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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 23:24:49 UTC

Update Date

2023-02-21 17:26:22 UTC

HMDB ID

HMDB0038130

Secondary Accession Numbers

HMDB38130

Metabolite Identification

Common Name

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

Description

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

Structure

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

HMDB0038130
     RDKit          3D
1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.0098    0.2560    1.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6712    0.1500    0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6103    0.3580    1.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8945    0.5794    3.1364 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1927    0.3039    1.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8424    0.0771    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971   -0.0040   -0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058   -0.2621   -1.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -0.4325   -2.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9065   -0.3797   -2.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8741    0.6535   -1.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496    1.2080   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    0.1536    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    0.6223    1.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5656   -1.1809    0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9263    0.9820    2.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2977   -0.7545    2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7743    0.6036    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5805   -0.8418    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6588    0.9031    0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567    0.4499    2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -0.0652   -0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4407   -0.6880   -3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389    0.5033   -2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2720   -1.2939   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6880   -0.1605   -3.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3051   -1.4154   -2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300    1.5140   -2.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9225    0.2474   -1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    2.0851   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680    1.5287    0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7103   -0.1329    2.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199    0.8281    1.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    1.6160    1.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9205   -1.4835    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4841   -1.0185   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -2.0053   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  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
  2 19  1  0
  2 20  1  0
  5 21  1  0
  6 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 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 05061310142D          

 15 15  0  0  0  0            999 V2000
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    2.8579    3.3000    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
    2.1434    2.0625    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
    0.0000    0.8250    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    2.4750    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
  5  1  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  2  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038130

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)\C=C\C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O/c1-5-12(15)8-9-13-11(2)7-6-10-14(13,3)4/h8-9H,5-7,10H2,1-4H3/b9-8+

> <INCHI_KEY>
LMWNGLDCJDIIBR-CMDGGOBGSA-N

> <FORMULA>
C14H22O

> <MOLECULAR_WEIGHT>
206.3239

> <EXACT_MASS>
206.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.36091939606324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
3.976159517333334

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.757892467356252

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
66.449

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.09e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038130
     RDKit          3D
1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.0098    0.2560    1.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6712    0.1500    0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6103    0.3580    1.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8945    0.5794    3.1364 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1927    0.3039    1.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8424    0.0771    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971   -0.0040   -0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058   -0.2621   -1.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -0.4325   -2.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9065   -0.3797   -2.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8741    0.6535   -1.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496    1.2080   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    0.1536    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    0.6223    1.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5656   -1.1809    0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9263    0.9820    2.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2977   -0.7545    2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7743    0.6036    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5805   -0.8418    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6588    0.9031    0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567    0.4499    2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -0.0652   -0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4407   -0.6880   -3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389    0.5033   -2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2720   -1.2939   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6880   -0.1605   -3.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3051   -1.4154   -2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300    1.5140   -2.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9225    0.2474   -1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    2.0851   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680    1.5287    0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7103   -0.1329    2.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199    0.8281    1.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    1.6160    1.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9205   -1.4835    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4841   -1.0185   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -2.0053   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  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
  2 19  1  0
  2 20  1  0
  5 21  1  0
  6 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 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       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   6.160   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       4.001   3.850   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   4.620   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    5                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5    1   12                                                       
CONECT    6    7   10                                                       
CONECT    7    6   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10    6   14                                                       
CONECT   11    2    7   13                                                  
CONECT   12    5    8   15                                                  
CONECT   13    9   11   14                                                  
CONECT   14    3    4   10   13                                             
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0038130
HETATM    1  C1  UNL     1       5.010   0.256   1.617  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.671   0.150   0.930  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.610   0.358   1.936  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.895   0.579   3.136  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.193   0.304   1.518  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.842   0.077   0.282  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.497  -0.004  -0.276  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.606  -0.262  -1.609  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.685  -0.432  -2.349  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.906  -0.380  -2.292  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.874   0.654  -1.834  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.550   1.208  -0.473  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.792   0.154   0.366  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.883   0.622   1.769  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.566  -1.181   0.267  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.926   0.982   2.471  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.298  -0.755   2.014  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.774   0.604   0.887  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.581  -0.842   0.426  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.659   0.903   0.124  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.457   0.450   2.261  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.724  -0.065  -0.388  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.441  -0.688  -3.409  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.239   0.503  -2.285  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.272  -1.294  -1.951  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.688  -0.161  -3.389  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.305  -1.415  -2.322  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.830   1.514  -2.531  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.922   0.247  -1.833  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.872   2.085  -0.496  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.468   1.529   0.056  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.710  -0.133   2.553  1.00  0.00           H  
HETATM   33  H18 UNL     1      -3.020   0.828   1.913  1.00  0.00           H  
HETATM   34  H19 UNL     1      -1.459   1.616   1.963  1.00  0.00           H  
HETATM   35  H20 UNL     1      -2.921  -1.484   1.298  1.00  0.00           H  
HETATM   36  H21 UNL     1      -3.484  -1.019  -0.296  1.00  0.00           H  
HETATM   37  H22 UNL     1      -1.924  -2.005  -0.053  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4    4    5
CONECT    5    6    6   21
CONECT    6    7   22
CONECT    7    8    8   13
CONECT    8    9   10
CONECT    9   23   24   25
CONECT   10   11   26   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

HMDB0038130
     RDKit          3D
1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.0098    0.2560    1.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6712    0.1500    0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6103    0.3580    1.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8945    0.5794    3.1364 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1927    0.3039    1.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8424    0.0771    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971   -0.0040   -0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058   -0.2621   -1.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -0.4325   -2.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9065   -0.3797   -2.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8741    0.6535   -1.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496    1.2080   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    0.1536    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    0.6223    1.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5656   -1.1809    0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9263    0.9820    2.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2977   -0.7545    2.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7743    0.6036    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5805   -0.8418    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6588    0.9031    0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567    0.4499    2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -0.0652   -0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4407   -0.6880   -3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389    0.5033   -2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2720   -1.2939   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6880   -0.1605   -3.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3051   -1.4154   -2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300    1.5140   -2.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9225    0.2474   -1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    2.0851   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680    1.5287    0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7103   -0.1329    2.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199    0.8281    1.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    1.6160    1.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9205   -1.4835    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4841   -1.0185   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -2.0053   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  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
  2 19  1  0
  2 20  1  0
  5 21  1  0
  6 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 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
(1E)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one	HMDB
1-Methyl-b-ionone	HMDB
1-Penten-3-one-(2,6,6-trimethyl-1-cyclohen-1-yl)	HMDB
5-(2,6, 6-Trimethyl-1-cyclohexenyl)-4-penten-3-one	HMDB
5-(2,6,6-Trimethyl-1-cyclohexenyl)-4-penten-3-one	HMDB
b-Methylionone	HMDB
beta Methyl ionone	HMDB
beta-Iraldeine	HMDB
beta-Methylionone	HMDB
beta-N-Methyl ionone	HMDB
FEMA 2712	HMDB
Methyl ionone	HMDB
Methyl-beta-ionone	HMDB

Chemical Formula

C₁₄H₂₂O

Average Molecular Weight

206.3239

Monoisotopic Molecular Weight

206.167065326

IUPAC Name

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

Traditional Name

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

CAS Registry Number

127-43-5

SMILES

CCC(=O)\C=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C14H22O/c1-5-12(15)8-9-13-11(2)7-6-10-14(13,3)4/h8-9H,5-7,10H2,1-4H3/b9-8+

InChI Key

LMWNGLDCJDIIBR-CMDGGOBGSA-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

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038130)

Source

Endogenous

Endogenous (HMDB: HMDB0038130)

Animal

Animal (HMDB: HMDB0038130)

Exogenous

Food

Food (HMDB: HMDB0038130)

Exogenous (HMDB: HMDB0038130)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038130)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038130)

Lipid metabolism pathway (HMDB: HMDB0038130)

Cellular process

Cell signaling (HMDB: HMDB0038130)

Biochemical process

Lipid transport (HMDB: HMDB0038130)

Role

Biological role

Energy source (HMDB: HMDB0038130)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038130)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0038130)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	102.00 °C. @ 2.60 mm Hg	The Good Scents Company Information System
Water Solubility	2.58 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.099 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.071 g/L	ALOGPS
logP	4.57	ALOGPS
logP	3.98	ChemAxon
logS	-3.5	ALOGPS
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	3	ChemAxon
Refractivity	66.45 m³·mol⁻¹	ChemAxon
Polarizability	25.36 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]+	158.337	30932474
DeepCCS	[M-H]-	155.979	30932474
DeepCCS	[M-2H]-	189.124	30932474
DeepCCS	[M+Na]+	164.43	30932474
AllCCS	[M+H]+	149.3	32859911
AllCCS	[M+H-H2O]+	145.4	32859911
AllCCS	[M+NH4]+	152.9	32859911
AllCCS	[M+Na]+	154.0	32859911
AllCCS	[M-H]-	156.0	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	158.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one	CCC(=O)\C=C\C1=C(C)CCCC1(C)C	1947.0	Standard polar	33892256
1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one	CCC(=O)\C=C\C1=C(C)CCCC1(C)C	1544.5	Standard non polar	33892256
1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one	CCC(=O)\C=C\C1=C(C)CCCC1(C)C	1562.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one,1TMS,isomer #1	CC=C(/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C	1805.6	Semi standard non polar	33892256
1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one,1TMS,isomer #1	CC=C(/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C	1838.1	Standard non polar	33892256
1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one,1TBDMS,isomer #1	CC=C(/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C	2046.9	Semi standard non polar	33892256
1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one,1TBDMS,isomer #1	CC=C(/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C	2086.1	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-1-cyclohexen-1-yl)-1-penten-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-05rd-2900000000-2c3fd66d96113e6975d9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-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-1-cyclohexen-1-yl)-1-penten-3-one 10V, Positive-QTOF	splash10-0a4i-3790000000-f05a05687fa2b753e5f6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 20V, Positive-QTOF	splash10-052r-8920000000-2595aebd940f6c7cbb88	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 40V, Positive-QTOF	splash10-0gbc-9200000000-2e0973ff04816fa84d06	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 10V, Negative-QTOF	splash10-0a4i-0190000000-a71fb33fa174abd8453b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 20V, Negative-QTOF	splash10-0a4i-4890000000-fcfb683b4a6ddd536e0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 40V, Negative-QTOF	splash10-05n1-4900000000-04e911f4853625891fca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 10V, Positive-QTOF	splash10-052r-2910000000-a96e46811b6775d72c9c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 20V, Positive-QTOF	splash10-00ri-5900000000-15176b392c91a80678fc	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 40V, Positive-QTOF	splash10-0690-9400000000-4f2add9d969d91d166ec	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 10V, Negative-QTOF	splash10-0a4i-0090000000-2d8ac504a1490d38e7ad	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 20V, Negative-QTOF	splash10-052b-1920000000-a1a8c0aa26f243be8009	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one 40V, Negative-QTOF	splash10-0002-5900000000-7941fce13aa965c5d869	2021-09-25	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

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

FDB017357

KNApSAcK ID

C00052093

Chemspider ID

4524757

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5375218

PDB ID

Not Available

ChEBI ID

88921

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1032741

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-1-cyclohexen-1-yl)-1-penten-3-one (HMDB0038130)

MOL for HMDB0038130 (1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one)

3D MOL for HMDB0038130 (1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one)

3D SDF for HMDB0038130 (1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one)

3D-SDF for HMDB0038130 (1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one)

PDB for HMDB0038130 (1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one)

3D PDB for HMDB0038130 (1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one)

SMILES for HMDB0038130 (1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one)

INCHI for HMDB0038130 (1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one)

Structure for HMDB0038130 (1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one)

3D Structure for HMDB0038130 (1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra