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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:33:55 UTC

Update Date

2021-09-14 15:46:31 UTC

HMDB ID

HMDB0060554

Secondary Accession Numbers

HMDB60554

Metabolite Identification

Common Name

4-hydroxyalprazolam

Description

4-Hydroxyalprazolam is a metaboltie of Alprazolam. Alprazolam (trade name Xanax, available among other generic names) is a short-acting anxiolytic of the benzodiazepine class of psychoactive drugs. Alprazolam is extensively metabolized in humans, primarily by cytochrome P450 3A4 (Cyp3A4), to two major metabolites in plasma: 4-hydroxyalprazolam and Î±- hydroxyalprazolam. (Wikipedia)

Structure

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

HMDB0060554
     RDKit          3D
4-hydroxyalprazolam
 36 39  0  0  0  0  0  0  0  0999 V2000
   -3.6735    0.2312    2.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1202   -0.8861    1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4276   -2.2198    1.3293 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6424   -2.9268    0.4901 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8436   -2.0993   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585   -0.8460    0.3320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480    0.3669   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4422    1.3923   -0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    2.5951   -0.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892    2.7255   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0607    4.2550   -1.6522 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    1.6464   -0.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    0.4518   -0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918   -0.6065   -0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428   -0.2215   -0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482   -1.1950   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4507   -1.0176    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8507    0.1651    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9049    1.1425    0.8321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866    0.9214    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -1.8455   -0.7387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7933   -2.4550   -1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -2.0871   -2.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7568   -0.2117    3.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7107    0.5032    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9702    1.0601    2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4615    1.2592    0.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5748    3.4309   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    1.6849   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8495   -2.1181   -0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2219   -1.7788   -0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8698    0.3106    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010    2.0707    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812    1.7013    0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140   -3.5461   -1.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828   -1.8534   -2.9380 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
 14 21  2  0
 21 22  1  0
 22 23  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 22  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 22 35  1  0
 23 36  1  0
M  END

404
  Mrv0541 02271201072D          

 23 26  0  0  0  0            999 V2000
    1.6500   -0.2321    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -1.3269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284    0.4805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244   -1.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7352   -2.2849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0726   -0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5592   -0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034    0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9281   -2.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4517   -1.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718    0.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0454    1.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286   -1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374   -0.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328   -2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2227    1.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5102    1.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648    2.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1523    2.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296    2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5397    0.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2  6  1  0  0  0  0
  2  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3  9  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  2  0  0  0  0
  5 11  2  0  0  0  0
  6  7  2  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  7 13  1  0  0  0  0
  8 10  1  0  0  0  0
  9 14  1  0  0  0  0
 11 17  1  0  0  0  0
 12 15  2  0  0  0  0
 13 16  2  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 10 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060554

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H13ClN4O/c1-10-20-21-16-17(23)19-15(11-5-3-2-4-6-11)13-9-12(18)7-8-14(13)22(10)16/h2-9,17,23H,1H3

> <INCHI_KEY>
CEYGCFLPQFNPST-UHFFFAOYSA-N

> <FORMULA>
C17H13ClN4O

> <MOLECULAR_WEIGHT>
324.764

> <EXACT_MASS>
324.077788765

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.58612940864015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.1112

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.967776767404075

> <JCHEM_PKA_STRONGEST_BASIC>
2.0085815187185094

> <JCHEM_POLAR_SURFACE_AREA>
63.3

> <JCHEM_REFRACTIVITY>
100.07740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.75e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060554
     RDKit          3D
4-hydroxyalprazolam
 36 39  0  0  0  0  0  0  0  0999 V2000
   -3.6735    0.2312    2.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1202   -0.8861    1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4276   -2.2198    1.3293 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6424   -2.9268    0.4901 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8436   -2.0993   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585   -0.8460    0.3320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480    0.3669   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4422    1.3923   -0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    2.5951   -0.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892    2.7255   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0607    4.2550   -1.6522 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    1.6464   -0.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    0.4518   -0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918   -0.6065   -0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428   -0.2215   -0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482   -1.1950   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4507   -1.0176    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8507    0.1651    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9049    1.1425    0.8321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866    0.9214    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -1.8455   -0.7387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7933   -2.4550   -1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -2.0871   -2.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7568   -0.2117    3.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7107    0.5032    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9702    1.0601    2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4615    1.2592    0.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5748    3.4309   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    1.6849   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8495   -2.1181   -0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2219   -1.7788   -0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8698    0.3106    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010    2.0707    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812    1.7013    0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140   -3.5461   -1.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828   -1.8534   -2.9380 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
 14 21  2  0
 21 22  1  0
 22 23  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 22  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 22 35  1  0
 23 36  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 404                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -0.433   0.000  0.00  0.00          Cl+0
HETATM    2  N   UNK     0       8.990  -2.477   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.760   0.897   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      11.432  -2.918   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      10.706  -4.265   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.602  -1.809   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.259  -0.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.377  -1.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.220   0.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.720  -0.307   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.199  -3.993   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.443  -2.918   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.734   0.189   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.551   2.284   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.907  -2.457   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.550  -0.893   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.088  -5.059   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.016   2.399   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.419   3.557   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.348   3.787   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.751   4.944   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.215   5.059   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.207   0.091   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2    6    8   11                                                  
CONECT    3    9   10                                                       
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    2    7   12                                                  
CONECT    7    6    9   13                                                  
CONECT    8    2    4   10                                                  
CONECT    9    3    7   14                                                  
CONECT   10    3    8   23                                                  
CONECT   11    2    5   17                                                  
CONECT   12    6   15                                                       
CONECT   13    7   16                                                       
CONECT   14    9   18   19                                                  
CONECT   15   12   16                                                       
CONECT   16    1   13   15                                                  
CONECT   17   11                                                            
CONECT   18   14   20                                                       
CONECT   19   14   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   22                                                       
CONECT   22   20   21                                                       
CONECT   23   10                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0060554
HETATM    1  C1  UNL     1      -3.674   0.231   2.009  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.120  -0.886   1.234  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.428  -2.220   1.329  1.00  0.00           N  
HETATM    4  N2  UNL     1      -2.642  -2.927   0.490  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.844  -2.099  -0.140  1.00  0.00           C  
HETATM    6  N3  UNL     1      -2.159  -0.846   0.332  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.548   0.367  -0.108  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.442   1.392  -0.176  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.908   2.595  -0.663  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.589   2.725  -1.046  1.00  0.00           C  
HETATM   11 CL1  UNL     1       0.061   4.255  -1.652  1.00  0.00          CL  
HETATM   12  C8  UNL     1       0.258   1.646  -0.955  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.197   0.452  -0.484  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.792  -0.606  -0.455  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.143  -0.221  -0.142  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.148  -1.195  -0.335  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.451  -1.018   0.029  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.851   0.165   0.622  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.905   1.142   0.832  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.587   0.921   0.448  1.00  0.00           C  
HETATM   21  N4  UNL     1       0.493  -1.846  -0.739  1.00  0.00           N  
HETATM   22  C17 UNL     1      -0.793  -2.455  -1.118  1.00  0.00           C  
HETATM   23  O1  UNL     1      -1.179  -2.087  -2.396  1.00  0.00           O  
HETATM   24  H1  UNL     1      -3.757  -0.212   3.070  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.711   0.503   1.822  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.970   1.060   2.237  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.462   1.259   0.063  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.575   3.431  -0.729  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.282   1.685  -1.307  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.849  -2.118  -0.796  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.222  -1.779  -0.126  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.870   0.311   0.909  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.201   2.071   1.294  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.881   1.701   0.706  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.614  -3.546  -1.055  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.383  -1.853  -2.938  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    6
CONECT    3    4
CONECT    4    5    5
CONECT    5    6   22
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   12
CONECT   12   13   13   29
CONECT   13   14
CONECT   14   15   21   21
CONECT   15   16   16   20
CONECT   16   17   30
CONECT   17   18   18   31
CONECT   18   19   32
CONECT   19   20   20   33
CONECT   20   34
CONECT   21   22
CONECT   22   23   35
CONECT   23   36
END

HMDB0060554
     RDKit          3D
4-hydroxyalprazolam
 36 39  0  0  0  0  0  0  0  0999 V2000
   -3.6735    0.2312    2.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1202   -0.8861    1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4276   -2.2198    1.3293 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6424   -2.9268    0.4901 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8436   -2.0993   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585   -0.8460    0.3320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480    0.3669   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4422    1.3923   -0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    2.5951   -0.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892    2.7255   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0607    4.2550   -1.6522 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    1.6464   -0.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    0.4518   -0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918   -0.6065   -0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428   -0.2215   -0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482   -1.1950   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4507   -1.0176    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8507    0.1651    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9049    1.1425    0.8321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866    0.9214    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -1.8455   -0.7387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7933   -2.4550   -1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -2.0871   -2.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7568   -0.2117    3.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7107    0.5032    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9702    1.0601    2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4615    1.2592    0.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5748    3.4309   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    1.6849   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8495   -2.1181   -0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2219   -1.7788   -0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8698    0.3106    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010    2.0707    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812    1.7013    0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140   -3.5461   -1.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828   -1.8534   -2.9380 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
 14 21  2  0
 21 22  1  0
 22 23  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 22  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 22 35  1  0
 23 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-alprazolam(0.3%)	HMDB

Chemical Formula

C₁₇H₁₃ClN₄O

Average Molecular Weight

324.764

Monoisotopic Molecular Weight

324.077788765

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H13ClN4O/c1-10-20-21-16-17(23)19-15(11-5-3-2-4-6-11)13-9-12(18)7-8-14(13)22(10)16/h2-9,17,23H,1H3

InChI Key

CEYGCFLPQFNPST-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
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Azole
Heteroaromatic compound
1,2,4-triazole
Ketimine
Alkanolamine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organochloride
Organohalogen compound
Imine
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060554)

Organ

Kidney (HMDB: HMDB0060554)
Liver (HMDB: HMDB0060554)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060554)

Cellular substructure

Cytoplasm (HMDB: HMDB0060554)
Membrane (HMDB: HMDB0060554)

Source

Endogenous

Endogenous (HMDB: HMDB0060554)

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	0.088 g/L	ALOGPS
logP	2.42	ALOGPS
logP	2.11	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	10.97	ChemAxon
pKa (Strongest Basic)	2.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	100.08 m³·mol⁻¹	ChemAxon
Polarizability	32.59 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]-	205.029	30932474
DeepCCS	[M+Na]+	180.256	30932474
AllCCS	[M+H]+	173.9	32859911
AllCCS	[M+H-H2O]+	170.4	32859911
AllCCS	[M+NH4]+	177.1	32859911
AllCCS	[M+Na]+	178.1	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	174.3	32859911
AllCCS	[M+HCOO]-	173.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-hydroxyalprazolam	CC1=NN=C2C(O)N=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12	4106.1	Standard polar	33892256
4-hydroxyalprazolam	CC1=NN=C2C(O)N=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12	3022.6	Standard non polar	33892256
4-hydroxyalprazolam	CC1=NN=C2C(O)N=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12	2922.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-hydroxyalprazolam,1TMS,isomer #1	CC1=NN=C2C(O[Si](C)(C)C)N=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N12	3049.7	Semi standard non polar	33892256
4-hydroxyalprazolam,1TBDMS,isomer #1	CC1=NN=C2C(O[Si](C)(C)C(C)(C)C)N=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N12	3217.9	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-hydroxyalprazolam GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5291000000-18a84fdfd5aee1c59e5c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-hydroxyalprazolam GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9004000000-17974f2cc5cf66c63ef5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-hydroxyalprazolam 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-hydroxyalprazolam 10V, Positive-QTOF	splash10-004i-0009000000-d7f096d1f62e6b5d858a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 20V, Positive-QTOF	splash10-004i-0039000000-4e6beb51e3e5aa073415	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 40V, Positive-QTOF	splash10-03di-5971000000-b9f1fb1b7aa56cff9a8b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 10V, Negative-QTOF	splash10-00di-0019000000-d9cbab94ad5dd6c91611	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 20V, Negative-QTOF	splash10-00di-0069000000-14f58ec9c559e1742555	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 40V, Negative-QTOF	splash10-00lu-8290000000-fe822d004acc8e9cf953	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 10V, Positive-QTOF	splash10-004i-0009000000-17da94791e2d780448e0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 20V, Positive-QTOF	splash10-004i-0029000000-882acdbc40b1650406b4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 40V, Positive-QTOF	splash10-00kb-0090000000-2e8ed56db0f434e123d8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 10V, Negative-QTOF	splash10-00di-0009000000-5ff932028446d58aa723	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 20V, Negative-QTOF	splash10-00di-0019000000-ad8aaa778c96160cf24d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxyalprazolam 40V, Negative-QTOF	splash10-001i-9022000000-3aefe13b679525903a2a	2021-10-12	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

158315

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182017

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-hydroxyalprazolam (HMDB0060554)

MOL for HMDB0060554 (4-hydroxyalprazolam)

3D MOL for HMDB0060554 (4-hydroxyalprazolam)

3D SDF for HMDB0060554 (4-hydroxyalprazolam)

3D-SDF for HMDB0060554 (4-hydroxyalprazolam)

PDB for HMDB0060554 (4-hydroxyalprazolam)

3D PDB for HMDB0060554 (4-hydroxyalprazolam)

SMILES for HMDB0060554 (4-hydroxyalprazolam)

INCHI for HMDB0060554 (4-hydroxyalprazolam)

Structure for HMDB0060554 (4-hydroxyalprazolam)

3D Structure for HMDB0060554 (4-hydroxyalprazolam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra