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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (17) Show 17 proteins XML

enzymes (17) Show 17 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015527

Secondary Accession Numbers

HMDB15527

Metabolite Identification

Common Name

Prazepam

Description

Prazepam, also known as demetrin or centrax, 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. Prazepam is a drug which is used for the treatment of anxiety disorders. Prazepam is a strong basic compound (based on its pKa). Prazepam is a potentially toxic compound. Abrupt or over-rapid discontinuation of prazepam after long-term use, even at low dosage, may result in a protracted withdrawal syndrome. Side effects of prazepam are less profound than with other benzodiazepines. Benzodiazepines require special precaution if used in the elderly, during pregnancy, in children, alcohol or drug-dependent individuals and individuals with comorbid psychiatric disorders. Animal studies have found prazepam taken during pregnancy results in delayed growth and causes reproductive abnormalities.

Structure

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

HMDB0015527
     RDKit          3D
Prazepam
 40 43  0  0  0  0  0  0  0  0999 V2000
    2.7844    0.6619   -2.2817 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7448    0.1091   -1.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563    0.1757   -2.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865    0.4254   -2.0581 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745   -0.0648   -0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432    0.3574   -0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2522    1.1885   -1.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4206    1.7515   -0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8592    1.5159    0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1079    0.7121    1.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9073    0.1461    0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5124   -1.1498   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3788   -2.0861    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725   -3.1365    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021   -4.2994    1.6851 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4860   -3.2775    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3837   -2.3533    0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -1.3230   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9019   -0.5075   -0.5704 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883   -0.2949    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395    0.8649    1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7919    2.2737    0.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1191    1.8471    1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4677   -0.8126   -3.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349    0.9291   -3.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9043    1.3704   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0073    2.3872   -1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7841    1.9505    0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4480    0.5208    2.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3385   -0.4258    1.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488   -1.9809    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8936   -4.0902    1.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4309   -2.4121    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -1.1300    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8096    0.1322   -0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4866    0.6011    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1345    2.9332    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296    2.5160   -0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9602    1.7292    0.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4567    2.2452    2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 19  2  1  0
 23 21  1  0
 11  6  1  0
 18 12  1  0
  3 24  1  0
  3 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 23 40  1  0
M  END

1588
  Mrv0541 02231215342D          

 23 26  0  0  0  0            999 V2000
    3.6651   -2.5532    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4586    2.1652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3022    0.7769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1560    0.7769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2548    1.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4859   -0.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291   -0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416    1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7684   -0.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9724   -0.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3066   -1.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260   -1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6174   -0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6003   -1.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4945   -1.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0304   -0.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1395   -1.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9074   -1.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 10  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4 12  1  0  0  0  0
  4 14  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  9 11  2  0  0  0  0
  9 13  1  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 11 15  1  0  0  0  0
 13 16  2  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015527

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC2=C(C=C1)N(CC1CC1)C(=O)CN=C2C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H17ClN2O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)21-11-18(23)22(17)12-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2

> <INCHI_KEY>
MWQCHHACWWAQLJ-UHFFFAOYSA-N

> <FORMULA>
C19H17ClN2O

> <MOLECULAR_WEIGHT>
324.804

> <EXACT_MASS>
324.102940883

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.76703104782766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
3.856663840666667

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.064137855264895

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
91.7539

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prazepam

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015527
     RDKit          3D
Prazepam
 40 43  0  0  0  0  0  0  0  0999 V2000
    2.7844    0.6619   -2.2817 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7448    0.1091   -1.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563    0.1757   -2.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865    0.4254   -2.0581 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745   -0.0648   -0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432    0.3574   -0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2522    1.1885   -1.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4206    1.7515   -0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8592    1.5159    0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1079    0.7121    1.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9073    0.1461    0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5124   -1.1498   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3788   -2.0861    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725   -3.1365    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021   -4.2994    1.6851 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4860   -3.2775    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3837   -2.3533    0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -1.3230   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9019   -0.5075   -0.5704 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883   -0.2949    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395    0.8649    1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7919    2.2737    0.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1191    1.8471    1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4677   -0.8126   -3.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349    0.9291   -3.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9043    1.3704   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0073    2.3872   -1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7841    1.9505    0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4480    0.5208    2.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3385   -0.4258    1.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488   -1.9809    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8936   -4.0902    1.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4309   -2.4121    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -1.1300    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8096    0.1322   -0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4866    0.6011    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1345    2.9332    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296    2.5160   -0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9602    1.7292    0.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4567    2.2452    2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 19  2  1  0
 23 21  1  0
 11  6  1  0
 18 12  1  0
  3 24  1  0
  3 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 23 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1588                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       6.842  -4.766   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       6.456   4.042   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       6.164   1.450   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.625   1.450   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.209   3.264   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.552   4.766   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080   4.312   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.663   1.793   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.507  -0.051   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.124   2.654   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.894  -0.719   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.664   2.654   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.168  -0.934   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.282  -0.051   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.039  -2.317   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.275  -2.535   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.486  -1.011   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.721  -3.231   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.919  -0.449   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.256  -2.534   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.123  -1.409   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.460  -3.494   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.894  -2.932   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   10                                                            
CONECT    3    8    9   10                                                  
CONECT    4   12   14                                                       
CONECT    5    6    7    8                                                  
CONECT    6    5    7                                                       
CONECT    7    5    6                                                       
CONECT    8    3    5                                                       
CONECT    9    3   11   13                                                  
CONECT   10    2    3   12                                                  
CONECT   11    9   14   15                                                  
CONECT   12    4   10                                                       
CONECT   13    9   16                                                       
CONECT   14    4   11   17                                                  
CONECT   15   11   18                                                       
CONECT   16   13   18                                                       
CONECT   17   14   19   20                                                  
CONECT   18    1   15   16                                                  
CONECT   19   17   21                                                       
CONECT   20   17   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   23                                                       
CONECT   23   21   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0015527
HETATM    1  O1  UNL     1       2.784   0.662  -2.282  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.745   0.109  -1.871  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.556   0.176  -2.767  1.00  0.00           C  
HETATM    4  N1  UNL     1      -0.687   0.425  -2.058  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.175  -0.065  -0.955  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.443   0.357  -0.451  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.252   1.189  -1.242  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.421   1.752  -0.803  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.859   1.516   0.470  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.108   0.712   1.290  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.907   0.146   0.812  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.512  -1.150  -0.241  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.379  -2.086   0.288  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.873  -3.136   1.021  1.00  0.00           C  
HETATM   15 CL1  UNL     1      -2.002  -4.299   1.685  1.00  0.00          CL  
HETATM   16  C13 UNL     1       0.486  -3.278   1.238  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.384  -2.353   0.712  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.858  -1.323  -0.010  1.00  0.00           C  
HETATM   19  N2  UNL     1       1.902  -0.507  -0.570  1.00  0.00           N  
HETATM   20  C16 UNL     1       3.088  -0.295   0.168  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.039   0.865   1.132  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.792   2.274   0.708  1.00  0.00           C  
HETATM   23  C19 UNL     1       4.119   1.847   1.217  1.00  0.00           C  
HETATM   24  H1  UNL     1       0.468  -0.813  -3.255  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.735   0.929  -3.549  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.904   1.370  -2.241  1.00  0.00           H  
HETATM   27  H4  UNL     1      -5.007   2.387  -1.459  1.00  0.00           H  
HETATM   28  H5  UNL     1      -5.784   1.950   0.842  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.448   0.521   2.299  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.338  -0.426   1.548  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.449  -1.981   0.053  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.894  -4.090   1.809  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.431  -2.412   0.848  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.690  -1.130   0.500  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.810   0.132  -0.646  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.487   0.601   2.087  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.135   2.933   1.317  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.730   2.516  -0.362  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.960   1.729   0.508  1.00  0.00           H  
HETATM   40  H17 UNL     1       4.457   2.245   2.208  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   24   25
CONECT    4    5    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   28
CONECT   10   11   11   29
CONECT   11   30
CONECT   12   13   13   18
CONECT   13   14   31
CONECT   14   15   16   16
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   18   19
CONECT   19   20
CONECT   20   21   34   35
CONECT   21   22   23   36
CONECT   22   23   37   38
CONECT   23   39   40
END

HMDB0015527
     RDKit          3D
Prazepam
 40 43  0  0  0  0  0  0  0  0999 V2000
    2.7844    0.6619   -2.2817 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7448    0.1091   -1.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563    0.1757   -2.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865    0.4254   -2.0581 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745   -0.0648   -0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432    0.3574   -0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2522    1.1885   -1.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4206    1.7515   -0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8592    1.5159    0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1079    0.7121    1.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9073    0.1461    0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5124   -1.1498   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3788   -2.0861    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725   -3.1365    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021   -4.2994    1.6851 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4860   -3.2775    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3837   -2.3533    0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -1.3230   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9019   -0.5075   -0.5704 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883   -0.2949    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395    0.8649    1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7919    2.2737    0.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1191    1.8471    1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4677   -0.8126   -3.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349    0.9291   -3.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9043    1.3704   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0073    2.3872   -1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7841    1.9505    0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4480    0.5208    2.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3385   -0.4258    1.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488   -1.9809    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8936   -4.0902    1.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4309   -2.4121    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -1.1300    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8096    0.1322   -0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4866    0.6011    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1345    2.9332    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296    2.5160   -0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9602    1.7292    0.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4567    2.2452    2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 19  2  1  0
 23 21  1  0
 11  6  1  0
 18 12  1  0
  3 24  1  0
  3 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 23 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Centrax	Kegg
Parke davis brand OF prazepam	HMDB
Warner-lambert brand OF prazepam	HMDB
Demetrin	HMDB
Pfizer brand OF prazepam	HMDB
Reapam	HMDB
Lysanxia	HMDB
mono Demetrin	HMDB
United drug brand OF prazepam	HMDB

Chemical Formula

C₁₉H₁₇ClN₂O

Average Molecular Weight

324.804

Monoisotopic Molecular Weight

324.102940883

IUPAC Name

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

Traditional Name

prazepam

CAS Registry Number

2955-38-6

SMILES

ClC1=CC2=C(C=C1)N(CC1CC1)C(=O)CN=C2C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H17ClN2O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)21-11-18(23)22(17)12-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2

InChI Key

MWQCHHACWWAQLJ-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

benzodiazepine (CHEBI:8362 )

Ontology

Disposition

Biological location

Non-excretory biofluid

Blood

Excreta

Urine

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	145 - 146 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.004 g/L	Not Available
LogP	3.73	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	174.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.004 g/L	ALOGPS
logP	3.68	ALOGPS
logP	3.86	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	3.06	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	3	ChemAxon
Refractivity	91.75 m³·mol⁻¹	ChemAxon
Polarizability	34.77 Å³	ChemAxon
Number of Rings	4	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]+	172.775	30932474
DeepCCS	[M-H]-	170.417	30932474
DeepCCS	[M-2H]-	204.321	30932474
DeepCCS	[M+Na]+	179.614	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prazepam	ClC1=CC2=C(C=C1)N(CC1CC1)C(=O)CN=C2C1=CC=CC=C1	4077.3	Standard polar	33892256
Prazepam	ClC1=CC2=C(C=C1)N(CC1CC1)C(=O)CN=C2C1=CC=CC=C1	2773.0	Standard non polar	33892256
Prazepam	ClC1=CC2=C(C=C1)N(CC1CC1)C(=O)CN=C2C1=CC=CC=C1	2639.0	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 - Prazepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-002e-3090000000-85ecde8de7c9923c1afc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00r5-3391000000-0113e86cca51d223d412	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prazepam 35V, Positive-QTOF	splash10-00b9-0098000000-121cdb4df09299b2a55f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 10V, Positive-QTOF	splash10-056r-5009000000-0f619abd238690bf909e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 20V, Positive-QTOF	splash10-0a4i-9022000000-7d0f4b34a0dc683c936a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 40V, Positive-QTOF	splash10-0a4i-9000000000-7386d4be3880cf54c894	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 10V, Negative-QTOF	splash10-00di-0029000000-d01af5072c81e6d91456	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 20V, Negative-QTOF	splash10-00xr-1097000000-243b0ed20eedd8c76c72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 40V, Negative-QTOF	splash10-0006-9460000000-91a4eb6554df563a3898	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 10V, Positive-QTOF	splash10-004i-0009000000-db9fa6607403d494beac	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 20V, Positive-QTOF	splash10-0032-0094000000-cc4f8e8cd82551329624	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 40V, Positive-QTOF	splash10-05n3-4190000000-fa9f154eaa14bdf4214a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 10V, Negative-QTOF	splash10-00di-0009000000-33c2d52f8e6510237ee4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 20V, Negative-QTOF	splash10-00yi-3095000000-d45edb96f10dbdf7642e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prazepam 40V, Negative-QTOF	splash10-001i-9070000000-47517480edb6242ad95f	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 DB01588	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01588	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

DB01588

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4721

KEGG Compound ID

C07366

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Prazepam

METLIN ID

Not Available

PubChem Compound

4890

PDB ID

Not Available

ChEBI ID

195969

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

Not Available

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

Enzyme Details

2. Gamma-aminobutyric acid receptor subunit gamma-2

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

References

Enzyme Details

3. Gamma-aminobutyric acid receptor subunit alpha-1

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

References

Enzyme Details

4. Gamma-aminobutyric acid receptor subunit alpha-2

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

References

Enzyme Details

5. Gamma-aminobutyric acid receptor subunit alpha-3

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

References

Enzyme Details

6. Gamma-aminobutyric acid receptor subunit alpha-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

7. 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

8. 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

9. 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

10. 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

Only showing the first 10 proteins. There are 17 proteins in total.

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Showing metabocard for Prazepam (HMDB0015527)

MOL for HMDB0015527 (Prazepam)

3D MOL for HMDB0015527 (Prazepam)

3D SDF for HMDB0015527 (Prazepam)

3D-SDF for HMDB0015527 (Prazepam)

PDB for HMDB0015527 (Prazepam)

3D PDB for HMDB0015527 (Prazepam)

SMILES for HMDB0015527 (Prazepam)

INCHI for HMDB0015527 (Prazepam)

Structure for HMDB0015527 (Prazepam)

3D Structure for HMDB0015527 (Prazepam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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