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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:19 UTC

Update Date

2022-03-07 02:52:38 UTC

HMDB ID

HMDB0030668

Secondary Accession Numbers

HMDB30668

Metabolite Identification

Common Name

1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione

Description

1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione, also known as 2,4,6-trimethoxybenzoylacetone or eugenone, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review very few articles have been published on 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione.

Structure

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

HMDB0030668
     RDKit          3D
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.7393   -0.1958   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7311   -1.1054    0.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4176   -0.6504    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0994    0.6304   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767    1.0163   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    2.3343   -0.4297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4467    3.2376   -0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2163    0.1108    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089    0.5487    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347    1.0417    1.3338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354    0.4061   -0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8109    0.9102   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608    0.0110   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0380    2.1080   -0.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786   -1.1971    0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229   -2.0971    0.9829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5222   -3.4129    1.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117   -1.5507    0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6284    0.0699   -1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6656    0.7594    0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7556   -0.5868    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806    1.3259   -0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1759    3.3745    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680    4.2174   -0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385    2.8218   -1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308    0.9861   -1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4053   -0.6480   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3083    0.2582    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7953    0.1728   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488   -1.0642   -0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215   -3.8542    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534   -4.0610    1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2636   -3.3550    2.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589   -2.5623    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
M  END


  Mrv0541 05061305252D          

 18 18  0  0  0  0            999 V2000
   -0.7145   -2.8875    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
    2.1434   -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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13 10  1  0  0  0  0
 13 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14  8  2  0  0  0  0
 15 10  2  0  0  0  0
 16  2  1  0  0  0  0
 16  9  1  0  0  0  0
 17  3  1  0  0  0  0
 17 11  1  0  0  0  0
 18  4  1  0  0  0  0
 18 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030668

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O5/c1-8(14)5-10(15)13-11(17-3)6-9(16-2)7-12(13)18-4/h6-7H,5H2,1-4H3

> <INCHI_KEY>
ZYRBXTNFHYZHSK-UHFFFAOYSA-N

> <FORMULA>
C13H16O5

> <MOLECULAR_WEIGHT>
252.2631

> <EXACT_MASS>
252.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.369042534282897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,4,6-trimethoxyphenyl)butane-1,3-dione

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
1.2797335063333333

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.125976824786449

> <JCHEM_PKA_STRONGEST_BASIC>
-4.405694594532894

> <JCHEM_POLAR_SURFACE_AREA>
61.83000000000001

> <JCHEM_REFRACTIVITY>
65.74560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,4,6-trimethoxyphenyl)butane-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030668
     RDKit          3D
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.7393   -0.1958   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7311   -1.1054    0.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4176   -0.6504    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0994    0.6304   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767    1.0163   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    2.3343   -0.4297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4467    3.2376   -0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2163    0.1108    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089    0.5487    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347    1.0417    1.3338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354    0.4061   -0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8109    0.9102   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608    0.0110   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0380    2.1080   -0.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786   -1.1971    0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229   -2.0971    0.9829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5222   -3.4129    1.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117   -1.5507    0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6284    0.0699   -1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6656    0.7594    0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7556   -0.5868    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806    1.3259   -0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1759    3.3745    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680    4.2174   -0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385    2.8218   -1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308    0.9861   -1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4053   -0.6480   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3083    0.2582    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7953    0.1728   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488   -1.0642   -0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215   -3.8542    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534   -4.0610    1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2636   -3.3550    2.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589   -2.5623    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  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  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5    8   10                                                       
CONECT    6    9   11                                                       
CONECT    7    9   12                                                       
CONECT    8    1    5   14                                                  
CONECT    9    6    7   16                                                  
CONECT   10    5   13   15                                                  
CONECT   11    6   13   17                                                  
CONECT   12    7   13   18                                                  
CONECT   13   10   11   12                                                  
CONECT   14    8                                                            
CONECT   15   10                                                            
CONECT   16    2    9                                                       
CONECT   17    3   11                                                       
CONECT   18    4   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0030668
HETATM    1  C1  UNL     1      -4.739  -0.196  -0.161  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.731  -1.105   0.206  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.418  -0.650   0.215  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.099   0.630  -0.118  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.777   1.016  -0.089  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.434   2.334  -0.430  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.447   3.238  -0.795  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.216   0.111   0.276  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.609   0.549   0.298  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.135   1.042   1.334  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.435   0.406  -0.949  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.811   0.910  -0.689  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.961   0.011  -0.390  1.00  0.00           C  
HETATM   14  O4  UNL     1       4.038   2.108  -0.714  1.00  0.00           O  
HETATM   15  C11 UNL     1      -0.079  -1.197   0.619  1.00  0.00           C  
HETATM   16  O5  UNL     1       0.923  -2.097   0.983  1.00  0.00           O  
HETATM   17  C12 UNL     1       0.522  -3.413   1.317  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.412  -1.551   0.579  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.628   0.070  -1.220  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.666   0.759   0.438  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.756  -0.587   0.074  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.881   1.326  -0.399  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.176   3.375   0.032  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.968   4.217  -0.976  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.939   2.822  -1.713  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.931   0.986  -1.757  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.405  -0.648  -1.231  1.00  0.00           H  
HETATM   28  H10 UNL     1       5.308   0.258   0.654  1.00  0.00           H  
HETATM   29  H11 UNL     1       5.795   0.173  -1.110  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.649  -1.064  -0.425  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.022  -3.854   0.432  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.353  -4.061   1.603  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.264  -3.355   2.124  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.659  -2.562   0.843  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   22
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   23   24   25
CONECT    8    9   15
CONECT    9   10   10   11
CONECT   11   12   26   27
CONECT   12   13   14   14
CONECT   13   28   29   30
CONECT   15   16   18   18
CONECT   16   17
CONECT   17   31   32   33
CONECT   18   34
END

HMDB0030668
     RDKit          3D
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.7393   -0.1958   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7311   -1.1054    0.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4176   -0.6504    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0994    0.6304   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767    1.0163   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    2.3343   -0.4297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4467    3.2376   -0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2163    0.1108    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089    0.5487    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347    1.0417    1.3338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354    0.4061   -0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8109    0.9102   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608    0.0110   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0380    2.1080   -0.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786   -1.1971    0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229   -2.0971    0.9829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5222   -3.4129    1.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117   -1.5507    0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6284    0.0699   -1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6656    0.7594    0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7556   -0.5868    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806    1.3259   -0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1759    3.3745    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680    4.2174   -0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385    2.8218   -1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308    0.9861   -1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4053   -0.6480   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3083    0.2582    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7953    0.1728   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488   -1.0642   -0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215   -3.8542    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534   -4.0610    1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2636   -3.3550    2.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589   -2.5623    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4,6-Trimethoxybenzoylacetone	HMDB
Eugenone	HMDB

Chemical Formula

C₁₃H₁₆O₅

Average Molecular Weight

252.2631

Monoisotopic Molecular Weight

252.099773622

IUPAC Name

1-(2,4,6-trimethoxyphenyl)butane-1,3-dione

Traditional Name

1-(2,4,6-trimethoxyphenyl)butane-1,3-dione

CAS Registry Number

480-27-3

SMILES

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

InChI Identifier

InChI=1S/C13H16O5/c1-8(14)5-10(15)13-11(17-3)6-9(16-2)7-12(13)18-4/h6-7H,5H2,1-4H3

InChI Key

ZYRBXTNFHYZHSK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Anisole
Benzoyl
Phenoxy compound
Phenol ether
Aryl alkyl ketone
Methoxybenzene
Alkyl aryl ether
1,3-diketone
1,3-dicarbonyl compound
Monocyclic benzene moiety
Benzenoid
Ether
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	97 - 98 °C	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	0.27 g/L	ALOGPS
logP	1.18	ALOGPS
logP	1.28	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.13	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	65.75 m³·mol⁻¹	ChemAxon
Polarizability	25.37 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
DeepCCS	[M+H]+	164.308	30932474
DeepCCS	[M-H]-	161.95	30932474
DeepCCS	[M-2H]-	194.836	30932474
DeepCCS	[M+Na]+	170.401	30932474
AllCCS	[M+H]+	157.2	32859911
AllCCS	[M+H-H2O]+	153.5	32859911
AllCCS	[M+NH4]+	160.6	32859911
AllCCS	[M+Na]+	161.6	32859911
AllCCS	[M-H]-	159.6	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	160.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione	COC1=CC(OC)=C(C(=O)CC(C)=O)C(OC)=C1	2919.1	Standard polar	33892256
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione	COC1=CC(OC)=C(C(=O)CC(C)=O)C(OC)=C1	1934.6	Standard non polar	33892256
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione	COC1=CC(OC)=C(C(=O)CC(C)=O)C(OC)=C1	1984.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione,1TMS,isomer #1	COC1=CC(OC)=C(C(=O)C=C(C)O[Si](C)(C)C)C(OC)=C1	2104.5	Semi standard non polar	33892256
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione,1TMS,isomer #1	COC1=CC(OC)=C(C(=O)C=C(C)O[Si](C)(C)C)C(OC)=C1	2085.5	Standard non polar	33892256
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione,1TMS,isomer #2	C=C(CC(=O)C1=C(OC)C=C(OC)C=C1OC)O[Si](C)(C)C	2031.1	Semi standard non polar	33892256
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione,1TMS,isomer #2	C=C(CC(=O)C1=C(OC)C=C(OC)C=C1OC)O[Si](C)(C)C	2048.8	Standard non polar	33892256
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione,1TBDMS,isomer #1	COC1=CC(OC)=C(C(=O)C=C(C)O[Si](C)(C)C(C)(C)C)C(OC)=C1	2353.5	Semi standard non polar	33892256
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione,1TBDMS,isomer #1	COC1=CC(OC)=C(C(=O)C=C(C)O[Si](C)(C)C(C)(C)C)C(OC)=C1	2304.9	Standard non polar	33892256
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione,1TBDMS,isomer #2	C=C(CC(=O)C1=C(OC)C=C(OC)C=C1OC)O[Si](C)(C)C(C)(C)C	2263.2	Semi standard non polar	33892256
1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione,1TBDMS,isomer #2	C=C(CC(=O)C1=C(OC)C=C(OC)C=C1OC)O[Si](C)(C)C(C)(C)C	2264.3	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-(2,4,6-Trimethoxyphenyl)-1,3-butanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9750000000-4db0decd9b0a41f8c8b9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 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-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 10V, Positive-QTOF	splash10-0udr-0090000000-38a6917eff9a26908fc4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 20V, Positive-QTOF	splash10-0f79-2090000000-f710261c791ecbe8c6eb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 40V, Positive-QTOF	splash10-014i-6690000000-9e0cf68a7bfdd3fe1e90	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 10V, Negative-QTOF	splash10-0udi-0190000000-35dc01d7e40130084923	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 20V, Negative-QTOF	splash10-0gb9-2960000000-9b7acc6f36dc335f2297	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 40V, Negative-QTOF	splash10-07w9-3920000000-d29fc6b0dd45432ed246	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 10V, Positive-QTOF	splash10-0udi-0190000000-39dfe44c745ced00d086	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 20V, Positive-QTOF	splash10-0002-0910000000-8434623f19ecff3ba8dd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 40V, Positive-QTOF	splash10-0005-5900000000-cadacb5473f29bd0f62b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 10V, Negative-QTOF	splash10-0udi-0090000000-02e16f3c367e7f32658e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 20V, Negative-QTOF	splash10-0pb9-1190000000-ef2825b974d90c19a1ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione 40V, Negative-QTOF	splash10-0a4i-9400000000-ac9de5f47a61f090469e	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

FDB002581

KNApSAcK ID

C00058117

Chemspider ID

4476160

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317271

PDB ID

Not Available

ChEBI ID

169678

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-(2,4,6-Trimethoxyphenyl)-1,3-butanedione (HMDB0030668)

MOL for HMDB0030668 (1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione)

3D MOL for HMDB0030668 (1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione)

3D SDF for HMDB0030668 (1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione)

3D-SDF for HMDB0030668 (1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione)

PDB for HMDB0030668 (1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione)

3D PDB for HMDB0030668 (1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione)

SMILES for HMDB0030668 (1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione)

INCHI for HMDB0030668 (1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione)

Structure for HMDB0030668 (1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione)

3D Structure for HMDB0030668 (1-(2,4,6-Trimethoxyphenyl)-1,3-butanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra