Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:41:53 UTC

Update Date

2022-03-07 02:54:57 UTC

HMDB ID

HMDB0036544

Secondary Accession Numbers

HMDB36544

Metabolite Identification

Common Name

1'-Acetoxyeugenol acetate

Description

1'-Acetoxyeugenol acetate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. 1'-Acetoxyeugenol acetate has been detected, but not quantified in, herbs and spices. This could make 1'-acetoxyeugenol acetate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 1'-Acetoxyeugenol acetate.

Structure

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

HMDB0036544
     RDKit          3D
1'-Acetoxyeugenol acetate
 35 35  0  0  0  0  0  0  0  0999 V2000
    3.3576    2.5534    0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7922    1.5435    1.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589    0.3463    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803   -0.8486    0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486   -1.7875    0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068   -3.0525    0.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7301   -1.5101   -0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920    0.4568    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    1.6633    0.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645    1.8110    0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    0.7720    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3963    0.9341    0.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0647    1.3357   -0.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5402    1.5114   -1.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3933    1.5554   -1.9975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4086   -0.4422   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653   -1.4797   -0.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350   -2.7542   -0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -0.5882   -0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4380    2.5173   -0.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202    3.3872    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    1.5643    2.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351    0.3626   -0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0258   -2.9299    2.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -3.2588    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557   -3.9086    0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417    2.5174    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5999    2.7640    0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7606    2.5001   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707    0.7516   -1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0033    1.4855   -0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1788   -3.1348    0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0369   -2.7152   -1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -3.4788   -1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3754   -1.5479   -0.3046 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  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19  8  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
 10 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
M  END


  Mrv0541 05061309112D          

 19 19  0  0  0  0            999 V2000
    0.0000    2.4750    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
   -5.0013   -0.4125    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
   -0.7145    2.0625    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
   -2.8579    0.8250    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  7  6  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  2  0  0  0  0
 16 10  2  0  0  0  0
 17  4  1  0  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 18 12  1  0  0  0  0
 19 10  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036544

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O5/c1-5-12(18-9(2)15)11-6-7-13(19-10(3)16)14(8-11)17-4/h5-8,12H,1H2,2-4H3

> <INCHI_KEY>
NKRBAUXTIWONOV-UHFFFAOYSA-N

> <FORMULA>
C14H16O5

> <MOLECULAR_WEIGHT>
264.2738

> <EXACT_MASS>
264.099773622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.809396631248735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[4-(acetyloxy)-3-methoxyphenyl]prop-2-en-1-yl acetate

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
1.887628061

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.899974491038187

> <JCHEM_POLAR_SURFACE_AREA>
61.83000000000001

> <JCHEM_REFRACTIVITY>
68.45390000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[4-(acetyloxy)-3-methoxyphenyl]prop-2-en-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036544
     RDKit          3D
1'-Acetoxyeugenol acetate
 35 35  0  0  0  0  0  0  0  0999 V2000
    3.3576    2.5534    0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7922    1.5435    1.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589    0.3463    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803   -0.8486    0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486   -1.7875    0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068   -3.0525    0.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7301   -1.5101   -0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920    0.4568    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    1.6633    0.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645    1.8110    0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    0.7720    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3963    0.9341    0.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0647    1.3357   -0.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5402    1.5114   -1.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3933    1.5554   -1.9975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4086   -0.4422   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653   -1.4797   -0.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350   -2.7542   -0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -0.5882   -0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4380    2.5173   -0.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202    3.3872    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    1.5643    2.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351    0.3626   -0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0258   -2.9299    2.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -3.2588    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557   -3.9086    0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417    2.5174    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5999    2.7640    0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7606    2.5001   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707    0.7516   -1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0033    1.4855   -0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1788   -3.1348    0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0369   -2.7152   -1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -3.4788   -1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3754   -1.5479   -0.3046 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  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19  8  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
 10 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   17                                                            
CONECT    5    1   12                                                       
CONECT    6    7   11                                                       
CONECT    7    6   13                                                       
CONECT    8   11   14                                                       
CONECT    9    2   15   18                                                  
CONECT   10    3   16   19                                                  
CONECT   11    6    8   12                                                  
CONECT   12    5   11   18                                                  
CONECT   13    7   14   19                                                  
CONECT   14    8   13   17                                                  
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17    4   14                                                       
CONECT   18    9   12                                                       
CONECT   19   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0036544
HETATM    1  C1  UNL     1       3.358   2.553   0.371  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.792   1.543   1.041  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.259   0.346   0.334  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.680  -0.849   0.987  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.449  -1.788   0.296  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.907  -3.053   0.954  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.730  -1.510  -0.900  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.792   0.457   0.280  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.203   1.663   0.584  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.164   1.811   0.547  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.003   0.772   0.208  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.396   0.934   0.173  1.00  0.00           O  
HETATM   13  C10 UNL     1      -4.065   1.336  -0.974  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.540   1.511  -1.025  1.00  0.00           C  
HETATM   15  O4  UNL     1      -3.393   1.555  -1.997  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.409  -0.442  -0.098  1.00  0.00           C  
HETATM   17  O5  UNL     1      -2.265  -1.480  -0.438  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.735  -2.754  -0.764  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.040  -0.588  -0.060  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.438   2.517  -0.707  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.720   3.387   0.959  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.704   1.564   2.124  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.635   0.363  -0.727  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.026  -2.930   2.034  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.928  -3.259   0.533  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.256  -3.909   0.667  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.842   2.517   0.860  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.600   2.764   0.788  1.00  0.00           H  
HETATM   29  H10 UNL     1      -5.761   2.500  -1.507  1.00  0.00           H  
HETATM   30  H11 UNL     1      -5.971   0.752  -1.710  1.00  0.00           H  
HETATM   31  H12 UNL     1      -6.003   1.485  -0.027  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.179  -3.135   0.118  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.037  -2.715  -1.611  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.532  -3.479  -1.008  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.375  -1.548  -0.305  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   22
CONECT    3    4    8   23
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   24   25   26
CONECT    8    9    9   19
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   16
CONECT   12   13
CONECT   13   14   15   15
CONECT   14   29   30   31
CONECT   16   17   19   19
CONECT   17   18
CONECT   18   32   33   34
CONECT   19   35
END

HMDB0036544
     RDKit          3D
1'-Acetoxyeugenol acetate
 35 35  0  0  0  0  0  0  0  0999 V2000
    3.3576    2.5534    0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7922    1.5435    1.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589    0.3463    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803   -0.8486    0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486   -1.7875    0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068   -3.0525    0.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7301   -1.5101   -0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920    0.4568    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    1.6633    0.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645    1.8110    0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    0.7720    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3963    0.9341    0.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0647    1.3357   -0.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5402    1.5114   -1.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3933    1.5554   -1.9975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4086   -0.4422   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653   -1.4797   -0.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350   -2.7542   -0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -0.5882   -0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4380    2.5173   -0.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202    3.3872    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    1.5643    2.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351    0.3626   -0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0258   -2.9299    2.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -3.2588    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557   -3.9086    0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417    2.5174    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5999    2.7640    0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7606    2.5001   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707    0.7516   -1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0033    1.4855   -0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1788   -3.1348    0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0369   -2.7152   -1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -3.4788   -1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3754   -1.5479   -0.3046 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  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19  8  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
 10 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1'-Acetoxyeugenol acetic acid	Generator
1'-Acetoxyeugenol	HMDB
1-[4-(Acetyloxy)-3-methoxyphenyl]prop-2-en-1-yl acetic acid	HMDB
1'-Acetoxyeugenol acetate	MeSH

Chemical Formula

C₁₄H₁₆O₅

Average Molecular Weight

264.2738

Monoisotopic Molecular Weight

264.099773622

IUPAC Name

1-[4-(acetyloxy)-3-methoxyphenyl]prop-2-en-1-yl acetate

Traditional Name

1-[4-(acetyloxy)-3-methoxyphenyl]prop-2-en-1-yl acetate

CAS Registry Number

52946-23-3

SMILES

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

InChI Identifier

InChI=1S/C14H16O5/c1-5-12(18-9(2)15)11-6-7-13(19-10(3)16)14(8-11)17-4/h5-8,12H,1H2,2-4H3

InChI Key

NKRBAUXTIWONOV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Benzyloxycarbonyl
Phenol ester
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Carboxylic acid ester
Ether
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036544)
Cytoplasm (HMDB: HMDB0036544)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036544)

Source

Exogenous

Exogenous (HMDB: HMDB0036544)

Food

Food (HMDB: HMDB0036544)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0036544)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036544)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.08 g/L	ALOGPS
logP	2.27	ALOGPS
logP	1.89	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.45 m³·mol⁻¹	ChemAxon
Polarizability	26.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.432	31661259
DarkChem	[M-H]-	163.389	31661259
DeepCCS	[M+H]+	161.759	30932474
DeepCCS	[M-H]-	159.401	30932474
DeepCCS	[M-2H]-	192.287	30932474
DeepCCS	[M+Na]+	167.852	30932474
AllCCS	[M+H]+	161.5	32859911
AllCCS	[M+H-H2O]+	157.9	32859911
AllCCS	[M+NH4]+	164.8	32859911
AllCCS	[M+Na]+	165.8	32859911
AllCCS	[M-H]-	162.6	32859911
AllCCS	[M+Na-2H]-	162.8	32859911
AllCCS	[M+HCOO]-	163.2	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.	6.33 minutes	32390414
Predicted by Siyang on May 30, 2022	13.547 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.94 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	23.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2181.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	354.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	196.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	88.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	492.0 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	577.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	87.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1165.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	441.5 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	1521.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	385.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	364.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	279.8 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	11.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1'-Acetoxyeugenol acetate	COC1=C(OC(C)=O)C=CC(=C1)C(OC(C)=O)C=C	2792.6	Standard polar	33892256
1'-Acetoxyeugenol acetate	COC1=C(OC(C)=O)C=CC(=C1)C(OC(C)=O)C=C	1903.1	Standard non polar	33892256
1'-Acetoxyeugenol acetate	COC1=C(OC(C)=O)C=CC(=C1)C(OC(C)=O)C=C	1835.2	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 - 1'-Acetoxyeugenol acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-3940000000-26ad1f62904aa74b8f76	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1'-Acetoxyeugenol acetate 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 - 1'-Acetoxyeugenol acetate 10V, Positive-QTOF	splash10-06di-0190000000-70a9a8411e7db5b583a6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 20V, Positive-QTOF	splash10-0ab9-0490000000-5b4f108e63fbc784a0dc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 40V, Positive-QTOF	splash10-03di-2920000000-25b0b7c5987ce0fe87fd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 10V, Negative-QTOF	splash10-03k9-1090000000-c09424250156ecf96d2d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 20V, Negative-QTOF	splash10-0ab9-3390000000-9e41add5cbb007ffb962	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 40V, Negative-QTOF	splash10-0a4i-9840000000-6d29eee6e7a4feb7eec9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 10V, Negative-QTOF	splash10-0229-0290000000-0d2628c801299c4e8035	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 20V, Negative-QTOF	splash10-0a4i-8690000000-2e99db05d391d4dac0aa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 40V, Negative-QTOF	splash10-0a4i-9140000000-44c6e8f4f0337f89acad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 10V, Positive-QTOF	splash10-01b9-0390000000-add671174c4132d587d9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 20V, Positive-QTOF	splash10-0a4u-9530000000-1b03c228aa93ced38d71	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxyeugenol acetate 40V, Positive-QTOF	splash10-06vi-1920000000-fe6dc46fd9543c9b198f	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB015447

KNApSAcK ID

C00002712

Chemspider ID

3682061

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4484222

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 1'-Acetoxyeugenol acetate (HMDB0036544)

MOL for HMDB0036544 (1'-Acetoxyeugenol acetate)

3D MOL for HMDB0036544 (1'-Acetoxyeugenol acetate)

3D SDF for HMDB0036544 (1'-Acetoxyeugenol acetate)

3D-SDF for HMDB0036544 (1'-Acetoxyeugenol acetate)

PDB for HMDB0036544 (1'-Acetoxyeugenol acetate)

3D PDB for HMDB0036544 (1'-Acetoxyeugenol acetate)

SMILES for HMDB0036544 (1'-Acetoxyeugenol acetate)

INCHI for HMDB0036544 (1'-Acetoxyeugenol acetate)

Structure for HMDB0036544 (1'-Acetoxyeugenol acetate)

3D Structure for HMDB0036544 (1'-Acetoxyeugenol acetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra