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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:52:37 UTC

Update Date

2019-07-23 07:15:54 UTC

HMDB ID

HMDB0061175

Secondary Accession Numbers

HMDB61175

Metabolite Identification

Common Name

p-Hydroxynordiazepam

Description

p-Hydroxynordiazepam is a metabolite of clorazepate. Clorazepate (marketed under the brand names Tranxene and Novo-Clopate), also known as clorazepate dipotassium, is a drug that is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative, hypnotic and skeletal muscle relaxant properties. Clorazepate is a prodrug for desmethyldiazepam, which is rapidly produced as an active metabolite. Desmethyldiazepam is responsible for most of the therapeutic effects of clorazepate. (Wikipedia)

Structure

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

HMDB0061175
     RDKit          3D
p-Hydroxynordiazepam
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.3592   -2.9810    1.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785   -2.0004    1.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183   -2.2399    1.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543   -1.7598    0.9501 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147   -0.6315    0.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1511   -0.4379   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -1.4684   -0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -1.4765   -1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4424   -0.4939   -2.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720   -0.5135   -2.9154 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4906    0.4989   -2.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    0.5428   -1.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180    0.4882    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2826    1.7107    0.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9840    2.8909    0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243    4.4406    0.6675 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3588    2.8216    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243    1.5908    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3122    0.4250    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081   -0.7604    0.7607 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1203   -1.6852    2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -3.3137    2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814   -2.2680    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384   -2.2778   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3991   -0.0457   -2.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6831    1.2748   -2.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6400    1.3187   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7887    1.7227    0.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    3.7493    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988    1.5381    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833   -0.6597    0.4783 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
  9 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20  2  1  0
 12  6  1  0
 19 13  1  0
  3 21  1  0
  3 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
M  END

  Mrv0541 07221312522D          

 20 22  0  0  0  0            999 V2000
   -5.1563    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8707    1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8707    0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1563    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418    0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418    1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273    2.2098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0129    0.9723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9023    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4898    2.9243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3190    1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0129   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0129   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -2.7402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5852    0.5598    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  6  2  0  0  0  0
  7  6  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12  9  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061175

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1=NCC(=O)NC2=CC=C(Cl)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H11ClN2O2/c16-10-3-6-13-12(7-10)15(17-8-14(20)18-13)9-1-4-11(19)5-2-9/h1-7,19H,8H2,(H,18,20)

> <INCHI_KEY>
WVHIBVZUJQMFON-UHFFFAOYSA-N

> <FORMULA>
C15H11ClN2O2

> <MOLECULAR_WEIGHT>
286.713

> <EXACT_MASS>
286.050905313

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.426477313214267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.9084551769999996

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.301083636244574

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.127587076664625

> <JCHEM_PKA_STRONGEST_BASIC>
2.742728942142381

> <JCHEM_POLAR_SURFACE_AREA>
61.69

> <JCHEM_REFRACTIVITY>
78.6769

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-chloro-5-(4-hydroxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061175
     RDKit          3D
p-Hydroxynordiazepam
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.3592   -2.9810    1.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785   -2.0004    1.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183   -2.2399    1.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543   -1.7598    0.9501 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147   -0.6315    0.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1511   -0.4379   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -1.4684   -0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -1.4765   -1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4424   -0.4939   -2.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720   -0.5135   -2.9154 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4906    0.4989   -2.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    0.5428   -1.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180    0.4882    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2826    1.7107    0.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9840    2.8909    0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243    4.4406    0.6675 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3588    2.8216    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243    1.5908    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3122    0.4250    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081   -0.7604    0.7607 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1203   -1.6852    2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -3.3137    2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814   -2.2680    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384   -2.2778   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3991   -0.0457   -2.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6831    1.2748   -2.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6400    1.3187   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7887    1.7227    0.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    3.7493    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988    1.5381    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833   -0.6597    0.4783 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
  9 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20  2  1  0
 12  6  1  0
 19 13  1  0
  3 21  1  0
  3 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
M  END

HEADER    PROTEIN                                 22-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUL-13         0                                  
HETATM    1  C   UNK     0      -9.625   4.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.959   3.355   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.959   1.815   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.625   1.045   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.291   1.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.291   3.355   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -6.958   4.125   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -6.958   1.045   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -5.624   1.815   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -5.418   4.125   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.648   5.459   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.329   3.036   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.958  -0.495   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.291  -1.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.291  -2.805   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.958  -3.575   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.624  -2.805   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.624  -1.265   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.958  -5.115   0.000  0.00  0.00           O+0
HETATM   20 Cl   UNK     0     -12.292   1.045   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   13                                                  
CONECT    9    8   12                                                       
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    9                                                       
CONECT   13    8   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   13   17                                                       
CONECT   19   16                                                            
CONECT   20    3                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0061175
HETATM    1  O1  UNL     1      -3.359  -2.981   1.166  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.579  -2.000   1.246  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.218  -2.240   1.827  1.00  0.00           C  
HETATM    4  N1  UNL     1      -0.154  -1.760   0.950  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.015  -0.631   0.342  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.151  -0.438  -0.476  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.109  -1.468  -0.372  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.204  -1.477  -1.165  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.442  -0.494  -2.107  1.00  0.00           C  
HETATM   10  O2  UNL     1       4.572  -0.513  -2.915  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.491   0.499  -2.189  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.363   0.543  -1.401  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.918   0.488   0.526  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.283   1.711   0.539  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.984   2.891   0.666  1.00  0.00           C  
HETATM   16 CL1  UNL     1      -0.124   4.441   0.667  1.00  0.00          CL  
HETATM   17  C13 UNL     1      -2.359   2.822   0.786  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.024   1.591   0.780  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.312   0.425   0.653  1.00  0.00           C  
HETATM   20  N2  UNL     1      -3.108  -0.760   0.761  1.00  0.00           N  
HETATM   21  H1  UNL     1      -1.120  -1.685   2.775  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.131  -3.314   2.023  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.981  -2.268   0.348  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.938  -2.278  -1.076  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.399  -0.046  -2.583  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.683   1.275  -2.936  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.640   1.319  -1.571  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.789   1.723   0.506  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.892   3.749   0.882  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.099   1.538   0.872  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.083  -0.660   0.478  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   21   22
CONECT    4    5    5
CONECT    5    6   13
CONECT    6    7    7   12
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   11
CONECT   10   25
CONECT   11   12   12   26
CONECT   12   27
CONECT   13   14   14   19
CONECT   14   15   28
CONECT   15   16   17   17
CONECT   17   18   29
CONECT   18   19   19   30
CONECT   19   20
CONECT   20   31
END

HMDB0061175
     RDKit          3D
p-Hydroxynordiazepam
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.3592   -2.9810    1.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785   -2.0004    1.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183   -2.2399    1.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543   -1.7598    0.9501 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147   -0.6315    0.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1511   -0.4379   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -1.4684   -0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -1.4765   -1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4424   -0.4939   -2.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720   -0.5135   -2.9154 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4906    0.4989   -2.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    0.5428   -1.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180    0.4882    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2826    1.7107    0.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9840    2.8909    0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243    4.4406    0.6675 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3588    2.8216    0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243    1.5908    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3122    0.4250    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081   -0.7604    0.7607 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1203   -1.6852    2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -3.3137    2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814   -2.2680    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384   -2.2778   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3991   -0.0457   -2.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6831    1.2748   -2.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6400    1.3187   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7887    1.7227    0.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    3.7493    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988    1.5381    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833   -0.6597    0.4783 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
  9 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20  2  1  0
 12  6  1  0
 19 13  1  0
  3 21  1  0
  3 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₁ClN₂O₂

Average Molecular Weight

286.713

Monoisotopic Molecular Weight

286.050905313

IUPAC Name

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

Traditional Name

7-chloro-5-(4-hydroxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1=NCC(=O)NC2=CC=C(Cl)C=C12

InChI Identifier

InChI=1S/C15H11ClN2O2/c16-10-3-6-13-12(7-10)15(17-8-14(20)18-13)9-1-4-11(19)5-2-9/h1-7,19H,8H2,(H,18,20)

InChI Key

WVHIBVZUJQMFON-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
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Ketimine
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organohalogen compound
Organic oxygen compound
Imine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organochloride
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061175)

Organ

Liver (HMDB: HMDB0061175)
Kidney (HMDB: HMDB0061175)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061175)

Cellular substructure

Cytoplasm (HMDB: HMDB0061175)
Membrane (HMDB: HMDB0061175)

Source

Endogenous

Endogenous (HMDB: HMDB0061175)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.08	ALOGPS
logP	2.91	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	2.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.68 m³·mol⁻¹	ChemAxon
Polarizability	28.43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	195.848	30932474
DeepCCS	[M+Na]+	171.413	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.5	32859911
AllCCS	[M-H]-	163.6	32859911
AllCCS	[M+Na-2H]-	162.9	32859911
AllCCS	[M+HCOO]-	162.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Hydroxynordiazepam	OC1=CC=C(C=C1)C1=NCC(=O)NC2=CC=C(Cl)C=C12	4106.8	Standard polar	33892256
p-Hydroxynordiazepam	OC1=CC=C(C=C1)C1=NCC(=O)NC2=CC=C(Cl)C=C12	2764.8	Standard non polar	33892256
p-Hydroxynordiazepam	OC1=CC=C(C=C1)C1=NCC(=O)NC2=CC=C(Cl)C=C12	3003.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
p-Hydroxynordiazepam,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=NCC(=O)NC3=CC=C(Cl)C=C23)C=C1	2802.7	Semi standard non polar	33892256
p-Hydroxynordiazepam,1TMS,isomer #2	C[Si](C)(C)N1C(=O)CN=C(C2=CC=C(O)C=C2)C2=CC(Cl)=CC=C21	2595.8	Semi standard non polar	33892256
p-Hydroxynordiazepam,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=NCC(=O)N([Si](C)(C)C)C3=CC=C(Cl)C=C23)C=C1	2633.0	Semi standard non polar	33892256
p-Hydroxynordiazepam,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=NCC(=O)N([Si](C)(C)C)C3=CC=C(Cl)C=C23)C=C1	2705.1	Standard non polar	33892256
p-Hydroxynordiazepam,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=NCC(=O)N([Si](C)(C)C)C3=CC=C(Cl)C=C23)C=C1	3533.5	Standard polar	33892256
p-Hydroxynordiazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=NCC(=O)NC3=CC=C(Cl)C=C23)C=C1	3025.9	Semi standard non polar	33892256
p-Hydroxynordiazepam,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)CN=C(C2=CC=C(O)C=C2)C2=CC(Cl)=CC=C21	2889.3	Semi standard non polar	33892256
p-Hydroxynordiazepam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=NCC(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(Cl)C=C23)C=C1	3072.9	Semi standard non polar	33892256
p-Hydroxynordiazepam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=NCC(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(Cl)C=C23)C=C1	3145.6	Standard non polar	33892256
p-Hydroxynordiazepam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=NCC(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(Cl)C=C23)C=C1	3618.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxynordiazepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0190000000-ea8512774efe85a86eac	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxynordiazepam GC-MS (1 TMS) - 70eV, Positive	splash10-00di-5149000000-fee75829e8d0d9336a11	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxynordiazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 10V, Positive-QTOF	splash10-000i-0090000000-09501cfdc7827641575c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 20V, Positive-QTOF	splash10-000i-0190000000-dda2b6cc25174406a8e1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 40V, Positive-QTOF	splash10-0a4i-4940000000-08b58d1f8704776f2b64	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 10V, Negative-QTOF	splash10-000i-0090000000-dc705fc4acffd7c9a81b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 20V, Negative-QTOF	splash10-000i-0090000000-373215bec845c07082a7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 40V, Negative-QTOF	splash10-0006-9220000000-032efe3084a110b4ef6f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 10V, Positive-QTOF	splash10-000i-0090000000-741114b1038b061132fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 20V, Positive-QTOF	splash10-000i-0090000000-741114b1038b061132fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 40V, Positive-QTOF	splash10-0api-1490000000-fcf3b6550b5e8ef9bf24	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 10V, Negative-QTOF	splash10-000i-0090000000-ba99e644d5930e82ef06	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 20V, Negative-QTOF	splash10-000i-4090000000-7c3e7a7ed7085d3eb5c3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxynordiazepam 40V, Negative-QTOF	splash10-001l-9000000000-9e5a564da6e43c5052df	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

87025

PDB ID

Not Available

ChEBI ID

Not Available

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

Showing metabocard for p-Hydroxynordiazepam (HMDB0061175)

MOL for HMDB0061175 (p-Hydroxynordiazepam)

3D MOL for HMDB0061175 (p-Hydroxynordiazepam)

3D SDF for HMDB0061175 (p-Hydroxynordiazepam)

3D-SDF for HMDB0061175 (p-Hydroxynordiazepam)

PDB for HMDB0061175 (p-Hydroxynordiazepam)

3D PDB for HMDB0061175 (p-Hydroxynordiazepam)

SMILES for HMDB0061175 (p-Hydroxynordiazepam)

INCHI for HMDB0061175 (p-Hydroxynordiazepam)

Structure for HMDB0061175 (p-Hydroxynordiazepam)

3D Structure for HMDB0061175 (p-Hydroxynordiazepam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra