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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015533

Secondary Accession Numbers

HMDB15533

Metabolite Identification

Common Name

Cinolazepam

Description

Cinolazepam is only found in individuals that have used or taken this drug. It is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Cinolazepam is not approved for sale in the United States or Canada.Cinolazepam binds to central benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.

Structure

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

HMDB0015533
     RDKit          3D
Cinolazepam
 38 40  0  0  0  0  0  0  0  0999 V2000
    6.4983    1.2705   -0.6533 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591    0.6737   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3502   -0.0647    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1769    0.3621   -0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9395   -0.2398   -0.3695 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958   -1.5156   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372   -1.8633   -1.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -2.4433   -0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215   -3.5432   -1.2758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688   -1.7865   -0.5171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1348   -0.5962   -0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4999   -0.1950   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379   -1.2358   -0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6221   -1.0239   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1275    0.2576   -1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3288    1.2898   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262    1.0563   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    2.1492   -0.0128 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2789    0.2535    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780    0.9054    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3187    1.8109    2.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496    2.6171    3.7432 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0326    2.0427    2.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737    1.4073    1.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    0.5173    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6293   -1.1428   -0.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2503    0.0402    1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887    0.0555   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416    1.4742   -0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -2.7534    0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361   -3.3402   -2.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757   -2.2673   -0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2589   -1.8616   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1520    0.3991   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7538    2.3111   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0272    0.6260    1.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5118    2.7565    2.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    1.5966    1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  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  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25  5  1  0
 17 12  1  0
 25 19  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 20 36  1  0
 23 37  1  0
 24 38  1  0
M  END

1594
  Mrv0541 02231215352D          

 25 27  0  0  1  0            999 V2000
    4.6690   -2.3783    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7303   -1.4841    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.0034    2.3401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625    2.3401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3060    0.9518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1598    0.9518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.2908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4897    0.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2329   -0.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5018    1.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762    0.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8204    1.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6454    1.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7723   -0.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3104   -1.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6212   -0.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2586    1.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299   -1.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041   -1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4983   -1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3892   -0.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1433   -1.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0342   -0.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9113   -1.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543    2.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  0  0  0  0
  3 13  1  0  0  0  0
  4 12  2  0  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 12  1  0  0  0  0
  6 11  2  0  0  0  0
  6 13  1  0  0  0  0
  7 25  3  0  0  0  0
  8  9  2  0  0  0  0
  8 14  1  0  0  0  0
  9 11  1  0  0  0  0
  9 15  1  0  0  0  0
 10 17  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 25  1  0  0  0  0
 18 19  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015533

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1N=C(C2=CC=CC=C2F)C2=C(C=CC(Cl)=C2)N(CCC#N)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H13ClFN3O2/c19-11-6-7-15-13(10-11)16(12-4-1-2-5-14(12)20)22-17(24)18(25)23(15)9-3-8-21/h1-2,4-7,10,17,24H,3,9H2

> <INCHI_KEY>
XAXMYHMKTCNRRZ-UHFFFAOYSA-N

> <FORMULA>
C18H13ClFN3O2

> <MOLECULAR_WEIGHT>
357.766

> <EXACT_MASS>
357.068032587

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.11598730163477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[7-chloro-5-(2-fluorophenyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]propanenitrile

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.7029937280000005

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.67521311333259

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4871245413699277

> <JCHEM_POLAR_SURFACE_AREA>
76.69

> <JCHEM_REFRACTIVITY>
90.99000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinolazepam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015533
     RDKit          3D
Cinolazepam
 38 40  0  0  0  0  0  0  0  0999 V2000
    6.4983    1.2705   -0.6533 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591    0.6737   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3502   -0.0647    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1769    0.3621   -0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9395   -0.2398   -0.3695 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958   -1.5156   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372   -1.8633   -1.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -2.4433   -0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215   -3.5432   -1.2758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688   -1.7865   -0.5171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1348   -0.5962   -0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4999   -0.1950   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379   -1.2358   -0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6221   -1.0239   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1275    0.2576   -1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3288    1.2898   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262    1.0563   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    2.1492   -0.0128 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2789    0.2535    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780    0.9054    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3187    1.8109    2.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496    2.6171    3.7432 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0326    2.0427    2.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737    1.4073    1.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    0.5173    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6293   -1.1428   -0.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2503    0.0402    1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887    0.0555   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416    1.4742   -0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -2.7534    0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361   -3.3402   -2.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757   -2.2673   -0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2589   -1.8616   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1520    0.3991   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7538    2.3111   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0272    0.6260    1.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5118    2.7565    2.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    1.5966    1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  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  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25  5  1  0
 17 12  1  0
 25 19  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 20 36  1  0
 23 37  1  0
 24 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1594                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       8.715  -4.439   0.000  0.00  0.00          Cl+0
HETATM    2  F   UNK     0      10.697  -2.770   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0      11.206   4.368   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.330   4.368   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.038   1.777   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      11.498   1.777   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       3.080   4.276   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.381   0.275   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.768  -0.393   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.537   2.119   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.156   0.275   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.998   2.981   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.538   2.981   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.042  -0.608   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.913  -1.990   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.360  -0.685   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.083   3.591   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.149  -2.208   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.594  -2.904   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.130  -2.208   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.793  -0.122   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.334  -3.168   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.997  -1.082   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.768  -2.605   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.581   3.934   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   13                                                            
CONECT    4   12                                                            
CONECT    5    8   10   12                                                  
CONECT    6   11   13                                                       
CONECT    7   25                                                            
CONECT    8    5    9   14                                                  
CONECT    9    8   11   15                                                  
CONECT   10    5   17                                                       
CONECT   11    6    9   16                                                  
CONECT   12    4    5   13                                                  
CONECT   13    3    6   12                                                  
CONECT   14    8   18                                                       
CONECT   15    9   19                                                       
CONECT   16   11   20   21                                                  
CONECT   17   10   25                                                       
CONECT   18   14   19                                                       
CONECT   19    1   15   18                                                  
CONECT   20    2   16   22                                                  
CONECT   21   16   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
CONECT   25    7   17                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0015533
HETATM    1  N1  UNL     1       6.498   1.271  -0.653  1.00  0.00           N  
HETATM    2  C1  UNL     1       5.559   0.674  -0.310  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.350  -0.065   0.137  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.177   0.362  -0.715  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.939  -0.240  -0.370  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.596  -1.516  -0.933  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.237  -1.863  -1.913  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.541  -2.443  -0.436  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.521  -3.543  -1.276  1.00  0.00           O  
HETATM   10  N3  UNL     1      -0.769  -1.786  -0.517  1.00  0.00           N  
HETATM   11  C6  UNL     1      -1.135  -0.596  -0.095  1.00  0.00           C  
HETATM   12  C7  UNL     1      -2.500  -0.195  -0.320  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.338  -1.236  -0.761  1.00  0.00           C  
HETATM   14  C9  UNL     1      -4.622  -1.024  -1.143  1.00  0.00           C  
HETATM   15  C10 UNL     1      -5.127   0.258  -1.098  1.00  0.00           C  
HETATM   16  C11 UNL     1      -4.329   1.290  -0.674  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.026   1.056  -0.292  1.00  0.00           C  
HETATM   18  F1  UNL     1      -2.255   2.149  -0.013  1.00  0.00           F  
HETATM   19  C13 UNL     1      -0.279   0.254   0.696  1.00  0.00           C  
HETATM   20  C14 UNL     1      -0.978   0.905   1.690  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.319   1.811   2.498  1.00  0.00           C  
HETATM   22 CL1  UNL     1      -1.250   2.617   3.743  1.00  0.00          CL  
HETATM   23  C16 UNL     1       1.033   2.043   2.295  1.00  0.00           C  
HETATM   24  C17 UNL     1       1.774   1.407   1.315  1.00  0.00           C  
HETATM   25  C18 UNL     1       1.104   0.517   0.532  1.00  0.00           C  
HETATM   26  H1  UNL     1       4.629  -1.143  -0.125  1.00  0.00           H  
HETATM   27  H2  UNL     1       4.250   0.040   1.208  1.00  0.00           H  
HETATM   28  H3  UNL     1       3.489   0.055  -1.762  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.142   1.474  -0.674  1.00  0.00           H  
HETATM   30  H5  UNL     1       0.700  -2.753   0.595  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.236  -3.340  -2.188  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.976  -2.267  -0.810  1.00  0.00           H  
HETATM   33  H8  UNL     1      -5.259  -1.862  -1.486  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.152   0.399  -1.405  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.754   2.311  -0.646  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.027   0.626   1.823  1.00  0.00           H  
HETATM   37  H12 UNL     1       1.512   2.756   2.942  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.806   1.597   1.140  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   25
CONECT    6    7    7    8
CONECT    8    9   10   30
CONECT    9   31
CONECT   10   11   11
CONECT   11   12   19
CONECT   12   13   13   17
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16   34
CONECT   16   17   17   35
CONECT   17   18
CONECT   19   20   20   25
CONECT   20   21   36
CONECT   21   22   23   23
CONECT   23   24   37
CONECT   24   25   25   38
END

HMDB0015533
     RDKit          3D
Cinolazepam
 38 40  0  0  0  0  0  0  0  0999 V2000
    6.4983    1.2705   -0.6533 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591    0.6737   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3502   -0.0647    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1769    0.3621   -0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9395   -0.2398   -0.3695 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958   -1.5156   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372   -1.8633   -1.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -2.4433   -0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215   -3.5432   -1.2758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688   -1.7865   -0.5171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1348   -0.5962   -0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4999   -0.1950   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379   -1.2358   -0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6221   -1.0239   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1275    0.2576   -1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3288    1.2898   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262    1.0563   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    2.1492   -0.0128 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2789    0.2535    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780    0.9054    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3187    1.8109    2.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496    2.6171    3.7432 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0326    2.0427    2.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737    1.4073    1.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    0.5173    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6293   -1.1428   -0.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2503    0.0402    1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887    0.0555   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416    1.4742   -0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -2.7534    0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361   -3.3402   -2.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757   -2.2673   -0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2589   -1.8616   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1520    0.3991   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7538    2.3111   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0272    0.6260    1.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5118    2.7565    2.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    1.5966    1.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  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  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25  5  1  0
 17 12  1  0
 25 19  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 20 36  1  0
 23 37  1  0
 24 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2-Cyanoethyl)-7-chloro-3-hydroxy-5-(2'-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one	ChEBI
7-Chloro-5-(2-fluorophenyl)-2,3-dihydro-3-hydroxy-2-oxo-1H-1,4-benzodiazepine-1-propanenitrile	ChEBI
7-Chloro-5-(O-fluorophenyl)-2,3-dihydro-3-hydroxy-2-oxo-1H-1,4-benzodiazepine-1-propionitrile	ChEBI
Cinolazepamum	ChEBI
Gerodorm	Kegg
7-Chloro-5-(2-fluorophenyl)-2,3-dihydro-3-hydroxy-2-oxo-1H-1,4-benzodiazepine-1-propionitrile	HMDB

Chemical Formula

C₁₈H₁₃ClFN₃O₂

Average Molecular Weight

357.766

Monoisotopic Molecular Weight

357.068032587

IUPAC Name

3-[7-chloro-5-(2-fluorophenyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]propanenitrile

Traditional Name

cinolazepam

CAS Registry Number

75696-02-5

SMILES

OC1N=C(C2=CC=CC=C2F)C2=C(C=CC(Cl)=C2)N(CCC#N)C1=O

InChI Identifier

InChI=1S/C18H13ClFN3O2/c19-11-6-7-15-13(10-11)16(12-4-1-2-5-14(12)20)22-17(24)18(25)23(15)9-3-8-21/h1-2,4-7,10,17,24H,3,9H2

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:59514 )
1,4-benzodiazepinone (CHEBI:59514 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015533)

Source

Exogenous

Exogenous (HMDB: HMDB0015533)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0015533)
Sedative (HMDB: HMDB0015533)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.012 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	2.42	ALOGPS
logP	2.7	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	10.68	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.99 m³·mol⁻¹	ChemAxon
Polarizability	34.12 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]+	171.5	30932474
DeepCCS	[M-H]-	169.142	30932474
DeepCCS	[M-2H]-	203.009	30932474
DeepCCS	[M+Na]+	178.236	30932474
AllCCS	[M+H]+	179.3	32859911
AllCCS	[M+H-H2O]+	176.2	32859911
AllCCS	[M+NH4]+	182.1	32859911
AllCCS	[M+Na]+	182.9	32859911
AllCCS	[M-H]-	179.5	32859911
AllCCS	[M+Na-2H]-	178.9	32859911
AllCCS	[M+HCOO]-	178.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cinolazepam	OC1N=C(C2=CC=CC=C2F)C2=C(C=CC(Cl)=C2)N(CCC#N)C1=O	4035.0	Standard polar	33892256
Cinolazepam	OC1N=C(C2=CC=CC=C2F)C2=C(C=CC(Cl)=C2)N(CCC#N)C1=O	2809.0	Standard non polar	33892256
Cinolazepam	OC1N=C(C2=CC=CC=C2F)C2=C(C=CC(Cl)=C2)N(CCC#N)C1=O	2909.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cinolazepam,1TMS,isomer #1	C[Si](C)(C)OC1N=C(C2=CC=CC=C2F)C2=CC(Cl)=CC=C2N(CCC#N)C1=O	2827.4	Semi standard non polar	33892256
Cinolazepam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1N=C(C2=CC=CC=C2F)C2=CC(Cl)=CC=C2N(CCC#N)C1=O	2964.0	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 - Cinolazepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-0iki-0397000000-6dc71c0e52cf323c4249	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinolazepam GC-MS (1 TMS) - 70eV, Positive	splash10-0ir9-8139300000-76aa398fb739bbfd5ec5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinolazepam 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 - Cinolazepam 10V, Positive-QTOF	splash10-0a4i-1019000000-3fb8d424ad020ac2a56e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 20V, Positive-QTOF	splash10-0006-2019000000-7cfb2f9949767ef2eaf4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 40V, Positive-QTOF	splash10-0udi-9110000000-981eb27764717ef665cd	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 10V, Negative-QTOF	splash10-0a4i-0009000000-2d5c6a3df2ed9be23c27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 20V, Negative-QTOF	splash10-0k92-0179000000-d07cdeed3541a874c6b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 40V, Negative-QTOF	splash10-00dl-8191000000-920c5d9c75b7fbb9e1f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 10V, Positive-QTOF	splash10-0a4i-0009000000-532779292ef45c60c552	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 20V, Positive-QTOF	splash10-014i-0019000000-4ca765842e6fa443fb96	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 40V, Positive-QTOF	splash10-022a-2393000000-4500af5fdcda7e1dd844	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 10V, Negative-QTOF	splash10-000i-0039000000-d8eed653aed565268b41	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 20V, Negative-QTOF	splash10-001i-0092000000-a0cfcfb5f9e44566fb74	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinolazepam 40V, Negative-QTOF	splash10-001l-9050000000-da82cc62103d64b77f16	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01594	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01594	21059682	details

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

DB01594

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2298251

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cinolazepam

METLIN ID

Not Available

PubChem Compound

3033621

PDB ID

Not Available

ChEBI ID

59514

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

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Gamma-aminobutyric acid receptor subunit gamma-2

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRG2
Uniprot ID:: P18507
Molecular weight:: 54161.8

References

Enzyme Details

2. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

References

Enzyme Details

3. Gamma-aminobutyric acid receptor subunit alpha-2

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA2
Uniprot ID:: P47869
Molecular weight:: 51325.9

References

Enzyme Details

4. Gamma-aminobutyric acid receptor subunit alpha-3

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA3
Uniprot ID:: P34903
Molecular weight:: 55164.1

References

Enzyme Details

5. Gamma-aminobutyric acid receptor subunit alpha-5

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA5
Uniprot ID:: P31644
Molecular weight:: 52145.6

References

Enzyme Details

6. Gamma-aminobutyric acid receptor subunit beta-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRB1
Uniprot ID:: P18505
Molecular weight:: 54234.1

References

Enzyme Details

7. Gamma-aminobutyric acid receptor subunit beta-2

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRB2
Uniprot ID:: P47870
Molecular weight:: 59149.9

References

Enzyme Details

8. Gamma-aminobutyric acid receptor subunit beta-3

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRB3
Uniprot ID:: P28472
Molecular weight:: 54115.0

References

Enzyme Details

9. Gamma-aminobutyric acid receptor subunit delta

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRD
Uniprot ID:: O14764
Molecular weight:: 50707.8

References

Enzyme Details

10. Gamma-aminobutyric acid receptor subunit epsilon

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRE
Uniprot ID:: P78334
Molecular weight:: 57971.2

References

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Showing metabocard for Cinolazepam (HMDB0015533)

MOL for HMDB0015533 (Cinolazepam)

3D MOL for HMDB0015533 (Cinolazepam)

3D SDF for HMDB0015533 (Cinolazepam)

3D-SDF for HMDB0015533 (Cinolazepam)

PDB for HMDB0015533 (Cinolazepam)

3D PDB for HMDB0015533 (Cinolazepam)

SMILES for HMDB0015533 (Cinolazepam)

INCHI for HMDB0015533 (Cinolazepam)

Structure for HMDB0015533 (Cinolazepam)

3D Structure for HMDB0015533 (Cinolazepam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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