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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:10:10 UTC

Update Date

2019-07-23 07:15:29 UTC

HMDB ID

HMDB0060970

Secondary Accession Numbers

HMDB60970

Metabolite Identification

Common Name

norclobazam

Description

norclobazam, also known as demethylclobazam, belongs to the class of organic compounds known as benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms). norclobazam is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060970
     RDKit          3D
norclobazam
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.5445   -2.6223    0.6880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3103   -1.8996    0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -2.5231   -0.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7851   -1.8600    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7914   -2.7502    0.5407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417   -0.5961    0.3446 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    0.5604    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9916    1.7053   -0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466    2.8944   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    2.8892   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    4.4134   -0.7346 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    1.7426   -0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515    0.5661   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490   -0.5047    0.0975 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4469   -0.2538    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589   -0.3662   -0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6152   -0.1315   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352    0.2334    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    0.3488    1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736    0.1099    1.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6420   -2.5059   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417   -3.5810    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271   -3.5269   -0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0655    1.7200    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9027    3.8184   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.7209   -0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7790   -0.6492   -1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2551   -0.2165   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3075    0.4165    0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9530    0.6350    2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    0.2127    2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  2  1  0
 20 15  1  0
 13  7  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END


  Mrv0541 07091309102D          

 20 22  0  0  0  0            999 V2000
    3.0808   -2.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8691   -2.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760   -1.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -1.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596   -0.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    1.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479   -0.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    0.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431    0.2691    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    2.0210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    0.1673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502    2.4825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502   -0.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
 10  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 12  1  0  0  0  0
 17 14  2  0  0  0  0
 18 11  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060970

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NC2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H11ClN2O2/c16-10-6-7-12-13(8-10)18(11-4-2-1-3-5-11)15(20)9-14(19)17-12/h1-8H,9H2,(H,17,19)

> <INCHI_KEY>
RRTVVRIFVKKTJK-UHFFFAOYSA-N

> <FORMULA>
C15H11ClN2O2

> <MOLECULAR_WEIGHT>
286.713

> <EXACT_MASS>
286.050905313

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.194057065497482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-chloro-4-hydroxy-1-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
3.417766575

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.151236937753027

> <JCHEM_PKA_STRONGEST_BASIC>
0.043055339708272355

> <JCHEM_POLAR_SURFACE_AREA>
52.9

> <JCHEM_REFRACTIVITY>
77.93780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-chloro-4-hydroxy-1-phenyl-3H-1,5-benzodiazepin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060970
     RDKit          3D
norclobazam
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.5445   -2.6223    0.6880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3103   -1.8996    0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -2.5231   -0.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7851   -1.8600    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7914   -2.7502    0.5407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417   -0.5961    0.3446 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    0.5604    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9916    1.7053   -0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466    2.8944   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    2.8892   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    4.4134   -0.7346 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    1.7426   -0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515    0.5661   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490   -0.5047    0.0975 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4469   -0.2538    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589   -0.3662   -0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6152   -0.1315   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352    0.2334    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    0.3488    1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736    0.1099    1.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6420   -2.5059   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417   -3.5810    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271   -3.5269   -0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0655    1.7200    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9027    3.8184   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.7209   -0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7790   -0.6492   -1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2551   -0.2165   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3075    0.4165    0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9530    0.6350    2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    0.2127    2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  2  1  0
 20 15  1  0
 13  7  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       5.751  -4.192   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.222  -3.738   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.622  -3.144   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.565  -2.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.965  -1.643   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.907   2.812   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.241   3.582   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.241   0.502   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.948   2.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.907   1.272   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.436  -1.189   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.575   2.812   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.575   1.272   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.280   3.430   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.280   0.655   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       1.574   0.502   0.000  0.00  0.00          Cl+0
HETATM   17  N   UNK     0       6.779   3.773   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       6.779   0.312   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       9.240   4.634   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.240  -0.549   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6    7   10                                                       
CONECT    7    6   12                                                       
CONECT    8   10   13                                                       
CONECT    9   14   15                                                       
CONECT   10    6    8   16                                                  
CONECT   11    4    5   18                                                  
CONECT   12    7   13   17                                                  
CONECT   13    8   12   18                                                  
CONECT   14    9   17   19                                                  
CONECT   15    9   18   20                                                  
CONECT   16   10                                                            
CONECT   17   12   14                                                       
CONECT   18   11   13   15                                                  
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0060970
HETATM    1  O1  UNL     1       0.544  -2.622   0.688  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.310  -1.900   0.164  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.562  -2.523  -0.321  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.785  -1.860   0.188  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.791  -2.750   0.541  1.00  0.00           O  
HETATM    6  N1  UNL     1      -3.042  -0.596   0.345  1.00  0.00           N  
HETATM    7  C4  UNL     1      -2.246   0.560   0.084  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.992   1.705  -0.059  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.347   2.894  -0.312  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.957   2.889  -0.414  1.00  0.00           C  
HETATM   11 CL1  UNL     1      -0.164   4.413  -0.735  1.00  0.00          CL  
HETATM   12  C8  UNL     1      -0.202   1.743  -0.271  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.851   0.566  -0.020  1.00  0.00           C  
HETATM   14  N2  UNL     1       0.049  -0.505   0.097  1.00  0.00           N  
HETATM   15  C10 UNL     1       1.447  -0.254   0.157  1.00  0.00           C  
HETATM   16  C11 UNL     1       2.259  -0.366  -0.969  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.615  -0.132  -0.935  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.235   0.233   0.250  1.00  0.00           C  
HETATM   19  C14 UNL     1       3.449   0.349   1.372  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.074   0.110   1.331  1.00  0.00           C  
HETATM   21  H1  UNL     1      -1.642  -2.506  -1.426  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.542  -3.581   0.004  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.927  -3.527  -0.116  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.065   1.720   0.019  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.903   3.818  -0.433  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.870   1.721  -0.350  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.779  -0.649  -1.883  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.255  -0.217  -1.807  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.308   0.417   0.267  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.953   0.635   2.298  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.491   0.213   2.245  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   14
CONECT    3    4   21   22
CONECT    4    5    6    6
CONECT    5   23
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   12
CONECT   12   13   13   26
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   20
CONECT   16   17   27
CONECT   17   18   18   28
CONECT   18   19   29
CONECT   19   20   20   30
CONECT   20   31
END

HMDB0060970
     RDKit          3D
norclobazam
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.5445   -2.6223    0.6880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3103   -1.8996    0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -2.5231   -0.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7851   -1.8600    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7914   -2.7502    0.5407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417   -0.5961    0.3446 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    0.5604    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9916    1.7053   -0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466    2.8944   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    2.8892   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    4.4134   -0.7346 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    1.7426   -0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515    0.5661   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490   -0.5047    0.0975 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4469   -0.2538    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589   -0.3662   -0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6152   -0.1315   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352    0.2334    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    0.3488    1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736    0.1099    1.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6420   -2.5059   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417   -3.5810    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271   -3.5269   -0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0655    1.7200    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9027    3.8184   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.7209   -0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7790   -0.6492   -1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2551   -0.2165   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3075    0.4165    0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9530    0.6350    2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    0.2127    2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  2  1  0
 20 15  1  0
 13  7  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Desmethylclobazam	HMDB
Demethylclobazam	HMDB

Chemical Formula

C₁₅H₁₁ClN₂O₂

Average Molecular Weight

286.713

Monoisotopic Molecular Weight

286.050905313

IUPAC Name

8-chloro-4-hydroxy-1-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one

Traditional Name

8-chloro-4-hydroxy-1-phenyl-3H-1,5-benzodiazepin-2-one

CAS Registry Number

22316-55-8

SMILES

OC1=NC2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)C1

InChI Identifier

InChI=1S/C15H11ClN2O2/c16-10-6-7-12-13(8-10)18(11-4-2-1-3-5-11)15(20)9-14(19)17-12/h1-8H,9H2,(H,17,19)

InChI Key

RRTVVRIFVKKTJK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

Not Available

Direct Parent

Benzodiazepines

Alternative Parents

Substituents

Benzodiazepine
Para-diazepine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
1,3-dicarbonyl compound
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060970)

Organ

Kidney (HMDB: HMDB0060970)
Liver (HMDB: HMDB0060970)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060970)

Cellular substructure

Cytoplasm (HMDB: HMDB0060970)
Membrane (HMDB: HMDB0060970)

Source

Endogenous

Endogenous (HMDB: HMDB0060970)

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	0.078 g/L	ALOGPS
logP	1.95	ALOGPS
logP	3.42	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	5.15	ChemAxon
pKa (Strongest Basic)	0.043	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.94 m³·mol⁻¹	ChemAxon
Polarizability	28.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	162.726	30932474
DeepCCS	[M-H]-	160.368	30932474
DeepCCS	[M-2H]-	193.497	30932474
DeepCCS	[M+Na]+	168.82	30932474
AllCCS	[M+H]+	162.3	32859911
AllCCS	[M+H-H2O]+	158.8	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.5	32859911
AllCCS	[M-H]-	161.3	32859911
AllCCS	[M+Na-2H]-	160.5	32859911
AllCCS	[M+HCOO]-	159.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.87 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8426 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2336.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	413.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	231.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	544.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	616.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1229.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	477.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1378.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	347.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	379.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	340.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	193.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	16.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
norclobazam	OC1=NC2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)C1	3847.2	Standard polar	33892256
norclobazam	OC1=NC2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)C1	2738.9	Standard non polar	33892256
norclobazam	OC1=NC2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)C1	2476.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
norclobazam,1TMS,isomer #1	C[Si](C)(C)OC1=NC2=CC=C(Cl)C=C2N(C2=CC=CC=C2)C(=O)C1	2438.2	Semi standard non polar	33892256
norclobazam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=CC=C(Cl)C=C2N(C2=CC=CC=C2)C(=O)C1	2614.0	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 - norclobazam GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-1190000000-9a24557fa76e55aad36d	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - norclobazam GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9227000000-f3d3d5d86326a63631c0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - norclobazam 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 - norclobazam 10V, Positive-QTOF	splash10-000i-0090000000-6b98366739669a1f252d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 20V, Positive-QTOF	splash10-000i-1090000000-c9799d5bf17fdc53fd0c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 40V, Positive-QTOF	splash10-0udl-9480000000-61f5fc03781db67942ff	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 10V, Negative-QTOF	splash10-000i-0090000000-13fef1b1228f9606e509	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 20V, Negative-QTOF	splash10-000i-0090000000-db0562d32d45b2f36518	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 40V, Negative-QTOF	splash10-000x-9510000000-46777da1b89160217ee1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 10V, Negative-QTOF	splash10-000i-0090000000-ba99e644d5930e82ef06	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 20V, Negative-QTOF	splash10-000i-0090000000-ba99e644d5930e82ef06	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 40V, Negative-QTOF	splash10-014u-0090000000-7b521dc2c599c9108a0d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 10V, Positive-QTOF	splash10-000i-0090000000-741114b1038b061132fd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 20V, Positive-QTOF	splash10-000i-0090000000-b3fc6c7cae9994a1e1c1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - norclobazam 40V, Positive-QTOF	splash10-014l-1290000000-42be6f70ad919c63fdff	2021-09-24	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

Not Available

METLIN ID

Not Available

PubChem Compound

89657

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

Not Available

Showing metabocard for norclobazam (HMDB0060970)

MOL for HMDB0060970 (norclobazam)

3D MOL for HMDB0060970 (norclobazam)

3D SDF for HMDB0060970 (norclobazam)

3D-SDF for HMDB0060970 (norclobazam)

PDB for HMDB0060970 (norclobazam)

3D PDB for HMDB0060970 (norclobazam)

SMILES for HMDB0060970 (norclobazam)

INCHI for HMDB0060970 (norclobazam)

Structure for HMDB0060970 (norclobazam)

3D Structure for HMDB0060970 (norclobazam)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra