Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

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, 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. 10-Hydroxycarbazepine is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, 10-hydroxycarbazepine is involved in carbamazepine metabolism pathway.

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-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

Not Available

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

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060676)

Excreta

Biofluid or Excreta

Urine (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 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

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Hydroxycarbazepine GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fu-1790000000-cacb3a5de807288d3fd9	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Hydroxycarbazepine GC-MS (1 TMS) - 70eV, Positive	splash10-023c-8092000000-7a3da09410d5d9b659b2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Hydroxycarbazepine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Hydroxycarbazepine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 10-Hydroxycarbazepine 40V, Positive-QTOF	splash10-0006-0900000000-ec01a06031aed2410428	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 10-Hydroxycarbazepine 30V, Positive-QTOF	splash10-0006-0900000000-f622fc29eb9ed2d3a8c4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 10-Hydroxycarbazepine 10V, Positive-QTOF	splash10-000i-0190000000-9fa2a6c95bf4672c4cc5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 10-Hydroxycarbazepine 20V, Positive-QTOF	splash10-0006-0930000000-9b4b94f63548dc7d4da6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 10-Hydroxycarbazepine 50V, Positive-QTOF	splash10-0006-0900000000-caefef2d89de5b09f10c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 10V, Positive-QTOF	splash10-052r-0090000000-e1ffdac8bf93f4c80d2f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 20V, Positive-QTOF	splash10-000l-0390000000-c7cd4fed8e7d6a26937e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 40V, Positive-QTOF	splash10-0006-9640000000-eb15569c6905d8665c03	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 10V, Negative-QTOF	splash10-0006-6290000000-a1b28c6ef7e673d18d4c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 20V, Negative-QTOF	splash10-01ox-4790000000-8ce70946b6b8aa2e2733	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 40V, Negative-QTOF	splash10-0006-9300000000-f844d0a5bb22313f7264	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 10V, Positive-QTOF	splash10-000i-0290000000-96639d3da4148d57cbf0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 20V, Positive-QTOF	splash10-0006-0910000000-596360dddae8d723db0a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 40V, Positive-QTOF	splash10-0006-1920000000-27a9ba9eee1be04e53d3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 10V, Negative-QTOF	splash10-0udi-0190000000-25922792ee30a221c24a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 20V, Negative-QTOF	splash10-0006-0960000000-dd2845e3357e337f2ef7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxycarbazepine 40V, Negative-QTOF	splash10-0a4l-1690000000-22d1733ae6d567d7e748	2021-10-12	Wishart Lab	View Spectrum

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

Not Available

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 Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra