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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015513

Secondary Accession Numbers

HMDB15513

Metabolite Identification

Common Name

Fludiazepam

Description

Fludiazepam, also known as erispan, 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. Fludiazepam is a drug which is used for the short-term treatment of anxiety disorders. Fludiazepam is a moderately basic compound (based on its pKa). It exerts its pharmacological properties via enhancement of GABAergic inhibition. Fludiazepam is a potentially toxic compound. It is marketed in Japan and Taiwan. Fludiazepam has been used recreationally. Fludiazepam, marketed under the brand name Erispan (エリスパン) is a potent benzodiazepine and 2ʹ-fluoro derivative of diazepam, originally developed by Hoffman-La Roche in the 1960s. Fludiazepam has 4 times more binding affinity for benzodiazepine receptors than diazepam. It possesses anxiolytic, anticonvulsant, sedative, hypnotic and skeletal muscle relaxant properties.

Structure

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

HMDB0015513
     RDKit          3D
Fludiazepam
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5292   -0.3494   -1.6179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393   -0.7334   -0.8029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -2.0954   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -2.8617   -1.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9503   -2.6871    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049   -1.9615    0.0842 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5257   -0.6822    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8662   -0.2036   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    1.0524   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937    1.3729   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6369    0.3961   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067   -0.9064   -0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8652   -1.2074    0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130   -2.5023    0.1304 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4989    0.3046    0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444    1.3193    1.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    2.3286    1.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3195    3.6056    2.5987 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2300    2.3501    1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922    1.3394    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8211    0.3287   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5168   -0.3780   -1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -1.0475   -2.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3202    0.6483   -2.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460   -2.6633    1.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -3.7317   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6414    1.8607   -0.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9409    2.4296   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.6799   -0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9695   -1.6722   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9552    1.2351    1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8839    3.1663    1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6779    1.2655   -0.1550 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
 13 14  1  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 13  8  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
M  END

1567
  Mrv0541 02231215342D          

 21 23  0  0  0  0            999 V2000
    2.8171   -2.3592    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8785   -1.4649    0.0000 F   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
    4.7694   -0.3478    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
    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
    4.6465   -1.1636    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
    5.2914   -1.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1823   -0.5607    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 15  1  0  0  0  0
  2 17  1  0  0  0  0
  3 11  2  0  0  0  0
  4  7  1  0  0  0  0
  4 11  1  0  0  0  0
  4 14  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 17  1  0  0  0  0
 10 18  2  0  0  0  0
 12 15  2  0  0  0  0
 13 16  2  0  0  0  0
 15 16  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015513

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F

> <INCHI_IDENTIFIER>
InChI=1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3

> <INCHI_KEY>
ROYOYTLGDLIGBX-UHFFFAOYSA-N

> <FORMULA>
C16H12ClFN2O

> <MOLECULAR_WEIGHT>
302.731

> <EXACT_MASS>
302.062218928

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.45257506451923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
3.218788503666667

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.8889263261678797

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
80.02830000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fludiazepam

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015513
     RDKit          3D
Fludiazepam
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5292   -0.3494   -1.6179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393   -0.7334   -0.8029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -2.0954   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -2.8617   -1.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9503   -2.6871    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049   -1.9615    0.0842 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5257   -0.6822    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8662   -0.2036   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    1.0524   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937    1.3729   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6369    0.3961   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067   -0.9064   -0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8652   -1.2074    0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130   -2.5023    0.1304 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4989    0.3046    0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444    1.3193    1.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    2.3286    1.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3195    3.6056    2.5987 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2300    2.3501    1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922    1.3394    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8211    0.3287   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5168   -0.3780   -1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -1.0475   -2.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3202    0.6483   -2.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460   -2.6633    1.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -3.7317   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6414    1.8607   -0.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9409    2.4296   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.6799   -0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9695   -1.6722   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9552    1.2351    1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8839    3.1663    1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6779    1.2655   -0.1550 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
 13 14  1  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 13  8  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1567                                              
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  F   UNK     0       7.240  -2.734   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0       4.873   4.404   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.581   1.812   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       8.042   1.812   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.311  -0.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.699   0.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   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       5.541   3.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.456  -1.955   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.585  -0.572   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   2.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.138  -2.869   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.692  -2.173   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      10.336  -0.087   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      11.540  -1.047   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.311  -2.569   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   17                                                            
CONECT    3   11                                                            
CONECT    4    7   11   14                                                  
CONECT    5    8    9                                                       
CONECT    6    7    8   12                                                  
CONECT    7    4    6   13                                                  
CONECT    8    5    6   10                                                  
CONECT    9    5   11                                                       
CONECT   10    8   17   18                                                  
CONECT   11    3    4    9                                                  
CONECT   12    6   15                                                       
CONECT   13    7   16                                                       
CONECT   14    4                                                            
CONECT   15    1   12   16                                                  
CONECT   16   13   15                                                       
CONECT   17    2   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    HMDB0015513
HETATM    1  C1  UNL     1      -3.529  -0.349  -1.618  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.439  -0.733  -0.803  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.993  -2.095  -0.719  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.545  -2.862  -1.520  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.950  -2.687   0.215  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.305  -1.962   0.084  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.526  -0.682   0.135  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.866  -0.204  -0.033  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.351   1.052  -0.153  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.694   1.373  -0.222  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.637   0.396  -0.173  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.207  -0.906  -0.054  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.865  -1.207   0.015  1.00  0.00           C  
HETATM   14  F1  UNL     1       2.513  -2.502   0.130  1.00  0.00           F  
HETATM   15  C11 UNL     1      -0.499   0.305   0.439  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.044   1.319   1.259  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.919   2.329   1.566  1.00  0.00           C  
HETATM   18 CL1  UNL     1      -0.320   3.606   2.599  1.00  0.00          CL  
HETATM   19  C14 UNL     1      -2.230   2.350   1.081  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.692   1.339   0.268  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.821   0.329  -0.041  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.517  -0.378  -1.111  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.603  -1.047  -2.472  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.320   0.648  -2.064  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.346  -2.663   1.250  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.812  -3.732  -0.084  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.641   1.861  -0.265  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.941   2.430  -0.315  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.671   0.680  -0.228  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.969  -1.672  -0.017  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.955   1.235   1.656  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.884   3.166   1.348  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.678   1.265  -0.155  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21
CONECT    3    4    4    5
CONECT    5    6   25   26
CONECT    6    7    7
CONECT    7    8   15
CONECT    8    9    9   13
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14
CONECT   15   16   16   21
CONECT   16   17   31
CONECT   17   18   19   19
CONECT   19   20   32
CONECT   20   21   21   33
END

HMDB0015513
     RDKit          3D
Fludiazepam
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5292   -0.3494   -1.6179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393   -0.7334   -0.8029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -2.0954   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -2.8617   -1.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9503   -2.6871    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049   -1.9615    0.0842 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5257   -0.6822    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8662   -0.2036   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510    1.0524   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937    1.3729   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6369    0.3961   -0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2067   -0.9064   -0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8652   -1.2074    0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130   -2.5023    0.1304 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4989    0.3046    0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444    1.3193    1.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    2.3286    1.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3195    3.6056    2.5987 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2300    2.3501    1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922    1.3394    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8211    0.3287   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5168   -0.3780   -1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032   -1.0475   -2.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3202    0.6483   -2.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3460   -2.6633    1.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -3.7317   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6414    1.8607   -0.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9409    2.4296   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.6799   -0.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9695   -1.6722   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9552    1.2351    1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8839    3.1663    1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6779    1.2655   -0.1550 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
 13 14  1  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 13  8  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Chloro-5-(O-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one	ChEBI
Erispan	ChEBI
Fludiazepan	HMDB
1-Methyl-5-(2-fluorophenyl)-7-chloro-1,3-dihydro-2H-(1,4)benzodiazepin-2-one	HMDB

Chemical Formula

C₁₆H₁₂ClFN₂O

Average Molecular Weight

302.731

Monoisotopic Molecular Weight

302.062218928

IUPAC Name

7-chloro-5-(2-fluorophenyl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Traditional Name

fludiazepam

CAS Registry Number

3900-31-0

SMILES

CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F

InChI Identifier

InChI=1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3

InChI Key

ROYOYTLGDLIGBX-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
Fluorobenzene
Halobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Ketimine
Lactam
Azacycle
Carboxylic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organooxygen compound
Imine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organohalogen compound
Organochloride
Organofluoride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:31618 )
organochlorine compound (CHEBI:31618 )
1,4-benzodiazepinone (CHEBI:31618 )

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: HMDB0015513)

Source

Exogenous

Exogenous (HMDB: HMDB0015513)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Anxiolytic drug (HMDB: HMDB0015513)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	295 - 297 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.014 g/L	Not Available
LogP	2.75	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	2.83	ALOGPS
logP	3.22	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	1.89	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	80.03 m³·mol⁻¹	ChemAxon
Polarizability	29.45 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]+	167.5	30932474
DeepCCS	[M-H]-	165.142	30932474
DeepCCS	[M-2H]-	198.096	30932474
DeepCCS	[M+Na]+	173.593	30932474
AllCCS	[M+H]+	165.9	32859911
AllCCS	[M+H-H2O]+	162.2	32859911
AllCCS	[M+NH4]+	169.3	32859911
AllCCS	[M+Na]+	170.3	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	166.3	32859911
AllCCS	[M+HCOO]-	165.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fludiazepam	CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F	3549.6	Standard polar	33892256
Fludiazepam	CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F	2351.2	Standard non polar	33892256
Fludiazepam	CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1F	2401.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fludiazepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-00rb-1290000000-db34d4ae17fe6cf3b0ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fludiazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0uk9-2794000000-6f1a3e2e0783b2069f2f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 10V, Positive-QTOF	splash10-0udi-0009000000-b2b78d93d910447bac75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 20V, Positive-QTOF	splash10-0udi-0009000000-a3a8b605f4519d7b3f3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 40V, Positive-QTOF	splash10-0006-3790000000-fdbf33d4f6fc63137032	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 10V, Negative-QTOF	splash10-0udi-0009000000-d02f66b89dd2bd046268	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 20V, Negative-QTOF	splash10-0udi-0019000000-192b14d7bf485cfa6ad1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 40V, Negative-QTOF	splash10-0fri-4090000000-384ca37be75332aae71e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 10V, Positive-QTOF	splash10-0udi-0009000000-c01193f4b7d1e5f3a22b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 20V, Positive-QTOF	splash10-0udi-0029000000-f4108b88eded0bee1211	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 40V, Positive-QTOF	splash10-052r-0691000000-5f13769812ae66b4fb7a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 10V, Negative-QTOF	splash10-0udi-0009000000-7a97a80624fe91a9d550	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 20V, Negative-QTOF	splash10-0udi-0019000000-e2f274918639146a9afe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fludiazepam 40V, Negative-QTOF	splash10-001j-0090000000-8fa0ab5ce849828b1d1d	2021-10-11	Wishart Lab	View Spectrum

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 DB01567	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01567	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

DB01567

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fludiazepam

METLIN ID

Not Available

PubChem Compound

3369

PDB ID

Not Available

ChEBI ID

31618

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

Nakatsuka I, Shimizu H, Asami Y, Katoh T, Hirose A, Yoshitake A: Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. Life Sci. 1985 Jan 14;36(2):113-9. [PubMed:2857046 ]
Ishiwata K, Yanai K, Ido T, Miura-Kanno Y, Kawashima K: Synthesis and biodistribution of [11C]fludiazepam for imaging benzodiazepine receptors. Int J Rad Appl Instrum B. 1988;15(4):365-71. [PubMed:2855634 ]

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 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

2. 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

3. 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

4. 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

5. 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

6. 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

7. 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

Enzyme Details

8. Gamma-aminobutyric acid receptor subunit beta-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:: GABRB3
Uniprot ID:: P28472
Molecular weight:: 54115.0

References

Enzyme Details

9. Gamma-aminobutyric acid receptor subunit delta

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:: GABRD
Uniprot ID:: O14764
Molecular weight:: 50707.8

References

Enzyme Details

10. Gamma-aminobutyric acid receptor subunit epsilon

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:: GABRE
Uniprot ID:: P78334
Molecular weight:: 57971.2

References

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Showing metabocard for Fludiazepam (HMDB0015513)

MOL for HMDB0015513 (Fludiazepam)

3D MOL for HMDB0015513 (Fludiazepam)

3D SDF for HMDB0015513 (Fludiazepam)

3D-SDF for HMDB0015513 (Fludiazepam)

PDB for HMDB0015513 (Fludiazepam)

3D PDB for HMDB0015513 (Fludiazepam)

SMILES for HMDB0015513 (Fludiazepam)

INCHI for HMDB0015513 (Fludiazepam)

Structure for HMDB0015513 (Fludiazepam)

3D Structure for HMDB0015513 (Fludiazepam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

References

References