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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 18:42:39 UTC

Update Date

2021-09-14 14:58:08 UTC

HMDB ID

HMDB0060676

Secondary Accession Numbers

HMDB60676

Metabolite Identification

Common Name

10-Hydroxycarbazepine

Description

10-Hydroxycarbazepine, also known as GP 47779 or 10,11-MHD, belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. In humans, 10-hydroxycarbazepine is involved in the carbamazepine metabolism pathway. 10-Hydroxycarbazepine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 10-Hydroxycarbazepine.

Structure

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

HMDB0060676
     RDKit          3D
10-Hydroxycarbazepine
 33 35  0  0  0  0  0  0  0  0999 V2000
    2.0448    2.7067   -1.0008 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543    2.2761   -0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    3.2133   -0.6430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.0227   -0.1381 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817   -0.0583   -0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157    0.4452    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.4390    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -1.7938    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960   -2.2643   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0006   -1.4025   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200   -2.1463   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -1.4303   -0.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -2.3225   -1.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8179   -0.2378   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1503   -0.1790    0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6762    0.8820    0.8485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8800    1.9685    1.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5505    1.9312    0.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0509    0.8541    0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614    3.5460   -0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345    2.1757   -1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6808    1.4809    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5378   -0.0697    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833   -2.4698    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9216   -3.3177   -0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0664   -2.9330   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4892   -2.8238    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2089   -1.1842   -2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5427   -2.8644   -0.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977   -1.0159   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7424    0.8867    1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2627    2.8186    1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883    2.7444    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

 
  Mrv0541 06181311422D          
 
 19 21  0  0  0  0            999 V2000
   11.6137   -9.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3503   -9.0344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1004   -9.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2968  -10.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4441  -10.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7976  -10.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9719  -10.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0893  -10.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6841   -9.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4877   -9.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6952   -8.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9986   -8.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2149   -9.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0453   -9.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6605  -10.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1760  -11.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3373   -8.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6135   -7.8058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0424   -7.7866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  2  3  1  0  0  0  0
  5  7  1  0  0  0  0
  1  2  1  0  0  0  0
  6  7  1  0  0  0  0
  4  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  2  0  0  0  0
  1 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  5 15  2  0  0  0  0
  6 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060676

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)

> <INCHI_KEY>
BMPDWHIDQYTSHX-UHFFFAOYSA-N

> <FORMULA>
C15H14N2O2

> <MOLECULAR_WEIGHT>
254.2839

> <EXACT_MASS>
254.105527702

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.31043276402058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.7317409759999998

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.966328258863758

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.100105594069575

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1897706968030954

> <JCHEM_POLAR_SURFACE_AREA>
66.56

> <JCHEM_REFRACTIVITY>
72.2869

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060676
     RDKit          3D
10-Hydroxycarbazepine
 33 35  0  0  0  0  0  0  0  0999 V2000
    2.0448    2.7067   -1.0008 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543    2.2761   -0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    3.2133   -0.6430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.0227   -0.1381 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817   -0.0583   -0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157    0.4452    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.4390    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -1.7938    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960   -2.2643   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0006   -1.4025   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200   -2.1463   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -1.4303   -0.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -2.3225   -1.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8179   -0.2378   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1503   -0.1790    0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6762    0.8820    0.8485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8800    1.9685    1.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5505    1.9312    0.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0509    0.8541    0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614    3.5460   -0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345    2.1757   -1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6808    1.4809    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5378   -0.0697    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833   -2.4698    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9216   -3.3177   -0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0664   -2.9330   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4892   -2.8238    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2089   -1.1842   -2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5427   -2.8644   -0.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977   -1.0159   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7424    0.8867    1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2627    2.8186    1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883    2.7444    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 18-JUN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-13         0                                  
HETATM    1  C   UNK     0      21.679 -17.548   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      23.054 -16.864   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      24.454 -17.506   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.821 -18.991   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.362 -19.065   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.889 -20.221   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.348 -20.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.300 -19.419   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.410 -18.352   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.044 -16.867   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.564 -16.439   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.531 -16.522   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.068 -17.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.751 -18.520   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.900 -19.547   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      24.595 -21.609   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      23.030 -15.323   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      21.679 -14.571   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      24.346 -14.535   0.000  0.00  0.00           O+0
CONECT    1    5    2   12                                                  
CONECT    2    3    1   17                                                  
CONECT    3    4    2   11                                                  
CONECT    4    3    6    8                                                  
CONECT    5    1    7   15                                                  
CONECT    6    4    7   16                                                  
CONECT    7    5    6                                                       
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    3                                                       
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    5                                                       
CONECT   16    6                                                            
CONECT   17    2   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0060676
HETATM    1  N1  UNL     1       2.045   2.707  -1.001  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.754   2.276  -0.579  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.129   3.213  -0.643  1.00  0.00           O  
HETATM    4  N2  UNL     1       0.358   1.023  -0.138  1.00  0.00           N  
HETATM    5  C2  UNL     1       1.282  -0.058  -0.019  1.00  0.00           C  
HETATM    6  C3  UNL     1       2.516   0.445   0.298  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.556  -0.439   0.425  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.329  -1.794   0.236  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.096  -2.264  -0.073  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.001  -1.403  -0.214  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.220  -2.146  -0.476  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.416  -1.430  -0.981  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.498  -2.322  -1.010  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.818  -0.238  -0.218  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.150  -0.179   0.161  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.676   0.882   0.849  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.880   1.968   1.204  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.551   1.931   0.838  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.051   0.854   0.148  1.00  0.00           C  
HETATM   20  H1  UNL     1       2.461   3.546  -0.583  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.534   2.176  -1.723  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.681   1.481   0.493  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.538  -0.070   0.671  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.183  -2.470   0.345  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.922  -3.318  -0.219  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.066  -2.933  -1.257  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.489  -2.824   0.406  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.209  -1.184  -2.056  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.543  -2.864  -0.179  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.798  -1.016  -0.103  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.742   0.887   1.130  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.263   2.819   1.743  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.888   2.744   1.112  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3    3    4
CONECT    4    5   19
CONECT    5    6    6   10
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11
CONECT   11   12   26   27
CONECT   12   13   14   28
CONECT   13   29
CONECT   14   15   15   19
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   32
CONECT   18   19   19   33
END

HMDB0060676
     RDKit          3D
10-Hydroxycarbazepine
 33 35  0  0  0  0  0  0  0  0999 V2000
    2.0448    2.7067   -1.0008 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543    2.2761   -0.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    3.2133   -0.6430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.0227   -0.1381 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817   -0.0583   -0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157    0.4452    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.4390    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -1.7938    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960   -2.2643   -0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0006   -1.4025   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200   -2.1463   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -1.4303   -0.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -2.3225   -1.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8179   -0.2378   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1503   -0.1790    0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6762    0.8820    0.8485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8800    1.9685    1.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5505    1.9312    0.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0509    0.8541    0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614    3.5460   -0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345    2.1757   -1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6808    1.4809    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5378   -0.0697    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833   -2.4698    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9216   -3.3177   -0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0664   -2.9330   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4892   -2.8238    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2089   -1.1842   -2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5427   -2.8644   -0.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977   -1.0159   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7424    0.8867    1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2627    2.8186    1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883    2.7444    1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10,11-Dihydro-10-hydroxycarbamazepine	ChEBI
10-Hydroxycarbamazepine	ChEBI
GP 47779	ChEBI
10-OH-Carbazepine	HMDB
10,11-MHD	MeSH
10,11-Dihydro-10-hydroxy-5H-dibenz(b,F)azepine-5-carboxamide	MeSH
10-Hydroxycarbazepine	ChEBI

Chemical Formula

C₁₅H₁₄N₂O₂

Average Molecular Weight

254.2839

Monoisotopic Molecular Weight

254.105527702

IUPAC Name

9-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide

Traditional Name

9-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide

CAS Registry Number

Not Available

SMILES

NC(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)

InChI Key

BMPDWHIDQYTSHX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Dibenzazepines

Direct Parent

Dibenzazepines

Alternative Parents

Substituents

Dibenzazepine
Azepine
Benzenoid
Isourea
Secondary alcohol
Carboximidic acid derivative
Azacycle
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Imine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carboxamide (CHEBI:701 )
dibenzooxazepine (CHEBI:701 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060676)

Organ

Liver (HMDB: HMDB0060676)
Kidney (HMDB: HMDB0060676)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060676)

Source

Endogenous

Endogenous (HMDB: HMDB0060676)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Carbamazepine Metabolism Pathway (PathBank: SMP0000634)

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	0.55 g/L	ALOGPS
logP	1.26	ALOGPS
logP	1.73	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.1	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.56 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.29 m³·mol⁻¹	ChemAxon
Polarizability	26.31 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	157.149	31661259
DarkChem	[M-H]-	155.346	31661259
DeepCCS	[M-2H]-	184.547	30932474
DeepCCS	[M+Na]+	159.902	30932474
AllCCS	[M+H]+	158.9	32859911
AllCCS	[M+H-H2O]+	154.9	32859911
AllCCS	[M+NH4]+	162.5	32859911
AllCCS	[M+Na]+	163.6	32859911
AllCCS	[M-H]-	161.5	32859911
AllCCS	[M+Na-2H]-	161.0	32859911
AllCCS	[M+HCOO]-	160.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.49 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4727 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.94 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1151.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	267.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	128.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	291.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	362.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	418.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	781.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	266.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1084.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	245.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	354.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	379.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	113.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
10-Hydroxycarbazepine	NC(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C12	3919.8	Standard polar	33892256
10-Hydroxycarbazepine	NC(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C12	2277.2	Standard non polar	33892256
10-Hydroxycarbazepine	NC(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C12	2468.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
10-Hydroxycarbazepine,1TMS,isomer #1	C[Si](C)(C)OC1CC2=CC=CC=C2N(C(N)=O)C2=CC=CC=C21	2351.4	Semi standard non polar	33892256
10-Hydroxycarbazepine,1TMS,isomer #2	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C21	2375.0	Semi standard non polar	33892256
10-Hydroxycarbazepine,2TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C21	2366.2	Semi standard non polar	33892256
10-Hydroxycarbazepine,2TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C21	2396.4	Standard non polar	33892256
10-Hydroxycarbazepine,2TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C21	3076.8	Standard polar	33892256
10-Hydroxycarbazepine,2TMS,isomer #2	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C21)[Si](C)(C)C	2491.6	Semi standard non polar	33892256
10-Hydroxycarbazepine,2TMS,isomer #2	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C21)[Si](C)(C)C	2662.2	Standard non polar	33892256
10-Hydroxycarbazepine,2TMS,isomer #2	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C21)[Si](C)(C)C	3182.7	Standard polar	33892256
10-Hydroxycarbazepine,3TMS,isomer #1	C[Si](C)(C)OC1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2458.6	Semi standard non polar	33892256
10-Hydroxycarbazepine,3TMS,isomer #1	C[Si](C)(C)OC1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2600.2	Standard non polar	33892256
10-Hydroxycarbazepine,3TMS,isomer #1	C[Si](C)(C)OC1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2939.7	Standard polar	33892256
10-Hydroxycarbazepine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2N(C(N)=O)C2=CC=CC=C21	2586.3	Semi standard non polar	33892256
10-Hydroxycarbazepine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C21	2603.9	Semi standard non polar	33892256
10-Hydroxycarbazepine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2737.6	Semi standard non polar	33892256
10-Hydroxycarbazepine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2857.5	Standard non polar	33892256
10-Hydroxycarbazepine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3238.9	Standard polar	33892256
10-Hydroxycarbazepine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2888.4	Semi standard non polar	33892256
10-Hydroxycarbazepine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	3071.8	Standard non polar	33892256
10-Hydroxycarbazepine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(O)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	3267.3	Standard polar	33892256
10-Hydroxycarbazepine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3043.3	Semi standard non polar	33892256
10-Hydroxycarbazepine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3213.1	Standard non polar	33892256
10-Hydroxycarbazepine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3166.9	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Carbamazepine Metabolism Pathway		Not Available

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

102704

KEGG Compound ID

C07493

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Licarbazepine

METLIN ID

Not Available

PubChem Compound

114709

PDB ID

Not Available

ChEBI ID

701

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

Wei CY, Chung WH, Huang HW, Chen YT, Hung SI: Direct interaction between HLA-B and carbamazepine activates T cells in patients with Stevens-Johnson syndrome. J Allergy Clin Immunol. 2012 Jun;129(6):1562-9.e5. doi: 10.1016/j.jaci.2011.12.990. Epub 2012 Feb 8. [PubMed:22322005 ]
Serralheiro A, Alves G, Fortuna A, Rocha M, Falcao A: First HPLC-UV method for rapid and simultaneous quantification of phenobarbital, primidone, phenytoin, carbamazepine, carbamazepine-10,11-epoxide, 10,11-trans-dihydroxy-10,11-dihydrocarbamazepine, lamotrigine, oxcarbazepine and licarbazepine in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Apr 15;925:1-9. doi: 10.1016/j.jchromb.2013.02.026. Epub 2013 Feb 27. [PubMed:23507454 ]
de Jesus Antunes N, Wichert-Ana L, Coelho EB, Della Pasqua O, Alexandre V Jr, Takayanagui OM, Tozatto E, Lanchote VL: Analysis of oxcarbazepine and the 10-hydroxycarbazepine enantiomers in plasma by LC-MS/MS: application in a pharmacokinetic study. Chirality. 2013 Dec;25(12):897-903. doi: 10.1002/chir.22231. Epub 2013 Sep 30. [PubMed:24123382 ]
Ferreira A, Rodrigues M, Oliveira P, Francisco J, Fortuna A, Rosado L, Rosado P, Falcao A, Alves G: Liquid chromatographic assay based on microextraction by packed sorbent for therapeutic drug monitoring of carbamazepine, lamotrigine, oxcarbazepine, phenobarbital, phenytoin and the active metabolites carbamazepine-10,11-epoxide and licarbazepine. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Nov 15;971:20-9. doi: 10.1016/j.jchromb.2014.09.010. Epub 2014 Sep 16. [PubMed:25261836 ]
Kim TH, Reid CA, Petrou S: Oxcarbazepine and its active metabolite, (S)-licarbazepine, exacerbate seizures in a mouse model of genetic generalized epilepsy. Epilepsia. 2015 Jan;56(1):e6-9. doi: 10.1111/epi.12866. Epub 2014 Dec 8. [PubMed:25489632 ]

Showing metabocard for 10-Hydroxycarbazepine (HMDB0060676)

MOL for HMDB0060676 (10-Hydroxycarbazepine)

3D MOL for HMDB0060676 (10-Hydroxycarbazepine)

3D SDF for HMDB0060676 (10-Hydroxycarbazepine)

3D-SDF for HMDB0060676 (10-Hydroxycarbazepine)

PDB for HMDB0060676 (10-Hydroxycarbazepine)

3D PDB for HMDB0060676 (10-Hydroxycarbazepine)

SMILES for HMDB0060676 (10-Hydroxycarbazepine)

INCHI for HMDB0060676 (10-Hydroxycarbazepine)

Structure for HMDB0060676 (10-Hydroxycarbazepine)

3D Structure for HMDB0060676 (10-Hydroxycarbazepine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized