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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:36:24 UTC

Update Date

2022-03-07 02:53:52 UTC

HMDB ID

HMDB0033832

Secondary Accession Numbers

HMDB33832

Metabolite Identification

Common Name

Cinnamyl cinnamate

Description

Cinnamyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Cinnamyl cinnamate is a sweet, almond, and balsam tasting compound. Based on a literature review very few articles have been published on Cinnamyl cinnamate.

Structure

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

HMDB0033832
     RDKit          3D
Cinnamyl cinnamate
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.8622   -0.8918   -0.2259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4649   -0.1718    0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    0.5810    1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4260    0.7208    1.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058    0.1449    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6130   -0.2659    1.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6928   -0.7212    0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6449   -0.7997   -0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4900   -0.4080   -1.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3887    0.0600   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -0.0836    0.7536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7258   -0.7984   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1728   -0.5855    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -0.0519   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3593    0.1993   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0619   -0.1114    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    0.1292    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950    0.6953   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4085    1.0161   -1.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0504    0.7756   -1.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5582    1.1390    2.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8005    1.3540    2.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6557   -0.2062    2.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6060   -1.0295    1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4903   -1.1587   -1.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4136   -0.4552   -2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635    0.4204   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285   -1.8911   -0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076   -0.4637   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6159   -0.8701    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075    0.2171   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5795   -0.5526    1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9902   -0.1157    1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1499    0.8959   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8993    1.4700   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4589    1.0040   -2.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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
  2 11  1  0
 11 12  1  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
 10  5  1  0
 20 15  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END


  Mrv0541 05061307232D          

 20 21  0  0  0  0            999 V2000
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  7  2  0  0  0  0
 14 13  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
 17 10  2  0  0  0  0
 17 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  1  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033832

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(OC\C=C\C1=CC=CC=C1)\C=C/C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O2/c19-18(14-13-17-10-5-2-6-11-17)20-15-7-12-16-8-3-1-4-9-16/h1-14H,15H2/b12-7+,14-13-

> <INCHI_KEY>
NQBWNECTZUOWID-QSYVVUFSSA-N

> <FORMULA>
C18H16O2

> <MOLECULAR_WEIGHT>
264.3184

> <EXACT_MASS>
264.115029756

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
30.477305747363776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-phenylprop-2-en-1-yl (2Z)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
4.849702440000001

> <ALOGPS_LOGS>
-5.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.818200756969904

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
82.76019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.26e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-phenylprop-2-en-1-yl (2Z)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033832
     RDKit          3D
Cinnamyl cinnamate
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.8622   -0.8918   -0.2259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4649   -0.1718    0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    0.5810    1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4260    0.7208    1.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058    0.1449    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6130   -0.2659    1.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6928   -0.7212    0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6449   -0.7997   -0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4900   -0.4080   -1.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3887    0.0600   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -0.0836    0.7536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7258   -0.7984   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1728   -0.5855    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -0.0519   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3593    0.1993   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0619   -0.1114    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    0.1292    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950    0.6953   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4085    1.0161   -1.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0504    0.7756   -1.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5582    1.1390    2.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8005    1.3540    2.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6557   -0.2062    2.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6060   -1.0295    1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4903   -1.1587   -1.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4136   -0.4552   -2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635    0.4204   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285   -1.8911   -0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076   -0.4637   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6159   -0.8701    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075    0.2171   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5795   -0.5526    1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9902   -0.1157    1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1499    0.8959   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8993    1.4700   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4589    1.0040   -2.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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
  2 11  1  0
 11 12  1  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
 10  5  1  0
 20 15  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    8                                                       
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7   12   15                                                       
CONECT    8    3   16                                                       
CONECT    9    4   16                                                       
CONECT   10    5   17                                                       
CONECT   11    6   17                                                       
CONECT   12    7   16                                                       
CONECT   13   14   17                                                       
CONECT   14   13   18                                                       
CONECT   15    7   20                                                       
CONECT   16    8    9   12                                                  
CONECT   17   10   11   13                                                  
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   15   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0033832
HETATM    1  O1  UNL     1      -1.862  -0.892  -0.226  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.465  -0.172   0.691  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.145   0.581   1.689  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.426   0.721   1.825  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.406   0.145   0.959  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.613  -0.266   1.563  1.00  0.00           C  
HETATM    7  C6  UNL     1      -6.693  -0.721   0.853  1.00  0.00           C  
HETATM    8  C7  UNL     1      -6.645  -0.800  -0.519  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.490  -0.408  -1.145  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.389   0.060  -0.396  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.042  -0.084   0.754  1.00  0.00           O  
HETATM   12  C10 UNL     1       0.726  -0.798  -0.200  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.173  -0.586   0.020  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.916  -0.052  -0.919  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.359   0.199  -0.795  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.062  -0.111   0.338  1.00  0.00           C  
HETATM   17  C15 UNL     1       6.436   0.129   0.452  1.00  0.00           C  
HETATM   18  C16 UNL     1       7.095   0.695  -0.611  1.00  0.00           C  
HETATM   19  C17 UNL     1       6.408   1.016  -1.761  1.00  0.00           C  
HETATM   20  C18 UNL     1       5.050   0.776  -1.867  1.00  0.00           C  
HETATM   21  H1  UNL     1      -1.558   1.139   2.477  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.801   1.354   2.705  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.656  -0.206   2.648  1.00  0.00           H  
HETATM   24  H4  UNL     1      -7.606  -1.030   1.343  1.00  0.00           H  
HETATM   25  H5  UNL     1      -7.490  -1.159  -1.089  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.414  -0.455  -2.225  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.563   0.420  -0.981  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.528  -1.891  -0.090  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.408  -0.464  -1.195  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.616  -0.870   0.955  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.408   0.217  -1.849  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.579  -0.553   1.183  1.00  0.00           H  
HETATM   33  H13 UNL     1       6.990  -0.116   1.346  1.00  0.00           H  
HETATM   34  H14 UNL     1       8.150   0.896  -0.563  1.00  0.00           H  
HETATM   35  H15 UNL     1       6.899   1.470  -2.633  1.00  0.00           H  
HETATM   36  H16 UNL     1       4.459   1.004  -2.739  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   21
CONECT    4    5   22
CONECT    5    6    6   10
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   27
CONECT   11   12
CONECT   12   13   28   29
CONECT   13   14   14   30
CONECT   14   15   31
CONECT   15   16   16   20
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   18   19   34
CONECT   19   20   20   35
CONECT   20   36
END

HMDB0033832
     RDKit          3D
Cinnamyl cinnamate
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.8622   -0.8918   -0.2259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4649   -0.1718    0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    0.5810    1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4260    0.7208    1.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058    0.1449    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6130   -0.2659    1.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6928   -0.7212    0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6449   -0.7997   -0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4900   -0.4080   -1.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3887    0.0600   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -0.0836    0.7536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7258   -0.7984   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1728   -0.5855    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -0.0519   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3593    0.1993   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0619   -0.1114    0.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    0.1292    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950    0.6953   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4085    1.0161   -1.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0504    0.7756   -1.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5582    1.1390    2.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8005    1.3540    2.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6557   -0.2062    2.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6060   -1.0295    1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4903   -1.1587   -1.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4136   -0.4552   -2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635    0.4204   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285   -1.8911   -0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076   -0.4637   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6159   -0.8701    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075    0.2171   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5795   -0.5526    1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9902   -0.1157    1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1499    0.8959   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8993    1.4700   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4589    1.0040   -2.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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
  2 11  1  0
 11 12  1  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
 10  5  1  0
 20 15  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cinnamyl cinnamic acid	Generator
(2E)-3-Phenyl-2-propenyl (2E)-3-phenyl-2-propenoate	HMDB
2-Propenoic acid, 3-phenyl-, 3-phenyl-2-propenyl ester	HMDB
3-Phenyl allyl cinnamate	HMDB
3-Phenyl-2-propen-1-yl 3-phenyl propenoate	HMDB
3-Phenyl-2-propen-1-yl cinnamate	HMDB
Cinnamic acid, cinnamyl ester	HMDB
Cinnamyl alcohol, cinnamate	HMDB
Cinnamyl beta-phenyl acrylate	HMDB
Cinnamylester kyseliny skoricove	HMDB
Phenylallyl cinnamate	HMDB
Styracin	HMDB
(2E)-3-Phenylprop-2-en-1-yl (2Z)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₁₈H₁₆O₂

Average Molecular Weight

264.3184

Monoisotopic Molecular Weight

264.115029756

IUPAC Name

(2E)-3-phenylprop-2-en-1-yl (2Z)-3-phenylprop-2-enoate

Traditional Name

(2E)-3-phenylprop-2-en-1-yl (2Z)-3-phenylprop-2-enoate

CAS Registry Number

122-69-0

SMILES

O=C(OC\C=C\C1=CC=CC=C1)\C=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H16O2/c19-18(14-13-17-10-5-2-6-11-17)20-15-7-12-16-8-3-1-4-9-16/h1-14H,15H2/b12-7+,14-13-

InChI Key

NQBWNECTZUOWID-QSYVVUFSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Styrene
Fatty acid ester
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cell membrane (HMDB: HMDB0033832)

Cellular substructure

Membrane (HMDB: HMDB0033832)

Source

Exogenous

Food

Food (HMDB: HMDB0033832)

Endogenous

Plant

Plant (HMDB: HMDB0033832)

Not Available

Nutrient (HMDB: HMDB0033832)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0033832)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	44 °C	Not Available
Boiling Point	370.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	3.12 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.45	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00083 g/L	ALOGPS
logP	4.62	ALOGPS
logP	4.85	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.76 m³·mol⁻¹	ChemAxon
Polarizability	30.48 Å³	ChemAxon
Number of Rings	2	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]+	166.055	31661259
DarkChem	[M-H]-	163.05	31661259
DeepCCS	[M+H]+	161.078	30932474
DeepCCS	[M-H]-	158.72	30932474
DeepCCS	[M-2H]-	191.606	30932474
DeepCCS	[M+Na]+	167.171	30932474
AllCCS	[M+H]+	162.8	32859911
AllCCS	[M+H-H2O]+	159.0	32859911
AllCCS	[M+NH4]+	166.3	32859911
AllCCS	[M+Na]+	167.3	32859911
AllCCS	[M-H]-	167.5	32859911
AllCCS	[M+Na-2H]-	166.9	32859911
AllCCS	[M+HCOO]-	166.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cinnamyl cinnamate	O=C(OC\C=C\C1=CC=CC=C1)\C=C/C1=CC=CC=C1	3443.7	Standard polar	33892256
Cinnamyl cinnamate	O=C(OC\C=C\C1=CC=CC=C1)\C=C/C1=CC=CC=C1	2216.7	Standard non polar	33892256
Cinnamyl cinnamate	O=C(OC\C=C\C1=CC=CC=C1)\C=C/C1=CC=CC=C1	2408.7	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 - Cinnamyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gbc-2910000000-85b64ecb4c755def7bf8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnamyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnamyl cinnamate 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 - Cinnamyl cinnamate 10V, Positive-QTOF	splash10-014i-0590000000-b1cffc8382744a15cebd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 20V, Positive-QTOF	splash10-014i-0900000000-76ebfda733a5e9f84460	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 40V, Positive-QTOF	splash10-0uxu-6910000000-6754e4c1095f546754e5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 10V, Negative-QTOF	splash10-03di-0590000000-1f5818e4e7e8047b60bc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 20V, Negative-QTOF	splash10-0002-0910000000-e2b54b0166cc17c1dfcb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 40V, Negative-QTOF	splash10-0fvj-0900000000-07cb4c4ce72a1ae5e83b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 10V, Negative-QTOF	splash10-03di-0490000000-6f48263d0f6dab5b9eae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 20V, Negative-QTOF	splash10-0uxr-0910000000-c3cfd6e8c6c9299d0e7e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 40V, Negative-QTOF	splash10-0ufr-6900000000-19ff99e02c18d26a67bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 10V, Positive-QTOF	splash10-014i-0980000000-eb3fc338b096a28f68bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 20V, Positive-QTOF	splash10-014i-1910000000-cb70931978a75ff968b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl cinnamate 40V, Positive-QTOF	splash10-014l-5900000000-526a50aa85c77ae63656	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB012000

KNApSAcK ID

Not Available

Chemspider ID

1267365

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1550888

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1012411

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cinnamyl cinnamate (HMDB0033832)

MOL for HMDB0033832 (Cinnamyl cinnamate)

3D MOL for HMDB0033832 (Cinnamyl cinnamate)

3D SDF for HMDB0033832 (Cinnamyl cinnamate)

3D-SDF for HMDB0033832 (Cinnamyl cinnamate)

PDB for HMDB0033832 (Cinnamyl cinnamate)

3D PDB for HMDB0033832 (Cinnamyl cinnamate)

SMILES for HMDB0033832 (Cinnamyl cinnamate)

INCHI for HMDB0033832 (Cinnamyl cinnamate)

Structure for HMDB0033832 (Cinnamyl cinnamate)

3D Structure for HMDB0033832 (Cinnamyl cinnamate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra