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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:08:59 UTC

Update Date

2019-07-23 07:15:26 UTC

HMDB ID

HMDB0060948

Secondary Accession Numbers

HMDB60948

Metabolite Identification

Common Name

desmethylcyclobenzaprine

Description

desmethylcyclobenzaprine is a metabolite of cyclobenzaprine. Cyclobenzaprine, brand name Flexeril, is a muscle relaxant medication used to relieve skeletal muscle spasms and associated pain in acute musculoskeletal conditions. It is the most well-studied drug for this application, and it also has been used off-label for fibromyalgia treatment. A new bedtime formulation of cyclobenzaprine is under development for the management of fibromyalgia syndrome. (Wikipedia)

Structure

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

HMDB0060948
     RDKit          3D
desmethylcyclobenzaprine
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.2628    0.1202    0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1882   -0.4766   -0.4258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932    0.2699   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -0.2656   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    0.5239   -0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    0.1995   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4815    1.3481    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8516    2.4763    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276    3.6190    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891    3.5404    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5743    2.3725   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8320    1.2254   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6033    0.0703   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760   -1.2377   -0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0319   -1.8161   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1530   -3.1507    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026   -3.8261    0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0670   -3.1317    1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2129   -1.8106    0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414   -1.1906    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1800   -0.5248    0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5199    1.1072   -0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667    0.2629    1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4075   -0.4132   -1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1015    1.3348   -0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061    0.3901    0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -0.0319   -2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7113   -1.3359   -0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836    1.5712   -0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077    2.4322    0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490    4.5239    1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542    4.4548    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562    2.3536   -0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5522    0.3242   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9573   -1.9504   -1.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0913   -3.6427    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -4.8689    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9242   -3.6239    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864   -1.2228    1.0613 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  3
  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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

924
  Mrv0541 02271201042D          

 20 22  0  0  0  0            999 V2000
    2.5991   -1.7284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0279    0.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7710    1.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2845    1.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3134   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0279   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9546    1.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010    1.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4402    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6154    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3918    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7715    2.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2840    2.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2147    0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408    0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4059    1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991   -2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  2  0  0  0  0
  3  8  1  0  0  0  0
  3 12  2  0  0  0  0
  4  9  1  0  0  0  0
  4 13  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8 10  1  0  0  0  0
  8 14  2  0  0  0  0
  9 11  1  0  0  0  0
  9 15  2  0  0  0  0
 10 11  2  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060948

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H19N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-13,20H,6,14H2,1H3

> <INCHI_KEY>
XECQQDXTQRYYBH-UHFFFAOYSA-N

> <FORMULA>
C19H19N

> <MOLECULAR_WEIGHT>
261.3609

> <EXACT_MASS>
261.151749613

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
30.955693588396272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}propyl)amine

> <ALOGPS_LOGP>
4.43

> <JCHEM_LOGP>
4.229965321

> <ALOGPS_LOGS>
-5.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.471608822292016

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
97.32910000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.95e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}propyl)amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060948
     RDKit          3D
desmethylcyclobenzaprine
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.2628    0.1202    0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1882   -0.4766   -0.4258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932    0.2699   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -0.2656   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    0.5239   -0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    0.1995   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4815    1.3481    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8516    2.4763    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276    3.6190    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891    3.5404    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5743    2.3725   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8320    1.2254   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6033    0.0703   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760   -1.2377   -0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0319   -1.8161   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1530   -3.1507    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026   -3.8261    0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0670   -3.1317    1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2129   -1.8106    0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414   -1.1906    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1800   -0.5248    0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5199    1.1072   -0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667    0.2629    1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4075   -0.4132   -1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1015    1.3348   -0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061    0.3901    0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -0.0319   -2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7113   -1.3359   -0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836    1.5712   -0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077    2.4322    0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490    4.5239    1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542    4.4548    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562    2.3536   -0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5522    0.3242   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9573   -1.9504   -1.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0913   -3.6427    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -4.8689    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9242   -3.6239    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864   -1.2228    1.0613 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  3
  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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 924                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  N   UNK     0       4.852  -3.226   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       7.519   1.393   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.906   2.061   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.131   2.061   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.185  -0.917   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.519  -0.147   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.185  -2.456   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.249   3.562   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.789   3.562   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.288   4.766   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.749   4.766   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.065   0.952   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.973   0.952   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.774   4.058   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.263   4.058   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.601   1.413   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.436   1.413   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.958   2.977   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080   2.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.852  -4.766   0.000  0.00  0.00           C+0
CONECT    1    7   20                                                       
CONECT    2    3    4    6                                                  
CONECT    3    2    8   12                                                  
CONECT    4    2    9   13                                                  
CONECT    5    6    7                                                       
CONECT    6    2    5                                                       
CONECT    7    1    5                                                       
CONECT    8    3   10   14                                                  
CONECT    9    4   11   15                                                  
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    3   16                                                       
CONECT   13    4   17                                                       
CONECT   14    8   18                                                       
CONECT   15    9   19                                                       
CONECT   16   12   18                                                       
CONECT   17   13   19                                                       
CONECT   18   14   16                                                       
CONECT   19   15   17                                                       
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0060948
HETATM    1  C1  UNL     1       5.263   0.120   0.335  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.188  -0.477  -0.426  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.993   0.270  -0.158  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.783  -0.266  -0.906  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.617   0.524  -0.589  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.516   0.200  -0.119  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.482   1.348   0.054  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.852   2.476   0.487  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.628   3.619   0.674  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.989   3.540   0.409  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.574   2.372  -0.027  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.832   1.225  -0.221  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.603   0.070  -0.695  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.276  -1.238  -0.639  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.032  -1.816  -0.071  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.153  -3.151   0.274  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.103  -3.826   0.887  1.00  0.00           C  
HETATM   18  C17 UNL     1       0.067  -3.132   1.146  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.213  -1.811   0.816  1.00  0.00           C  
HETATM   20  C19 UNL     1      -0.841  -1.191   0.212  1.00  0.00           C  
HETATM   21  H1  UNL     1       6.180  -0.525   0.294  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.520   1.107  -0.121  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.967   0.263   1.395  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.408  -0.413  -1.445  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.101   1.335  -0.530  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.806   0.390   0.924  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.118  -0.032  -2.023  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.711  -1.336  -0.992  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.884   1.571  -0.841  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.208   2.432   0.673  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.149   4.524   1.016  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.554   4.455   0.569  1.00  0.00           H  
HETATM   33  H13 UNL     1      -4.656   2.354  -0.226  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.552   0.324  -1.136  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.957  -1.950  -1.032  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.091  -3.643   0.048  1.00  0.00           H  
HETATM   37  H17 UNL     1      -1.197  -4.869   1.155  1.00  0.00           H  
HETATM   38  H18 UNL     1       0.924  -3.624   1.629  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.086  -1.223   1.061  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6    6   29
CONECT    6    7   20
CONECT    7    8    8   12
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13
CONECT   13   14   14   34
CONECT   14   15   35
CONECT   15   16   16   20
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19   38
CONECT   19   20   20   39
END

HMDB0060948
     RDKit          3D
desmethylcyclobenzaprine
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.2628    0.1202    0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1882   -0.4766   -0.4258 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932    0.2699   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -0.2656   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    0.5239   -0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    0.1995   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4815    1.3481    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8516    2.4763    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276    3.6190    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891    3.5404    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5743    2.3725   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8320    1.2254   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6033    0.0703   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760   -1.2377   -0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0319   -1.8161   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1530   -3.1507    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026   -3.8261    0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0670   -3.1317    1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2129   -1.8106    0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414   -1.1906    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1800   -0.5248    0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5199    1.1072   -0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667    0.2629    1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4075   -0.4132   -1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1015    1.3348   -0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061    0.3901    0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -0.0319   -2.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7113   -1.3359   -0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836    1.5712   -0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077    2.4322    0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1490    4.5239    1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542    4.4548    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562    2.3536   -0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5522    0.3242   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9573   -1.9504   -1.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0913   -3.6427    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -4.8689    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9242   -3.6239    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864   -1.2228    1.0613 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  3
  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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Fluorobenzoylpropionate	HMDB

Chemical Formula

C₁₉H₁₉N

Average Molecular Weight

261.3609

Monoisotopic Molecular Weight

261.151749613

IUPAC Name

methyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}propyl)amine

Traditional Name

methyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}propyl)amine

CAS Registry Number

Not Available

SMILES

CNCCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H19N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-13,20H,6,14H2,1H3

InChI Key

XECQQDXTQRYYBH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Dibenzocycloheptenes

Sub Class

Not Available

Direct Parent

Dibenzocycloheptenes

Alternative Parents

Substituents

Dibenzocycloheptene
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060948)

Organ

Kidney (HMDB: HMDB0060948)
Liver (HMDB: HMDB0060948)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060948)

Cellular substructure

Cytoplasm (HMDB: HMDB0060948)
Membrane (HMDB: HMDB0060948)

Source

Endogenous

Endogenous (HMDB: HMDB0060948)

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	0.001 g/L	ALOGPS
logP	4.43	ALOGPS
logP	4.23	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	10.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.33 m³·mol⁻¹	ChemAxon
Polarizability	30.96 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	163.288	31661259
DarkChem	[M-H]-	163.613	31661259
DeepCCS	[M-2H]-	191.713	30932474
DeepCCS	[M+Na]+	167.279	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	166.4	32859911
AllCCS	[M+Na]+	167.4	32859911
AllCCS	[M-H]-	170.0	32859911
AllCCS	[M+Na-2H]-	169.5	32859911
AllCCS	[M+HCOO]-	169.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.43 minutes	32390414
Predicted by Siyang on May 30, 2022	12.423 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.24 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1926.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	311.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	173.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	167.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	472.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	475.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	280.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1213.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	439.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1230.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	300.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	231.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
desmethylcyclobenzaprine	CNCCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12	3186.9	Standard polar	33892256
desmethylcyclobenzaprine	CNCCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12	2374.1	Standard non polar	33892256
desmethylcyclobenzaprine	CNCCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12	2325.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
desmethylcyclobenzaprine,1TMS,isomer #1	CN(CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12)[Si](C)(C)C	2498.7	Semi standard non polar	33892256
desmethylcyclobenzaprine,1TMS,isomer #1	CN(CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12)[Si](C)(C)C	2589.8	Standard non polar	33892256
desmethylcyclobenzaprine,1TMS,isomer #1	CN(CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12)[Si](C)(C)C	3380.4	Standard polar	33892256
desmethylcyclobenzaprine,1TBDMS,isomer #1	CN(CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2707.7	Semi standard non polar	33892256
desmethylcyclobenzaprine,1TBDMS,isomer #1	CN(CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2794.7	Standard non polar	33892256
desmethylcyclobenzaprine,1TBDMS,isomer #1	CN(CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3486.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - desmethylcyclobenzaprine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9040000000-4db15d9de08e8b166584	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - desmethylcyclobenzaprine 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 - desmethylcyclobenzaprine 10V, Positive-QTOF	splash10-03e9-0090000000-6ef8f0c6d1b477f89e84	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 20V, Positive-QTOF	splash10-01q9-2090000000-031ef29dfa9ce6a8f128	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 40V, Positive-QTOF	splash10-0uxu-9680000000-ad6966006cf8bd900e02	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 10V, Negative-QTOF	splash10-03di-0090000000-e494a1413ec61e39abae	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 20V, Negative-QTOF	splash10-03di-0090000000-76df773236b39d51b397	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 40V, Negative-QTOF	splash10-001i-2090000000-23239cc43d277e8a8b59	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 10V, Positive-QTOF	splash10-03di-0090000000-0d299f046e5a4471e86b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 20V, Positive-QTOF	splash10-03di-0090000000-b1a26421e701a9108faa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 40V, Positive-QTOF	splash10-0zfr-0190000000-cf9e93a74ccb274bf59b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 10V, Negative-QTOF	splash10-03di-0090000000-3092a98ff8ef390e6a18	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 20V, Negative-QTOF	splash10-03di-0090000000-2594b9a8e93e98f076e5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - desmethylcyclobenzaprine 40V, Negative-QTOF	splash10-1000-0090000000-d222bde9db7beb6baa3d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

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

9531

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2758337

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 desmethylcyclobenzaprine (HMDB0060948)

MOL for HMDB0060948 (desmethylcyclobenzaprine)

3D MOL for HMDB0060948 (desmethylcyclobenzaprine)

3D SDF for HMDB0060948 (desmethylcyclobenzaprine)

3D-SDF for HMDB0060948 (desmethylcyclobenzaprine)

PDB for HMDB0060948 (desmethylcyclobenzaprine)

3D PDB for HMDB0060948 (desmethylcyclobenzaprine)

SMILES for HMDB0060948 (desmethylcyclobenzaprine)

INCHI for HMDB0060948 (desmethylcyclobenzaprine)

Structure for HMDB0060948 (desmethylcyclobenzaprine)

3D Structure for HMDB0060948 (desmethylcyclobenzaprine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra