Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:20:49 UTC

Update Date

2021-09-26 23:07:58 UTC

HMDB ID

HMDB0254160

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lopirazepam

Description

Lopirazepam belongs to the class of organic compounds known as pyridodiazepines. These are heterocyclic compounds containing a pyridine fused to a diazepine ring. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Diazepine is a 7-membered ring consisting of five carbon atoms and two nitrogen centers. Based on a literature review very few articles have been published on Lopirazepam. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lopirazepam is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lopirazepam 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

HMDB0254160
     RDKit          3D
Lopirazepam
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.8033   -3.0963    1.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2610   -2.1447    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7072   -0.8502    0.9021 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1377    0.3731    0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    1.3865    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6488    2.5734   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3469    2.7081   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877    4.1883   -1.5253 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4583    1.7032   -0.6032 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    0.5178   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -0.4492    0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5939   -0.0705    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680   -1.0425   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084   -0.8565   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3645    0.3218    0.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    1.2838    0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0682    1.0894    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0459    2.3393    1.3612 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0141   -1.7304   -0.1656 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1749   -2.4691   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6485   -2.1654   -1.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820   -0.7215    1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527    1.1883    0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3505    3.3606   -0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903   -1.9684   -0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5946   -1.6500   -0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4225    0.4833    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7833    2.2184    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312   -3.5518   -0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5633   -2.9691   -2.2600 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 11 19  2  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 10  4  1  0
 17 12  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 20 29  1  0
 21 30  1  0
M  END


  Mrv1652309112115212D          

 21 23  0  0  0  0            999 V2000
    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
    2.6596    1.7052    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
    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 N   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
    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
    0.8431    0.5559    0.0000 Cl  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
    4.8410    1.7800    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
  9 20  1  0  0  0  0
  4 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254160

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(Cl)=N2

> <INCHI_IDENTIFIER>
InChI=1S/C14H9Cl2N3O2/c15-8-4-2-1-3-7(8)11-12-9(5-6-10(16)18-12)17-13(20)14(21)19-11/h1-6,14,21H,(H,17,20)

> <INCHI_KEY>
JEJOFYTVMFVKQA-UHFFFAOYSA-N

> <FORMULA>
C14H9Cl2N3O2

> <MOLECULAR_WEIGHT>
322.15

> <EXACT_MASS>
321.0071819

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
29.661242274659802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-5-(2-chlorophenyl)-3-hydroxy-1H,2H,3H-pyrido[3,2-e][1,4]diazepin-2-one

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.9156805636666663

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.87117092836772

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.430518068152208

> <JCHEM_PKA_STRONGEST_BASIC>
-1.948322450090314

> <JCHEM_POLAR_SURFACE_AREA>
74.58

> <JCHEM_REFRACTIVITY>
81.23160000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lopirazepam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254160
     RDKit          3D
Lopirazepam
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.8033   -3.0963    1.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2610   -2.1447    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7072   -0.8502    0.9021 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1377    0.3731    0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    1.3865    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6488    2.5734   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3469    2.7081   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877    4.1883   -1.5253 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4583    1.7032   -0.6032 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    0.5178   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -0.4492    0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5939   -0.0705    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680   -1.0425   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084   -0.8565   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3645    0.3218    0.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    1.2838    0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0682    1.0894    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0459    2.3393    1.3612 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0141   -1.7304   -0.1656 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1749   -2.4691   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6485   -2.1654   -1.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820   -0.7215    1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527    1.1883    0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3505    3.3606   -0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903   -1.9684   -0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5946   -1.6500   -0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4225    0.4833    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7833    2.2184    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312   -3.5518   -0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5633   -2.9691   -2.2600 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 11 19  2  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 10  4  1  0
 17 12  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 20 29  1  0
 21 30  1  0
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       4.622   4.684   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.751   5.732   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.222   5.278   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.565   3.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.436   2.729   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.965   3.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.779   1.228   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       8.280   0.885   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       8.948  -0.502   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.280  -1.890   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.240  -3.094   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       6.779  -2.233   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.575  -1.272   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.575   0.268   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.241   1.038   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.907   0.268   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.907  -1.272   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.241  -2.042   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  O   UNK     0      10.488  -0.502   0.000  0.00  0.00           O+0
HETATM   21 Cl   UNK     0       9.037   3.323   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13    7   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16                                                            
CONECT   20    9                                                            
CONECT   21    4                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0254160
HETATM    1  O1  UNL     1       2.803  -3.096   1.102  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.261  -2.145   0.558  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.707  -0.850   0.902  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.138   0.373   0.387  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.056   1.387   0.227  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.649   2.573  -0.364  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.347   2.708  -0.771  1.00  0.00           C  
HETATM    8 CL1  UNL     1       0.788   4.188  -1.525  1.00  0.00          CL  
HETATM    9  N2  UNL     1       0.458   1.703  -0.603  1.00  0.00           N  
HETATM   10  C6  UNL     1       0.821   0.518  -0.025  1.00  0.00           C  
HETATM   11  C7  UNL     1      -0.224  -0.449   0.016  1.00  0.00           C  
HETATM   12  C8  UNL     1      -1.594  -0.070   0.131  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.568  -1.042  -0.218  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.908  -0.857  -0.052  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.364   0.322   0.479  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.452   1.284   0.831  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.068   1.089   0.661  1.00  0.00           C  
HETATM   18 CL2  UNL     1      -1.046   2.339   1.361  1.00  0.00          CL  
HETATM   19  N3  UNL     1      -0.014  -1.730  -0.166  1.00  0.00           N  
HETATM   20  C14 UNL     1       1.175  -2.469  -0.421  1.00  0.00           C  
HETATM   21  O2  UNL     1       1.648  -2.165  -1.688  1.00  0.00           O  
HETATM   22  H1  UNL     1       3.482  -0.722   1.536  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.053   1.188   0.581  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.350   3.361  -0.492  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.190  -1.968  -0.639  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.595  -1.650  -0.344  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.422   0.483   0.614  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.783   2.218   1.248  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.931  -3.552  -0.322  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.563  -2.969  -2.260  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   22
CONECT    4    5    5   10
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8    9
CONECT    9   10   10
CONECT   10   11
CONECT   11   12   19   19
CONECT   12   13   13   17
CONECT   13   14   25
CONECT   14   15   15   26
CONECT   15   16   27
CONECT   16   17   17   28
CONECT   17   18
CONECT   19   20
CONECT   20   21   29
CONECT   21   30
END

HMDB0254160
     RDKit          3D
Lopirazepam
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.8033   -3.0963    1.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2610   -2.1447    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7072   -0.8502    0.9021 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1377    0.3731    0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    1.3865    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6488    2.5734   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3469    2.7081   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877    4.1883   -1.5253 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4583    1.7032   -0.6032 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    0.5178   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243   -0.4492    0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5939   -0.0705    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680   -1.0425   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084   -0.8565   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3645    0.3218    0.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    1.2838    0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0682    1.0894    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0459    2.3393    1.3612 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0141   -1.7304   -0.1656 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1749   -2.4691   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6485   -2.1654   -1.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820   -0.7215    1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527    1.1883    0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3505    3.3606   -0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903   -1.9684   -0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5946   -1.6500   -0.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4225    0.4833    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7833    2.2184    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312   -3.5518   -0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5633   -2.9691   -2.2600 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 11 19  2  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 10  4  1  0
 17 12  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 20 29  1  0
 21 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-5-(O-chlorophenyl)-7-chloro-1,2-dihydro-2H-pyrido(3,2-e)-1,4-diazepin-2-one	HMDB
Lopirazepam, monosodium salt	HMDB

Chemical Formula

C₁₄H₉Cl₂N₃O₂

Average Molecular Weight

322.15

Monoisotopic Molecular Weight

321.0071819

IUPAC Name

7-chloro-5-(2-chlorophenyl)-3-hydroxy-1H,2H,3H-pyrido[3,2-e][1,4]diazepin-2-one

Traditional Name

lopirazepam

CAS Registry Number

Not Available

SMILES

OC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(Cl)=N2

InChI Identifier

InChI=1S/C14H9Cl2N3O2/c15-8-4-2-1-3-7(8)11-12-9(5-6-10(16)18-12)17-13(20)14(21)19-11/h1-6,14,21H,(H,17,20)

InChI Key

JEJOFYTVMFVKQA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridodiazepines. These are heterocyclic compounds containing a pyridine fused to a diazepine ring. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Diazepine is a 7-membered ring consisting of five carbon atoms and two nitrogen centers.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridodiazepines

Sub Class

Not Available

Direct Parent

Pyridodiazepines

Alternative Parents

Substituents

Pyrido-para-diazepine
Alpha-amino acid or derivatives
2-halopyridine
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Pyridine
Heteroaromatic compound
Carboxamide group
Ketimine
Secondary carboxylic acid amide
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	2.5	ALOGPS
logP	2.92	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	10.43	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.58 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.23 m³·mol⁻¹	ChemAxon
Polarizability	29.66 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]+	165.831	30932474
DeepCCS	[M-H]-	163.474	30932474
DeepCCS	[M-2H]-	196.36	30932474
DeepCCS	[M+Na]+	171.925	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	14.7249 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2351.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	445.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	264.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	235.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	576.7 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	737.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	148.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1306.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	483.8 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	1410.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	406.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	432.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	433.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	202.2 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	66.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lopirazepam	OC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(Cl)=N2	4060.9	Standard polar	33892256
Lopirazepam	OC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(Cl)=N2	2449.9	Standard non polar	33892256
Lopirazepam	OC1N=C(C2=CC=CC=C2Cl)C2=C(NC1=O)C=CC(Cl)=N2	2787.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lopirazepam,2TMS,isomer #1	C[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=NC(Cl)=CC=C2N([Si](C)(C)C)C1=O	2590.9	Semi standard non polar	33892256
Lopirazepam,2TMS,isomer #1	C[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=NC(Cl)=CC=C2N([Si](C)(C)C)C1=O	2604.0	Standard non polar	33892256
Lopirazepam,2TMS,isomer #1	C[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=NC(Cl)=CC=C2N([Si](C)(C)C)C1=O	3803.6	Standard polar	33892256
Lopirazepam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=NC(Cl)=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	2896.8	Semi standard non polar	33892256
Lopirazepam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=NC(Cl)=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	2991.1	Standard non polar	33892256
Lopirazepam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1N=C(C2=CC=CC=C2Cl)C2=NC(Cl)=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	3826.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lopirazepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-00p0-1490000000-a69aef6eba7c95ffe625	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lopirazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lopirazepam GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lopirazepam GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lopirazepam GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lopirazepam GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Lopirazepam 10V, Positive-QTOF	splash10-00di-0009000000-0d106f16a14561b9e1f9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lopirazepam 20V, Positive-QTOF	splash10-00di-0019000000-d0cd1881beb441a6658e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lopirazepam 40V, Positive-QTOF	splash10-0ftu-0591000000-ff5298d83332c3b00001	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lopirazepam 10V, Negative-QTOF	splash10-014r-1198000000-4d79951edcdf2442b778	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lopirazepam 20V, Negative-QTOF	splash10-001i-9134000000-323655d7cc48e39b7171	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lopirazepam 40V, Negative-QTOF	splash10-001i-9300000000-b2cbe678ffab043fbaef	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

61926

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lopirazepam

METLIN ID

Not Available

PubChem Compound

68672

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 Lopirazepam (HMDB0254160)

MOL for HMDB0254160 (Lopirazepam)

3D MOL for HMDB0254160 (Lopirazepam)

3D SDF for HMDB0254160 (Lopirazepam)

3D-SDF for HMDB0254160 (Lopirazepam)

PDB for HMDB0254160 (Lopirazepam)

3D PDB for HMDB0254160 (Lopirazepam)

SMILES for HMDB0254160 (Lopirazepam)

INCHI for HMDB0254160 (Lopirazepam)

Structure for HMDB0254160 (Lopirazepam)

3D Structure for HMDB0254160 (Lopirazepam)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra