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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:10 UTC

Update Date

2022-03-07 02:52:15 UTC

HMDB ID

HMDB0029704

Secondary Accession Numbers

HMDB29704

Metabolite Identification

Common Name

1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one

Description

1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one.

Structure

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

HMDB0029704
     RDKit          3D
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.0737   -1.0094   -1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3489   -0.3394    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213    0.3728    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466    0.2512    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9764    0.9737    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.5750    2.0783 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430    1.0532    0.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176    0.4570   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4274    0.5246   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1243    1.2805    0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246    2.7192    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562    0.6671    1.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831   -0.7561    1.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407   -1.5119    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0165   -0.8714   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116   -0.8445   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053   -1.6728   -1.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0494   -1.0615   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8121   -1.5340   -1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3729   -0.3138    0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5840    1.4455    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3063   -0.0256    1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634   -0.7986    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9902    0.7603   -0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479    1.5980    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7231   -0.0893   -0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    0.9881   -1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4472    2.8398   -0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254    3.1472   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2789    3.3375    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661    1.2514    2.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1382   -1.2230    2.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4869   -0.8782    2.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5343   -1.5820    0.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807   -2.5481    0.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8698   -1.7471   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9862   -0.9007    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9164    0.0295   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583   -1.7165   -2.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886   -2.6772   -1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5145   -1.1705   -2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv0541 02241217452D          

 17 17  0  0  0  0            999 V2000
   -3.2138    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2138   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -1.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9128    1.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0883    1.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0739    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552    1.2368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7845    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2138    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0739   -1.2368    0.0000 C   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  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 17  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029704

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CCCC(C)(C)C1\C=C\C(=O)CCC=C

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O/c1-5-6-9-14(17)10-11-15-13(2)8-7-12-16(15,3)4/h5,8,10-11,15H,1,6-7,9,12H2,2-4H3/b11-10+

> <INCHI_KEY>
FXCYGAGBPZQRJE-ZHACJKMWSA-N

> <FORMULA>
C16H24O

> <MOLECULAR_WEIGHT>
232.3612

> <EXACT_MASS>
232.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.049340053519032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.79

> <JCHEM_LOGP>
4.604966685666666

> <ALOGPS_LOGS>
-4.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.988756471608805

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
75.9617

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)hepta-1,6-dien-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0029704
     RDKit          3D
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.0737   -1.0094   -1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3489   -0.3394    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213    0.3728    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466    0.2512    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9764    0.9737    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.5750    2.0783 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430    1.0532    0.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176    0.4570   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4274    0.5246   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1243    1.2805    0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246    2.7192    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562    0.6671    1.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831   -0.7561    1.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407   -1.5119    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0165   -0.8714   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116   -0.8445   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053   -1.6728   -1.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0494   -1.0615   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8121   -1.5340   -1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3729   -0.3138    0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5840    1.4455    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3063   -0.0256    1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634   -0.7986    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9902    0.7603   -0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479    1.5980    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7231   -0.0893   -0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    0.9881   -1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4472    2.8398   -0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254    3.1472   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2789    3.3375    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661    1.2514    2.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1382   -1.2230    2.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4869   -0.8782    2.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5343   -1.5820    0.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807   -2.5481    0.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8698   -1.7471   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9862   -0.9007    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9164    0.0295   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583   -1.7165   -2.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886   -2.6772   -1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5145   -1.1705   -2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  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      -5.999   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.999  -1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.668  -2.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.339  -1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.339   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.668   0.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.437   2.101   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.898   2.101   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.005   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.671   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.663   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.663   2.309   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.997   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.331   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.665   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.999   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.005  -2.309   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6    9                                                  
CONECT    6    1    5    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    4                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0029704
HETATM    1  C1  UNL     1       5.074  -1.009  -1.064  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.349  -0.339   0.046  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.321   0.373   0.828  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.947   0.251   0.232  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.976   0.974   1.045  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.364   1.575   2.078  1.00  0.00           O  
HETATM    7  C6  UNL     1       0.543   1.053   0.738  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.018   0.457  -0.329  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.427   0.525  -0.657  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.124   1.280   0.405  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.425   2.719   0.159  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.456   0.667   1.525  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.183  -0.756   1.821  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.641  -1.512   0.657  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.017  -0.871  -0.682  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.512  -0.845  -0.748  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.405  -1.673  -1.790  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.049  -1.061  -1.452  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.812  -1.534  -1.645  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.373  -0.314   0.393  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.584   1.445   0.879  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.306  -0.026   1.864  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.663  -0.799   0.018  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.990   0.760  -0.775  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.148   1.598   1.363  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.723  -0.089  -0.952  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.564   0.988  -1.663  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.447   2.840  -0.251  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.725   3.147  -0.597  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.279   3.337   1.076  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.966   1.251   2.282  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.138  -1.223   2.144  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.487  -0.878   2.692  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.534  -1.582   0.650  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.081  -2.548   0.607  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.870  -1.747  -1.287  1.00  0.00           H  
HETATM   37  H20 UNL     1      -3.986  -0.901   0.271  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.916   0.030  -1.282  1.00  0.00           H  
HETATM   39  H22 UNL     1      -2.158  -1.717  -2.627  1.00  0.00           H  
HETATM   40  H23 UNL     1      -1.089  -2.677  -1.476  1.00  0.00           H  
HETATM   41  H24 UNL     1      -0.515  -1.170  -2.238  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6    6    7
CONECT    7    8    8   25
CONECT    8    9   26
CONECT    9   10   15   27
CONECT   10   11   12   12
CONECT   11   28   29   30
CONECT   12   13   31
CONECT   13   14   32   33
CONECT   14   15   34   35
CONECT   15   16   17
CONECT   16   36   37   38
CONECT   17   39   40   41
END

HMDB0029704
     RDKit          3D
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.0737   -1.0094   -1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3489   -0.3394    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213    0.3728    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466    0.2512    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9764    0.9737    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.5750    2.0783 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430    1.0532    0.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176    0.4570   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4274    0.5246   -0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1243    1.2805    0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4246    2.7192    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4562    0.6671    1.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831   -0.7561    1.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407   -1.5119    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0165   -0.8714   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116   -0.8445   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053   -1.6728   -1.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0494   -1.0615   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8121   -1.5340   -1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3729   -0.3138    0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5840    1.4455    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3063   -0.0256    1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634   -0.7986    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9902    0.7603   -0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479    1.5980    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7231   -0.0893   -0.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    0.9881   -1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4472    2.8398   -0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254    3.1472   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2789    3.3375    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661    1.2514    2.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1382   -1.2230    2.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4869   -0.8782    2.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5343   -1.5820    0.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807   -2.5481    0.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8698   -1.7471   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9862   -0.9007    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9164    0.0295   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583   -1.7165   -2.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886   -2.6772   -1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5145   -1.1705   -2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Allyl alpha-ionone	HMDB
Allyl ionone	HMDB
Allyl-a-ionone	HMDB
Cetone V	HMDB
FEMA 2033	HMDB
Hexalon	HMDB
Polyone	HMDB

Chemical Formula

C₁₆H₂₄O

Average Molecular Weight

232.3612

Monoisotopic Molecular Weight

232.18271539

IUPAC Name

(1E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)hepta-1,6-dien-3-one

Traditional Name

(1E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)hepta-1,6-dien-3-one

CAS Registry Number

79-78-7

SMILES

CC1=CCCC(C)(C)C1\C=C\C(=O)CCC=C

InChI Identifier

InChI=1S/C16H24O/c1-5-6-9-14(17)10-11-15-13(2)8-7-12-16(15,3)4/h5,8,10-11,15H,1,6-7,9,12H2,2-4H3/b11-10+

InChI Key

FXCYGAGBPZQRJE-ZHACJKMWSA-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

Not Available

Ontology

Cytoplasm (HMDB: HMDB0029704)
Cell membrane (HMDB: HMDB0029704)

Cellular substructure

Extracellular (HMDB: HMDB0029704)
Membrane (HMDB: HMDB0029704)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029704)

Source

Endogenous

Endogenous (HMDB: HMDB0029704)

Animal

Animal (HMDB: HMDB0029704)

Exogenous

Food

Food (HMDB: HMDB0029704)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0029704)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0029704)

Cellular process

Cell signaling (HMDB: HMDB0029704)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0029704)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0029704)

Nutrient

Nutrient (HMDB: HMDB0029704)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0029704)

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0029704)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	422.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	19.78 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.470 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0046 g/L	ALOGPS
logP	4.79	ALOGPS
logP	4.6	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-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	75.96 m³·mol⁻¹	ChemAxon
Polarizability	28.05 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]+	162.09	30932474
DeepCCS	[M-H]-	159.732	30932474
DeepCCS	[M-2H]-	193.501	30932474
DeepCCS	[M+Na]+	168.571	30932474
AllCCS	[M+H]+	157.7	32859911
AllCCS	[M+H-H2O]+	154.0	32859911
AllCCS	[M+NH4]+	161.1	32859911
AllCCS	[M+Na]+	162.1	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	164.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one	CC1=CCCC(C)(C)C1\C=C\C(=O)CCC=C	2163.4	Standard polar	33892256
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one	CC1=CCCC(C)(C)C1\C=C\C(=O)CCC=C	1666.6	Standard non polar	33892256
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one	CC1=CCCC(C)(C)C1\C=C\C(=O)CCC=C	1742.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one,1TMS,isomer #1	C=CCC=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C	1936.4	Semi standard non polar	33892256
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one,1TMS,isomer #1	C=CCC=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C	1891.8	Standard non polar	33892256
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one,1TBDMS,isomer #1	C=CCC=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C	2184.2	Semi standard non polar	33892256
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one,1TBDMS,isomer #1	C=CCC=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C	2109.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-05p6-5940000000-beba5be45477f5c3ad42	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 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 - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 10V, Positive-QTOF	splash10-001i-1390000000-ea4eff05669679da083a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 20V, Positive-QTOF	splash10-05q3-5920000000-d87dbb8ca107ff9e9bda	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 40V, Positive-QTOF	splash10-0pvl-9410000000-5c6850c33ae570944880	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 10V, Negative-QTOF	splash10-001i-0190000000-20c3289c174a5d0de509	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 20V, Negative-QTOF	splash10-001i-5890000000-15fe54067e90dcd90f37	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 40V, Negative-QTOF	splash10-00a6-4900000000-d80e4de9b081588ebb05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 10V, Positive-QTOF	splash10-001i-2960000000-970c92a8fa827f5daecd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 20V, Positive-QTOF	splash10-0ab9-4900000000-85265409d87491560de1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 40V, Positive-QTOF	splash10-0a4i-9700000000-4890e1e1236f74a37074	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 10V, Negative-QTOF	splash10-001i-0090000000-d40d073e08bfd2986036	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 20V, Negative-QTOF	splash10-0002-0910000000-50b2b0b1139a16cf896f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one 40V, Negative-QTOF	splash10-0ac0-5900000000-243da8f4263cb5a40702	2021-09-23	Wishart 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

FDB000898

KNApSAcK ID

Not Available

Chemspider ID

4517909

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5365976

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1504331

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 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one (HMDB0029704)

MOL for HMDB0029704 (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one)

3D MOL for HMDB0029704 (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one)

3D SDF for HMDB0029704 (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one)

3D-SDF for HMDB0029704 (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one)

PDB for HMDB0029704 (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one)

3D PDB for HMDB0029704 (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one)

SMILES for HMDB0029704 (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one)

INCHI for HMDB0029704 (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one)

Structure for HMDB0029704 (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one)

3D Structure for HMDB0029704 (1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra