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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 22:56:48 UTC

Update Date

2021-09-23 22:56:49 UTC

HMDB ID

HMDB0303054

Secondary Accession Numbers

None

Metabolite Identification

Common Name

alpha-3-Oxo-damascone

Description

(4S)-4-[(2E)-but-2-enoyl]-3,5,5-trimethylcyclohex-2-en-1-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Based on a literature review very few articles have been published on (4S)-4-[(2E)-but-2-enoyl]-3,5,5-trimethylcyclohex-2-en-1-one.

Structure

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

HMDB0303054
     RDKit          3D
alpha-3-Oxo-damascone
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.1464   -0.7819    0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -0.3941    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2293    0.4581   -0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8360    0.8657   -0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4836    1.7066   -1.7196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1132    0.3039    0.1151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3241   -1.1715   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761   -1.9741   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487   -1.7014    0.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901   -0.8020    1.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -1.2451    3.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0371    0.6138    1.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4541    0.9598    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    2.4594    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    0.4367   -0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -0.6957    1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128   -0.0713   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1899   -1.8083   -0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186   -0.8015    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9220    0.8639   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3623    0.4188    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7406   -1.3187   -1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5318   -2.6008   -1.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379   -2.6476   -0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602   -2.7455    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547    1.2565    2.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139    0.7808    1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339    2.8182    0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0224    2.9549    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7707    2.8189   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863    1.1523   -0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9910    0.4740   -1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.5826   -0.6223 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  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  6 21  1  1
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
M  END

  Mrv0541 02241212562D          

 15 15  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  2  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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  1 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 10 14  2  0  0  0  0
  5 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303054

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C\C(=O)[C@@H]1C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O2/c1-5-6-11(15)12-9(2)7-10(14)8-13(12,3)4/h5-7,12H,8H2,1-4H3/b6-5+/t12-/m0/s1

> <INCHI_KEY>
CATMHDIEBOVJJJ-FYJFLYSWSA-N

> <FORMULA>
C13H18O2

> <MOLECULAR_WEIGHT>
206.2808

> <EXACT_MASS>
206.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.45873276667858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-4-[(2E)-but-2-enoyl]-3,5,5-trimethylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.01174328

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.7148081949903

> <JCHEM_PKA_STRONGEST_BASIC>
-4.586592903053467

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
62.7586

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-[(2E)-but-2-enoyl]-3,5,5-trimethylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0303054
     RDKit          3D
alpha-3-Oxo-damascone
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.1464   -0.7819    0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -0.3941    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2293    0.4581   -0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8360    0.8657   -0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4836    1.7066   -1.7196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1132    0.3039    0.1151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3241   -1.1715   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761   -1.9741   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487   -1.7014    0.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901   -0.8020    1.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -1.2451    3.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0371    0.6138    1.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4541    0.9598    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    2.4594    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    0.4367   -0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -0.6957    1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128   -0.0713   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1899   -1.8083   -0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186   -0.8015    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9220    0.8639   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3623    0.4188    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7406   -1.3187   -1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5318   -2.6008   -1.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379   -2.6476   -0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602   -2.7455    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547    1.2565    2.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139    0.7808    1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339    2.8182    0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0224    2.9549    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7707    2.8189   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863    1.1523   -0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9910    0.4740   -1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.5826   -0.6223 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  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  6 21  1  1
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8    9                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   10                                                            
CONECT   15    5                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0303054
HETATM    1  C1  UNL     1       4.146  -0.782   0.026  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.693  -0.394   0.050  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.229   0.458  -0.826  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.836   0.866  -0.849  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.484   1.707  -1.720  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.113   0.304   0.115  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.324  -1.172  -0.071  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.276  -1.974  -1.139  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.149  -1.701   0.850  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.690  -0.802   1.843  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.872  -1.245   3.008  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.037   0.614   1.543  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.454   0.960   0.164  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.383   2.459   0.097  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.418   0.437  -0.862  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.536  -0.696   1.062  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.713  -0.071  -0.591  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.190  -1.808  -0.356  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.019  -0.801   0.787  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.922   0.864  -1.552  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.362   0.419   1.128  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.741  -1.319  -1.879  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.532  -2.601  -1.577  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.038  -2.648  -0.706  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.360  -2.746   0.804  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.555   1.256   2.304  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.114   0.781   1.562  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.334   2.818   0.191  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.022   2.955   0.874  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.771   2.819  -0.879  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.286   1.152  -0.888  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.991   0.474  -1.889  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.779  -0.583  -0.622  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3   19
CONECT    3    4   20
CONECT    4    5    5    6
CONECT    6    7   13   21
CONECT    7    8    9    9
CONECT    8   22   23   24
CONECT    9   10   25
CONECT   10   11   11   12
CONECT   12   13   26   27
CONECT   13   14   15
CONECT   14   28   29   30
CONECT   15   31   32   33
END

HMDB0303054
     RDKit          3D
alpha-3-Oxo-damascone
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.1464   -0.7819    0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -0.3941    0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2293    0.4581   -0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8360    0.8657   -0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4836    1.7066   -1.7196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1132    0.3039    0.1151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3241   -1.1715   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761   -1.9741   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1487   -1.7014    0.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901   -0.8020    1.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -1.2451    3.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0371    0.6138    1.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4541    0.9598    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    2.4594    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    0.4367   -0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -0.6957    1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128   -0.0713   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1899   -1.8083   -0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186   -0.8015    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9220    0.8639   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3623    0.4188    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7406   -1.3187   -1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5318   -2.6008   -1.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379   -2.6476   -0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3602   -2.7455    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547    1.2565    2.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139    0.7808    1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339    2.8182    0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0224    2.9549    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7707    2.8189   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863    1.1523   -0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9910    0.4740   -1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.5826   -0.6223 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  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  6 21  1  1
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-3-oxo-Damascone	Generator
Α-3-oxo-damascone	Generator

Chemical Formula

C₁₃H₁₈O₂

Average Molecular Weight

206.2808

Monoisotopic Molecular Weight

206.13067982

IUPAC Name

(4S)-4-[(2E)-but-2-enoyl]-3,5,5-trimethylcyclohex-2-en-1-one

Traditional Name

(4S)-4-[(2E)-but-2-enoyl]-3,5,5-trimethylcyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

C\C=C\C(=O)[C@@H]1C(C)=CC(=O)CC1(C)C

InChI Identifier

InChI=1S/C13H18O2/c1-5-6-11(15)12-9(2)7-10(14)8-13(12,3)4/h5-7,12H,8H2,1-4H3/b6-5+/t12-/m0/s1

InChI Key

CATMHDIEBOVJJJ-FYJFLYSWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0303054)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

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	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
logP	3.05	ALOGPS
logP	3.01	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	16.71	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.76 m³·mol⁻¹	ChemAxon
Polarizability	23.46 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
AllCCS	[M+H]+	146.185	32859911
AllCCS	[M+H-H2O]+	142.217	32859911
AllCCS	[M+Na]+	150.94	32859911
AllCCS	[M+NH4]+	149.876	32859911
AllCCS	[M-H]-	152.054	32859911
AllCCS	[M+Na-2H]-	152.807	32859911
AllCCS	[M+HCOO]-	153.731	32859911
DeepCCS	[M+H]+	159.013	30932474
DeepCCS	[M-H]-	156.655	30932474
DeepCCS	[M-2H]-	189.541	30932474
DeepCCS	[M+Na]+	165.106	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-3-Oxo-damascone,1TMS,isomer #1	C/C=C/C(O[Si](C)(C)C)=C1C(C)=CC(=O)CC1(C)C	1863.7	Semi standard non polar	33892256
alpha-3-Oxo-damascone,1TMS,isomer #1	C/C=C/C(O[Si](C)(C)C)=C1C(C)=CC(=O)CC1(C)C	1733.0	Standard non polar	33892256
alpha-3-Oxo-damascone,1TMS,isomer #1	C/C=C/C(O[Si](C)(C)C)=C1C(C)=CC(=O)CC1(C)C	1879.5	Standard polar	33892256
alpha-3-Oxo-damascone,1TMS,isomer #2	C/C=C/C(=O)[C@@H]1C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1730.8	Semi standard non polar	33892256
alpha-3-Oxo-damascone,1TMS,isomer #2	C/C=C/C(=O)[C@@H]1C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1649.8	Standard non polar	33892256
alpha-3-Oxo-damascone,1TMS,isomer #2	C/C=C/C(=O)[C@@H]1C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1951.6	Standard polar	33892256
alpha-3-Oxo-damascone,2TMS,isomer #1	C/C=C/C(O[Si](C)(C)C)=C1C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1881.2	Semi standard non polar	33892256
alpha-3-Oxo-damascone,2TMS,isomer #1	C/C=C/C(O[Si](C)(C)C)=C1C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1865.0	Standard non polar	33892256
alpha-3-Oxo-damascone,2TMS,isomer #1	C/C=C/C(O[Si](C)(C)C)=C1C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1926.9	Standard polar	33892256
alpha-3-Oxo-damascone,1TBDMS,isomer #1	C/C=C/C(O[Si](C)(C)C(C)(C)C)=C1C(C)=CC(=O)CC1(C)C	2061.2	Semi standard non polar	33892256
alpha-3-Oxo-damascone,1TBDMS,isomer #1	C/C=C/C(O[Si](C)(C)C(C)(C)C)=C1C(C)=CC(=O)CC1(C)C	1980.3	Standard non polar	33892256
alpha-3-Oxo-damascone,1TBDMS,isomer #1	C/C=C/C(O[Si](C)(C)C(C)(C)C)=C1C(C)=CC(=O)CC1(C)C	2023.5	Standard polar	33892256
alpha-3-Oxo-damascone,1TBDMS,isomer #2	C/C=C/C(=O)[C@@H]1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	1947.5	Semi standard non polar	33892256
alpha-3-Oxo-damascone,1TBDMS,isomer #2	C/C=C/C(=O)[C@@H]1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	1888.9	Standard non polar	33892256
alpha-3-Oxo-damascone,1TBDMS,isomer #2	C/C=C/C(=O)[C@@H]1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	2075.7	Standard polar	33892256
alpha-3-Oxo-damascone,2TBDMS,isomer #1	C/C=C/C(O[Si](C)(C)C(C)(C)C)=C1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	2264.5	Semi standard non polar	33892256
alpha-3-Oxo-damascone,2TBDMS,isomer #1	C/C=C/C(O[Si](C)(C)C(C)(C)C)=C1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	2332.1	Standard non polar	33892256
alpha-3-Oxo-damascone,2TBDMS,isomer #1	C/C=C/C(O[Si](C)(C)C(C)(C)C)=C1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	2145.7	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 10V, Positive-QTOF	splash10-0a4i-1490000000-d79a10a9f4b7d680608c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 20V, Positive-QTOF	splash10-0aor-4930000000-846f815f63daac9daf54	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 40V, Positive-QTOF	splash10-0006-9400000000-4af5540e7347d1b060c4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 10V, Negative-QTOF	splash10-0a4i-0290000000-853fb9b5227937ceb5b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 20V, Negative-QTOF	splash10-0a4i-3590000000-d85fd5080a3bddec4005	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 40V, Negative-QTOF	splash10-0016-9700000000-a52ffae90e8206745678	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 10V, Positive-QTOF	splash10-052r-1930000000-2423fb2559efd625fe6f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 20V, Positive-QTOF	splash10-001r-9810000000-0d317324939b81402093	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 40V, Positive-QTOF	splash10-000t-8900000000-e5614f67692aaf6815ea	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 10V, Negative-QTOF	splash10-000i-0930000000-ee56cbcac45b24aa2b4f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 20V, Negative-QTOF	splash10-000i-0900000000-2a4da48e3f57fef68642	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-3-Oxo-damascone 40V, Negative-QTOF	splash10-00xs-8900000000-8754c66d0f3125d9e02f	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB007535

KNApSAcK ID

Not Available

Chemspider ID

59696437

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for alpha-3-Oxo-damascone (HMDB0303054)

MOL for HMDB0303054 (alpha-3-Oxo-damascone)

3D MOL for HMDB0303054 (alpha-3-Oxo-damascone)

3D SDF for HMDB0303054 (alpha-3-Oxo-damascone)

3D-SDF for HMDB0303054 (alpha-3-Oxo-damascone)

PDB for HMDB0303054 (alpha-3-Oxo-damascone)

3D PDB for HMDB0303054 (alpha-3-Oxo-damascone)

SMILES for HMDB0303054 (alpha-3-Oxo-damascone)

INCHI for HMDB0303054 (alpha-3-Oxo-damascone)

Structure for HMDB0303054 (alpha-3-Oxo-damascone)

3D Structure for HMDB0303054 (alpha-3-Oxo-damascone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra