240224 (Chlorcyclizine)

3D MOL for HMDB0240224 (Chlorcyclizine)

3D SDF for HMDB0240224 (Chlorcyclizine)

3D-SDF for HMDB0240224 (Chlorcyclizine)

PDB for HMDB0240224 (Chlorcyclizine)

3D PDB for HMDB0240224 (Chlorcyclizine)

SMILES for HMDB0240224 (Chlorcyclizine)

INCHI for HMDB0240224 (Chlorcyclizine)

Structure for HMDB0240224 (Chlorcyclizine)

3D Structure for HMDB0240224 (Chlorcyclizine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra