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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:44:51 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041867

Secondary Accession Numbers

HMDB41867

Metabolite Identification

Common Name

Demoxepam

Description

Demoxepam, also known as demoxepam(usan) or ro 5-2092 lactam, 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. Based on a literature review a significant number of articles have been published on Demoxepam.

Structure

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

HMDB0041867
     RDKit          3D
Demoxepam
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.8230    2.7868   -0.3534 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1869    1.9076   -0.3224 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.1147    0.6816   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574    0.2222    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302   -1.0600    0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9615   -1.5970    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0867   -0.8803    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945    0.3860    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034    0.9236   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130   -0.3815   -0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4724   -1.5291   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3281   -2.5824   -0.9098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220   -4.0331   -1.6987 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6365   -2.5195   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0859   -1.3793    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2087   -0.3279    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7901    0.8700    0.8818 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764    2.0916    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263    3.1130    1.1696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152    2.5225   -0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -1.6681    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623   -2.6024    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0823   -1.2958    0.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7764    0.9604   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438    1.9155   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5521   -1.5351   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2351   -3.3998   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924   -1.3159    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5618    3.9530    1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3830    3.6122   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383    2.1612   -1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  3 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
  9  4  1  0
 16 10  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 14 27  1  0
 15 28  1  0
 19 29  1  0
 20 30  1  0
 20 31  1  0
M  CHG  2   1  -1   2   1
M  END


  Mrv0541 09131211442D          

 20 22  0  0  0  0            999 V2000
    3.0808   -2.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8691   -2.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760   -1.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -1.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596   -0.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    1.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479   -0.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    0.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431    0.2691    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    2.0210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    0.3508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502    2.4825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502   -0.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18  9  1  0  0  0  0
 18 15  2  0  0  0  0
 19 14  1  0  0  0  0
 20 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041867

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=N(=O)C1

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

> <INCHI_KEY>
GGRWZBVSUZZMKS-UHFFFAOYSA-N

> <FORMULA>
C15H11ClN2O2

> <MOLECULAR_WEIGHT>
286.713

> <EXACT_MASS>
286.050905313

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.01940815946138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-2-hydroxy-5-phenyl-3H-1,4λ⁵-benzodiazepin-4-one

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
3.622717552666666

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.98960551286045

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.486436174875321

> <JCHEM_PKA_STRONGEST_BASIC>
-0.21601719477374093

> <JCHEM_POLAR_SURFACE_AREA>
61.339999999999996

> <JCHEM_REFRACTIVITY>
80.90820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
demoxepam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041867
     RDKit          3D
Demoxepam
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.8230    2.7868   -0.3534 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1869    1.9076   -0.3224 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.1147    0.6816   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574    0.2222    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302   -1.0600    0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9615   -1.5970    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0867   -0.8803    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945    0.3860    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034    0.9236   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130   -0.3815   -0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4724   -1.5291   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3281   -2.5824   -0.9098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220   -4.0331   -1.6987 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6365   -2.5195   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0859   -1.3793    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2087   -0.3279    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7901    0.8700    0.8818 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764    2.0916    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263    3.1130    1.1696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152    2.5225   -0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -1.6681    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623   -2.6024    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0823   -1.2958    0.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7764    0.9604   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438    1.9155   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5521   -1.5351   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2351   -3.3998   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924   -1.3159    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5618    3.9530    1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3830    3.6122   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383    2.1612   -1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  3 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
  9  4  1  0
 16 10  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 14 27  1  0
 15 28  1  0
 19 29  1  0
 20 30  1  0
 20 31  1  0
M  CHG  2   1  -1   2   1
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       5.751  -4.192   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.222  -3.738   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.622  -3.144   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.565  -2.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.965  -1.643   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.907   2.812   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.241   3.582   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.241   0.502   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.948   2.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.436  -1.189   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.907   1.272   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.575   1.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.575   2.812   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.280   3.430   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.779   0.312   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       1.574   0.502   0.000  0.00  0.00          Cl+0
HETATM   17  N   UNK     0       6.779   3.773   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       8.280   0.655   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       9.240   4.634   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.240  -0.549   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    7   11                                                       
CONECT    7    6   13                                                       
CONECT    8   11   12                                                       
CONECT    9   14   18                                                       
CONECT   10    4    5   15                                                  
CONECT   11    6    8   16                                                  
CONECT   12    8   13   15                                                  
CONECT   13    7   12   17                                                  
CONECT   14    9   17   19                                                  
CONECT   15   10   12   18                                                  
CONECT   16   11                                                            
CONECT   17   13   14                                                       
CONECT   18    9   15   20                                                  
CONECT   19   14                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0041867
HETATM    1  O1  UNL     1       0.823   2.787  -0.353  1.00  0.00           O1-
HETATM    2  N1  UNL     1      -0.187   1.908  -0.322  1.00  0.00           N1+
HETATM    3  C1  UNL     1       0.115   0.682  -0.071  1.00  0.00           C  
HETATM    4  C2  UNL     1       1.457   0.222   0.176  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.730  -1.060   0.662  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.961  -1.597   0.822  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.087  -0.880   0.504  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.895   0.386   0.024  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.603   0.924  -0.136  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.913  -0.381  -0.163  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.472  -1.529  -0.782  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.328  -2.582  -0.910  1.00  0.00           C  
HETATM   13 CL1  UNL     1      -0.722  -4.033  -1.699  1.00  0.00          CL  
HETATM   14  C11 UNL     1      -2.637  -2.519  -0.432  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.086  -1.379   0.181  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.209  -0.328   0.301  1.00  0.00           C  
HETATM   17  N2  UNL     1      -2.790   0.870   0.882  1.00  0.00           N  
HETATM   18  C14 UNL     1      -2.476   2.092   0.512  1.00  0.00           C  
HETATM   19  O2  UNL     1      -3.126   3.113   1.170  1.00  0.00           O  
HETATM   20  C15 UNL     1      -1.515   2.522  -0.521  1.00  0.00           C  
HETATM   21  H1  UNL     1       0.884  -1.668   1.007  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.062  -2.602   1.205  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.082  -1.296   0.626  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.776   0.960  -0.229  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.544   1.915  -0.536  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.552  -1.535  -1.194  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.235  -3.400  -0.578  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.092  -1.316   0.553  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.562   3.953   1.363  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.383   3.612  -0.526  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.838   2.161  -1.535  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   20
CONECT    3    4   10
CONECT    4    5    5    9
CONECT    5    6   21
CONECT    6    7    7   22
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   25
CONECT   10   11   11   16
CONECT   11   12   26
CONECT   12   13   14   14
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17
CONECT   17   18   18
CONECT   18   19   20
CONECT   19   29
CONECT   20   30   31
END

HMDB0041867
     RDKit          3D
Demoxepam
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.8230    2.7868   -0.3534 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1869    1.9076   -0.3224 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.1147    0.6816   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574    0.2222    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302   -1.0600    0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9615   -1.5970    0.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0867   -0.8803    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945    0.3860    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034    0.9236   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130   -0.3815   -0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4724   -1.5291   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3281   -2.5824   -0.9098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220   -4.0331   -1.6987 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6365   -2.5195   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0859   -1.3793    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2087   -0.3279    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7901    0.8700    0.8818 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764    2.0916    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263    3.1130    1.1696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152    2.5225   -0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -1.6681    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623   -2.6024    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0823   -1.2958    0.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7764    0.9604   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438    1.9155   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5521   -1.5351   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2351   -3.3998   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924   -1.3159    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5618    3.9530    1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3830    3.6122   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383    2.1612   -1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  3 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
  9  4  1  0
 16 10  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 14 27  1  0
 15 28  1  0
 19 29  1  0
 20 30  1  0
 20 31  1  0
M  CHG  2   1  -1   2   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Chlordiazepoxide lactam	HMDB
Demoxepam(usan)	HMDB
Ro 5-2092 lactam	HMDB

Chemical Formula

C₁₅H₁₁ClN₂O₂

Average Molecular Weight

286.713

Monoisotopic Molecular Weight

286.050905313

IUPAC Name

7-chloro-2-hydroxy-5-phenyl-3H-1,4λ⁵-benzodiazepin-4-one

Traditional Name

demoxepam

CAS Registry Number

963-39-3

SMILES

OC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=N(=O)C1

InChI Identifier

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

InChI Key

GGRWZBVSUZZMKS-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
Carboxamide group
Lactam
Nitrone
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic zwitterion
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041867)

Source

Exogenous

Exogenous (HMDB: HMDB0041867)

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	1.49	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	161.7	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	2.06	ALOGPS
logP	3.62	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-0.22	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.34 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.91 m³·mol⁻¹	ChemAxon
Polarizability	29.02 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	162.947	30932474
DeepCCS	[M-H]-	160.589	30932474
DeepCCS	[M-2H]-	193.905	30932474
DeepCCS	[M+Na]+	169.132	30932474
AllCCS	[M+H]+	161.8	32859911
AllCCS	[M+H-H2O]+	158.0	32859911
AllCCS	[M+NH4]+	165.4	32859911
AllCCS	[M+Na]+	166.4	32859911
AllCCS	[M-H]-	162.1	32859911
AllCCS	[M+Na-2H]-	161.3	32859911
AllCCS	[M+HCOO]-	160.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.06 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9479 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.46 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2018.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	390.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	165.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	227.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	534.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	531.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	65.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1162.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	470.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1234.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	324.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	300.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	143.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Demoxepam	OC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=N(=O)C1	3822.8	Standard polar	33892256
Demoxepam	OC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=N(=O)C1	2720.3	Standard non polar	33892256
Demoxepam	OC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=N(=O)C1	2647.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Demoxepam,1TMS,isomer #1	C[Si](C)(C)OC1=NC2=CC=C(Cl)C=C2C(C2=CC=CC=C2)=[N+]([O-])C1	2473.2	Semi standard non polar	33892256
Demoxepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=CC=C(Cl)C=C2C(C2=CC=CC=C2)=[N+]([O-])C1	2676.6	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 - Demoxepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-0290000000-ceec6e3d6d65babe4b40	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demoxepam GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9077000000-72e3465174f8b72f0325	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demoxepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demoxepam 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 - Demoxepam 10V, Positive-QTOF	splash10-000i-0090000000-eff2b31a7fc4b31fb70a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 20V, Positive-QTOF	splash10-000i-0090000000-e1dc790814c9ed52224f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 40V, Positive-QTOF	splash10-0002-9220000000-c4620663e7c8c2e76afb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 10V, Negative-QTOF	splash10-000i-0090000000-315ecd9f9e6b807fe6df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 20V, Negative-QTOF	splash10-000i-0090000000-5ab0ceb140fe4511533c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 40V, Negative-QTOF	splash10-0006-9040000000-86b97f31bb63119e2ea2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 10V, Positive-QTOF	splash10-000i-0090000000-741114b1038b061132fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 20V, Positive-QTOF	splash10-000i-0090000000-741114b1038b061132fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 40V, Positive-QTOF	splash10-0296-0090000000-72299a779982dd63c54f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 10V, Negative-QTOF	splash10-000i-0090000000-ba99e644d5930e82ef06	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 20V, Negative-QTOF	splash10-000i-0090000000-14d4564f35a283f70e18	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demoxepam 40V, Negative-QTOF	splash10-000i-0090000000-32abdd79ec82399c1bcb	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

10441314

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Demoxepam

METLIN ID

Not Available

PubChem Compound

Not Available

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 Demoxepam (HMDB0041867)

MOL for HMDB0041867 (Demoxepam)

3D MOL for HMDB0041867 (Demoxepam)

3D SDF for HMDB0041867 (Demoxepam)

3D-SDF for HMDB0041867 (Demoxepam)

PDB for HMDB0041867 (Demoxepam)

3D PDB for HMDB0041867 (Demoxepam)

SMILES for HMDB0041867 (Demoxepam)

INCHI for HMDB0041867 (Demoxepam)

Structure for HMDB0041867 (Demoxepam)

3D Structure for HMDB0041867 (Demoxepam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra