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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:52:38 UTC

Update Date

2023-02-21 17:22:44 UTC

HMDB ID

HMDB0032913

Secondary Accession Numbers

HMDB32913

Metabolite Identification

Common Name

4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone

Description

4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone, also known as 7,8-dihydro-beta-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone.

Structure

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

HMDB0032913
     RDKit          3D
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.0337    0.2188    0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4769   -0.6340   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -1.2265   -1.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9855   -0.7656   -0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2327    0.1019    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473    0.0089    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8148   -0.5338    1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412   -0.9747    2.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771   -0.7153    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    0.1717    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4899   -0.1375   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0834    0.4854   -0.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749    2.0073   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6141    0.1486   -2.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707    0.6905    0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3267    0.9945    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -0.4189    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7708   -0.5020   -1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900   -1.8626   -0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6224   -0.0274    1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5256    1.1914    0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4973   -0.1240    2.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761   -1.7052    2.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647   -1.5217    3.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6054   -0.5444    2.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5460   -1.7724    1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193   -0.0576    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    1.2133    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975    0.1776   -1.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053   -1.2416   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658    2.4973   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690    2.3973    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337    2.2783   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900   -0.9218   -2.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706    0.8112   -2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    0.2931   -3.0233 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  1  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  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END


  Mrv0541 05061306472D          

 14 14  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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.0000    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
    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
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032913

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CCC1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H22O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h5-9H2,1-4H3

> <INCHI_KEY>
QJJDNZGPQDGNDX-UHFFFAOYSA-N

> <FORMULA>
C13H22O

> <MOLECULAR_WEIGHT>
194.3132

> <EXACT_MASS>
194.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.909387963182372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-one

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
3.2778001806666675

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.59519115238362

> <JCHEM_PKA_STRONGEST_BASIC>
-7.278058155693596

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
60.7288

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydro-β-ionone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032913
     RDKit          3D
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.0337    0.2188    0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4769   -0.6340   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -1.2265   -1.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9855   -0.7656   -0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2327    0.1019    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473    0.0089    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8148   -0.5338    1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412   -0.9747    2.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771   -0.7153    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    0.1717    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4899   -0.1375   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0834    0.4854   -0.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749    2.0073   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6141    0.1486   -2.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707    0.6905    0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3267    0.9945    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -0.4189    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7708   -0.5020   -1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900   -1.8626   -0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6224   -0.0274    1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5256    1.1914    0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4973   -0.1240    2.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761   -1.7052    2.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647   -1.5217    3.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6054   -0.5444    2.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5460   -1.7724    1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193   -0.0576    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    1.2133    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975    0.1776   -1.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053   -1.2416   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658    2.4973   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690    2.3973    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337    2.2783   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900   -0.9218   -2.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706    0.8112   -2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    0.2931   -3.0233 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  1  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  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   4.620   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
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9    5   13                                                       
CONECT   10    1    6   12                                                  
CONECT   11    2    7   14                                                  
CONECT   12    8   10   13                                                  
CONECT   13    3    4    9   12                                             
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0032913
HETATM    1  C1  UNL     1       4.034   0.219   0.534  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.477  -0.634  -0.530  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.252  -1.227  -1.258  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.986  -0.766  -0.706  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.233   0.102   0.227  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.247   0.009   0.159  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.815  -0.534   1.276  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.041  -0.975   2.428  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.277  -0.715   1.433  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.055   0.172   0.469  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.490  -0.137  -0.880  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.083   0.485  -0.954  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.275   2.007  -0.881  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.614   0.149  -2.342  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.971   0.690   0.112  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.327   0.994   0.860  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.375  -0.419   1.405  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.771  -0.502  -1.742  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.790  -1.863  -0.548  1.00  0.00           H  
HETATM   20  H6  UNL     1       1.622  -0.027   1.273  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.526   1.191   0.024  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.497  -0.124   2.960  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.776  -1.705   2.030  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.565  -1.522   3.176  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.605  -0.544   2.478  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.546  -1.772   1.158  1.00  0.00           H  
HETATM   27  H13 UNL     1      -4.119  -0.058   0.578  1.00  0.00           H  
HETATM   28  H14 UNL     1      -2.869   1.213   0.806  1.00  0.00           H  
HETATM   29  H15 UNL     1      -3.098   0.178  -1.721  1.00  0.00           H  
HETATM   30  H16 UNL     1      -2.305  -1.242  -0.923  1.00  0.00           H  
HETATM   31  H17 UNL     1      -0.666   2.497  -1.665  1.00  0.00           H  
HETATM   32  H18 UNL     1      -0.969   2.397   0.107  1.00  0.00           H  
HETATM   33  H19 UNL     1      -2.334   2.278  -1.122  1.00  0.00           H  
HETATM   34  H20 UNL     1      -0.390  -0.922  -2.456  1.00  0.00           H  
HETATM   35  H21 UNL     1       0.171   0.811  -2.743  1.00  0.00           H  
HETATM   36  H22 UNL     1      -1.525   0.293  -3.023  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3    4
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    8   22   23   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   14
CONECT   13   31   32   33
CONECT   14   34   35   36
END

HMDB0032913
     RDKit          3D
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.0337    0.2188    0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4769   -0.6340   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -1.2265   -1.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9855   -0.7656   -0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2327    0.1019    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473    0.0089    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8148   -0.5338    1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412   -0.9747    2.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771   -0.7153    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    0.1717    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4899   -0.1375   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0834    0.4854   -0.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749    2.0073   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6141    0.1486   -2.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707    0.6905    0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3267    0.9945    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -0.4189    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7708   -0.5020   -1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900   -1.8626   -0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6224   -0.0274    1.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5256    1.1914    0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4973   -0.1240    2.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761   -1.7052    2.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647   -1.5217    3.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6054   -0.5444    2.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5460   -1.7724    1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193   -0.0576    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    1.2133    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975    0.1776   -1.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053   -1.2416   -0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658    2.4973   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690    2.3973    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337    2.2783   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900   -0.9218   -2.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706    0.8112   -2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    0.2931   -3.0233 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  1  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  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7,8-Dihydro-beta-ionone	ChEBI
Dihydro-beta-ionone	ChEBI
7,8-Dihydro-b-ionone	Generator
7,8-Dihydro-β-ionone	Generator
Dihydro-b-ionone	Generator
Dihydro-β-ionone	Generator
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone, 9ci	HMDB
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)butan-2-one	HMDB
4-(2,6,6-Trimethyl-1-cyclohexenyl)-2-butanone	HMDB
4-(2,6,6-Trimethylcyclohex-1-en-1-yl)butan-2-one	HMDB
5-Megastigmen-9-one	HMDB
7,8-dehydro-beta-Ionone	HMDB
alpha,beta-dihydro-beta-Ionone	HMDB
Oxidized latia luciferin	HMDB
Oxidized-latia-luciferin	HMDB

Chemical Formula

C₁₃H₂₂O

Average Molecular Weight

194.3132

Monoisotopic Molecular Weight

194.167065326

IUPAC Name

4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-one

Traditional Name

dihydro-β-ionone

CAS Registry Number

17283-81-7

SMILES

CC(=O)CCC1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C13H22O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h5-9H2,1-4H3

InChI Key

QJJDNZGPQDGNDX-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
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

methyl ketone (CHEBI:18015 )
Latia luciferin (CHEBI:18015 )
a luciferin (OXIDIZED-LATIA-LUCIFERIN )

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032913)

Source

Endogenous

Endogenous (HMDB: HMDB0032913)

Plant

Plant (HMDB: HMDB0032913)

Animal

Animal (HMDB: HMDB0032913)

Exogenous

Food

Food (HMDB: HMDB0032913)

Fruit

Berry

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0032913)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032913)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032913)

Lipid metabolism pathway (HMDB: HMDB0032913)

Cellular process

Cell signaling (HMDB: HMDB0032913)

Biochemical process

Lipid transport (HMDB: HMDB0032913)

Role

Biological role

Energy source (HMDB: HMDB0032913)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032913)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	261.00 to 262.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	48 mg/L @ 20 °C (exp)	The Good Scents Company Information System
LogP	3.990 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.86	ALOGPS
logP	3.28	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	19.6	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.73 m³·mol⁻¹	ChemAxon
Polarizability	23.91 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]+	146.214	31661259
DarkChem	[M-H]-	142.726	31661259
DeepCCS	[M+H]+	152.435	30932474
DeepCCS	[M-H]-	150.032	30932474
DeepCCS	[M-2H]-	185.372	30932474
DeepCCS	[M+Na]+	159.972	30932474
AllCCS	[M+H]+	146.0	32859911
AllCCS	[M+H-H2O]+	142.1	32859911
AllCCS	[M+NH4]+	149.7	32859911
AllCCS	[M+Na]+	150.8	32859911
AllCCS	[M-H]-	152.4	32859911
AllCCS	[M+Na-2H]-	153.5	32859911
AllCCS	[M+HCOO]-	154.8	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.	7.4 minutes	32390414
Predicted by Siyang on May 30, 2022	19.5371 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.44 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2469.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	684.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	249.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	402.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	355.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	773.7 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	832.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	102.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1599.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	502.6 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	1571.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	582.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	441.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	495.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	674.4 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone	CC(=O)CCC1=C(C)CCCC1(C)C	1756.3	Standard polar	33892256
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone	CC(=O)CCC1=C(C)CCCC1(C)C	1390.8	Standard non polar	33892256
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone	CC(=O)CCC1=C(C)CCCC1(C)C	1445.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone,1TMS,isomer #1	CC(=CCC1=C(C)CCCC1(C)C)O[Si](C)(C)C	1609.1	Semi standard non polar	33892256
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone,1TMS,isomer #1	CC(=CCC1=C(C)CCCC1(C)C)O[Si](C)(C)C	1581.4	Standard non polar	33892256
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone,1TMS,isomer #2	C=C(CCC1=C(C)CCCC1(C)C)O[Si](C)(C)C	1585.2	Semi standard non polar	33892256
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone,1TMS,isomer #2	C=C(CCC1=C(C)CCCC1(C)C)O[Si](C)(C)C	1612.1	Standard non polar	33892256
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone,1TBDMS,isomer #1	CC(=CCC1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1851.5	Semi standard non polar	33892256
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone,1TBDMS,isomer #1	CC(=CCC1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1809.7	Standard non polar	33892256
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone,1TBDMS,isomer #2	C=C(CCC1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1833.7	Semi standard non polar	33892256
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone,1TBDMS,isomer #2	C=C(CCC1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1816.1	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-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f96-5900000000-426d07033f81ec504148	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-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 - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 10V, Positive-QTOF	splash10-002b-1900000000-ffcdf81995ea9c0023f2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 20V, Positive-QTOF	splash10-00p1-5900000000-3c9601b171b3605b7cc4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 40V, Positive-QTOF	splash10-0ldl-9400000000-4255fb596f7378e3c7d1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 10V, Negative-QTOF	splash10-0006-0900000000-656a64489e25605f3a12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 20V, Negative-QTOF	splash10-0006-2900000000-264de3181ce7b4fd99d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 40V, Negative-QTOF	splash10-0a4i-9500000000-65cea0c82072bbc70d2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 10V, Negative-QTOF	splash10-0006-0900000000-f4ac9f2710ef63610b81	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 20V, Negative-QTOF	splash10-0fk9-0900000000-48de34554de0356e0d73	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 40V, Negative-QTOF	splash10-0595-5900000000-5e6f1faa2f2f94e74dfb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 10V, Positive-QTOF	splash10-000i-1900000000-df1e27a7ad978e5bb657	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 20V, Positive-QTOF	splash10-00di-7900000000-8fbc426a01b29c3986b9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone 40V, Positive-QTOF	splash10-05mo-9300000000-156f9327780578e5a4f1	2021-09-24	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]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details

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

OXIDIZED-LATIA-LUCIFERIN

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

519382

PDB ID

Not Available

ChEBI ID

18015

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1019322

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-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone (HMDB0032913)

MOL for HMDB0032913 (4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone)

3D MOL for HMDB0032913 (4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone)

3D SDF for HMDB0032913 (4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone)

3D-SDF for HMDB0032913 (4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone)

PDB for HMDB0032913 (4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone)

3D PDB for HMDB0032913 (4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone)

SMILES for HMDB0032913 (4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone)

INCHI for HMDB0032913 (4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone)

Structure for HMDB0032913 (4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone)

3D Structure for HMDB0032913 (4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-butanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra