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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:10:06 UTC

Update Date

2019-07-23 07:15:29 UTC

HMDB ID

HMDB0060969

Secondary Accession Numbers

HMDB60969

Metabolite Identification

Common Name

desmethyladinazolam

Description

desmethyladinazolam belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring. desmethyladinazolam is a very strong basic compound (based on its pKa). desmethyladinazolam is a metabolite of adinazolam. Adinazolam (marketed under the brand name Deracyn) is a benzodiazepine derivative. Adinazolam was developed by Dr. Jackson B. Hester, who was seeking to enhance the antidepressant properties of alprazolam, which he also developed. It possesses anxiolytic, anticonvulsant, sedative, and antidepressant properties.

Structure

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

HMDB0060969
     RDKit          3D
desmethyladinazolam
 37 40  0  0  0  0  0  0  0  0999 V2000
   -4.1862    0.8924   -2.2575 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681   -0.0104   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0981    0.8992   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466    2.1823    0.1296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5348    2.7006    0.9710 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951    1.7839    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9777    0.6990    0.4744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2794   -0.5505    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1085   -1.6282    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848   -2.8812    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970   -2.9775    0.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623   -4.5421    0.4590 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7229   -1.8749    0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -0.6402    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911    0.4281    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756    0.3148   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3496    1.2847    0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5702    1.3372   -0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758    0.4193   -1.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9310   -0.5240   -1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7103   -0.5803   -0.9859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432    1.5235    1.2857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3528    1.9059    2.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4359    1.5740   -2.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103    0.3392   -3.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033   -0.6933   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7377   -0.4090   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -1.5170    0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1352   -3.7310    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -1.9217    0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109    2.0132    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3072    2.0872   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8408    0.4829   -1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2023   -1.2451   -2.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -1.3379   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4049    1.2252    2.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    2.9716    2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  2  0
 22 23  1  0
  7  3  1  0
 14  8  1  0
 21 16  1  0
 23  6  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  0
 23 37  1  0
M  END


  Mrv0541 07091309102D          

 23 26  0  0  0  0            999 V2000
    4.8445    2.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654    2.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9992    1.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4409    1.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3748    0.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -1.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0283   -1.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0060   -0.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7654   -2.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4857    0.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5956    1.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3371   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1860   -0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6972   -0.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4456   -1.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3337   -0.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9712    0.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -1.1582    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5839   -2.4868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2145    0.9047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -1.4348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5732   -0.6127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728   -0.9173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 19  9  1  0  0  0  0
 20 10  1  0  0  0  0
 20 17  2  0  0  0  0
 21 15  2  0  0  0  0
 22 16  2  0  0  0  0
 22 21  1  0  0  0  0
 23 14  1  0  0  0  0
 23 15  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060969

> <DATABASE_NAME>
hmdb

> <SMILES>
NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12

> <INCHI_IDENTIFIER>
InChI=1S/C17H14ClN5/c18-12-6-7-14-13(8-12)17(11-4-2-1-3-5-11)20-10-16-22-21-15(9-19)23(14)16/h1-8H,9-10,19H2

> <INCHI_KEY>
IITNCTOGXYNNRY-UHFFFAOYSA-N

> <FORMULA>
C17H14ClN5

> <MOLECULAR_WEIGHT>
323.78

> <EXACT_MASS>
323.09377318

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.42492810762374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methanamine

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
1.471

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.384295667135547

> <JCHEM_PKA_STRONGEST_BASIC>
7.865815181695542

> <JCHEM_POLAR_SURFACE_AREA>
69.09

> <JCHEM_REFRACTIVITY>
102.2387

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methanamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060969
     RDKit          3D
desmethyladinazolam
 37 40  0  0  0  0  0  0  0  0999 V2000
   -4.1862    0.8924   -2.2575 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681   -0.0104   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0981    0.8992   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466    2.1823    0.1296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5348    2.7006    0.9710 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951    1.7839    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9777    0.6990    0.4744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2794   -0.5505    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1085   -1.6282    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848   -2.8812    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970   -2.9775    0.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623   -4.5421    0.4590 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7229   -1.8749    0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -0.6402    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911    0.4281    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756    0.3148   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3496    1.2847    0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5702    1.3372   -0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758    0.4193   -1.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9310   -0.5240   -1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7103   -0.5803   -0.9859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432    1.5235    1.2857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3528    1.9059    2.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4359    1.5740   -2.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103    0.3392   -3.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033   -0.6933   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7377   -0.4090   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -1.5170    0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1352   -3.7310    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -1.9217    0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109    2.0132    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3072    2.0872   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8408    0.4829   -1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2023   -1.2451   -2.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -1.3379   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4049    1.2252    2.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    2.9716    2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  2  0
 22 23  1  0
  7  3  1  0
 14  8  1  0
 21 16  1  0
 23  6  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  0
 23 37  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       9.043   4.095   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.589   4.601   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.332   2.582   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.423   3.594   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.166   1.575   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.183  -3.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.653  -3.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.478  -0.581   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.295  -4.449   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.773   0.967   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.712   2.082   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.096  -1.992   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.947  -0.412   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.035  -1.652   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.698  -3.030   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.490  -0.547   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.546   1.075   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       9.627  -2.162   0.000  0.00  0.00          Cl+0
HETATM   19  N   UNK     0       4.823  -4.642   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       4.134   1.689   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       1.199  -2.678   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       1.070  -1.144   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       3.496  -1.712   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   14                                                       
CONECT    8   12   13                                                       
CONECT    9   15   19                                                       
CONECT   10   16   20                                                       
CONECT   11    4    5   17                                                  
CONECT   12    6    8   18                                                  
CONECT   13    8   14   17                                                  
CONECT   14    7   13   23                                                  
CONECT   15    9   21   23                                                  
CONECT   16   10   22   23                                                  
CONECT   17   11   13   20                                                  
CONECT   18   12                                                            
CONECT   19    9                                                            
CONECT   20   10   17                                                       
CONECT   21   15   22                                                       
CONECT   22   16   21                                                       
CONECT   23   14   15   16                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0060969
HETATM    1  N1  UNL     1      -4.186   0.892  -2.257  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.768  -0.010  -1.137  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.098   0.899  -0.197  1.00  0.00           C  
HETATM    4  N2  UNL     1      -3.447   2.182   0.130  1.00  0.00           N  
HETATM    5  N3  UNL     1      -2.535   2.701   0.971  1.00  0.00           N  
HETATM    6  C3  UNL     1      -1.595   1.784   1.203  1.00  0.00           C  
HETATM    7  N4  UNL     1      -1.978   0.699   0.474  1.00  0.00           N  
HETATM    8  C4  UNL     1      -1.279  -0.550   0.437  1.00  0.00           C  
HETATM    9  C5  UNL     1      -2.108  -1.628   0.371  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.485  -2.881   0.379  1.00  0.00           C  
HETATM   11  C7  UNL     1      -0.097  -2.977   0.456  1.00  0.00           C  
HETATM   12 CL1  UNL     1       0.662  -4.542   0.459  1.00  0.00          CL  
HETATM   13  C8  UNL     1       0.723  -1.875   0.527  1.00  0.00           C  
HETATM   14  C9  UNL     1       0.111  -0.640   0.513  1.00  0.00           C  
HETATM   15  C10 UNL     1       1.091   0.428   0.598  1.00  0.00           C  
HETATM   16  C11 UNL     1       2.376   0.315  -0.016  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.350   1.285   0.292  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.570   1.337  -0.337  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.876   0.419  -1.307  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.931  -0.524  -1.610  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.710  -0.580  -0.986  1.00  0.00           C  
HETATM   22  N5  UNL     1       0.843   1.523   1.286  1.00  0.00           N  
HETATM   23  C17 UNL     1      -0.353   1.906   2.048  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.436   1.574  -2.460  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.410   0.339  -3.096  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.103  -0.693  -1.704  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.738  -0.409  -0.836  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.160  -1.517   0.376  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.135  -3.731   0.322  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.800  -1.922   0.650  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.111   2.013   1.060  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.307   2.087  -0.089  1.00  0.00           H  
HETATM   33  H10 UNL     1       5.841   0.483  -1.783  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.202  -1.245  -2.389  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.040  -1.338  -1.365  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.405   1.225   2.913  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.227   2.972   2.309  1.00  0.00           H  
CONECT    1    2   24   25
CONECT    2    3   26   27
CONECT    3    4    4    7
CONECT    4    5
CONECT    5    6    6
CONECT    6    7   23
CONECT    7    8
CONECT    8    9    9   14
CONECT    9   10   28
CONECT   10   11   11   29
CONECT   11   12   13
CONECT   13   14   14   30
CONECT   14   15
CONECT   15   16   22   22
CONECT   16   17   17   21
CONECT   17   18   31
CONECT   18   19   19   32
CONECT   19   20   33
CONECT   20   21   21   34
CONECT   21   35
CONECT   22   23
CONECT   23   36   37
END

HMDB0060969
     RDKit          3D
desmethyladinazolam
 37 40  0  0  0  0  0  0  0  0999 V2000
   -4.1862    0.8924   -2.2575 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681   -0.0104   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0981    0.8992   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466    2.1823    0.1296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5348    2.7006    0.9710 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951    1.7839    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9777    0.6990    0.4744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2794   -0.5505    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1085   -1.6282    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848   -2.8812    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970   -2.9775    0.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623   -4.5421    0.4590 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7229   -1.8749    0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -0.6402    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0911    0.4281    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756    0.3148   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3496    1.2847    0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5702    1.3372   -0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758    0.4193   -1.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9310   -0.5240   -1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7103   -0.5803   -0.9859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432    1.5235    1.2857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3528    1.9059    2.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4359    1.5740   -2.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103    0.3392   -3.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033   -0.6933   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7377   -0.4090   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -1.5170    0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1352   -3.7310    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -1.9217    0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109    2.0132    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3072    2.0872   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8408    0.4829   -1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2023   -1.2451   -2.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -1.3379   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4049    1.2252    2.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    2.9716    2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  2  0
 22 23  1  0
  7  3  1  0
 14  8  1  0
 21 16  1  0
 23  6  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  0
 23 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄ClN₅

Average Molecular Weight

323.78

Monoisotopic Molecular Weight

323.09377318

IUPAC Name

{12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methanamine

Traditional Name

{12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methanamine

CAS Registry Number

Not Available

SMILES

NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12

InChI Identifier

InChI=1S/C17H14ClN5/c18-12-6-7-14-13(8-12)17(11-4-2-1-3-5-11)20-10-16-22-21-15(9-19)23(14)16/h1-8H,9-10,19H2

InChI Key

IITNCTOGXYNNRY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,2,4-triazolo[4,3-a][1,4]benzodiazepines

Alternative Parents

Substituents

1,2,4-triazolo[4,3-a][1,4]benzodiazepine
Aralkylamine
Aryl chloride
Aryl halide
Benzenoid
Monocyclic benzene moiety
Azole
Heteroaromatic compound
1,2,4-triazole
Ketimine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amine
Organochloride
Organohalogen compound
Primary aliphatic amine
Organonitrogen compound
Imine
Primary amine
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060969)
Liver (HMDB: HMDB0060969)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060969)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060969)

Cellular substructure

Cytoplasm (HMDB: HMDB0060969)

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	0.072 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.47	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	18.38	ChemAxon
pKa (Strongest Basic)	7.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.24 m³·mol⁻¹	ChemAxon
Polarizability	33.42 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-2H]-	205.855	30932474
DeepCCS	[M+Na]+	181.081	30932474
AllCCS	[M+H]+	174.7	32859911
AllCCS	[M+H-H2O]+	171.3	32859911
AllCCS	[M+NH4]+	177.8	32859911
AllCCS	[M+Na]+	178.7	32859911
AllCCS	[M-H]-	177.1	32859911
AllCCS	[M+Na-2H]-	176.3	32859911
AllCCS	[M+HCOO]-	175.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
desmethyladinazolam	NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12	4213.2	Standard polar	33892256
desmethyladinazolam	NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12	3072.0	Standard non polar	33892256
desmethyladinazolam	NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12	3092.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
desmethyladinazolam,1TMS,isomer #1	C[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21	3193.7	Semi standard non polar	33892256
desmethyladinazolam,1TMS,isomer #1	C[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21	3071.9	Standard non polar	33892256
desmethyladinazolam,1TMS,isomer #1	C[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21	4506.7	Standard polar	33892256
desmethyladinazolam,2TMS,isomer #1	C[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C	3194.6	Semi standard non polar	33892256
desmethyladinazolam,2TMS,isomer #1	C[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C	3285.9	Standard non polar	33892256
desmethyladinazolam,2TMS,isomer #1	C[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C	4298.5	Standard polar	33892256
desmethyladinazolam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21	3356.3	Semi standard non polar	33892256
desmethyladinazolam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21	3312.9	Standard non polar	33892256
desmethyladinazolam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21	4558.4	Standard polar	33892256
desmethyladinazolam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C(C)(C)C	3541.1	Semi standard non polar	33892256
desmethyladinazolam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C(C)(C)C	3740.6	Standard non polar	33892256
desmethyladinazolam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C(C)(C)C	4340.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - desmethyladinazolam GC-MS (Non-derivatized) - 70eV, Positive	splash10-053v-6092000000-6eecf8822b2572c1b12c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - desmethyladinazolam 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 - desmethyladinazolam 10V, Positive-QTOF	splash10-00di-0009000000-383cca510ff73d94aece	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 20V, Positive-QTOF	splash10-05fr-0019000000-ac89e8cd06fcf4dca729	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 40V, Positive-QTOF	splash10-0i00-5491000000-92f0352d7a746554fd1d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 10V, Negative-QTOF	splash10-00di-0039000000-3a5e88caae0c6b1364f8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 20V, Negative-QTOF	splash10-00di-0069000000-e065989320309b0956d2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 40V, Negative-QTOF	splash10-0udi-5291000000-134c23efc70b9e9534d0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 10V, Negative-QTOF	splash10-00di-0009000000-240e75f736e0def15d64	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 20V, Negative-QTOF	splash10-00di-1029000000-115ac79998dbe2a94e20	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 40V, Negative-QTOF	splash10-0kai-5095000000-4ea2f9c74da54774cf00	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 10V, Positive-QTOF	splash10-00di-0009000000-43ea0644a7793b861ac2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 20V, Positive-QTOF	splash10-00di-0009000000-202c5e39f130150291e3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethyladinazolam 40V, Positive-QTOF	splash10-0pxu-4491000000-d374db1e9979915019db	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12611937

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 desmethyladinazolam (HMDB0060969)

MOL for HMDB0060969 (desmethyladinazolam)

3D MOL for HMDB0060969 (desmethyladinazolam)

3D SDF for HMDB0060969 (desmethyladinazolam)

3D-SDF for HMDB0060969 (desmethyladinazolam)

PDB for HMDB0060969 (desmethyladinazolam)

3D PDB for HMDB0060969 (desmethyladinazolam)

SMILES for HMDB0060969 (desmethyladinazolam)

INCHI for HMDB0060969 (desmethyladinazolam)

Structure for HMDB0060969 (desmethyladinazolam)

3D Structure for HMDB0060969 (desmethyladinazolam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra