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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-05-18 14:36:00 UTC

Update Date

2023-02-21 17:18:03 UTC

HMDB ID

HMDB0013804

Secondary Accession Numbers

HMDB13804

Metabolite Identification

Common Name

beta-Damascenone

Description

beta-Damascenone, also known as damascenone, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Thus, beta-damascenone is considered to be an isoprenoid. beta-Damascenone exists in all eukaryotes, ranging from yeast to plants to humans. beta-Damascenone is a sweet, apple, and apple.rose tasting compound. beta-Damascenone is found, on average, in the highest concentration within red wine. beta-Damascenone has also been detected, but not quantified in, several different foods, such as german camomiles (Matricaria recutita), common grapes (Vitis vinifera), apples (Malus pumila), garden tomatoes (Solanum lycopersicum), and grapes (Vitis). This could make beta-damascenone a potential biomarker for the consumption of these foods. beta-Damascenone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on beta-Damascenone.

Structure

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

HMDB0036572
     RDKit          3D
3,5,8-Megastigmatrien-7-one
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.5375   -0.4749   -0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2268    0.2137   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559   -0.3275   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822    0.2852   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8671    1.4046   -1.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3951   -0.0766    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067   -1.1409    0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880   -2.1244    1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9048   -1.4125    1.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9187   -0.6141    1.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7868    0.6196    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509    0.8665   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7714    0.7188   -1.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1029    2.2961    0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4420   -1.5710   -0.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1183   -0.0347   -0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -0.2105   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0586    1.1260   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4368   -1.2406    0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038   -2.9376    1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2538   -1.7203    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -2.6717    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0617   -2.3354    2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019   -0.8643    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6909    0.6841   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    1.4614    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650    0.9019   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    1.4944   -2.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -0.3172   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9189    2.8319    0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9491    2.8492   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317    2.3209    0.7615 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
M  END

damascenone
  Mrv1652303102016532D          

 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
    2.8579    2.4750    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
    2.8579    0.8250    0.0000 O   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
    1.4289    0.0000    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
    0.7145   -0.4125    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
    0.0000    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
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013804

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C\C(=O)C1=C(C)C=CCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+

> <INCHI_KEY>
POIARNZEYGURDG-FNORWQNLSA-N

> <FORMULA>
C13H18O

> <MOLECULAR_WEIGHT>
190.286

> <EXACT_MASS>
190.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.606738542802788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.6816035596666667

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.246642868703947

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
63.01640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
damascenone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036572
     RDKit          3D
3,5,8-Megastigmatrien-7-one
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.5375   -0.4749   -0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2268    0.2137   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559   -0.3275   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822    0.2852   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8671    1.4046   -1.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3951   -0.0766    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067   -1.1409    0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880   -2.1244    1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9048   -1.4125    1.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9187   -0.6141    1.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7868    0.6196    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509    0.8665   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7714    0.7188   -1.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1029    2.2961    0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4420   -1.5710   -0.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1183   -0.0347   -0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -0.2105   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0586    1.1260   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4368   -1.2406    0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038   -2.9376    1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2538   -1.7203    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -2.6717    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0617   -2.3354    2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019   -0.8643    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6909    0.6841   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    1.4614    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650    0.9019   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    1.4944   -2.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -0.3172   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9189    2.8319    0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9491    2.8492   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317    2.3209    0.7615 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: damascenone                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0036572
HETATM    1  C1  UNL     1       4.538  -0.475  -0.913  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.227   0.214  -0.986  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.156  -0.328  -0.350  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.882   0.285  -0.385  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.867   1.405  -1.084  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.395  -0.077   0.193  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.607  -1.141   0.917  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.488  -2.124   1.222  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.905  -1.413   1.509  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.919  -0.614   1.356  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.787   0.620   0.566  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.551   0.866  -0.133  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.771   0.719  -1.647  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.103   2.296   0.087  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.442  -1.571  -0.820  1.00  0.00           H  
HETATM   16  H2  UNL     1       5.118  -0.035  -0.077  1.00  0.00           H  
HETATM   17  H3  UNL     1       5.110  -0.210  -1.841  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.059   1.126  -1.514  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.437  -1.241   0.150  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.004  -2.938   1.854  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.254  -1.720   1.901  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.843  -2.672   0.355  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.062  -2.335   2.121  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.902  -0.864   1.829  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.691   0.684  -0.145  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.055   1.461   1.304  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.865   0.902  -1.841  1.00  0.00           H  
HETATM   28  H14 UNL     1      -1.192   1.494  -2.170  1.00  0.00           H  
HETATM   29  H15 UNL     1      -1.513  -0.317  -1.966  1.00  0.00           H  
HETATM   30  H16 UNL     1      -1.919   2.832   0.608  1.00  0.00           H  
HETATM   31  H17 UNL     1      -0.949   2.849  -0.864  1.00  0.00           H  
HETATM   32  H18 UNL     1      -0.232   2.321   0.762  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   10   23
CONECT   10   11   24
CONECT   11   12   25   26
CONECT   12   13   14
CONECT   13   27   28   29
CONECT   14   30   31   32
END

HMDB0036572
     RDKit          3D
3,5,8-Megastigmatrien-7-one
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.5375   -0.4749   -0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2268    0.2137   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559   -0.3275   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822    0.2852   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8671    1.4046   -1.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3951   -0.0766    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067   -1.1409    0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880   -2.1244    1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9048   -1.4125    1.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9187   -0.6141    1.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7868    0.6196    0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509    0.8665   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7714    0.7188   -1.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1029    2.2961    0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4420   -1.5710   -0.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1183   -0.0347   -0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -0.2105   -1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0586    1.1260   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4368   -1.2406    0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038   -2.9376    1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2538   -1.7203    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -2.6717    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0617   -2.3354    2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019   -0.8643    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6909    0.6841   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    1.4614    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650    0.9019   -1.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    1.4944   -2.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -0.3172   -1.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9189    2.8319    0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9491    2.8492   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317    2.3209    0.7615 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one	ChEBI
(e)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one	ChEBI
(e)-beta-Damascenone	ChEBI
beta-(e)-Damascenone	ChEBI
Damascenone	ChEBI
trans-beta-Damascenone	ChEBI
trans-Damascenone	ChEBI
(e)-b-Damascenone	Generator
(e)-Β-damascenone	Generator
b-(e)-Damascenone	Generator
Β-(e)-damascenone	Generator
trans-b-Damascenone	Generator
trans-Β-damascenone	Generator
b-Damascenone	Generator
Β-damascenone	Generator
1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one	HMDB

Chemical Formula

C₁₃H₁₈O

Average Molecular Weight

190.286

Monoisotopic Molecular Weight

190.1357652

IUPAC Name

(2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one

Traditional Name

damascenone

CAS Registry Number

23696-85-7

SMILES

C\C=C\C(=O)C1=C(C)C=CCC1(C)C

InChI Identifier

InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+

InChI Key

POIARNZEYGURDG-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

enone (CHEBI:67251 )
apo carotenoid monoterpenoid (CHEBI:67251 )
cyclic monoterpene ketone (CHEBI:67251 )
C40 isoprenoids (tetraterpenes) (LMPR01070304 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0013804)

Excreta

Biofluid or Excreta

Urine (PMID: 22284503)

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	274.00 to 276.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	12.48 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.042 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	4.02	ALOGPS
logP	3.68	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-4.2	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	63.02 m³·mol⁻¹	ChemAxon
Polarizability	22.61 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]+	153.583	30932474
DeepCCS	[M-H]-	151.225	30932474
DeepCCS	[M-2H]-	184.547	30932474
DeepCCS	[M+Na]+	159.676	30932474
AllCCS	[M+H]+	141.0	32859911
AllCCS	[M+H-H2O]+	136.8	32859911
AllCCS	[M+NH4]+	144.9	32859911
AllCCS	[M+Na]+	146.0	32859911
AllCCS	[M-H]-	146.9	32859911
AllCCS	[M+Na-2H]-	147.7	32859911
AllCCS	[M+HCOO]-	148.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Damascenone	C\C=C\C(=O)C1=C(C)C=CCC1(C)C	1800.4	Standard polar	33892256
beta-Damascenone	C\C=C\C(=O)C1=C(C)C=CCC1(C)C	1388.6	Standard non polar	33892256
beta-Damascenone	C\C=C\C(=O)C1=C(C)C=CCC1(C)C	1374.2	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 - beta-Damascenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01dm-5900000000-4bcd624fdf9c5e42b887	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Damascenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Damascenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Damascenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Damascenone 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 - beta-Damascenone 10V, Positive-QTOF	splash10-0006-1900000000-8da6e151fea92abe412a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 20V, Positive-QTOF	splash10-00kg-6900000000-2069d91b82e6511da0ae	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 40V, Positive-QTOF	splash10-014l-9200000000-6695f41d1b443f4da598	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 10V, Negative-QTOF	splash10-000i-0900000000-3f94da9b260ed91041b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 20V, Negative-QTOF	splash10-000i-2900000000-7afc8b9366085d67da73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 40V, Negative-QTOF	splash10-007n-4900000000-d38de494cceadf7b6a17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 10V, Negative-QTOF	splash10-000i-0900000000-797743ba698bddb677b1	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 20V, Negative-QTOF	splash10-00di-0900000000-d9210597b39735810ebf	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 40V, Negative-QTOF	splash10-0ab9-2900000000-4ac82453126eb07d119f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 10V, Positive-QTOF	splash10-022c-0900000000-3c6a17c1864038197fc5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 20V, Positive-QTOF	splash10-05fr-2900000000-7fc87120284ef620e86a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Damascenone 40V, Positive-QTOF	splash10-0ac0-7900000000-3e0424c46a79abc4667d	2021-09-24	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Breast cancer	22284503	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015480

KNApSAcK ID

C00035536

Chemspider ID

4517997

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Damascenone

METLIN ID

Not Available

PubChem Compound

5366074

PDB ID

Not Available

ChEBI ID

67251

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1441071

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for beta-Damascenone (HMDB0013804)

MOL for HMDB0013804 (beta-Damascenone)

3D MOL for HMDB0013804 (beta-Damascenone)

3D SDF for HMDB0013804 (beta-Damascenone)

3D-SDF for HMDB0013804 (beta-Damascenone)

PDB for HMDB0013804 (beta-Damascenone)

3D PDB for HMDB0013804 (beta-Damascenone)

SMILES for HMDB0013804 (beta-Damascenone)

INCHI for HMDB0013804 (beta-Damascenone)

Structure for HMDB0013804 (beta-Damascenone)

3D Structure for HMDB0013804 (beta-Damascenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra