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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-03-07 21:34:48 UTC

Update Date

2022-03-07 03:17:37 UTC

HMDB ID

HMDB0059883

Secondary Accession Numbers

HMDB59883

Metabolite Identification

Common Name

alpha-Ionone

Description

alpha-Ionone, also known as (e)-alpha-ionone or trans-a-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-Ionone is a potentially toxic compound. Alpha-ionone is a neutral compound. Alpha-ionone has a dry, floral, and flower taste with a cedar wood-like scent. It is a naturally occurring organic compound found in a variety of essential oils, including rose oil, flowers from Boronia megastigma (brown boronia; doi: 10.21273/hortsci.30.4.876d) and coml oil. Alpha-ionone is found in highest concentrations in corns, tea, and carrots and in lower concentrations in hyssops, peppermints, and safflowers. Alpha-ionone has also been detected in common grapes, sour cherries, common wheats, garden tomato, and wakames making beta-ionone a potential biomarker for the consumption of these foods. Alpha-ionone is used as to make Vitamins A, E and K1. It is used as a fragrance in perfumes, cosmetics and personal care products, and household cleaners and detergents. Alpha-ionone is used as a food flavoring in beverages, ice cream, baked goods and candies.

Structure

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

HMDB0059883
     RDKit          3D
alpha-Ionone
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.9890    0.3509   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4498   -0.3306    0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -0.7384    1.7831 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0278   -0.5357    1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401   -0.1371    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196   -0.3563    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514   -1.3757   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567   -2.4401   -1.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1029   -1.3479   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247   -0.3106   -0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5429    0.5144    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936    0.9276    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9974    1.7154   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363    1.7587    1.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895    0.1402   -0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    0.0193   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8383    1.4537   -0.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228   -1.0400    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    0.3668   -0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -0.7997    1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232   -3.4622   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124   -2.3981   -2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537   -2.3688   -0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254   -2.0986   -1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680   -0.8212   -0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    0.3631   -1.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929    1.3920    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -0.1052    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9783    2.2387   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    1.1107   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262    2.5001   -0.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6176    1.2041    2.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    2.7623    1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    1.8481    1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  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
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END

  Mrv1652305271900022D          

 14 14  0  0  0  0            999 V2000
   -1.3259   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0404   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0404   -3.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3259   -3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6114   -3.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6114   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5320   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2465   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5320   -1.2964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394   -1.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134   -1.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1031   -3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  5 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059883

> <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/h6-8,12H,5,9H2,1-4H3/b8-7+

> <INCHI_KEY>
UZFLPKAIBPNNCA-BQYQJAHWSA-N

> <FORMULA>
C13H20O

> <MOLECULAR_WEIGHT>
192.2973

> <EXACT_MASS>
192.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.077753565120858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
3.3192814949999994

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.830428760239922

> <JCHEM_PKA_STRONGEST_BASIC>
-4.904326214789516

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
62.088699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-ionone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0059883
     RDKit          3D
alpha-Ionone
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.9890    0.3509   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4498   -0.3306    0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -0.7384    1.7831 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0278   -0.5357    1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401   -0.1371    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196   -0.3563    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514   -1.3757   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567   -2.4401   -1.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1029   -1.3479   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247   -0.3106   -0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5429    0.5144    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936    0.9276    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9974    1.7154   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363    1.7587    1.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895    0.1402   -0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    0.0193   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8383    1.4537   -0.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228   -1.0400    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    0.3668   -0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -0.7997    1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232   -3.4622   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124   -2.3981   -2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537   -2.3688   -0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254   -2.0986   -1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680   -0.8212   -0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    0.3631   -1.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929    1.3920    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -0.1052    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9783    2.2387   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    1.1107   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262    2.5001   -0.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6176    1.2041    2.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    2.7623    1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    1.8481    1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  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
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.475  -3.960   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.809  -4.730   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.809  -6.270   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.475  -7.040   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.141  -6.270   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.141  -4.730   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.192  -3.960   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.526  -4.730   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.860  -3.960   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.193  -4.730   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.860  -2.420   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.874  -2.472   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.705  -2.626   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.192  -7.040   0.000  0.00  0.00           C+0
CONECT    1    2    6   12   13                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    5                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0059883
HETATM    1  C1  UNL     1       3.989   0.351  -0.304  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.450  -0.331   0.890  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.228  -0.738   1.783  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.028  -0.536   1.044  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.140  -0.137   0.150  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.320  -0.356   0.324  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.851  -1.376  -0.601  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.057  -2.440  -1.106  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.103  -1.348  -0.975  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.025  -0.311  -0.494  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.543   0.514   0.647  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.094   0.928   0.347  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.997   1.715  -0.920  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.536   1.759   1.488  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.090   0.140  -0.377  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.513   0.019  -1.251  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.838   1.454  -0.139  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.623  -1.040   1.926  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.515   0.367  -0.737  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.450  -0.800   1.358  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.323  -3.462  -0.881  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.212  -2.398  -2.196  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.054  -2.369  -0.625  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.525  -2.099  -1.665  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.968  -0.821  -0.189  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.221   0.363  -1.382  1.00  0.00           H  
HETATM   27  H13 UNL     1      -3.193   1.392   0.750  1.00  0.00           H  
HETATM   28  H14 UNL     1      -2.509  -0.105   1.559  1.00  0.00           H  
HETATM   29  H15 UNL     1      -1.978   2.239  -1.063  1.00  0.00           H  
HETATM   30  H16 UNL     1      -0.817   1.111  -1.822  1.00  0.00           H  
HETATM   31  H17 UNL     1      -0.226   2.500  -0.833  1.00  0.00           H  
HETATM   32  H18 UNL     1      -0.618   1.204   2.459  1.00  0.00           H  
HETATM   33  H19 UNL     1      -1.000   2.762   1.547  1.00  0.00           H  
HETATM   34  H20 UNL     1       0.562   1.848   1.288  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3    4
CONECT    4    5    5   18
CONECT    5    6   19
CONECT    6    7   12   20
CONECT    7    8    9    9
CONECT    8   21   22   23
CONECT    9   10   24
CONECT   10   11   25   26
CONECT   11   12   27   28
CONECT   12   13   14
CONECT   13   29   30   31
CONECT   14   32   33   34
END

HMDB0059883
     RDKit          3D
alpha-Ionone
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.9890    0.3509   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4498   -0.3306    0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -0.7384    1.7831 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0278   -0.5357    1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401   -0.1371    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196   -0.3563    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514   -1.3757   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567   -2.4401   -1.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1029   -1.3479   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247   -0.3106   -0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5429    0.5144    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936    0.9276    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9974    1.7154   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363    1.7587    1.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895    0.1402   -0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    0.0193   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8383    1.4537   -0.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228   -1.0400    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    0.3668   -0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -0.7997    1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232   -3.4622   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124   -2.3981   -2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537   -2.3688   -0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254   -2.0986   -1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680   -0.8212   -0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    0.3631   -1.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929    1.3920    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -0.1052    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9783    2.2387   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    1.1107   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262    2.5001   -0.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6176    1.2041    2.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    2.7623    1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    1.8481    1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  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
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-alpha-Ionone	ChEBI
alpha-(e)-Ionone	ChEBI
alpha-Cyclocitrylideneacetone	ChEBI
alpha-Ionon	ChEBI
trans-alpha-Ionone	ChEBI
(e)-a-Ionone	Generator
(e)-Α-ionone	Generator
a-(e)-Ionone	Generator
Α-(e)-ionone	Generator
a-Cyclocitrylideneacetone	Generator
Α-cyclocitrylideneacetone	Generator
a-Ionon	Generator
Α-ionon	Generator
trans-a-Ionone	Generator
trans-Α-ionone	Generator
a-Ionone	Generator
Α-ionone	Generator
(3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-ON	HMDB
alpha-Ionone, (e)-isomer	MeSH
alpha-Ionone, (e)-(+-)-isomer	MeSH
alpha-Ionone, (+)-iosmer	MeSH

Chemical Formula

C₁₃H₂₀O

Average Molecular Weight

192.2973

Monoisotopic Molecular Weight

192.151415262

IUPAC Name

(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one

Traditional Name

α-ionone

CAS Registry Number

Not Available

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/h6-8,12H,5,9H2,1-4H3/b8-7+

InChI Key

UZFLPKAIBPNNCA-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

enone (CHEBI:32319 )
methyl ketone (CHEBI:32319 )
ionone (CHEBI:32319 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 20809147)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0059883)

Source

Endogenous

Endogenous (HMDB: HMDB0059883)

Animal

Animal (HMDB: HMDB0059883)

Exogenous

Food

Food (HMDB: HMDB0059883)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Flat bread

Tortilla (FooDB: FOOD00709)

Tea

Exogenous (HMDB: HMDB0059883)

Synthetic

Personal care products

Perfume (HMDB: HMDB0059883)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0059883)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0059883)

Lipid metabolism pathway (HMDB: HMDB0059883)

Cellular process

Cell signaling (HMDB: HMDB0059883)

Biochemical process

Lipid transport (HMDB: HMDB0059883)

Role

Biological role

Energy source (HMDB: HMDB0059883)
Allergen (HMDB: HMDB0059883)
Cytochrome-P450-1A inducer (HMDB: HMDB0059883)
Cytochrome-P450-2B inducer (HMDB: HMDB0059883)
Tremorigenic (HMDB: HMDB0059883)

Industrial application

Food and nutrition

Food and nutrition (HMDB: HMDB0059883)

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	0.05 g/L	ALOGPS
logP	4.14	ALOGPS
logP	3.32	ChemAxon
logS	-3.6	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	62.09 m³·mol⁻¹	ChemAxon
Polarizability	23.08 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]+	148.697	30932474
DeepCCS	[M-H]-	146.301	30932474
DeepCCS	[M-2H]-	180.482	30932474
DeepCCS	[M+Na]+	155.102	30932474
AllCCS	[M+H]+	143.0	32859911
AllCCS	[M+H-H2O]+	138.9	32859911
AllCCS	[M+NH4]+	146.8	32859911
AllCCS	[M+Na]+	147.9	32859911
AllCCS	[M-H]-	149.7	32859911
AllCCS	[M+Na-2H]-	150.7	32859911
AllCCS	[M+HCOO]-	151.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Ionone	CC(=O)\C=C\C1C(C)=CCCC1(C)C	1841.1	Standard polar	33892256
alpha-Ionone	CC(=O)\C=C\C1C(C)=CCCC1(C)C	1402.6	Standard non polar	33892256
alpha-Ionone	CC(=O)\C=C\C1C(C)=CCCC1(C)C	1426.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-Ionone,1TMS,isomer #1	C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C	1603.3	Semi standard non polar	33892256
alpha-Ionone,1TMS,isomer #1	C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C	1627.6	Standard non polar	33892256
alpha-Ionone,1TMS,isomer #1	C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C	1744.1	Standard polar	33892256
alpha-Ionone,1TBDMS,isomer #1	C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1839.7	Semi standard non polar	33892256
alpha-Ionone,1TBDMS,isomer #1	C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1864.7	Standard non polar	33892256
alpha-Ionone,1TBDMS,isomer #1	C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1896.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Ionone GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-4900000000-acff00e4fe614e1e5bc8	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Ionone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9800000000-d19fa6227b12fe21dbc3	2014-10-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 10V, Positive-QTOF	splash10-002f-0900000000-0d1ee7a07c25e0eb379a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 20V, Positive-QTOF	splash10-004u-3900000000-122599cd5a3606da3858	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 40V, Positive-QTOF	splash10-014i-9400000000-5525adff7c75947a3830	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 10V, Negative-QTOF	splash10-0006-0900000000-86ad4191ecec06d667eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 20V, Negative-QTOF	splash10-0006-0900000000-81ca79f706995e1f2313	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 40V, Negative-QTOF	splash10-0aed-2900000000-e754146e5b21f942f91e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 10V, Positive-QTOF	splash10-006x-0900000000-dca766c12d151f3d74b1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 20V, Positive-QTOF	splash10-05fu-8900000000-26ead371c8e940e8859e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 40V, Positive-QTOF	splash10-05mo-9600000000-ad142c26c199a3741a02	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 10V, Negative-QTOF	splash10-0006-0900000000-14436e4d9ff8d032db54	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 20V, Negative-QTOF	splash10-00di-0900000000-7cd7cf4235cb00fbc0b5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Ionone 40V, Negative-QTOF	splash10-0kmj-3900000000-b5da866d6db21994e86c	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	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

FDB014484

KNApSAcK ID

Not Available

Chemspider ID

4445317

KEGG Compound ID

C12286

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ionone

METLIN ID

Not Available

PubChem Compound

5282108

PDB ID

Not Available

ChEBI ID

32319

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for alpha-Ionone (HMDB0059883)

MOL for HMDB0059883 (alpha-Ionone)

3D MOL for HMDB0059883 (alpha-Ionone)

3D SDF for HMDB0059883 (alpha-Ionone)

3D-SDF for HMDB0059883 (alpha-Ionone)

PDB for HMDB0059883 (alpha-Ionone)

3D PDB for HMDB0059883 (alpha-Ionone)

SMILES for HMDB0059883 (alpha-Ionone)

INCHI for HMDB0059883 (alpha-Ionone)

Structure for HMDB0059883 (alpha-Ionone)

3D Structure for HMDB0059883 (alpha-Ionone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra