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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:55 UTC

Update Date

2023-02-21 17:19:40 UTC

HMDB ID

HMDB0030770

Secondary Accession Numbers

HMDB30770

Metabolite Identification

Common Name

4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone

Description

4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone, also known as 4'-hydroxy-3',5'-dimethyl-acetophenone or 4-acetyl-2-prenylphenol, 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 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone.

Structure

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

HMDB0030770
     RDKit          3D
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone
 31 31  0  0  0  0  0  0  0  0999 V2000
   -4.2963   -1.0461   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9702    0.2960   -0.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8944    1.1692   -0.7816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6698    0.6221   -0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4628    1.9266    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399    2.2769    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2393    1.3100    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    1.6681    1.4080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344    0.0370    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6425   -0.9699    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6963   -0.8014   -0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9718   -0.6847   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826   -0.7087    1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9618   -0.5150   -1.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701   -0.3255   -0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7502   -1.8408   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0085   -1.1248   -2.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3872   -1.2400   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839    2.6274    0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0524    3.2732    1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    2.5983    1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945   -0.9118    1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1702   -1.9859    0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3682   -0.7784   -1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532   -0.3851    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9654   -0.1034    1.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -1.7633    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3202   -1.4700   -1.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8354    0.0750   -0.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4688    0.1139   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975   -1.3387   -0.4636 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  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  2  0
 15  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
M  END


  Mrv0541 05061305292D          

 15 15  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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    1.4289    0.8250    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
    0.0000   -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
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  4  2  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12  5  1  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  2  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030770

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C=CC(=C1)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O2/c1-9(2)4-5-12-8-11(10(3)14)6-7-13(12)15/h4,6-8,15H,5H2,1-3H3

> <INCHI_KEY>
QJAPFSSVKIZTMR-UHFFFAOYSA-N

> <FORMULA>
C13H16O2

> <MOLECULAR_WEIGHT>
204.2649

> <EXACT_MASS>
204.115029756

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.38650371705419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]ethan-1-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.9558950123333343

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.680657963612934

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.5921789641686965

> <JCHEM_PKA_STRONGEST_BASIC>
-6.978264538030907

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
62.68450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]ethanone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030770
     RDKit          3D
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone
 31 31  0  0  0  0  0  0  0  0999 V2000
   -4.2963   -1.0461   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9702    0.2960   -0.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8944    1.1692   -0.7816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6698    0.6221   -0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4628    1.9266    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399    2.2769    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2393    1.3100    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    1.6681    1.4080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344    0.0370    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6425   -0.9699    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6963   -0.8014   -0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9718   -0.6847   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826   -0.7087    1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9618   -0.5150   -1.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701   -0.3255   -0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7502   -1.8408   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0085   -1.1248   -2.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3872   -1.2400   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839    2.6274    0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0524    3.2732    1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    2.5983    1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945   -0.9118    1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1702   -1.9859    0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3682   -0.7784   -1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532   -0.3851    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9654   -0.1034    1.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -1.7633    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3202   -1.4700   -1.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8354    0.0750   -0.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4688    0.1139   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975   -1.3387   -0.4636 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  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  2  0
 15  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   4.620   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   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
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5    9                                                       
CONECT    5    4   12                                                       
CONECT    6    7   11                                                       
CONECT    7    6   13                                                       
CONECT    8   11   12                                                       
CONECT    9    1    2    4                                                  
CONECT   10    3   11   14                                                  
CONECT   11    6    8   10                                                  
CONECT   12    5    8   13                                                  
CONECT   13    7   12   15                                                  
CONECT   14   10                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0030770
HETATM    1  C1  UNL     1      -4.296  -1.046  -1.232  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.970   0.296  -0.721  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.894   1.169  -0.782  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.670   0.622  -0.173  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.463   1.927   0.293  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.240   2.277   0.822  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.239   1.310   0.877  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.983   1.668   1.408  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.434   0.037   0.425  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.642  -0.970   0.496  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.696  -0.801  -0.515  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.972  -0.685  -0.180  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.483  -0.709   1.192  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.962  -0.515  -1.294  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.670  -0.325  -0.113  1.00  0.00           C  
HETATM   16  H1  UNL     1      -3.750  -1.841  -0.660  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.008  -1.125  -2.300  1.00  0.00           H  
HETATM   18  H3  UNL     1      -5.387  -1.240  -1.102  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.284   2.627   0.219  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.052   3.273   1.187  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.168   2.598   1.753  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.094  -0.912   1.530  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.170  -1.986   0.458  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.368  -0.778  -1.555  1.00  0.00           H  
HETATM   25  H10 UNL     1       4.553  -0.385   1.225  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.965  -0.103   1.929  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.475  -1.763   1.602  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.320  -1.470  -1.696  1.00  0.00           H  
HETATM   29  H14 UNL     1       4.835   0.075  -0.944  1.00  0.00           H  
HETATM   30  H15 UNL     1       3.469   0.114  -2.069  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.797  -1.339  -0.464  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5    5   15
CONECT    5    6   19
CONECT    6    7    7   20
CONECT    7    8    9
CONECT    8   21
CONECT    9   10   15   15
CONECT   10   11   22   23
CONECT   11   12   12   24
CONECT   12   13   14
CONECT   13   25   26   27
CONECT   14   28   29   30
CONECT   15   31
END

HMDB0030770
     RDKit          3D
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone
 31 31  0  0  0  0  0  0  0  0999 V2000
   -4.2963   -1.0461   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9702    0.2960   -0.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8944    1.1692   -0.7816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6698    0.6221   -0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4628    1.9266    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399    2.2769    0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2393    1.3100    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    1.6681    1.4080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344    0.0370    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6425   -0.9699    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6963   -0.8014   -0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9718   -0.6847   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826   -0.7087    1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9618   -0.5150   -1.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701   -0.3255   -0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7502   -1.8408   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0085   -1.1248   -2.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3872   -1.2400   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839    2.6274    0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0524    3.2732    1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683    2.5983    1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945   -0.9118    1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1702   -1.9859    0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3682   -0.7784   -1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532   -0.3851    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9654   -0.1034    1.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -1.7633    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3202   -1.4700   -1.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8354    0.0750   -0.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4688    0.1139   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975   -1.3387   -0.4636 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  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  2  0
 15  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]ethanone, 9ci	HMDB
4'-HYDROXY-3',5'-dimethyl-acetophenone	HMDB
4'-Hydroxy-3',5'-dimethylacetophenone	HMDB
4'-Hydroxy-3'-prenylacetophenone	HMDB
4-Acetyl-2-prenylphenol	HMDB
4-H-3-(MB)AP	HMDB
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone	MeSH

Chemical Formula

C₁₃H₁₆O₂

Average Molecular Weight

204.2649

Monoisotopic Molecular Weight

204.115029756

IUPAC Name

1-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]ethan-1-one

Traditional Name

1-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]ethanone

CAS Registry Number

26932-05-8

SMILES

CC(C)=CCC1=C(O)C=CC(=C1)C(C)=O

InChI Identifier

InChI=1S/C13H16O2/c1-9(2)4-5-12-8-11(10(3)14)6-7-13(12)15/h4,6-8,15H,5H2,1-3H3

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

acetophenones (CHEBI:28242 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030770)
Cell membrane (HMDB: HMDB0030770)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030770)

Source

Endogenous

Endogenous (HMDB: HMDB0030770)

Plant

Plant (HMDB: HMDB0030770)

Exogenous

Food

Food (HMDB: HMDB0030770)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	93 - 94 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	148.1 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	0.23 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.96	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.59	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.68 m³·mol⁻¹	ChemAxon
Polarizability	23.39 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	150.717	31661259
DarkChem	[M-H]-	146.747	31661259
DeepCCS	[M+H]+	147.629	30932474
DeepCCS	[M-H]-	145.271	30932474
DeepCCS	[M-2H]-	179.688	30932474
DeepCCS	[M+Na]+	155.002	30932474
AllCCS	[M+H]+	144.7	32859911
AllCCS	[M+H-H2O]+	140.6	32859911
AllCCS	[M+NH4]+	148.6	32859911
AllCCS	[M+Na]+	149.7	32859911
AllCCS	[M-H]-	148.0	32859911
AllCCS	[M+Na-2H]-	148.5	32859911
AllCCS	[M+HCOO]-	149.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone	CC(C)=CCC1=C(O)C=CC(=C1)C(C)=O	2613.1	Standard polar	33892256
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone	CC(C)=CCC1=C(O)C=CC(=C1)C(C)=O	1732.1	Standard non polar	33892256
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone	CC(C)=CCC1=C(O)C=CC(=C1)C(C)=O	1849.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone,1TMS,isomer #1	CC(=O)C1=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C1	1860.2	Semi standard non polar	33892256
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone,1TBDMS,isomer #1	CC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1	2114.6	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 - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01p6-4900000000-9cbfdba7ebf9a6361d98	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone GC-MS (1 TMS) - 70eV, Positive	splash10-03k9-6290000000-af3dd04185a385fada52	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone , positive-QTOF	splash10-0002-1900000000-92dee8ca08bdfab6ffab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Negative-QTOF	splash10-06tb-0900000000-4c53b81469de62698ab0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Negative-QTOF	splash10-0002-0910000000-02bf584620735a5d0b6f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Positive-QTOF	splash10-0002-0910000000-8fdd6b705ab0193678b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Positive-QTOF	splash10-0002-0900000000-6b0fe0aaec869b1d340b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Negative-QTOF	splash10-0udi-0390000000-c625af71f47cfc663be4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Positive-QTOF	splash10-0a4i-0900000000-d5e7024da264cffccf26	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Positive-QTOF	splash10-0a4i-1690000000-4a14777a6cda9fcecda3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Positive-QTOF	splash10-0cdj-4930000000-0296abc39fac52664ead	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Positive-QTOF	splash10-014i-9700000000-2065daeb365f421dc74a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Negative-QTOF	splash10-0udi-0190000000-c7b6432ab7a81d313617	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Negative-QTOF	splash10-0udi-0490000000-e0373680ed7ce6a9ee17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Negative-QTOF	splash10-000i-3900000000-1f2ecae9577454ad3bc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Positive-QTOF	splash10-052b-2920000000-cfd053bee8ded4297efd	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Positive-QTOF	splash10-0006-9810000000-444554f46a35456aa6d0	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Positive-QTOF	splash10-052f-9800000000-4e793c744880d36928a5	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Negative-QTOF	splash10-0udi-0090000000-7f5adf74d70ecbe2137c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Negative-QTOF	splash10-0udi-2590000000-d67c3f34fec59f1701de	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Negative-QTOF	splash10-014l-4900000000-2d63f142d0d87eb77fc8	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442916

PDB ID

Not Available

ChEBI ID

585101

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1822621

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 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone (HMDB0030770)

MOL for HMDB0030770 (4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone)

3D MOL for HMDB0030770 (4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone)

3D SDF for HMDB0030770 (4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone)

3D-SDF for HMDB0030770 (4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone)

PDB for HMDB0030770 (4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone)

3D PDB for HMDB0030770 (4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone)

SMILES for HMDB0030770 (4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone)

INCHI for HMDB0030770 (4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone)

Structure for HMDB0030770 (4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone)

3D Structure for HMDB0030770 (4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra