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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014766

Secondary Accession Numbers

HMDB14766

Metabolite Identification

Common Name

Clorazepate

Description

Clorazepate is only found in individuals that have used or taken this drug. It is a water-soluble benzodiazepine derivative effective in the treatment of anxiety. It has also muscle relaxant and anticonvulsant actions. [PubChem]Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABA_A) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. 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.

Structure

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

HMDB0244826
     RDKit          3D
(3S)-7-Chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylic acid
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.7519   -3.8091   -0.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103   -2.8631    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8570   -3.1473    0.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0644   -1.4885    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6200   -1.4117    0.0313 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1441   -0.3583   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5503   -0.5624   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4966    0.3798   -0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183    0.0523   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2530   -1.2415   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -2.2034   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9722   -1.9021   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126    0.9975    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5851    1.7654    0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2690    3.0772    1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4516    4.0379    2.0633 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211    3.6620    0.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058    2.8663    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025    1.5498   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742    0.8201   -0.8718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7914   -0.5941   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -1.0863   -1.4527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4267   -2.6804    0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -1.1830    1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2071    1.4219   -0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660    0.8348   -0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2869   -1.5472   -0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6403   -3.2387   -0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -2.7006    0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    1.2778    1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1657    4.6961    0.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7649    3.2081   -0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1957    1.3709   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  4  1  0
 12  7  1  0
 19 13  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
M  END

628
  Mrv0541 02231214492D          

 22 24  0  0  1  0            999 V2000
    2.5467   -2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3403    2.0183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7038    2.0801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4164    2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1838    0.6300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375    0.6300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1106   -0.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8540   -0.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3674   -0.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5231    1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4989   -0.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981    1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1881   -1.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4818   -1.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -1.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2669   -0.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3760   -1.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8811    2.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9120   -0.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210   -2.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890   -1.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  2 12  2  0  0  0  0
  3 19  1  0  0  0  0
  4 19  2  0  0  0  0
  5  9  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 13  1  0  0  0  0
  8 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 12  1  0  0  0  0
 10 19  1  0  0  0  0
 11 17  2  0  0  0  0
 11 18  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014766

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1N=C(C2=CC=CC=C2)C2=C(NC1=O)C=CC(Cl)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H11ClN2O3/c17-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)19-14(16(21)22)15(20)18-12/h1-8,14H,(H,18,20)(H,21,22)

> <INCHI_KEY>
XDDJGVMJFWAHJX-UHFFFAOYSA-N

> <FORMULA>
C16H11ClN2O3

> <MOLECULAR_WEIGHT>
314.723

> <EXACT_MASS>
314.045819935

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.625736988123027

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylic acid

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
3.206338529999999

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.233953140202436

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3205174094454324

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6426618306823179

> <JCHEM_POLAR_SURFACE_AREA>
78.75999999999999

> <JCHEM_REFRACTIVITY>
82.67610000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clorazepate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244826
     RDKit          3D
(3S)-7-Chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylic acid
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.7519   -3.8091   -0.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103   -2.8631    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8570   -3.1473    0.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0644   -1.4885    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6200   -1.4117    0.0313 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1441   -0.3583   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5503   -0.5624   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4966    0.3798   -0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183    0.0523   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2530   -1.2415   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -2.2034   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9722   -1.9021   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126    0.9975    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5851    1.7654    0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2690    3.0772    1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4516    4.0379    2.0633 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211    3.6620    0.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058    2.8663    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025    1.5498   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742    0.8201   -0.8718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7914   -0.5941   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -1.0863   -1.4527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4267   -2.6804    0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -1.1830    1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2071    1.4219   -0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660    0.8348   -0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2869   -1.5472   -0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6403   -3.2387   -0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -2.7006    0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    1.2778    1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1657    4.6961    0.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7649    3.2081   -0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1957    1.3709   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  4  1  0
 12  7  1  0
 19 13  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 628                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.754  -5.040   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       4.369   3.767   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.780   3.883   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.377   5.040   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.076   1.176   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.537   1.176   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.806  -0.993   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.194  -0.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.419  -0.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.576   2.380   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.398  -1.285   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.036   2.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.951  -2.591   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -1.208   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.633  -3.505   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.188  -2.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.832  -0.723   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.169  -2.808   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.245   3.767   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.036  -1.683   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.373  -3.768   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.806  -3.206   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   12                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    9   12                                                       
CONECT    6    8   10                                                       
CONECT    7    8    9   13                                                  
CONECT    8    6    7   11                                                  
CONECT    9    5    7   14                                                  
CONECT   10    6   12   19                                                  
CONECT   11    8   17   18                                                  
CONECT   12    2    5   10                                                  
CONECT   13    7   15                                                       
CONECT   14    9   16                                                       
CONECT   15    1   13   16                                                  
CONECT   16   14   15                                                       
CONECT   17   11   20                                                       
CONECT   18   11   21                                                       
CONECT   19    3    4   10                                                  
CONECT   20   17   22                                                       
CONECT   21   18   22                                                       
CONECT   22   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0014766
HETATM    1  O1  UNL     1      -1.286  -1.670   1.714  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.031  -2.021   0.756  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.341  -2.441   1.046  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.599  -2.014  -0.662  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.214  -1.540  -0.663  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.266  -0.380  -0.343  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.698  -0.238  -0.466  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.442   0.901  -0.342  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.816   0.845  -0.393  1.00  0.00           C  
HETATM   10  C7  UNL     1       4.493  -0.340  -0.572  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.760  -1.503  -0.703  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.410  -1.443  -0.650  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.540   0.693   0.198  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.135   1.402   1.167  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.534   2.489   1.709  1.00  0.00           C  
HETATM   16 CL1  UNL     1       0.283   3.432   2.931  1.00  0.00          CL  
HETATM   17  C13 UNL     1      -1.804   2.870   1.332  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.450   2.124   0.357  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.820   1.054  -0.193  1.00  0.00           C  
HETATM   20  N2  UNL     1      -2.666   0.327  -1.114  1.00  0.00           N  
HETATM   21  C16 UNL     1      -2.505  -1.062  -1.389  1.00  0.00           C  
HETATM   22  O3  UNL     1      -3.188  -1.543  -2.334  1.00  0.00           O  
HETATM   23  H1  UNL     1      -3.656  -3.340   0.728  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.656  -3.021  -1.103  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.945   1.860  -0.265  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.420   1.755  -0.292  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.558  -0.404  -0.615  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.244  -2.472  -0.848  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.870  -2.392  -0.758  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.106   1.068   1.504  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.310   3.724   1.767  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.438   2.416   0.059  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.409   0.861  -1.564  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   23
CONECT    4    5   21   24
CONECT    5    6    6
CONECT    6    7   13
CONECT    7    8    8   12
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   29
CONECT   13   14   14   19
CONECT   14   15   30
CONECT   15   16   17   17
CONECT   17   18   31
CONECT   18   19   19   32
CONECT   19   20
CONECT   20   21   33
CONECT   21   22   22
END

HMDB0244826
     RDKit          3D
(3S)-7-Chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylic acid
 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.7519   -3.8091   -0.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103   -2.8631    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8570   -3.1473    0.1922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0644   -1.4885    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6200   -1.4117    0.0313 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1441   -0.3583   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5503   -0.5624   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4966    0.3798   -0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183    0.0523   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2530   -1.2415   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -2.2034   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9722   -1.9021   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126    0.9975    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5851    1.7654    0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2690    3.0772    1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4516    4.0379    2.0633 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211    3.6620    0.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058    2.8663    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025    1.5498   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742    0.8201   -0.8718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7914   -0.5941   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -1.0863   -1.4527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4267   -2.6804    0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -1.1830    1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2071    1.4219   -0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660    0.8348   -0.8536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2869   -1.5472   -0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6403   -3.2387   -0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -2.7006    0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    1.2778    1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1657    4.6961    0.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7649    3.2081   -0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1957    1.3709   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  4  1  0
 12  7  1  0
 19 13  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Chloro-2,3-dihydro-2,2-dihydroxy-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid	ChEBI
Clorazepate	ChEBI
7-Chloro-2,3-dihydro-2,2-dihydroxy-5-phenyl-1H-1,4-benzodiazepine-3-carboxylate	Generator
Chlorazepate	MeSH
Clorazepate dipotassium	MeSH
Clorazepate monopotassium	MeSH
Dipotassium chlorazepate	MeSH
Tranxene	MeSH
Tranxilium	MeSH
Clorazepic acid	Generator, KEGG
Dipotassium, clorazepate	MeSH, HMDB
Monopotassium, clorazepate	MeSH, HMDB
Chlorazepate, dipotassium	MeSH, HMDB

Chemical Formula

C₁₆H₁₁ClN₂O₃

Average Molecular Weight

314.723

Monoisotopic Molecular Weight

314.045819935

IUPAC Name

7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylic acid

Traditional Name

clorazepate

CAS Registry Number

23887-31-2

SMILES

OC(=O)C1N=C(C2=CC=CC=C2)C2=C(NC1=O)C=CC(Cl)=C2

InChI Identifier

InChI=1S/C16H11ClN2O3/c17-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)19-14(16(21)22)15(20)18-12/h1-8,14H,(H,18,20)(H,21,22)

InChI Key

XDDJGVMJFWAHJX-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
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
1,3-dicarbonyl compound
Carboxamide group
Ketimine
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Organic oxygen compound
Imine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1,4-benzodiazepinone (CHEBI:3761 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014766)
Membrane (HMDB: HMDB0014766)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

anticonvulsant (HMDB: HMDB0014766)

Pharmaceutical industry

prodrug (HMDB: HMDB0014766)
anxiolytic drug (HMDB: HMDB0014766)

GABA modulator (HMDB: HMDB0014766)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.025 g/L	Not Available
LogP	3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	2.68	ALOGPS
logP	3.21	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-0.64	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.68 m³·mol⁻¹	ChemAxon
Polarizability	30.63 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]+	167.487	30932474
DeepCCS	[M-H]-	165.129	30932474
DeepCCS	[M-2H]-	198.422	30932474
DeepCCS	[M+Na]+	173.649	30932474
AllCCS	[M+H]+	169.4	32859911
AllCCS	[M+H-H2O]+	165.9	32859911
AllCCS	[M+NH4]+	172.7	32859911
AllCCS	[M+Na]+	173.7	32859911
AllCCS	[M-H]-	168.9	32859911
AllCCS	[M+Na-2H]-	168.2	32859911
AllCCS	[M+HCOO]-	167.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clorazepate	OC(=O)C1N=C(C2=CC=CC=C2)C2=C(NC1=O)C=CC(Cl)=C2	4278.5	Standard polar	33892256
Clorazepate	OC(=O)C1N=C(C2=CC=CC=C2)C2=C(NC1=O)C=CC(Cl)=C2	2621.4	Standard non polar	33892256
Clorazepate	OC(=O)C1N=C(C2=CC=CC=C2)C2=C(NC1=O)C=CC(Cl)=C2	2840.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Clorazepate,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C2NC1=O	2747.3	Semi standard non polar	33892256
Clorazepate,1TMS,isomer #2	C[Si](C)(C)N1C(=O)C(C(=O)O)N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C21	2537.5	Semi standard non polar	33892256
Clorazepate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C2N([Si](C)(C)C)C1=O	2549.5	Semi standard non polar	33892256
Clorazepate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C2N([Si](C)(C)C)C1=O	2653.3	Standard non polar	33892256
Clorazepate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C2N([Si](C)(C)C)C1=O	3608.9	Standard polar	33892256
Clorazepate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C2NC1=O	2947.5	Semi standard non polar	33892256
Clorazepate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)C(C(=O)O)N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C21	2837.6	Semi standard non polar	33892256
Clorazepate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	2989.4	Semi standard non polar	33892256
Clorazepate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	3061.2	Standard non polar	33892256
Clorazepate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	3720.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clorazepate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2090000000-36dc0db4681a42cb62d1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clorazepate GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-9153000000-20955633c43ee4b5fcf3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clorazepate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clorazepate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clorazepate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clorazepate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clorazepate GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - Clorazepate 10V, Positive-QTOF	splash10-014i-0039000000-04f8ade5dbb98231f6d5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 20V, Positive-QTOF	splash10-014i-0194000000-77f2c863a9b5ed450724	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 40V, Positive-QTOF	splash10-0w4r-3390000000-08793ab9fa2d5c97ebe8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 10V, Negative-QTOF	splash10-03xr-0089000000-f7743c0f914c2fc65685	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 20V, Negative-QTOF	splash10-014i-1092000000-a7f9ddb60f21ad0d8c34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 40V, Negative-QTOF	splash10-0006-9010000000-4ba3a72ff61da2cab011	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 10V, Positive-QTOF	splash10-014i-0009000000-3b6dc9550f10c7fb899e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 20V, Positive-QTOF	splash10-00kb-0095000000-26882b3fd53c73fd3908	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 40V, Positive-QTOF	splash10-03di-0090000000-4b8c3ab746b6ade0d1f6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 10V, Negative-QTOF	splash10-03di-0009000000-4c893c51087ae5eb95c9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 20V, Negative-QTOF	splash10-014i-2090000000-16b08349edcd85152d86	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clorazepate 40V, Negative-QTOF	splash10-001l-9000000000-071a2b32b700b46350ad	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB00628	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00628	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

DB00628

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2707

KEGG Compound ID

C06921

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clorazepate

METLIN ID

Not Available

PubChem Compound

2809

PDB ID

Not Available

ChEBI ID

3761

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

Authors unspecified: Systematic review of the benzodiazepines. Guidelines for data sheets on diazepam, chlordiazepoxide, medazepam, clorazepate, lorazepam, oxazepam, temazepam, triazolam, nitrazepam, and flurazepam. Committee on the Review of Medicines. Br Med J. 1980 Mar 29;280(6218):910-2. [PubMed:7388368 ]
McElhatton PR: The effects of benzodiazepine use during pregnancy and lactation. Reprod Toxicol. 1994 Nov-Dec;8(6):461-75. [PubMed:7881198 ]

Only showing the first 10 proteins. There are 21 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. Translocator protein

General function:: Signal transduction mechanisms
Specific function:: Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme. Plays a role in the transport of cholesterol across mitochondrial membranes in steroidogenic cells
Gene Name:: TSPO
Uniprot ID:: P30536
Molecular weight:: 18778.7

References

Enzyme Details

4. 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

5. 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

6. 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

7. 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

8. 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

9. 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

10. 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

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

Showing metabocard for Clorazepate (HMDB0014766)

MOL for HMDB0014766 (Clorazepate)

3D MOL for HMDB0014766 (Clorazepate)

3D SDF for HMDB0014766 (Clorazepate)

3D-SDF for HMDB0014766 (Clorazepate)

PDB for HMDB0014766 (Clorazepate)

3D PDB for HMDB0014766 (Clorazepate)

SMILES for HMDB0014766 (Clorazepate)

INCHI for HMDB0014766 (Clorazepate)

Structure for HMDB0014766 (Clorazepate)

3D Structure for HMDB0014766 (Clorazepate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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