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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:05:38 UTC

Update Date

2023-02-21 17:25:00 UTC

HMDB ID

HMDB0036027

Secondary Accession Numbers

HMDB36027

Metabolite Identification

Common Name

alpha-Damascone

Description

alpha-Damascone, also known as α-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'. alpha-Damascone has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make alpha-damascone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on alpha-Damascone.

Structure

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

HMDB0036027
     RDKit          3D
alpha-Damascone
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.9624    0.2126    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3229   -0.5060   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0342   -0.3995   -0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413    0.3955   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    1.0292    0.8394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121    0.5074   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9117    1.4012    0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2351    2.7464    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711    1.1251    1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592   -0.1870    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858   -0.5612   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -0.7873   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533   -1.3570   -1.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999   -1.8625    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5121   -0.1677    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8262    1.2976    0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0704    0.0444    0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634   -1.1324   -1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6451   -0.9653   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3967    1.0458   -1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    2.7942    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337    3.0052   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0148    3.5428    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414    1.8578    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2294   -0.9539    1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.0977    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1235   -1.4036   -0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858    0.3467   -0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555   -1.6468   -2.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -2.2877   -1.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5767   -0.5532   -2.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -1.4582    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1876   -2.5402   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3644   -2.4847    0.7264 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  1  0
  7  8  1  0
  7  9  2  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
  6 20  1  0
  8 21  1  0
  8 22  1  0
  8 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 05061308512D          

 14 14  0  0  0  0            999 V2000
    3.5724    2.0625    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  2  0  0  0  0
 11  7  1  0  0  0  0
 12 10  1  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>
HMDB0036027

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
CRIGTVCBMUKRSL-ALCCZGGFSA-N

> <FORMULA>
C13H20O

> <MOLECULAR_WEIGHT>
192.2973

> <EXACT_MASS>
192.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.86777022004135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
3.8312158590000003

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.98877009448897

> <JCHEM_PKA_STRONGEST_BASIC>
-4.720307204391163

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
62.14050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036027
     RDKit          3D
alpha-Damascone
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.9624    0.2126    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3229   -0.5060   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0342   -0.3995   -0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413    0.3955   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    1.0292    0.8394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121    0.5074   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9117    1.4012    0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2351    2.7464    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711    1.1251    1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592   -0.1870    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858   -0.5612   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -0.7873   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533   -1.3570   -1.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999   -1.8625    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5121   -0.1677    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8262    1.2976    0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0704    0.0444    0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634   -1.1324   -1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6451   -0.9653   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3967    1.0458   -1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    2.7942    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337    3.0052   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0148    3.5428    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414    1.8578    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2294   -0.9539    1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.0977    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1235   -1.4036   -0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858    0.3467   -0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555   -1.6468   -2.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -2.2877   -1.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5767   -0.5532   -2.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -1.4582    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1876   -2.5402   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3644   -2.4847    0.7264 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  1  0
  7  8  1  0
  7  9  2  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
  6 20  1  0
  8 21  1  0
  8 22  1  0
  8 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       6.668   3.850   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    HMDB0036027
HETATM    1  C1  UNL     1       3.962   0.213   0.397  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.323  -0.506  -0.733  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.034  -0.400  -0.943  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.141   0.395  -0.130  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.612   1.029   0.839  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.312   0.507  -0.377  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.912   1.401   0.630  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.235   2.746   0.792  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.971   1.125   1.384  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.659  -0.187   1.248  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.486  -0.561  -0.221  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.017  -0.787  -0.510  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.953  -1.357  -1.930  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.500  -1.862   0.416  1.00  0.00           C  
HETATM   15  H1  UNL     1       3.512  -0.168   1.343  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.826   1.298   0.279  1.00  0.00           H  
HETATM   17  H3  UNL     1       5.070   0.044   0.398  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.963  -1.132  -1.390  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.645  -0.965  -1.803  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.397   1.046  -1.369  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.363   2.794   1.714  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.334   3.005  -0.112  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.015   3.543   0.897  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.341   1.858   2.106  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.229  -0.954   1.918  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.760  -0.098   1.402  1.00  0.00           H  
HETATM   27  H13 UNL     1      -3.123  -1.404  -0.513  1.00  0.00           H  
HETATM   28  H14 UNL     1      -2.786   0.347  -0.799  1.00  0.00           H  
HETATM   29  H15 UNL     1      -1.956  -1.647  -2.296  1.00  0.00           H  
HETATM   30  H16 UNL     1      -0.341  -2.288  -1.965  1.00  0.00           H  
HETATM   31  H17 UNL     1      -0.577  -0.553  -2.592  1.00  0.00           H  
HETATM   32  H18 UNL     1      -0.039  -1.458   1.325  1.00  0.00           H  
HETATM   33  H19 UNL     1       0.188  -2.540  -0.132  1.00  0.00           H  
HETATM   34  H20 UNL     1      -1.364  -2.485   0.726  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   12   20
CONECT    7    8    9    9
CONECT    8   21   22   23
CONECT    9   10   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

HMDB0036027
     RDKit          3D
alpha-Damascone
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.9624    0.2126    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3229   -0.5060   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0342   -0.3995   -0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413    0.3955   -0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    1.0292    0.8394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121    0.5074   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9117    1.4012    0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2351    2.7464    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711    1.1251    1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592   -0.1870    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858   -0.5612   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -0.7873   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533   -1.3570   -1.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999   -1.8625    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5121   -0.1677    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8262    1.2976    0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0704    0.0444    0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634   -1.1324   -1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6451   -0.9653   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3967    1.0458   -1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    2.7942    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337    3.0052   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0148    3.5428    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414    1.8578    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2294   -0.9539    1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.0977    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1235   -1.4036   -0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858    0.3467   -0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555   -1.6468   -2.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -2.2877   -1.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5767   -0.5532   -2.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -1.4582    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1876   -2.5402   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3644   -2.4847    0.7264 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  1  0
  7  8  1  0
  7  9  2  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
  6 20  1  0
  8 21  1  0
  8 22  1  0
  8 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
a-Damascone	Generator
Α-damascone	Generator
(S)-(e)-(-)-alpha-Damascone	HMDB
Yiyeliangwanoside II	HMDB

Chemical Formula

C₁₃H₂₀O

Average Molecular Weight

192.2973

Monoisotopic Molecular Weight

192.151415262

IUPAC Name

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

Traditional Name

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

CAS Registry Number

116497-11-1

SMILES

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

InChI Identifier

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

InChI Key

CRIGTVCBMUKRSL-ALCCZGGFSA-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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036027)

Source

Endogenous

Endogenous (HMDB: HMDB0036027)

Plant

Plant (HMDB: HMDB0036027)

Exogenous

Food

Food (HMDB: HMDB0036027)

Tea

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036027)

Role

Biological role

Energy storage (HMDB: HMDB0036027)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036027)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	22 - 23 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.095 g/L	ALOGPS
logP	3.96	ALOGPS
logP	3.83	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	18.99	ChemAxon
pKa (Strongest Basic)	-4.7	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	62.14 m³·mol⁻¹	ChemAxon
Polarizability	22.87 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]+	151.039	30932474
DeepCCS	[M-H]-	148.681	30932474
DeepCCS	[M-2H]-	182.752	30932474
DeepCCS	[M+Na]+	157.581	30932474
AllCCS	[M+H]+	142.9	32859911
AllCCS	[M+H-H2O]+	138.8	32859911
AllCCS	[M+NH4]+	146.7	32859911
AllCCS	[M+Na]+	147.8	32859911
AllCCS	[M-H]-	149.5	32859911
AllCCS	[M+Na-2H]-	150.4	32859911
AllCCS	[M+HCOO]-	151.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Damascone	C\C=C/C(=O)C1C(C)=CCCC1(C)C	1699.5	Standard polar	33892256
alpha-Damascone	C\C=C/C(=O)C1C(C)=CCCC1(C)C	1377.1	Standard non polar	33892256
alpha-Damascone	C\C=C/C(=O)C1C(C)=CCCC1(C)C	1392.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-Damascone,1TMS,isomer #1	C/C=C\C(O[Si](C)(C)C)=C1C(C)=CCCC1(C)C	1631.0	Semi standard non polar	33892256
alpha-Damascone,1TMS,isomer #1	C/C=C\C(O[Si](C)(C)C)=C1C(C)=CCCC1(C)C	1601.4	Standard non polar	33892256
alpha-Damascone,1TBDMS,isomer #1	C/C=C\C(O[Si](C)(C)C(C)(C)C)=C1C(C)=CCCC1(C)C	1843.8	Semi standard non polar	33892256
alpha-Damascone,1TBDMS,isomer #1	C/C=C\C(O[Si](C)(C)C(C)(C)C)=C1C(C)=CCCC1(C)C	1842.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Damascone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-8900000000-de5102227103ea957976	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Damascone 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 - alpha-Damascone 10V, Positive-QTOF	splash10-0006-0900000000-04be2f60910d24cad3b5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 20V, Positive-QTOF	splash10-0fr6-7900000000-0e7d098980abfe340bf5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 40V, Positive-QTOF	splash10-014l-9000000000-705ec16a050bcfccc3eb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 10V, Negative-QTOF	splash10-0006-0900000000-b065964df39107b90164	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 20V, Negative-QTOF	splash10-0006-1900000000-b902a32db3daca76ebea	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 40V, Negative-QTOF	splash10-0077-4900000000-e0af3da04ab7018af893	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 10V, Positive-QTOF	splash10-00di-1900000000-f5147216b54fe76ec5ba	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 20V, Positive-QTOF	splash10-00di-3900000000-d95933c7ad26959cc85f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 40V, Positive-QTOF	splash10-0ac0-8900000000-8f82cd64eabe8e1b560c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 10V, Negative-QTOF	splash10-006x-0900000000-63c828647e466d417804	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 20V, Negative-QTOF	splash10-00di-0900000000-ee0f6fcc2e4d3bd7729e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Damascone 40V, Negative-QTOF	splash10-0603-9600000000-a8de1a026b46e479ebd0	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]+)	2023-02-04	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

FDB014845

KNApSAcK ID

C00055711

Chemspider ID

4941175

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6436548

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 alpha-Damascone (HMDB0036027)

MOL for HMDB0036027 (alpha-Damascone)

3D MOL for HMDB0036027 (alpha-Damascone)

3D SDF for HMDB0036027 (alpha-Damascone)

3D-SDF for HMDB0036027 (alpha-Damascone)

PDB for HMDB0036027 (alpha-Damascone)

3D PDB for HMDB0036027 (alpha-Damascone)

SMILES for HMDB0036027 (alpha-Damascone)

INCHI for HMDB0036027 (alpha-Damascone)

Structure for HMDB0036027 (alpha-Damascone)

3D Structure for HMDB0036027 (alpha-Damascone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra