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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:58:34 UTC

Update Date

2021-09-26 22:54:40 UTC

HMDB ID

HMDB0245930

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one

Description

5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one, also known as 3-methylclonazepam, 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 5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-(2-chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0245930
     RDKit          3D
5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.6529   -3.7563    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5324   -2.2901    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -1.8000    0.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -0.5952   -0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3989   -0.3484   -0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    0.8236   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200    0.8990   -1.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0115   -0.2351   -1.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5131   -1.4533   -1.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2335   -1.4847   -0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6558   -3.0653   -0.3230 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077    0.5712    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852    1.5966    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051    2.7935    1.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    3.8273    1.6909 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.7838    3.6988    1.7456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104    5.0094    2.1213 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6736    2.9976    1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171    1.9864    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9703    0.8000    0.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9558   -0.1982   -0.1149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -1.6123    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -2.3539   -0.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107   -4.3668    0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6884   -4.1048    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -3.8841   -0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895   -2.0857    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2938    1.7179   -1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5924    1.8668   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0193   -0.1719   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -2.3383   -1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444    1.3988    0.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238    3.9247    1.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808    2.0684    0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8206    0.1645   -0.4940 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22  2  1  0
 10  5  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 18 33  1  0
 19 34  1  0
 21 35  1  0
M  CHG  2  15   1  17  -1
M  END


  Mrv1652309112100582D          

 23 25  0  0  0  0            999 V2000
    4.5529    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7279    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    1.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8843    0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    1.0173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    2.7691    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.9373    2.3566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    3.5941    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.5656    2.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    2.6874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3821    3.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5937    3.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4101    4.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0149    5.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032    5.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9868    4.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752    3.9933    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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  2  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  CHG  2  12   1  14  -1
M  END
> <DATABASE_ID>
HMDB0245930

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(=C2)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12ClN3O3/c1-9-16(21)19-14-7-6-10(20(22)23)8-12(14)15(18-9)11-4-2-3-5-13(11)17/h2-9H,1H3,(H,19,21)

> <INCHI_KEY>
LMUVYJCAFWGNSY-UHFFFAOYSA-N

> <FORMULA>
C16H12ClN3O3

> <MOLECULAR_WEIGHT>
329.74

> <EXACT_MASS>
329.056719

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
31.59354879597668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.7207689303333327

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.570605130593696

> <JCHEM_PKA_STRONGEST_BASIC>
1.649718349464855

> <JCHEM_POLAR_SURFACE_AREA>
84.6

> <JCHEM_REFRACTIVITY>
87.51040000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(2-chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245930
     RDKit          3D
5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.6529   -3.7563    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5324   -2.2901    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -1.8000    0.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -0.5952   -0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3989   -0.3484   -0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    0.8236   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200    0.8990   -1.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0115   -0.2351   -1.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5131   -1.4533   -1.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2335   -1.4847   -0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6558   -3.0653   -0.3230 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077    0.5712    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852    1.5966    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051    2.7935    1.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    3.8273    1.6909 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.7838    3.6988    1.7456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104    5.0094    2.1213 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6736    2.9976    1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171    1.9864    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9703    0.8000    0.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9558   -0.1982   -0.1149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -1.6123    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -2.3539   -0.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107   -4.3668    0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6884   -4.1048    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -3.8841   -0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895   -2.0857    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2938    1.7179   -1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5924    1.8668   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0193   -0.1719   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -2.3383   -1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444    1.3988    0.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238    3.9247    1.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808    2.0684    0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8206    0.1645   -0.4940 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22  2  1  0
 10  5  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 18 33  1  0
 19 34  1  0
 21 35  1  0
M  CHG  2  15   1  17  -1
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       8.499   3.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.959   3.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.291   2.242   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.251   1.038   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.789   1.899   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.585   2.859   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.585   4.399   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.251   5.169   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.918   4.399   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.918   2.859   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.251   2.089   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.416   5.169   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0      -1.750   4.399   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.416   6.709   0.000  0.00  0.00           O-1
HETATM   15  C   UNK     0       4.789   5.359   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.291   5.017   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       4.447   6.861   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.975   7.315   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.632   8.816   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.761   9.863   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.233   9.409   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.575   7.908   0.000  0.00  0.00           C+0
HETATM   23 Cl   UNK     0       7.047   7.454   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    7   16   17                                                  
CONECT   16   15    2                                                       
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0254397
HETATM    1  C1  UNL     1       2.651  -1.217   1.573  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.511  -1.500   0.121  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.109  -1.652  -0.272  1.00  0.00           N  
HETATM    4  C3  UNL     1       0.184  -0.733  -0.375  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.132  -1.129  -0.793  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.390  -2.512  -0.786  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.537  -3.066  -1.281  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.519  -2.242  -1.826  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.292  -0.890  -1.849  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.106  -0.356  -1.337  1.00  0.00           C  
HETATM   11 CL1  UNL     1      -1.892   1.360  -1.686  1.00  0.00          CL  
HETATM   12  C10 UNL     1       0.351   0.635   0.108  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.769   1.089   0.780  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.763   2.357   1.309  1.00  0.00           C  
HETATM   15  N2  UNL     1      -1.891   2.877   2.006  1.00  0.00           N1+
HETATM   16  O1  UNL     1      -1.858   4.028   2.469  1.00  0.00           O  
HETATM   17  O2  UNL     1      -3.029   2.137   2.185  1.00  0.00           O1-
HETATM   18  C13 UNL     1       0.385   3.136   1.143  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.509   2.683   0.474  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.469   1.419  -0.037  1.00  0.00           C  
HETATM   21  N3  UNL     1       2.737   1.000  -0.609  1.00  0.00           N  
HETATM   22  C16 UNL     1       3.168  -0.371  -0.641  1.00  0.00           C  
HETATM   23  O3  UNL     1       4.165  -0.633  -1.359  1.00  0.00           O  
HETATM   24  H1  UNL     1       1.917  -0.496   1.971  1.00  0.00           H  
HETATM   25  H2  UNL     1       2.666  -2.138   2.199  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.661  -0.735   1.723  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.093  -2.399  -0.140  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.659  -3.199  -0.373  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.738  -4.120  -1.278  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.429  -2.678  -2.216  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.066  -0.239  -2.279  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.639   0.447   0.921  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.389   4.147   1.563  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.402   3.258   0.331  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.342   1.733  -0.990  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   22   27
CONECT    3    4    4
CONECT    4    5   12
CONECT    5    6    6   10
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11
CONECT   12   13   13   20
CONECT   13   14   32
CONECT   14   15   18   18
CONECT   15   16   16   17
CONECT   18   19   33
CONECT   19   20   20   34
CONECT   20   21
CONECT   21   22   35
CONECT   22   23   23
END

HMDB0245930
     RDKit          3D
5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.6529   -3.7563    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5324   -2.2901    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -1.8000    0.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -0.5952   -0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3989   -0.3484   -0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    0.8236   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200    0.8990   -1.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0115   -0.2351   -1.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5131   -1.4533   -1.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2335   -1.4847   -0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6558   -3.0653   -0.3230 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077    0.5712    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852    1.5966    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051    2.7935    1.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    3.8273    1.6909 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.7838    3.6988    1.7456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104    5.0094    2.1213 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6736    2.9976    1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171    1.9864    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9703    0.8000    0.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9558   -0.1982   -0.1149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -1.6123    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -2.3539   -0.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107   -4.3668    0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6884   -4.1048    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -3.8841   -0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895   -2.0857    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2938    1.7179   -1.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5924    1.8668   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0193   -0.1719   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -2.3383   -1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444    1.3988    0.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238    3.9247    1.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808    2.0684    0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8206    0.1645   -0.4940 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22  2  1  0
 10  5  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 18 33  1  0
 19 34  1  0
 21 35  1  0
M  CHG  2  15   1  17  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Methylclonazepam	HMDB
Meclonazepam	HMDB
Meclonazepam, (R)-isomer	HMDB
Meclonazepam, (S)-isomer	HMDB

Chemical Formula

C₁₆H₁₂ClN₃O₃

Average Molecular Weight

329.74

Monoisotopic Molecular Weight

329.056719

IUPAC Name

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

Traditional Name

5-(2-chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one

CAS Registry Number

Not Available

SMILES

CC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(=C2)[N+]([O-])=O

InChI Identifier

InChI=1S/C16H12ClN3O3/c1-9-16(21)19-14-7-6-10(20(22)23)8-12(14)15(18-9)11-4-2-3-5-13(11)17/h2-9H,1H3,(H,19,21)

InChI Key

LMUVYJCAFWGNSY-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
Nitroaromatic compound
Halobenzene
Chlorobenzene
Benzenoid
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Organic nitro compound
Secondary carboxylic acid amide
C-nitro compound
Lactam
Ketimine
Carboxamide group
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Imine
Carbonyl group
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 (PMID: 31557052)

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
logP	3.17	ALOGPS
logP	3.72	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	11.57	ChemAxon
pKa (Strongest Basic)	1.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.51 m³·mol⁻¹	ChemAxon
Polarizability	31.59 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]+	171.133	30932474
DeepCCS	[M-H]-	168.775	30932474
DeepCCS	[M-2H]-	201.661	30932474
DeepCCS	[M+Na]+	177.296	30932474
AllCCS	[M+H]+	172.9	32859911
AllCCS	[M+H-H2O]+	169.5	32859911
AllCCS	[M+NH4]+	176.1	32859911
AllCCS	[M+Na]+	177.0	32859911
AllCCS	[M-H]-	171.6	32859911
AllCCS	[M+Na-2H]-	170.8	32859911
AllCCS	[M+HCOO]-	170.0	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one,1TMS,isomer #1	CC1N=C(C2=CC=CC=C2Cl)C2=CC([N+](=O)[O-])=CC=C2N([Si](C)(C)C)C1=O	2697.7	Semi standard non polar	33892256
5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one,1TMS,isomer #1	CC1N=C(C2=CC=CC=C2Cl)C2=CC([N+](=O)[O-])=CC=C2N([Si](C)(C)C)C1=O	2728.7	Standard non polar	33892256
5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one,1TMS,isomer #1	CC1N=C(C2=CC=CC=C2Cl)C2=CC([N+](=O)[O-])=CC=C2N([Si](C)(C)C)C1=O	3941.1	Standard polar	33892256
5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one,1TBDMS,isomer #1	CC1N=C(C2=CC=CC=C2Cl)C2=CC([N+](=O)[O-])=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	2905.2	Semi standard non polar	33892256
5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one,1TBDMS,isomer #1	CC1N=C(C2=CC=CC=C2Cl)C2=CC([N+](=O)[O-])=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	2919.3	Standard non polar	33892256
5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one,1TBDMS,isomer #1	CC1N=C(C2=CC=CC=C2Cl)C2=CC([N+](=O)[O-])=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	3960.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0il0-0194000000-ea35e86702176e7215f5	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

84289

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

93364

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one (HMDB0245930)

MOL for HMDB0245930 (5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one)

3D MOL for HMDB0245930 (5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one)

3D SDF for HMDB0245930 (5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one)

3D-SDF for HMDB0245930 (5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one)

PDB for HMDB0245930 (5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one)

3D PDB for HMDB0245930 (5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one)

SMILES for HMDB0245930 (5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one)

INCHI for HMDB0245930 (5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one)

Structure for HMDB0245930 (5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one)

3D Structure for HMDB0245930 (5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra