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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014914

Secondary Accession Numbers

HMDB14914

Metabolite Identification

Common Name

Oxcarbazepine

Description

Oxcarbazepine is structurally a derivative of carbamazepine, adding an extra oxygen atom to the benzylcarboxamide group. This difference helps reduce the impact on the liver of metabolizing the drug, and also prevents the serious forms of anemia occasionally associated with carbamazepine. Aside from this reduction in side effects, it is thought to have the same mechanism as carbamazepine - sodium channel inhibition - and is generally used to treat partial seizures in epileptic children and adults.

Structure

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

HMDB0014914
     RDKit          3D
Oxcarbazepine
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.5902    3.1965   -0.3436 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4681    2.2179   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    2.6567   -0.4043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    0.8520    0.0018 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    0.3936    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324    1.2847    0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1712    1.0391    1.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7032   -0.1263    0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9287   -1.0099   -0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903   -0.7744   -0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291   -1.8816   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393   -2.0488   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8534   -3.0852   -1.6293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097   -1.2660   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7265   -1.9301   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8238   -1.3343    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7164   -0.0561    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4979    0.6215    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209    0.0043    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    4.0689    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706    2.9169   -0.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489    2.1569    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360    1.7571    1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7569   -0.3046    0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340   -1.9081   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -2.8307   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -1.8708   -2.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -2.9339   -0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7676   -1.8430    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5363    0.4397    1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    1.5978    1.0262 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  2  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
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

776
  Mrv0541 02231214592D          

 19 21  0  0  0  0            999 V2000
    3.1279    2.0639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1816   -1.5728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8676   -0.3848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5535   -1.5728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574    0.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5812   -0.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2636    1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1539   -0.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9777    0.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4715    1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5419    0.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1772   -0.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -0.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1932    0.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8676   -1.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1510    0.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9674   -0.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677   -0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    0.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 15  2  0  0  0  0
  3  6  1  0  0  0  0
  3  8  1  0  0  0  0
  3 15  1  0  0  0  0
  4 15  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  2  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  0  0  0  0
 16 17  2  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014914

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)

> <INCHI_KEY>
CTRLABGOLIVAIY-UHFFFAOYSA-N

> <FORMULA>
C15H12N2O2

> <MOLECULAR_WEIGHT>
252.268

> <EXACT_MASS>
252.089877638

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.719636172454756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
1.8181766893333329

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.964849395589898

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.921004832249956

> <JCHEM_PKA_STRONGEST_BASIC>
-4.297000314867087

> <JCHEM_POLAR_SURFACE_AREA>
63.400000000000006

> <JCHEM_REFRACTIVITY>
71.55790000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxcarbazepine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014914
     RDKit          3D
Oxcarbazepine
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.5902    3.1965   -0.3436 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4681    2.2179   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    2.6567   -0.4043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    0.8520    0.0018 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    0.3936    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324    1.2847    0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1712    1.0391    1.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7032   -0.1263    0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9287   -1.0099   -0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903   -0.7744   -0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291   -1.8816   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393   -2.0488   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8534   -3.0852   -1.6293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097   -1.2660   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7265   -1.9301   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8238   -1.3343    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7164   -0.0561    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4979    0.6215    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209    0.0043    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    4.0689    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706    2.9169   -0.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489    2.1569    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360    1.7571    1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7569   -0.3046    0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340   -1.9081   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -2.8307   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -1.8708   -2.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -2.9339   -0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7676   -1.8430    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5363    0.4397    1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    1.5978    1.0262 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  2  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
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 776                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.839   3.853   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.939  -2.936   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.220  -0.718   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.500  -2.936   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.880   1.365   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.552  -0.077   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.959   2.521   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.887  -0.077   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.558   1.365   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.480   2.521   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.345   1.841   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.664  -1.141   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.775  -1.141   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.094   1.841   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.220  -2.197   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.482   0.802   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.139  -0.699   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.300  -0.699   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.957   0.802   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   15                                                            
CONECT    3    6    8   15                                                  
CONECT    4   15                                                            
CONECT    5    6    7   11                                                  
CONECT    6    3    5   12                                                  
CONECT    7    5   10                                                       
CONECT    8    3    9   13                                                  
CONECT    9    8   10   14                                                  
CONECT   10    1    7    9                                                  
CONECT   11    5   16                                                       
CONECT   12    6   17                                                       
CONECT   13    8   18                                                       
CONECT   14    9   19                                                       
CONECT   15    2    3    4                                                  
CONECT   16   11   17                                                       
CONECT   17   12   16                                                       
CONECT   18   13   19                                                       
CONECT   19   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0014914
HETATM    1  N1  UNL     1       0.590   3.196  -0.344  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.468   2.218  -0.245  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.645   2.657  -0.404  1.00  0.00           O  
HETATM    4  N2  UNL     1      -0.260   0.852   0.002  1.00  0.00           N  
HETATM    5  C2  UNL     1       1.092   0.394   0.166  1.00  0.00           C  
HETATM    6  C3  UNL     1       1.832   1.285   0.899  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.171   1.039   1.154  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.703  -0.126   0.641  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.929  -1.010  -0.095  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.590  -0.774  -0.356  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.029  -1.882  -1.141  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.439  -2.049  -1.055  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.853  -3.085  -1.629  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.510  -1.266  -0.444  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.727  -1.930  -0.340  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.824  -1.334   0.241  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.716  -0.056   0.729  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.498   0.622   0.631  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.421   0.004   0.045  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.466   4.069   0.190  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.371   2.917  -0.949  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.349   2.157   1.295  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.736   1.757   1.733  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.757  -0.305   0.851  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.434  -1.908  -0.461  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.472  -2.831  -0.716  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.307  -1.871  -2.209  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.820  -2.934  -0.720  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.768  -1.843   0.323  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.536   0.440   1.184  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.343   1.598   1.026  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   13   14
CONECT   14   15   15   19
CONECT   15   16   28
CONECT   16   17   17   29
CONECT   17   18   30
CONECT   18   19   19   31
END

HMDB0014914
     RDKit          3D
Oxcarbazepine
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.5902    3.1965   -0.3436 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4681    2.2179   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    2.6567   -0.4043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    0.8520    0.0018 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    0.3936    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324    1.2847    0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1712    1.0391    1.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7032   -0.1263    0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9287   -1.0099   -0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903   -0.7744   -0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291   -1.8816   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393   -2.0488   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8534   -3.0852   -1.6293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5097   -1.2660   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7265   -1.9301   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8238   -1.3343    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7164   -0.0561    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4979    0.6215    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209    0.0043    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    4.0689    0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706    2.9169   -0.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489    2.1569    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360    1.7571    1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7569   -0.3046    0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340   -1.9081   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -2.8307   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -1.8708   -2.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -2.9339   -0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7676   -1.8430    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5363    0.4397    1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    1.5978    1.0262 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  2  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
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10,11-Dihydro-10-oxo-5H-dibenz(b,F)azepine-5-carboxamide	ChEBI
Oxcarbazepina	ChEBI
Oxcarbazepinum	ChEBI
Oxtellar	Kegg
Trileptal	Kegg
Oxcarbamazepine	HMDB
Desitin brand OF oxcarbazepine	HMDB
Novartis brand OF oxcarbazepine	HMDB
Timox	HMDB

Chemical Formula

C₁₅H₁₂N₂O₂

Average Molecular Weight

252.268

Monoisotopic Molecular Weight

252.089877638

IUPAC Name

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

Traditional Name

oxcarbazepine

CAS Registry Number

28721-07-5

SMILES

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

InChI Identifier

InChI=1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)

InChI Key

CTRLABGOLIVAIY-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
Aryl ketone
Aryl alkyl ketone
Azepine
Benzenoid
Vinylogous amide
Isourea
Ketone
Carboximidic acid derivative
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Imine
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:7824 )
dibenzoazepine (CHEBI:7824 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014914)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Carbamazepine Metabolism Pathway (PathBank: SMP0000634)

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

anticonvulsant (HMDB: HMDB0014914)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	215.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.16 g/L	Not Available
LogP	1.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	153.8	30932474
[M+H]+	Not Available	152.743	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001027

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	1.76	ALOGPS
logP	1.82	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.92	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.4 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.56 m³·mol⁻¹	ChemAxon
Polarizability	25.72 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]+	157.068	31661259
DarkChem	[M-H]-	155.614	31661259
DeepCCS	[M-2H]-	183.82	30932474
DeepCCS	[M+Na]+	159.079	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	152.8	32859911
AllCCS	[M+NH4]+	160.5	32859911
AllCCS	[M+Na]+	161.6	32859911
AllCCS	[M-H]-	159.1	32859911
AllCCS	[M+Na-2H]-	158.4	32859911
AllCCS	[M+HCOO]-	157.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxcarbazepine	NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C12	3826.6	Standard polar	33892256
Oxcarbazepine	NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C12	2274.4	Standard non polar	33892256
Oxcarbazepine	NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C12	2474.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oxcarbazepine,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21	2320.1	Semi standard non polar	33892256
Oxcarbazepine,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21	2392.8	Standard non polar	33892256
Oxcarbazepine,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21	3233.0	Standard polar	33892256
Oxcarbazepine,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21)[Si](C)(C)C	2401.5	Semi standard non polar	33892256
Oxcarbazepine,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21)[Si](C)(C)C	2609.6	Standard non polar	33892256
Oxcarbazepine,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21)[Si](C)(C)C	3146.5	Standard polar	33892256
Oxcarbazepine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21	2531.4	Semi standard non polar	33892256
Oxcarbazepine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21	2613.4	Standard non polar	33892256
Oxcarbazepine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21	3337.6	Standard polar	33892256
Oxcarbazepine,2TBDMS,isomer #1	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	2798.1	Semi standard non polar	33892256
Oxcarbazepine,2TBDMS,isomer #1	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	2995.0	Standard non polar	33892256
Oxcarbazepine,2TBDMS,isomer #1	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	3240.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oxcarbazepine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3490000000-e819f3deb2b8c87b4232	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxcarbazepine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxcarbazepine 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 - Oxcarbazepine LC-ESI-qTof , Positive-QTOF	splash10-0f8i-1790000000-cd62672e7fa7c39f0be1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxcarbazepine LC-ESI-qTof , Positive-QTOF	splash10-0kar-0690000000-cbc95a31913165d691a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxcarbazepine LC-ESI-qTof , Positive-QTOF	splash10-001i-2910000000-d1242af6b8148ffac3a9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxcarbazepine LC-ESI-QFT , negative-QTOF	splash10-0pb9-0090000000-46d01e1171f998679d03	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxcarbazepine , positive-QTOF	splash10-0f8i-1790000000-cd62672e7fa7c39f0be1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxcarbazepine , positive-QTOF	splash10-0kar-0690000000-cbc95a31913165d691a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxcarbazepine , positive-QTOF	splash10-001i-2910000000-d1242af6b8148ffac3a9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxcarbazepine 35V, Positive-QTOF	splash10-053r-0790000000-1538838440ac9de0764b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxcarbazepine 35V, Negative-QTOF	splash10-0pb9-0090000000-7003f419893f7314126c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 10V, Positive-QTOF	splash10-0udi-0090000000-fe8a28b607ec5dddd195	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 20V, Positive-QTOF	splash10-0ik9-0090000000-4536652e48c7784201c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 40V, Positive-QTOF	splash10-0006-3950000000-4981fd5d2c607be060c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 10V, Negative-QTOF	splash10-0pbc-5090000000-5d40809535b419b6b2de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 20V, Negative-QTOF	splash10-0a4i-2090000000-d016d9db20537c45eaae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 40V, Negative-QTOF	splash10-0006-9220000000-4e53a0698392fe26965d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 10V, Positive-QTOF	splash10-0udi-0090000000-d2b279fe7e26771148aa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 20V, Positive-QTOF	splash10-03di-0090000000-3f6fe55807c0254e0b44	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 40V, Positive-QTOF	splash10-0a59-0790000000-ca89b030e1d26b804a84	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 10V, Negative-QTOF	splash10-0udi-0090000000-229652fa3e4351b39559	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 20V, Negative-QTOF	splash10-0a4i-0090000000-9f12ac38c8faae87e87f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxcarbazepine 40V, Negative-QTOF	splash10-0a4i-0090000000-296de1c6f0c6cab3a7f1	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB00776	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00776	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00776

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31608

KEGG Compound ID

C07492

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxcarbazepine

METLIN ID

Not Available

PubChem Compound

34312

PDB ID

Not Available

ChEBI ID

7824

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

Mazza M, Della Marca G, Di Nicola M, Martinotti G, Pozzi G, Janiri L, Bria P, Mazza S: Oxcarbazepine improves mood in patients with epilepsy. Epilepsy Behav. 2007 May;10(3):397-401. Epub 2007 Feb 14. [PubMed:17300991 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Sodium channel protein type 5 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Vohora D, Saraogi P, Yazdani MA, Bhowmik M, Khanam R, Pillai KK: Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs. Drugs Today (Barc). 2010 Apr;46(4):265-77. doi: 10.1358/dot.2010.46.4.1445795. [PubMed:20502724 ]

Showing metabocard for Oxcarbazepine (HMDB0014914)

MOL for HMDB0014914 (Oxcarbazepine)

3D MOL for HMDB0014914 (Oxcarbazepine)

3D SDF for HMDB0014914 (Oxcarbazepine)

3D-SDF for HMDB0014914 (Oxcarbazepine)

PDB for HMDB0014914 (Oxcarbazepine)

3D PDB for HMDB0014914 (Oxcarbazepine)

SMILES for HMDB0014914 (Oxcarbazepine)

INCHI for HMDB0014914 (Oxcarbazepine)

Structure for HMDB0014914 (Oxcarbazepine)

3D Structure for HMDB0014914 (Oxcarbazepine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References