Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 17:47:55 UTC

Update Date

2021-09-14 14:57:44 UTC

HMDB ID

HMDB0060658

Secondary Accession Numbers

HMDB0060978
HMDB60658
HMDB60978

Metabolite Identification

Common Name

Carbamazepine-10,11-epoxide

Description

Carbamazepine-10,11-epoxide, also known as 10,11-epoxycarbamazepine, 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-10,11-epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, carbamazepine-10,11-epoxide participates in a number of enzymatic reactions. In particular, carbamazepine-10,11-epoxide can be biosynthesized from carbamazepine; which is catalyzed by the enzymes cytochrome P450 2C8, cytochrome P450 3A4, cytochrome P450 3A5, cytochrome P450 3A7, and cytochrome P450 2C19. In addition, carbamazepine-10,11-epoxide can be converted into 10,11-dihydroxycarbamazepine; which is catalyzed by the enzyme epoxide hydrolase 1. An epoxide and metabolite of carbamazepine. In humans, carbamazepine-10,11-epoxide is involved in carbamazepine metabolism pathway.

Structure

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

HMDB0060658
     RDKit          3D
Carbamazepine-10,11-epoxide
 31 34  0  0  0  0  0  0  0  0999 V2000
    1.7304    2.7326   -0.5401 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4144    2.1832   -0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4909    3.0435   -0.5933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    0.8558   -0.0343 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797   -0.0739    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2306    0.5309    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -0.1985    1.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747   -1.5372    0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3090   -2.1082    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1390   -1.3972   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347   -2.2172   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -1.6241   -2.1269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1824   -1.8563   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8141   -0.6667   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869   -0.7836   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9362    0.2218    0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843    1.3987    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205    1.5436    0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2868    0.5261    0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501    3.6132   -0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4061    2.2239   -1.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1299    1.5585    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848    0.2712    1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512   -2.1126    0.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -3.1567   -0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4196   -3.3093   -0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -2.6372   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785   -1.7050   -0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0253    0.0976    0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0129    2.1535    1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    2.4295    0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 13 11  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

564
  Mrv0541 02271201082D          

 19 22  0  0  0  0            999 V2000
    4.5536   -1.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8677   -0.0280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1818   -1.2161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1540    0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576    1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637    1.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    1.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1774   -0.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5580   -0.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421    1.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933    1.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8677   -0.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9676   -0.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678   -0.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1512    0.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    0.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8842    2.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  2  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2 14  1  0  0  0  0
  3 14  1  0  0  0  0
  4  6  1  0  0  0  0
  4 10  2  0  0  0  0
  5  7  1  0  0  0  0
  5 11  2  0  0  0  0
  6  8  1  0  0  0  0
  6 12  2  0  0  0  0
  7  9  1  0  0  0  0
  7 13  2  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
  9 19  1  0  0  0  0
  8 19  1  0  0  0  0
  9  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060658

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C12

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

> <INCHI_KEY>
ZRWWEEVEIOGMMT-UHFFFAOYSA-N

> <FORMULA>
C15H12N2O2

> <MOLECULAR_WEIGHT>
252.268

> <EXACT_MASS>
252.089877638

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.60863944512308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-oxa-11-azatetracyclo[10.4.0.0²,⁴.0⁵,¹⁰]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.9744484013333332

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.959102252953276

> <JCHEM_PKA_STRONGEST_BASIC>
-3.706179331110255

> <JCHEM_POLAR_SURFACE_AREA>
58.86

> <JCHEM_REFRACTIVITY>
69.98430000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxa-11-azatetracyclo[10.4.0.0²,⁴.0⁵,¹⁰]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060658
     RDKit          3D
Carbamazepine-10,11-epoxide
 31 34  0  0  0  0  0  0  0  0999 V2000
    1.7304    2.7326   -0.5401 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4144    2.1832   -0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4909    3.0435   -0.5933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    0.8558   -0.0343 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797   -0.0739    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2306    0.5309    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -0.1985    1.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747   -1.5372    0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3090   -2.1082    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1390   -1.3972   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347   -2.2172   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -1.6241   -2.1269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1824   -1.8563   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8141   -0.6667   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869   -0.7836   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9362    0.2218    0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843    1.3987    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205    1.5436    0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2868    0.5261    0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501    3.6132   -0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4061    2.2239   -1.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1299    1.5585    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848    0.2712    1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512   -2.1126    0.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -3.1567   -0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4196   -3.3093   -0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -2.6372   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785   -1.7050   -0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0253    0.0976    0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0129    2.1535    1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    2.4295    0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 13 11  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 564                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       8.500  -2.270   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.220  -0.052   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.939  -2.270   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.552   0.589   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.887   0.589   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.881   2.031   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.559   2.031   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.959   3.187   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.481   3.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.664  -0.475   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.775  -0.475   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.345   2.507   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.094   2.507   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.220  -1.531   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.140  -0.033   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.300  -0.033   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.482   1.469   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.957   1.469   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.251   4.521   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2    4    5   14                                                  
CONECT    3   14                                                            
CONECT    4    2    6   10                                                  
CONECT    5    2    7   11                                                  
CONECT    6    4    8   12                                                  
CONECT    7    5    9   13                                                  
CONECT    8    6   19    9                                                  
CONECT    9    7   19    8                                                  
CONECT   10    4   15                                                       
CONECT   11    5   16                                                       
CONECT   12    6   17                                                       
CONECT   13    7   18                                                       
CONECT   14    1    2    3                                                  
CONECT   15   10   17                                                       
CONECT   16   11   18                                                       
CONECT   17   12   15                                                       
CONECT   18   13   16                                                       
CONECT   19    9    8                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0060658
HETATM    1  N1  UNL     1       1.730   2.733  -0.540  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.414   2.183  -0.379  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.491   3.043  -0.593  1.00  0.00           O  
HETATM    4  N2  UNL     1       0.121   0.856  -0.034  1.00  0.00           N  
HETATM    5  C2  UNL     1       1.180  -0.074   0.196  1.00  0.00           C  
HETATM    6  C3  UNL     1       2.231   0.531   0.830  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.351  -0.199   1.112  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.375  -1.537   0.741  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.309  -2.108   0.112  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.139  -1.397  -0.197  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.135  -2.217  -0.845  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.285  -1.624  -2.127  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.182  -1.856  -1.055  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.814  -0.667  -0.434  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.187  -0.784  -0.289  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.936   0.222   0.277  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.384   1.399   0.734  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.021   1.544   0.604  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.287   0.526   0.033  1.00  0.00           C  
HETATM   20  H1  UNL     1       2.050   3.613  -0.091  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.406   2.224  -1.143  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.130   1.558   1.117  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.185   0.271   1.610  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.251  -2.113   0.959  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.311  -3.157  -0.185  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.420  -3.309  -0.960  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.924  -2.637  -1.329  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.679  -1.705  -0.637  1.00  0.00           H  
HETATM   29  H10 UNL     1      -5.025   0.098   0.377  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.013   2.154   1.167  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.510   2.429   0.968  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   13   26
CONECT   12   13
CONECT   13   14   27
CONECT   14   15   15   19
CONECT   15   16   28
CONECT   16   17   17   29
CONECT   17   18   30
CONECT   18   19   19   31
END

HMDB0060658
     RDKit          3D
Carbamazepine-10,11-epoxide
 31 34  0  0  0  0  0  0  0  0999 V2000
    1.7304    2.7326   -0.5401 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4144    2.1832   -0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4909    3.0435   -0.5933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    0.8558   -0.0343 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797   -0.0739    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2306    0.5309    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -0.1985    1.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747   -1.5372    0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3090   -2.1082    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1390   -1.3972   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347   -2.2172   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -1.6241   -2.1269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1824   -1.8563   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8141   -0.6667   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869   -0.7836   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9362    0.2218    0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843    1.3987    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205    1.5436    0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2868    0.5261    0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501    3.6132   -0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4061    2.2239   -1.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1299    1.5585    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848    0.2712    1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512   -2.1126    0.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -3.1567   -0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4196   -3.3093   -0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -2.6372   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785   -1.7050   -0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0253    0.0976    0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0129    2.1535    1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    2.4295    0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 13 11  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10,11-Epoxycarbamazepine	ChEBI
Carbamazepine 10,11-oxide	ChEBI
Carbamazepine epoxide	ChEBI
Carbamazepine 10,11-epoxide	HMDB
Carbamazepine epoxide, 1a-(13)C-labeled	HMDB

Chemical Formula

C₁₅H₁₂N₂O₂

Average Molecular Weight

252.268

Monoisotopic Molecular Weight

252.089877638

IUPAC Name

3-oxa-11-azatetracyclo[10.4.0.0²,⁴.0⁵,¹⁰]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide

Traditional Name

3-oxa-11-azatetracyclo[10.4.0.0²,⁴.0⁵,¹⁰]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide

CAS Registry Number

36507-30-9

SMILES

NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C12

InChI Identifier

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

InChI Key

ZRWWEEVEIOGMMT-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
Carbonic acid derivative
Urea
Dialkyl ether
Oxirane
Ether
Azacycle
Oxacycle
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ureas (CHEBI:3388 )
epoxide (CHEBI:3388 )
dibenzooxazepine (CHEBI:3388 )

Ontology

Not Available

Liver (HMDB: HMDB0060658)
Kidney (HMDB: HMDB0060658)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060658)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060658)

Cellular substructure

Cytoplasm (HMDB: HMDB0060658)

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	1.34 g/L	ALOGPS
logP	1.58	ALOGPS
logP	1.97	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	15.96	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.86 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.98 m³·mol⁻¹	ChemAxon
Polarizability	25.61 Å³	ChemAxon
Number of Rings	4	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]+	158.3	31661259
DarkChem	[M-H]-	154.362	31661259
DeepCCS	[M-2H]-	179.778	30932474
DeepCCS	[M+Na]+	154.85	30932474
AllCCS	[M+H]+	158.0	32859911
AllCCS	[M+H-H2O]+	154.0	32859911
AllCCS	[M+NH4]+	161.7	32859911
AllCCS	[M+Na]+	162.8	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	160.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carbamazepine-10,11-epoxide	NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C12	3671.6	Standard polar	33892256
Carbamazepine-10,11-epoxide	NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C12	2161.4	Standard non polar	33892256
Carbamazepine-10,11-epoxide	NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C12	2408.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carbamazepine-10,11-epoxide,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21	2302.7	Semi standard non polar	33892256
Carbamazepine-10,11-epoxide,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21	2356.1	Standard non polar	33892256
Carbamazepine-10,11-epoxide,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21	3328.4	Standard polar	33892256
Carbamazepine-10,11-epoxide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C	2412.4	Semi standard non polar	33892256
Carbamazepine-10,11-epoxide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C	2578.5	Standard non polar	33892256
Carbamazepine-10,11-epoxide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C	3166.3	Standard polar	33892256
Carbamazepine-10,11-epoxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21	2512.5	Semi standard non polar	33892256
Carbamazepine-10,11-epoxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21	2568.9	Standard non polar	33892256
Carbamazepine-10,11-epoxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21	3394.2	Standard polar	33892256
Carbamazepine-10,11-epoxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2832.1	Semi standard non polar	33892256
Carbamazepine-10,11-epoxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2909.9	Standard non polar	33892256
Carbamazepine-10,11-epoxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	3233.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Carbamazepine-10,11-epoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2090000000-1c00887035045a46e64c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carbamazepine-10,11-epoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-QTOF , positive-QTOF	splash10-0ik9-0090000000-ecf7de18b8b6dca8e574	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-QTOF , positive-QTOF	splash10-01q9-0960000000-baaab3735118a6815d95	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-5f960cbf9a2cc6167270	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-7ae96bba0545f7a49d65	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-f5d9e3256a5025c053f5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-01p9-0090000000-b4a8017bc5a22029286a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-0udi-0090000000-92d916d85c6bfb1c8c8c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-03ei-0390000000-8b6d0377758bc766aeca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-01q9-0950000000-54f4932e8819ef33fc59	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-001i-0910000000-f98fd081a308fa16c768	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-8b69c7ac8b048b7d3892	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-c63c11ed10e957dca130	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-0udi-0090000000-623298bbf57b289b1282	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-03ei-0390000000-b77b3aa6c369fd8b0818	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-001i-0950000000-32d3a419a11e5ffcd132	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-001i-0910000000-72c13fa6ddd8b27641e1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-d4ce4b02188dd4b58833	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-c2ed076d4e592ce2f653	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-b5886f3f5846ab71f72d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 10V, Positive-QTOF	splash10-0udi-0090000000-af9f413b6f446d69709f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 20V, Positive-QTOF	splash10-0ik9-0090000000-10bc18215ee3ab2ba1eb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 40V, Positive-QTOF	splash10-01p6-8690000000-a0c1e51c6cec85694c4a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 10V, Negative-QTOF	splash10-0k96-5090000000-ecc2f07a1eefb2949d89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 20V, Negative-QTOF	splash10-0a4i-3090000000-19d6ac25e86c1e0a6a84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 40V, Negative-QTOF	splash10-0006-9320000000-a52f23fc0b4f15a7d389	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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

C07496

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2555

PDB ID

Not Available

ChEBI ID

3388

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Wei CY, Chung WH, Huang HW, Chen YT, Hung SI: Direct interaction between HLA-B and carbamazepine activates T cells in patients with Stevens-Johnson syndrome. J Allergy Clin Immunol. 2012 Jun;129(6):1562-9.e5. doi: 10.1016/j.jaci.2011.12.990. Epub 2012 Feb 8. [PubMed:22322005 ]
McKauge L, Tyrer JH, Eadie MJ: Factors influencing simultaneous concentrations of carbamazepine and its epoxide in plasma. Ther Drug Monit. 1981;3(1):63-70. [PubMed:7233491 ]

Showing metabocard for Carbamazepine-10,11-epoxide (HMDB0060658)

MOL for HMDB0060658 (Carbamazepine-10,11-epoxide)

3D MOL for HMDB0060658 (Carbamazepine-10,11-epoxide)

3D SDF for HMDB0060658 (Carbamazepine-10,11-epoxide)

3D-SDF for HMDB0060658 (Carbamazepine-10,11-epoxide)

PDB for HMDB0060658 (Carbamazepine-10,11-epoxide)

3D PDB for HMDB0060658 (Carbamazepine-10,11-epoxide)

SMILES for HMDB0060658 (Carbamazepine-10,11-epoxide)

INCHI for HMDB0060658 (Carbamazepine-10,11-epoxide)

Structure for HMDB0060658 (Carbamazepine-10,11-epoxide)

3D Structure for HMDB0060658 (Carbamazepine-10,11-epoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra