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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:57:44 UTC

Update Date

2023-02-21 17:25:57 UTC

HMDB ID

HMDB0037702

Secondary Accession Numbers

HMDB37702

Metabolite Identification

Common Name

Butyl cinnamate

Description

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

Structure

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

HMDB0037702
     RDKit          3D
Butyl cinnamate
 31 31  0  0  0  0  0  0  0  0999 V2000
    4.8795   -0.5550    1.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5604    0.0221    1.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5384   -0.0279    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2482    0.5814    0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2205    0.5880   -0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    1.2002   -1.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    1.8362   -1.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7511    1.2585   -2.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9411    0.7616   -2.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5485    0.0626   -1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496   -0.9541   -1.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2016   -1.6596   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1255   -1.4198    0.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2688   -0.4439    1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063    0.2715    0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7339   -0.0913    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0855   -0.5000    0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9039   -1.6414    1.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6521    1.0630    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243   -0.5586    2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156    0.4580   -0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994   -1.0807    0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613    1.6144    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8927   -0.0560    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4304    1.8106   -3.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329    0.9287   -3.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5788   -1.2158   -2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8796   -2.4300   -1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7290   -1.9914    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895   -0.2354    2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9268    1.0738    0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  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 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
M  END


  Mrv0541 05061309572D          

 15 15  0  0  0  0            999 V2000
   -0.7145    5.3625    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    5.3625    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
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    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
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    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
    4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  9  2  0  0  0  0
 11  3  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 13  2  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037702

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O2/c1-2-3-11-15-13(14)10-9-12-7-5-4-6-8-12/h4-10H,2-3,11H2,1H3/b10-9-

> <INCHI_KEY>
OHHIVLJVBNCSHV-KTKRTIGZSA-N

> <FORMULA>
C13H16O2

> <MOLECULAR_WEIGHT>
204.2649

> <EXACT_MASS>
204.115029756

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.901019489093464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
3.8392126639999997

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.808951654514645

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
61.702600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037702
     RDKit          3D
Butyl cinnamate
 31 31  0  0  0  0  0  0  0  0999 V2000
    4.8795   -0.5550    1.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5604    0.0221    1.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5384   -0.0279    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2482    0.5814    0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2205    0.5880   -0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    1.2002   -1.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    1.8362   -1.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7511    1.2585   -2.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9411    0.7616   -2.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5485    0.0626   -1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496   -0.9541   -1.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2016   -1.6596   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1255   -1.4198    0.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2688   -0.4439    1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063    0.2715    0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7339   -0.0913    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0855   -0.5000    0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9039   -1.6414    1.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6521    1.0630    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243   -0.5586    2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156    0.4580   -0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994   -1.0807    0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613    1.6144    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8927   -0.0560    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4304    1.8106   -3.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329    0.9287   -3.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5788   -1.2158   -2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8796   -2.4300   -1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7290   -1.9914    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895   -0.2354    2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9268    1.0738    0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  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 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  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      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2   11                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   12                                                       
CONECT    8    6   12                                                       
CONECT    9   10   12                                                       
CONECT   10    9   13                                                       
CONECT   11    3   15                                                       
CONECT   12    7    8    9                                                  
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0037702
HETATM    1  C1  UNL     1       4.879  -0.555   1.170  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.560   0.022   1.557  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.538  -0.028   0.443  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.248   0.581   0.949  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.220   0.588  -0.008  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.221   1.200  -1.222  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.322   1.836  -1.471  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.751   1.258  -2.257  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.941   0.762  -2.240  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.548   0.063  -1.171  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.450  -0.954  -1.562  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.202  -1.660  -0.665  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.125  -1.420   0.683  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.269  -0.444   1.107  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.506   0.271   0.177  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.734  -0.091   1.707  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.085  -0.500   0.073  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.904  -1.641   1.464  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.652   1.063   1.927  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.124  -0.559   2.409  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.916   0.458  -0.478  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.299  -1.081   0.174  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.461   1.614   1.340  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.893  -0.056   1.794  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.430   1.811  -3.208  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.533   0.929  -3.204  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.579  -1.216  -2.609  1.00  0.00           H  
HETATM   28  H13 UNL     1      -4.880  -2.430  -1.000  1.00  0.00           H  
HETATM   29  H14 UNL     1      -4.729  -1.991   1.376  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.189  -0.235   2.154  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.927   1.074   0.591  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9    9   25
CONECT    9   10   26
CONECT   10   11   11   15
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   31
END

HMDB0037702
     RDKit          3D
Butyl cinnamate
 31 31  0  0  0  0  0  0  0  0999 V2000
    4.8795   -0.5550    1.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5604    0.0221    1.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5384   -0.0279    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2482    0.5814    0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2205    0.5880   -0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    1.2002   -1.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    1.8362   -1.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7511    1.2585   -2.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9411    0.7616   -2.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5485    0.0626   -1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496   -0.9541   -1.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2016   -1.6596   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1255   -1.4198    0.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2688   -0.4439    1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063    0.2715    0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7339   -0.0913    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0855   -0.5000    0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9039   -1.6414    1.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6521    1.0630    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243   -0.5586    2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156    0.4580   -0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994   -1.0807    0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613    1.6144    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8927   -0.0560    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4304    1.8106   -3.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329    0.9287   -3.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5788   -1.2158   -2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8796   -2.4300   -1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7290   -1.9914    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895   -0.2354    2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9268    1.0738    0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  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 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Butyl cinnamic acid	Generator
2-Propenoic acid, 3-phenyl-, butyl ester	HMDB
3-Phenyl-acrylic acid, butyl ester	HMDB
Butyl 3-phenyl-2-propenoate	HMDB
Butyl 3-phenylpropenoate	HMDB
Butyl phenylacrylate	HMDB
Butyl-beta-phenylacrylate	HMDB
Cinnamate de N-butyle	HMDB
Cinnamic acid butyl ester	HMDB
Cinnamic acid N-butyl ester	HMDB
Cinnamic acid, butyl ester	HMDB
Eliminoxy	HMDB
FEMA 2192	HMDB
N-Butyl cinnamate	HMDB
N-Butyl phenylacrylate	HMDB
Butyl (2Z)-3-phenylprop-2-enoic acid	Generator
Tert-butyl cinnamate	MeSH
Butyl cinnamate	MeSH

Chemical Formula

C₁₃H₁₆O₂

Average Molecular Weight

204.2649

Monoisotopic Molecular Weight

204.115029756

IUPAC Name

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

Traditional Name

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

CAS Registry Number

538-65-8

SMILES

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

InChI Identifier

InChI=1S/C13H16O2/c1-2-3-11-15-13(14)10-9-12-7-5-4-6-8-12/h4-10H,2-3,11H2,1H3/b10-9-

InChI Key

OHHIVLJVBNCSHV-KTKRTIGZSA-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

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037702)
Cell membrane (HMDB: HMDB0037702)

Source

Exogenous

Exogenous (HMDB: HMDB0037702)

Food

Food (HMDB: HMDB0037702)

Endogenous

Plant

Plant (HMDB: HMDB0037702)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037702)

Biological role

Nutrient (HMDB: HMDB0037702)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	3.93	ALOGPS
logP	3.84	ChemAxon
logS	-4.1	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	61.7 m³·mol⁻¹	ChemAxon
Polarizability	23.9 Å³	ChemAxon
Number of Rings	1	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]+	147.691	31661259
DarkChem	[M-H]-	148.753	31661259
DeepCCS	[M+H]+	150.358	30932474
DeepCCS	[M-H]-	147.928	30932474
DeepCCS	[M-2H]-	182.936	30932474
DeepCCS	[M+Na]+	158.733	30932474
AllCCS	[M+H]+	146.9	32859911
AllCCS	[M+H-H2O]+	143.0	32859911
AllCCS	[M+NH4]+	150.6	32859911
AllCCS	[M+Na]+	151.6	32859911
AllCCS	[M-H]-	151.6	32859911
AllCCS	[M+Na-2H]-	152.3	32859911
AllCCS	[M+HCOO]-	153.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.19 minutes	32390414
Predicted by Siyang on May 30, 2022	17.1638 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.34 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2716.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	573.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	220.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	350.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	401.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	767.9 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	764.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1594.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	570.7 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	1494.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	468.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	463.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	436.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	468.5 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butyl cinnamate	CCCCOC(=O)\C=C/C1=CC=CC=C1	2284.8	Standard polar	33892256
Butyl cinnamate	CCCCOC(=O)\C=C/C1=CC=CC=C1	1606.5	Standard non polar	33892256
Butyl cinnamate	CCCCOC(=O)\C=C/C1=CC=CC=C1	1703.3	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 - Butyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-6900000000-0d21e381e2542b15607f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl 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 - Butyl cinnamate 10V, Positive-QTOF	splash10-0a4i-4490000000-fffbfda43959205b8dc9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 20V, Positive-QTOF	splash10-0a4i-9510000000-496dcf83df8656dbbc96	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 40V, Positive-QTOF	splash10-0pbc-9200000000-6c3d8e4710fc3c621e3e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 10V, Negative-QTOF	splash10-0ufr-2790000000-73bd16f22005bd31aaa7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 20V, Negative-QTOF	splash10-0f92-1910000000-be03d86327a98bae2bc3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 40V, Negative-QTOF	splash10-0fb9-3900000000-cec7b52250a5a0086980	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 10V, Negative-QTOF	splash10-0udi-0940000000-77395fc8665b8abc7652	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 20V, Negative-QTOF	splash10-0f6x-9510000000-af8cbe09e10ba806a267	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 40V, Negative-QTOF	splash10-0fb9-9600000000-df961893a546f3c3edfb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 10V, Positive-QTOF	splash10-053r-0930000000-51411e58beeb0eb816cb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 20V, Positive-QTOF	splash10-0ue9-3900000000-422969c7ab529a7224b3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl cinnamate 40V, Positive-QTOF	splash10-0udi-4900000000-596427e1756466414ab7	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

FDB016830

KNApSAcK ID

C00035549

Chemspider ID

21427812

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25021438

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Butyl cinnamate (HMDB0037702)

MOL for HMDB0037702 (Butyl cinnamate)

3D MOL for HMDB0037702 (Butyl cinnamate)

3D SDF for HMDB0037702 (Butyl cinnamate)

3D-SDF for HMDB0037702 (Butyl cinnamate)

PDB for HMDB0037702 (Butyl cinnamate)

3D PDB for HMDB0037702 (Butyl cinnamate)

SMILES for HMDB0037702 (Butyl cinnamate)

INCHI for HMDB0037702 (Butyl cinnamate)

Structure for HMDB0037702 (Butyl cinnamate)

3D Structure for HMDB0037702 (Butyl cinnamate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra