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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 17:39:47 UTC

Update Date

2019-07-23 07:14:47 UTC

HMDB ID

HMDB0060653

Secondary Accession Numbers

HMDB60653

Metabolite Identification

Common Name

3-Hydroxycarbamazepine

Description

3-Hydroxycarbamazepine, also known as 3OHCBZ, 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. 3-Hydroxycarbamazepine is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 3-hydroxycarbamazepine participates in a number of enzymatic reactions. In particular, 3-hydroxycarbamazepine can be biosynthesized from carbamazepine through its interaction with the enzymes cytochrome P450 3A4, cytochrome P450 2B6, and cytochrome P450 3A7. In addition, 3-hydroxycarbamazepine can be converted into 2,3-dihydroxycarbamazepine; which is catalyzed by the enzymes cytochrome P450 2C19, cytochrome P450 3A4, and cytochrome P450 3A5. In humans, 3-hydroxycarbamazepine is involved in carbamazepine metabolism pathway. 3-Hydroxycarbamazepine is a metabolite of carbamazepine.

Structure

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

HMDB0060653
     RDKit          3D
3-Hydroxycarbamazepine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.5298    3.0046   -0.2156 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5673    2.1177   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7304    2.6702    0.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    0.7311    0.0095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462   -0.1336    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4731    0.4307    0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735   -0.2355    1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8733   -1.4360    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971   -1.9887   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -1.3337   -0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7579   -2.0217   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696   -1.8064   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3787   -0.8570   -0.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208   -1.1310   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093   -0.3429    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1768    0.7579    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0719    1.5619    1.4337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8349    1.0580    0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755    0.2673   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254    2.7575   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6835    3.8849    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352    1.3572    1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    0.1620    1.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014   -1.9840    0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357   -2.9335   -0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1965   -2.7559   -2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191   -2.4027   -2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0610   -2.0110   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -0.5833    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444    1.3128    2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    1.8829    1.2481 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 19 13  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
 12 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
M  END

 
  Mrv0541 06181310392D          
 
 19 21  0  0  0  0            999 V2000
   13.9256  -11.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6642  -11.5891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4125  -11.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6046  -12.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7515  -12.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1018  -13.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2761  -13.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3134  -11.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5284  -11.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3544  -12.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9666  -13.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4015  -12.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9848  -12.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7713  -11.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9745  -11.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6969  -10.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9679  -10.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3973  -10.3506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9270  -11.1088    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  2  0  0  0  0
  1  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
  5 11  2  0  0  0  0
  4 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
 15  3  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  9 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060653

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C12

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

> <INCHI_KEY>
QQCFBZCATDIWTH-UHFFFAOYSA-N

> <FORMULA>
C15H12N2O2

> <MOLECULAR_WEIGHT>
252.268

> <EXACT_MASS>
252.089877638

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.05341020083185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.462465064666666

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.958474901447321

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.194977092819505

> <JCHEM_PKA_STRONGEST_BASIC>
-3.846084807651788

> <JCHEM_POLAR_SURFACE_AREA>
66.56

> <JCHEM_REFRACTIVITY>
73.86890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060653
     RDKit          3D
3-Hydroxycarbamazepine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.5298    3.0046   -0.2156 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5673    2.1177   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7304    2.6702    0.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    0.7311    0.0095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462   -0.1336    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4731    0.4307    0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735   -0.2355    1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8733   -1.4360    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971   -1.9887   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -1.3337   -0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7579   -2.0217   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696   -1.8064   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3787   -0.8570   -0.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208   -1.1310   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093   -0.3429    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1768    0.7579    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0719    1.5619    1.4337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8349    1.0580    0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755    0.2673   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254    2.7575   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6835    3.8849    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352    1.3572    1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    0.1620    1.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014   -1.9840    0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357   -2.9335   -0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1965   -2.7559   -2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191   -2.4027   -2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0610   -2.0110   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -0.5833    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444    1.3128    2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    1.8829    1.2481 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 19 13  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
 12 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  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      25.994 -22.309   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      27.373 -21.633   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      28.770 -22.283   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.129 -23.769   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.670 -23.825   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.190 -24.994   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.649 -25.014   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.852 -21.277   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.386 -21.750   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.062 -23.266   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.204 -24.298   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.616 -24.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.705 -23.079   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.306 -21.591   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.819 -21.193   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.434 -20.094   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      26.073 -19.327   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      28.742 -19.321   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      22.264 -20.736   0.000  0.00  0.00           O+0
CONECT    1    5    2    8                                                  
CONECT    2    3    1   16                                                  
CONECT    3    4    2   15                                                  
CONECT    4    3    6   12                                                  
CONECT    5    1    7   11                                                  
CONECT    6    4    7                                                       
CONECT    7    5    6                                                       
CONECT    8    1    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    4   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    3                                                       
CONECT   16    2   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    9                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0060653
HETATM    1  N1  UNL     1      -0.530   3.005  -0.216  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.567   2.118  -0.048  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.730   2.670   0.035  1.00  0.00           O  
HETATM    4  N2  UNL     1       0.381   0.731   0.010  1.00  0.00           N  
HETATM    5  C2  UNL     1       1.546  -0.134   0.099  1.00  0.00           C  
HETATM    6  C3  UNL     1       2.473   0.431   0.915  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.673  -0.236   1.098  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.873  -1.436   0.448  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.897  -1.989  -0.382  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.693  -1.334  -0.575  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.758  -2.022  -1.452  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.570  -1.806  -1.524  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.379  -0.857  -0.763  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.721  -1.131  -0.716  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.609  -0.343   0.001  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.177   0.758   0.704  1.00  0.00           C  
HETATM   17  O2  UNL     1      -4.072   1.562   1.434  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.835   1.058   0.677  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.976   0.267  -0.041  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.225   2.758  -0.940  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.683   3.885   0.323  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.235   1.357   1.412  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.445   0.162   1.728  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.801  -1.984   0.569  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.036  -2.934  -0.902  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.197  -2.756  -2.079  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.119  -2.403  -2.224  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.061  -2.011  -1.278  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.674  -0.583   0.021  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.244   1.313   2.418  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.432   1.883   1.248  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   12   26
CONECT   12   13   27
CONECT   13   14   14   19
CONECT   14   15   28
CONECT   15   16   16   29
CONECT   16   17   18
CONECT   17   30
CONECT   18   19   19   31
END

HMDB0060653
     RDKit          3D
3-Hydroxycarbamazepine
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.5298    3.0046   -0.2156 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5673    2.1177   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7304    2.6702    0.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    0.7311    0.0095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462   -0.1336    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4731    0.4307    0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735   -0.2355    1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8733   -1.4360    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971   -1.9887   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932   -1.3337   -0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7579   -2.0217   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696   -1.8064   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3787   -0.8570   -0.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208   -1.1310   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093   -0.3429    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1768    0.7579    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0719    1.5619    1.4337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8349    1.0580    0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755    0.2673   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254    2.7575   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6835    3.8849    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352    1.3572    1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    0.1620    1.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014   -1.9840    0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357   -2.9335   -0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1965   -2.7559   -2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191   -2.4027   -2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0610   -2.0110   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -0.5833    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444    1.3128    2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    1.8829    1.2481 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 19 13  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
 12 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3OHCBZ	HMDB

Chemical Formula

C₁₅H₁₂N₂O₂

Average Molecular Weight

252.268

Monoisotopic Molecular Weight

252.089877638

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C12

InChI Identifier

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

InChI Key

QQCFBZCATDIWTH-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
1-hydroxy-2-unsubstituted benzenoid
Azepine
Benzenoid
Isourea
Azacycle
Carboximidic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzooxazepine (CHEBI:80597 )

Ontology

Not Available

Liver (HMDB: HMDB0060653)
Kidney (HMDB: HMDB0060653)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060653)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060653)

Cellular substructure

Cytoplasm (HMDB: HMDB0060653)
Membrane (HMDB: HMDB0060653)

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	0.11 g/L	ALOGPS
logP	2.25	ALOGPS
logP	2.46	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-3.8	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	73.87 m³·mol⁻¹	ChemAxon
Polarizability	26.05 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]+	157.942	31661259
DarkChem	[M-H]-	155.62	31661259
DeepCCS	[M-2H]-	184.799	30932474
DeepCCS	[M+Na]+	160.163	30932474
AllCCS	[M+H]+	157.5	32859911
AllCCS	[M+H-H2O]+	153.5	32859911
AllCCS	[M+NH4]+	161.2	32859911
AllCCS	[M+Na]+	162.3	32859911
AllCCS	[M-H]-	159.5	32859911
AllCCS	[M+Na-2H]-	158.8	32859911
AllCCS	[M+HCOO]-	158.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxycarbamazepine	NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C12	4178.7	Standard polar	33892256
3-Hydroxycarbamazepine	NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C12	2447.7	Standard non polar	33892256
3-Hydroxycarbamazepine	NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C12	2679.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxycarbamazepine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(N)=O)C2=C1	2524.7	Semi standard non polar	33892256
3-Hydroxycarbamazepine,1TMS,isomer #2	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21	2451.8	Semi standard non polar	33892256
3-Hydroxycarbamazepine,2TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C)C=C21	2486.9	Semi standard non polar	33892256
3-Hydroxycarbamazepine,2TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C)C=C21	2501.2	Standard non polar	33892256
3-Hydroxycarbamazepine,2TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C)C=C21	3432.2	Standard polar	33892256
3-Hydroxycarbamazepine,2TMS,isomer #2	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C	2542.2	Semi standard non polar	33892256
3-Hydroxycarbamazepine,2TMS,isomer #2	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C	2730.5	Standard non polar	33892256
3-Hydroxycarbamazepine,2TMS,isomer #2	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C	3624.0	Standard polar	33892256
3-Hydroxycarbamazepine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	2550.8	Semi standard non polar	33892256
3-Hydroxycarbamazepine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	2762.1	Standard non polar	33892256
3-Hydroxycarbamazepine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1	3327.2	Standard polar	33892256
3-Hydroxycarbamazepine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(N)=O)C2=C1	2776.0	Semi standard non polar	33892256
3-Hydroxycarbamazepine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21	2670.2	Semi standard non polar	33892256
3-Hydroxycarbamazepine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21	2907.2	Semi standard non polar	33892256
3-Hydroxycarbamazepine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21	2887.7	Standard non polar	33892256
3-Hydroxycarbamazepine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21	3588.8	Standard polar	33892256
3-Hydroxycarbamazepine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C(C)(C)C	2958.1	Semi standard non polar	33892256
3-Hydroxycarbamazepine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C(C)(C)C	3045.6	Standard non polar	33892256
3-Hydroxycarbamazepine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C(C)(C)C	3647.9	Standard polar	33892256
3-Hydroxycarbamazepine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3188.6	Semi standard non polar	33892256
3-Hydroxycarbamazepine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3289.1	Standard non polar	33892256
3-Hydroxycarbamazepine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3541.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxycarbamazepine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1190000000-a63cd184d192b469a0bb	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxycarbamazepine GC-MS (1 TMS) - 70eV, Positive	splash10-05gi-4091000000-aa4e3a154aab49a9f90c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxycarbamazepine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 10V, Positive-QTOF	splash10-0udr-0090000000-01f6142623d495374520	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 20V, Positive-QTOF	splash10-03dr-0090000000-83afddda616892de1708	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 40V, Positive-QTOF	splash10-0a5c-0970000000-df18c252a4ebb6e19782	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 10V, Negative-QTOF	splash10-0pbc-5090000000-b4cf89fc59b9af7e7aac	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 20V, Negative-QTOF	splash10-0a4i-2090000000-14c0e5b2cb42384e554d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 40V, Negative-QTOF	splash10-0006-9220000000-5bb7e2feabf45d211373	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 10V, Positive-QTOF	splash10-0udi-0090000000-068391fc308918509fc3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 20V, Positive-QTOF	splash10-08fr-0090000000-08755f0ae6819797e32e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 40V, Positive-QTOF	splash10-0a4i-0790000000-41511f8d7b33a31c1ea9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 10V, Negative-QTOF	splash10-0udi-0090000000-229652fa3e4351b39559	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 20V, Negative-QTOF	splash10-0a4i-0090000000-9f12ac38c8faae87e87f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 40V, Negative-QTOF	splash10-0a4i-0090000000-296de1c6f0c6cab3a7f1	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

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

C16602

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135290

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3-Hydroxycarbamazepine (HMDB0060653)

MOL for HMDB0060653 (3-Hydroxycarbamazepine)

3D MOL for HMDB0060653 (3-Hydroxycarbamazepine)

3D SDF for HMDB0060653 (3-Hydroxycarbamazepine)

3D-SDF for HMDB0060653 (3-Hydroxycarbamazepine)

PDB for HMDB0060653 (3-Hydroxycarbamazepine)

3D PDB for HMDB0060653 (3-Hydroxycarbamazepine)

SMILES for HMDB0060653 (3-Hydroxycarbamazepine)

INCHI for HMDB0060653 (3-Hydroxycarbamazepine)

Structure for HMDB0060653 (3-Hydroxycarbamazepine)

3D Structure for HMDB0060653 (3-Hydroxycarbamazepine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra