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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:53:41 UTC

Update Date

2021-09-14 14:58:20 UTC

HMDB ID

HMDB0060702

Secondary Accession Numbers

HMDB60702

Metabolite Identification

Common Name

(S)-MHD

Description

(S)-MHD, also known as bia 2-194Erelib or PAZZUL, 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 (S)-MHD is an extremely weak basic (essentially neutral) compound (based on its pKa). Oxcarbazepine is marketed as Trileptal by Novartis and available in some countries as a generic drug. Oxcarbazepine (ox-kar-BAY-zih-peen) is a anticholinergic anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy. It is also used to treat anxiety and mood disorders, and benign motor tics.

Structure

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

HMDB0060702
     RDKit          3D
(S)-MHD
 33 35  0  0  0  0  0  0  0  0999 V2000
   -0.6524    3.3660   -0.5463 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967    2.4286   -0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5757    2.9280   -0.2491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040    1.1010    0.0472 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3992    0.3228    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    0.9697    1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5390    0.3686    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700   -0.8994    0.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429   -1.5619    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6236   -0.9580   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7412   -1.7859   -1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -1.9648   -0.6571 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3587   -2.6503   -1.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299   -0.7958   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7845   -1.1327   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7243   -0.2346    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3648    1.0478    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    1.4022    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052    0.4966    0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375    3.1283   -1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597    4.2859   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0469    1.9639    1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2737    0.8631    1.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7447   -1.3775    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0523   -2.5398   -0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7316   -1.2469   -2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2005   -2.7963   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -2.6469    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -3.5745   -1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245   -2.1275   -0.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886   -0.4975    0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1003    1.7511    0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6963    2.3667    0.8599 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
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  1
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv0541 07041311532D          

 19 21  0  0  1  0            999 V2000
    3.0892    1.5695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    1.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    1.5695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    0.3320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -1.4753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0332   -2.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060702

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)N1C2=CC=CC=C2C[C@H](O)C2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)/t14-/m0/s1

> <INCHI_KEY>
BMPDWHIDQYTSHX-AWEZNQCLSA-N

> <FORMULA>
C15H14N2O2

> <MOLECULAR_WEIGHT>
254.2839

> <EXACT_MASS>
254.105527702

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.450125977274624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10S)-10-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaene-2-carboxamide

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.7317409759999998

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.966328258863758

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.100105594069575

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1897706968030954

> <JCHEM_POLAR_SURFACE_AREA>
66.56

> <JCHEM_REFRACTIVITY>
72.28690000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10S)-10-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaene-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060702
     RDKit          3D
(S)-MHD
 33 35  0  0  0  0  0  0  0  0999 V2000
   -0.6524    3.3660   -0.5463 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967    2.4286   -0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5757    2.9280   -0.2491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040    1.1010    0.0472 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3992    0.3228    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    0.9697    1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5390    0.3686    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700   -0.8994    0.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429   -1.5619    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6236   -0.9580   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7412   -1.7859   -1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -1.9648   -0.6571 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3587   -2.6503   -1.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299   -0.7958   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7845   -1.1327   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7243   -0.2346    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3648    1.0478    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    1.4022    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052    0.4966    0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375    3.1283   -1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597    4.2859   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0469    1.9639    1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2737    0.8631    1.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7447   -1.3775    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0523   -2.5398   -0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7316   -1.2469   -2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2005   -2.7963   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -2.6469    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -3.5745   -1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245   -2.1275   -0.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886   -0.4975    0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1003    1.7511    0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6963    2.3667    0.8599 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
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  1
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  N   UNK     0       5.767   2.930   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       7.100   2.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.434   2.930   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.100   0.620   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.488  -0.049   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.617   0.999   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.088   0.545   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.431  -0.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.302  -2.004   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.830  -1.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.870  -2.754   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.330  -2.754   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.662  -4.141   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.370  -1.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.713  -0.049   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.584   0.999   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.112   0.545   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.770  -0.956   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.898  -2.004   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   15                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14    4   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0060702
HETATM    1  N1  UNL     1      -0.652   3.366  -0.546  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.397   2.429  -0.235  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.576   2.928  -0.249  1.00  0.00           O  
HETATM    4  N2  UNL     1       0.204   1.101   0.047  1.00  0.00           N  
HETATM    5  C2  UNL     1       1.399   0.323   0.261  1.00  0.00           C  
HETATM    6  C3  UNL     1       2.335   0.970   1.019  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.539   0.369   1.314  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.770  -0.899   0.826  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.843  -1.562   0.066  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.624  -0.958  -0.236  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.741  -1.786  -1.093  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.649  -1.965  -0.657  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.359  -2.650  -1.678  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.430  -0.796  -0.233  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.784  -1.133  -0.118  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.724  -0.235   0.315  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.365   1.048   0.657  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.018   1.402   0.549  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.105   0.497   0.114  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.338   3.128  -1.294  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.760   4.286  -0.066  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.047   1.964   1.386  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.274   0.863   1.899  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.745  -1.378   1.069  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.052  -2.540  -0.294  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.732  -1.247  -2.089  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.201  -2.796  -1.219  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.619  -2.647   0.254  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.963  -3.574  -1.657  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.125  -2.127  -0.372  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.789  -0.498   0.405  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.100   1.751   0.995  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.696   2.367   0.860  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3    3    4
CONECT    4    5   19
CONECT    5    6    6   10
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11
CONECT   11   12   26   27
CONECT   12   13   14   28
CONECT   13   29
CONECT   14   15   15   19
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   32
CONECT   18   19   19   33
END

HMDB0060702
     RDKit          3D
(S)-MHD
 33 35  0  0  0  0  0  0  0  0999 V2000
   -0.6524    3.3660   -0.5463 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967    2.4286   -0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5757    2.9280   -0.2491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040    1.1010    0.0472 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3992    0.3228    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    0.9697    1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5390    0.3686    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700   -0.8994    0.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429   -1.5619    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6236   -0.9580   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7412   -1.7859   -1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -1.9648   -0.6571 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3587   -2.6503   -1.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299   -0.7958   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7845   -1.1327   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7243   -0.2346    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3648    1.0478    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    1.4022    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052    0.4966    0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375    3.1283   -1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597    4.2859   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0469    1.9639    1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2737    0.8631    1.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7447   -1.3775    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0523   -2.5398   -0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7316   -1.2469   -2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2005   -2.7963   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -2.6469    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634   -3.5745   -1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245   -2.1275   -0.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886   -0.4975    0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1003    1.7511    0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6963    2.3667    0.8599 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
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  4  1  0
 10  5  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  1
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
BIA 2-194Erelib	HMDB
PAZZUL	HMDB
STEDESA	HMDB
(10S)-10-Hydroxy-10,11-dihydro-5H-dibenzo(b,F)azepin-5-carboxamide	HMDB

Chemical Formula

C₁₅H₁₄N₂O₂

Average Molecular Weight

254.2839

Monoisotopic Molecular Weight

254.105527702

IUPAC Name

(10S)-10-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaene-2-carboxamide

Traditional Name

(10S)-10-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaene-2-carboxamide

CAS Registry Number

Not Available

SMILES

NC(=O)N1C2=CC=CC=C2C[C@H](O)C2=C1C=CC=C2

InChI Identifier

InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)/t14-/m0/s1

InChI Key

BMPDWHIDQYTSHX-AWEZNQCLSA-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
Secondary alcohol
Urea
Azacycle
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060702)
Liver (HMDB: HMDB0060702)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060702)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060702)

Cellular substructure

Cytoplasm (HMDB: HMDB0060702)

Process

Not Available

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	0.55 g/L	ALOGPS
logP	1.26	ALOGPS
logP	1.73	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.1	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.56 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.29 m³·mol⁻¹	ChemAxon
Polarizability	26.45 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]+	158.55	31661259
DarkChem	[M-H]-	156.685	31661259
DeepCCS	[M+H]+	153.857	30932474
DeepCCS	[M-H]-	151.462	30932474
DeepCCS	[M-2H]-	184.539	30932474
DeepCCS	[M+Na]+	159.77	30932474
AllCCS	[M+H]+	158.8	32859911
AllCCS	[M+H-H2O]+	154.8	32859911
AllCCS	[M+NH4]+	162.5	32859911
AllCCS	[M+Na]+	163.5	32859911
AllCCS	[M-H]-	161.4	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	160.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-MHD	NC(=O)N1C2=CC=CC=C2C[C@H](O)C2=C1C=CC=C2	3926.1	Standard polar	33892256
(S)-MHD	NC(=O)N1C2=CC=CC=C2C[C@H](O)C2=C1C=CC=C2	2306.3	Standard non polar	33892256
(S)-MHD	NC(=O)N1C2=CC=CC=C2C[C@H](O)C2=C1C=CC=C2	2499.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-MHD,1TMS,isomer #1	C[Si](C)(C)O[C@H]1CC2=CC=CC=C2N(C(N)=O)C2=CC=CC=C21	2299.1	Semi standard non polar	33892256
(S)-MHD,1TMS,isomer #2	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C[C@H](O)C2=CC=CC=C21	2331.1	Semi standard non polar	33892256
(S)-MHD,2TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C[C@H](O[Si](C)(C)C)C2=CC=CC=C21	2347.7	Semi standard non polar	33892256
(S)-MHD,2TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C[C@H](O[Si](C)(C)C)C2=CC=CC=C21	2397.8	Standard non polar	33892256
(S)-MHD,2TMS,isomer #1	C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C[C@H](O[Si](C)(C)C)C2=CC=CC=C21	3060.7	Standard polar	33892256
(S)-MHD,2TMS,isomer #2	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C[C@H](O)C2=CC=CC=C21)[Si](C)(C)C	2434.4	Semi standard non polar	33892256
(S)-MHD,2TMS,isomer #2	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C[C@H](O)C2=CC=CC=C21)[Si](C)(C)C	2665.2	Standard non polar	33892256
(S)-MHD,2TMS,isomer #2	C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C[C@H](O)C2=CC=CC=C21)[Si](C)(C)C	3161.5	Standard polar	33892256
(S)-MHD,3TMS,isomer #1	C[Si](C)(C)O[C@H]1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2419.4	Semi standard non polar	33892256
(S)-MHD,3TMS,isomer #1	C[Si](C)(C)O[C@H]1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2597.7	Standard non polar	33892256
(S)-MHD,3TMS,isomer #1	C[Si](C)(C)O[C@H]1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C21	2914.6	Standard polar	33892256
(S)-MHD,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC2=CC=CC=C2N(C(N)=O)C2=CC=CC=C21	2538.3	Semi standard non polar	33892256
(S)-MHD,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C[C@H](O)C2=CC=CC=C21	2547.3	Semi standard non polar	33892256
(S)-MHD,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2713.6	Semi standard non polar	33892256
(S)-MHD,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2857.4	Standard non polar	33892256
(S)-MHD,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3223.1	Standard polar	33892256
(S)-MHD,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C[C@H](O)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2820.7	Semi standard non polar	33892256
(S)-MHD,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C[C@H](O)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	3065.7	Standard non polar	33892256
(S)-MHD,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C[C@H](O)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	3250.8	Standard polar	33892256
(S)-MHD,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3015.5	Semi standard non polar	33892256
(S)-MHD,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3207.7	Standard non polar	33892256
(S)-MHD,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC2=CC=CC=C2N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3144.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-MHD GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fu-1790000000-a7f14b7ad0facf9f3f45	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-MHD GC-MS (1 TMS) - 70eV, Positive	splash10-023c-8092000000-7a3da09410d5d9b659b2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-MHD 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 - (S)-MHD 10V, Positive-QTOF	splash10-052r-0090000000-e1ffdac8bf93f4c80d2f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 20V, Positive-QTOF	splash10-000l-0390000000-c7cd4fed8e7d6a26937e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 40V, Positive-QTOF	splash10-0006-9640000000-fa3c2d75871369dca093	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 10V, Negative-QTOF	splash10-0006-6290000000-a1b28c6ef7e673d18d4c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 20V, Negative-QTOF	splash10-01ox-4790000000-8ce70946b6b8aa2e2733	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 40V, Negative-QTOF	splash10-0006-9300000000-f844d0a5bb22313f7264	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 10V, Positive-QTOF	splash10-000i-0290000000-dd2cffde6c26c5fc05b1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 20V, Positive-QTOF	splash10-0006-0910000000-352b884191ff545bdbcd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 40V, Positive-QTOF	splash10-0006-0910000000-9390dfd4b86ba1321e09	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 10V, Negative-QTOF	splash10-0udu-0590000000-1dab6c7882cbd7228c82	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 20V, Negative-QTOF	splash10-0006-0910000000-8dbf5c32022b918c3f7e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-MHD 40V, Negative-QTOF	splash10-052f-0970000000-12f8e2155076d5ae0dd5	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9881504

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for (S)-MHD (HMDB0060702)

MOL for HMDB0060702 ((S)-MHD)

3D MOL for HMDB0060702 ((S)-MHD)

3D SDF for HMDB0060702 ((S)-MHD)

3D-SDF for HMDB0060702 ((S)-MHD)

PDB for HMDB0060702 ((S)-MHD)

3D PDB for HMDB0060702 ((S)-MHD)

SMILES for HMDB0060702 ((S)-MHD)

INCHI for HMDB0060702 ((S)-MHD)

Structure for HMDB0060702 ((S)-MHD)

3D Structure for HMDB0060702 ((S)-MHD)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra