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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:07 UTC

Update Date

2023-02-21 17:22:16 UTC

HMDB ID

HMDB0032498

Secondary Accession Numbers

HMDB32498

Metabolite Identification

Common Name

Pseudoionone

Description

Pseudoionone (CAS: 141-10-6), also known as citrylideneacetone or psi-ionone, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Pseudoionone is an extremely weak basic (essentially neutral) compound (based on its pKa). Pseudoionone is a sweet, balsamic, and citrus tasting compound. Outside of the human body, pseudoionone has been detected, but not quantified in, a few different foods, such as cherry tomato and garden tomato. This could make pseudoionone a potential biomarker for the consumption of these foods. Pseudoionone is used as a food additive (EAFUS: Everything Added to Food in the United States).

Structure

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

HMDB0032498
     RDKit          3D
Pseudoionone
 34 33  0  0  0  0  0  0  0  0999 V2000
   -5.5441   -0.0770    0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2195   -1.3390    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1239   -2.1896    0.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8953   -1.6426   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9511   -0.7306   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5943   -0.9585   -0.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6417   -0.0646   -0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0246    1.1879    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7398   -0.3041   -0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454   -0.2861    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784   -0.5326   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0278    0.3828   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4032    0.1643   -0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7613    1.6384    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1825    0.8068    0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0798   -0.0215    1.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6334    0.0532    1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6157   -2.5301   -0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    0.2022    0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602   -1.9009   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7113    1.8220   -0.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4644    0.9621    1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381    1.8300    0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0601    0.4400   -1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -1.3040   -1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7761    0.7033    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732   -1.0858    1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2664   -1.4484   -0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096    0.6285   -0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4648    0.6068   -1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -0.9347   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741    2.2642    0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772    1.4245    1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6904    2.2330    0.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  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
  9 25  1  0
 10 26  1  0
 10 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


  Mrv1652304152023082D          

 14 13  0  0  0  0            999 V2000
    3.5500   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8356   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8356    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0222   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0222    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7367   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1656   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8801   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8801    0.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032498

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC\C(C)=C\C=C\C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h6-7,9-10H,5,8H2,1-4H3/b10-6+,12-9+

> <INCHI_KEY>
JXJIQCXXJGRKRJ-KOOBJXAQSA-N

> <FORMULA>
C13H20O

> <MOLECULAR_WEIGHT>
192.2973

> <EXACT_MASS>
192.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.217640234148014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,5E)-6,10-dimethylundeca-3,5,9-trien-2-one

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
3.67949903

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.728086372982204

> <JCHEM_PKA_STRONGEST_BASIC>
-4.545932361498589

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
64.9192

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pseudoionone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032498
     RDKit          3D
Pseudoionone
 34 33  0  0  0  0  0  0  0  0999 V2000
   -5.5441   -0.0770    0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2195   -1.3390    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1239   -2.1896    0.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8953   -1.6426   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9511   -0.7306   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5943   -0.9585   -0.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6417   -0.0646   -0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0246    1.1879    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7398   -0.3041   -0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454   -0.2861    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784   -0.5326   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0278    0.3828   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4032    0.1643   -0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7613    1.6384    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1825    0.8068    0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0798   -0.0215    1.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6334    0.0532    1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6157   -2.5301   -0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    0.2022    0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602   -1.9009   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7113    1.8220   -0.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4644    0.9621    1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381    1.8300    0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0601    0.4400   -1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -1.3040   -1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7761    0.7033    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732   -1.0858    1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2664   -1.4484   -0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096    0.6285   -0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4648    0.6068   -1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -0.9347   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741    2.2642    0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772    1.4245    1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6904    2.2330    0.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  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
  9 25  1  0
 10 26  1  0
 10 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                                 15-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-20         0                                  
HETATM    1  C   UNK     0       6.627  -0.935   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.293  -0.165   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.960  -0.935   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.626  -0.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.293   1.375   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.292  -0.935   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.041  -0.165   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.041   1.375   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.375  -0.935   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.709  -0.165   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.042  -0.935   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.376  -0.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.710  -0.935   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.376   1.375   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5    2                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0032498
HETATM    1  C1  UNL     1      -5.544  -0.077   0.942  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.220  -1.339   0.240  1.00  0.00           C  
HETATM    3  O1  UNL     1      -6.124  -2.190   0.071  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.895  -1.643  -0.265  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.951  -0.731  -0.076  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.594  -0.959  -0.553  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.642  -0.065  -0.375  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.025   1.188   0.337  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.740  -0.304  -0.865  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.745  -0.286   0.263  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.078  -0.533  -0.328  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.028   0.383  -0.189  1.00  0.00           C  
HETATM   13  C12 UNL     1       5.403   0.164  -0.781  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.761   1.638   0.549  1.00  0.00           C  
HETATM   15  H1  UNL     1      -5.182   0.807   0.337  1.00  0.00           H  
HETATM   16  H2  UNL     1      -5.080  -0.021   1.949  1.00  0.00           H  
HETATM   17  H3  UNL     1      -6.633   0.053   1.020  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.616  -2.530  -0.772  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.154   0.202   0.432  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.360  -1.901  -1.075  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.711   1.822  -0.284  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.464   0.962   1.335  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.138   1.830   0.549  1.00  0.00           H  
HETATM   24  H10 UNL     1       1.060   0.440  -1.624  1.00  0.00           H  
HETATM   25  H11 UNL     1       0.770  -1.304  -1.343  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.776   0.703   0.756  1.00  0.00           H  
HETATM   27  H13 UNL     1       1.473  -1.086   1.015  1.00  0.00           H  
HETATM   28  H14 UNL     1       3.266  -1.448  -0.863  1.00  0.00           H  
HETATM   29  H15 UNL     1       6.110   0.629  -0.067  1.00  0.00           H  
HETATM   30  H16 UNL     1       5.465   0.607  -1.802  1.00  0.00           H  
HETATM   31  H17 UNL     1       5.516  -0.935  -0.852  1.00  0.00           H  
HETATM   32  H18 UNL     1       2.974   2.264   0.081  1.00  0.00           H  
HETATM   33  H19 UNL     1       3.477   1.424   1.619  1.00  0.00           H  
HETATM   34  H20 UNL     1       4.690   2.233   0.615  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    7   20
CONECT    7    8    9
CONECT    8   21   22   23
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12   12   28
CONECT   12   13   14
CONECT   13   29   30   31
CONECT   14   32   33   34
END

HMDB0032498
     RDKit          3D
Pseudoionone
 34 33  0  0  0  0  0  0  0  0999 V2000
   -5.5441   -0.0770    0.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2195   -1.3390    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1239   -2.1896    0.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8953   -1.6426   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9511   -0.7306   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5943   -0.9585   -0.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6417   -0.0646   -0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0246    1.1879    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7398   -0.3041   -0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454   -0.2861    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784   -0.5326   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0278    0.3828   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4032    0.1643   -0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7613    1.6384    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1825    0.8068    0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0798   -0.0215    1.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6334    0.0532    1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6157   -2.5301   -0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    0.2022    0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602   -1.9009   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7113    1.8220   -0.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4644    0.9621    1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381    1.8300    0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0601    0.4400   -1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -1.3040   -1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7761    0.7033    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732   -1.0858    1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2664   -1.4484   -0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096    0.6285   -0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4648    0.6068   -1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -0.9347   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741    2.2642    0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772    1.4245    1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6904    2.2330    0.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  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
  9 25  1  0
 10 26  1  0
 10 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
(3E,5E)-6,10-Dimethylundeca-3,5,9-trien-2-one	ChEBI
2,6-Dimethylundeca-2,6,8-triene-10-one	ChEBI
6,10-Dimethyl-3,5,9-undecatrien-2-one	ChEBI
6,10-Dimethyl-3,5,9-undecatriene-2-one	ChEBI
Citrylideneacetone	ChEBI
(3E,5E)-6,10-Dimethyl-3,5,9-undecatrien-2-one	HMDB
.psi.-ionone	HMDB
2,6-Dimethyl hendeca-2,6,8-trien-10-one	HMDB
3,5,9-Undecatrien-2-one, 6,10-dimethyl, #1	HMDB
3,5,9-Undecatrien-2-one, 6,10-dimethyl, #2	HMDB
3,5,9-Undecatrien-2-one, 6,10-dimethyl, #3	HMDB
6,10-Dimethyl-(e,e)-3,5,9-undecatrien-2-one	HMDB
6,10-Dimethylundeca-3,5,9-trien-2-one	HMDB
8-[N-aziridylethylamino]-2,6-Dimethyloctene-2	HMDB
laquo psiraquo -Ionone	HMDB
N-[2-(1-Aziridinyl)ethyl]-3,7-dimethyl-6-octen-1-amine	HMDB
Pseudoionones	HMDB
psi-Ionone	HMDB
trans-.psi.-ionone	HMDB
(E,E)-6,10-Dimethyl-3,5,9-undecatrien-2-one	HMDB
(E,E)-Pseudoionone	HMDB
(all-E)-psi-Ionone	HMDB
(all-E)-ψ-Ionone	HMDB
2,6-Dimethyl-2,6,8-undecatrien-10-one	HMDB
2,6-Dimethylhendeca-2,6,8-trien-10-one	HMDB
2-Pseudoionone	HMDB
2-Pseudojonon	HMDB
3E,5E-Pseudoionone	HMDB
Pseudoionone	HMDB
phi-Ionone	HMDB
trans,trans-Pseudoionone	HMDB
trans-psi-Ionone	HMDB
trans-ψ-Ionone	HMDB
φ-Ionone	HMDB
ψ-Ionone	HMDB

Chemical Formula

C₁₃H₂₀O

Average Molecular Weight

192.2973

Monoisotopic Molecular Weight

192.151415262

IUPAC Name

(3E,5E)-6,10-dimethylundeca-3,5,9-trien-2-one

Traditional Name

pseudoionone

CAS Registry Number

3548-78-5

SMILES

CC(C)=CCC\C(C)=C\C=C\C(C)=O

InChI Identifier

InChI=1S/C13H20O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h6-7,9-10H,5,8H2,1-4H3/b10-6+,12-9+

InChI Key

JXJIQCXXJGRKRJ-KOOBJXAQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

terpene ketone (CHEBI:67207 )

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032498)

Source

Endogenous

Endogenous (HMDB: HMDB0032498)

Animal

Animal (HMDB: HMDB0032498)

Exogenous

Food

Food (HMDB: HMDB0032498)

Vegetable

Fruit vegetable

Exogenous (HMDB: HMDB0032498)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032498)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032498)

Lipid metabolism pathway (HMDB: HMDB0032498)

Cellular process

Cell signaling (HMDB: HMDB0032498)

Biochemical process

Lipid transport (HMDB: HMDB0032498)

Role

Biological role

Energy source (HMDB: HMDB0032498)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032498)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	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	0.079 g/L	ALOGPS
logP	4.57	ALOGPS
logP	3.68	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	19.73	ChemAxon
pKa (Strongest Basic)	-4.5	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	5	ChemAxon
Refractivity	64.92 m³·mol⁻¹	ChemAxon
Polarizability	24.22 Å³	ChemAxon
Number of Rings	0	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]+	150.539	30932474
DeepCCS	[M-H]-	147.884	30932474
DeepCCS	[M-2H]-	183.804	30932474
DeepCCS	[M+Na]+	159.396	30932474
AllCCS	[M+H]+	147.9	32859911
AllCCS	[M+H-H2O]+	144.0	32859911
AllCCS	[M+NH4]+	151.5	32859911
AllCCS	[M+Na]+	152.5	32859911
AllCCS	[M-H]-	148.0	32859911
AllCCS	[M+Na-2H]-	149.2	32859911
AllCCS	[M+HCOO]-	150.7	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. Predicted by Afia on May 17, 2022.	8.25 minutes	32390414
Predicted by Siyang on May 30, 2022	17.764 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.43 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2551.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	565.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	221.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	358.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	127.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	634.0 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	603.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1542.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	580.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1187.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	538.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	401.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	318.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	563.7 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pseudoionone	CC(C)=CCC\C(C)=C\C=C\C(C)=O	1976.7	Standard polar	33892256
Pseudoionone	CC(C)=CCC\C(C)=C\C=C\C(C)=O	1524.2	Standard non polar	33892256
Pseudoionone	CC(C)=CCC\C(C)=C\C=C\C(C)=O	1577.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pseudoionone,1TMS,isomer #1	C=C(/C=C/C=C(\C)CCC=C(C)C)O[Si](C)(C)C	1688.7	Semi standard non polar	33892256
Pseudoionone,1TMS,isomer #1	C=C(/C=C/C=C(\C)CCC=C(C)C)O[Si](C)(C)C	1668.2	Standard non polar	33892256
Pseudoionone,1TBDMS,isomer #1	C=C(/C=C/C=C(\C)CCC=C(C)C)O[Si](C)(C)C(C)(C)C	1917.0	Semi standard non polar	33892256
Pseudoionone,1TBDMS,isomer #1	C=C(/C=C/C=C(\C)CCC=C(C)C)O[Si](C)(C)C(C)(C)C	1883.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pseudoionone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05mo-9500000000-88a840082ecbb350c6a6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pseudoionone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pseudoionone 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 - Pseudoionone 10V, Positive-QTOF	splash10-002f-0900000000-2db17f4b4c990b982341	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 20V, Positive-QTOF	splash10-00pu-4900000000-52ad299b7419d9c48519	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 40V, Positive-QTOF	splash10-0gb9-9200000000-2d38b7ef565b063e02a1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 10V, Negative-QTOF	splash10-0006-0900000000-32871f26fdd2d0019cb5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 20V, Negative-QTOF	splash10-0006-0900000000-575b176dca9d2bf2b4cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 40V, Negative-QTOF	splash10-0a6u-4900000000-19449ebc8c2cc7ea297d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 10V, Negative-QTOF	splash10-0006-0900000000-982b69b98355bf67bf41	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 20V, Negative-QTOF	splash10-0a4l-4900000000-715808bcaeeaf260c181	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 40V, Negative-QTOF	splash10-0aor-5900000000-7fc4257f2401238154ab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 10V, Positive-QTOF	splash10-00l6-9800000000-0f5de46efabff5d3d2ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 20V, Positive-QTOF	splash10-05qc-9200000000-8a02cf4811e6304593e4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoionone 40V, Positive-QTOF	splash10-0006-9200000000-a6eda7fe87b35637f77c	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

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

FDB010156

KNApSAcK ID

Not Available

Chemspider ID

1387980

KEGG Compound ID

Not Available

BioCyc ID

CPD-13371

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1757003

PDB ID

Not Available

ChEBI ID

67207

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 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Pseudoionone (HMDB0032498)

MOL for HMDB0032498 (Pseudoionone)

3D MOL for HMDB0032498 (Pseudoionone)

3D SDF for HMDB0032498 (Pseudoionone)

3D-SDF for HMDB0032498 (Pseudoionone)

PDB for HMDB0032498 (Pseudoionone)

3D PDB for HMDB0032498 (Pseudoionone)

SMILES for HMDB0032498 (Pseudoionone)

INCHI for HMDB0032498 (Pseudoionone)

Structure for HMDB0032498 (Pseudoionone)

3D Structure for HMDB0032498 (Pseudoionone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra