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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:22 UTC

Update Date

2023-02-21 17:22:19 UTC

HMDB ID

HMDB0032541

Secondary Accession Numbers

HMDB32541

Metabolite Identification

Common Name

4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one

Description

4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one, also known as damascone, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one is a blackcurrant, floral, and fruity tasting compound. Based on a literature review a significant number of articles have been published on 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one.

Structure

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

HMDB0032541
     RDKit          3D
4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.9200    0.1520    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -0.5260    0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    0.1516    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1721   -0.4769    0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676   -1.7552    0.4944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1642   -0.0301    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5517    1.1887   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4856    2.2625   -0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9586    1.6258   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0176    0.7026   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814   -0.3117    0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276   -0.9946    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -2.2391    0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -1.3383   -1.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6120   -0.1596    1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209    1.2637    0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3905   -0.0554   -0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632   -1.5707    0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6184    1.1704   -0.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555    2.5130    0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    3.2264   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169    2.1196   -1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    1.8061   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    2.6486   -0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7810    1.2962    0.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5983    0.2379   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174    0.2442    1.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2027   -1.0924    1.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5426   -3.0462    0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156   -2.6417    1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4940   -1.9869    1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104   -0.5148   -1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8703   -1.6444   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412   -2.2253   -1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END


  Mrv0541 05061309122D          

 14 14  0  0  0  0            999 V2000
    2.8579    3.3000    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    2.4750    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
    2.1434    2.0625    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
    1.4289    0.0000    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    0.8250    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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032541

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5,7H,6,8-9H2,1-4H3/b7-5+

> <INCHI_KEY>
BGTBFNDXYDYBEY-FNORWQNLSA-N

> <FORMULA>
C13H20O

> <MOLECULAR_WEIGHT>
192.2973

> <EXACT_MASS>
192.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.31577956537342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.20

> <JCHEM_LOGP>
4.043525216333334

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.253767276711182

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
61.899800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
damascone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032541
     RDKit          3D
4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.9200    0.1520    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -0.5260    0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    0.1516    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1721   -0.4769    0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676   -1.7552    0.4944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1642   -0.0301    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5517    1.1887   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4856    2.2625   -0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9586    1.6258   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0176    0.7026   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814   -0.3117    0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276   -0.9946    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -2.2391    0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -1.3383   -1.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6120   -0.1596    1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209    1.2637    0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3905   -0.0554   -0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632   -1.5707    0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6184    1.1704   -0.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555    2.5130    0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    3.2264   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169    2.1196   -1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    1.8061   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    2.6486   -0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7810    1.2962    0.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5983    0.2379   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174    0.2442    1.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2027   -1.0924    1.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5426   -3.0462    0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156   -2.6417    1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4940   -1.9869    1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104   -0.5148   -1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8703   -1.6444   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412   -2.2253   -1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END

HEADER    PROTEIN                                 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       5.335   6.160   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   4.620   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       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   10                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5    1    7                                                       
CONECT    6    8    9                                                       
CONECT    7    5   11                                                       
CONECT    8    6   10                                                       
CONECT    9    6   13                                                       
CONECT   10    2    8   12                                                  
CONECT   11    7   12   14                                                  
CONECT   12   10   11   13                                                  
CONECT   13    3    4    9   12                                             
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0032541
HETATM    1  C1  UNL     1       4.920   0.152   0.316  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.602  -0.526   0.378  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.449   0.152   0.146  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.172  -0.477   0.199  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.268  -1.755   0.494  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.164  -0.030   0.004  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.552   1.189  -0.313  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.486   2.262  -0.498  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.959   1.626  -0.529  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.018   0.703  -0.098  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.481  -0.312   0.883  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.328  -0.995   0.165  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.992  -2.239   0.910  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.791  -1.338  -1.223  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.612  -0.160   1.102  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.821   1.264   0.365  1.00  0.00           H  
HETATM   17  H3  UNL     1       5.390  -0.055  -0.673  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.563  -1.571   0.610  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.618   1.170  -0.071  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.955   2.513   0.465  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.084   3.226  -0.751  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.117   2.120  -1.367  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.058   1.806  -1.634  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.074   2.649  -0.073  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.781   1.296   0.487  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.598   0.238  -0.932  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.117   0.244   1.760  1.00  0.00           H  
HETATM   28  H14 UNL     1      -3.203  -1.092   1.140  1.00  0.00           H  
HETATM   29  H15 UNL     1      -0.543  -3.046   0.318  1.00  0.00           H  
HETATM   30  H16 UNL     1      -2.016  -2.642   1.256  1.00  0.00           H  
HETATM   31  H17 UNL     1      -0.494  -1.987   1.856  1.00  0.00           H  
HETATM   32  H18 UNL     1      -1.610  -0.515  -1.918  1.00  0.00           H  
HETATM   33  H19 UNL     1      -2.870  -1.644  -1.145  1.00  0.00           H  
HETATM   34  H20 UNL     1      -1.241  -2.225  -1.633  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3   18
CONECT    3    4   19
CONECT    4    5    5    6
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    8   20   21   22
CONECT    9   10   23   24
CONECT   10   11   25   26
CONECT   11   12   27   28
CONECT   12   13   14
CONECT   13   29   30   31
CONECT   14   32   33   34
END

HMDB0032541
     RDKit          3D
4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.9200    0.1520    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -0.5260    0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    0.1516    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1721   -0.4769    0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676   -1.7552    0.4944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1642   -0.0301    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5517    1.1887   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4856    2.2625   -0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9586    1.6258   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0176    0.7026   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814   -0.3117    0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276   -0.9946    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -2.2391    0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -1.3383   -1.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6120   -0.1596    1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209    1.2637    0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3905   -0.0554   -0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632   -1.5707    0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6184    1.1704   -0.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555    2.5130    0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    3.2264   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169    2.1196   -1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    1.8061   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    2.6486   -0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7810    1.2962    0.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5983    0.2379   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174    0.2442    1.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2027   -1.0924    1.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5426   -3.0462    0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156   -2.6417    1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4940   -1.9869    1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104   -0.5148   -1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8703   -1.6444   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412   -2.2253   -1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Damascone	HMDB
alpha-Damascone	HMDB

Chemical Formula

C₁₃H₂₀O

Average Molecular Weight

192.2973

Monoisotopic Molecular Weight

192.151415262

IUPAC Name

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

Traditional Name

damascone

CAS Registry Number

35044-68-9

SMILES

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

InChI Identifier

InChI=1S/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5,7H,6,8-9H2,1-4H3/b7-5+

InChI Key

BGTBFNDXYDYBEY-FNORWQNLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Enone
Acryloyl-group
Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0032541)

Food

Fruit

Berry

Red raspberry (FooDB: FOOD00162)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	200.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	7.99 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.312 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	4.2	ALOGPS
logP	4.04	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.9 m³·mol⁻¹	ChemAxon
Polarizability	23.32 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]+	156.987	30932474
DeepCCS	[M-H]-	154.629	30932474
DeepCCS	[M-2H]-	188.729	30932474
DeepCCS	[M+Na]+	163.667	30932474
AllCCS	[M+H]+	143.6	32859911
AllCCS	[M+H-H2O]+	139.6	32859911
AllCCS	[M+NH4]+	147.4	32859911
AllCCS	[M+Na]+	148.5	32859911
AllCCS	[M-H]-	150.2	32859911
AllCCS	[M+Na-2H]-	151.2	32859911
AllCCS	[M+HCOO]-	152.4	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.	7.91 minutes	32390414
Predicted by Siyang on May 30, 2022	17.7192 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.06 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2463.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	579.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	220.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	343.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	691.1 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	791.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1460.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	525.2 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	1497.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	493.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	429.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	453.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	595.2 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one	C\C=C\C(=O)C1=C(C)CCCC1(C)C	1833.0	Standard polar	33892256
4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one	C\C=C\C(=O)C1=C(C)CCCC1(C)C	1402.6	Standard non polar	33892256
4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one	C\C=C\C(=O)C1=C(C)CCCC1(C)C	1389.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gkc-4900000000-f43a30febb042e2a67c2	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-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 - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 10V, Positive-QTOF	splash10-0006-1900000000-f4246e1a7a0324097f17	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 20V, Positive-QTOF	splash10-0fr6-7900000000-64f2890bef8111d8879e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 40V, Positive-QTOF	splash10-014l-9200000000-cd02edb59297970b0667	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 10V, Negative-QTOF	splash10-0006-0900000000-7aa0b052ddabf7a4ce02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 20V, Negative-QTOF	splash10-0006-2900000000-3fcb681c59ac29a57e7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 40V, Negative-QTOF	splash10-0kg7-4900000000-4dd3757fd6b10276e71a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 10V, Negative-QTOF	splash10-0006-0900000000-3fd2c06baba7e6049d2f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 20V, Negative-QTOF	splash10-00di-0900000000-1d8e8b890d12d7183795	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 40V, Negative-QTOF	splash10-00di-8900000000-5ce7f14d11529753693a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 10V, Positive-QTOF	splash10-01bc-0900000000-bc6e2f8dcbaa2f10a5e9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 20V, Positive-QTOF	splash10-00fr-2900000000-8d3a7447fec3cb667010	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one 40V, Positive-QTOF	splash10-05gl-8900000000-caab6f92a3aee373a59b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

IR Spectra

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

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010416

KNApSAcK ID

Not Available

Chemspider ID

4524302

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5374527

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1445672

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one (HMDB0032541)

MOL for HMDB0032541 (4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one)

3D MOL for HMDB0032541 (4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one)

3D SDF for HMDB0032541 (4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one)

3D-SDF for HMDB0032541 (4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one)

PDB for HMDB0032541 (4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one)

3D PDB for HMDB0032541 (4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one)

SMILES for HMDB0032541 (4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one)

INCHI for HMDB0032541 (4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one)

Structure for HMDB0032541 (4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one)

3D Structure for HMDB0032541 (4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra