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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:49:12 UTC

Update Date

2022-03-07 02:56:32 UTC

HMDB ID

HMDB0040286

Secondary Accession Numbers

HMDB40286

Metabolite Identification

Common Name

Benzyl cinnamate

Description

Benzyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Benzyl cinnamate is a sweet, apricot, and balsam tasting compound. Benzyl cinnamate is found, on average, in the highest concentration within cumins (Cuminum cyminum). This could make benzyl cinnamate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Benzyl cinnamate.

Structure

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

HMDB0040286
     RDKit          3D
Benzyl cinnamate
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.7951    0.7274   -0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -0.4283   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468   -1.6175   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -1.7294   -0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873   -0.6726   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3395    0.5090    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3380    1.4778    0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128    1.2660   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4882    0.0710   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5068   -0.8560   -0.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405   -0.5287    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    0.7053    0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299    0.3963    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1832    1.4050    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5097    1.0961    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9385   -0.2103    0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9817   -1.2112    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6622   -0.9071    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6100   -2.5998   -0.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563   -2.7786   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5690    0.7499    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2327    2.4032    0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1576    2.0384   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3463   -0.0917   -1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6361   -1.7888   -1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    1.3444    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    1.2146   -0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8220    2.4253    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2017    1.9428    0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9939   -0.4134    0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3090   -2.2465    0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9359   -1.6926    0.0510 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
 10  5  1  0
 18 13  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END


  Mrv0541 05061311442D          

 18 19  0  0  0  0            999 V2000
    1.4289    5.7750    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
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    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    4.9500    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
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 12 11  2  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 18 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040286

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2/b12-11-

> <INCHI_KEY>
NGHOLYJTSCBCGC-QXMHVHEDSA-N

> <FORMULA>
C16H14O2

> <MOLECULAR_WEIGHT>
238.2812

> <EXACT_MASS>
238.099379692

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.72708917437903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
benzyl (2Z)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
4.239786766666667

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.8193416254733625

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
72.4416

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzyl (2Z)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0040286
     RDKit          3D
Benzyl cinnamate
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.7951    0.7274   -0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -0.4283   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468   -1.6175   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -1.7294   -0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873   -0.6726   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3395    0.5090    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3380    1.4778    0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128    1.2660   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4882    0.0710   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5068   -0.8560   -0.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405   -0.5287    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    0.7053    0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299    0.3963    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1832    1.4050    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5097    1.0961    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9385   -0.2103    0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9817   -1.2112    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6622   -0.9071    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6100   -2.5998   -0.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563   -2.7786   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5690    0.7499    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2327    2.4032    0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1576    2.0384   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3463   -0.0917   -1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6361   -1.7888   -1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    1.3444    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    1.2146   -0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8220    2.4253    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2017    1.9428    0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9939   -0.4134    0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3090   -2.2465    0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9359   -1.6926    0.0510 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
 10  5  1  0
 18 13  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  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       2.667  10.780   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       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   9.240   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       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   6.930   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   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   14                                                       
CONECT    8    4   14                                                       
CONECT    9    5   15                                                       
CONECT   10    6   15                                                       
CONECT   11   12   14                                                       
CONECT   12   11   16                                                       
CONECT   13   15   18                                                       
CONECT   14    7    8   11                                                  
CONECT   15    9   10   13                                                  
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0040286
HETATM    1  O1  UNL     1      -0.795   0.727  -0.072  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.358  -0.428  -0.047  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.147  -1.618  -0.089  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.439  -1.729  -0.094  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.387  -0.673  -0.035  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.339   0.509   0.609  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.338   1.478   0.437  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.413   1.266  -0.393  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.488   0.071  -1.058  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.507  -0.856  -0.878  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.040  -0.529   0.033  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.793   0.705   0.078  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.230   0.396   0.168  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.183   1.405   0.284  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.510   1.096   0.368  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.939  -0.210   0.340  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.982  -1.211   0.224  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.662  -0.907   0.140  1.00  0.00           C  
HETATM   19  H1  UNL     1      -0.610  -2.600  -0.124  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.856  -2.779  -0.143  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.569   0.750   1.366  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.233   2.403   0.983  1.00  0.00           H  
HETATM   23  H5  UNL     1      -6.158   2.038  -0.497  1.00  0.00           H  
HETATM   24  H6  UNL     1      -6.346  -0.092  -1.716  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.636  -1.789  -1.444  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.425   1.344   0.900  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.594   1.215  -0.908  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.822   2.425   0.304  1.00  0.00           H  
HETATM   29  H11 UNL     1       6.202   1.943   0.457  1.00  0.00           H  
HETATM   30  H12 UNL     1       6.994  -0.413   0.408  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.309  -2.247   0.201  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.936  -1.693   0.051  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   19
CONECT    4    5   20
CONECT    5    6    6   10
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   25
CONECT   11   12
CONECT   12   13   26   27
CONECT   13   14   14   18
CONECT   14   15   28
CONECT   15   16   16   29
CONECT   16   17   30
CONECT   17   18   18   31
CONECT   18   32
END

HMDB0040286
     RDKit          3D
Benzyl cinnamate
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.7951    0.7274   -0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -0.4283   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468   -1.6175   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -1.7294   -0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873   -0.6726   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3395    0.5090    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3380    1.4778    0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128    1.2660   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4882    0.0710   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5068   -0.8560   -0.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405   -0.5287    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    0.7053    0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299    0.3963    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1832    1.4050    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5097    1.0961    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9385   -0.2103    0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9817   -1.2112    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6622   -0.9071    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6100   -2.5998   -0.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563   -2.7786   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5690    0.7499    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2327    2.4032    0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1576    2.0384   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3463   -0.0917   -1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6361   -1.7888   -1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    1.3444    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    1.2146   -0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8220    2.4253    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2017    1.9428    0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9939   -0.4134    0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3090   -2.2465    0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9359   -1.6926    0.0510 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
 10  5  1  0
 18 13  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Benzyl cinnamic acid	Generator
2-Propenoic acid, 3-phenyl-, phenylmethyl ester	HMDB
3-Phenyl-2-propenoic acid phenylmethyl ester	HMDB
Benzyl (2E)-3-phenyl-2-propenoate	HMDB
Benzyl 3-phenylpropenoate	HMDB
Benzyl alcohol cinnamic ester	HMDB
Benzyl alcohol, cinnamate	HMDB
Benzyl laquo gammaraquo -phenylacrylate	HMDB
Benzylcinnamate	HMDB
Benzylester kyseliny skoricove	HMDB
Cinnamein	HMDB
Cinnamic acid, benzyl ester	HMDB
FEMA 2142	HMDB
trans-Cinnamic acid benzyl ester	HMDB
Benzyl (2Z)-3-phenylprop-2-enoic acid	Generator
Benzyl cinnamate	MeSH

Chemical Formula

C₁₆H₁₄O₂

Average Molecular Weight

238.2812

Monoisotopic Molecular Weight

238.099379692

IUPAC Name

benzyl (2Z)-3-phenylprop-2-enoate

Traditional Name

benzyl (2Z)-3-phenylprop-2-enoate

CAS Registry Number

103-41-3

SMILES

O=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2/b12-11-

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040286)
Cell membrane (HMDB: HMDB0040286)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040286)

Source

Exogenous

Exogenous (HMDB: HMDB0040286)

Food

Food (HMDB: HMDB0040286)

Herb and spice

Spice

Cumin (FooDB: FOOD00067)

Endogenous

Plant

Plant (HMDB: HMDB0040286)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040286)
Flavor (HMDB: HMDB0040286)

Fragrance (HMDB: HMDB0040286)

Biological role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	37 - 39 °C	Not Available
Boiling Point	195.00 to 200.00 °C. @ 5.00 mm Hg	The Good Scents Company Information System
Water Solubility	9.27 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.060	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0034 g/L	ALOGPS
logP	4.03	ALOGPS
logP	4.24	ChemAxon
logS	-4.8	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	5	ChemAxon
Refractivity	72.44 m³·mol⁻¹	ChemAxon
Polarizability	26.73 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]+	158.928	31661259
DarkChem	[M-H]-	155.69	31661259
DeepCCS	[M+H]+	155.18	30932474
DeepCCS	[M-H]-	152.785	30932474
DeepCCS	[M-2H]-	185.765	30932474
DeepCCS	[M+Na]+	161.192	30932474
AllCCS	[M+H]+	154.8	32859911
AllCCS	[M+H-H2O]+	150.7	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	159.4	32859911
AllCCS	[M+Na-2H]-	158.9	32859911
AllCCS	[M+HCOO]-	158.5	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.	9.33 minutes	32390414
Predicted by Siyang on May 30, 2022	17.7486 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.99 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2940.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	593.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	230.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	342.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	796.8 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	782.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1704.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	641.7 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	1574.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	460.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	494.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	445.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	426.0 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	11.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzyl cinnamate	O=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C1	3024.2	Standard polar	33892256
Benzyl cinnamate	O=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C1	1982.7	Standard non polar	33892256
Benzyl cinnamate	O=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C1	2099.8	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 - Benzyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9600000000-b730105b1586b6466dfd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzyl 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 - Benzyl cinnamate 10V, Positive-QTOF	splash10-000i-1590000000-d59e744cc0df894ea1e3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 20V, Positive-QTOF	splash10-001i-2920000000-6c944a45122d144c5be2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 40V, Positive-QTOF	splash10-0006-9700000000-0cef35c32391ca819098	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 10V, Negative-QTOF	splash10-002r-0890000000-0c8dd31dd420da8aaa72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 20V, Negative-QTOF	splash10-004s-1910000000-475c63c855b416c3406c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 40V, Negative-QTOF	splash10-004i-3900000000-2e7d267ea7a7698e4165	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 10V, Negative-QTOF	splash10-000i-0090000000-4398f96ca62f3f4192ee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 20V, Negative-QTOF	splash10-054x-7930000000-651e889cc06e8e51210c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 40V, Negative-QTOF	splash10-0a6u-7920000000-7112ddc3c777a8c0212f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 10V, Positive-QTOF	splash10-000i-1390000000-66fcd7f42ef305268409	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 20V, Positive-QTOF	splash10-000x-5920000000-11bd2d1f6032302ebf18	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl cinnamate 40V, Positive-QTOF	splash10-0006-9600000000-78322ccdb4fc9f711f78	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

FDB020007

KNApSAcK ID

Not Available

Chemspider ID

21391699

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzyl cinnamate

METLIN ID

Not Available

PubChem Compound

15558051

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1014311

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 Benzyl cinnamate (HMDB0040286)

MOL for HMDB0040286 (Benzyl cinnamate)

3D MOL for HMDB0040286 (Benzyl cinnamate)

3D SDF for HMDB0040286 (Benzyl cinnamate)

3D-SDF for HMDB0040286 (Benzyl cinnamate)

PDB for HMDB0040286 (Benzyl cinnamate)

3D PDB for HMDB0040286 (Benzyl cinnamate)

SMILES for HMDB0040286 (Benzyl cinnamate)

INCHI for HMDB0040286 (Benzyl cinnamate)

Structure for HMDB0040286 (Benzyl cinnamate)

3D Structure for HMDB0040286 (Benzyl cinnamate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra