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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014967

Secondary Accession Numbers

HMDB14967

Metabolite Identification

Common Name

Diazepam

Description

Diazepam is a benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of gamma-aminobutyric acid activity. It is used in the treatment of severe anxiety disorders, as a hypnotic in the short-term management of insomnia, as a sedative and premedicant, as an anticonvulsant, and in the management of alcohol withdrawal syndrome. (From Martindale, The Extra Pharmacopoeia, 30th ed, p589).

Structure

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

HMDB0014967
     RDKit          3D
Diazepam
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5873   -0.7394    1.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678   -0.8553    0.5336 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553   -2.1487    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924   -3.1433    0.5763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0471   -2.4576   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -1.7984   -0.7532 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5207   -0.5721   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8946   -0.2498   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587   -1.2191   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1961   -1.0431   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6275    0.1065    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7181    1.0515    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723    0.8532    0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5072    0.4723   -0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166    1.6825   -0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    2.7586   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2402    4.3003   -1.2888 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1439    2.6530   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6297    1.4407    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901    0.3462    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -0.4660    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7999   -1.7194    1.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4106   -0.0442    2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -3.5466   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3912   -2.1791   -2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5199   -2.1261   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9472   -1.7858   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7021    0.2159    0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0607    1.9667    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.6541    0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9949    1.7136   -1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7898    3.5406   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6281    1.3384    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  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
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20  2  1  0
 13  8  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
M  END

829
  Mrv0541 02231215022D          

 20 22  0  0  0  0            999 V2000
    2.8172   -2.3592    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6107    2.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542    0.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3080    0.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3811   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936    1.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686    1.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7694   -0.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586   -1.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7523   -1.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9781   -1.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5374   -0.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -1.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1824   -0.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2915   -1.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0594   -1.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2  9  2  0  0  0  0
  3  6  1  0  0  0  0
  3  9  1  0  0  0  0
  3 13  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
 10 16  2  0  0  0  0
 10 17  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  2  0  0  0  0
 14 15  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014967

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3

> <INCHI_KEY>
AAOVKJBEBIDNHE-UHFFFAOYSA-N

> <FORMULA>
C16H13ClN2O

> <MOLECULAR_WEIGHT>
284.74

> <EXACT_MASS>
284.071640755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.386528122049114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.0760865673333337

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.921450447162867

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
79.81190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diazepam

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014967
     RDKit          3D
Diazepam
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5873   -0.7394    1.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678   -0.8553    0.5336 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553   -2.1487    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924   -3.1433    0.5763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0471   -2.4576   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -1.7984   -0.7532 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5207   -0.5721   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8946   -0.2498   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587   -1.2191   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1961   -1.0431   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6275    0.1065    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7181    1.0515    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723    0.8532    0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5072    0.4723   -0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166    1.6825   -0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    2.7586   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2402    4.3003   -1.2888 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1439    2.6530   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6297    1.4407    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901    0.3462    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -0.4660    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7999   -1.7194    1.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4106   -0.0442    2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -3.5466   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3912   -2.1791   -2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5199   -2.1261   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9472   -1.7858   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7021    0.2159    0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0607    1.9667    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.6541    0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9949    1.7136   -1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7898    3.5406   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6281    1.3384    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  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
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20  2  1  0
 13  8  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 829                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       5.259  -4.404   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       4.873   4.404   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.581   1.812   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.042   1.812   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.311  -0.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   0.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.699   0.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   3.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.541   3.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.903  -0.649   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.456  -1.955   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.585  -0.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   2.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.138  -2.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.692  -2.173   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.336  -0.087   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.673  -2.172   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.540  -1.047   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.877  -3.132   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.311  -2.569   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2    9                                                            
CONECT    3    6    9   13                                                  
CONECT    4    7    8                                                       
CONECT    5    6    7   11                                                  
CONECT    6    3    5   12                                                  
CONECT    7    4    5   10                                                  
CONECT    8    4    9                                                       
CONECT    9    2    3    8                                                  
CONECT   10    7   16   17                                                  
CONECT   11    5   14                                                       
CONECT   12    6   15                                                       
CONECT   13    3                                                            
CONECT   14    1   11   15                                                  
CONECT   15   12   14                                                       
CONECT   16   10   18                                                       
CONECT   17   10   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   20                                                       
CONECT   20   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0014967
HETATM    1  C1  UNL     1      -3.587  -0.739   1.400  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.468  -0.855   0.534  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.055  -2.149   0.047  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.592  -3.143   0.576  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.047  -2.458  -1.033  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.216  -1.798  -0.753  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.521  -0.572  -0.411  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.895  -0.250  -0.199  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.859  -1.219  -0.529  1.00  0.00           C  
HETATM   10  C7  UNL     1       4.196  -1.043  -0.244  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.627   0.107   0.382  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.718   1.051   0.710  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.372   0.853   0.414  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.507   0.472  -0.343  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.017   1.682  -0.793  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.845   2.759  -0.733  1.00  0.00           C  
HETATM   17 CL1  UNL     1      -0.240   4.300  -1.289  1.00  0.00          CL  
HETATM   18  C14 UNL     1      -2.144   2.653  -0.239  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.630   1.441   0.204  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.790   0.346   0.143  1.00  0.00           C  
HETATM   21  H1  UNL     1      -4.535  -0.466   0.863  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.800  -1.719   1.859  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.411  -0.044   2.260  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.858  -3.547  -1.019  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.391  -2.179  -2.030  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.520  -2.126  -1.023  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.947  -1.786  -0.496  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.702   0.216   0.593  1.00  0.00           H  
HETATM   29  H9  UNL     1       4.061   1.967   1.208  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.706   1.654   0.782  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.995   1.714  -1.229  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.790   3.541  -0.201  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.628   1.338   0.591  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   20
CONECT    3    4    4    5
CONECT    5    6   24   25
CONECT    6    7    7
CONECT    7    8   14
CONECT    8    9    9   13
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   30
CONECT   14   15   15   20
CONECT   15   16   31
CONECT   16   17   18   18
CONECT   18   19   32
CONECT   19   20   20   33
END

HMDB0014967
     RDKit          3D
Diazepam
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5873   -0.7394    1.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678   -0.8553    0.5336 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553   -2.1487    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924   -3.1433    0.5763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0471   -2.4576   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -1.7984   -0.7532 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5207   -0.5721   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8946   -0.2498   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587   -1.2191   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1961   -1.0431   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6275    0.1065    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7181    1.0515    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723    0.8532    0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5072    0.4723   -0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166    1.6825   -0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    2.7586   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2402    4.3003   -1.2888 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1439    2.6530   -0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6297    1.4407    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901    0.3462    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -0.4660    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7999   -1.7194    1.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4106   -0.0442    2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -3.5466   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3912   -2.1791   -2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5199   -2.1261   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9472   -1.7858   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7021    0.2159    0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0607    1.9667    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.6541    0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9949    1.7136   -1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7898    3.5406   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6281    1.3384    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  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
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20  2  1  0
 13  8  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one	ChEBI
Methyl diazepinone	ChEBI
Valium	ChEBI
Diastat	Kegg
Methyldiazepinone	HMDB
Apaurin	MeSH, HMDB
Faustan	MeSH, HMDB
Relanium	MeSH, HMDB
Seduxen	MeSH, HMDB
Diazemuls	MeSH, HMDB
Sibazon	MeSH, HMDB
Stesolid	MeSH, HMDB

Chemical Formula

C₁₆H₁₃ClN₂O

Average Molecular Weight

284.74

Monoisotopic Molecular Weight

284.071640755

IUPAC Name

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

Traditional Name

diazepam

CAS Registry Number

439-14-5

SMILES

CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3

InChI Key

AAOVKJBEBIDNHE-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
Tertiary carboxylic acid amide
Carboxamide group
Ketimine
Lactam
Carboxylic acid derivative
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Imine
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:49575 )
1,4-benzodiazepinone (CHEBI:49575 )

Ontology

Physiological effect

Health effect

Observation

Nervous system disorder

Coma (HMDB: HMDB0014967)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0014967)
Rectal (HMDB: HMDB0014967)

Parenteral

Intramuscular (HMDB: HMDB0014967)

Source

Exogenous

Exogenous (HMDB: HMDB0014967)

Food

Food (HMDB: HMDB0014967)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Cereal and cereal product

Cereal

Common wheat (FooDB: FOOD00187)

Environmental

Wastewater (HMDB: HMDB0014967)

Endogenous

Plant

Plant (HMDB: HMDB0014967)
Poaceae (HMDB: HMDB0014967)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0014967)
Anxiolytic drug (HMDB: HMDB0014967)

Manufacturing industry

Material processing agent

GABA modulator (HMDB: HMDB0014967)

Environmental role

Environmental contaminant (HMDB: HMDB0014967)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	125 - 126 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.012 g/L	Not Available
LogP	2.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	164.2	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	2.63	ALOGPS
logP	3.08	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	2.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.81 m³·mol⁻¹	ChemAxon
Polarizability	29.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	166.831	30932474
DeepCCS	[M-H]-	164.473	30932474
DeepCCS	[M-2H]-	197.359	30932474
DeepCCS	[M+Na]+	172.924	30932474
AllCCS	[M+H]+	162.7	32859911
AllCCS	[M+H-H2O]+	158.9	32859911
AllCCS	[M+NH4]+	166.2	32859911
AllCCS	[M+Na]+	167.3	32859911
AllCCS	[M-H]-	166.0	32859911
AllCCS	[M+Na-2H]-	165.4	32859911
AllCCS	[M+HCOO]-	164.9	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.	6.09 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9927 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.04 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2134.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	411.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	177.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	228.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	539.4 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	590.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	68.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1318.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	462.3 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	1428.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	326.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	143.2 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	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diazepam	CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1	3713.2	Standard polar	33892256
Diazepam	CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1	2408.4	Standard non polar	33892256
Diazepam	CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1	2449.3	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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 DB00829	21059682	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00829	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

DB00829

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007103

KNApSAcK ID

Not Available

Chemspider ID

2908

KEGG Compound ID

C06948

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diazepam

METLIN ID

Not Available

PubChem Compound

3016

PDB ID

DZP

ChEBI ID

49575

Food Biomarker Ontology

Not Available

VMH ID

C06948

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Mant A, Whicker SD, McManus P, Birkett DJ, Edmonds D, Dumbrell D: Benzodiazepine utilisation in Australia: report from a new pharmacoepidemiological database. Aust J Public Health. 1993 Dec;17(4):345-9. [PubMed:7911332 ]
McLean MJ, Macdonald RL: Benzodiazepines, but not beta carbolines, limit high frequency repetitive firing of action potentials of spinal cord neurons in cell culture. J Pharmacol Exp Ther. 1988 Feb;244(2):789-95. [PubMed:2450203 ]
Earley JV, Fryer RI, Ning RY: Quinazolines and 1,4-benzodiazepines. LXXXIX: Haptens useful in benzodiazepine immunoassay development. J Pharm Sci. 1979 Jul;68(7):845-50. [PubMed:458601 ]
Oishi R, Nishibori M, Itoh Y, Saeki K: Diazepam-induced decrease in histamine turnover in mouse brain. Eur J Pharmacol. 1986 May 27;124(3):337-42. [PubMed:3089825 ]
Usami N, Yamamoto T, Shintani S, Ishikura S, Higaki Y, Katagiri Y, Hara A: Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5. [PubMed:11995921 ]

Showing metabocard for Diazepam (HMDB0014967)

MOL for HMDB0014967 (Diazepam)

3D MOL for HMDB0014967 (Diazepam)

3D SDF for HMDB0014967 (Diazepam)

3D-SDF for HMDB0014967 (Diazepam)

PDB for HMDB0014967 (Diazepam)

3D PDB for HMDB0014967 (Diazepam)

SMILES for HMDB0014967 (Diazepam)

INCHI for HMDB0014967 (Diazepam)

Structure for HMDB0014967 (Diazepam)

3D Structure for HMDB0014967 (Diazepam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized