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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:17:38 UTC

Update Date

2021-09-14 15:46:31 UTC

HMDB ID

HMDB0061090

Secondary Accession Numbers

HMDB61090

Metabolite Identification

Common Name

4-hydroxymidazolam

Description

4-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

HMDB0061090
     RDKit          3D
4-hydroxymidazolam
 37 40  0  0  0  0  0  0  0  0999 V2000
    3.9172   -1.1221    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854    0.2033    0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    1.3099    1.2965 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102    2.3182    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    1.8635    0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340    0.5788    0.0814 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3592   -0.2927   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1313   -1.0689   -1.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4240   -1.8847   -2.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241   -1.8746   -2.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8406   -2.9066   -3.6265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -1.0661   -1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0448   -0.2550   -0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9304    0.5618    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1743    0.0083    0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598    0.8913    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366    0.4495    1.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6159   -0.8859    1.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876   -1.7744    1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -1.3059    0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6027   -2.3080    0.2648 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549    1.7934    0.3517 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254    2.5640   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    3.8283    0.4936 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2806   -1.2986    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544   -1.2091   -0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2106   -1.9792    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501    3.3123    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -1.0068   -1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048   -2.5046   -3.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962   -0.9809   -1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0044    1.9617    0.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0968    1.1286    1.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5335   -1.2662    1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8838   -2.8308    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597    2.5990   -1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0078    4.4491   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 14 22  2  0
 22 23  1  0
 23 24  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 12 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 23 36  1  0
 24 37  1  0
M  END


  Mrv0541 07091309172D          

 24 27  0  0  0  0            999 V2000
    2.7317    1.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0317   -3.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108   -3.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4072   -3.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9655   -2.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8146    0.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9947    0.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9723   -0.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4119    0.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034   -0.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619   -2.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1523   -0.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3411   -2.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6635   -0.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -1.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -1.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1234   -0.0234    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4958   -1.2152    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    0.2531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1808   -2.0863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8392   -0.2643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874   -2.1884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
 10  1  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  4  2  0  0  0  0
 13  8  1  0  0  0  0
 14  5  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  2  0  0  0  0
 16  9  2  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 16  1  0  0  0  0
 19 11  1  0  0  0  0
 20 14  1  0  0  0  0
 21  9  1  0  0  0  0
 21 10  2  0  0  0  0
 22 17  2  0  0  0  0
 22 18  1  0  0  0  0
 23 10  1  0  0  0  0
 23 15  1  0  0  0  0
 23 16  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061090

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC=C2C(O)N=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12

> <INCHI_IDENTIFIER>
InChI=1S/C18H13ClFN3O/c1-10-21-9-16-18(24)22-17(12-4-2-3-5-14(12)20)13-8-11(19)6-7-15(13)23(10)16/h2-9,18,24H,1H3

> <INCHI_KEY>
ZYISITHKPKHPKG-UHFFFAOYSA-N

> <FORMULA>
C18H13ClFN3O

> <MOLECULAR_WEIGHT>
341.767

> <EXACT_MASS>
341.073117965

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.39128001219298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-chloro-9-(2-fluorophenyl)-3-methyl-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-7-ol

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.929300000000001

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.544888260268175

> <JCHEM_PKA_STRONGEST_BASIC>
6.250608258808527

> <JCHEM_POLAR_SURFACE_AREA>
50.41

> <JCHEM_REFRACTIVITY>
100.45960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-chloro-9-(2-fluorophenyl)-3-methyl-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061090
     RDKit          3D
4-hydroxymidazolam
 37 40  0  0  0  0  0  0  0  0999 V2000
    3.9172   -1.1221    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854    0.2033    0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    1.3099    1.2965 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102    2.3182    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    1.8635    0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340    0.5788    0.0814 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3592   -0.2927   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1313   -1.0689   -1.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4240   -1.8847   -2.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241   -1.8746   -2.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8406   -2.9066   -3.6265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -1.0661   -1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0448   -0.2550   -0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9304    0.5618    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1743    0.0083    0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598    0.8913    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366    0.4495    1.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6159   -0.8859    1.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876   -1.7744    1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -1.3059    0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6027   -2.3080    0.2648 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549    1.7934    0.3517 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254    2.5640   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    3.8283    0.4936 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2806   -1.2986    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544   -1.2091   -0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2106   -1.9792    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501    3.3123    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -1.0068   -1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048   -2.5046   -3.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962   -0.9809   -1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0044    1.9617    0.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0968    1.1286    1.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5335   -1.2662    1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8838   -2.8308    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597    2.5990   -1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0078    4.4491   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 14 22  2  0
 22 23  1  0
 23 24  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 12 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 23 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       5.099   2.244   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.393  -6.806   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.847  -6.300   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.227  -5.800   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.136  -4.788   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.987   1.027   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.457   0.857   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.282  -1.624   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874  -1.062   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.502   0.824   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.900  -0.214   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.516  -4.287   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.751  -1.794   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.970  -3.781   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.839  -0.553   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.293  -1.659   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.350  -3.281   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.577  -3.173   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      11.430  -0.044   0.000  0.00  0.00          Cl+0
HETATM   20  F   UNK     0      10.259  -2.268   0.000  0.00  0.00           F+0
HETATM   21  N   UNK     0       3.003   0.472   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       5.937  -3.894   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       5.300  -0.493   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       3.336  -4.085   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   12                                                       
CONECT    5    3   14                                                       
CONECT    6    7   11                                                       
CONECT    7    6   15                                                       
CONECT    8   11   13                                                       
CONECT    9   16   21                                                       
CONECT   10    1   21   23                                                  
CONECT   11    6    8   19                                                  
CONECT   12    4   14   17                                                  
CONECT   13    8   15   17                                                  
CONECT   14    5   12   20                                                  
CONECT   15    7   13   23                                                  
CONECT   16    9   18   23                                                  
CONECT   17   12   13   22                                                  
CONECT   18   16   22   24                                                  
CONECT   19   11                                                            
CONECT   20   14                                                            
CONECT   21    9   10                                                       
CONECT   22   17   18                                                       
CONECT   23   10   15   16                                                  
CONECT   24   18                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0061090
HETATM    1  C1  UNL     1       3.917  -1.122   0.531  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.285   0.203   0.608  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.710   1.310   1.297  1.00  0.00           N  
HETATM    4  C3  UNL     1       2.810   2.318   1.174  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.800   1.863   0.402  1.00  0.00           C  
HETATM    6  N2  UNL     1       2.134   0.579   0.081  1.00  0.00           N  
HETATM    7  C5  UNL     1       1.359  -0.293  -0.761  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.131  -1.069  -1.572  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.424  -1.885  -2.467  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.024  -1.875  -2.503  1.00  0.00           C  
HETATM   11 CL1  UNL     1      -0.841  -2.907  -3.626  1.00  0.00          CL  
HETATM   12  C9  UNL     1      -0.704  -1.066  -1.662  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.045  -0.255  -0.764  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.930   0.562   0.047  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.174   0.008   0.446  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.160   0.891   0.947  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.337   0.450   1.492  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.616  -0.886   1.577  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.688  -1.774   1.105  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.498  -1.306   0.557  1.00  0.00           C  
HETATM   21  F1  UNL     1      -1.603  -2.308   0.265  1.00  0.00           F  
HETATM   22  N3  UNL     1      -0.655   1.793   0.352  1.00  0.00           N  
HETATM   23  C18 UNL     1       0.525   2.564  -0.022  1.00  0.00           C  
HETATM   24  O1  UNL     1       0.499   3.828   0.494  1.00  0.00           O  
HETATM   25  H1  UNL     1       4.281  -1.299   1.611  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.854  -1.209  -0.007  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.211  -1.979   0.456  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.850   3.312   1.594  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.192  -1.007  -1.561  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.005  -2.505  -3.110  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.796  -0.981  -1.698  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.004   1.962   0.912  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.097   1.129   1.879  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.533  -1.266   1.998  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.884  -2.831   1.159  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.560   2.599  -1.125  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.008   4.449  -0.105  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    6
CONECT    3    4
CONECT    4    5    5   28
CONECT    5    6   23
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   12
CONECT   12   13   13   31
CONECT   13   14
CONECT   14   15   22   22
CONECT   15   16   16   20
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   18   19   34
CONECT   19   20   20   35
CONECT   20   21
CONECT   22   23
CONECT   23   24   36
CONECT   24   37
END

HMDB0061090
     RDKit          3D
4-hydroxymidazolam
 37 40  0  0  0  0  0  0  0  0999 V2000
    3.9172   -1.1221    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854    0.2033    0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    1.3099    1.2965 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102    2.3182    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    1.8635    0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340    0.5788    0.0814 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3592   -0.2927   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1313   -1.0689   -1.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4240   -1.8847   -2.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241   -1.8746   -2.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8406   -2.9066   -3.6265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -1.0661   -1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0448   -0.2550   -0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9304    0.5618    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1743    0.0083    0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598    0.8913    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366    0.4495    1.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6159   -0.8859    1.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876   -1.7744    1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -1.3059    0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6027   -2.3080    0.2648 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549    1.7934    0.3517 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254    2.5640   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    3.8283    0.4936 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2806   -1.2986    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8544   -1.2091   -0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2106   -1.9792    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501    3.3123    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1916   -1.0068   -1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048   -2.5046   -3.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962   -0.9809   -1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0044    1.9617    0.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0968    1.1286    1.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5335   -1.2662    1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8838   -2.8308    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597    2.5990   -1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0078    4.4491   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 14 22  2  0
 22 23  1  0
 23 24  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 12 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 23 36  1  0
 24 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-OH-MDZ	HMDB

Chemical Formula

C₁₈H₁₃ClFN₃O

Average Molecular Weight

341.767

Monoisotopic Molecular Weight

341.073117965

IUPAC Name

12-chloro-9-(2-fluorophenyl)-3-methyl-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-7-ol

Traditional Name

12-chloro-9-(2-fluorophenyl)-3-methyl-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-7-ol

CAS Registry Number

Not Available

SMILES

CC1=NC=C2C(O)N=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12

InChI Identifier

InChI=1S/C18H13ClFN3O/c1-10-21-9-16-18(24)22-17(12-4-2-3-5-14(12)20)13-8-11(19)6-7-15(13)23(10)16/h2-9,18,24H,1H3

InChI Key

ZYISITHKPKHPKG-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
Alkanolamine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Imine
Organofluoride
Organochloride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0061090)
Liver (HMDB: HMDB0061090)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061090)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061090)

Cellular substructure

Cytoplasm (HMDB: HMDB0061090)
Membrane (HMDB: HMDB0061090)

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	0.024 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.93	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.54	ChemAxon
pKa (Strongest Basic)	6.25	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	1	ChemAxon
Refractivity	100.46 m³·mol⁻¹	ChemAxon
Polarizability	33.39 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]-	211.591	30932474
DeepCCS	[M+Na]+	186.817	30932474
AllCCS	[M+H]+	177.1	32859911
AllCCS	[M+H-H2O]+	173.8	32859911
AllCCS	[M+NH4]+	180.2	32859911
AllCCS	[M+Na]+	181.1	32859911
AllCCS	[M-H]-	178.0	32859911
AllCCS	[M+Na-2H]-	177.1	32859911
AllCCS	[M+HCOO]-	176.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-hydroxymidazolam	CC1=NC=C2C(O)N=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12	3904.6	Standard polar	33892256
4-hydroxymidazolam	CC1=NC=C2C(O)N=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12	2640.6	Standard non polar	33892256
4-hydroxymidazolam	CC1=NC=C2C(O)N=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12	2733.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-hydroxymidazolam,1TMS,isomer #1	CC1=NC=C2C(O[Si](C)(C)C)N=C(C3=CC=CC=C3F)C3=CC(Cl)=CC=C3N21	2894.2	Semi standard non polar	33892256
4-hydroxymidazolam,1TBDMS,isomer #1	CC1=NC=C2C(O[Si](C)(C)C(C)(C)C)N=C(C3=CC=CC=C3F)C3=CC(Cl)=CC=C3N21	3060.8	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 - 4-hydroxymidazolam GC-MS (Non-derivatized) - 70eV, Positive	splash10-06rx-8369000000-46f68cf22df7c77d36de	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-hydroxymidazolam GC-MS (1 TMS) - 70eV, Positive	splash10-0096-9005000000-4f06a0de05183914a748	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 10V, Positive-QTOF	splash10-0006-0019000000-338b8c1f2dd67c728fde	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 20V, Positive-QTOF	splash10-0006-0009000000-5fc8b2cd3d1a989ce0a0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 40V, Positive-QTOF	splash10-06wc-6891000000-2cb760d2721ded25bbf6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 10V, Negative-QTOF	splash10-0006-0009000000-d856567ab6a9b201ebcc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 20V, Negative-QTOF	splash10-0006-0019000000-07d8ba262c075dc5374e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 40V, Negative-QTOF	splash10-00or-9042000000-c0378204caa0a62deff3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 10V, Negative-QTOF	splash10-00di-0009000000-ee84cc3bc355b081f0dc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 20V, Negative-QTOF	splash10-00di-0009000000-7ede497770c4f8ed497c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 40V, Negative-QTOF	splash10-001i-9022000000-95017fc801dfd2cb2a50	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 10V, Positive-QTOF	splash10-0006-0009000000-90d80e8b23a2763d7125	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 20V, Positive-QTOF	splash10-0006-0009000000-9ac36190282b25253e9a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxymidazolam 40V, Positive-QTOF	splash10-03dl-4497000000-9c08ca6fb2f67461b383	2021-09-23	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

124449

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 4-hydroxymidazolam (HMDB0061090)

MOL for HMDB0061090 (4-hydroxymidazolam)

3D MOL for HMDB0061090 (4-hydroxymidazolam)

3D SDF for HMDB0061090 (4-hydroxymidazolam)

3D-SDF for HMDB0061090 (4-hydroxymidazolam)

PDB for HMDB0061090 (4-hydroxymidazolam)

3D PDB for HMDB0061090 (4-hydroxymidazolam)

SMILES for HMDB0061090 (4-hydroxymidazolam)

INCHI for HMDB0061090 (4-hydroxymidazolam)

Structure for HMDB0061090 (4-hydroxymidazolam)

3D Structure for HMDB0061090 (4-hydroxymidazolam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra