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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 16:53:48 UTC

Update Date

2019-07-23 07:14:36 UTC

HMDB ID

HMDB0060566

Secondary Accession Numbers

HMDB60566

Metabolite Identification

Common Name

Carbamazepine-O-quinone

Description

Carbamazepine-O-quinone 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. Carbamazepine-O-quinone is a strong basic compound (based on its pKa). In humans, carbamazepine-O-quinone is involved in carbamazepine metabolism pathway.

Structure

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

HMDB0060566
     RDKit          3D
Carbamazepine-O-quinone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.2774    2.8989    1.0160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633    2.1541   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151    2.6942   -1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1028    0.7544   -0.0199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1893   -0.0001    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    0.7173    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5686    0.1060    0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5889    0.8341    0.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062   -1.2715    0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7260   -1.8563    0.8404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -2.0286    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2603   -1.4498    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206   -2.3550    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354   -2.1117    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -0.8891   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029   -1.0459   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8906    0.0777   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3499    1.3422   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0003    1.4858   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1777    0.3839   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091    2.4238    1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    2.1826   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611    1.8040    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253   -3.1080    0.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5558   -3.3916    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788   -2.9527    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5389   -2.0397   -0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502   -0.0314   -0.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9241    2.2362   -0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265    2.4359   -0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 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
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  4  1  0
 12  5  1  0
 20 15  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
 11 24  1  0
 13 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
M  END


  Mrv0541 06151309532D          

 20 22  0  0  0  0            999 V2000
    6.1237   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    0.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912    0.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -1.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892   -2.1078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -0.8703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6953    0.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625   -1.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -2.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  9  3  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 16 15  2  0  0  0  0
 17 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  2  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060566

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H10N2O3/c16-15(20)17-11-4-2-1-3-9(11)5-6-10-7-13(18)14(19)8-12(10)17/h1-8H,(H2,16,20)

> <INCHI_KEY>
GONNJNYLBPEEPH-UHFFFAOYSA-N

> <FORMULA>
C15H10N2O3

> <MOLECULAR_WEIGHT>
266.2515

> <EXACT_MASS>
266.069142196

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.5859440992292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13,14-dioxo-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11-hexaene-2-carboximidic acid

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
2.1858725823333325

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.802286055736634

> <JCHEM_PKA_STRONGEST_BASIC>
3.812352073534625

> <JCHEM_POLAR_SURFACE_AREA>
81.46000000000001

> <JCHEM_REFRACTIVITY>
88.21669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carbamazepine-o-quinone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060566
     RDKit          3D
Carbamazepine-O-quinone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.2774    2.8989    1.0160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633    2.1541   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151    2.6942   -1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1028    0.7544   -0.0199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1893   -0.0001    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    0.7173    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5686    0.1060    0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5889    0.8341    0.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062   -1.2715    0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7260   -1.8563    0.8404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -2.0286    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2603   -1.4498    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206   -2.3550    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354   -2.1117    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -0.8891   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029   -1.0459   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8906    0.0777   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3499    1.3422   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0003    1.4858   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1777    0.3839   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091    2.4238    1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    2.1826   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611    1.8040    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253   -3.1080    0.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5558   -3.3916    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788   -2.9527    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5389   -2.0397   -0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502   -0.0314   -0.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9241    2.2362   -0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265    2.4359   -0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 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
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  4  1  0
 12  5  1  0
 20 15  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
 11 24  1  0
 13 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      11.431  -0.049   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.088  -1.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.302   0.999   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.617  -2.004   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.870   1.749   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.330   1.749   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.898   0.999   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.584  -2.004   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.830   0.545   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.370   0.545   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.488  -0.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.713  -0.956   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.770  -0.049   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.112  -1.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.100  -3.165   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.767  -3.935   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       7.100  -1.625   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       1.298   0.405   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.983  -2.597   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.434  -3.935   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    9                                                       
CONECT    4    2   11                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7   10   13                                                       
CONECT    8   12   14                                                       
CONECT    9    3    5   11                                                  
CONECT   10    6    7   12                                                  
CONECT   11    4    9   17                                                  
CONECT   12    8   10   17                                                  
CONECT   13    7   14   18                                                  
CONECT   14    8   13   19                                                  
CONECT   15   16   17   20                                                  
CONECT   16   15                                                            
CONECT   17   11   12   15                                                  
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0060566
HETATM    1  N1  UNL     1      -0.277   2.899   1.016  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.363   2.154  -0.054  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.715   2.694  -1.285  1.00  0.00           O  
HETATM    4  N2  UNL     1      -0.103   0.754  -0.020  1.00  0.00           N  
HETATM    5  C2  UNL     1      -1.189  -0.000   0.188  1.00  0.00           C  
HETATM    6  C3  UNL     1      -2.353   0.717   0.348  1.00  0.00           C  
HETATM    7  C4  UNL     1      -3.569   0.106   0.571  1.00  0.00           C  
HETATM    8  O2  UNL     1      -4.589   0.834   0.707  1.00  0.00           O  
HETATM    9  C5  UNL     1      -3.606  -1.271   0.634  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.726  -1.856   0.840  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.477  -2.029   0.482  1.00  0.00           C  
HETATM   12  C7  UNL     1      -1.260  -1.450   0.260  1.00  0.00           C  
HETATM   13  C8  UNL     1      -0.221  -2.355   0.128  1.00  0.00           C  
HETATM   14  C9  UNL     1       1.135  -2.112   0.063  1.00  0.00           C  
HETATM   15  C10 UNL     1       1.736  -0.889  -0.162  1.00  0.00           C  
HETATM   16  C11 UNL     1       3.103  -1.046  -0.377  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.891   0.078  -0.624  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.350   1.342  -0.662  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.000   1.486  -0.449  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.178   0.384  -0.198  1.00  0.00           C  
HETATM   21  H1  UNL     1      -0.009   2.424   1.900  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.311   2.183  -1.944  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.261   1.804   0.288  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.525  -3.108   0.534  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.556  -3.392   0.071  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.779  -2.953   0.201  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.539  -2.040  -0.349  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.950  -0.031  -0.791  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.924   2.236  -0.849  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.527   2.436  -0.466  1.00  0.00           H  
CONECT    1    2    2   21
CONECT    2    3    4
CONECT    3   22
CONECT    4    5   20
CONECT    5    6    6   12
CONECT    6    7   23
CONECT    7    8    8    9
CONECT    9   10   10   11
CONECT   11   12   12   24
CONECT   12   13
CONECT   13   14   14   25
CONECT   14   15   26
CONECT   15   16   16   20
CONECT   16   17   27
CONECT   17   18   18   28
CONECT   18   19   29
CONECT   19   20   20   30
END

HMDB0060566
     RDKit          3D
Carbamazepine-O-quinone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.2774    2.8989    1.0160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633    2.1541   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7151    2.6942   -1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1028    0.7544   -0.0199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1893   -0.0001    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    0.7173    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5686    0.1060    0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5889    0.8341    0.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062   -1.2715    0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7260   -1.8563    0.8404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -2.0286    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2603   -1.4498    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206   -2.3550    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354   -2.1117    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -0.8891   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029   -1.0459   -0.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8906    0.0777   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3499    1.3422   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0003    1.4858   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1777    0.3839   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091    2.4238    1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    2.1826   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611    1.8040    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253   -3.1080    0.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5558   -3.3916    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788   -2.9527    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5389   -2.0397   -0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502   -0.0314   -0.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9241    2.2362   -0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265    2.4359   -0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 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
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  4  1  0
 12  5  1  0
 20 15  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
 11 24  1  0
 13 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀N₂O₃

Average Molecular Weight

266.2515

Monoisotopic Molecular Weight

266.069142196

IUPAC Name

13,14-dioxo-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11-hexaene-2-carboximidic acid

Traditional Name

carbamazepine-o-quinone

CAS Registry Number

Not Available

SMILES

OC(=N)N1C2=CC=CC=C2C=CC2=CC(=O)C(=O)C=C12

InChI Identifier

InChI=1S/C15H10N2O3/c16-15(20)17-11-4-2-1-3-9(11)5-6-10-7-13(18)14(19)8-12(10)17/h1-8H,(H2,16,20)

InChI Key

GONNJNYLBPEEPH-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
Heteroaromatic compound
Vinylogous amide
Carbonic acid derivative
Urea
Cyclic ketone
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzooxazepine (CHEBI:80601 )

Ontology

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	0.082 g/L	ALOGPS
logP	1.44	ALOGPS
logP	2.19	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	3.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.22 m³·mol⁻¹	ChemAxon
Polarizability	26.59 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]+	162.353	31661259
DarkChem	[M-H]-	159.959	31661259
DeepCCS	[M-2H]-	192.743	30932474
DeepCCS	[M+Na]+	168.307	30932474
AllCCS	[M+H]+	158.3	32859911
AllCCS	[M+H-H2O]+	154.4	32859911
AllCCS	[M+NH4]+	162.0	32859911
AllCCS	[M+Na]+	163.0	32859911
AllCCS	[M-H]-	161.1	32859911
AllCCS	[M+Na-2H]-	160.3	32859911
AllCCS	[M+HCOO]-	159.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.95 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8038 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1633.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	336.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	85.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	300.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	304.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	736.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	642.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	220.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	756.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	242.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	690.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	450.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	54.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carbamazepine-O-quinone	OC(=N)N1C2=CC=CC=C2C=CC2=CC(=O)C(=O)C=C12	3832.8	Standard polar	33892256
Carbamazepine-O-quinone	OC(=N)N1C2=CC=CC=C2C=CC2=CC(=O)C(=O)C=C12	2492.8	Standard non polar	33892256
Carbamazepine-O-quinone	OC(=N)N1C2=CC=CC=C2C=CC2=CC(=O)C(=O)C=C12	3113.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carbamazepine-O-quinone,1TMS,isomer #1	C[Si](C)(C)OC(=N)N1C2=CC(=O)C(=O)C=C2C=CC2=CC=CC=C21	2823.1	Semi standard non polar	33892256
Carbamazepine-O-quinone,1TMS,isomer #2	C[Si](C)(C)N=C(O)N1C2=CC(=O)C(=O)C=C2C=CC2=CC=CC=C21	2707.0	Semi standard non polar	33892256
Carbamazepine-O-quinone,2TMS,isomer #1	C[Si](C)(C)N=C(O[Si](C)(C)C)N1C2=CC(=O)C(=O)C=C2C=CC2=CC=CC=C21	2810.8	Semi standard non polar	33892256
Carbamazepine-O-quinone,2TMS,isomer #1	C[Si](C)(C)N=C(O[Si](C)(C)C)N1C2=CC(=O)C(=O)C=C2C=CC2=CC=CC=C21	2807.7	Standard non polar	33892256
Carbamazepine-O-quinone,2TMS,isomer #1	C[Si](C)(C)N=C(O[Si](C)(C)C)N1C2=CC(=O)C(=O)C=C2C=CC2=CC=CC=C21	3473.4	Standard polar	33892256
Carbamazepine-O-quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=N)N1C2=CC(=O)C(=O)C=C2C=CC2=CC=CC=C21	3070.8	Semi standard non polar	33892256
Carbamazepine-O-quinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(O)N1C2=CC(=O)C(=O)C=C2C=CC2=CC=CC=C21	2999.8	Semi standard non polar	33892256
Carbamazepine-O-quinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)N1C2=CC(=O)C(=O)C=C2C=CC2=CC=CC=C21	3233.8	Semi standard non polar	33892256
Carbamazepine-O-quinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)N1C2=CC(=O)C(=O)C=C2C=CC2=CC=CC=C21	3208.8	Standard non polar	33892256
Carbamazepine-O-quinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)N1C2=CC(=O)C(=O)C=C2C=CC2=CC=CC=C21	3541.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Carbamazepine-O-quinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-2490000000-b8f18d208ea4d361c5eb	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carbamazepine-O-quinone GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9385000000-9b0eee273cff432b2371	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carbamazepine-O-quinone 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 - Carbamazepine-O-quinone 10V, Positive-QTOF	splash10-014i-0090000000-e978526feefd69b31093	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 20V, Positive-QTOF	splash10-00di-0090000000-22c7d21cb2e75bd9cb0f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 40V, Positive-QTOF	splash10-0075-0970000000-8c1674e8ea9f27f84d7a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 10V, Negative-QTOF	splash10-00xu-5090000000-f7e42d08813d9639f55d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 20V, Negative-QTOF	splash10-00di-2090000000-d3a78d47f393ca40986c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 40V, Negative-QTOF	splash10-0006-9320000000-fc45520b074c9c94042a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 10V, Positive-QTOF	splash10-01b9-0090000000-26345aa356dcf14f8721	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 20V, Positive-QTOF	splash10-00di-0090000000-a33124798242dfbf0f75	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 40V, Positive-QTOF	splash10-00xs-0960000000-f226b62370ec87a71fe3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 10V, Negative-QTOF	splash10-01b9-0090000000-d10d5b4ac727a9ce3cdf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 20V, Negative-QTOF	splash10-00di-0190000000-d7be2c6f7acc0535c4b0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-O-quinone 40V, Negative-QTOF	splash10-00di-0290000000-e5c8a156df1e773ff3ec	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

C16606

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24892807

PDB ID

Not Available

ChEBI ID

80601

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 Carbamazepine-O-quinone (HMDB0060566)

MOL for HMDB0060566 (Carbamazepine-O-quinone)

3D MOL for HMDB0060566 (Carbamazepine-O-quinone)

3D SDF for HMDB0060566 (Carbamazepine-O-quinone)

3D-SDF for HMDB0060566 (Carbamazepine-O-quinone)

PDB for HMDB0060566 (Carbamazepine-O-quinone)

3D PDB for HMDB0060566 (Carbamazepine-O-quinone)

SMILES for HMDB0060566 (Carbamazepine-O-quinone)

INCHI for HMDB0060566 (Carbamazepine-O-quinone)

Structure for HMDB0060566 (Carbamazepine-O-quinone)

3D Structure for HMDB0060566 (Carbamazepine-O-quinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra