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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014507

Secondary Accession Numbers

HMDB14507

Metabolite Identification

Common Name

Clozapine

Description

A tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent. [PubChem]

Structure

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

HMDB0014507
     RDKit          3D
Clozapine
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.4937    1.0930    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9645    0.5584   -0.4008 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4607   -0.7713   -0.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1263   -0.7206    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386    0.1103   -0.3337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    0.0132   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7230    1.0340    0.4963 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0487    1.2808    0.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626    2.6263    1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243    3.0060    1.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528    4.6967    2.0198 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5362    2.0710    1.6820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3257    0.7497    1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    0.3513    0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0345   -1.0439    0.6818 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0653   -1.6718   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5120   -2.8555   -0.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960   -3.5837   -1.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4397   -3.1343   -1.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0402   -1.9206   -1.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029   -1.2234   -0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    1.0169   -1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1386    1.4521   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5545    0.7207    0.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    2.2013    0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    0.7688    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3674   -1.2145   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2017   -1.3426    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196   -1.7386    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2424   -0.2471    1.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    3.3217    1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5182    2.3971    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1033   -0.0136    1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7553   -1.6545    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4782   -3.1994   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394   -4.5417   -1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2174   -3.6794   -2.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0216   -1.5543   -1.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5876    0.6416   -2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0464    1.9264   -1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413    2.4314   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5976    1.6419   -2.1407 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
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 17 18  1  0
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  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 14  8  1  0
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  1 24  1  0
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 22 40  1  0
 23 41  1  0
 23 42  1  0
M  END

 
  Mrv0541 02231214372D          
 
 23 26  0  0  0  0            999 V2000
   13.5847   -8.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0879   -7.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2856   -6.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0296   -6.3036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4141   -8.1146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7692   -6.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9382   -7.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6915   -6.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8997   -6.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7020   -7.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2962   -7.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7236   -7.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3396   -7.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1706   -6.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3852   -6.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2104   -8.8370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3835   -8.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9700   -9.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3835  -10.2693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2104  -10.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6238   -9.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1389   -7.4474    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.9664  -10.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  1  5  2  0  0  0  0
  4  6  1  0  0  0  0
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 16 21  1  0  0  0  0
 13 22  1  0  0  0  0
 19 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014507

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H19ClN4/c1-22-8-10-23(11-9-22)18-14-4-2-3-5-15(14)20-16-7-6-13(19)12-17(16)21-18/h2-7,12,20H,8-11H2,1H3

> <INCHI_KEY>
QZUDBNBUXVUHMW-UHFFFAOYSA-N

> <FORMULA>
C18H19ClN4

> <MOLECULAR_WEIGHT>
326.823

> <EXACT_MASS>
326.129824335

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.76978422413783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-chloro-10-(4-methylpiperazin-1-yl)-2,9-diazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
3.400241024333333

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.900124965902936

> <JCHEM_PKA_STRONGEST_BASIC>
7.351009067472559

> <JCHEM_POLAR_SURFACE_AREA>
30.870000000000005

> <JCHEM_REFRACTIVITY>
97.35649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clozapine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014507
     RDKit          3D
Clozapine
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.4937    1.0930    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9645    0.5584   -0.4008 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4607   -0.7713   -0.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1263   -0.7206    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386    0.1103   -0.3337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    0.0132   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7230    1.0340    0.4963 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0487    1.2808    0.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626    2.6263    1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243    3.0060    1.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528    4.6967    2.0198 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5362    2.0710    1.6820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3257    0.7497    1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    0.3513    0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0345   -1.0439    0.6818 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0653   -1.6718   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5120   -2.8555   -0.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960   -3.5837   -1.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4397   -3.1343   -1.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0402   -1.9206   -1.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029   -1.2234   -0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    1.0169   -1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1386    1.4521   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5545    0.7207    0.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    2.2013    0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    0.7688    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3674   -1.2145   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2017   -1.3426    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196   -1.7386    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2424   -0.2471    1.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    3.3217    1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5182    2.3971    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1033   -0.0136    1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7553   -1.6545    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4782   -3.1994   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394   -4.5417   -1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2174   -3.6794   -2.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0216   -1.5543   -1.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5876    0.6416   -2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0464    1.9264   -1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413    2.4314   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5976    1.6419   -2.1407 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 14  8  1  0
 21 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      25.358 -15.119   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.431 -13.898   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.800 -12.403   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      26.189 -11.767   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      26.906 -15.147   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      27.569 -12.452   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.885 -13.959   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.691 -11.337   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.213 -11.764   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.844 -13.259   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.953 -14.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.351 -14.441   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.501 -13.412   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.185 -11.904   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.719 -11.423   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      24.659 -16.496   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      23.116 -16.496   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.344 -17.832   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      23.116 -19.169   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      24.659 -19.169   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.431 -17.832   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0      31.993 -13.902   0.000  0.00  0.00          Cl+0
HETATM   23  C   UNK     0      22.337 -20.517   0.000  0.00  0.00           C+0
CONECT    1    5    2   16                                                  
CONECT    2    3    1   11                                                  
CONECT    3    4    2    8                                                  
CONECT    4    3    6                                                       
CONECT    5    1    7                                                       
CONECT    6    4    7   15                                                  
CONECT    7    5    6   12                                                  
CONECT    8    3    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
CONECT   12    7   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14    6                                                       
CONECT   16    1   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   13                                                            
CONECT   23   19                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0014507
HETATM    1  C1  UNL     1       4.494   1.093   0.814  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.965   0.558  -0.401  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.461  -0.771  -0.278  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.126  -0.721   0.431  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.239   0.110  -0.334  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.152   0.013  -0.090  1.00  0.00           C  
HETATM    7  N3  UNL     1      -0.723   1.034   0.496  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.049   1.281   0.884  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.263   2.626   1.203  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.524   3.006   1.604  1.00  0.00           C  
HETATM   11 CL1  UNL     1      -3.853   4.697   2.020  1.00  0.00          CL  
HETATM   12  C8  UNL     1      -4.536   2.071   1.682  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.326   0.750   1.369  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.061   0.351   0.964  1.00  0.00           C  
HETATM   15  N4  UNL     1      -3.034  -1.044   0.682  1.00  0.00           N  
HETATM   16  C11 UNL     1      -2.065  -1.672  -0.169  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.512  -2.856  -0.663  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.696  -3.584  -1.504  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.440  -3.134  -1.852  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.040  -1.921  -1.356  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.803  -1.223  -0.520  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.719   1.017  -1.305  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.139   1.452  -1.145  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.554   0.721   0.900  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.505   2.201   0.824  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.986   0.769   1.729  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.367  -1.214  -1.266  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.202  -1.343   0.348  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.720  -1.739   0.653  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.242  -0.247   1.428  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.439   3.322   1.127  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.518   2.397   2.000  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.103  -0.014   1.420  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.755  -1.655   1.109  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.478  -3.199  -0.395  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.039  -4.542  -1.913  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.217  -3.679  -2.505  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.022  -1.554  -1.620  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.588   0.642  -2.341  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.046   1.926  -1.265  1.00  0.00           H  
HETATM   41  H18 UNL     1       3.141   2.431  -0.622  1.00  0.00           H  
HETATM   42  H19 UNL     1       3.598   1.642  -2.141  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   23
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   22
CONECT    6    7    7   21
CONECT    7    8
CONECT    8    9    9   14
CONECT    9   10   31
CONECT   10   11   12   12
CONECT   12   13   32
CONECT   13   14   14   33
CONECT   14   15
CONECT   15   16   34
CONECT   16   17   17   21
CONECT   17   18   35
CONECT   18   19   19   36
CONECT   19   20   37
CONECT   20   21   21   38
CONECT   22   23   39   40
CONECT   23   41   42
END

HMDB0014507
     RDKit          3D
Clozapine
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.4937    1.0930    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9645    0.5584   -0.4008 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4607   -0.7713   -0.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1263   -0.7206    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386    0.1103   -0.3337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    0.0132   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7230    1.0340    0.4963 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0487    1.2808    0.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626    2.6263    1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243    3.0060    1.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528    4.6967    2.0198 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5362    2.0710    1.6820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3257    0.7497    1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    0.3513    0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0345   -1.0439    0.6818 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0653   -1.6718   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5120   -2.8555   -0.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960   -3.5837   -1.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4397   -3.1343   -1.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0402   -1.9206   -1.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029   -1.2234   -0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    1.0169   -1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1386    1.4521   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5545    0.7207    0.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    2.2013    0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    0.7688    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3674   -1.2145   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2017   -1.3426    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196   -1.7386    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2424   -0.2471    1.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    3.3217    1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5182    2.3971    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1033   -0.0136    1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7553   -1.6545    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4782   -3.1994   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394   -4.5417   -1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2174   -3.6794   -2.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0216   -1.5543   -1.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5876    0.6416   -2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0464    1.9264   -1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413    2.4314   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5976    1.6419   -2.1407 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 14  8  1  0
 21 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Clozapin	ChEBI
Clozapina	ChEBI
Clozapinum	ChEBI
Clozaril	Kegg
Leponex	HMDB

Chemical Formula

C₁₈H₁₉ClN₄

Average Molecular Weight

326.823

Monoisotopic Molecular Weight

326.129824335

IUPAC Name

6-chloro-10-(4-methylpiperazin-1-yl)-2,9-diazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene

Traditional Name

clozapine

CAS Registry Number

5786-21-0

SMILES

CN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12

InChI Identifier

InChI=1S/C18H19ClN4/c1-22-8-10-23(11-9-22)18-14-4-2-3-5-15(14)20-16-7-6-13(19)12-17(16)21-18/h2-7,12,20H,8-11H2,1H3

InChI Key

QZUDBNBUXVUHMW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzodiazepines. Dibenzodiazepines are compounds containing a dibenzodiazepine moiety, which consists of two benzene connected by diazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

Dibenzodiazepines

Direct Parent

Dibenzodiazepines

Alternative Parents

Substituents

Dibenzodiazepine
1,4-benzodiazepine
N-methylpiperazine
N-alkylpiperazine
Aryl chloride
Aryl halide
1,4-diazinane
Imidolactam
Piperazine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Amidine
Secondary amine
Organic 1,3-dipolar compound
Azacycle
Carboxylic acid amidine
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:3766 )
organochlorine compound (CHEBI:3766 )
N-methylpiperazine (CHEBI:3766 )
benzodiazepine (CHEBI:3766 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014507)

Source

Exogenous

Exogenous (HMDB: HMDB0014507)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 - 184 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.19 g/L	Not Available
LogP	2.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	178.8	30932474
[M+H]+	Not Available	177.536	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000995

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	3.67	ALOGPS
logP	3.4	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.9	ChemAxon
pKa (Strongest Basic)	7.35	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	30.87 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	97.36 m³·mol⁻¹	ChemAxon
Polarizability	35.77 Å³	ChemAxon
Number of Rings	4	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-2H]-	201.583	30932474
DeepCCS	[M+Na]+	177.149	30932474
AllCCS	[M+H]+	175.7	32859911
AllCCS	[M+H-H2O]+	172.5	32859911
AllCCS	[M+NH4]+	178.6	32859911
AllCCS	[M+Na]+	179.5	32859911
AllCCS	[M-H]-	178.6	32859911
AllCCS	[M+Na-2H]-	178.0	32859911
AllCCS	[M+HCOO]-	177.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clozapine	CN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12	4119.6	Standard polar	33892256
Clozapine	CN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12	2903.2	Standard non polar	33892256
Clozapine	CN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12	2885.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Clozapine,1TMS,isomer #1	CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C)C3=CC=CC=C23)CC1	2802.3	Semi standard non polar	33892256
Clozapine,1TMS,isomer #1	CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C)C3=CC=CC=C23)CC1	2744.5	Standard non polar	33892256
Clozapine,1TMS,isomer #1	CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C)C3=CC=CC=C23)CC1	3933.8	Standard polar	33892256
Clozapine,1TBDMS,isomer #1	CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC1	2935.4	Semi standard non polar	33892256
Clozapine,1TBDMS,isomer #1	CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC1	2955.4	Standard non polar	33892256
Clozapine,1TBDMS,isomer #1	CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC1	4013.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clozapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-06r5-9064000000-0f31b1de88be42ac8381	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clozapine 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 - Clozapine LC-ESI-qTof , Positive-QTOF	splash10-00b9-0298000000-50d2ee0b52827fd1aee3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-qTof , Positive-QTOF	splash10-00di-2690000000-daaa74a4f85f5e8b5926	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-00di-0090000000-bc2ca4d5a76a5facf897	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-004i-0009000000-986bc19f7e7e8602d005	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-00b9-0049000000-d6315d4aeb74c251e939	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-00di-0090000000-27fd28450826291cc8c6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-00di-0290000000-474b25ea27690471db0f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-0006-0970000000-a58015260aaddb4245bd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-0006-0930000000-3ccfd048a34fdb4f594f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-004i-0009000000-7df53c42e3b1618bfdec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-004i-0049000000-7522cc8ebf988effc792	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-00di-0090000000-bd138be4ae488c201ed3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-00di-0190000000-68c8b78f304c38b7b7b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-0006-0980000000-a9dd724f32c02059c510	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-0006-0930000000-61c0f65f163824ddd594	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOF	splash10-00di-0090000000-da747a0572aa2c21683f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine , positive-QTOF	splash10-002f-0930000000-614883dbe075268cf23a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine , positive-QTOF	splash10-00b9-0298000000-50d2ee0b52827fd1aee3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clozapine , positive-QTOF	splash10-00di-2690000000-daaa74a4f85f5e8b5926	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clozapine 10V, Positive-QTOF	splash10-004i-0009000000-b771968b218f574a2031	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clozapine 20V, Positive-QTOF	splash10-004i-1049000000-24dab1e16fa5778e3f05	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clozapine 40V, Positive-QTOF	splash10-004i-2190000000-6b669cd26b101d106f1c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clozapine 10V, Negative-QTOF	splash10-004i-0009000000-178d40f752b4d092a8a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clozapine 20V, Negative-QTOF	splash10-004i-0029000000-5b7197f427b8cfdcdac2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clozapine 40V, Negative-QTOF	splash10-0006-4290000000-33f870d86d2adcc8f049	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00363	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00363	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00363

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10442628

KEGG Compound ID

C06924

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clozapine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

3766

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

Vaddadi KS, Soosai E, Vaddadi G: Low blood selenium concentrations in schizophrenic patients on clozapine. Br J Clin Pharmacol. 2003 Mar;55(3):307-9. [PubMed:12630982 ]
Alvir JM, Lieberman JA, Safferman AZ, Schwimmer JL, Schaaf JA: Clozapine-induced agranulocytosis. Incidence and risk factors in the United States. N Engl J Med. 1993 Jul 15;329(3):162-7. [PubMed:8515788 ]
Lane HY, Chang YC, Chang WH, Lin SK, Tseng YT, Jann MW: Effects of gender and age on plasma levels of clozapine and its metabolites: analyzed by critical statistics. J Clin Psychiatry. 1999 Jan;60(1):36-40. [PubMed:10074876 ]
Naheed M, Green B: Focus on clozapine. Curr Med Res Opin. 2001;17(3):223-9. [PubMed:11900316 ]

Showing metabocard for Clozapine (HMDB0014507)

MOL for HMDB0014507 (Clozapine)

3D MOL for HMDB0014507 (Clozapine)

3D SDF for HMDB0014507 (Clozapine)

3D-SDF for HMDB0014507 (Clozapine)

PDB for HMDB0014507 (Clozapine)

3D PDB for HMDB0014507 (Clozapine)

SMILES for HMDB0014507 (Clozapine)

INCHI for HMDB0014507 (Clozapine)

Structure for HMDB0014507 (Clozapine)

3D Structure for HMDB0014507 (Clozapine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra