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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 18:42:28 UTC

Update Date

2019-07-23 07:14:50 UTC

HMDB ID

HMDB0060673

Secondary Accession Numbers

HMDB60673

Metabolite Identification

Common Name

2,3-Dihydroxycarbamazepine

Description

2,3-Dihydroxycarbamazepine 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. 2,3-Dihydroxycarbamazepine is a metabolite of carbamazepine. 2,3-Dihydroxycarbamazepine is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,3-dihydroxycarbamazepine can be biosynthesized from 3-hydroxycarbamazepine; which is mediated by the enzymes cytochrome P450 2C19, cytochrome P450 3A4, and cytochrome P450 3A5. In humans, 2,3-dihydroxycarbamazepine is involved in carbamazepine metabolism pathway.

Structure

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

HMDB0060673
     RDKit          3D
2,3-Dihydroxycarbamazepine
 32 34  0  0  0  0  0  0  0  0999 V2000
    0.5709    2.9612   -0.7919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431    2.2245   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315    2.8599   -0.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4806    0.8651   -0.0157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6690    0.2054    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298    1.0031    1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6364    0.5354    1.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466   -0.7292    1.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838   -1.5512    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -1.0633    0.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -2.0521   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0656   -2.0379   -1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817   -1.0672   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2765   -1.5429   -0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.7686   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761   -1.2576   -0.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.4935    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225    1.2849    0.3760 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8489    0.9744    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889    0.1995   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708    3.8834   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558    2.5844   -1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798    1.9797    1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2618    1.1370    2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9992   -1.1238    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6083   -2.5512    0.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785   -2.8620   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993   -2.8385   -1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4458   -2.5189   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7956   -2.1925   -0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746    1.0262    0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503    1.9391    0.6031 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  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20  4  1  0
 10  5  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  1  0
M  END

 
  Mrv0541 06181311422D          
 
 20 22  0  0  0  0            999 V2000
   14.3374  -11.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0760  -11.5891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8244  -11.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0164  -12.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1634  -12.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5137  -13.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6879  -13.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7253  -11.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9402  -11.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7662  -12.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3784  -13.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8134  -12.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3967  -12.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1832  -11.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3863  -11.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1088  -10.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3797  -10.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8092  -10.3506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9981  -12.7118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3269  -11.0977    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
 10 19  1  0  0  0  0
  9 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060673

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H12N2O3/c16-15(20)17-11-4-2-1-3-9(11)5-6-10-7-13(18)14(19)8-12(10)17/h1-8,18-19H,(H2,16,20)

> <INCHI_KEY>
YITIUNLDWDJVSI-UHFFFAOYSA-N

> <FORMULA>
C15H12N2O3

> <MOLECULAR_WEIGHT>
268.2674

> <EXACT_MASS>
268.08479226

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.016250543788864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
2.158899743

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.336409427683005

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.980749519799124

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7154917390466564

> <JCHEM_POLAR_SURFACE_AREA>
86.79

> <JCHEM_REFRACTIVITY>
75.84980000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6-dihydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060673
     RDKit          3D
2,3-Dihydroxycarbamazepine
 32 34  0  0  0  0  0  0  0  0999 V2000
    0.5709    2.9612   -0.7919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431    2.2245   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315    2.8599   -0.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4806    0.8651   -0.0157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6690    0.2054    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298    1.0031    1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6364    0.5354    1.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466   -0.7292    1.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838   -1.5512    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -1.0633    0.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -2.0521   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0656   -2.0379   -1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817   -1.0672   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2765   -1.5429   -0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.7686   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761   -1.2576   -0.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.4935    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225    1.2849    0.3760 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8489    0.9744    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889    0.1995   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708    3.8834   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558    2.5844   -1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798    1.9797    1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2618    1.1370    2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9992   -1.1238    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6083   -2.5512    0.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785   -2.8620   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993   -2.8385   -1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4458   -2.5189   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7956   -2.1925   -0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746    1.0262    0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503    1.9391    0.6031 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  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20  4  1  0
 10  5  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  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      26.763 -22.309   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      28.142 -21.633   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      29.539 -22.283   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.897 -23.769   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.438 -23.825   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.959 -24.994   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.417 -25.014   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.620 -21.277   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.155 -21.750   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.830 -23.266   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.973 -24.298   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.385 -24.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.474 -23.079   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.075 -21.591   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.588 -21.193   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.203 -20.094   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      26.842 -19.327   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      29.510 -19.321   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      22.396 -23.729   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      23.010 -20.716   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   20                                                  
CONECT   10    9   11   19                                                  
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   10                                                            
CONECT   20    9                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0060673
HETATM    1  N1  UNL     1       0.571   2.961  -0.792  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.543   2.225  -0.308  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.631   2.860  -0.157  1.00  0.00           O  
HETATM    4  N2  UNL     1      -0.481   0.865  -0.016  1.00  0.00           N  
HETATM    5  C2  UNL     1      -1.669   0.205   0.411  1.00  0.00           C  
HETATM    6  C3  UNL     1      -2.430   1.003   1.215  1.00  0.00           C  
HETATM    7  C4  UNL     1      -3.636   0.535   1.711  1.00  0.00           C  
HETATM    8  C5  UNL     1      -4.047  -0.729   1.386  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.284  -1.551   0.572  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.094  -1.063   0.094  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.380  -2.052  -0.732  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.066  -2.038  -1.056  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.982  -1.067  -0.686  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.276  -1.543  -0.828  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.381  -0.769  -0.477  1.00  0.00           C  
HETATM   16  O2  UNL     1       4.676  -1.258  -0.626  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.150   0.494   0.020  1.00  0.00           C  
HETATM   18  O3  UNL     1       4.222   1.285   0.376  1.00  0.00           O  
HETATM   19  C14 UNL     1       1.849   0.974   0.165  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.789   0.199  -0.189  1.00  0.00           C  
HETATM   21  H1  UNL     1       0.771   3.883  -0.353  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.156   2.584  -1.568  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.080   1.980   1.487  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.262   1.137   2.344  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.999  -1.124   1.766  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.608  -2.551   0.316  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.979  -2.862  -1.109  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.299  -2.839  -1.667  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.446  -2.519  -1.212  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.796  -2.193  -0.996  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.175   1.026   0.305  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.650   1.939   0.603  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3    3    4
CONECT    4    5   20
CONECT    5    6    6   10
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   13   14   14   20
CONECT   14   15   29
CONECT   15   16   17   17
CONECT   16   30
CONECT   17   18   19
CONECT   18   31
CONECT   19   20   20   32
END

HMDB0060673
     RDKit          3D
2,3-Dihydroxycarbamazepine
 32 34  0  0  0  0  0  0  0  0999 V2000
    0.5709    2.9612   -0.7919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431    2.2245   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315    2.8599   -0.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4806    0.8651   -0.0157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6690    0.2054    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298    1.0031    1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6364    0.5354    1.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466   -0.7292    1.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838   -1.5512    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -1.0633    0.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -2.0521   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0656   -2.0379   -1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817   -1.0672   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2765   -1.5429   -0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.7686   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761   -1.2576   -0.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.4935    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225    1.2849    0.3760 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8489    0.9744    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889    0.1995   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708    3.8834   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558    2.5844   -1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798    1.9797    1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2618    1.1370    2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9992   -1.1238    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6083   -2.5512    0.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785   -2.8620   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993   -2.8385   -1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4458   -2.5189   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7956   -2.1925   -0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746    1.0262    0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503    1.9391    0.6031 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  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20  4  1  0
 10  5  1  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂N₂O₃

Average Molecular Weight

268.2674

Monoisotopic Molecular Weight

268.08479226

IUPAC Name

5,6-dihydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide

Traditional Name

5,6-dihydroxy-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(O)=C(O)C=C12

InChI Identifier

InChI=1S/C15H12N2O3/c16-15(20)17-11-4-2-1-3-9(11)5-6-10-7-13(18)14(19)8-12(10)17/h1-8,18-19H,(H2,16,20)

InChI Key

YITIUNLDWDJVSI-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
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Carbonic acid derivative
Urea
Azacycle
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzooxazepine (CHEBI:80598 )

Ontology

Not Available

Liver (HMDB: HMDB0060673)
Kidney (HMDB: HMDB0060673)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060673)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060673)

Cellular substructure

Membrane (HMDB: HMDB0060673)

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	0.18 g/L	ALOGPS
logP	1.75	ALOGPS
logP	2.16	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.98	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.85 m³·mol⁻¹	ChemAxon
Polarizability	27.02 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]+	161.383	31661259
DarkChem	[M-H]-	159.507	31661259
DeepCCS	[M-2H]-	189.858	30932474
DeepCCS	[M+Na]+	165.399	30932474
AllCCS	[M+H]+	161.3	32859911
AllCCS	[M+H-H2O]+	157.5	32859911
AllCCS	[M+NH4]+	164.9	32859911
AllCCS	[M+Na]+	166.0	32859911
AllCCS	[M-H]-	162.3	32859911
AllCCS	[M+Na-2H]-	161.7	32859911
AllCCS	[M+HCOO]-	161.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydroxycarbamazepine	NC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=C(O)C=C12	4434.4	Standard polar	33892256
2,3-Dihydroxycarbamazepine	NC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=C(O)C=C12	2622.7	Standard non polar	33892256
2,3-Dihydroxycarbamazepine	NC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=C(O)C=C12	2850.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydroxycarbamazepine,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O)N(C(N)=O)C1=CC=CC=C1C=C2	2737.7	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=CC3=CC=CC=C3N2C(N)=O)C=C1O	2740.6	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,1TMS,isomer #3	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=C(O)C=C21	2718.6	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N(C(N)=O)C1=CC=CC=C1C=C2	2724.1	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,2TMS,isomer #2	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C)=C(O)C=C21	2662.5	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,2TMS,isomer #3	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=C(O[Si](C)(C)C)C=C21	2665.1	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,2TMS,isomer #4	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC(O)=C(O)C=C21)[Si](C)(C)C	2736.2	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C21	2701.7	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C21	2664.8	Standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C21	3465.8	Standard polar	33892256
2,3-Dihydroxycarbamazepine,3TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1C=C2	2704.3	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1C=C2	2874.9	Standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1C=C2	3558.3	Standard polar	33892256
2,3-Dihydroxycarbamazepine,3TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=CC3=CC=CC=C3N2C(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O	2705.9	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=CC3=CC=CC=C3N2C(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O	2880.3	Standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=CC3=CC=CC=C3N2C(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O	3559.6	Standard polar	33892256
2,3-Dihydroxycarbamazepine,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1C=C2	2742.8	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1C=C2	2899.0	Standard non polar	33892256
2,3-Dihydroxycarbamazepine,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1C=C2	3385.9	Standard polar	33892256
2,3-Dihydroxycarbamazepine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N(C(N)=O)C1=CC=CC=C1C=C2	3000.1	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=CC3=CC=CC=C3N2C(N)=O)C=C1O	2993.2	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=C(O)C=C21	2930.3	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N(C(N)=O)C1=CC=CC=C1C=C2	3193.0	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C21	3106.8	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C21	3101.3	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC(O)=C(O)C=C21)[Si](C)(C)C(C)(C)C	3168.2	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C21	3310.2	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C21	3283.9	Standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C21	3715.4	Standard polar	33892256
2,3-Dihydroxycarbamazepine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1C=C2	3362.2	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1C=C2	3415.1	Standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1C=C2	3737.7	Standard polar	33892256
2,3-Dihydroxycarbamazepine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=CC3=CC=CC=C3N2C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	3349.0	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=CC3=CC=CC=C3N2C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	3421.1	Standard non polar	33892256
2,3-Dihydroxycarbamazepine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=CC3=CC=CC=C3N2C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	3744.7	Standard polar	33892256
2,3-Dihydroxycarbamazepine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1C=C2	3589.6	Semi standard non polar	33892256
2,3-Dihydroxycarbamazepine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1C=C2	3664.3	Standard non polar	33892256
2,3-Dihydroxycarbamazepine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1C=C2	3678.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxycarbamazepine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-0190000000-509be1694251c8235b8b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxycarbamazepine GC-MS (2 TMS) - 70eV, Positive	splash10-00dj-4139000000-97a18e758ab55c5cd77d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxycarbamazepine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxycarbamazepine 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 - 2,3-Dihydroxycarbamazepine 10V, Positive-QTOF	splash10-014i-0090000000-42cebd081dc646351080	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxycarbamazepine 20V, Positive-QTOF	splash10-00or-0190000000-1ec3e2fe61df88b9088c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxycarbamazepine 40V, Positive-QTOF	splash10-0a4m-1890000000-8b5812d17e9c9ece03b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxycarbamazepine 10V, Negative-QTOF	splash10-00r6-5090000000-40206d8a217ab805dc13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxycarbamazepine 20V, Negative-QTOF	splash10-00di-2090000000-0a832a123ad5fdf58cd7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxycarbamazepine 40V, Negative-QTOF	splash10-0006-9210000000-c0051afee3be9b00e7e8	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

C16603

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24892806

PDB ID

Not Available

ChEBI ID

80598

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 2,3-Dihydroxycarbamazepine (HMDB0060673)

MOL for HMDB0060673 (2,3-Dihydroxycarbamazepine)

3D MOL for HMDB0060673 (2,3-Dihydroxycarbamazepine)

3D SDF for HMDB0060673 (2,3-Dihydroxycarbamazepine)

3D-SDF for HMDB0060673 (2,3-Dihydroxycarbamazepine)

PDB for HMDB0060673 (2,3-Dihydroxycarbamazepine)

3D PDB for HMDB0060673 (2,3-Dihydroxycarbamazepine)

SMILES for HMDB0060673 (2,3-Dihydroxycarbamazepine)

INCHI for HMDB0060673 (2,3-Dihydroxycarbamazepine)

Structure for HMDB0060673 (2,3-Dihydroxycarbamazepine)

3D Structure for HMDB0060673 (2,3-Dihydroxycarbamazepine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra