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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:39 UTC

Update Date

2022-03-07 02:53:23 UTC

HMDB ID

HMDB0032589

Secondary Accession Numbers

HMDB32589

Metabolite Identification

Common Name

1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone

Description

1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone, also known as 4'-hydroxy-3'-isovalerylacetophenone, 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-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone.

Structure

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

HMDB0032589
     RDKit          3D
1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.6044    1.4194   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593    0.1355   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0127   -0.5390   -1.3599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8174   -0.3970   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036   -1.6233   -1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2423   -2.1630   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534   -1.5032   -0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0019   -2.0528   -0.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5078   -0.2978    0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4655    0.4447    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823    1.5708    1.4646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466    0.1225    1.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.9169    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2760    0.5121    0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7111    0.6178   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8013    0.2237    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    1.2885    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7754    2.1117    0.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2832    1.9777   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -2.1691   -1.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9754   -3.1171   -1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -2.9579   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1286   -0.9306    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    0.4981    2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7737    1.9964    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9069    0.3408   -0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7811    1.3258    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2736   -0.4441    1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3745    1.2394   -1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    0.7113   -1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0245   -0.4450   -1.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0541    1.1867    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  2  0
 16  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  0
 14 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
M  END


  Mrv0541 05061306352D          

 16 16  0  0  0  0            999 V2000
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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    2.0625    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
   -1.4289    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   -0.4125    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
   -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 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
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  2  0  0  0  0
 13  6  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032589

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O3/c1-8(2)6-13(16)11-7-10(9(3)14)4-5-12(11)15/h4-5,7-8,15H,6H2,1-3H3

> <INCHI_KEY>
SXPHHWILAWXFLE-UHFFFAOYSA-N

> <FORMULA>
C13H16O3

> <MOLECULAR_WEIGHT>
220.2643

> <EXACT_MASS>
220.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.71493505430097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(5-acetyl-2-hydroxyphenyl)-3-methylbutan-1-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.8670991399999997

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.515394334083275

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.431682603556437

> <JCHEM_PKA_STRONGEST_BASIC>
-5.1663032390210235

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
62.62100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(5-acetyl-2-hydroxyphenyl)-3-methylbutan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032589
     RDKit          3D
1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.6044    1.4194   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593    0.1355   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0127   -0.5390   -1.3599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8174   -0.3970   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036   -1.6233   -1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2423   -2.1630   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534   -1.5032   -0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0019   -2.0528   -0.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5078   -0.2978    0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4655    0.4447    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823    1.5708    1.4646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466    0.1225    1.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.9169    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2760    0.5121    0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7111    0.6178   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8013    0.2237    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    1.2885    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7754    2.1117    0.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2832    1.9777   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -2.1691   -1.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9754   -3.1171   -1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -2.9579   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1286   -0.9306    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    0.4981    2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7737    1.9964    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9069    0.3408   -0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7811    1.3258    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2736   -0.4441    1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3745    1.2394   -1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    0.7113   -1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0245   -0.4450   -1.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0541    1.1867    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  2  0
 16  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  0
 14 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  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      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    5   10                                                       
CONECT    5    4   12                                                       
CONECT    6    8   13                                                       
CONECT    7   10   11                                                       
CONECT    8    1    2    6                                                  
CONECT    9    3   10   14                                                  
CONECT   10    4    7    9                                                  
CONECT   11    7   12   13                                                  
CONECT   12    5   11   15                                                  
CONECT   13    6   11   16                                                  
CONECT   14    9                                                            
CONECT   15   12                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0032589
HETATM    1  C1  UNL     1       4.604   1.419  -0.152  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.159   0.136  -0.718  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.013  -0.539  -1.360  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.817  -0.397  -0.584  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.504  -1.623  -1.167  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.242  -2.163  -1.057  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.253  -1.503  -0.367  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.002  -2.053  -0.266  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.508  -0.298   0.223  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.466   0.445   0.974  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.082   1.571   1.465  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.847   0.122   1.279  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.861   0.917   0.442  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.276   0.512   0.834  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.711   0.618  -1.019  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.801   0.224   0.093  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.197   1.289   0.785  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.775   2.112   0.084  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.283   1.978  -0.836  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.267  -2.169  -1.720  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.975  -3.117  -1.503  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.202  -2.958  -0.707  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.129  -0.931   1.349  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.075   0.498   2.335  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.774   1.996   0.620  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.907   0.341  -0.057  1.00  0.00           H  
HETATM   27  H11 UNL     1      -4.781   1.326   1.406  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.274  -0.444   1.414  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.374   1.239  -1.629  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.669   0.711  -1.318  1.00  0.00           H  
HETATM   31  H15 UNL     1      -3.025  -0.445  -1.200  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.054   1.187   0.548  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    4
CONECT    4    5    5   16
CONECT    5    6   20
CONECT    6    7    7   21
CONECT    7    8    9
CONECT    8   22
CONECT    9   10   16   16
CONECT   10   11   11   12
CONECT   12   13   23   24
CONECT   13   14   15   25
CONECT   14   26   27   28
CONECT   15   29   30   31
CONECT   16   32
END

HMDB0032589
     RDKit          3D
1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.6044    1.4194   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593    0.1355   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0127   -0.5390   -1.3599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8174   -0.3970   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036   -1.6233   -1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2423   -2.1630   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534   -1.5032   -0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0019   -2.0528   -0.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5078   -0.2978    0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4655    0.4447    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823    1.5708    1.4646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466    0.1225    1.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.9169    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2760    0.5121    0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7111    0.6178   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8013    0.2237    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    1.2885    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7754    2.1117    0.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2832    1.9777   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -2.1691   -1.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9754   -3.1171   -1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -2.9579   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1286   -0.9306    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    0.4981    2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7737    1.9964    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9069    0.3408   -0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7811    1.3258    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2736   -0.4441    1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3745    1.2394   -1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    0.7113   -1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0245   -0.4450   -1.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0541    1.1867    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  2  0
 16  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  0
 14 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-Hydroxy-3'-isovalerylacetophenone	HMDB
4-Hydroxy-3-isovalerylacetophenone	HMDB

Chemical Formula

C₁₃H₁₆O₃

Average Molecular Weight

220.2643

Monoisotopic Molecular Weight

220.109944378

IUPAC Name

1-(5-acetyl-2-hydroxyphenyl)-3-methylbutan-1-one

Traditional Name

1-(5-acetyl-2-hydroxyphenyl)-3-methylbutan-1-one

CAS Registry Number

62458-64-4

SMILES

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

InChI Identifier

InChI=1S/C13H16O3/c1-8(2)6-13(16)11-7-10(9(3)14)4-5-12(11)15/h4-5,7-8,15H,6H2,1-3H3

InChI Key

SXPHHWILAWXFLE-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
Acetophenone
Aryl alkyl ketone
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032589)
Cell membrane (HMDB: HMDB0032589)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032589)

Source

Endogenous

Endogenous (HMDB: HMDB0032589)

Plant

Plant (HMDB: HMDB0032589)

Exogenous

Food

Food (HMDB: HMDB0032589)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Exogenous (HMDB: HMDB0032589)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	94.5 - 96 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	323.6 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	0.16 g/L	ALOGPS
logP	2.6	ALOGPS
logP	2.87	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.62 m³·mol⁻¹	ChemAxon
Polarizability	23.71 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]+	153.824	31661259
DarkChem	[M-H]-	151.485	31661259
DeepCCS	[M+H]+	159.63	30932474
DeepCCS	[M-H]-	157.255	30932474
DeepCCS	[M-2H]-	191.164	30932474
DeepCCS	[M+Na]+	167.374	30932474
AllCCS	[M+H]+	149.2	32859911
AllCCS	[M+H-H2O]+	145.3	32859911
AllCCS	[M+NH4]+	152.9	32859911
AllCCS	[M+Na]+	153.9	32859911
AllCCS	[M-H]-	153.1	32859911
AllCCS	[M+Na-2H]-	153.6	32859911
AllCCS	[M+HCOO]-	154.2	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.	7.17 minutes	32390414
Predicted by Siyang on May 30, 2022	14.645 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	22.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2298.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	421.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	224.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	562.8 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	734.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1101.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	462.6 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	1423.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	418.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	412.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	358.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	323.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	46.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone	CC(C)CC(=O)C1=C(O)C=CC(=C1)C(C)=O	2636.8	Standard polar	33892256
1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone	CC(C)CC(=O)C1=C(O)C=CC(=C1)C(C)=O	1754.1	Standard non polar	33892256
1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone	CC(C)CC(=O)C1=C(O)C=CC(=C1)C(C)=O	1767.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone,1TMS,isomer #1	CC(=O)C1=CC=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1	1906.4	Semi standard non polar	33892256
1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone,1TBDMS,isomer #1	CC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C1	2153.3	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-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-3910000000-37d55bdf2917a9065a5b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone GC-MS (1 TMS) - 70eV, Positive	splash10-00bl-9360000000-e561146b1b468fba272a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 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-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 10V, Positive-QTOF	splash10-00di-1390000000-bd510b366c3ddbc9c804	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 20V, Positive-QTOF	splash10-03di-5920000000-dba39eb3c83aa5c13af1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 40V, Positive-QTOF	splash10-06xy-7900000000-ecc712f223e17a663a84	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 10V, Negative-QTOF	splash10-014i-0190000000-fd1b89711e7f8b472b88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 20V, Negative-QTOF	splash10-014i-3690000000-2633eb5ea18e0cd05ff8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 40V, Negative-QTOF	splash10-05n3-6910000000-929bfdb8b649892432d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 10V, Negative-QTOF	splash10-014i-0090000000-bd11576db9466b984a17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 20V, Negative-QTOF	splash10-014i-3690000000-8aa0856e3039fd3fa562	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 40V, Negative-QTOF	splash10-02t9-5900000000-87da8b113b5345cba53b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 10V, Positive-QTOF	splash10-00di-1590000000-99fbd382d0dd3c58f93f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 20V, Positive-QTOF	splash10-006x-9870000000-8ed9bd76a08055352fce	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone 40V, Positive-QTOF	splash10-03dl-5900000000-7c7d2a5132991d28d73f	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

FDB010526

KNApSAcK ID

C00022704

Chemspider ID

26771417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13308867

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1830391

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-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone (HMDB0032589)

MOL for HMDB0032589 (1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone)

3D MOL for HMDB0032589 (1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone)

3D SDF for HMDB0032589 (1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone)

3D-SDF for HMDB0032589 (1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone)

PDB for HMDB0032589 (1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone)

3D PDB for HMDB0032589 (1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone)

SMILES for HMDB0032589 (1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone)

INCHI for HMDB0032589 (1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone)

Structure for HMDB0032589 (1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone)

3D Structure for HMDB0032589 (1-(5-Acetyl-2-hydroxyphenyl)-3-methyl-1-butanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra