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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:32:41 UTC

Update Date

2019-07-23 07:14:33 UTC

HMDB ID

HMDB0060538

Secondary Accession Numbers

HMDB0061094
HMDB60538
HMDB61094

Metabolite Identification

Common Name

Nordiazepam

Description

Nordiazepam, also known as desmethyldiazepam or dealkylprazepam, belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. Nordiazepam is a moderately basic compound (based on its pKa). Outside of the human body, Nordiazepam has been detected, but not quantified in, a few different foods, such as common wheats, corns, and potato. This could make nordiazepam a potential biomarker for the consumption of these foods. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell. Nordiazepam is a potentially toxic compound. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained.

Structure

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

HMDB0060538
     RDKit          3D
Nordiazepam
 30 32  0  0  0  0  0  0  0  0999 V2000
   -2.6498   -3.6565    0.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1898   -2.4956    0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1291   -2.2941    1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0693   -1.6848    1.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -0.6208    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5213   -0.2454   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035    0.7201   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1135    1.0878   -1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1913    0.4800   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180   -0.5193    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6342   -0.8683    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112    0.2517    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    1.5890    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5164    2.5540   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0457    4.2587   -0.2605 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8073    2.1521   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1910    0.8138   -0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -0.0980   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237   -1.4448   -0.2007 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214   -3.2308    2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232   -1.5982    2.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0381    1.2302   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139    1.8754   -1.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775    0.7986   -0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7544   -1.0157    0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174   -1.6512    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    1.8690    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    2.9286   -0.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1865    0.4832   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483   -1.6687   -0.7713 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 11  6  1  0
 18 12  1  0
  3 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

  Mrv0541 02241221402D          

 19 21  0  0  0  0            999 V2000
   -1.5519   -1.6408    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -1.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    0.1111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552    0.5725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988   -0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -1.5591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365   -1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529   -2.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -3.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741   -3.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6858   -4.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810   -3.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -2.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
  2 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060538

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)

> <INCHI_KEY>
AKPLHCDWDRPJGD-UHFFFAOYSA-N

> <FORMULA>
C15H11ClN2O

> <MOLECULAR_WEIGHT>
270.714

> <EXACT_MASS>
270.055990691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.408062774131473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.2120204986666656

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.299820888817013

> <JCHEM_PKA_STRONGEST_BASIC>
2.8480504744474846

> <JCHEM_POLAR_SURFACE_AREA>
41.46

> <JCHEM_REFRACTIVITY>
76.69600000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nordiazepam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060538
     RDKit          3D
Nordiazepam
 30 32  0  0  0  0  0  0  0  0999 V2000
   -2.6498   -3.6565    0.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1898   -2.4956    0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1291   -2.2941    1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0693   -1.6848    1.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -0.6208    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5213   -0.2454   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035    0.7201   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1135    1.0878   -1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1913    0.4800   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180   -0.5193    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6342   -0.8683    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112    0.2517    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    1.5890    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5164    2.5540   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0457    4.2587   -0.2605 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8073    2.1521   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1910    0.8138   -0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -0.0980   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237   -1.4448   -0.2007 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214   -3.2308    2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232   -1.5982    2.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0381    1.2302   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139    1.8754   -1.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775    0.7986   -0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7544   -1.0157    0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174   -1.6512    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    1.8690    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    2.9286   -0.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1865    0.4832   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483   -1.6687   -0.7713 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 11  6  1  0
 18 12  1  0
  3 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0      -2.897  -3.063   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0      -1.563  -2.293   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.230  -3.063   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.104  -2.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.104  -0.753   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.308   0.207   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.809  -0.135   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.770   1.069   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.478  -1.523   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.809  -2.910   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.308  -3.253   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.965  -4.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.094  -5.802   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.752  -7.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.280  -7.757   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.151  -6.710   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.494  -5.208   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.230   0.017   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.563  -0.753   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    5   19                                                       
CONECT   19   18    2                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0060538
HETATM    1  O1  UNL     1      -2.650  -3.656   0.466  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.190  -2.496   0.629  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.129  -2.294   1.666  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.069  -1.685   1.105  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.201  -0.621   0.358  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.521  -0.245  -0.069  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.804   0.720  -0.963  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.113   1.088  -1.260  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.191   0.480  -0.656  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.918  -0.519   0.266  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.634  -0.868   0.549  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.911   0.252   0.045  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.589   1.589   0.049  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.516   2.554  -0.268  1.00  0.00           C  
HETATM   15 CL1  UNL     1      -1.046   4.259  -0.261  1.00  0.00          CL  
HETATM   16  C13 UNL     1      -2.807   2.152  -0.595  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.191   0.814  -0.609  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.202  -0.098  -0.279  1.00  0.00           C  
HETATM   19  N2  UNL     1      -2.724  -1.445  -0.201  1.00  0.00           N  
HETATM   20  H1  UNL     1      -0.821  -3.231   2.148  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.523  -1.598   2.425  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.038   1.230  -1.562  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.314   1.875  -1.988  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.178   0.799  -0.919  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.754  -1.016   0.757  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.417  -1.651   1.271  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.397   1.869   0.370  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.516   2.929  -0.841  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.187   0.483  -0.860  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.548  -1.669  -0.771  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   20   21
CONECT    4    5    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   26
CONECT   12   13   13   18
CONECT   13   14   27
CONECT   14   15   16   16
CONECT   16   17   28
CONECT   17   18   18   29
CONECT   18   19
CONECT   19   30
END

HMDB0060538
     RDKit          3D
Nordiazepam
 30 32  0  0  0  0  0  0  0  0999 V2000
   -2.6498   -3.6565    0.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1898   -2.4956    0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1291   -2.2941    1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0693   -1.6848    1.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -0.6208    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5213   -0.2454   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035    0.7201   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1135    1.0878   -1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1913    0.4800   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180   -0.5193    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6342   -0.8683    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112    0.2517    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    1.5890    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5164    2.5540   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0457    4.2587   -0.2605 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8073    2.1521   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1910    0.8138   -0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -0.0980   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237   -1.4448   -0.2007 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214   -3.2308    2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232   -1.5982    2.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0381    1.2302   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139    1.8754   -1.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775    0.7986   -0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7544   -1.0157    0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174   -1.6512    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    1.8690    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    2.9286   -0.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1865    0.4832   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483   -1.6687   -0.7713 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 11  6  1  0
 18 12  1  0
  3 20  1  0
  3 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Demethyldiazepam	ChEBI
7-Chloro-1,3-dihydro-5-phenyl-(2H)-1,4-benzodiazepin-2-one	ChEBI
7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one	ChEBI
7-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one	ChEBI
Chlordesmethyldiazepam	ChEBI
Dealkylprazepam	ChEBI
Desmethyldiazepam	ChEBI
N-Demethyldiazepam	ChEBI
N-Deoxydemoxepam	ChEBI
N-Desmethyldiazepam	ChEBI
N1-Desmethyldiazepam	ChEBI
Nordazepamum	ChEBI
Norprazepam	ChEBI
Calmday	Kegg
Nordiazepam	ChEBI
N-Descyclopropylmethylprazepam	MeSH
Tranxilium N	MeSH
Vegesan	MeSH
N Descyclopropylmethyl prazepam	MeSH
N Desalkylhalazepam	MeSH
N Destrifluoroethylhalazepam	MeSH
N Descyclopropylmethylprazepam	MeSH
Nordaz	MeSH
Nordazepam	MeSH
Demethyldiazepam	MeSH
N-Descyclopropylmethyl-prazepam	MeSH
N-Destrifluoroethylhalazepam	MeSH
Deoxydemoxepam	MeSH
N-Desalkylhalazepam	MeSH

Chemical Formula

C₁₅H₁₁ClN₂O

Average Molecular Weight

270.714

Monoisotopic Molecular Weight

270.055990691

IUPAC Name

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

Traditional Name

nordiazepam

CAS Registry Number

1088-11-5

SMILES

ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1

InChI Identifier

InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)

InChI Key

AKPLHCDWDRPJGD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Cyclic carboximidic acid
Ketimine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Imine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:111762 )
1,4-benzodiazepinone (CHEBI:111762 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060538)

Cellular substructure

Organ

Liver (HMDB: HMDB0060538)
Kidney (HMDB: HMDB0060538)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060538)

Source

Exogenous

Exogenous (HMDB: HMDB0060538)

Food

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Common wheat (FooDB: FOOD00187)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Endogenous

Endogenous (HMDB: HMDB0060538)

Process

Not Available

Role

Biological role

Human metabolite (HMDB: HMDB0060538)
Anxiolytic (HMDB: HMDB0060538)

Modulator

GABA modulator (HMDB: HMDB0060538)
GABA modulator (HMDB: HMDB0060538)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Pharmaceutical industry

Anxiolytic drug (HMDB: HMDB0060538)

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	0.022 g/L	ALOGPS
logP	2.79	ALOGPS
logP	3.21	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.3	ChemAxon
pKa (Strongest Basic)	2.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.7 m³·mol⁻¹	ChemAxon
Polarizability	27.41 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]+	164.019	30932474
DeepCCS	[M-H]-	161.661	30932474
DeepCCS	[M-2H]-	194.547	30932474
DeepCCS	[M+Na]+	170.112	30932474
AllCCS	[M+H]+	159.2	32859911
AllCCS	[M+H-H2O]+	155.2	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.9	32859911
AllCCS	[M-H]-	160.5	32859911
AllCCS	[M+Na-2H]-	159.9	32859911
AllCCS	[M+HCOO]-	159.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nordiazepam	ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1	3764.0	Standard polar	33892256
Nordiazepam	ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1	2459.6	Standard non polar	33892256
Nordiazepam	ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1	2504.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nordiazepam,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C21	2280.9	Semi standard non polar	33892256
Nordiazepam,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C21	2436.7	Standard non polar	33892256
Nordiazepam,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C21	3350.8	Standard polar	33892256
Nordiazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C21	2559.9	Semi standard non polar	33892256
Nordiazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C21	2647.4	Standard non polar	33892256
Nordiazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C21	3426.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nordiazepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-06tf-0190000000-29b106f0dfb9b4601898	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nordiazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006x-1290000000-16289dee622e983dadb4	2014-10-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOF	splash10-014i-0090000000-08ab493d917dff556803	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOF	splash10-0006-0090000000-b3902adae33dd2ada996	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOF	splash10-0006-0090000000-e1f36555cb45aafb3578	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOF	splash10-0006-0090000000-4599707b6c514e2fd140	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOF	splash10-0006-0090000000-2afa9f8bad136457e913	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOF	splash10-052f-0090000000-39292916fbbd987c9c79	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOF	splash10-0udi-0490000000-93d06070b3ddb4f2bb1d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOF	splash10-0udi-0900000000-319db7de66dd214c6036	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QTOF , positive-QTOF	splash10-00di-0090000000-f12d8a37190a6a1a6260	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QTOF , positive-QTOF	splash10-00dl-0590000000-6667f22f2eaaa4d7d444	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QTOF , positive-QTOF	splash10-05mo-0950000000-9f91849bf0ea300eddf6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QTOF , positive-QTOF	splash10-052f-0940000000-113f94a665f60922a3cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOF	splash10-00di-0090000000-a17b063554f54d5ae790	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOF	splash10-00di-0090000000-00d132ae0ea246d26e2a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOF	splash10-00di-0390000000-02873020d1329d3d5c38	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOF	splash10-0006-1960000000-010c3ba06f80d4ace994	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOF	splash10-052f-1930000000-327cc931b60592065b64	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOF	splash10-0006-2910000000-0a0897ca546d1bc1cb27	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOF	splash10-0f6x-4900000000-7cc6b852b0d715a021c2	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordiazepam 10V, Positive-QTOF	splash10-00di-0090000000-42b4ac66c7efbf805ab7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordiazepam 20V, Positive-QTOF	splash10-00di-0090000000-eade00da0853b4fc330e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordiazepam 40V, Positive-QTOF	splash10-0k96-9760000000-acfef25bde706bde8e9d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordiazepam 10V, Negative-QTOF	splash10-014i-0090000000-1ed0d3938bd2d416daef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordiazepam 20V, Negative-QTOF	splash10-014i-0090000000-63aef3ca2706dc88c39f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordiazepam 40V, Negative-QTOF	splash10-0006-9220000000-e0ad5d0ad9c04e3b5ca9	2016-08-03	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

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007124

KNApSAcK ID

Not Available

Chemspider ID

2890

KEGG Compound ID

C07486

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desmethyldiazepam

METLIN ID

Not Available

PubChem Compound

2997

PDB ID

Not Available

ChEBI ID

111762

Food Biomarker Ontology

Not Available

VMH ID

C07486

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 Nordiazepam (HMDB0060538)

MOL for HMDB0060538 (Nordiazepam)

3D MOL for HMDB0060538 (Nordiazepam)

3D SDF for HMDB0060538 (Nordiazepam)

3D-SDF for HMDB0060538 (Nordiazepam)

PDB for HMDB0060538 (Nordiazepam)

3D PDB for HMDB0060538 (Nordiazepam)

SMILES for HMDB0060538 (Nordiazepam)

INCHI for HMDB0060538 (Nordiazepam)

Structure for HMDB0060538 (Nordiazepam)

3D Structure for HMDB0060538 (Nordiazepam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra