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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:32:34 UTC

Update Date

2019-07-23 07:14:33 UTC

HMDB ID

HMDB0060536

Secondary Accession Numbers

HMDB60536

Metabolite Identification

Common Name

Norclozapine

Description

Norclozapine is the major metabolite of Clozapine. Clozapine is an atypical antipsychotic medication used in the treatment of schizophrenia, and is also sometimes used off-label for the treatment of bipolar disorder. Clozapine is extensively metabolized in the liver, via the cytochrome P450 system, to polar metabolites suitable for elimination in the urine and feces. The major metabolite, norclozapine (desmethyl-clozapine), is pharmacologically active. (Wikipedia )

Structure

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

HMDB0060536
     RDKit          3D
Norclozapine
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.8299   -4.6769   -1.7571 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4078   -3.0101   -1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4230   -2.0725   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0787   -0.7606   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940   -0.3981   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918   -1.3534   -0.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014   -2.6761   -1.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121   -1.1577   -0.5477 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -0.1340   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039   -0.2149    0.1277 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799    0.5807   -0.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720    0.5599   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3742   -0.7790   -0.0182 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4351   -1.7473    0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1924   -1.1045    1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566    1.1382    0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5580    1.8449    1.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1332    3.0550    1.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1278    3.5610    1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299    2.8249    0.7453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    1.6302    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6749    1.0109   -0.5248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487   -2.3304   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8416    0.0078   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131   -3.4172   -1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047    0.0485   -1.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262    1.5882   -0.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8606    0.9870    0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    1.2093   -0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205   -1.1147   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1210   -2.4371   -0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8641   -2.4010    1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -1.9598    1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402   -0.6368    2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377    1.4394    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136    3.6242    2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4867    4.4916    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261    3.1681    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4081    1.6125   -0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
  7  2  1  0
 15 10  1  0
 21 16  1  0
 22  5  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 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
M  END

[NO NAME]
  Mrv0541 04171216562D          
Created with ChemWriter - http://chemwriter.com
 22 25  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
  3  4  1  0  0  0  0
  1  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  3  1  0  0  0  0
  5  7  1  0  0  0  0
  1  2  1  0  0  0  0
  6  7  1  0  0  0  0
  3  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  2 11  2  0  0  0  0
  7 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  6 15  2  0  0  0  0
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 13 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060536

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=C2NC3=CC=CC=C3C(=NC2=C1)N1CCNCC1

> <INCHI_IDENTIFIER>
InChI=1S/C17H17ClN4/c18-12-5-6-15-16(11-12)21-17(22-9-7-19-8-10-22)13-3-1-2-4-14(13)20-15/h1-6,11,19-20H,7-10H2

> <INCHI_KEY>
JNNOSTQEZICQQP-UHFFFAOYSA-N

> <FORMULA>
C17H17ClN4

> <MOLECULAR_WEIGHT>
312.797

> <EXACT_MASS>
312.114174271

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.579925599963644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
3.017193087

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.900137390894255

> <JCHEM_PKA_STRONGEST_BASIC>
8.825952885735783

> <JCHEM_POLAR_SURFACE_AREA>
39.660000000000004

> <JCHEM_REFRACTIVITY>
92.06179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
NDMC

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060536
     RDKit          3D
Norclozapine
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.8299   -4.6769   -1.7571 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4078   -3.0101   -1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4230   -2.0725   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0787   -0.7606   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940   -0.3981   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918   -1.3534   -0.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014   -2.6761   -1.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121   -1.1577   -0.5477 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -0.1340   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039   -0.2149    0.1277 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799    0.5807   -0.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720    0.5599   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3742   -0.7790   -0.0182 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4351   -1.7473    0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1924   -1.1045    1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566    1.1382    0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5580    1.8449    1.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1332    3.0550    1.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1278    3.5610    1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299    2.8249    0.7453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    1.6302    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6749    1.0109   -0.5248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487   -2.3304   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8416    0.0078   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131   -3.4172   -1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047    0.0485   -1.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262    1.5882   -0.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8606    0.9870    0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    1.2093   -0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205   -1.1147   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1210   -2.4371   -0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8641   -2.4010    1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -1.9598    1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402   -0.6368    2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377    1.4394    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136    3.6242    2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4867    4.4916    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261    3.1681    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4081    1.6125   -0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
  7  2  1  0
 15 10  1  0
 21 16  1  0
 22  5  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 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
M  END

HEADER    PROTEIN                                 17-APR-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-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
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                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   13                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0060536
HETATM    1 CL1  UNL     1      -3.830  -4.677  -1.757  1.00  0.00          CL  
HETATM    2  C1  UNL     1      -3.408  -3.010  -1.383  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.423  -2.072  -1.381  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.079  -0.761  -1.085  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.794  -0.398  -0.804  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.792  -1.353  -0.811  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.101  -2.676  -1.104  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.412  -1.158  -0.548  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.201  -0.134  -0.015  1.00  0.00           C  
HETATM   10  N2  UNL     1       1.604  -0.215   0.128  1.00  0.00           N  
HETATM   11  C8  UNL     1       2.480   0.581  -0.686  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.872   0.560  -0.065  1.00  0.00           C  
HETATM   13  N3  UNL     1       4.374  -0.779  -0.018  1.00  0.00           N  
HETATM   14  C10 UNL     1       3.435  -1.747   0.455  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.192  -1.104   1.090  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.357   1.138   0.476  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.558   1.845   1.240  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.133   3.055   1.746  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.128   3.561   1.521  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.030   2.825   0.745  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.630   1.630   0.238  1.00  0.00           C  
HETATM   22  N4  UNL     1      -2.675   1.011  -0.525  1.00  0.00           N  
HETATM   23  H1  UNL     1      -5.449  -2.330  -1.600  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.842   0.008  -1.072  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.313  -3.417  -1.107  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.605   0.048  -1.674  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.126   1.588  -0.907  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.861   0.987   0.947  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.508   1.209  -0.699  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.820  -1.115  -0.882  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.121  -2.437  -0.354  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.864  -2.401   1.258  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.535  -1.960   1.348  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.540  -0.637   2.014  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.538   1.439   1.409  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.814   3.624   2.339  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.487   4.492   1.897  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.026   3.168   0.536  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.408   1.612  -0.909  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3    7
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6   22
CONECT    6    7    7    8
CONECT    7   25
CONECT    8    9    9
CONECT    9   10   16
CONECT   10   11   15
CONECT   11   12   26   27
CONECT   12   13   28   29
CONECT   13   14   30
CONECT   14   15   31   32
CONECT   15   33   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   21   22
CONECT   22   39
END

HMDB0060536
     RDKit          3D
Norclozapine
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.8299   -4.6769   -1.7571 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4078   -3.0101   -1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4230   -2.0725   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0787   -0.7606   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940   -0.3981   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918   -1.3534   -0.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014   -2.6761   -1.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121   -1.1577   -0.5477 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -0.1340   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039   -0.2149    0.1277 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799    0.5807   -0.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720    0.5599   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3742   -0.7790   -0.0182 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4351   -1.7473    0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1924   -1.1045    1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566    1.1382    0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5580    1.8449    1.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1332    3.0550    1.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1278    3.5610    1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299    2.8249    0.7453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    1.6302    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6749    1.0109   -0.5248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487   -2.3304   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8416    0.0078   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131   -3.4172   -1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047    0.0485   -1.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262    1.5882   -0.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8606    0.9870    0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    1.2093   -0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205   -1.1147   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1210   -2.4371   -0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8641   -2.4010    1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -1.9598    1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402   -0.6368    2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377    1.4394    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136    3.6242    2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4867    4.4916    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261    3.1681    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4081    1.6125   -0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
  7  2  1  0
 15 10  1  0
 21 16  1  0
 22  5  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 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
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Chloro-11-(1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepine	ChEBI
Demethylclozapine	ChEBI
Desmethylclozapine	ChEBI
N-Desmethyl clozapine	ChEBI
NDMC	ChEBI
8-Chloro-11-piperazin-1-yl-5H-dibenzo(b,e)(1,4)diazepine	MeSH
Norclozapine	ChEBI

Chemical Formula

C₁₇H₁₇ClN₄

Average Molecular Weight

312.797

Monoisotopic Molecular Weight

312.114174271

IUPAC Name

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

Traditional Name

NDMC

CAS Registry Number

Not Available

SMILES

ClC1=CC=C2NC3=CC=CC=C3C(=NC2=C1)N1CCNCC1

InChI Identifier

InChI=1S/C17H17ClN4/c18-12-5-6-15-16(11-12)21-17(22-9-7-19-8-10-22)13-3-1-2-4-14(13)20-15/h1-6,11,19-20H,7-10H2

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:64050 )
piperazines (CHEBI:64050 )
dibenzodiazepine (CHEBI:64050 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060536)

Organ

Kidney (HMDB: HMDB0060536)
Liver (HMDB: HMDB0060536)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060536)

Cellular substructure

Cytoplasm (HMDB: HMDB0060536)
Membrane (HMDB: HMDB0060536)

Source

Exogenous

Exogenous (HMDB: HMDB0060536)

Endogenous

Endogenous (HMDB: HMDB0060536)

Process

Not Available

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
Water Solubility	0.2 g/L	ALOGPS
logP	3.25	ALOGPS
logP	3.02	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.9	ChemAxon
pKa (Strongest Basic)	8.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.66 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	92.06 m³·mol⁻¹	ChemAxon
Polarizability	33.58 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+H]+	167.775	30932474
DeepCCS	[M-H]-	165.417	30932474
DeepCCS	[M-2H]-	198.87	30932474
DeepCCS	[M+Na]+	174.097	30932474
AllCCS	[M+H]+	171.4	32859911
AllCCS	[M+H-H2O]+	168.1	32859911
AllCCS	[M+NH4]+	174.5	32859911
AllCCS	[M+Na]+	175.4	32859911
AllCCS	[M-H]-	173.5	32859911
AllCCS	[M+Na-2H]-	172.8	32859911
AllCCS	[M+HCOO]-	172.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norclozapine	ClC1=CC=C2NC3=CC=CC=C3C(=NC2=C1)N1CCNCC1	4241.3	Standard polar	33892256
Norclozapine	ClC1=CC=C2NC3=CC=CC=C3C(=NC2=C1)N1CCNCC1	2955.4	Standard non polar	33892256
Norclozapine	ClC1=CC=C2NC3=CC=CC=C3C(=NC2=C1)N1CCNCC1	2975.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norclozapine,1TMS,isomer #1	C[Si](C)(C)N1C2=CC=C(Cl)C=C2N=C(N2CCNCC2)C2=CC=CC=C21	2810.0	Semi standard non polar	33892256
Norclozapine,1TMS,isomer #1	C[Si](C)(C)N1C2=CC=C(Cl)C=C2N=C(N2CCNCC2)C2=CC=CC=C21	2698.0	Standard non polar	33892256
Norclozapine,1TMS,isomer #1	C[Si](C)(C)N1C2=CC=C(Cl)C=C2N=C(N2CCNCC2)C2=CC=CC=C21	4157.1	Standard polar	33892256
Norclozapine,1TMS,isomer #2	C[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3NC3=CC=CC=C23)CC1	2999.6	Semi standard non polar	33892256
Norclozapine,1TMS,isomer #2	C[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3NC3=CC=CC=C23)CC1	3020.0	Standard non polar	33892256
Norclozapine,1TMS,isomer #2	C[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3NC3=CC=CC=C23)CC1	4594.7	Standard polar	33892256
Norclozapine,2TMS,isomer #1	C[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C)C3=CC=CC=C23)CC1	2943.3	Semi standard non polar	33892256
Norclozapine,2TMS,isomer #1	C[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C)C3=CC=CC=C23)CC1	2986.8	Standard non polar	33892256
Norclozapine,2TMS,isomer #1	C[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C)C3=CC=CC=C23)CC1	3965.4	Standard polar	33892256
Norclozapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC=C(Cl)C=C2N=C(N2CCNCC2)C2=CC=CC=C21	2956.9	Semi standard non polar	33892256
Norclozapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC=C(Cl)C=C2N=C(N2CCNCC2)C2=CC=CC=C21	2906.9	Standard non polar	33892256
Norclozapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC=C(Cl)C=C2N=C(N2CCNCC2)C2=CC=CC=C21	4212.6	Standard polar	33892256
Norclozapine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3NC3=CC=CC=C23)CC1	3224.2	Semi standard non polar	33892256
Norclozapine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3NC3=CC=CC=C23)CC1	3209.3	Standard non polar	33892256
Norclozapine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3NC3=CC=CC=C23)CC1	4813.4	Standard polar	33892256
Norclozapine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC1	3283.6	Semi standard non polar	33892256
Norclozapine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC1	3380.0	Standard non polar	33892256
Norclozapine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC1	4086.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norclozapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0016-9080000000-e5a1e856cf588ec3b2c6	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norclozapine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norclozapine 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 - Norclozapine 10V, Positive-QTOF	splash10-03di-0009000000-7cf412ccc6a185a32893	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 20V, Positive-QTOF	splash10-03di-0039000000-447fe506f0de08f3a236	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 40V, Positive-QTOF	splash10-0006-2290000000-c1c2dd97da1db1b554a6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 10V, Negative-QTOF	splash10-03di-0009000000-c0fb9c4f98b955f22ee4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 20V, Negative-QTOF	splash10-03di-0019000000-2a2da1946b96480241e4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 40V, Negative-QTOF	splash10-0006-9060000000-b9a39c856d2c8566d39b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 10V, Positive-QTOF	splash10-03di-0009000000-19ee5c40a0267a7c3d31	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 20V, Positive-QTOF	splash10-03di-0019000000-cb30f19e8d9094be09aa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 40V, Positive-QTOF	splash10-01r6-1091000000-16307b800b31dddedd25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 10V, Negative-QTOF	splash10-03di-0009000000-36527b79e8e0db55602b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 20V, Negative-QTOF	splash10-03di-1009000000-5ddb83e6baa29fcab0a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norclozapine 40V, Negative-QTOF	splash10-05ai-4192000000-fda9bbc6faa449b756b5	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desmethylclozapine

METLIN ID

Not Available

PubChem Compound

135409468

PDB ID

Not Available

ChEBI ID

64050

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

Ekstrom J, Godoy T, Riva A: N-Desmethylclozapine exerts dual and opposite effects on salivary secretion in the rat. Eur J Oral Sci. 2010 Feb;118(1):1-8. doi: 10.1111/j.1600-0722.2009.00696.x. [PubMed:20156258 ]
Couchman L, Morgan PE, Spencer EP, Flanagan RJ: Plasma clozapine, norclozapine, and the clozapine:norclozapine ratio in relation to prescribed dose and other factors: data from a therapeutic drug monitoring service, 1993-2007. Ther Drug Monit. 2010 Aug;32(4):438-47. doi: 10.1097/FTD.0b013e3181dad1fb. [PubMed:20463634 ]
Ertugrul A, Ozdemir H, Vural A, Dalkara T, Meltzer HY, Saka E: The influence of N-desmethylclozapine and clozapine on recognition memory and BDNF expression in hippocampus. Brain Res Bull. 2011 Feb 1;84(2):144-50. doi: 10.1016/j.brainresbull.2010.11.014. Epub 2010 Dec 4. [PubMed:21134422 ]
Godoy T, Riva A, Ekstrom J: Clozapine-induced salivation: interaction with N-desmethylclozapine and amisulpride in an experimental rat model. Eur J Oral Sci. 2011 Aug;119(4):275-81. doi: 10.1111/j.1600-0722.2011.00832.x. [PubMed:21726287 ]
Heusler P, Bruins Slot L, Tourette A, Tardif S, Cussac D: The clozapine metabolite N-desmethylclozapine displays variable activity in diverse functional assays at human dopamine D(2) and serotonin 5-HT(1)A receptors. Eur J Pharmacol. 2011 Nov 1;669(1-3):51-8. doi: 10.1016/j.ejphar.2011.07.031. Epub 2011 Aug 5. [PubMed:21835172 ]
Humbert-Claude M, Davenas E, Gbahou F, Vincent L, Arrang JM: Involvement of histamine receptors in the atypical antipsychotic profile of clozapine: a reassessment in vitro and in vivo. Psychopharmacology (Berl). 2012 Mar;220(1):225-41. doi: 10.1007/s00213-011-2471-5. Epub 2011 Sep 13. [PubMed:21912901 ]

Showing metabocard for Norclozapine (HMDB0060536)

MOL for HMDB0060536 (Norclozapine)

3D MOL for HMDB0060536 (Norclozapine)

3D SDF for HMDB0060536 (Norclozapine)

3D-SDF for HMDB0060536 (Norclozapine)

PDB for HMDB0060536 (Norclozapine)

3D PDB for HMDB0060536 (Norclozapine)

SMILES for HMDB0060536 (Norclozapine)

INCHI for HMDB0060536 (Norclozapine)

Structure for HMDB0060536 (Norclozapine)

3D Structure for HMDB0060536 (Norclozapine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra