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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:46:17 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041890

Secondary Accession Numbers

HMDB41890

Metabolite Identification

Common Name

Etizolam

Description

According to the Italian P.I. sheet etizolam belongs to a new class of diazepines, thienotriazolodiazepines. This new class is easily oxidized, rapidly metabolized, and has a lower risk of accumulation, even after prolonged treatment. Etizolam has an anxiolytic action about 6 times greater than that of diazepam. Etizolam produces, especially at higher dosages, a reduction in time taken to fall asleep, an increase in total sleep time and a reduction in the number of awakenings. During tests there were not substantial changes in deep sleep. There is a reduction of REM sleep. In EEG tests of healthy volunteers Etizolam showed some characteristics of tricyclic antidepressants. Etizolam (marketed under the brand name Etilaam, Etizola, Sedekopan, Pasaden or Depas) is a thienodiazepine drug which is a benzodiazepine analog. The etizolam molecule differs from a benzodiazepine in that the benzene ring has been replaced by a thiophene ring. It possesses amnesic, anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties.

Structure

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

HMDB0041890
     RDKit          3D
Etizolam
 38 41  0  0  0  0  0  0  0  0999 V2000
    3.2323    3.4881    0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7557    3.3423    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993    1.8925    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866    1.2783    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106   -0.0395    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877   -0.6723   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    0.5744   -0.0371 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -2.0812   -0.1954 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5336   -2.5509   -0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4977   -1.6579   -1.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618   -3.8804   -0.8641 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4208   -4.2004   -0.0666 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381   -3.1051    0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184   -2.9950    1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3007   -2.0343    0.8213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1654   -0.7915    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4104   -0.1704    0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5510    1.0598   -0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875    1.6329   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9186    0.9376   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8380   -0.3198    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5920   -0.8413    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5392   -2.4492    1.1462 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7738    3.1982    1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4987    4.5090   -0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942    2.7227   -0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4768    3.6935    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1798    3.8899   -0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6687    1.9054    0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9088   -0.9373   -2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0984   -1.1667   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187   -2.2570   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -2.7368    2.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521   -3.9879    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7093    1.6334   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856    2.6275   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9167    1.3297   -0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7575   -0.8398    0.4520 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  7  3  1  0
 13  8  1  0
 22 17  1  0
 16  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 14 33  1  0
 14 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

  Mrv0541 09131211462D          

 23 26  0  0  0  0            999 V2000
    4.4714   -2.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7100   -2.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944   -1.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0884    1.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9654    2.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4434    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -1.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    1.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524    1.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.1363    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    0.8627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -1.4137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878   -0.5895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -0.9446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -1.6331    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  2  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19  9  1  0  0  0  0
 19 16  2  0  0  0  0
 20 10  2  0  0  0  0
 21 15  2  0  0  0  0
 21 20  1  0  0  0  0
 22 10  1  0  0  0  0
 22 15  1  0  0  0  0
 22 17  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041890

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=CC2=C(S1)N1C(C)=NN=C1CN=C2C1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C17H15ClN4S/c1-3-11-8-13-16(12-6-4-5-7-14(12)18)19-9-15-21-20-10(2)22(15)17(13)23-11/h4-8H,3,9H2,1-2H3

> <INCHI_KEY>
VMZUTJCNQWMAGF-UHFFFAOYSA-N

> <FORMULA>
C17H15ClN4S

> <MOLECULAR_WEIGHT>
342.846

> <EXACT_MASS>
342.070594897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.63885521134385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(2-chlorophenyl)-4-ethyl-13-methyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0²,⁶]trideca-2(6),4,7,10,12-pentaene

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.9847

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.276864416178967

> <JCHEM_PKA_STRONGEST_BASIC>
4.638754883722318

> <JCHEM_POLAR_SURFACE_AREA>
43.07

> <JCHEM_REFRACTIVITY>
104.725

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
etizolam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041890
     RDKit          3D
Etizolam
 38 41  0  0  0  0  0  0  0  0999 V2000
    3.2323    3.4881    0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7557    3.3423    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993    1.8925    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866    1.2783    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106   -0.0395    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877   -0.6723   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    0.5744   -0.0371 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -2.0812   -0.1954 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5336   -2.5509   -0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4977   -1.6579   -1.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618   -3.8804   -0.8641 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4208   -4.2004   -0.0666 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381   -3.1051    0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184   -2.9950    1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3007   -2.0343    0.8213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1654   -0.7915    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4104   -0.1704    0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5510    1.0598   -0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875    1.6329   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9186    0.9376   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8380   -0.3198    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5920   -0.8413    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5392   -2.4492    1.1462 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7738    3.1982    1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4987    4.5090   -0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942    2.7227   -0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4768    3.6935    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1798    3.8899   -0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6687    1.9054    0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9088   -0.9373   -2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0984   -1.1667   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187   -2.2570   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -2.7368    2.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521   -3.9879    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7093    1.6334   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856    2.6275   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9167    1.3297   -0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7575   -0.8398    0.4520 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  7  3  1  0
 13  8  1  0
 22 17  1  0
 16  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 14 33  1  0
 14 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
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       8.347  -5.122   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.192  -4.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.576  -3.599   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.498   2.300   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.269   3.823   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.294   1.340   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.835   4.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.441  -1.100   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.882   0.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.651  -3.048   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.372  -2.639   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.861   1.902   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.999  -0.559   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.631   3.425   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.539  -0.559   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.657   0.942   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.039  -1.763   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       5.198   3.988   0.000  0.00  0.00          Cl+0
HETATM   19  N   UNK     0       4.269   1.610   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       1.166  -2.639   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       1.097  -1.100   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       3.499  -1.763   0.000  0.00  0.00           N+0
HETATM   23  S   UNK     0       5.888  -3.048   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2   10                                                            
CONECT    3    1   11                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   14                                                       
CONECT    8   11   13                                                       
CONECT    9   15   19                                                       
CONECT   10    2   20   22                                                  
CONECT   11    3    8   23                                                  
CONECT   12    6   14   16                                                  
CONECT   13    8   16   17                                                  
CONECT   14    7   12   18                                                  
CONECT   15    9   21   22                                                  
CONECT   16   12   13   19                                                  
CONECT   17   13   22   23                                                  
CONECT   18   14                                                            
CONECT   19    9   16                                                       
CONECT   20   10   21                                                       
CONECT   21   15   20                                                       
CONECT   22   10   15   17                                                  
CONECT   23   11   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0041890
HETATM    1  C1  UNL     1       3.232   3.488   0.259  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.756   3.342   0.540  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.399   1.892   0.383  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.187   1.278   0.531  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.111  -0.039   0.333  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.288  -0.672  -0.001  1.00  0.00           C  
HETATM    7  S1  UNL     1       2.436   0.574  -0.037  1.00  0.00           S  
HETATM    8  N1  UNL     1       1.550  -2.081  -0.195  1.00  0.00           N  
HETATM    9  C7  UNL     1       2.534  -2.551  -0.937  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.498  -1.658  -1.672  1.00  0.00           C  
HETATM   11  N2  UNL     1       2.462  -3.880  -0.864  1.00  0.00           N  
HETATM   12  N3  UNL     1       1.421  -4.200  -0.067  1.00  0.00           N  
HETATM   13  C9  UNL     1       0.838  -3.105   0.362  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.318  -2.995   1.263  1.00  0.00           C  
HETATM   15  N4  UNL     1      -1.301  -2.034   0.821  1.00  0.00           N  
HETATM   16  C11 UNL     1      -1.165  -0.791   0.422  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.410  -0.170   0.058  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.551   1.060  -0.514  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.788   1.633  -0.748  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.919   0.938  -0.395  1.00  0.00           C  
HETATM   21  C16 UNL     1      -4.838  -0.320   0.188  1.00  0.00           C  
HETATM   22  C17 UNL     1      -3.592  -0.841   0.399  1.00  0.00           C  
HETATM   23 CL1  UNL     1      -3.539  -2.449   1.146  1.00  0.00          CL  
HETATM   24  H1  UNL     1       3.774   3.198   1.193  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.499   4.509  -0.063  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.494   2.723  -0.516  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.477   3.694   1.554  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.180   3.890  -0.238  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.669   1.905   0.864  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.909  -0.937  -2.275  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.098  -1.167  -0.875  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.119  -2.257  -2.358  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.049  -2.737   2.301  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.852  -3.988   1.325  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.709   1.633  -0.881  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.886   2.627  -1.208  1.00  0.00           H  
HETATM   37  H14 UNL     1      -5.917   1.330  -0.552  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.757  -0.840   0.452  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    4    7
CONECT    4    5   29
CONECT    5    6    6   16
CONECT    6    7    8
CONECT    8    9   13
CONECT    9   10   11   11
CONECT   10   30   31   32
CONECT   11   12
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   33   34
CONECT   15   16   16
CONECT   16   17
CONECT   17   18   18   22
CONECT   18   19   35
CONECT   19   20   20   36
CONECT   20   21   37
CONECT   21   22   22   38
CONECT   22   23
END

HMDB0041890
     RDKit          3D
Etizolam
 38 41  0  0  0  0  0  0  0  0999 V2000
    3.2323    3.4881    0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7557    3.3423    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993    1.8925    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866    1.2783    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106   -0.0395    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877   -0.6723   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    0.5744   -0.0371 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -2.0812   -0.1954 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5336   -2.5509   -0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4977   -1.6579   -1.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618   -3.8804   -0.8641 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4208   -4.2004   -0.0666 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381   -3.1051    0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184   -2.9950    1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3007   -2.0343    0.8213 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1654   -0.7915    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4104   -0.1704    0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5510    1.0598   -0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875    1.6329   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9186    0.9376   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8380   -0.3198    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5920   -0.8413    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5392   -2.4492    1.1462 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7738    3.1982    1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4987    4.5090   -0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942    2.7227   -0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4768    3.6935    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1798    3.8899   -0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6687    1.9054    0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9088   -0.9373   -2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0984   -1.1667   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187   -2.2570   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -2.7368    2.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521   -3.9879    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7093    1.6334   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856    2.6275   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9167    1.3297   -0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7575   -0.8398    0.4520 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  7  3  1  0
 13  8  1  0
 22 17  1  0
 16  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 14 33  1  0
 14 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sedekopan	Kegg
Etizolam fine granules	HMDB
Etizolam tablets	HMDB
Etizolam, 14C-labeled	HMDB

Chemical Formula

C₁₇H₁₅ClN₄S

Average Molecular Weight

342.846

Monoisotopic Molecular Weight

342.070594897

IUPAC Name

7-(2-chlorophenyl)-4-ethyl-13-methyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0²,⁶]trideca-2(6),4,7,10,12-pentaene

Traditional Name

etizolam

CAS Registry Number

40054-69-1

SMILES

CCC1=CC2=C(S1)N1C(C)=NN=C1CN=C2C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C17H15ClN4S/c1-3-11-8-13-16(12-6-4-5-7-14(12)18)19-9-15-21-20-10(2)22(15)17(13)23-11/h4-8H,3,9H2,1-2H3

InChI Key

VMZUTJCNQWMAGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienodiazepines. These are heteropolycyclic containing a thiophene ring fused to a diazepine ring. Thiophene is 5-membered ring consisting of four carbon and one sulfur atoms. Diazepine is a 7-membered ring consisting of five carbon and two nitrogen atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thienodiazepines

Sub Class

Not Available

Direct Parent

Thienodiazepines

Alternative Parents

Substituents

Thieno-para-diazepine
2,3,5-trisubstituted thiophene
Para-diazepine
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Azole
1,2,4-triazole
Thiophene
Ketimine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Imine
Organochloride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041890)

Source

Exogenous

Exogenous (HMDB: HMDB0041890)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	2.98	ALOGPS
logP	2.98	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	18.28	ChemAxon
pKa (Strongest Basic)	4.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.72 m³·mol⁻¹	ChemAxon
Polarizability	35.64 Å³	ChemAxon
Number of Rings	4	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]+	169.031	30932474
DeepCCS	[M-H]-	166.673	30932474
DeepCCS	[M-2H]-	200.532	30932474
DeepCCS	[M+Na]+	175.759	30932474
AllCCS	[M+H]+	176.8	32859911
AllCCS	[M+H-H2O]+	173.5	32859911
AllCCS	[M+NH4]+	179.8	32859911
AllCCS	[M+Na]+	180.7	32859911
AllCCS	[M-H]-	182.1	32859911
AllCCS	[M+Na-2H]-	181.6	32859911
AllCCS	[M+HCOO]-	181.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etizolam	CCC1=CC2=C(S1)N1C(C)=NN=C1CN=C2C1=CC=CC=C1Cl	3718.7	Standard polar	33892256
Etizolam	CCC1=CC2=C(S1)N1C(C)=NN=C1CN=C2C1=CC=CC=C1Cl	3041.9	Standard non polar	33892256
Etizolam	CCC1=CC2=C(S1)N1C(C)=NN=C1CN=C2C1=CC=CC=C1Cl	2969.5	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 - Etizolam GC-MS (Non-derivatized) - 70eV, Positive	splash10-06tf-8189000000-7a2ceb12ff7824adfa15	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etizolam 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 - Etizolam 10V, Positive-QTOF	splash10-0006-0039000000-6aa13f3ed55cdf58c0b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 20V, Positive-QTOF	splash10-0006-1119000000-93d7efb06b709134261b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 40V, Positive-QTOF	splash10-052p-6941000000-d4507f862b8b2305babe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 10V, Negative-QTOF	splash10-000f-0069000000-275219bc80bff427a3da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 20V, Negative-QTOF	splash10-001i-0192000000-c324182ddc3f89815336	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 40V, Negative-QTOF	splash10-03nm-0890000000-c508188c0bd16231d74d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 10V, Negative-QTOF	splash10-0006-0009000000-fa3ca2e1cd79c3734194	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 20V, Negative-QTOF	splash10-000x-4039000000-48e95c6351ad62de00cd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 40V, Negative-QTOF	splash10-001j-8293000000-65ab65f011e0fe3e3532	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 10V, Positive-QTOF	splash10-0006-0009000000-7a706823cbf79cb06f31	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 20V, Positive-QTOF	splash10-0006-0009000000-860d3e752f1da782d504	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etizolam 40V, Positive-QTOF	splash10-03fs-4698000000-1e803a56b7dcb176ceda	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

DB09166

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3191

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Etizolam

METLIN ID

Not Available

PubChem Compound

3307

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 Etizolam (HMDB0041890)

MOL for HMDB0041890 (Etizolam)

3D MOL for HMDB0041890 (Etizolam)

3D SDF for HMDB0041890 (Etizolam)

3D-SDF for HMDB0041890 (Etizolam)

PDB for HMDB0041890 (Etizolam)

3D PDB for HMDB0041890 (Etizolam)

SMILES for HMDB0041890 (Etizolam)

INCHI for HMDB0041890 (Etizolam)

Structure for HMDB0041890 (Etizolam)

3D Structure for HMDB0041890 (Etizolam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra