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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-07 09:30:26 UTC

Update Date

2021-09-26 22:50:28 UTC

HMDB ID

HMDB0242748

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Asenapine

Description

5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring. Based on a literature review very few articles have been published on 5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole. This compound has been identified in human blood as reported by (PMID: 31557052 ). Asenapine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Asenapine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0242748
     RDKit          3D
Asenapine
 36 39  0  0  0  0  0  0  0  0999 V2000
    3.6192   -0.4880    0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817   -0.3114    0.3347 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9063    0.8674   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    0.6548   -1.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3844    1.5933   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2561    2.8476   -0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9791    3.9109   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8774    3.8362    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201    2.5986    1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    1.5178    0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557    0.3539    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5190   -0.9728    0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3854   -1.8187    1.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4537   -3.1451    1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324   -3.5879    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7356   -5.2851   -0.2451 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7840   -2.7372   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6853   -1.3819   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3096   -0.7733   -0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663   -1.3636   -0.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0536    0.3598    0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0926   -0.5839   -0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8411   -1.4036    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9780    1.8024    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566    0.8728   -1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949    0.9893   -2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4453    2.9709   -1.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509    4.8838   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4233    4.7180    0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135    2.5187    1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0226   -1.4689    2.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253   -3.8351    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -3.1573   -1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1394   -1.1976   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3326   -1.4653   -1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299   -2.3198    0.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 19  4  1  0
 10  5  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
M  END


  Mrv1652309072111402D          

 20 23  0  0  0  0            999 V2000
    3.8037    3.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    2.2066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362    1.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912    0.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    0.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4711    1.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9120    0.2172    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -0.8703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  4 20  1  0  0  0  0
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242748

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CC2C(C1)C1=C(OC3=CC=CC=C23)C=CC(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16ClNO/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19/h2-8,14-15H,9-10H2,1H3

> <INCHI_KEY>
VSWBSWWIRNCQIJ-UHFFFAOYSA-N

> <FORMULA>
C17H16ClNO

> <MOLECULAR_WEIGHT>
285.77

> <EXACT_MASS>
285.0920418

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.32714445480903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(14),7,9,11,15,17-hexaene

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
3.7246065736666667

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.29386587049297

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
81.64990000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(14),7,9,11,15,17-hexaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0242748
     RDKit          3D
Asenapine
 36 39  0  0  0  0  0  0  0  0999 V2000
    3.6192   -0.4880    0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817   -0.3114    0.3347 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9063    0.8674   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    0.6548   -1.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3844    1.5933   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2561    2.8476   -0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9791    3.9109   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8774    3.8362    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201    2.5986    1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    1.5178    0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557    0.3539    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5190   -0.9728    0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3854   -1.8187    1.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4537   -3.1451    1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324   -3.5879    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7356   -5.2851   -0.2451 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7840   -2.7372   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6853   -1.3819   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3096   -0.7733   -0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663   -1.3636   -0.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0536    0.3598    0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0926   -0.5839   -0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8411   -1.4036    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9780    1.8024    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566    0.8728   -1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949    0.9893   -2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4453    2.9709   -1.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509    4.8838   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4233    4.7180    0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135    2.5187    1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0226   -1.4689    2.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253   -3.8351    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -3.1573   -1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1394   -1.1976   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3326   -1.4653   -1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299   -2.3198    0.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 19  4  1  0
 10  5  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 07-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-21         0                                  
HETATM    1  C   UNK     0       7.100   5.659   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.100   4.119   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.854   3.214   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.330   1.749   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.870   1.749   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.346   3.214   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.830   0.545   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.488  -0.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.617  -2.004   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.088  -1.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.431  -0.048   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.302   0.999   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      12.902   0.405   0.000  0.00  0.00          Cl+0
HETATM   14  O   UNK     0       7.100  -1.625   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.713  -0.956   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.584  -2.004   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.112  -1.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.770  -0.048   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.898   0.999   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.370   0.545   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    4   15                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0242748
HETATM    1  C1  UNL     1       3.619  -0.488   0.424  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.182  -0.311   0.335  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.906   0.867  -0.469  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.496   0.655  -1.040  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.384   1.593  -0.386  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.256   2.848  -0.981  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.979   3.911  -0.544  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.877   3.836   0.499  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.020   2.599   1.104  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.281   1.518   0.655  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.556   0.354   1.383  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.519  -0.973   0.916  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.385  -1.819   1.565  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.454  -3.145   1.209  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.632  -3.588   0.193  1.00  0.00           C  
HETATM   16 CL1  UNL     1      -1.736  -5.285  -0.245  1.00  0.00          CL  
HETATM   17  C14 UNL     1      -0.784  -2.737  -0.435  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.685  -1.382  -0.102  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.310  -0.773  -0.961  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.666  -1.364  -0.530  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.054   0.360   0.974  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.093  -0.584  -0.576  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.841  -1.404   1.017  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.978   1.802   0.094  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.657   0.873  -1.274  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.595   0.989  -2.121  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.445   2.971  -1.819  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.851   4.884  -1.038  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.423   4.718   0.800  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.714   2.519   1.917  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.023  -1.469   2.355  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.125  -3.835   1.701  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.158  -3.157  -1.236  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.139  -1.198  -1.998  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.333  -1.465  -1.393  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.530  -2.320   0.007  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   20
CONECT    3    4   24   25
CONECT    4    5   19   26
CONECT    5    6    6   10
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11
CONECT   11   12
CONECT   12   13   13   18
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16   17
CONECT   17   18   18   33
CONECT   18   19
CONECT   19   20   34
CONECT   20   35   36
END

HMDB0242748
     RDKit          3D
Asenapine
 36 39  0  0  0  0  0  0  0  0999 V2000
    3.6192   -0.4880    0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817   -0.3114    0.3347 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9063    0.8674   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    0.6548   -1.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3844    1.5933   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2561    2.8476   -0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9791    3.9109   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8774    3.8362    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201    2.5986    1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    1.5178    0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557    0.3539    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5190   -0.9728    0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3854   -1.8187    1.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4537   -3.1451    1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324   -3.5879    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7356   -5.2851   -0.2451 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7840   -2.7372   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6853   -1.3819   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3096   -0.7733   -0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663   -1.3636   -0.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0536    0.3598    0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0926   -0.5839   -0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8411   -1.4036    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9780    1.8024    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566    0.8728   -1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949    0.9893   -2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4453    2.9709   -1.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509    4.8838   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4233    4.7180    0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135    2.5187    1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0226   -1.4689    2.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253   -3.8351    1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582   -3.1573   -1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1394   -1.1976   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3326   -1.4653   -1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299   -2.3198    0.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 19  4  1  0
 10  5  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3-6,7)oxepino(4,5-c)pyrrole	MeSH
Secuado	MeSH
Asenapine maleate	MeSH
Saphris	MeSH
trans-5-Chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole	MeSH

Chemical Formula

C₁₇H₁₆ClNO

Average Molecular Weight

285.77

Monoisotopic Molecular Weight

285.0920418

IUPAC Name

17-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(14),7,9,11,15,17-hexaene

Traditional Name

17-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(14),7,9,11,15,17-hexaene

CAS Registry Number

Not Available

SMILES

CN1CC2C(C1)C1=C(OC3=CC=CC=C23)C=CC(Cl)=C1

InChI Identifier

InChI=1S/C17H16ClNO/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19/h2-8,14-15H,9-10H2,1H3

InChI Key

VSWBSWWIRNCQIJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Dibenzoxepines

Direct Parent

Dibenzoxepines

Alternative Parents

Substituents

Dibenzoxepine
Diaryl ether
Aralkylamine
Aryl chloride
Aryl halide
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Ether
Organopnictogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:71255 )
organic heterotetracyclic compound (CHEBI:71255 )
organochlorine compound (CHEBI:71255 )
cyclic ether (CHEBI:71255 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	4.35	ALOGPS
logP	3.72	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	7.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.65 m³·mol⁻¹	ChemAxon
Polarizability	30.33 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	198.247	30932474
DeepCCS	[M+Na]+	173.812	30932474
AllCCS	[M+H]+	163.7	32859911
AllCCS	[M+H-H2O]+	159.9	32859911
AllCCS	[M+NH4]+	167.2	32859911
AllCCS	[M+Na]+	168.2	32859911
AllCCS	[M-H]-	170.2	32859911
AllCCS	[M+Na-2H]-	169.4	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Asenapine	CN1CC2C(C1)C1=C(OC3=CC=CC=C23)C=CC(Cl)=C1	3126.0	Standard polar	33892256
Asenapine	CN1CC2C(C1)C1=C(OC3=CC=CC=C23)C=CC(Cl)=C1	2253.0	Standard non polar	33892256
Asenapine	CN1CC2C(C1)C1=C(OC3=CC=CC=C23)C=CC(Cl)=C1	2246.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Asenapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1190000000-16cc2475dce76f72bfa6	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Asenapine 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 - Asenapine 10V, Positive-QTOF	splash10-000i-0090000000-228d2ec1440235f0cf56	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asenapine 20V, Positive-QTOF	splash10-000i-0090000000-a209b80bba7c44b542b7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asenapine 40V, Positive-QTOF	splash10-0006-5590000000-12e0b991d416ef0ace14	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asenapine 10V, Negative-QTOF	splash10-001i-0090000000-ea3640af929ec1393b86	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asenapine 20V, Negative-QTOF	splash10-001i-3090000000-a02ccc53cb6e6b96a64d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asenapine 40V, Negative-QTOF	splash10-001i-9040000000-e7fae4268a019fee1398	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

8079624

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

71255

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Asenapine (HMDB0242748)

MOL for HMDB0242748 (Asenapine)

3D MOL for HMDB0242748 (Asenapine)

3D SDF for HMDB0242748 (Asenapine)

3D-SDF for HMDB0242748 (Asenapine)

PDB for HMDB0242748 (Asenapine)

3D PDB for HMDB0242748 (Asenapine)

SMILES for HMDB0242748 (Asenapine)

INCHI for HMDB0242748 (Asenapine)

Structure for HMDB0242748 (Asenapine)

3D Structure for HMDB0242748 (Asenapine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra