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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:07 UTC

Update Date

2023-02-21 17:21:17 UTC

HMDB ID

HMDB0031738

Secondary Accession Numbers

HMDB31738

Metabolite Identification

Common Name

3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one

Description

3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-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 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one.

Structure

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

HMDB0031738
     RDKit          3D
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.4401   -0.0236    0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -0.5242    0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8780   -1.5882    1.5234 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9138    0.1764    0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813    1.4313   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -0.3101    0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294    0.3650   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430    0.7790    1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196    2.2045    1.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337   -0.1314    1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -1.5470    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2017   -1.5075   -0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2020   -0.5859   -0.9788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -1.3568   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9156    0.2556   -2.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1701   -0.8081    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5656    0.2772   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5643    0.8867    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660    2.2604   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    1.7409   -0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279    1.2654   -1.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155   -1.2278    1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008    1.2748   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564    2.4396    2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6367    2.8268    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4195    2.4978    1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8944    0.2255    2.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410   -1.9453    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974   -2.1868    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0273   -2.5331   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206   -1.2397   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8702   -0.9234   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3600   -1.4300   -2.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -2.3998   -1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536   -0.4274   -2.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2263    1.0451   -2.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696    0.7440   -1.5138 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
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END


  Mrv0541 05061306062D          

 15 15  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  7  2  0  0  0  0
 11  2  1  0  0  0  0
 11  9  2  0  0  0  0
 12  3  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031738

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O/c1-10-7-6-8-14(4,5)13(10)9-11(2)12(3)15/h7,9,13H,6,8H2,1-5H3/b11-9+

> <INCHI_KEY>
JRJBVWJSTHECJK-PKNBQFBNSA-N

> <FORMULA>
C14H22O

> <MOLECULAR_WEIGHT>
206.3239

> <EXACT_MASS>
206.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
24.9627973860611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
3.714831984333335

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.70086228673985

> <JCHEM_PKA_STRONGEST_BASIC>
-4.846295705534975

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
66.4458

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.40e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0031738
     RDKit          3D
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.4401   -0.0236    0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -0.5242    0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8780   -1.5882    1.5234 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9138    0.1764    0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813    1.4313   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -0.3101    0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294    0.3650   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430    0.7790    1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196    2.2045    1.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337   -0.1314    1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -1.5470    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2017   -1.5075   -0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2020   -0.5859   -0.9788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -1.3568   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9156    0.2556   -2.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1701   -0.8081    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5656    0.2772   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5643    0.8867    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660    2.2604   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    1.7409   -0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279    1.2654   -1.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155   -1.2278    1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008    1.2748   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564    2.4396    2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6367    2.8268    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4195    2.4978    1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8944    0.2255    2.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410   -1.9453    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974   -2.1868    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0273   -2.5331   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206   -1.2397   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8702   -0.9234   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3600   -1.4300   -2.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -2.3998   -1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536   -0.4274   -2.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2263    1.0451   -2.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696    0.7440   -1.5138 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
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   14                                                            
CONECT    5   14                                                            
CONECT    6    7    8                                                       
CONECT    7    6   10                                                       
CONECT    8    6   14                                                       
CONECT    9   11   13                                                       
CONECT   10    1    7   13                                                  
CONECT   11    2    9   12                                                  
CONECT   12    3   11   15                                                  
CONECT   13    9   10   14                                                  
CONECT   14    4    5    8   13                                             
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0031738
HETATM    1  C1  UNL     1       4.440  -0.024   0.724  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.060  -0.524   0.884  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.878  -1.588   1.523  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.914   0.176   0.326  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.081   1.431  -0.428  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.694  -0.310   0.495  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.529   0.365  -0.056  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.443   0.779   1.035  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.420   2.205   1.470  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.234  -0.131   1.570  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.238  -1.547   1.117  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.202  -1.508  -0.387  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.202  -0.586  -0.979  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.130  -1.357  -1.755  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.916   0.256  -2.051  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.170  -0.808   1.002  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.566   0.277  -0.348  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.564   0.887   1.355  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.466   2.260  -0.024  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.146   1.741  -0.358  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.828   1.265  -1.483  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.616  -1.228   1.055  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.201   1.275  -0.657  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.156   2.440   2.235  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.637   2.827   0.577  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.419   2.498   1.864  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.894   0.226   2.378  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.241  -1.945   1.404  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.497  -2.187   1.587  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.027  -2.533  -0.820  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.221  -1.240  -0.725  1.00  0.00           H  
HETATM   32  H17 UNL     1       0.870  -0.923  -1.606  1.00  0.00           H  
HETATM   33  H18 UNL     1      -0.360  -1.430  -2.822  1.00  0.00           H  
HETATM   34  H19 UNL     1      -0.076  -2.400  -1.332  1.00  0.00           H  
HETATM   35  H20 UNL     1      -2.254  -0.427  -2.842  1.00  0.00           H  
HETATM   36  H21 UNL     1      -1.226   1.045  -2.415  1.00  0.00           H  
HETATM   37  H22 UNL     1      -2.770   0.744  -1.514  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5    6    6
CONECT    5   19   20   21
CONECT    6    7   22
CONECT    7    8   13   23
CONECT    8    9   10   10
CONECT    9   24   25   26
CONECT   10   11   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   15
CONECT   14   32   33   34
CONECT   15   35   36   37
END

HMDB0031738
     RDKit          3D
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.4401   -0.0236    0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -0.5242    0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8780   -1.5882    1.5234 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9138    0.1764    0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813    1.4313   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -0.3101    0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294    0.3650   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430    0.7790    1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196    2.2045    1.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337   -0.1314    1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -1.5470    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2017   -1.5075   -0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2020   -0.5859   -0.9788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -1.3568   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9156    0.2556   -2.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1701   -0.8081    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5656    0.2772   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5643    0.8867    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660    2.2604   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    1.7409   -0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279    1.2654   -1.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155   -1.2278    1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008    1.2748   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564    2.4396    2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6367    2.8268    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4195    2.4978    1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8944    0.2255    2.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410   -1.9453    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974   -2.1868    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0273   -2.5331   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206   -1.2397   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8702   -0.9234   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3600   -1.4300   -2.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -2.3998   -1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536   -0.4274   -2.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2263    1.0451   -2.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696    0.7440   -1.5138 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
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Methyl-a-ionone	HMDB
Cetone alpha	HMDB
FEMA 2714	HMDB
Isomethyl-a-ionone	HMDB
alpha-Isomethyl ionone	MeSH, HMDB
alpha-Isomethylionone	MeSH, HMDB
Methyl ionone gamma	MeSH, HMDB

Chemical Formula

C₁₄H₂₂O

Average Molecular Weight

206.3239

Monoisotopic Molecular Weight

206.167065326

IUPAC Name

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

Traditional Name

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

CAS Registry Number

127-51-5

SMILES

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

InChI Identifier

InChI=1S/C14H22O/c1-10-7-6-8-14(4,5)13(10)9-11(2)12(3)15/h7,9,13H,6,8H2,1-5H3/b11-9+

InChI Key

JRJBVWJSTHECJK-PKNBQFBNSA-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-branched alpha,beta-unsaturated-ketone
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

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031738)

Source

Exogenous

Food

Food (HMDB: HMDB0031738)

Exogenous (HMDB: HMDB0031738)

Endogenous

Animal

Animal (HMDB: HMDB0031738)

Endogenous (HMDB: HMDB0031738)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031738)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031738)

Lipid metabolism pathway (HMDB: HMDB0031738)

Cellular process

Cell signaling (HMDB: HMDB0031738)

Biochemical process

Lipid transport (HMDB: HMDB0031738)

Role

Biological role

Energy source (HMDB: HMDB0031738)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031738)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031738)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	76.00 °C. @ 0.30 mm Hg	The Good Scents Company Information System
Water Solubility	2.98 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.315	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.064 g/L	ALOGPS
logP	4.69	ALOGPS
logP	3.71	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	19.7	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.45 m³·mol⁻¹	ChemAxon
Polarizability	24.96 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]+	156.498	30932474
DeepCCS	[M-H]-	154.102	30932474
DeepCCS	[M-2H]-	187.14	30932474
DeepCCS	[M+Na]+	162.483	30932474
AllCCS	[M+H]+	146.5	32859911
AllCCS	[M+H-H2O]+	142.6	32859911
AllCCS	[M+NH4]+	150.1	32859911
AllCCS	[M+Na]+	151.2	32859911
AllCCS	[M-H]-	154.5	32859911
AllCCS	[M+Na-2H]-	155.3	32859911
AllCCS	[M+HCOO]-	156.3	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.	7.7 minutes	32390414
Predicted by Siyang on May 30, 2022	18.1986 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2507.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	602.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	222.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	336.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	152.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	666.9 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	718.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1489.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	546.1 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	1328.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	558.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	381.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	569.4 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one	CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C	1862.7	Standard polar	33892256
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one	CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C	1473.7	Standard non polar	33892256
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one	CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C	1481.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one,1TMS,isomer #1	C=C(O[Si](C)(C)C)/C(C)=C/C1C(C)=CCCC1(C)C	1633.5	Semi standard non polar	33892256
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one,1TMS,isomer #1	C=C(O[Si](C)(C)C)/C(C)=C/C1C(C)=CCCC1(C)C	1619.9	Standard non polar	33892256
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)/C(C)=C/C1C(C)=CCCC1(C)C	1848.6	Semi standard non polar	33892256
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)/C(C)=C/C1C(C)=CCCC1(C)C	1832.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-4900000000-188a75ba35cc10a457d4	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-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 - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 10V, Positive-QTOF	splash10-0a4i-3980000000-aecfe987633b1b3253c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 20V, Positive-QTOF	splash10-05n0-5910000000-d30c3fd0fb817411950b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 40V, Positive-QTOF	splash10-0uxr-9100000000-9b4de8add50fbadeab2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 10V, Negative-QTOF	splash10-0a4i-0190000000-832ea298f97bab583ddc	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 20V, Negative-QTOF	splash10-0bt9-3890000000-f8b94bab666cc1f09e7c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 40V, Negative-QTOF	splash10-02ga-4900000000-aab4a14210d641ae936f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 10V, Negative-QTOF	splash10-0a4i-0490000000-b8904ddd6a4476e42b5f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 20V, Negative-QTOF	splash10-05fr-0930000000-c948347582e5019af52e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 40V, Negative-QTOF	splash10-00l6-9100000000-02cc3f9860c78776dde2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 10V, Positive-QTOF	splash10-000i-1910000000-96bf5af4c798ec733d36	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 20V, Positive-QTOF	splash10-00xr-7900000000-f65ac4d5c7d66a0b1bad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 40V, Positive-QTOF	splash10-05mo-9300000000-1f95634a65fdfd95d3c4	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum

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

FDB008406

KNApSAcK ID

Not Available

Chemspider ID

4522510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5372174

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1023012

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 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (HMDB0031738)

MOL for HMDB0031738 (3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one)

3D MOL for HMDB0031738 (3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one)

3D SDF for HMDB0031738 (3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one)

3D-SDF for HMDB0031738 (3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one)

PDB for HMDB0031738 (3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one)

3D PDB for HMDB0031738 (3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one)

SMILES for HMDB0031738 (3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one)

INCHI for HMDB0031738 (3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one)

Structure for HMDB0031738 (3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one)

3D Structure for HMDB0031738 (3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra