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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:30 UTC

Update Date

2022-03-07 02:53:13 UTC

HMDB ID

HMDB0032056

Secondary Accession Numbers

HMDB32056

Metabolite Identification

Common Name

Eugenyl benzoate

Description

Eugenyl benzoate belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). Eugenyl benzoate is a mild, balsam, and clove tasting compound. Eugenyl benzoate has been detected, but not quantified in, herbs and spices. This could make eugenyl benzoate a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Eugenyl benzoate.

Structure

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

HMDB0032056
     RDKit          3D
Eugenyl benzoate
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.5786    1.9195    0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8740    0.8073    0.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4237    0.1825   -0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483    0.0674   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    1.1234   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8877    1.0302   -1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761   -0.0602   -0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2012   -0.0662   -0.8575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    0.4433    0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4135    0.9038    1.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533    0.4516    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0249   -0.0635   -1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4084   -0.0565   -1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2336    0.4454   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6503    0.9621    0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    0.9520    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8675   -1.1011   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851   -2.2184    0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8461   -3.3148    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2383   -1.0094   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8679    2.4405   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8782    2.3262    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6155    0.3337    1.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8744   -0.8263   -0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851    0.7943   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000    2.0092   -1.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3359    1.8657   -1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429   -0.4725   -1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8684   -0.4571   -2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3121    0.4531   -0.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2720    1.3631    1.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520    1.3662    1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4192   -3.9200    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726   -2.8785    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1474   -3.9629    1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079   -1.8332    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  7 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20  4  1  0
 16 11  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
M  END


  Mrv0541 05061306192D          

 20 21  0  0  0  0            999 V2000
   -2.1434   -2.8875    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
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    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   -0.4125    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 11 10  2  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  2  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  2  0  0  0  0
 17 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19  2  1  0  0  0  0
 19 16  1  0  0  0  0
 20 15  1  0  0  0  0
 20 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032056

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC(=O)C2=CC=CC=C2)C=CC(CC=C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O3/c1-3-7-13-10-11-15(16(12-13)19-2)20-17(18)14-8-5-4-6-9-14/h3-6,8-12H,1,7H2,2H3

> <INCHI_KEY>
ZOGNBLKDKPCKGB-UHFFFAOYSA-N

> <FORMULA>
C17H16O3

> <MOLECULAR_WEIGHT>
268.3071

> <EXACT_MASS>
268.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.264696693670494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-4-(prop-2-en-1-yl)phenyl benzoate

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
4.575580696

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.901381638317587

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
78.6114

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-4-(prop-2-en-1-yl)phenyl benzoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032056
     RDKit          3D
Eugenyl benzoate
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.5786    1.9195    0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8740    0.8073    0.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4237    0.1825   -0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483    0.0674   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    1.1234   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8877    1.0302   -1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761   -0.0602   -0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2012   -0.0662   -0.8575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    0.4433    0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4135    0.9038    1.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533    0.4516    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0249   -0.0635   -1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4084   -0.0565   -1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2336    0.4454   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6503    0.9621    0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    0.9520    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8675   -1.1011   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851   -2.2184    0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8461   -3.3148    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2383   -1.0094   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8679    2.4405   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8782    2.3262    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6155    0.3337    1.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8744   -0.8263   -0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851    0.7943   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000    2.0092   -1.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3359    1.8657   -1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429   -0.4725   -1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8684   -0.4571   -2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3121    0.4531   -0.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2720    1.3631    1.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520    1.3662    1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4192   -3.9200    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726   -2.8785    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1474   -3.9629    1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079   -1.8332    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  7 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20  4  1  0
 16 11  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 19 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      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   19                                                            
CONECT    3    1    7                                                       
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    4    9                                                       
CONECT    7    3   13                                                       
CONECT    8    5   14                                                       
CONECT    9    6   14                                                       
CONECT   10   11   13                                                       
CONECT   11   10   15                                                       
CONECT   12   13   16                                                       
CONECT   13    7   10   12                                                  
CONECT   14    8    9   17                                                  
CONECT   15   11   16   20                                                  
CONECT   16   12   15   19                                                  
CONECT   17   14   18   20                                                  
CONECT   18   17                                                            
CONECT   19    2   16                                                       
CONECT   20   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0032056
HETATM    1  C1  UNL     1      -5.579   1.920   0.868  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.874   0.807   0.853  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.424   0.183  -0.398  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.948   0.067  -0.495  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.262   1.123  -1.070  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.888   1.030  -1.167  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.176  -0.060  -0.719  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.201  -0.066  -0.857  1.00  0.00           O  
HETATM    9  C8  UNL     1       2.002   0.443   0.146  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.414   0.904   1.173  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.453   0.452   0.030  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.025  -0.064  -1.111  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.408  -0.056  -1.222  1.00  0.00           C  
HETATM   14  C12 UNL     1       6.234   0.445  -0.237  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.650   0.962   0.908  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.257   0.952   1.014  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.867  -1.101  -0.150  1.00  0.00           C  
HETATM   18  O3  UNL     1      -0.185  -2.218   0.314  1.00  0.00           O  
HETATM   19  C16 UNL     1      -0.846  -3.315   0.906  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.238  -1.009  -0.053  1.00  0.00           C  
HETATM   21  H1  UNL     1      -5.868   2.441  -0.050  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.878   2.326   1.829  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.616   0.334   1.789  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.874  -0.826  -0.525  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.785   0.794  -1.250  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.800   2.009  -1.438  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.336   1.866  -1.623  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.443  -0.473  -1.922  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.868  -0.457  -2.111  1.00  0.00           H  
HETATM   30  H10 UNL     1       7.312   0.453  -0.319  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.272   1.363   1.699  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.852   1.366   1.927  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.419  -3.920   0.187  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.573  -2.878   1.640  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.147  -3.963   1.452  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.808  -1.833   0.399  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3   23
CONECT    3    4   24   25
CONECT    4    5    5   20
CONECT    5    6   26
CONECT    6    7    7   27
CONECT    7    8   17
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   16   32
CONECT   17   18   20   20
CONECT   18   19
CONECT   19   33   34   35
CONECT   20   36
END

HMDB0032056
     RDKit          3D
Eugenyl benzoate
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.5786    1.9195    0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8740    0.8073    0.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4237    0.1825   -0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483    0.0674   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    1.1234   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8877    1.0302   -1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761   -0.0602   -0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2012   -0.0662   -0.8575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    0.4433    0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4135    0.9038    1.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533    0.4516    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0249   -0.0635   -1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4084   -0.0565   -1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2336    0.4454   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6503    0.9621    0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    0.9520    1.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8675   -1.1011   -0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851   -2.2184    0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8461   -3.3148    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2383   -1.0094   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8679    2.4405   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8782    2.3262    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6155    0.3337    1.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8744   -0.8263   -0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851    0.7943   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000    2.0092   -1.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3359    1.8657   -1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429   -0.4725   -1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8684   -0.4571   -2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3121    0.4531   -0.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2720    1.3631    1.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520    1.3662    1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4192   -3.9200    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726   -2.8785    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1474   -3.9629    1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079   -1.8332    0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  7 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20  4  1  0
 16 11  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Eugenyl benzoic acid	Generator
2-Methoxy-4-(2-propenyl)phenyl benzoate	HMDB
4-Allyl-2-methoxyphenyl benzoate	HMDB
Benzoyl eugenol	HMDB
Eugenol benzoate	HMDB
FEMA 2471	HMDB
P-Eugenol, benzoate	HMDB
Phenol, 2-methoxy-4-(2-propen-1-yl)-, 1-benzoate	HMDB
Phenol, 2-methoxy-4-(2-propenyl)-, benzoate	HMDB
Phenol, 4-allyl-2-methoxy-, benzoate	HMDB
Phenol, 4-allyl-2-methoxy-, benzoate (8ci)	HMDB
2-Methoxy-4-(prop-2-en-1-yl)phenyl benzoic acid	Generator

Chemical Formula

C₁₇H₁₆O₃

Average Molecular Weight

268.3071

Monoisotopic Molecular Weight

268.109944378

IUPAC Name

2-methoxy-4-(prop-2-en-1-yl)phenyl benzoate

Traditional Name

2-methoxy-4-(prop-2-en-1-yl)phenyl benzoate

CAS Registry Number

531-26-0

SMILES

COC1=C(OC(=O)C2=CC=CC=C2)C=CC(CC=C)=C1

InChI Identifier

InChI=1S/C17H16O3/c1-3-7-13-10-11-15(16(12-13)19-2)20-17(18)14-8-5-4-6-9-14/h3-6,8-12H,1,7H2,2H3

InChI Key

ZOGNBLKDKPCKGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
Benzoate ester
Phenol ester
Benzoic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0032056)
Cell membrane (HMDB: HMDB0032056)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032056)

Source

Endogenous

Endogenous (HMDB: HMDB0032056)

Plant

Plant (HMDB: HMDB0032056)

Exogenous

Food

Food (HMDB: HMDB0032056)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0032056)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032056)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	69 - 70 °C	Not Available
Boiling Point	360.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2.58 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.447 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0041 g/L	ALOGPS
logP	4.23	ALOGPS
logP	4.58	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.61 m³·mol⁻¹	ChemAxon
Polarizability	29.26 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]+	164.185	31661259
DarkChem	[M-H]-	162.934	31661259
DeepCCS	[M+H]+	166.232	30932474
DeepCCS	[M-H]-	163.874	30932474
DeepCCS	[M-2H]-	196.761	30932474
DeepCCS	[M+Na]+	172.326	30932474
AllCCS	[M+H]+	162.9	32859911
AllCCS	[M+H-H2O]+	159.1	32859911
AllCCS	[M+NH4]+	166.3	32859911
AllCCS	[M+Na]+	167.3	32859911
AllCCS	[M-H]-	166.3	32859911
AllCCS	[M+Na-2H]-	165.6	32859911
AllCCS	[M+HCOO]-	165.1	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.	8.82 minutes	32390414
Predicted by Siyang on May 30, 2022	17.978 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2630.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	565.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	226.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	323.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	762.3 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	782.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1644.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	592.3 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	1617.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	504.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	504.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	419.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	439.3 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	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eugenyl benzoate	COC1=C(OC(=O)C2=CC=CC=C2)C=CC(CC=C)=C1	3066.9	Standard polar	33892256
Eugenyl benzoate	COC1=C(OC(=O)C2=CC=CC=C2)C=CC(CC=C)=C1	2119.5	Standard non polar	33892256
Eugenyl benzoate	COC1=C(OC(=O)C2=CC=CC=C2)C=CC(CC=C)=C1	2121.0	Semi standard non polar	33892256

Spectra

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

FDB008763

KNApSAcK ID

C00053971

Chemspider ID

56151

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62362

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1023511

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.. .

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

Eugenyl benzoate → Eugenol	details

Showing metabocard for Eugenyl benzoate (HMDB0032056)

MOL for HMDB0032056 (Eugenyl benzoate)

3D MOL for HMDB0032056 (Eugenyl benzoate)

3D SDF for HMDB0032056 (Eugenyl benzoate)

3D-SDF for HMDB0032056 (Eugenyl benzoate)

PDB for HMDB0032056 (Eugenyl benzoate)

3D PDB for HMDB0032056 (Eugenyl benzoate)

SMILES for HMDB0032056 (Eugenyl benzoate)

INCHI for HMDB0032056 (Eugenyl benzoate)

Structure for HMDB0032056 (Eugenyl benzoate)

3D Structure for HMDB0032056 (Eugenyl benzoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Enzymes

Reactions