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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015060

Secondary Accession Numbers

HMDB15060

Metabolite Identification

Common Name

Cyclobenzaprine

Description

Cyclobenzaprine is a skeletal muscle relaxant and a central nervous system (CNS) depressant. Cyclobenzaprine acts on the locus coeruleus where it results in increased norepinephrine release, potentially through the gamma fibers which innervate and inhibit the alpha motor neurons in the ventral horn of the spinal cord. It is structurally similar to Amitriptyline, differing by only one double bond.

Structure

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

HMDB0015060
     RDKit          3D
Cyclobenzaprine
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.0726    0.4577    0.8447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -0.2007   -0.2064 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0410   -1.2376   -0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649    0.7460   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654    1.3988   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6743    0.3056    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931    0.1436    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1344   -1.1541    0.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4097   -1.6191    1.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7745   -2.8113    2.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527   -3.5243    1.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804   -3.0469    0.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166   -1.8516    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816   -1.4840   -0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2775   -0.2757   -1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6483    0.9817   -1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3862    2.0557   -1.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627    3.3243   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151    3.4828   -0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651    2.4149    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5006    1.1732   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5120    0.4228    1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855    1.5179    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0330   -0.0527    0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0134   -1.4283   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837   -2.2106   -0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2796   -1.0697   -1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3028    1.5092   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316    0.1791   -1.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475    1.9351    0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1071    2.1126   -0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2586   -0.5475    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -1.0395    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -3.2130    3.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1370   -4.4793    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4263   -3.5640    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6406   -2.2661   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491   -0.2109   -2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2763    1.9521   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5017    4.2136   -1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4678    4.4667    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2074    2.4936    0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  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 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

924
  Mrv0541 02231215062D          

 21 23  0  0  0  0            999 V2000
    2.5993   -1.7285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0282    0.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7714    1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2848    1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0282   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550    1.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1013    1.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6157    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3922    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6641    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7720    2.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2842    2.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2152    0.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410    0.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4064    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    1.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5993   -2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848   -1.3160    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
  1 21  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>
HMDB0015060

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H21N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-14H,7,15H2,1-2H3

> <INCHI_KEY>
JURKNVYFZMSNLP-UHFFFAOYSA-N

> <FORMULA>
C20H21N

> <MOLECULAR_WEIGHT>
275.3874

> <EXACT_MASS>
275.167399677

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
32.94643176140032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.73

> <JCHEM_LOGP>
4.613013258333333

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.76073861606049

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
102.62380000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclobenzaprine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015060
     RDKit          3D
Cyclobenzaprine
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.0726    0.4577    0.8447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -0.2007   -0.2064 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0410   -1.2376   -0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649    0.7460   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654    1.3988   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6743    0.3056    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931    0.1436    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1344   -1.1541    0.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4097   -1.6191    1.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7745   -2.8113    2.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527   -3.5243    1.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804   -3.0469    0.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166   -1.8516    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816   -1.4840   -0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2775   -0.2757   -1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6483    0.9817   -1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3862    2.0557   -1.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627    3.3243   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151    3.4828   -0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651    2.4149    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5006    1.1732   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5120    0.4228    1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855    1.5179    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0330   -0.0527    0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0134   -1.4283   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837   -2.2106   -0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2796   -1.0697   -1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3028    1.5092   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316    0.1791   -1.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475    1.9351    0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1071    2.1126   -0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2586   -0.5475    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -1.0395    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -3.2130    3.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1370   -4.4793    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4263   -3.5640    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6406   -2.2661   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491   -0.2109   -2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2763    1.9521   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5017    4.2136   -1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4678    4.4667    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2074    2.4936    0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  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 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 924                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-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       8.907   2.061   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.132   2.061   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.186  -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  -2.457   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       8.289   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   4.059   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.264   4.059   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.602   1.413   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.437   1.413   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.959   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
HETATM   21  C   UNK     0       3.518  -2.457   0.000  0.00  0.00           C+0
CONECT    1    7   20   21                                                  
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                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0015060
HETATM    1  C1  UNL     1       4.073   0.458   0.845  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.317  -0.201  -0.206  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.041  -1.238  -0.866  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.665   0.746  -1.070  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.565   1.399  -0.160  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.674   0.306   0.261  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.593   0.144   0.239  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.134  -1.154   0.759  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.410  -1.619   1.818  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.774  -2.811   2.382  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.853  -3.524   1.889  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.580  -3.047   0.819  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.217  -1.852   0.251  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.082  -1.484  -0.894  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.277  -0.276  -1.455  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.648   0.982  -1.029  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.386   2.056  -1.448  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.963   3.324  -1.075  1.00  0.00           C  
HETATM   19  C18 UNL     1      -1.815   3.483  -0.292  1.00  0.00           C  
HETATM   20  C19 UNL     1      -1.065   2.415   0.136  1.00  0.00           C  
HETATM   21  C20 UNL     1      -1.501   1.173  -0.249  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.512   0.423   1.811  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.186   1.518   0.535  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.033  -0.053   0.976  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.013  -1.428  -0.323  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.484  -2.211  -0.743  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.280  -1.070  -1.920  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.303   1.509  -1.510  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.132   0.179  -1.857  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.048   1.935   0.657  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.107   2.113  -0.861  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.259  -0.548   0.668  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.428  -1.040   2.201  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.213  -3.213   3.232  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.137  -4.479   2.348  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.426  -3.564   0.399  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.641  -2.266  -1.356  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.949  -0.211  -2.284  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.276   1.952  -2.051  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.502   4.214  -1.374  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.468   4.467   0.012  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.207   2.494   0.786  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4
CONECT    3   25   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7    7   32
CONECT    7    8   21
CONECT    8    9    9   13
CONECT    9   10   33
CONECT   10   11   11   34
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   14
CONECT   14   15   15   37
CONECT   15   16   38
CONECT   16   17   17   21
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   20   41
CONECT   20   21   21   42
END

HMDB0015060
     RDKit          3D
Cyclobenzaprine
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.0726    0.4577    0.8447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -0.2007   -0.2064 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0410   -1.2376   -0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649    0.7460   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654    1.3988   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6743    0.3056    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931    0.1436    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1344   -1.1541    0.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4097   -1.6191    1.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7745   -2.8113    2.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527   -3.5243    1.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804   -3.0469    0.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166   -1.8516    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816   -1.4840   -0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2775   -0.2757   -1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6483    0.9817   -1.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3862    2.0557   -1.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627    3.3243   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151    3.4828   -0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651    2.4149    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5006    1.1732   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5120    0.4228    1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855    1.5179    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0330   -0.0527    0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0134   -1.4283   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837   -2.2106   -0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2796   -1.0697   -1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3028    1.5092   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316    0.1791   -1.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475    1.9351    0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1071    2.1126   -0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2586   -0.5475    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -1.0395    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -3.2130    3.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1370   -4.4793    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4263   -3.5640    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6406   -2.2661   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491   -0.2109   -2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2763    1.9521   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5017    4.2136   -1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4678    4.4667    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2074    2.4936    0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  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 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3-Dibenzo[a,D]cyclohepten-5-ylidene-propyl)-dimethyl-amine	ChEBI
Ciclobenzaprina	ChEBI
Cyclobenzaprinum	ChEBI
N,N-Dimethyl-5H-dibenzo(a,D)cycloheptene-Delta(5,gamma)-propylamine	ChEBI
N,N-Dimethyl-5H-dibenzo(a,D)cycloheptene-delta(5,g)-propylamine	Generator
N,N-Dimethyl-5H-dibenzo(a,D)cycloheptene-δ(5,γ)-propylamine	Generator
N,N-Dimethyl-5H-dibenzo(a,D)cycloheptene-δ(5,g)-propylamine	HMDB
Cyclobenzaprine HCL	HMDB
Flexeril	HMDB
Lisseril	HMDB
Cyclobenzaprine hydrochloride	HMDB

Chemical Formula

C₂₀H₂₁N

Average Molecular Weight

275.3874

Monoisotopic Molecular Weight

275.167399677

IUPAC Name

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

Traditional Name

cyclobenzaprine

CAS Registry Number

303-53-7

SMILES

CN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C20H21N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-14H,7,15H2,1-2H3

InChI Key

JURKNVYFZMSNLP-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
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

organic tricyclic compound (CHEBI:3996 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015060)

Source

Exogenous

Exogenous (HMDB: HMDB0015060)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	216 - 218 °C (hydrochloride salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0069 g/L	Not Available
LogP	5.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	164.7	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0069 g/L	ALOGPS
logP	4.73	ALOGPS
logP	4.61	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.62 m³·mol⁻¹	ChemAxon
Polarizability	32.95 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]+	166.895	31661259
DarkChem	[M-H]-	168.298	31661259
DeepCCS	[M-2H]-	193.884	30932474
DeepCCS	[M+Na]+	169.449	30932474
AllCCS	[M+H]+	166.2	32859911
AllCCS	[M+H-H2O]+	162.6	32859911
AllCCS	[M+NH4]+	169.6	32859911
AllCCS	[M+Na]+	170.5	32859911
AllCCS	[M-H]-	174.9	32859911
AllCCS	[M+Na-2H]-	174.4	32859911
AllCCS	[M+HCOO]-	173.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclobenzaprine	CN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12	3146.1	Standard polar	33892256
Cyclobenzaprine	CN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12	2265.1	Standard non polar	33892256
Cyclobenzaprine	CN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12	2250.9	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 - Cyclobenzaprine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9040000000-6d92a6b3b68f574cfa96	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclobenzaprine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclobenzaprine 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 - Cyclobenzaprine 10V, Positive-QTOF	splash10-004i-0090000000-b82bb6864d1db9590238	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 20V, Positive-QTOF	splash10-003r-2190000000-d7ca012a9442c5c5159d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 40V, Positive-QTOF	splash10-0f6x-9860000000-d6cd399a2bc4bff340b6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 10V, Negative-QTOF	splash10-00di-0090000000-2ec20dd7f67cc51c9e31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 20V, Negative-QTOF	splash10-00di-1090000000-6688ebb97b5d79eca312	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 40V, Negative-QTOF	splash10-002f-7290000000-87d189310c604e77fbc2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 10V, Positive-QTOF	splash10-004i-0090000000-93624eb06b890930f701	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 20V, Positive-QTOF	splash10-004i-0090000000-204146569caae8c2b6be	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 40V, Positive-QTOF	splash10-0a4i-3090000000-443350b9631b31aaa21c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 10V, Negative-QTOF	splash10-00di-0090000000-639559d845843ccd499a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 20V, Negative-QTOF	splash10-00di-0090000000-96cd6df79ac93f81d7ae	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclobenzaprine 40V, Negative-QTOF	splash10-014i-0090000000-e16ad7a8e7b878d6be95	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB00924	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00924	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00924

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2792

KEGG Compound ID

C06931

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyclobenzaprine

METLIN ID

Not Available

PubChem Compound

2895

PDB ID

Not Available

ChEBI ID

3996

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

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Wang RW, Liu L, Cheng H: Identification of human liver cytochrome P450 isoforms involved in the in vitro metabolism of cyclobenzaprine. Drug Metab Dispos. 1996 Jul;24(7):786-91. [PubMed:8818577 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Wang RW, Liu L, Cheng H: Identification of human liver cytochrome P450 isoforms involved in the in vitro metabolism of cyclobenzaprine. Drug Metab Dispos. 1996 Jul;24(7):786-91. [PubMed:8818577 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Honda M, Nishida T, Ono H: Tricyclic analogs cyclobenzaprine, amitriptyline and cyproheptadine inhibit the spinal reflex transmission through 5-HT(2) receptors. Eur J Pharmacol. 2003 Jan 1;458(1-2):91-9. [PubMed:12498911 ]
Kobayashi H, Hasegawa Y, Ono H: Cyclobenzaprine, a centrally acting muscle relaxant, acts on descending serotonergic systems. Eur J Pharmacol. 1996 Sep 5;311(1):29-35. [PubMed:8884233 ]

Showing metabocard for Cyclobenzaprine (HMDB0015060)

MOL for HMDB0015060 (Cyclobenzaprine)

3D MOL for HMDB0015060 (Cyclobenzaprine)

3D SDF for HMDB0015060 (Cyclobenzaprine)

3D-SDF for HMDB0015060 (Cyclobenzaprine)

PDB for HMDB0015060 (Cyclobenzaprine)

3D PDB for HMDB0015060 (Cyclobenzaprine)

SMILES for HMDB0015060 (Cyclobenzaprine)

INCHI for HMDB0015060 (Cyclobenzaprine)

Structure for HMDB0015060 (Cyclobenzaprine)

3D Structure for HMDB0015060 (Cyclobenzaprine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References