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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:58:06 UTC

Update Date

2021-09-14 15:02:27 UTC

HMDB ID

HMDB0060764

Secondary Accession Numbers

HMDB60764

Metabolite Identification

Common Name

4-Hydroxy-estazolam

Description

4-Hydroxy-estazolam is a metabolite of estazolam. Estazolam (marketed under the brand names ProSom, Eurodin) is a benzodiazepine derivative drug developed by Upjohn in the 1970s. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Estazolam is an intermediate-acting oral benzodiazepine. It is commonly prescribed for short-term treatment of insomnia. (Wikipedia )

Structure

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

HMDB0060764
     RDKit          3D
4-Hydroxy-estazolam
 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.7252   -2.7648    2.1497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202   -1.4880    1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2525   -1.3274    1.1574 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2947   -0.4467    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -0.5508    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    0.1560   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    0.0212   -0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4725   -0.8841   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319   -1.6170    0.8196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915   -1.4750    0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4159    0.7083   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220    1.8653   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2568    3.0211   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365    4.4687   -0.7629 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650    3.0542   -1.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322    1.9139   -1.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479    0.7872   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7019   -0.2625   -0.3854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7967   -0.4313   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4138   -1.5152   -0.6753 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876   -1.9976    0.3589 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6159   -1.2355    0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -3.1649    2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -0.7658    2.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733    0.8259   -1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3961    0.5933   -1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371   -1.0097   -0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2999   -2.3240    1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -2.0572    1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3205    1.8410    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0191    3.9791   -1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604    1.8957   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1191    0.1867   -1.9579 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  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 10  5  1  0
 17 11  1  0
 22 18  1  0
  1 23  1  0
  2 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
M  END

  Mrv0541 07041311582D          

 22 25  0  0  0  0            999 V2000
    5.8108   -3.3751    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
    5.0317   -3.6463    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
    4.4072   -3.1072    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
    2.4119    0.4414    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
    5.3034   -0.1145    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
    3.6635   -0.2965    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
    2.3000   -0.8888    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
    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
    1.5395   -0.5689    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18  9  2  0  0  0  0
 19 14  2  0  0  0  0
 19 16  1  0  0  0  0
 20 15  2  0  0  0  0
 20 18  1  0  0  0  0
 21  9  1  0  0  0  0
 21 13  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060764

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1N=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N2C=NN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H11ClN4O/c17-11-6-7-13-12(8-11)14(10-4-2-1-3-5-10)19-16(22)15-20-18-9-21(13)15/h1-9,16,22H

> <INCHI_KEY>
LJIJJCXFWLORDQ-UHFFFAOYSA-N

> <FORMULA>
C16H11ClN4O

> <MOLECULAR_WEIGHT>
310.738

> <EXACT_MASS>
310.062138701

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.511299146222512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
1.8283999999999998

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.908312952152416

> <JCHEM_PKA_STRONGEST_BASIC>
1.4260056815427071

> <JCHEM_POLAR_SURFACE_AREA>
63.3

> <JCHEM_REFRACTIVITY>
95.6367

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060764
     RDKit          3D
4-Hydroxy-estazolam
 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.7252   -2.7648    2.1497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202   -1.4880    1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2525   -1.3274    1.1574 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2947   -0.4467    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -0.5508    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    0.1560   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    0.0212   -0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4725   -0.8841   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319   -1.6170    0.8196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915   -1.4750    0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4159    0.7083   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220    1.8653   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2568    3.0211   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365    4.4687   -0.7629 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650    3.0542   -1.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322    1.9139   -1.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479    0.7872   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7019   -0.2625   -0.3854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7967   -0.4313   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4138   -1.5152   -0.6753 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876   -1.9976    0.3589 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6159   -1.2355    0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -3.1649    2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -0.7658    2.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733    0.8259   -1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3961    0.5933   -1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371   -1.0097   -0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2999   -2.3240    1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -2.0572    1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3205    1.8410    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0191    3.9791   -1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604    1.8957   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1191    0.1867   -1.9579 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  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 10  5  1  0
 17 11  1  0
 22 18  1  0
  1 23  1  0
  2 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0      10.847  -6.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.136  -4.788   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.393  -6.806   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.970  -3.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.227  -5.800   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       4.502   0.824   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.516  -4.287   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       7.751  -1.794   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.839  -0.553   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.350  -3.281   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.293  -1.659   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.577  -3.173   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      11.430  -0.044   0.000  0.00  0.00          Cl+0
HETATM   18  N   UNK     0       3.003   0.472   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       5.937  -3.894   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       2.874  -1.062   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       5.300  -0.493   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       3.336  -4.085   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    7   11                                                       
CONECT    7    6   13                                                       
CONECT    8   11   12                                                       
CONECT    9   18   21                                                       
CONECT   10    4    5   14                                                  
CONECT   11    6    8   17                                                  
CONECT   12    8   13   14                                                  
CONECT   13    7   12   21                                                  
CONECT   14   10   12   19                                                  
CONECT   15   16   20   21                                                  
CONECT   16   15   19   22                                                  
CONECT   17   11                                                            
CONECT   18    9   20                                                       
CONECT   19   14   16                                                       
CONECT   20   15   18                                                       
CONECT   21    9   13   15                                                  
CONECT   22   16                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0060764
HETATM    1  O1  UNL     1      -1.725  -2.765   2.150  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.620  -1.488   1.619  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.252  -1.327   1.157  1.00  0.00           N  
HETATM    4  C2  UNL     1       0.295  -0.447   0.399  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.693  -0.551   0.103  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.443   0.156  -0.776  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.814   0.021  -0.894  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.473  -0.884  -0.080  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.732  -1.617   0.820  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.391  -1.475   0.927  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.416   0.708  -0.084  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.322   1.865  -0.168  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.257   3.021  -0.664  1.00  0.00           C  
HETATM   14 CL1  UNL     1       0.736   4.469  -0.763  1.00  0.00          CL  
HETATM   15  C12 UNL     1      -1.565   3.054  -1.078  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.332   1.914  -1.000  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.748   0.787  -0.511  1.00  0.00           C  
HETATM   18  N2  UNL     1      -2.702  -0.262  -0.385  1.00  0.00           N  
HETATM   19  C15 UNL     1      -3.797  -0.431  -1.139  1.00  0.00           C  
HETATM   20  N3  UNL     1      -4.414  -1.515  -0.675  1.00  0.00           N  
HETATM   21  N4  UNL     1      -3.688  -1.998   0.359  1.00  0.00           N  
HETATM   22  C16 UNL     1      -2.616  -1.236   0.560  1.00  0.00           C  
HETATM   23  H1  UNL     1      -0.841  -3.165   2.358  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.785  -0.766   2.435  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.973   0.826  -1.487  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.396   0.593  -1.597  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.537  -1.010  -0.150  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.300  -2.324   1.444  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.830  -2.057   1.636  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.320   1.841   0.225  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.019   3.979  -1.474  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.360   1.896  -1.308  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.119   0.187  -1.958  1.00  0.00           H  
CONECT    1    2   23
CONECT    2    3   22   24
CONECT    3    4    4
CONECT    4    5   11
CONECT    5    6    6   10
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   29
CONECT   11   12   12   17
CONECT   12   13   30
CONECT   13   14   15   15
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18
CONECT   18   19   22
CONECT   19   20   20   33
CONECT   20   21
CONECT   21   22   22
END

HMDB0060764
     RDKit          3D
4-Hydroxy-estazolam
 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.7252   -2.7648    2.1497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202   -1.4880    1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2525   -1.3274    1.1574 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2947   -0.4467    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -0.5508    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    0.1560   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    0.0212   -0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4725   -0.8841   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319   -1.6170    0.8196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915   -1.4750    0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4159    0.7083   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220    1.8653   -0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2568    3.0211   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365    4.4687   -0.7629 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650    3.0542   -1.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322    1.9139   -1.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479    0.7872   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7019   -0.2625   -0.3854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7967   -0.4313   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4138   -1.5152   -0.6753 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876   -1.9976    0.3589 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6159   -1.2355    0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -3.1649    2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -0.7658    2.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733    0.8259   -1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3961    0.5933   -1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371   -1.0097   -0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2999   -2.3240    1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -2.0572    1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3205    1.8410    0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0191    3.9791   -1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604    1.8957   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1191    0.1867   -1.9579 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  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 10  5  1  0
 17 11  1  0
 22 18  1  0
  1 23  1  0
  2 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
HYDROXYAMFETAMINE	HMDB
Hydrobromide, hydroxyamphetamine	HMDB
Hydroxyamphetamin	HMDB
Hydroxyamphetamine hydrobromide	HMDB
Norpholedrin	HMDB
Oxyamphetamine	HMDB
p-Hydroxyamphetamine	HMDB
Para hydroxyamphetamine	HMDB
Hydroxyphenylisopropylamine	HMDB
Paredrine	HMDB
p Hydroxyamphetamine	HMDB
Para-hydroxyamphetamine	HMDB
Methyltyramine	HMDB

Chemical Formula

C₁₆H₁₁ClN₄O

Average Molecular Weight

310.738

Monoisotopic Molecular Weight

310.062138701

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1N=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N2C=NN=C12

InChI Identifier

InChI=1S/C16H11ClN4O/c17-11-6-7-13-12(8-11)14(10-4-2-1-3-5-10)19-16(22)15-20-18-9-21(13)15/h1-9,16,22H

InChI Key

LJIJJCXFWLORDQ-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: HMDB0060764)

Organ

Kidney (HMDB: HMDB0060764)
Liver (HMDB: HMDB0060764)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060764)

Cellular substructure

Cytoplasm (HMDB: HMDB0060764)

Source

Endogenous

Endogenous (HMDB: HMDB0060764)

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	0.11 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.83	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.91	ChemAxon
pKa (Strongest Basic)	1.43	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	95.64 m³·mol⁻¹	ChemAxon
Polarizability	30.51 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]-	196.834	30932474
DeepCCS	[M+Na]+	172.061	30932474
AllCCS	[M+H]+	170.4	32859911
AllCCS	[M+H-H2O]+	166.8	32859911
AllCCS	[M+NH4]+	173.7	32859911
AllCCS	[M+Na]+	174.6	32859911
AllCCS	[M-H]-	170.5	32859911
AllCCS	[M+Na-2H]-	169.5	32859911
AllCCS	[M+HCOO]-	168.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-estazolam	OC1N=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N2C=NN=C12	4111.4	Standard polar	33892256
4-Hydroxy-estazolam	OC1N=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N2C=NN=C12	2957.7	Standard non polar	33892256
4-Hydroxy-estazolam	OC1N=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N2C=NN=C12	2955.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-estazolam,1TMS,isomer #1	C[Si](C)(C)OC1N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C2N2C=NN=C12	2957.4	Semi standard non polar	33892256
4-Hydroxy-estazolam,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1N=C(C2=CC=CC=C2)C2=CC(Cl)=CC=C2N2C=NN=C12	3136.5	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-Hydroxy-estazolam GC-MS (Non-derivatized) - 70eV, Positive	splash10-00pj-5490000000-44347329267f2821b6f3	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-estazolam GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9015000000-2866ec0853a7ec87e93f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-estazolam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-estazolam 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-Hydroxy-estazolam 10V, Positive-QTOF	splash10-03di-0019000000-9065bfb94f285db9c6d3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 20V, Positive-QTOF	splash10-03di-0029000000-5850bc72961e89c945fd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 40V, Positive-QTOF	splash10-03dr-8970000000-56dcf7de55d0781d0c8c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 10V, Negative-QTOF	splash10-0a4i-0019000000-f351a03484cf4f1999cd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 20V, Negative-QTOF	splash10-0a4i-0049000000-eeb0f64ed0793bdee360	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 40V, Negative-QTOF	splash10-014i-1090000000-fd728b673e98d6298e07	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 10V, Positive-QTOF	splash10-03di-0009000000-ae254a9e6449ecf6ab17	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 20V, Positive-QTOF	splash10-03di-0019000000-7c1468407f870cf09ac9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 40V, Positive-QTOF	splash10-001i-1191000000-a45c0718f52f4b271b28	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 10V, Negative-QTOF	splash10-0a4i-0019000000-e6ccb3e2a2b31d96cf00	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 20V, Negative-QTOF	splash10-0a4i-0019000000-62ac3fab9e7bbdea3195	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-estazolam 40V, Negative-QTOF	splash10-00lr-9010000000-4c81802a15dae4e4e739	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9841473

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Hydroxyamphetamine

METLIN ID

Not Available

PubChem Compound

3651

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-Hydroxy-estazolam (HMDB0060764)

MOL for HMDB0060764 (4-Hydroxy-estazolam)

3D MOL for HMDB0060764 (4-Hydroxy-estazolam)

3D SDF for HMDB0060764 (4-Hydroxy-estazolam)

3D-SDF for HMDB0060764 (4-Hydroxy-estazolam)

PDB for HMDB0060764 (4-Hydroxy-estazolam)

3D PDB for HMDB0060764 (4-Hydroxy-estazolam)

SMILES for HMDB0060764 (4-Hydroxy-estazolam)

INCHI for HMDB0060764 (4-Hydroxy-estazolam)

Structure for HMDB0060764 (4-Hydroxy-estazolam)

3D Structure for HMDB0060764 (4-Hydroxy-estazolam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra