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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:17:35 UTC

Update Date

2019-07-23 07:15:44 UTC

HMDB ID

HMDB0061089

Secondary Accession Numbers

HMDB61089

Metabolite Identification

Common Name

Alpha-hydroxymidazolam

Description

Alpha-hydroxymidazolam is a metabolite of midazolam. Midazolam, marketed in English-speaking countries under the trade names Dormicum, Hypnovel, and Versed, is a short-acting drug in the benzodiazepine class developed by Hoffmann-La Roche in the 1970s. The drug is used for treatment of acute seizures, moderate to severe insomnia, and for inducing sedation and amnesia before medical procedures. It possesses profoundly potent anxiolytic, amnestic, hypnotic, anticonvulsant, skeletal muscle relaxant, and sedative properties. (Wikipedia)

Structure

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

HMDB0061089
     RDKit          3D
Alpha-hydroxymidazolam
 37 40  0  0  0  0  0  0  0  0999 V2000
    4.4314    0.0408   -1.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299    0.1822   -0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -0.9990   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2800   -2.2767   -0.8231 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -3.0592   -0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905   -2.3007    0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603   -1.0553    0.1651 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487    0.0802    0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352    0.8559    1.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840    1.9422    2.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2021    2.1698    2.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    3.5295    3.0001 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    1.3689    1.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308    0.3040    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -0.4655    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3257    0.1699   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3990   -0.6791   -0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229   -0.2762   -1.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6166    1.0523   -1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978    1.9233   -1.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795    1.4671   -0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4537    2.3672   -0.6970 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045   -1.7780    0.0347 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0805   -2.6902    0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9613    0.8420   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542    0.1903    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007    1.1509   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1375   -4.0956   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1653    0.6081    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2701    2.5660    2.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7506    1.5125    1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434   -1.7445   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3389   -0.9817   -1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5178    1.3936   -2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877    2.9953   -1.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909   -2.5969    1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3010   -3.7137    0.2275 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
 21 22  1  0
 15 23  2  0
 23 24  1  0
  7  3  1  0
 14  8  1  0
 21 16  1  0
 24  6  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  5 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 24 36  1  0
 24 37  1  0
M  END


  Mrv0541 07091309172D          

 24 27  0  0  0  0            999 V2000
    4.9992    1.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8445    2.1935    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
    4.0654    2.4647    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
    0.5732   -0.6127    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
    1.7654   -2.3835    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
    1.3337   -0.2928    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
    3.1860   -0.2205    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
    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
    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
    2.6618    2.1968    0.0000 F   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
    2.2145    0.9047    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
    2.5839   -2.4868    0.0000 O   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
  6  5  2  0  0  0  0
 11  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  3  2  0  0  0  0
 14  7  1  0  0  0  0
 15  4  2  0  0  0  0
 15 13  1  0  0  0  0
 16  6  1  0  0  0  0
 16 14  2  0  0  0  0
 17 10  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 11  1  0  0  0  0
 20 15  1  0  0  0  0
 21  8  1  0  0  0  0
 21 17  2  0  0  0  0
 22  9  1  0  0  0  0
 22 18  2  0  0  0  0
 23 12  1  0  0  0  0
 23 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061089

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12

> <INCHI_IDENTIFIER>
InChI=1S/C18H13ClFN3O/c19-11-5-6-16-14(7-11)18(13-3-1-2-4-15(13)20)22-9-12-8-21-17(10-24)23(12)16/h1-8,24H,9-10H2

> <INCHI_KEY>
QHSMEGADRFZVNE-UHFFFAOYSA-N

> <FORMULA>
C18H13ClFN3O

> <MOLECULAR_WEIGHT>
341.767

> <EXACT_MASS>
341.073117965

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.74198386694288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[12-chloro-9-(2-fluorophenyl)-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl]methanol

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.4792000000000005

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.948224666478492

> <JCHEM_PKA_STRONGEST_BASIC>
4.991109360957721

> <JCHEM_POLAR_SURFACE_AREA>
50.41

> <JCHEM_REFRACTIVITY>
101.1319

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[12-chloro-9-(2-fluorophenyl)-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl]methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061089
     RDKit          3D
Alpha-hydroxymidazolam
 37 40  0  0  0  0  0  0  0  0999 V2000
    4.4314    0.0408   -1.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299    0.1822   -0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -0.9990   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2800   -2.2767   -0.8231 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -3.0592   -0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905   -2.3007    0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603   -1.0553    0.1651 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487    0.0802    0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352    0.8559    1.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840    1.9422    2.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2021    2.1698    2.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    3.5295    3.0001 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    1.3689    1.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308    0.3040    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -0.4655    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3257    0.1699   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3990   -0.6791   -0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229   -0.2762   -1.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6166    1.0523   -1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978    1.9233   -1.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795    1.4671   -0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4537    2.3672   -0.6970 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045   -1.7780    0.0347 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0805   -2.6902    0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9613    0.8420   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542    0.1903    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007    1.1509   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1375   -4.0956   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1653    0.6081    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2701    2.5660    2.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7506    1.5125    1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434   -1.7445   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3389   -0.9817   -1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5178    1.3936   -2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877    2.9953   -1.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909   -2.5969    1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3010   -3.7137    0.2275 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
 21 22  1  0
 15 23  2  0
 23 24  1  0
  7  3  1  0
 14  8  1  0
 21 16  1  0
 24  6  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  5 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 24 36  1  0
 24 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       9.332   2.582   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.043   4.095   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.166   1.575   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.589   4.601   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.183  -3.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.653  -3.063   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.478  -0.581   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.070  -1.144   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.773   0.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.295  -4.449   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.096  -1.992   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.490  -0.547   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.712   2.082   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.947  -0.412   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.423   3.594   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.035  -1.652   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.698  -3.030   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.546   1.075   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       9.627  -2.162   0.000  0.00  0.00          Cl+0
HETATM   20  F   UNK     0       4.969   4.101   0.000  0.00  0.00           F+0
HETATM   21  N   UNK     0       1.199  -2.678   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       4.134   1.689   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
HETATM   24  O   UNK     0       4.823  -4.642   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   13                                                       
CONECT    4    2   15                                                       
CONECT    5    6   11                                                       
CONECT    6    5   16                                                       
CONECT    7   11   14                                                       
CONECT    8   12   21                                                       
CONECT    9   12   22                                                       
CONECT   10   17   24                                                       
CONECT   11    5    7   19                                                  
CONECT   12    8    9   23                                                  
CONECT   13    3   15   18                                                  
CONECT   14    7   16   18                                                  
CONECT   15    4   13   20                                                  
CONECT   16    6   14   23                                                  
CONECT   17   10   21   23                                                  
CONECT   18   13   14   22                                                  
CONECT   19   11                                                            
CONECT   20   15                                                            
CONECT   21    8   17                                                       
CONECT   22    9   18                                                       
CONECT   23   12   16   17                                                  
CONECT   24   10                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0061089
HETATM    1  O1  UNL     1       4.431   0.041  -1.868  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.930   0.182  -0.525  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.060  -0.999  -0.372  1.00  0.00           C  
HETATM    4  N1  UNL     1       3.280  -2.277  -0.823  1.00  0.00           N  
HETATM    5  C3  UNL     1       2.224  -3.059  -0.554  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.290  -2.301   0.081  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.860  -1.055   0.165  1.00  0.00           N  
HETATM    8  C5  UNL     1       1.249   0.080   0.795  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.135   0.856   1.472  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.584   1.942   2.165  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.202   2.170   2.135  1.00  0.00           C  
HETATM   12 CL1  UNL     1      -0.458   3.530   3.000  1.00  0.00          CL  
HETATM   13  C9  UNL     1      -0.675   1.369   1.446  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.131   0.304   0.760  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.161  -0.466   0.097  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.326   0.170  -0.457  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.399  -0.679  -0.797  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.523  -0.276  -1.442  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.617   1.052  -1.786  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.598   1.923  -1.481  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.479   1.467  -0.830  1.00  0.00           C  
HETATM   22  F1  UNL     1      -1.454   2.367  -0.697  1.00  0.00           F  
HETATM   23  N3  UNL     1      -1.104  -1.778   0.035  1.00  0.00           N  
HETATM   24  C18 UNL     1      -0.080  -2.690   0.561  1.00  0.00           C  
HETATM   25  H1  UNL     1       4.961   0.842  -2.098  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.854   0.190   0.046  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.401   1.151  -0.641  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.137  -4.096  -0.799  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.165   0.608   1.516  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.270   2.566   2.700  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.751   1.512   1.471  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.343  -1.744  -0.531  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.339  -0.982  -1.686  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.518   1.394  -2.304  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.688   2.995  -1.765  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.091  -2.597   1.648  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.301  -3.714   0.227  1.00  0.00           H  
CONECT    1    2   25
CONECT    2    3   26   27
CONECT    3    4    4    7
CONECT    4    5
CONECT    5    6    6   28
CONECT    6    7   24
CONECT    7    8
CONECT    8    9    9   14
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12   13
CONECT   13   14   14   31
CONECT   14   15
CONECT   15   16   23   23
CONECT   16   17   17   21
CONECT   17   18   32
CONECT   18   19   19   33
CONECT   19   20   34
CONECT   20   21   21   35
CONECT   21   22
CONECT   23   24
CONECT   24   36   37
END

HMDB0061089
     RDKit          3D
Alpha-hydroxymidazolam
 37 40  0  0  0  0  0  0  0  0999 V2000
    4.4314    0.0408   -1.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299    0.1822   -0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -0.9990   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2800   -2.2767   -0.8231 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -3.0592   -0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905   -2.3007    0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603   -1.0553    0.1651 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487    0.0802    0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352    0.8559    1.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840    1.9422    2.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2021    2.1698    2.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    3.5295    3.0001 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    1.3689    1.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308    0.3040    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -0.4655    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3257    0.1699   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3990   -0.6791   -0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229   -0.2762   -1.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6166    1.0523   -1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978    1.9233   -1.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795    1.4671   -0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4537    2.3672   -0.6970 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045   -1.7780    0.0347 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0805   -2.6902    0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9613    0.8420   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542    0.1903    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007    1.1509   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1375   -4.0956   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1653    0.6081    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2701    2.5660    2.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7506    1.5125    1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434   -1.7445   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3389   -0.9817   -1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5178    1.3936   -2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6877    2.9953   -1.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909   -2.5969    1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3010   -3.7137    0.2275 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
 21 22  1  0
 15 23  2  0
 23 24  1  0
  7  3  1  0
 14  8  1  0
 21 16  1  0
 24  6  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  5 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 24 36  1  0
 24 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Hydroxymidazolam	Generator
Α-hydroxymidazolam	Generator
1-Hydroxymethylmidazolam	HMDB
1-OH-MDZ	HMDB
1-Hydroxymidazolam	HMDB
alpha-Hydroxymidazolam	MeSH

Chemical Formula

C₁₈H₁₃ClFN₃O

Average Molecular Weight

341.767

Monoisotopic Molecular Weight

341.073117965

IUPAC Name

[12-chloro-9-(2-fluorophenyl)-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl]methanol

Traditional Name

[12-chloro-9-(2-fluorophenyl)-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl]methanol

CAS Registry Number

Not Available

SMILES

OCC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12

InChI Identifier

InChI=1S/C18H13ClFN3O/c19-11-5-6-16-14(7-11)18(13-3-1-2-4-15(13)20)22-9-12-8-21-17(10-24)23(12)16/h1-8,24H,9-10H2

InChI Key

QHSMEGADRFZVNE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazo[1,5-a][1,4]benzodiazepines. Imidazo[1,5-a][1,4]benzodiazepines are compounds containing an imidazole ring and a 1,4-benzodiazepine ring system, both sharing one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

Imidazo[1,5-a][1,4]benzodiazepines

Alternative Parents

Substituents

Imidazo[1,5-a][1,4]benzodiazepine
Para-diazepine
Fluorobenzene
Halobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
N-substituted imidazole
Heteroaromatic compound
Azole
Imidazole
Ketimine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organooxygen compound
Imine
Primary alcohol
Aromatic alcohol
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organohalogen compound
Organochloride
Organofluoride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0061089)
Liver (HMDB: HMDB0061089)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061089)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061089)

Cellular substructure

Cytoplasm (HMDB: HMDB0061089)
Membrane (HMDB: HMDB0061089)

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	0.025 g/L	ALOGPS
logP	3.09	ALOGPS
logP	2.48	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.95	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.41 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.13 m³·mol⁻¹	ChemAxon
Polarizability	33.74 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]-	210.92	30932474
DeepCCS	[M+Na]+	186.147	30932474
AllCCS	[M+H]+	177.0	32859911
AllCCS	[M+H-H2O]+	173.7	32859911
AllCCS	[M+NH4]+	180.0	32859911
AllCCS	[M+Na]+	180.9	32859911
AllCCS	[M-H]-	177.7	32859911
AllCCS	[M+Na-2H]-	176.8	32859911
AllCCS	[M+HCOO]-	176.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alpha-hydroxymidazolam	OCC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12	3998.2	Standard polar	33892256
Alpha-hydroxymidazolam	OCC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12	2825.2	Standard non polar	33892256
Alpha-hydroxymidazolam	OCC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12	2826.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alpha-hydroxymidazolam,1TMS,isomer #1	C[Si](C)(C)OCC1=NC=C2CN=C(C3=CC=CC=C3F)C3=CC(Cl)=CC=C3N21	2934.1	Semi standard non polar	33892256
Alpha-hydroxymidazolam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=NC=C2CN=C(C3=CC=CC=C3F)C3=CC(Cl)=CC=C3N21	3100.6	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 - Alpha-hydroxymidazolam GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-5095000000-e86a4f5a0a71a34e350b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alpha-hydroxymidazolam GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9223000000-3f514c7a0258e49e1f65	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alpha-hydroxymidazolam 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-hydroxymidazolam 30V, Positive-QTOF	splash10-00di-0049000000-d895e6063cea9b7a09f0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-hydroxymidazolam 50V, Positive-QTOF	splash10-014i-0990000000-77bb23f06e802e59ccd0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-hydroxymidazolam 40V, Positive-QTOF	splash10-0v6s-0492000000-63c05208d4d7c9ff0b8e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-hydroxymidazolam 50V, Positive-QTOF	splash10-014i-0890000000-77bb23f06e802e59ccd0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-hydroxymidazolam 10V, Positive-QTOF	splash10-0006-0009000000-1c56560c62733c03b222	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-hydroxymidazolam 20V, Positive-QTOF	splash10-0006-0009000000-8c1db0e6fec0c5c5a135	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-hydroxymidazolam 40V, Positive-QTOF	splash10-0v6s-0492000000-7c15b332e0c6a3e8fe39	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-hydroxymidazolam 30V, Positive-QTOF	splash10-00di-0049000000-30f3b10d1ecd517c40a6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 10V, Negative-QTOF	splash10-0006-0009000000-31e0874067a2b92c0d0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 20V, Negative-QTOF	splash10-01ox-0029000000-ff9099b2ad85a8e30147	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 40V, Negative-QTOF	splash10-0006-7091000000-c5de935b2501a445dbe7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 10V, Negative-QTOF	splash10-03dl-0089000000-3044806924cd101e751f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 20V, Negative-QTOF	splash10-00dl-1029000000-77d2ad85be5f7638949e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 40V, Negative-QTOF	splash10-001i-8091000000-9820c5ea13f2c191818c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 10V, Positive-QTOF	splash10-0006-0019000000-66ccd38bae3483f32c1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 20V, Positive-QTOF	splash10-0006-0029000000-93fa3c07dc10a1af479d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 40V, Positive-QTOF	splash10-0gk9-2691000000-e01f5df13f0f7059a2c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 10V, Positive-QTOF	splash10-0006-0009000000-90d80e8b23a2763d7125	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 20V, Positive-QTOF	splash10-00dl-0009000000-aa6995ead1e625eff164	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-hydroxymidazolam 40V, Positive-QTOF	splash10-05fs-0494000000-d7daea83a7f8e9b0ccda	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

107917

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 Alpha-hydroxymidazolam (HMDB0061089)

MOL for HMDB0061089 (Alpha-hydroxymidazolam)

3D MOL for HMDB0061089 (Alpha-hydroxymidazolam)

3D SDF for HMDB0061089 (Alpha-hydroxymidazolam)

3D-SDF for HMDB0061089 (Alpha-hydroxymidazolam)

PDB for HMDB0061089 (Alpha-hydroxymidazolam)

3D PDB for HMDB0061089 (Alpha-hydroxymidazolam)

SMILES for HMDB0061089 (Alpha-hydroxymidazolam)

INCHI for HMDB0061089 (Alpha-hydroxymidazolam)

Structure for HMDB0061089 (Alpha-hydroxymidazolam)

3D Structure for HMDB0061089 (Alpha-hydroxymidazolam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra