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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:57:18 UTC

Update Date

2022-03-07 02:56:57 UTC

HMDB ID

HMDB0041284

Secondary Accession Numbers

HMDB41284

Metabolite Identification

Common Name

2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone

Description

2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone, also known as 2-(2-methylpropanoyl)-4-prenylphloroglucinol or 2-(3',3'-dimethylallyl)-4-isobutyrylphloroglucinol, 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. 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone has been detected, but not quantified in, alcoholic beverages. This could make 2-methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone.

Structure

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

HMDB0041284
     RDKit          3D
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone
 39 39  0  0  0  0  0  0  0  0999 V2000
    5.0549   -0.2257   -0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    0.7328    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5588    2.1535    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8548    0.4407    0.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767   -0.8697    0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8371   -0.7845   -0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8183   -0.7704   -1.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9610   -0.8600   -2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028   -0.6637   -2.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5813   -0.5737   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954   -0.4727   -2.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5642   -0.5867   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496   -0.4531    0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6368   -0.5107    1.9958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1094   -0.2423    0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1431   -0.3318    1.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2387    1.1715   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253   -0.6954    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310   -0.7054    1.9817 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0908    0.0281   -0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8194   -1.2222    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0567   -0.1197   -1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0026    2.6285    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6146    2.1497    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3032    2.6838   -0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529    1.2609    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -1.2524    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -1.6053   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8870   -0.9517   -1.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4659   -0.6480   -3.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -0.4631   -3.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4336   -0.9448   -0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -0.2543    0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0766   -1.3192    1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0408    0.4928    2.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083    1.1282   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2596    1.6239   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886    1.7974    0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -0.7653    2.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 12 18  2  0
 18 19  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
M  END


  Mrv0541 05061312322D          

 19 19  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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    2.0625    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    0.8250    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   -1.6500    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
    0.7145    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
    0.7145   -0.4125    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    0.0000    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
    2.1434   -0.4125    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   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  2  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041284

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8(2)5-6-10-11(16)7-12(17)13(15(10)19)14(18)9(3)4/h5,7,9,16-17,19H,6H2,1-4H3

> <INCHI_KEY>
IOBXAMCSYCVNET-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.859795082945045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
4.892286494333334

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.526198879181887

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.820630200192947

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6115275217942395

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
75.8477

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041284
     RDKit          3D
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone
 39 39  0  0  0  0  0  0  0  0999 V2000
    5.0549   -0.2257   -0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    0.7328    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5588    2.1535    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8548    0.4407    0.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767   -0.8697    0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8371   -0.7845   -0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8183   -0.7704   -1.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9610   -0.8600   -2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028   -0.6637   -2.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5813   -0.5737   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954   -0.4727   -2.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5642   -0.5867   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496   -0.4531    0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6368   -0.5107    1.9958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1094   -0.2423    0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1431   -0.3318    1.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2387    1.1715   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253   -0.6954    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310   -0.7054    1.9817 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0908    0.0281   -0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8194   -1.2222    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0567   -0.1197   -1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0026    2.6285    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6146    2.1497    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3032    2.6838   -0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529    1.2609    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -1.2524    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -1.6053   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8870   -0.9517   -1.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4659   -0.6480   -3.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -0.4631   -3.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4336   -0.9448   -0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -0.2543    0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0766   -1.3192    1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0408    0.4928    2.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083    1.1282   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2596    1.6239   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886    1.7974    0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -0.7653    2.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 12 18  2  0
 18 19  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  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   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   4.620   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       0.000   1.540   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       2.667   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  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+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       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    9                                                            
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7   11   12                                                       
CONECT    8    1    2    5                                                  
CONECT    9    3    4   14                                                  
CONECT   10    6   11   15                                                  
CONECT   11    7   10   16                                                  
CONECT   12    7   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14    9   13   18                                                  
CONECT   15   10   13   19                                                  
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0041284
HETATM    1  C1  UNL     1       5.055  -0.226  -0.347  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.082   0.733   0.240  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.559   2.154   0.413  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.855   0.441   0.614  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.177  -0.870   0.538  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.837  -0.784  -0.138  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.818  -0.770  -1.510  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.961  -0.860  -2.274  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.403  -0.664  -2.166  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.581  -0.574  -1.435  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.795  -0.473  -2.089  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.564  -0.587  -0.066  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.750  -0.453   0.745  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.637  -0.511   1.996  1.00  0.00           O  
HETATM   15  C12 UNL     1      -4.109  -0.242   0.222  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.143  -0.332   1.358  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.239   1.171  -0.385  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.325  -0.695   0.617  1.00  0.00           C  
HETATM   19  O4  UNL     1      -0.331  -0.705   1.982  1.00  0.00           O  
HETATM   20  H1  UNL     1       6.091   0.028  -0.012  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.819  -1.222   0.030  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.057  -0.120  -1.435  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.003   2.628   1.244  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.615   2.150   0.683  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.303   2.684  -0.513  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.253   1.261   1.036  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.017  -1.252   1.550  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.825  -1.605  -0.050  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.887  -0.952  -1.961  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.466  -0.648  -3.251  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.812  -0.463  -3.097  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.434  -0.945  -0.549  1.00  0.00           H  
HETATM   33  H14 UNL     1      -6.132  -0.254   0.875  1.00  0.00           H  
HETATM   34  H15 UNL     1      -5.077  -1.319   1.857  1.00  0.00           H  
HETATM   35  H16 UNL     1      -5.041   0.493   2.064  1.00  0.00           H  
HETATM   36  H17 UNL     1      -4.808   1.128  -1.328  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.260   1.624  -0.521  1.00  0.00           H  
HETATM   38  H19 UNL     1      -4.789   1.797   0.365  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.483  -0.765   2.532  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4    4
CONECT    3   23   24   25
CONECT    4    5   26
CONECT    5    6   27   28
CONECT    6    7    7   18
CONECT    7    8    9
CONECT    8   29
CONECT    9   10   10   30
CONECT   10   11   12
CONECT   11   31
CONECT   12   13   18   18
CONECT   13   14   14   15
CONECT   15   16   17   32
CONECT   16   33   34   35
CONECT   17   36   37   38
CONECT   18   19
CONECT   19   39
END

HMDB0041284
     RDKit          3D
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone
 39 39  0  0  0  0  0  0  0  0999 V2000
    5.0549   -0.2257   -0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    0.7328    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5588    2.1535    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8548    0.4407    0.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767   -0.8697    0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8371   -0.7845   -0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8183   -0.7704   -1.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9610   -0.8600   -2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028   -0.6637   -2.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5813   -0.5737   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954   -0.4727   -2.0890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5642   -0.5867   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496   -0.4531    0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6368   -0.5107    1.9958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1094   -0.2423    0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1431   -0.3318    1.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2387    1.1715   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253   -0.6954    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310   -0.7054    1.9817 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0908    0.0281   -0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8194   -1.2222    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0567   -0.1197   -1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0026    2.6285    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6146    2.1497    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3032    2.6838   -0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529    1.2609    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -1.2524    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -1.6053   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8870   -0.9517   -1.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4659   -0.6480   -3.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -0.4631   -3.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4336   -0.9448   -0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -0.2543    0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0766   -1.3192    1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0408    0.4928    2.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083    1.1282   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2596    1.6239   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886    1.7974    0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -0.7653    2.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 12 18  2  0
 18 19  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(2-Methylpropanoyl)-4-prenylphloroglucinol	ChEBI
2-(2-Methylpropionyl)-4-prenylphloroglucinol	ChEBI
2-(3',3'-Dimethylallyl)-4-isobutyrylphloroglucinol	ChEBI
2-Isobutanoyl-4-prenylphloroglucinol	ChEBI
4-Prenylphlorisobutanophenone	ChEBI
Dimethylallyl-phlorisobutyrophenone	ChEBI
2-Methyl-1-(2,4,6-trihydroxy-3-(3-methyl2-butenyl)phenyl)-1-propanone	MeSH
UTX-53	MeSH

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one

Traditional Name

2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one

CAS Registry Number

35932-36-6

SMILES

CC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O

InChI Identifier

InChI=1S/C15H20O4/c1-8(2)5-6-10-11(16)7-12(17)13(15(10)19)14(18)9(3)4/h5,7,9,16-17,19H,6H2,1-4H3

InChI Key

IOBXAMCSYCVNET-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
Acylphloroglucinol derivative
Benzenetriol
Phloroglucinol derivative
Phenylpropane
Aryl alkyl ketone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Polyol
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0041284)

Cellular substructure

Membrane (HMDB: HMDB0041284)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041284)

Source

Exogenous

Food

Food (HMDB: HMDB0041284)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Not Available

Nutrient (HMDB: HMDB0041284)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	166 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.65 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	2.79	ALOGPS
logP	4.89	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.85 m³·mol⁻¹	ChemAxon
Polarizability	28.86 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]+	166.115	31661259
DarkChem	[M-H]-	160.669	31661259
DeepCCS	[M+H]+	167.583	30932474
DeepCCS	[M-H]-	165.225	30932474
DeepCCS	[M-2H]-	198.11	30932474
DeepCCS	[M+Na]+	173.676	30932474
AllCCS	[M+H]+	160.6	32859911
AllCCS	[M+H-H2O]+	157.0	32859911
AllCCS	[M+NH4]+	163.9	32859911
AllCCS	[M+Na]+	164.8	32859911
AllCCS	[M-H]-	164.6	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	165.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone	CC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O	3189.4	Standard polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone	CC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O	1994.0	Standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone	CC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O	2156.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TMS,isomer #1	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O	2100.9	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C(C(=O)C(C)C)=C1O	2100.8	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TMS,isomer #3	CC(C)=CCC1=C(O)C=C(O)C(C(=O)C(C)C)=C1O[Si](C)(C)C	2076.8	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O	2133.5	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TMS,isomer #2	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C	2099.1	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TMS,isomer #3	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C(C(=O)C(C)C)=C1O[Si](C)(C)C	2118.8	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C	2197.1	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TBDMS,isomer #1	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O	2338.2	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(C(=O)C(C)C)=C1O	2346.8	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C(O)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C	2332.8	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O	2621.2	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C	2593.4	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TBDMS,isomer #3	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C	2611.2	Semi standard non polar	33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C	2839.2	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 - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1090000000-db007320da1a609b6c60	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone GC-MS (3 TMS) - 70eV, Positive	splash10-014i-1100900000-06a36b45b3e6cca15dbc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 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 - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 10V, Positive-QTOF	splash10-014i-1190000000-dd8776c84ddbc96a5849	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 20V, Positive-QTOF	splash10-00xr-6190000000-cbb3770a0613be6b81a1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 40V, Positive-QTOF	splash10-00xu-9400000000-9b4094f96a37da2b47a4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 10V, Negative-QTOF	splash10-03di-0190000000-b276ef77545bf0dc16ea	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 20V, Negative-QTOF	splash10-0006-3940000000-d0fd3234340acdba6547	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 40V, Negative-QTOF	splash10-00gl-6910000000-0e04604a367f1b06b18d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 10V, Negative-QTOF	splash10-03di-0090000000-16d43704d08f3756e03a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 20V, Negative-QTOF	splash10-03dl-0890000000-fc221df67d36f563f23e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 40V, Negative-QTOF	splash10-0006-3900000000-0933a7383709c57801ea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 10V, Positive-QTOF	splash10-014i-2090000000-1ccde9a1cf4567f922b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 20V, Positive-QTOF	splash10-014i-3690000000-fd313b1b1d9d29b6296e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 40V, Positive-QTOF	splash10-014i-3920000000-9044653fe1e124d1504f	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

FDB021200

KNApSAcK ID

C00057368

Chemspider ID

24775685

KEGG Compound ID

Not Available

BioCyc ID

4-PRENYLPHLORISOBUTYROPHENONE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13411738

PDB ID

Not Available

ChEBI ID

134342

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1891081

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 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone (HMDB0041284)

MOL for HMDB0041284 (2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone)

3D MOL for HMDB0041284 (2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone)

3D SDF for HMDB0041284 (2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone)

3D-SDF for HMDB0041284 (2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone)

PDB for HMDB0041284 (2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone)

3D PDB for HMDB0041284 (2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone)

SMILES for HMDB0041284 (2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone)

INCHI for HMDB0041284 (2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone)

Structure for HMDB0041284 (2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone)

3D Structure for HMDB0041284 (2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra