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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 22:23:05 UTC

Update Date

2023-02-21 17:25:36 UTC

HMDB ID

HMDB0037139

Secondary Accession Numbers

HMDB37139

Metabolite Identification

Common Name

4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone

Description

4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone, also known as 3,4-didehydro-7,8-dihydro-beta-ionone or dehydrodihydroionone, 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-1,3-cyclohexadien-1-yl)-2-butanone.

Structure

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

HMDB0037139
     RDKit          3D
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.3756    0.9645    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    1.1373    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5517    2.1717   -0.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0470   -0.0470    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7530    0.3732   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4778   -0.3456   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246   -1.6086    0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -2.3840    0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066   -2.3222   -0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8798   -1.6067   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -0.1880   -1.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.5114   -0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0756    1.2913    0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987    1.6301   -1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5554    1.0349    1.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9741    1.7528    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7933   -0.0189    0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6175   -0.8072   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801   -0.2085    1.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    1.3075    0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8976    0.8989   -1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356   -2.6329   -0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282   -3.4465    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -2.1718    1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0099   -3.3688    0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8268   -2.1555   -0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737   -0.1299   -2.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7728    0.3357   -0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9965    0.8373    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2620    2.3404    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2795    1.1283    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065    2.1907   -1.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5634    2.3024   -0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6741    1.2337   -2.3539 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  2  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
 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


  Mrv0541 02241220212D          

 14 14  0  0  0  0            999 V2000
   -2.1422    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7165   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7165    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8411    1.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0161    1.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7122    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1422    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
 10 11  1  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>
HMDB0037139

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h5-6H,7-9H2,1-4H3

> <INCHI_KEY>
SQFRYZPEWOZAKJ-UHFFFAOYSA-N

> <FORMULA>
C13H20O

> <MOLECULAR_WEIGHT>
192.2973

> <EXACT_MASS>
192.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.142736368952797

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
2.915878524

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.595050091645906

> <JCHEM_PKA_STRONGEST_BASIC>
-7.278062241294736

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
61.8454

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037139
     RDKit          3D
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.3756    0.9645    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    1.1373    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5517    2.1717   -0.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0470   -0.0470    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7530    0.3732   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4778   -0.3456   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246   -1.6086    0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -2.3840    0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066   -2.3222   -0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8798   -1.6067   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -0.1880   -1.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.5114   -0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0756    1.2913    0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987    1.6301   -1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5554    1.0349    1.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9741    1.7528    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7933   -0.0189    0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6175   -0.8072   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801   -0.2085    1.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    1.3075    0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8976    0.8989   -1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356   -2.6329   -0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282   -3.4465    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -2.1718    1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0099   -3.3688    0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8268   -2.1555   -0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737   -0.1299   -2.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7728    0.3357   -0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9965    0.8373    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2620    2.3404    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2795    1.1283    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065    2.1907   -1.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5634    2.3024   -0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6741    1.2337   -2.3539 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  2  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
 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.999   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.999  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.337  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.337   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.765   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.437   2.102   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.897   2.102   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.765   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.329   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.662   0.765   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.999   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.662   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4                                                            
CONECT   10    5   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   28    0
END

COMPND    HMDB0037139
HETATM    1  C1  UNL     1       4.376   0.965   0.591  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.972   1.137   0.212  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.552   2.172  -0.186  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.047  -0.047   0.338  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.753   0.373  -0.087  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.478  -0.346  -0.192  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.625  -1.609   0.057  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.530  -2.384   0.488  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.907  -2.322  -0.179  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.880  -1.607  -0.667  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.826  -0.188  -1.004  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.651   0.511  -0.531  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.076   1.291   0.745  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.199   1.630  -1.488  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.555   1.035   1.687  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.974   1.753   0.056  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.793  -0.019   0.230  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.618  -0.807  -0.227  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.080  -0.208   1.457  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.504   1.307   0.544  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.898   0.899  -1.103  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.236  -2.633  -0.360  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.128  -3.447   0.681  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.989  -2.172   1.439  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.010  -3.369   0.044  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.827  -2.156  -0.829  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.874  -0.130  -2.158  1.00  0.00           H  
HETATM   28  H14 UNL     1      -3.773   0.336  -0.656  1.00  0.00           H  
HETATM   29  H15 UNL     1      -2.996   0.837   1.177  1.00  0.00           H  
HETATM   30  H16 UNL     1      -2.262   2.340   0.543  1.00  0.00           H  
HETATM   31  H17 UNL     1      -1.279   1.128   1.494  1.00  0.00           H  
HETATM   32  H18 UNL     1      -2.106   2.191  -1.742  1.00  0.00           H  
HETATM   33  H19 UNL     1      -0.563   2.302  -0.878  1.00  0.00           H  
HETATM   34  H20 UNL     1      -0.674   1.234  -2.354  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   10   25
CONECT   10   11   26
CONECT   11   12   27   28
CONECT   12   13   14
CONECT   13   29   30   31
CONECT   14   32   33   34
END

HMDB0037139
     RDKit          3D
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.3756    0.9645    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9719    1.1373    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5517    2.1717   -0.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0470   -0.0470    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7530    0.3732   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4778   -0.3456   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246   -1.6086    0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -2.3840    0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066   -2.3222   -0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8798   -1.6067   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -0.1880   -1.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.5114   -0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0756    1.2913    0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987    1.6301   -1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5554    1.0349    1.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9741    1.7528    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7933   -0.0189    0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6175   -0.8072   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801   -0.2085    1.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    1.3075    0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8976    0.8989   -1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356   -2.6329   -0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282   -3.4465    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -2.1718    1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0099   -3.3688    0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8268   -2.1555   -0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737   -0.1299   -2.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7728    0.3357   -0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9965    0.8373    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2620    2.3404    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2795    1.1283    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1065    2.1907   -1.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5634    2.3024   -0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6741    1.2337   -2.3539 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  2  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
 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
3,4-Didehydro-7,8-dihydro-beta-ionone	ChEBI
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)butan-2-one	ChEBI
4-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-butanone	ChEBI
4-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)butan-2-one	ChEBI
4-(2,6,6-Trimethylcyclohexa-1,3-dienyl)butan-2-one	ChEBI
7,8-Dihydro-3,4-dehydro-beta-ionone	ChEBI
Dehydrodihydroionone	ChEBI
FEMA 3447	ChEBI
3,4-Didehydro-7,8-dihydro-b-ionone	Generator
3,4-Didehydro-7,8-dihydro-β-ionone	Generator
7,8-Dihydro-3,4-dehydro-b-ionone	Generator
7,8-Dihydro-3,4-dehydro-β-ionone	Generator
4-(2,6,6-Trimethyl cyclohexa-1,3-dienyl) butane-2-one	HMDB
dihydrodehydro-beta-Ionone	HMDB

Chemical Formula

C₁₃H₂₀O

Average Molecular Weight

192.2973

Monoisotopic Molecular Weight

192.151415262

IUPAC Name

4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one

Traditional Name

4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one

CAS Registry Number

20483-36-7

SMILES

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

InChI Identifier

InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h5-6H,7-9H2,1-4H3

InChI Key

SQFRYZPEWOZAKJ-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

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

Floral

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037139)

Source

Endogenous

Endogenous (HMDB: HMDB0037139)

Plant

Plant (HMDB: HMDB0037139)

Animal

Animal (HMDB: HMDB0037139)

Exogenous

Food

Food (HMDB: HMDB0037139)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0037139)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037139)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037139)

Lipid metabolism pathway (HMDB: HMDB0037139)

Cellular process

Cell signaling (HMDB: HMDB0037139)

Biochemical process

Lipid transport (HMDB: HMDB0037139)

Role

Biological role

Energy source (HMDB: HMDB0037139)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037139)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037139)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	126.00 to 128.00 °C. @ 12.00 mm Hg	The Good Scents Company Information System
Water Solubility	14.09 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.681 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	4.15	ALOGPS
logP	2.92	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	61.85 m³·mol⁻¹	ChemAxon
Polarizability	23.14 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]+	147.051	31661259
DarkChem	[M-H]-	143.569	31661259
DeepCCS	[M+H]+	147.682	30932474
DeepCCS	[M-H]-	145.324	30932474
DeepCCS	[M-2H]-	180.549	30932474
DeepCCS	[M+Na]+	155.149	30932474
AllCCS	[M+H]+	143.5	32859911
AllCCS	[M+H-H2O]+	139.5	32859911
AllCCS	[M+NH4]+	147.3	32859911
AllCCS	[M+Na]+	148.4	32859911
AllCCS	[M-H]-	149.8	32859911
AllCCS	[M+Na-2H]-	150.8	32859911
AllCCS	[M+HCOO]-	151.9	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.	7.2 minutes	32390414
Predicted by Siyang on May 30, 2022	18.548 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.45 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2467.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	617.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	233.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	384.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	691.2 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	719.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1522.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	516.0 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	1346.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	533.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	421.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	424.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	623.4 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone	CC(=O)CCC1=C(C)C=CCC1(C)C	1879.0	Standard polar	33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone	CC(=O)CCC1=C(C)C=CCC1(C)C	1395.9	Standard non polar	33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone	CC(=O)CCC1=C(C)C=CCC1(C)C	1413.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TMS,isomer #1	CC(=CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C	1661.8	Semi standard non polar	33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TMS,isomer #1	CC(=CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C	1606.2	Standard non polar	33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TMS,isomer #2	C=C(CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C	1640.2	Semi standard non polar	33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TMS,isomer #2	C=C(CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C	1590.3	Standard non polar	33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TBDMS,isomer #1	CC(=CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C(C)(C)C	1905.7	Semi standard non polar	33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TBDMS,isomer #1	CC(=CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C(C)(C)C	1867.1	Standard non polar	33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TBDMS,isomer #2	C=C(CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C(C)(C)C	1878.4	Semi standard non polar	33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TBDMS,isomer #2	C=C(CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C(C)(C)C	1843.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-5900000000-5736fe8e960c46e93ba3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-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-1,3-cyclohexadien-1-yl)-2-butanone 10V, Positive-QTOF	splash10-002f-1900000000-0e04520fc1c4c99c5426	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 20V, Positive-QTOF	splash10-00p3-4900000000-95189d759958da4cd7db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 40V, Positive-QTOF	splash10-0gb9-9400000000-a0c1a282f3fe2da24144	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 10V, Negative-QTOF	splash10-0006-0900000000-88505512782936b3ed7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 20V, Negative-QTOF	splash10-0006-2900000000-d9772c13d17a491dc87d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 40V, Negative-QTOF	splash10-0a4i-9600000000-d83f781d2e263e20e007	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 10V, Positive-QTOF	splash10-0019-0900000000-25eb405119b32dd9570a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 20V, Positive-QTOF	splash10-05g3-5900000000-f9568278d81f5d6dc1b3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 40V, Positive-QTOF	splash10-05mo-9400000000-cdeeb27239a996dcb3ab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 10V, Negative-QTOF	splash10-0006-0900000000-14436e4d9ff8d032db54	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 20V, Negative-QTOF	splash10-00dl-2900000000-4fc59527a3e46530a631	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 40V, Negative-QTOF	splash10-052e-5900000000-68b6ab45c521a59d612e	2021-09-23	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

FDB016134

KNApSAcK ID

Not Available

Chemspider ID

501713

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

577126

PDB ID

Not Available

ChEBI ID

88549

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1042201

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-1,3-cyclohexadien-1-yl)-2-butanone (HMDB0037139)

MOL for HMDB0037139 (4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone)

3D MOL for HMDB0037139 (4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone)

3D SDF for HMDB0037139 (4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone)

3D-SDF for HMDB0037139 (4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone)

PDB for HMDB0037139 (4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone)

3D PDB for HMDB0037139 (4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone)

SMILES for HMDB0037139 (4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone)

INCHI for HMDB0037139 (4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone)

Structure for HMDB0037139 (4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone)

3D Structure for HMDB0037139 (4-(2,6,6-Trimethyl-1,3-cyclohexadien-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