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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:43:13 UTC

Update Date

2022-03-07 03:18:14 UTC

HMDB ID

HMDB0240243

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Homochlorcyclizine

Description

Homochlorcyclizine, also known as curosajin or homoclomine, 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, homochlorcyclizine is involved in the homochlorcyclizine h1-antihistamine action pathway. Homochlorcyclizine 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 Homochlorcyclizine.

Structure

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

HMDB0240243
     RDKit          3D
Homochlorcyclizine
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.8522   -0.5897    1.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508   -0.9450    0.6612 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -0.5587   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146   -1.1397   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244   -0.1777   -1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4293   -0.2683    0.2330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988    0.0309    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    1.4272    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743    2.1374   -0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5857    3.4693   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1684    4.1037    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461    3.4089    1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9374    2.0991    1.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931   -0.8822   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185   -0.3505   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -1.1982   -1.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7504   -2.5688   -1.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9543   -3.5767   -2.1305 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6171   -3.0897   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -2.2213   -0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2044   -0.9615    1.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -0.2632    1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5533   -1.4588    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7520   -0.2310    2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2936    0.2569    0.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2558   -1.0027   -1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676    0.5455   -0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8915   -2.1490   -0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2485   -1.1330   -2.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3758    0.8181   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -0.3692   -1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884   -0.1978    1.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7360    1.7418   -1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4450    4.0176   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735    5.1353    0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186    3.9311    2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0977    1.5784    2.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1855    0.7138   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8414   -0.7916   -1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4683   -4.1582   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -2.7027    0.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.0351    1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578   -0.8785    2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.2935    2.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248    0.7774    1.1089 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  1  0
 22  2  1  0
 13  8  1  0
 20 14  1  0
  1 23  1  0
  1 24  1  0
  1 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
  7 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
M  END

      96024734
  Mrv1652311211718552D          

 22 24  0  0  1  0            999 V2000
   16.9675  -11.1753    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.1680   -8.6142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7703   -6.8622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1461   -9.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8567   -9.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3990   -9.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8762  -10.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5682   -9.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9442   -8.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4574   -8.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6884   -9.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3979  -10.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2569  -10.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5454  -11.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2788   -9.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1857   -7.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3663   -7.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9768   -9.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6865  -11.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9276   -6.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9403  -10.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1894   -6.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2  4  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  3 16  1  0  0  0  0
  3 20  1  0  0  0  0
  3 22  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6 11  2  0  0  0  0
  6 12  1  0  0  0  0
  7 14  1  0  0  0  0
  8 15  2  0  0  0  0
  9 16  1  0  0  0  0
 10 17  1  0  0  0  0
 11 18  1  0  0  0  0
 12 19  2  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240243

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23ClN2/c1-21-12-5-13-22(15-14-21)19(16-6-3-2-4-7-16)17-8-10-18(20)11-9-17/h2-4,6-11,19H,5,12-15H2,1H3

> <INCHI_KEY>
WEUCDJCFJHYFRL-UHFFFAOYSA-N

> <FORMULA>
C19H23ClN2

> <MOLECULAR_WEIGHT>
314.86

> <EXACT_MASS>
314.1549764

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
35.22039261540979

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
4.210006764666667

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.627333818889282

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
94.6038

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
homochlorcyclizine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240243
     RDKit          3D
Homochlorcyclizine
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.8522   -0.5897    1.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508   -0.9450    0.6612 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -0.5587   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146   -1.1397   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244   -0.1777   -1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4293   -0.2683    0.2330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988    0.0309    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    1.4272    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743    2.1374   -0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5857    3.4693   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1684    4.1037    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461    3.4089    1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9374    2.0991    1.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931   -0.8822   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185   -0.3505   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -1.1982   -1.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7504   -2.5688   -1.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9543   -3.5767   -2.1305 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6171   -3.0897   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -2.2213   -0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2044   -0.9615    1.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -0.2632    1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5533   -1.4588    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7520   -0.2310    2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2936    0.2569    0.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2558   -1.0027   -1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676    0.5455   -0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8915   -2.1490   -0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2485   -1.1330   -2.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3758    0.8181   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -0.3692   -1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884   -0.1978    1.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7360    1.7418   -1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4450    4.0176   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735    5.1353    0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186    3.9311    2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0977    1.5784    2.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1855    0.7138   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8414   -0.7916   -1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4683   -4.1582   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -2.7027    0.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.0351    1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578   -0.8785    2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.2935    2.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248    0.7774    1.1089 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  1  0
 22  2  1  0
 13  8  1  0
 20 14  1  0
  1 23  1  0
  1 24  1  0
  1 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
  7 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
M  END

HEADER    PROTEIN                                 21-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:       96024734                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-17         0                                  
HETATM    1 Cl   UNK     0      31.673 -20.861   0.000  0.00  0.00          Cl+0
HETATM    2  N   UNK     0      26.447 -16.080   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      27.571 -12.809   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      26.406 -17.665   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.733 -18.447   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.011 -18.362   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.769 -20.032   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.061 -17.711   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.896 -15.593   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.120 -15.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.685 -17.580   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.009 -19.881   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.346 -20.078   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.018 -20.814   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.387 -18.493   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.347 -14.071   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.950 -13.767   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.357 -18.316   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.681 -20.617   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.998 -12.597   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.289 -19.795   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.354 -11.483   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2    4    9   10                                                  
CONECT    3   16   20   22                                                  
CONECT    4    2    5    6                                                  
CONECT    5    4    7    8                                                  
CONECT    6    4   11   12                                                  
CONECT    7    5   14                                                       
CONECT    8    5   15                                                       
CONECT    9    2   16                                                       
CONECT   10    2   17                                                       
CONECT   11    6   18                                                       
CONECT   12    6   19                                                       
CONECT   13    1   14   15                                                  
CONECT   14    7   13                                                       
CONECT   15    8   13                                                       
CONECT   16    3    9                                                       
CONECT   17   10   20                                                       
CONECT   18   11   21                                                       
CONECT   19   12   21                                                       
CONECT   20    3   17                                                       
CONECT   21   18   19                                                       
CONECT   22    3                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0240243
HETATM    1  C1  UNL     1       4.852  -0.590   1.138  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.551  -0.945   0.661  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.386  -0.559  -0.732  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.115  -1.140  -1.312  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.924  -0.178  -1.063  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.429  -0.268   0.233  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.899   0.031   0.566  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.339   1.427   0.438  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.174   2.137  -0.716  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.586   3.469  -0.827  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.168   4.104   0.222  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.346   3.409   1.397  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.937   2.099   1.495  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.893  -0.882  -0.098  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.018  -0.350  -0.678  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.951  -1.198  -1.300  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.750  -2.569  -1.337  1.00  0.00           C  
HETATM   18 CL1  UNL     1      -4.954  -3.577  -2.130  1.00  0.00          CL  
HETATM   19  C16 UNL     1      -2.617  -3.090  -0.751  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.700  -2.221  -0.136  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.204  -0.962   1.202  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.544  -0.263   1.452  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.553  -1.459   1.183  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.752  -0.231   2.200  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.294   0.257   0.537  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.256  -1.003  -1.274  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.368   0.546  -0.861  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.891  -2.149  -0.972  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.248  -1.133  -2.414  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.376   0.818  -1.248  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.207  -0.369  -1.892  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.988  -0.198   1.685  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.736   1.742  -1.618  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.445   4.018  -1.755  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.473   5.135   0.097  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.819   3.931   2.239  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.098   1.578   2.452  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.185   0.714  -0.655  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.841  -0.792  -1.760  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.468  -4.158  -0.785  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.836  -2.703   0.301  1.00  0.00           H  
HETATM   42  H20 UNL     1       1.354  -2.035   1.014  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.658  -0.878   2.188  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.838  -0.293   2.506  1.00  0.00           H  
HETATM   45  H23 UNL     1       2.425   0.777   1.109  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   22
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   21
CONECT    7    8   14   32
CONECT    8    9    9   13
CONECT    9   10   33
CONECT   10   11   11   34
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   37
CONECT   14   15   15   20
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18   19
CONECT   19   20   20   40
CONECT   20   41
CONECT   21   22   42   43
CONECT   22   44   45
END

HMDB0240243
     RDKit          3D
Homochlorcyclizine
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.8522   -0.5897    1.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508   -0.9450    0.6612 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -0.5587   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146   -1.1397   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244   -0.1777   -1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4293   -0.2683    0.2330 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988    0.0309    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    1.4272    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743    2.1374   -0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5857    3.4693   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1684    4.1037    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461    3.4089    1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9374    2.0991    1.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931   -0.8822   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185   -0.3505   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -1.1982   -1.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7504   -2.5688   -1.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9543   -3.5767   -2.1305 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6171   -3.0897   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -2.2213   -0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2044   -0.9615    1.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -0.2632    1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5533   -1.4588    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7520   -0.2310    2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2936    0.2569    0.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2558   -1.0027   -1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676    0.5455   -0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8915   -2.1490   -0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2485   -1.1330   -2.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3758    0.8181   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -0.3692   -1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884   -0.1978    1.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7360    1.7418   -1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4450    4.0176   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735    5.1353    0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186    3.9311    2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0977    1.5784    2.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1855    0.7138   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8414   -0.7916   -1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4683   -4.1582   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -2.7027    0.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.0351    1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578   -0.8785    2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.2935    2.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248    0.7774    1.1089 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  1  0
 22  2  1  0
 13  8  1  0
 20 14  1  0
  1 23  1  0
  1 24  1  0
  1 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
  7 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Curosajin	HMDB
(±)-homochlorcyclizine	HMDB
Homochlorocyclizine	HMDB
Homoclomine	HMDB
Homodamon	HMDB
Homorestar	HMDB
Lysilan	HMDB
N-(p-Chlorobenzhydryl)-n'-methylhomopiperazine	HMDB
NSC 25132	HMDB
SA 97	HMDB
Sankumin	HMDB
Wicron	HMDB
Homochlorcyclizine HCL	HMDB
Homochlorocyclizine hydrochloride	HMDB
Homochlorocyclizine monohydrochloride	HMDB
1-((4-Chlorophenyl)phenylmethyl)hexahydro-4-methyl-1H-1,4-diazepine	HMDB
Homochlorcyclizine	HMDB, MeSH

Chemical Formula

C₁₉H₂₃ClN₂

Average Molecular Weight

314.86

Monoisotopic Molecular Weight

314.1549764

IUPAC Name

1-[(4-chlorophenyl)(phenyl)methyl]-4-methyl-1,4-diazepane

Traditional Name

homochlorcyclizine

CAS Registry Number

848-53-3

SMILES

CN1CCCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C19H23ClN2/c1-21-12-5-13-22(15-14-21)19(16-6-3-2-4-7-16)17-8-10-18(20)11-9-17/h2-4,6-11,19H,5,12-15H2,1H3

InChI Key

WEUCDJCFJHYFRL-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
1,4-diazepane
Chlorobenzene
Diazepane
Halobenzene
Aralkylamine
Aryl chloride
Aryl halide
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240243)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Homochlorcyclizine H1-Antihistamine Action (PathBank: SMP0062795)

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	4.53	ALOGPS
logP	4.21	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	8.63	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	94.6 m³·mol⁻¹	ChemAxon
Polarizability	35.22 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
AllCCS	[M+H]+	174.233	31661259
AllCCS	[M-H]-	180.152	31661259
DeepCCS	[M+H]+	174.099	30932474
DeepCCS	[M-H]-	171.741	30932474
DeepCCS	[M-2H]-	204.626	30932474
DeepCCS	[M+Na]+	180.192	30932474
AllCCS	[M+H]+	174.2	32859911
AllCCS	[M+H-H2O]+	170.8	32859911
AllCCS	[M+NH4]+	177.4	32859911
AllCCS	[M+Na]+	178.3	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	179.9	32859911
AllCCS	[M+HCOO]-	179.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Homochlorcyclizine	CN1CCCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	3259.6	Standard polar	33892256
Homochlorcyclizine	CN1CCCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	2367.6	Standard non polar	33892256
Homochlorcyclizine	CN1CCCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	2366.2	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 - Homochlorcyclizine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homochlorcyclizine 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 - Homochlorcyclizine 10V, Positive-QTOF	splash10-014i-0029000000-8a61986cf6d60bf81cda	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 20V, Positive-QTOF	splash10-0gb9-3096000000-959bed2bb20cae706198	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 40V, Positive-QTOF	splash10-0udl-9240000000-e1c510f4600b8a191aa9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 10V, Negative-QTOF	splash10-03di-0009000000-dc2748d860fa60954b1d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 20V, Negative-QTOF	splash10-03di-0159000000-65f5c34b0b35e0ac26b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 40V, Negative-QTOF	splash10-02fx-5490000000-940d537678147878c1c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 10V, Positive-QTOF	splash10-014i-0039000000-e5538a12567efbc3dfa8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 20V, Positive-QTOF	splash10-0uxr-0094000000-a3c4471119f072f6e962	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 40V, Positive-QTOF	splash10-0udi-1290000000-05fb262b2cc10b1e2916	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 10V, Negative-QTOF	splash10-03di-0009000000-c54768588510ddbc9bef	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 20V, Negative-QTOF	splash10-0ik9-0089000000-970bf509629d7033eebd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homochlorcyclizine 40V, Negative-QTOF	splash10-0ik9-1491000000-b2affbdb4464c5870a0d	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
Homochlorcyclizine 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

3501

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Homochlorcyclizine

METLIN ID

Not Available

PubChem Compound

3627

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

Suzuki A, Yasui-Furukori N, Mihara K, Kondo T, Furukori H, Inoue Y, Kaneko S, Otani K: Histamine H1-receptor antagonists, promethazine and homochlorcyclizine, increase the steady-state plasma concentrations of haloperidol and reduced haloperidol. Ther Drug Monit. 2003 Apr;25(2):192-6. [PubMed:12657913 ]

Showing metabocard for Homochlorcyclizine (HMDB0240243)

MOL for HMDB0240243 (Homochlorcyclizine)

3D MOL for HMDB0240243 (Homochlorcyclizine)

3D SDF for HMDB0240243 (Homochlorcyclizine)

3D-SDF for HMDB0240243 (Homochlorcyclizine)

PDB for HMDB0240243 (Homochlorcyclizine)

3D PDB for HMDB0240243 (Homochlorcyclizine)

SMILES for HMDB0240243 (Homochlorcyclizine)

INCHI for HMDB0240243 (Homochlorcyclizine)

Structure for HMDB0240243 (Homochlorcyclizine)

3D Structure for HMDB0240243 (Homochlorcyclizine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra