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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (21)transporters (1) Show 22 proteins XML

enzymes (21)transporters (1) Show 22 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015534

Secondary Accession Numbers

HMDB15534

Metabolite Identification

Common Name

Nitrazepam

Description

Nitrazepam is only found in individuals that have used or taken this drug. It is a benzodiazepine derivative used as an anticonvulsant and hypnotic.Nitrazepam belongs to a group of medicines called benzodiazepines. It acts on benzodiazepine receptors in the brain which are associated with the GABA receptors causing an enhanced binding of GABA (gamma amino butyric acid) to GABAA receptors. GABA is a major inhibitory neurotransmitter in the brain, involved in inducing sleepiness, muscular relaxation and control of anxiety and fits, and slows down the central nervous system. The anticonvulsant properties of nitrazepam and other benzodiazepines may be in part or entirely due to binding to voltage-dependent sodium channels rather than benzodiazepine receptors. Sustained repetitive firing seems to be limited by benzodiazepines effect of slowing recovery of sodium channels from inactivation.

Structure

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

HMDB0015534
     RDKit          3D
Nitrazepam
 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.6985   -4.2476    0.8545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744   -3.1139    0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6973   -3.0036   -0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923   -2.0666   -0.6474 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666   -0.8273   -0.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6416   -0.1993   -0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975    1.0044    0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1535    1.6010    0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2336    0.9662   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157   -0.2562   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7687   -0.8244   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8815   -0.1280    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7664    1.1885   -0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522    2.0029   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7793    3.3732   -0.4357 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.7498    3.8273   -0.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628    4.1700   -0.1960 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.0111    1.4736    0.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1407    0.1483    0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0484   -0.6508    0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2858   -2.0225    0.9322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -3.9702   -1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649   -2.6452   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    1.5481    1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3206    2.5641    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356    1.4250    0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8762   -0.7637   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924   -1.7839   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    1.5464   -0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621    2.1514    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425   -0.2518    1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152   -2.2352    1.6275 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
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  2  1  0
 11  6  1  0
 20 12  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 18 30  1  0
 19 31  1  0
 21 32  1  0
M  CHG  2  15   1  17  -1
M  END

1595
  Mrv1652305271900232D          

 21 23  0  0  0  0            999 V2000
    2.3403    2.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8668   -2.5929    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.2913   -2.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1839    1.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375    1.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5467   -2.1255    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.1107    0.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3674    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8540    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4990   -0.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1881   -0.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232    1.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4818   -1.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6982    1.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -0.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2670    0.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3760   -0.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9120   -0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890   -1.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  2  0  0  0  0
  2  6  1  0  0  0  0
  3  6  2  0  0  0  0
  4  8  1  0  0  0  0
  4 15  1  0  0  0  0
  5  9  2  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 17  2  0  0  0  0
 10 18  1  0  0  0  0
 11 14  2  0  0  0  0
 12 16  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  CHG  2   2  -1   6   1
M  END
> <DATABASE_ID>
HMDB0015534

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H11N3O3/c19-14-9-16-15(10-4-2-1-3-5-10)12-8-11(18(20)21)6-7-13(12)17-14/h1-8H,9H2,(H,17,19)

> <INCHI_KEY>
KJONHKAYOJNZEC-UHFFFAOYSA-N

> <FORMULA>
C15H11N3O3

> <MOLECULAR_WEIGHT>
281.2661

> <EXACT_MASS>
281.080041233

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.672964280229994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.5479600116666665

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.658611394121115

> <JCHEM_PKA_STRONGEST_BASIC>
2.6501462430155946

> <JCHEM_POLAR_SURFACE_AREA>
84.6

> <JCHEM_REFRACTIVITY>
78.21170000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gerson

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015534
     RDKit          3D
Nitrazepam
 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.6985   -4.2476    0.8545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744   -3.1139    0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6973   -3.0036   -0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923   -2.0666   -0.6474 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666   -0.8273   -0.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6416   -0.1993   -0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975    1.0044    0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1535    1.6010    0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2336    0.9662   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157   -0.2562   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7687   -0.8244   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8815   -0.1280    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7664    1.1885   -0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522    2.0029   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7793    3.3732   -0.4357 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.7498    3.8273   -0.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628    4.1700   -0.1960 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.0111    1.4736    0.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1407    0.1483    0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0484   -0.6508    0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2858   -2.0225    0.9322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -3.9702   -1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649   -2.6452   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    1.5481    1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3206    2.5641    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356    1.4250    0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8762   -0.7637   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924   -1.7839   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    1.5464   -0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621    2.1514    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425   -0.2518    1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152   -2.2352    1.6275 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
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  2  1  0
 11  6  1  0
 20 12  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 18 30  1  0
 19 31  1  0
 21 32  1  0
M  CHG  2  15   1  17  -1
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1595                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       4.369   4.840   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.485  -4.840   0.000  0.00  0.00           O-1
HETATM    3  O   UNK     0       6.144  -4.630   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.077   2.249   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.537   2.249   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.754  -3.968   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0       5.807   0.079   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.419   0.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.194   0.747   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.398  -0.213   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.951  -1.519   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -0.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.577   3.453   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.633  -2.432   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.037   3.453   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.188  -1.736   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.832   0.350   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.169  -1.736   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.036  -0.611   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.373  -2.696   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.806  -2.133   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    8   15                                                       
CONECT    5    9   13                                                       
CONECT    6    2    3   14                                                  
CONECT    7    8    9   11                                                  
CONECT    8    4    7   12                                                  
CONECT    9    5    7   10                                                  
CONECT   10    9   17   18                                                  
CONECT   11    7   14                                                       
CONECT   12    8   16                                                       
CONECT   13    5   15                                                       
CONECT   14    6   11   16                                                  
CONECT   15    1    4   13                                                  
CONECT   16   12   14                                                       
CONECT   17   10   19                                                       
CONECT   18   10   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   21                                                       
CONECT   21   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0015534
HETATM    1  O1  UNL     1      -1.699  -4.248   0.855  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.574  -3.114   0.319  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.697  -3.004  -0.909  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.392  -2.067  -0.647  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.367  -0.827  -0.197  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.642  -0.199  -0.052  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.898   1.004   0.521  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.154   1.601   0.556  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.234   0.966  -0.012  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.016  -0.256  -0.601  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.769  -0.824  -0.624  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.881  -0.128   0.049  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.766   1.188  -0.315  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.852   2.003  -0.087  1.00  0.00           C  
HETATM   15  N2  UNL     1      -1.779   3.373  -0.436  1.00  0.00           N1+
HETATM   16  O2  UNL     1      -0.750   3.827  -0.946  1.00  0.00           O  
HETATM   17  O3  UNL     1      -2.863   4.170  -0.196  1.00  0.00           O1-
HETATM   18  C13 UNL     1      -3.011   1.474   0.490  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.141   0.148   0.855  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.048  -0.651   0.622  1.00  0.00           C  
HETATM   21  N3  UNL     1      -2.286  -2.022   0.932  1.00  0.00           N  
HETATM   22  H1  UNL     1      -0.221  -3.970  -1.105  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.265  -2.645  -1.784  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.125   1.548   1.052  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.321   2.564   1.021  1.00  0.00           H  
HETATM   26  H5  UNL     1       5.236   1.425   0.006  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.876  -0.764  -1.053  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.592  -1.784  -1.085  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.134   1.546  -0.819  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.862   2.151   0.661  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.043  -0.252   1.302  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.015  -2.235   1.627  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4   22   23
CONECT    4    5    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   28
CONECT   12   13   13   20
CONECT   13   14   29
CONECT   14   15   18   18
CONECT   15   16   16   17
CONECT   18   19   30
CONECT   19   20   20   31
CONECT   20   21
CONECT   21   32
END

HMDB0015534
     RDKit          3D
Nitrazepam
 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.6985   -4.2476    0.8545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5744   -3.1139    0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6973   -3.0036   -0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923   -2.0666   -0.6474 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666   -0.8273   -0.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6416   -0.1993   -0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975    1.0044    0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1535    1.6010    0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2336    0.9662   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157   -0.2562   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7687   -0.8244   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8815   -0.1280    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7664    1.1885   -0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522    2.0029   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7793    3.3732   -0.4357 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.7498    3.8273   -0.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628    4.1700   -0.1960 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.0111    1.4736    0.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1407    0.1483    0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0484   -0.6508    0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2858   -2.0225    0.9322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -3.9702   -1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649   -2.6452   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    1.5481    1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3206    2.5641    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356    1.4250    0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8762   -0.7637   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924   -1.7839   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    1.5464   -0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621    2.1514    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425   -0.2518    1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152   -2.2352    1.6275 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
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  2  1  0
 11  6  1  0
 20 12  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 18 30  1  0
 19 31  1  0
 21 32  1  0
M  CHG  2  15   1  17  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one	ChEBI
2,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-one	ChEBI
7-Nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one	ChEBI
7-Nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one	ChEBI
Apodorm	ChEBI
Atempol	ChEBI
Benzalin	ChEBI
Calsmin	ChEBI
Dormicum	ChEBI
Eatan	ChEBI
Eunoctin	ChEBI
Gerson	ChEBI
Hipnax	ChEBI
Hipsal	ChEBI
Ibrovek	ChEBI
Imeson	ChEBI
Imesont	ChEBI
Mogadon	ChEBI
N-Desmethylnimetazepam	ChEBI
Nelbon	ChEBI
Nelmat	ChEBI
Neozepam	ChEBI
Neuchlonic	ChEBI
Nitrados	ChEBI
Nitrazepamum	ChEBI
Paxisyn	ChEBI
Pelson	ChEBI
Persopit	ChEBI
Radedorm	ChEBI
Relact	ChEBI
Remnos	ChEBI
Ro 4-5360	ChEBI
Ro 5-3059	ChEBI
Somitran	ChEBI
Sonebon	ChEBI
Sonnolin	ChEBI
Surem	ChEBI
Trazenin	ChEBI
Unisomnia	ChEBI
1, 3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one	HMDB
2,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-ON	HMDB
7-Nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one	HMDB
Alter brand OF nitrazepam	HMDB
CSP Brand OF nitrazepam	HMDB
DDSA brand OF nitrazepam	HMDB
Desitin brand OF nitrazepam	HMDB
Nitrazepam al	HMDB
Nitrazepam-neuraxpharm	HMDB
Nitrodiazepam	HMDB
Novanox	HMDB
Taurus brand OF nitrazepam	HMDB
CT-Arzneimittel brand OF nitrazepam	HMDB
Aliud brand OF nitrazepam	HMDB
Alphapharma brand OF nitrazepam	HMDB
Dormicum brand OF nitrazepam	HMDB
Nitrazadon	HMDB
Nitrazep	HMDB
Norgine brand OF nitrazepam	HMDB
Rhoxalpharma brand OF nitrazepam	HMDB
Scheurich brand OF nitrazepam	HMDB
Serenade	HMDB
Dermatech brand OF nitrazepam	HMDB
ICN brand OF nitrazepam	HMDB
Imadorm	HMDB
Pfleger brand OF nitrazepam	HMDB
Rhoxal-nitrazepam	HMDB
Wernigerode brand OF nitrazepam	HMDB
Allphar brand OF nitrazepam	HMDB
Alodorm	HMDB
Alpharma brand OF nitrazepam	HMDB
Dormalon	HMDB
Dormo-puren	HMDB
Protea brand OF nitrazepam	HMDB
Somnite	HMDB
United drug brand OF nitrazepam	HMDB
Neuraxpharm brand OF nitrazepam	HMDB
Rhoxal nitrazepam	HMDB
Nitrazepam neuraxpharm	HMDB

Chemical Formula

C₁₅H₁₁N₃O₃

Average Molecular Weight

281.2661

Monoisotopic Molecular Weight

281.080041233

IUPAC Name

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

Traditional Name

gerson

CAS Registry Number

146-22-5

SMILES

[O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C15H11N3O3/c19-14-9-16-15(10-4-2-1-3-5-10)12-8-11(18(20)21)6-7-13(12)17-14/h1-8H,9H2,(H,17,19)

InChI Key

KJONHKAYOJNZEC-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
Alpha-amino acid or derivatives
Nitroaromatic compound
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Ketimine
Lactam
C-nitro compound
Organic nitro compound
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Imine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic zwitterion
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-nitro compound (CHEBI:7581 )
1,4-benzodiazepinone (CHEBI:7581 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015534)

Source

Exogenous

Exogenous (HMDB: HMDB0015534)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0015534)
Sedative (HMDB: HMDB0015534)

Pharmaceutical industry

Antispasmodic drug (HMDB: HMDB0015534)

Biological role

Modulator

GABA modulator (HMDB: HMDB0015534)

Drug metabolite (HMDB: HMDB0015534)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	225 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.03 g/L	Not Available
LogP	2.25	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	163.6	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	1.95	ALOGPS
logP	2.55	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.66	ChemAxon
pKa (Strongest Basic)	2.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.21 m³·mol⁻¹	ChemAxon
Polarizability	27.67 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
DarkChem	[M+H]+	166.927	31661259
DarkChem	[M-H]-	165.532	31661259
DeepCCS	[M+H]+	161.113	30932474
DeepCCS	[M-H]-	158.755	30932474
DeepCCS	[M-2H]-	192.585	30932474
DeepCCS	[M+Na]+	167.812	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.5	32859911
AllCCS	[M-H]-	164.6	32859911
AllCCS	[M+Na-2H]-	163.7	32859911
AllCCS	[M+HCOO]-	162.9	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.	4.22 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1193 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.17 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1771.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	329.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	101.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	404.8 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	583.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1077.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	404.2 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	1198.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	312.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	228.4 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	56.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nitrazepam	[O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2)C=C1	4023.7	Standard polar	33892256
Nitrazepam	[O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2)C=C1	2788.8	Standard non polar	33892256
Nitrazepam	[O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2)C=C1	2803.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nitrazepam,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC([N+](=O)[O-])=CC=C21	2549.5	Semi standard non polar	33892256
Nitrazepam,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC([N+](=O)[O-])=CC=C21	2621.7	Standard non polar	33892256
Nitrazepam,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC([N+](=O)[O-])=CC=C21	3693.9	Standard polar	33892256
Nitrazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC([N+](=O)[O-])=CC=C21	2822.0	Semi standard non polar	33892256
Nitrazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC([N+](=O)[O-])=CC=C21	2822.3	Standard non polar	33892256
Nitrazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=CC=C2)C2=CC([N+](=O)[O-])=CC=C21	3749.7	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01595	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01595	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

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

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01595

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4350

KEGG Compound ID

C07487

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nitrazepam

METLIN ID

Not Available

PubChem Compound

4506

PDB ID

Not Available

ChEBI ID

7581

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

Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [PubMed:2570451 ]
Podhorna J, Krsiak M: Behavioural effects of a benzodiazepine receptor partial agonist, Ro 19-8022, in the social conflict test in mice. Behav Pharmacol. 2000 Apr;11(2):143-51. [PubMed:10877119 ]
Rickels K: The clinical use of hypnotics: indications for use and the need for a variety of hypnotics. Acta Psychiatr Scand Suppl. 1986;332:132-41. [PubMed:2883820 ]
Robertson MD, Drummer OH: Postmortem drug metabolism by bacteria. J Forensic Sci. 1995 May;40(3):382-6. [PubMed:7782744 ]
Nowakowska E, Chodera A: Studies on the involvement of opioid mechanism in the locomotor effects of benzodiazepines in rats. Pharmacol Biochem Behav. 1991 Feb;38(2):265-6. [PubMed:1676167 ]

Only showing the first 10 proteins. There are 22 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Enzyme Details

2. Gamma-aminobutyric acid receptor subunit gamma-2

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRG2
Uniprot ID:: P18507
Molecular weight:: 54161.8

References

Enzyme Details

3. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

References

Enzyme Details

4. Gamma-aminobutyric acid receptor subunit alpha-2

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA2
Uniprot ID:: P47869
Molecular weight:: 51325.9

References

Enzyme Details

5. Gamma-aminobutyric acid receptor subunit alpha-3

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA3
Uniprot ID:: P34903
Molecular weight:: 55164.1

References

Enzyme Details

6. Gamma-aminobutyric acid receptor subunit alpha-4

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA4
Uniprot ID:: P48169
Molecular weight:: 61622.6

References

Enzyme Details

7. Gamma-aminobutyric acid receptor subunit alpha-5

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA5
Uniprot ID:: P31644
Molecular weight:: 52145.6

References

Enzyme Details

8. Gamma-aminobutyric acid receptor subunit alpha-6

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA6
Uniprot ID:: Q16445
Molecular weight:: 51023.7

References

Enzyme Details

9. Gamma-aminobutyric acid receptor subunit beta-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRB1
Uniprot ID:: P18505
Molecular weight:: 54234.1

References

Enzyme Details

10. Gamma-aminobutyric acid receptor subunit beta-2

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRB2
Uniprot ID:: P47870
Molecular weight:: 59149.9

References

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Only showing the first 10 proteins. There are 22 proteins in total.

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Showing metabocard for Nitrazepam (HMDB0015534)

MOL for HMDB0015534 (Nitrazepam)

3D MOL for HMDB0015534 (Nitrazepam)

3D SDF for HMDB0015534 (Nitrazepam)

3D-SDF for HMDB0015534 (Nitrazepam)

PDB for HMDB0015534 (Nitrazepam)

3D PDB for HMDB0015534 (Nitrazepam)

SMILES for HMDB0015534 (Nitrazepam)

INCHI for HMDB0015534 (Nitrazepam)

Structure for HMDB0015534 (Nitrazepam)

3D Structure for HMDB0015534 (Nitrazepam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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Transporters

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