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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:20:33 UTC

Update Date

2022-03-07 02:56:21 UTC

HMDB ID

HMDB0039805

Secondary Accession Numbers

HMDB39805

Metabolite Identification

Common Name

4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone

Description

4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone.

Structure

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

HMDB0039805
     RDKit          3D
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.4361    0.2379    0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582    0.0632   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635    1.2293   -1.3083 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269   -0.3753   -0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7335    0.6114   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652    0.2057   -0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    1.2932   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0387    2.6625   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9893    1.0199    1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396   -0.1942    1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868   -0.3858    2.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5963   -1.1456    0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051   -1.1374   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624   -1.7394    0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0275   -2.1409   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5123    0.0567    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -0.4184    1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282    1.3179    1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -0.7152   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2557    1.6108   -1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -1.4049   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471   -0.3694   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9325    0.9523    0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9001    1.5531   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    0.2705   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    1.2277   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7006    2.7746   -1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640    3.3905   -0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    2.9268    0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125    1.9097    1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614    0.8520    1.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708   -2.1896    0.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1806   -0.9689   -0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0661   -2.0021    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808   -1.0883    1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223   -2.7132    0.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414   -3.1603   -0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -2.1000   -1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798   -1.9170   -1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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
 13  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv0541 05061311242D          

 15 15  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    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
    2.1434    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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    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
    3.5724    2.0625    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
  9  1  1  0  0  0  0
  9  7  1  0  0  0  0
 10  2  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039805

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)CCC1C(C)CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H24O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h9-10,12,14H,5-8H2,1-4H3

> <INCHI_KEY>
QIHMBTNCJUFMCE-UHFFFAOYSA-N

> <FORMULA>
C13H24O2

> <MOLECULAR_WEIGHT>
212.3285

> <EXACT_MASS>
212.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.45054890729083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3-hydroxybutyl)-3,3,5-trimethylcyclohexan-1-one

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.518332411666667

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.609008057103583

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6576190182013586

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
61.91780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3-hydroxybutyl)-3,3,5-trimethylcyclohexan-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0039805
     RDKit          3D
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.4361    0.2379    0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582    0.0632   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635    1.2293   -1.3083 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269   -0.3753   -0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7335    0.6114   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652    0.2057   -0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    1.2932   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0387    2.6625   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9893    1.0199    1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396   -0.1942    1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868   -0.3858    2.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5963   -1.1456    0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051   -1.1374   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624   -1.7394    0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0275   -2.1409   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5123    0.0567    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -0.4184    1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282    1.3179    1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -0.7152   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2557    1.6108   -1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -1.4049   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471   -0.3694   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9325    0.9523    0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9001    1.5531   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    0.2705   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    1.2277   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7006    2.7746   -1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640    3.3905   -0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    2.9268    0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125    1.9097    1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614    0.8520    1.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708   -2.1896    0.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1806   -0.9689   -0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0661   -2.0021    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808   -1.0883    1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223   -2.7132    0.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414   -3.1603   -0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -2.1000   -1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798   -1.9170   -1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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
 13  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 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  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   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       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5    6   10                                                       
CONECT    6    5   12                                                       
CONECT    7    9   11                                                       
CONECT    8   11   13                                                       
CONECT    9    1    7   12                                                  
CONECT   10    2    5   14                                                  
CONECT   11    7    8   15                                                  
CONECT   12    6    9   13                                                  
CONECT   13    3    4    8   12                                             
CONECT   14   10                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0039805
HETATM    1  C1  UNL     1       3.436   0.238   0.885  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.158   0.063  -0.577  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.364   1.229  -1.308  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.727  -0.375  -0.850  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.733   0.611  -0.346  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.665   0.206  -0.604  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.602   1.293  -0.061  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.039   2.662  -0.245  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.989   1.020   1.378  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.840  -0.194   1.327  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.687  -0.386   2.141  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.596  -1.146   0.237  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.105  -1.137  -0.171  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.362  -1.739   0.977  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.028  -2.141  -1.308  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.512   0.057   1.110  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.856  -0.418   1.537  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.228   1.318   1.131  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.821  -0.715  -1.009  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.256   1.611  -1.135  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.628  -1.405  -0.540  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.647  -0.369  -1.977  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.932   0.952   0.693  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.900   1.553  -0.958  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.811   0.270  -1.727  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.540   1.228  -0.651  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.701   2.775  -1.285  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.864   3.390  -0.099  1.00  0.00           H  
HETATM   29  H14 UNL     1      -0.260   2.927   0.502  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.513   1.910   1.745  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.061   0.852   1.992  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.771  -2.190   0.601  1.00  0.00           H  
HETATM   33  H18 UNL     1      -3.181  -0.969  -0.669  1.00  0.00           H  
HETATM   34  H19 UNL     1      -1.066  -2.002   1.823  1.00  0.00           H  
HETATM   35  H20 UNL     1       0.381  -1.088   1.458  1.00  0.00           H  
HETATM   36  H21 UNL     1       0.122  -2.713   0.755  1.00  0.00           H  
HETATM   37  H22 UNL     1      -0.841  -3.160  -0.916  1.00  0.00           H  
HETATM   38  H23 UNL     1      -2.001  -2.100  -1.859  1.00  0.00           H  
HETATM   39  H24 UNL     1      -0.180  -1.917  -1.997  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4   19
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   13   25
CONECT    7    8    9   26
CONECT    8   27   28   29
CONECT    9   10   30   31
CONECT   10   11   11   12
CONECT   12   13   32   33
CONECT   13   14   15
CONECT   14   34   35   36
CONECT   15   37   38   39
END

HMDB0039805
     RDKit          3D
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.4361    0.2379    0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582    0.0632   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635    1.2293   -1.3083 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269   -0.3753   -0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7335    0.6114   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652    0.2057   -0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    1.2932   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0387    2.6625   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9893    1.0199    1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396   -0.1942    1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868   -0.3858    2.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5963   -1.1456    0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051   -1.1374   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624   -1.7394    0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0275   -2.1409   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5123    0.0567    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -0.4184    1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282    1.3179    1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -0.7152   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2557    1.6108   -1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -1.4049   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471   -0.3694   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9325    0.9523    0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9001    1.5531   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    0.2705   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    1.2277   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7006    2.7746   -1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640    3.3905   -0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    2.9268    0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125    1.9097    1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614    0.8520    1.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708   -2.1896    0.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1806   -0.9689   -0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0661   -2.0021    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808   -1.0883    1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223   -2.7132    0.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414   -3.1603   -0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -2.1000   -1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798   -1.9170   -1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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
 13  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₂₄O₂

Average Molecular Weight

212.3285

Monoisotopic Molecular Weight

212.177630012

IUPAC Name

4-(3-hydroxybutyl)-3,3,5-trimethylcyclohexan-1-one

Traditional Name

4-(3-hydroxybutyl)-3,3,5-trimethylcyclohexan-1-one

CAS Registry Number

128660-70-8

SMILES

CC(O)CCC1C(C)CC(=O)CC1(C)C

InChI Identifier

InChI=1S/C13H24O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h9-10,12,14H,5-8H2,1-4H3

InChI Key

QIHMBTNCJUFMCE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Megastigmane sesquiterpenoid
Sesquiterpenoid
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039805)

Source

Endogenous

Endogenous (HMDB: HMDB0039805)

Animal

Animal (HMDB: HMDB0039805)

Exogenous

Food

Food (HMDB: HMDB0039805)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0039805)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0039805)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0039805)

Lipid metabolism pathway (HMDB: HMDB0039805)

Cellular process

Cell signaling (HMDB: HMDB0039805)

Biochemical process

Lipid transport (HMDB: HMDB0039805)

Role

Biological role

Energy source (HMDB: HMDB0039805)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039805)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	2.65	ALOGPS
logP	2.52	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	17.61	ChemAxon
pKa (Strongest Basic)	-1.7	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	61.92 m³·mol⁻¹	ChemAxon
Polarizability	25.45 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]+	150.422	31661259
DarkChem	[M-H]-	148.031	31661259
DeepCCS	[M+H]+	156.57	30932474
DeepCCS	[M-H]-	154.212	30932474
DeepCCS	[M-2H]-	188.62	30932474
DeepCCS	[M+Na]+	163.22	30932474
AllCCS	[M+H]+	151.7	32859911
AllCCS	[M+H-H2O]+	147.9	32859911
AllCCS	[M+NH4]+	155.2	32859911
AllCCS	[M+Na]+	156.2	32859911
AllCCS	[M-H]-	156.7	32859911
AllCCS	[M+Na-2H]-	157.8	32859911
AllCCS	[M+HCOO]-	159.1	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.	5.15 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9979 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.48 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2226.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	397.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	180.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	575.3 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	637.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	68.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1043.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	416.1 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	1311.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	283.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	408.6 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	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone	CC(O)CCC1C(C)CC(=O)CC1(C)C	2417.6	Standard polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone	CC(O)CCC1C(C)CC(=O)CC1(C)C	1564.2	Standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone	CC(O)CCC1C(C)CC(=O)CC1(C)C	1637.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TMS,isomer #1	CC(CCC1C(C)CC(=O)CC1(C)C)O[Si](C)(C)C	1746.9	Semi standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TMS,isomer #2	CC(O)CCC1C(C)CC(O[Si](C)(C)C)=CC1(C)C	1764.6	Semi standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TMS,isomer #3	CC(O)CCC1C(C)C=C(O[Si](C)(C)C)CC1(C)C	1781.5	Semi standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TMS,isomer #1	CC(CCC1C(C)CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	1774.2	Semi standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TMS,isomer #1	CC(CCC1C(C)CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	1833.1	Standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TMS,isomer #2	CC(CCC1C(C)C=C(O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C	1794.7	Semi standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TMS,isomer #2	CC(CCC1C(C)C=C(O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C	1828.8	Standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TBDMS,isomer #1	CC(CCC1C(C)CC(=O)CC1(C)C)O[Si](C)(C)C(C)(C)C	1996.7	Semi standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TBDMS,isomer #2	CC(O)CCC1C(C)CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	1992.9	Semi standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TBDMS,isomer #3	CC(O)CCC1C(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)C	2011.4	Semi standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TBDMS,isomer #1	CC(CCC1C(C)CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2231.9	Semi standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TBDMS,isomer #1	CC(CCC1C(C)CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2267.7	Standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TBDMS,isomer #2	CC(CCC1C(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C	2254.2	Semi standard non polar	33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TBDMS,isomer #2	CC(CCC1C(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C	2260.9	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-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ke-6900000000-1ed170c5f1f756ff297f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone GC-MS (1 TMS) - 70eV, Positive	splash10-00ri-9430000000-7d31754c4accaf7ad0e4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 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 - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 10V, Positive-QTOF	splash10-0002-0920000000-d99ac261f26bfe1928ff	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 20V, Positive-QTOF	splash10-0002-3910000000-44347819cf2d3d8f4a6c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 40V, Positive-QTOF	splash10-0lxw-6900000000-7d683bd90b4689370e0a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 10V, Negative-QTOF	splash10-03di-0390000000-32de0f0c4a5d36cbd57a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 20V, Negative-QTOF	splash10-03dl-1890000000-d92ba42ef3e1cb4cf57b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 40V, Negative-QTOF	splash10-0k97-5900000000-eb495a9bcb06b23d1be8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 10V, Positive-QTOF	splash10-03fs-1930000000-6d95eb7a6fcc448a944c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 20V, Positive-QTOF	splash10-0a7i-6900000000-d00671822d95f97c0e1a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 40V, Positive-QTOF	splash10-0a4i-9500000000-0101eb1c6f0b6bb8863f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 10V, Negative-QTOF	splash10-03di-0290000000-766f2cf6532b8686b2eb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 20V, Negative-QTOF	splash10-03xr-0960000000-f7262a9568581bd42769	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 40V, Negative-QTOF	splash10-03xu-1910000000-6d9037c703ed9bcd1c7f	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB019455

KNApSAcK ID

Not Available

Chemspider ID

35014878

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752728

PDB ID

Not Available

ChEBI ID

168208

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone (HMDB0039805)

MOL for HMDB0039805 (4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone)

3D MOL for HMDB0039805 (4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone)

3D SDF for HMDB0039805 (4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone)

3D-SDF for HMDB0039805 (4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone)

PDB for HMDB0039805 (4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone)

3D PDB for HMDB0039805 (4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone)

SMILES for HMDB0039805 (4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone)

INCHI for HMDB0039805 (4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone)

Structure for HMDB0039805 (4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone)

3D Structure for HMDB0039805 (4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra