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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:54:49 UTC

Update Date

2023-02-21 17:24:31 UTC

HMDB ID

HMDB0034979

Secondary Accession Numbers

HMDB34979

Metabolite Identification

Common Name

gamma-Ionone

Description

gamma-Ionone, also known as g-ionon, 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 gamma-Ionone.

Structure

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

HMDB0034979
     RDKit          3D
gamma-Ionone
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.1687   -1.0558    2.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0733   -0.9595    1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7882   -1.9370    0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6459   -1.1988   -0.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7542   -0.3234   -1.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150    0.7026   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9089    1.8368   -0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    1.3212   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758    0.0929    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654   -0.4032    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779    0.1686    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043   -0.2742    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6839    0.4022    0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6520   -1.2264   -0.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -1.8201    3.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202   -0.3072    3.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921   -2.5755    1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030   -2.5914   -0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4309   -0.5950   -0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1463   -1.9199   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058   -0.9551   -1.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437    0.2287   -2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4957    2.1750    0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9475    1.5024    0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8389    2.6938   -0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839    1.3565   -2.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9658    0.7308   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913    2.3871   -1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447    0.9128    1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2067   -1.2219   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    1.0063    1.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6191    0.2035    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576    0.1367    1.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4664    1.5064    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  9  2  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
M  END


  Mrv0541 05061308102D          

 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  2  0  0  0  0
  9  5  1  0  0  0  0
 10  1  2  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  1  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>
HMDB0034979

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)\C=C\C1C(=C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8,12H,1,5-6,9H2,2-4H3/b8-7+

> <INCHI_KEY>
SFEOKXHPFMOVRM-BQYQJAHWSA-N

> <FORMULA>
C13H20O

> <MOLECULAR_WEIGHT>
192.2973

> <EXACT_MASS>
192.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.24923939676373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-(2,2-dimethyl-6-methylidenecyclohexyl)but-3-en-2-one

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
3.3772151653333338

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.830426238446186

> <JCHEM_PKA_STRONGEST_BASIC>
-4.904312226510013

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
61.0162

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ionone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034979
     RDKit          3D
gamma-Ionone
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.1687   -1.0558    2.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0733   -0.9595    1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7882   -1.9370    0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6459   -1.1988   -0.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7542   -0.3234   -1.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150    0.7026   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9089    1.8368   -0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    1.3212   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758    0.0929    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654   -0.4032    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779    0.1686    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043   -0.2742    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6839    0.4022    0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6520   -1.2264   -0.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -1.8201    3.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202   -0.3072    3.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921   -2.5755    1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030   -2.5914   -0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4309   -0.5950   -0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1463   -1.9199   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058   -0.9551   -1.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437    0.2287   -2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4957    2.1750    0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9475    1.5024    0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8389    2.6938   -0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839    1.3565   -2.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9658    0.7308   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913    2.3871   -1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447    0.9128    1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2067   -1.2219   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    1.0063    1.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6191    0.2035    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576    0.1367    1.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4664    1.5064    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  9  2  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  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    HMDB0034979
HETATM    1  C1  UNL     1      -1.169  -1.056   2.592  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.073  -0.960   1.269  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.788  -1.937   0.435  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.646  -1.199  -0.558  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.754  -0.323  -1.390  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.015   0.703  -0.577  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.909   1.837  -0.120  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.037   1.321  -1.487  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.276   0.093   0.593  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.065  -0.403   0.187  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.178   0.169   0.659  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.504  -0.274   0.297  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.684   0.402   0.856  1.00  0.00           C  
HETATM   14  O1  UNL     1       3.652  -1.226  -0.487  1.00  0.00           O  
HETATM   15  H1  UNL     1      -1.748  -1.820   3.066  1.00  0.00           H  
HETATM   16  H2  UNL     1      -0.620  -0.307   3.174  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.492  -2.576   1.041  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.103  -2.591  -0.133  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.431  -0.595  -0.059  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.146  -1.920  -1.216  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.006  -0.955  -1.905  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.344   0.229  -2.152  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.496   2.175   0.862  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.948   1.502   0.066  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.839   2.694  -0.804  1.00  0.00           H  
HETATM   26  H12 UNL     1      -0.384   1.357  -2.531  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.966   0.731  -1.503  1.00  0.00           H  
HETATM   28  H14 UNL     1       0.191   2.387  -1.209  1.00  0.00           H  
HETATM   29  H15 UNL     1      -0.145   0.913   1.333  1.00  0.00           H  
HETATM   30  H16 UNL     1       1.207  -1.222  -0.487  1.00  0.00           H  
HETATM   31  H17 UNL     1       2.002   1.006   1.348  1.00  0.00           H  
HETATM   32  H18 UNL     1       5.619   0.204   0.289  1.00  0.00           H  
HETATM   33  H19 UNL     1       4.758   0.137   1.924  1.00  0.00           H  
HETATM   34  H20 UNL     1       4.466   1.506   0.838  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3    9
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7    8    9
CONECT    7   23   24   25
CONECT    8   26   27   28
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12   31
CONECT   12   13   14   14
CONECT   13   32   33   34
END

HMDB0034979
     RDKit          3D
gamma-Ionone
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.1687   -1.0558    2.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0733   -0.9595    1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7882   -1.9370    0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6459   -1.1988   -0.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7542   -0.3234   -1.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150    0.7026   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9089    1.8368   -0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373    1.3212   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758    0.0929    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654   -0.4032    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779    0.1686    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043   -0.2742    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6839    0.4022    0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6520   -1.2264   -0.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -1.8201    3.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6202   -0.3072    3.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921   -2.5755    1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030   -2.5914   -0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4309   -0.5950   -0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1463   -1.9199   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058   -0.9551   -1.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437    0.2287   -2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4957    2.1750    0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9475    1.5024    0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8389    2.6938   -0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839    1.3565   -2.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9658    0.7308   -1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913    2.3871   -1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447    0.9128    1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2067   -1.2219   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    1.0063    1.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6191    0.2035    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576    0.1367    1.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4664    1.5064    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  9  2  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3E)-4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one	ChEBI
gamma-Ionon	ChEBI
g-Ionon	Generator
Γ-ionon	Generator
g-Ionone	Generator
Γ-ionone	Generator
(3E)-4-(2,2-Dimethyl-6-methylidenecyclohexyl)but-3-en-2-one	HMDB
4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one	HMDB
4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one, 9ci	HMDB
4-(2-Methylene-6,6-dimethylcyclohexyl)-3-buten-2-one	HMDB
FEMA 3175	HMDB
gamma-Lonone	HMDB
laquo gammaraquo -Ionone	HMDB

Chemical Formula

C₁₃H₂₀O

Average Molecular Weight

192.2973

Monoisotopic Molecular Weight

192.151415262

IUPAC Name

(3E)-4-(2,2-dimethyl-6-methylidenecyclohexyl)but-3-en-2-one

Traditional Name

ionone

CAS Registry Number

79-76-5

SMILES

CC(=O)\C=C\C1C(=C)CCCC1(C)C

InChI Identifier

InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8,12H,1,5-6,9H2,2-4H3/b8-7+

InChI Key

SFEOKXHPFMOVRM-BQYQJAHWSA-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

Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
Ionone derivative
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

ionone (CHEBI:49250 )

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034979)

Source

Endogenous

Endogenous (HMDB: HMDB0034979)

Plant

Plant (HMDB: HMDB0034979)

Animal

Animal (HMDB: HMDB0034979)

Exogenous

Food

Food (HMDB: HMDB0034979)

Fruit

Tropical fruit

Tamarind (FooDB: FOOD00180)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034979)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034979)

Cellular process

Cell signaling (HMDB: HMDB0034979)

Biochemical process

Lipid transport (HMDB: HMDB0034979)

Role

Biological role

Energy storage (HMDB: HMDB0034979)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034979)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	267.00 to 268.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	8.83 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.505 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0096 g/L	ALOGPS
logP	3.99	ALOGPS
logP	3.38	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	19.83	ChemAxon
pKa (Strongest Basic)	-4.9	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	2	ChemAxon
Refractivity	61.02 m³·mol⁻¹	ChemAxon
Polarizability	23.25 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
DeepCCS	[M+H]+	150.907	30932474
DeepCCS	[M-H]-	148.544	30932474
DeepCCS	[M-2H]-	182.72	30932474
DeepCCS	[M+Na]+	157.434	30932474
AllCCS	[M+H]+	144.2	32859911
AllCCS	[M+H-H2O]+	140.1	32859911
AllCCS	[M+NH4]+	147.9	32859911
AllCCS	[M+Na]+	149.0	32859911
AllCCS	[M-H]-	150.1	32859911
AllCCS	[M+Na-2H]-	151.1	32859911
AllCCS	[M+HCOO]-	152.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Ionone	CC(=O)\C=C\C1C(=C)CCCC1(C)C	1883.7	Standard polar	33892256
gamma-Ionone	CC(=O)\C=C\C1C(=C)CCCC1(C)C	1410.1	Standard non polar	33892256
gamma-Ionone	CC(=O)\C=C\C1C(=C)CCCC1(C)C	1409.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Ionone,1TMS,isomer #1	C=C(/C=C/C1C(=C)CCCC1(C)C)O[Si](C)(C)C	1590.7	Semi standard non polar	33892256
gamma-Ionone,1TMS,isomer #1	C=C(/C=C/C1C(=C)CCCC1(C)C)O[Si](C)(C)C	1612.3	Standard non polar	33892256
gamma-Ionone,1TBDMS,isomer #1	C=C(/C=C/C1C(=C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1838.0	Semi standard non polar	33892256
gamma-Ionone,1TBDMS,isomer #1	C=C(/C=C/C1C(=C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1847.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Ionone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ba-4900000000-f9aafc2b2b7c434052c5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Ionone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Ionone 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 - gamma-Ionone 10V, Positive-QTOF	splash10-002f-0900000000-222c25bb3e7a42ab1321	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 20V, Positive-QTOF	splash10-004u-3900000000-e1117004acdbca234f89	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 40V, Positive-QTOF	splash10-014i-9400000000-3afe7c89edcfe4b080b1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 10V, Negative-QTOF	splash10-0006-0900000000-099fc3506ab6ef6a84d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 20V, Negative-QTOF	splash10-0006-0900000000-2c62147e95b324ad1bbb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 40V, Negative-QTOF	splash10-05ed-2900000000-43f9c40d0da2463f54e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 10V, Positive-QTOF	splash10-006x-0900000000-f7be24804814148e43a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 20V, Positive-QTOF	splash10-05fu-8900000000-719975180f85f30cd26c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 40V, Positive-QTOF	splash10-052f-9500000000-b246cc8c2e31e4ef8371	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 10V, Negative-QTOF	splash10-0006-0900000000-14436e4d9ff8d032db54	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 20V, Negative-QTOF	splash10-00di-0900000000-8ba0b873872011e97fa4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Ionone 40V, Negative-QTOF	splash10-00dj-3900000000-01234d354968b8246a21	2021-09-22	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

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

FDB013578

KNApSAcK ID

Not Available

Chemspider ID

4516050

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5363741

PDB ID

Not Available

ChEBI ID

49250

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035361

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 gamma-Ionone (HMDB0034979)

MOL for HMDB0034979 (gamma-Ionone)

3D MOL for HMDB0034979 (gamma-Ionone)

3D SDF for HMDB0034979 (gamma-Ionone)

3D-SDF for HMDB0034979 (gamma-Ionone)

PDB for HMDB0034979 (gamma-Ionone)

3D PDB for HMDB0034979 (gamma-Ionone)

SMILES for HMDB0034979 (gamma-Ionone)

INCHI for HMDB0034979 (gamma-Ionone)

Structure for HMDB0034979 (gamma-Ionone)

3D Structure for HMDB0034979 (gamma-Ionone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra