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

2012-09-12 02:38:19 UTC

Update Date

2022-03-07 02:56:50 UTC

HMDB ID

HMDB0041006

Secondary Accession Numbers

HMDB41006

Metabolite Identification

Common Name

1'-Acetoxychavicol

Description

1'-Acetoxychavicol 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'-Acetoxychavicol has been detected, but not quantified in, herbs and spices and root vegetables. This could make 1'-acetoxychavicol a potential biomarker for the consumption of these foods. 1'-Acetoxychavicol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 1'-Acetoxychavicol.

Structure

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

HMDB0041006
     RDKit          3D
1'-Acetoxychavicol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.9849   -2.8687   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -2.0182   -0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8424   -0.9381    0.1015 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6828    0.1664   -0.1456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6273    0.6523    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264    1.8323    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7827    0.0900    1.8199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4531   -0.4227    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -0.8104    1.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -0.3399    1.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462    0.5814    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215    1.0793    0.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913    0.4993   -0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8814    1.0442   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328   -0.5421   -0.8485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3019    1.0097   -0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183    0.5112   -0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7458   -2.7668   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0957   -3.6628   -1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277   -2.1401   -1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227   -1.3091    1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792    2.4288    1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773    2.4808   -0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3631    1.5427   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0721   -1.5366    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -0.6735    2.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3715    0.8856   -1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8371    2.1410    0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875    0.4985    0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    1.7374   -1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6295    0.8483   -1.4991 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  2  0
 17  8  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  1
  6 22  1  0
  6 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
M  END

  Mrv0541 02241220442D          

 17 17  0  0  0  0            999 V2000
    0.6770   -0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3850    0.3161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6770   -0.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378    0.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3850    1.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378   -1.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7560   -0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667    1.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8111    0.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7560   -0.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0446    1.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667    2.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709   -1.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857   -0.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8937   -1.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857   -0.0997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  1  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  2  0  0  0  0
  9 12  1  0  0  0  0
  9 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  8 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041006

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)O[C@@H](C=C)C1=CC=C(OC(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O4/c1-4-13(17-10(3)15)11-5-7-12(8-6-11)16-9(2)14/h4-8,13H,1H2,2-3H3/t13-/m0/s1

> <INCHI_KEY>
JAMQIUWGGBSIKZ-ZDUSSCGKSA-N

> <FORMULA>
C13H14O4

> <MOLECULAR_WEIGHT>
234.2479

> <EXACT_MASS>
234.089208936

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.057704185865123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.045299326666667

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.7784067139381206

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
61.990700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1'-acetoxychavicol acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041006
     RDKit          3D
1'-Acetoxychavicol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.9849   -2.8687   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -2.0182   -0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8424   -0.9381    0.1015 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6828    0.1664   -0.1456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6273    0.6523    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264    1.8323    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7827    0.0900    1.8199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4531   -0.4227    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -0.8104    1.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -0.3399    1.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462    0.5814    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215    1.0793    0.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913    0.4993   -0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8814    1.0442   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328   -0.5421   -0.8485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3019    1.0097   -0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183    0.5112   -0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7458   -2.7668   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0957   -3.6628   -1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277   -2.1401   -1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227   -1.3091    1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792    2.4288    1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773    2.4808   -0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3631    1.5427   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0721   -1.5366    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -0.6735    2.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3715    0.8856   -1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8371    2.1410    0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875    0.4985    0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    1.7374   -1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6295    0.8483   -1.4991 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  2  0
 17  8  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  1
  6 22  1  0
  6 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.264  -0.186   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.585   0.590   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.264  -1.726   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.071   0.590   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.585   2.136   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.920  -0.180   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.071  -2.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.411  -0.186   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.245   2.899   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.247   0.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.411  -1.726   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.083   2.136   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.245   4.446   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.746  -2.496   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.080  -1.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.402  -2.496   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.080  -0.186   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12   13                                                  
CONECT   10    6                                                            
CONECT   11    7   14    8                                                  
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0041006
HETATM    1  C1  UNL     1      -2.985  -2.869  -0.848  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.971  -2.018  -0.875  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.842  -0.938   0.102  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.683   0.166  -0.146  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.627   0.652   0.713  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.426   1.832   0.283  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.783   0.090   1.820  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.453  -0.423   0.219  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.418  -0.810   1.199  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.711  -0.340   1.321  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.146   0.581   0.389  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.422   1.079   0.466  1.00  0.00           O  
HETATM   13  C10 UNL     1       4.491   0.499  -0.161  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.881   1.044  -0.076  1.00  0.00           C  
HETATM   15  O4  UNL     1       4.333  -0.542  -0.849  1.00  0.00           O  
HETATM   16  C12 UNL     1       1.302   1.010  -0.628  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.018   0.511  -0.708  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.746  -2.767  -0.081  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.096  -3.663  -1.552  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.228  -2.140  -1.647  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.123  -1.309   1.131  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.679   2.429   1.187  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.777   2.481  -0.342  1.00  0.00           H  
HETATM   24  H7  UNL     1      -5.363   1.543  -0.224  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.072  -1.537   1.932  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.384  -0.674   2.121  1.00  0.00           H  
HETATM   27  H10 UNL     1       6.372   0.886  -1.052  1.00  0.00           H  
HETATM   28  H11 UNL     1       5.837   2.141   0.090  1.00  0.00           H  
HETATM   29  H12 UNL     1       6.387   0.498   0.741  1.00  0.00           H  
HETATM   30  H13 UNL     1       1.638   1.737  -1.368  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.630   0.848  -1.499  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   20
CONECT    3    4    8   21
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   22   23   24
CONECT    8    9    9   17
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12   16
CONECT   12   13
CONECT   13   14   15   15
CONECT   14   27   28   29
CONECT   16   17   17   30
CONECT   17   31
END

HMDB0041006
     RDKit          3D
1'-Acetoxychavicol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.9849   -2.8687   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -2.0182   -0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8424   -0.9381    0.1015 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6828    0.1664   -0.1456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6273    0.6523    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264    1.8323    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7827    0.0900    1.8199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4531   -0.4227    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -0.8104    1.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -0.3399    1.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462    0.5814    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215    1.0793    0.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913    0.4993   -0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8814    1.0442   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328   -0.5421   -0.8485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3019    1.0097   -0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183    0.5112   -0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7458   -2.7668   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0957   -3.6628   -1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277   -2.1401   -1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227   -1.3091    1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792    2.4288    1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773    2.4808   -0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3631    1.5427   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0721   -1.5366    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -0.6735    2.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3715    0.8856   -1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8371    2.1410    0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875    0.4985    0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    1.7374   -1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6295    0.8483   -1.4991 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  2  0
 17  8  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  1
  6 22  1  0
  6 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(AlphaS)-4-(acetyloxy)-alpha-ethenylbenzenemethanol	ChEBI
(AlphaS)-4-(acetyloxy)-a-ethenylbenzenemethanol	Generator
(AlphaS)-4-(acetyloxy)-α-ethenylbenzenemethanol	Generator
1'-Acetoxychavicol acetic acid	Generator

Chemical Formula

C₁₃H₁₄O₄

Average Molecular Weight

234.2479

Monoisotopic Molecular Weight

234.089208936

IUPAC Name

(1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate

Traditional Name

1'-acetoxychavicol acetate

CAS Registry Number

151986-17-3

SMILES

CC(=O)O[C@@H](C=C)C1=CC=C(OC(C)=O)C=C1

InChI Identifier

InChI=1S/C13H14O4/c1-4-13(17-10(3)15)11-5-7-12(8-6-11)16-9(2)14/h4-8,13H,1H2,2-3H3/t13-/m0/s1

InChI Key

JAMQIUWGGBSIKZ-ZDUSSCGKSA-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

Phenol ester
Benzyloxycarbonyl
Phenoxy compound
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylpropanoid (CHEBI:469 )
acetate ester (CHEBI:469 )
Monolignols (C10426 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041006)
Cell membrane (HMDB: HMDB0041006)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041006)

Source

Exogenous

Exogenous (HMDB: HMDB0041006)

Food

Food (HMDB: HMDB0041006)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Endogenous

Plant

Plant (HMDB: HMDB0041006)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041006)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	325.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	233.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.900 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.58	ALOGPS
logP	2.05	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.99 m³·mol⁻¹	ChemAxon
Polarizability	24.06 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]+	158.357	31661259
DarkChem	[M-H]-	152.895	31661259
DeepCCS	[M+H]+	156.872	30932474
DeepCCS	[M-H]-	154.477	30932474
DeepCCS	[M-2H]-	187.361	30932474
DeepCCS	[M+Na]+	162.897	30932474
AllCCS	[M+H]+	153.9	32859911
AllCCS	[M+H-H2O]+	150.0	32859911
AllCCS	[M+NH4]+	157.4	32859911
AllCCS	[M+Na]+	158.4	32859911
AllCCS	[M-H]-	154.8	32859911
AllCCS	[M+Na-2H]-	155.1	32859911
AllCCS	[M+HCOO]-	155.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1'-Acetoxychavicol	CC(=O)O[C@@H](C=C)C1=CC=C(OC(C)=O)C=C1	2514.5	Standard polar	33892256
1'-Acetoxychavicol	CC(=O)O[C@@H](C=C)C1=CC=C(OC(C)=O)C=C1	1730.0	Standard non polar	33892256
1'-Acetoxychavicol	CC(=O)O[C@@H](C=C)C1=CC=C(OC(C)=O)C=C1	1675.8	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 - 1'-Acetoxychavicol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0900000000-1abea45849299f24ade5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1'-Acetoxychavicol 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'-Acetoxychavicol 10V, Negative-QTOF	splash10-000x-1960000000-cdce662dd688b22d71d9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 20V, Negative-QTOF	splash10-000x-2920000000-086e7d1ca558654bc999	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 40V, Negative-QTOF	splash10-052e-6900000000-bb4d8adbbf61bce88907	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 10V, Negative-QTOF	splash10-0a4l-9620000000-6a6a1fa37916a3b9a0ea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 20V, Negative-QTOF	splash10-0a4i-9100000000-f44a6f5a57c94e8e8e93	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 40V, Negative-QTOF	splash10-052f-9300000000-ef559bb25482dcb0b386	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 10V, Positive-QTOF	splash10-002u-0950000000-bab1e5d60064ed54fd6b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 20V, Positive-QTOF	splash10-004l-0900000000-f79652ac903a15e56eb4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 40V, Positive-QTOF	splash10-001j-1900000000-962bbdcd8eeb60b29c29	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 10V, Positive-QTOF	splash10-000l-0970000000-81735b3654a481b06311	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 20V, Positive-QTOF	splash10-0036-1900000000-9b5975ebd113945e0e7c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1'-Acetoxychavicol 40V, Positive-QTOF	splash10-0007-2900000000-699c26c2e1a06248898e	2021-09-24	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119104

PDB ID

Not Available

ChEBI ID

469

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1466351

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'-Acetoxychavicol (HMDB0041006)

MOL for HMDB0041006 (1'-Acetoxychavicol)

3D MOL for HMDB0041006 (1'-Acetoxychavicol)

3D SDF for HMDB0041006 (1'-Acetoxychavicol)

3D-SDF for HMDB0041006 (1'-Acetoxychavicol)

PDB for HMDB0041006 (1'-Acetoxychavicol)

3D PDB for HMDB0041006 (1'-Acetoxychavicol)

SMILES for HMDB0041006 (1'-Acetoxychavicol)

INCHI for HMDB0041006 (1'-Acetoxychavicol)

Structure for HMDB0041006 (1'-Acetoxychavicol)

3D Structure for HMDB0041006 (1'-Acetoxychavicol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra