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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:47:58 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041919

Secondary Accession Numbers

HMDB41919

Metabolite Identification

Common Name

Lormetazepam

Description

Lormetazepam (INN, or methyl-lorazepam, is a drug which is a short to intermediate acting 3-hydroxy benzodiazepine derivative. It possesses hypnotic, anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Lormetazepam is considered a hypnotic benzodiazepine and is officially indicated for moderate to severe insomnia. Lormetazepam is a short-acting benzodiazepine and is sometimes used in patients who have difficulty in maintaining sleep or falling asleep. Hypnotics should only be used on a short-term basis or, in those with chronic insomnia, on an occasional basis.

Structure

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

HMDB0041919
     RDKit          3D
Lormetazepam
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.7016   -0.1582    1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -0.3402    0.1960 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3574   -1.5155   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1132   -2.4644   -0.3735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213   -1.7460   -1.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717   -3.0618   -2.0628 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0262   -1.4781   -1.1530 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682   -0.4704   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559   -0.4654   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6813   -1.3863   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -1.5728   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942   -0.8918    0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -0.0002    1.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    0.1952    0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265    1.1751    2.1054 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    0.7215   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4324    1.9071   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875    3.1109   -0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687    4.5488   -0.1934 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211    3.1752    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395    1.9872    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6392    0.7799    0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4883    0.2962    2.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5370    0.3987    0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1381   -1.1481    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.0947   -2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553   -3.6921   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313   -1.9461   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -2.2835   -0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6305   -1.0574    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2508    0.5520    2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4764    1.7932   -0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9535    4.1443    0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658    1.9877    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 14  9  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 17 32  1  0
 20 33  1  0
 21 34  1  0
M  END


  Mrv0541 02241221382D          

 22 24  0  0  0  0            999 V2000
    2.0548    1.1441    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6596    1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760    2.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0808    3.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8691    2.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527    2.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    1.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    0.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    0.4742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6188   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -1.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502   -1.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315   -1.1960    0.0000 N   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    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    0.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431    0.5559    0.0000 Cl  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
    2.2720   -1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479   -2.0003    0.0000 C   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 14 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041919

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C16H12Cl2N2O2/c1-20-13-7-6-9(17)8-11(13)14(19-15(21)16(20)22)10-4-2-3-5-12(10)18/h2-8,15,21H,1H3

> <INCHI_KEY>
FJIKWRGCXUCUIG-UHFFFAOYSA-N

> <FORMULA>
C16H12Cl2N2O2

> <MOLECULAR_WEIGHT>
335.185

> <EXACT_MASS>
334.027583052

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.20718392747353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
3.391391556666667

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.676469443853929

> <JCHEM_PKA_STRONGEST_BASIC>
-2.156070814774956

> <JCHEM_POLAR_SURFACE_AREA>
52.900000000000006

> <JCHEM_REFRACTIVITY>
85.8151

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lormetazepam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041919
     RDKit          3D
Lormetazepam
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.7016   -0.1582    1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -0.3402    0.1960 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3574   -1.5155   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1132   -2.4644   -0.3735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213   -1.7460   -1.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717   -3.0618   -2.0628 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0262   -1.4781   -1.1530 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682   -0.4704   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559   -0.4654   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6813   -1.3863   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -1.5728   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942   -0.8918    0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -0.0002    1.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    0.1952    0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265    1.1751    2.1054 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    0.7215   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4324    1.9071   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875    3.1109   -0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687    4.5488   -0.1934 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211    3.1752    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395    1.9872    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6392    0.7799    0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4883    0.2962    2.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5370    0.3987    0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1381   -1.1481    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.0947   -2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553   -3.6921   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313   -1.9461   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -2.2835   -0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6305   -1.0574    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2508    0.5520    2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4764    1.7932   -0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9535    4.1443    0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658    1.9877    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 14  9  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 17 32  1  0
 20 33  1  0
 21 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.836   2.136   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0       4.965   3.183   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.622   4.684   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.751   5.732   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.222   5.278   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.565   3.777   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.436   2.729   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.779   1.228   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.280   0.885   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.948  -0.502   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.488  -0.502   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.280  -1.890   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.240  -3.094   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       6.779  -2.233   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.575  -1.272   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.575   0.268   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.241   1.038   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.907   0.268   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       1.574   1.038   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       2.907  -1.272   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.241  -2.042   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.436  -3.734   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22   14                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0041919
HETATM    1  C1  UNL     1      -3.702  -0.158   1.015  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.562  -0.340   0.196  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.357  -1.516  -0.588  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.113  -2.464  -0.374  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.321  -1.746  -1.660  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.372  -3.062  -2.063  1.00  0.00           O  
HETATM    7  N2  UNL     1       0.026  -1.478  -1.153  1.00  0.00           N  
HETATM    8  C4  UNL     1       0.468  -0.470  -0.422  1.00  0.00           C  
HETATM    9  C5  UNL     1       1.856  -0.465  -0.053  1.00  0.00           C  
HETATM   10  C6  UNL     1       2.681  -1.386  -0.744  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.983  -1.573  -0.400  1.00  0.00           C  
HETATM   12  C8  UNL     1       4.594  -0.892   0.634  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.812  -0.000   1.317  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.467   0.195   0.969  1.00  0.00           C  
HETATM   15 CL1  UNL     1       1.527   1.175   2.105  1.00  0.00          CL  
HETATM   16  C11 UNL     1      -0.310   0.722  -0.148  1.00  0.00           C  
HETATM   17  C12 UNL     1       0.432   1.907  -0.268  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.187   3.111  -0.039  1.00  0.00           C  
HETATM   19 CL2  UNL     1       0.769   4.549  -0.193  1.00  0.00          CL  
HETATM   20  C14 UNL     1      -1.521   3.175   0.305  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.240   1.987   0.414  1.00  0.00           C  
HETATM   22  C16 UNL     1      -1.639   0.780   0.187  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.488   0.296   2.005  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.537   0.399   0.493  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.138  -1.148   1.235  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.531  -1.095  -2.526  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.555  -3.692  -1.317  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.231  -1.946  -1.572  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.590  -2.284  -0.946  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.630  -1.057   0.885  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.251   0.552   2.131  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.476   1.793  -0.578  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.954   4.144   0.475  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.266   1.988   0.679  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   22
CONECT    3    4    4    5
CONECT    5    6    7   26
CONECT    6   27
CONECT    7    8    8
CONECT    8    9   16
CONECT    9   10   10   14
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15
CONECT   16   17   17   22
CONECT   17   18   32
CONECT   18   19   20   20
CONECT   20   21   33
CONECT   21   22   22   34
END

HMDB0041919
     RDKit          3D
Lormetazepam
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.7016   -0.1582    1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -0.3402    0.1960 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3574   -1.5155   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1132   -2.4644   -0.3735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213   -1.7460   -1.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717   -3.0618   -2.0628 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0262   -1.4781   -1.1530 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682   -0.4704   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559   -0.4654   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6813   -1.3863   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -1.5728   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942   -0.8918    0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -0.0002    1.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    0.1952    0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265    1.1751    2.1054 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    0.7215   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4324    1.9071   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875    3.1109   -0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687    4.5488   -0.1934 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211    3.1752    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395    1.9872    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6392    0.7799    0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4883    0.2962    2.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5370    0.3987    0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1381   -1.1481    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.0947   -2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553   -3.6921   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313   -1.9461   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5896   -2.2835   -0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6305   -1.0574    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2508    0.5520    2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4764    1.7932   -0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9535    4.1443    0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658    1.9877    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  8 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 14  9  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 17 32  1  0
 20 33  1  0
 21 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Lorazepam	ChEBI
7-Chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one	ChEBI
7-Chloro-5-(O-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2H-1,4-benzodiazepin-2-one	ChEBI
Loramet	ChEBI
Lorazepam	ChEBI
Lormetazepamum	ChEBI
Methyllorazepam	ChEBI
N-Methyllorazepam	ChEBI
O-Chlorooxazepam	ChEBI
O-Chloroxazepam	ChEBI
()-Lorazepam	HMDB
7-chloro-5-(2-Chlorophenyl)-3-hydroxy-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one	HMDB
Ergocalm	HMDB
Noctamid	HMDB
Noctamide	HMDB

Chemical Formula

C₁₆H₁₂Cl₂N₂O₂

Average Molecular Weight

335.185

Monoisotopic Molecular Weight

334.027583052

IUPAC Name

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

Traditional Name

lormetazepam

CAS Registry Number

848-75-9

SMILES

CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C16H12Cl2N2O2/c1-20-13-7-6-9(17)8-11(13)14(19-15(21)16(20)22)10-4-2-3-5-12(10)18/h2-8,15,21H,1H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:52993 )
1,4-benzodiazepinone (CHEBI:52993 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0041919)

Cellular substructure

Membrane (HMDB: HMDB0041919)

Potato (FooDB: FOOD00175)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

sedative (HMDB: HMDB0041919)

Pharmaceutical industry

Sedative (HMDB: HMDB0041919)

Biological role

Nutrient

Nutrient (HMDB: HMDB0041919)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	206 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	169.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	2.92	ALOGPS
logP	3.39	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	10.68	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.82 m³·mol⁻¹	ChemAxon
Polarizability	32.21 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]+	169.375	30932474
DeepCCS	[M-H]-	167.017	30932474
DeepCCS	[M-2H]-	200.447	30932474
DeepCCS	[M+Na]+	175.674	30932474
AllCCS	[M+H]+	172.1	32859911
AllCCS	[M+H-H2O]+	168.6	32859911
AllCCS	[M+NH4]+	175.3	32859911
AllCCS	[M+Na]+	176.2	32859911
AllCCS	[M-H]-	170.6	32859911
AllCCS	[M+Na-2H]-	169.9	32859911
AllCCS	[M+HCOO]-	169.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lormetazepam	CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl	4101.8	Standard polar	33892256
Lormetazepam	CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl	2660.5	Standard non polar	33892256
Lormetazepam	CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl	2710.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lormetazepam,1TMS,isomer #1	CN1C(=O)C(O[Si](C)(C)C)N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C21	2757.2	Semi standard non polar	33892256
Lormetazepam,1TBDMS,isomer #1	CN1C(=O)C(O[Si](C)(C)C(C)(C)C)N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C21	2899.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Lormetazepam EI-B (Non-derivatized)	splash10-0a4i-1219000000-503deaa645713d28cd79	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Lormetazepam EI-B (Non-derivatized)	splash10-0a4i-1219000000-503deaa645713d28cd79	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lormetazepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-1795000000-54ec577d366419e67a57	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lormetazepam GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9327000000-b97471e8ca7fa14dc66e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lormetazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lormetazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-2739000000-db8dc59f3b0cd2b1f961	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 10V, Positive-QTOF	splash10-000i-0029000000-b740d967344307057276	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 20V, Positive-QTOF	splash10-000i-0229000000-85f6cd437be844945454	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 40V, Positive-QTOF	splash10-000l-1930000000-5956d587779e5dd037d0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 10V, Negative-QTOF	splash10-001i-0009000000-f8c21520624f2329615b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 20V, Negative-QTOF	splash10-0059-0395000000-294d5b2fafa29dcbd1ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 40V, Negative-QTOF	splash10-0bvi-5592000000-60b8f74cbf9e0379ec5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 10V, Positive-QTOF	splash10-000i-0029000000-5de67bfbe23ce4a7f6ba	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 20V, Positive-QTOF	splash10-002r-0069000000-a5d15166483d3298eae0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 40V, Positive-QTOF	splash10-03fr-0290000000-81ca3eb9e5b8757a9575	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 10V, Negative-QTOF	splash10-001j-0079000000-7a1a623dc11cf39fac8e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 20V, Negative-QTOF	splash10-001j-3096000000-66c851b8c2851ab6f2f7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lormetazepam 40V, Negative-QTOF	splash10-001i-9141000000-2888eb8630631357a90b	2021-09-25	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

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

DB13872

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007119

KNApSAcK ID

Not Available

Chemspider ID

12750

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lormetazepam

METLIN ID

Not Available

PubChem Compound

13314

PDB ID

Not Available

ChEBI ID

52993

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 Lormetazepam (HMDB0041919)

MOL for HMDB0041919 (Lormetazepam)

3D MOL for HMDB0041919 (Lormetazepam)

3D SDF for HMDB0041919 (Lormetazepam)

3D-SDF for HMDB0041919 (Lormetazepam)

PDB for HMDB0041919 (Lormetazepam)

3D PDB for HMDB0041919 (Lormetazepam)

SMILES for HMDB0041919 (Lormetazepam)

INCHI for HMDB0041919 (Lormetazepam)

Structure for HMDB0041919 (Lormetazepam)

3D Structure for HMDB0041919 (Lormetazepam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra