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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 22:57:17 UTC

Update Date

2021-09-23 22:57:17 UTC

HMDB ID

HMDB0303055

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Oxo-alpha-lonone

Description

3-oxo-alpha-lonone is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. 3-oxo-alpha-lonone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 3-oxo-alpha-lonone can be found in common grape, which makes 3-oxo-alpha-lonone a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303055
     RDKit          3D
3-Oxo-alpha-lonone
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.7420    0.2429   -1.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476   -0.4550   -0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229   -0.9744    0.4937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254   -0.5333    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534    0.0055   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1647   -0.0927    0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7434    1.2219    0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1035    2.5154    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    1.1649    1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5679   -0.1713    1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -0.3931    2.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2956   -1.2635    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902   -0.8033   -0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038    0.1629   -1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359   -1.9601   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435   -0.0220   -1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9579   -0.0975   -2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6825    1.3329   -1.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484   -1.0415    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3326    0.5077   -0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783   -0.6752    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3090    2.8478    1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005    2.5555    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253    3.3349    0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053    2.0364    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380   -2.1523    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2019   -1.5767    0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744    0.7188   -0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    0.8372   -1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2341   -0.3966   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453   -2.4313   -0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830   -1.6926   -2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4390   -2.7524   -1.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  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
  4 19  1  0
  5 20  1  0
  6 21  1  0
  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 02241212582D          

 15 15  0  0  0  0            999 V2000
   -1.2964    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0829    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303055

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)\C=C\C1C(C)=CC(=O)CC1(C)C

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

> <INCHI_KEY>
MLYOGKJJENFVJN-AATRIKPKSA-N

> <FORMULA>
C13H18O2

> <MOLECULAR_WEIGHT>
206.2808

> <EXACT_MASS>
206.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.239639116622982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.499808916

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.341153927760665

> <JCHEM_PKA_STRONGEST_BASIC>
-4.555160106277608

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
62.706799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0303055
     RDKit          3D
3-Oxo-alpha-lonone
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.7420    0.2429   -1.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476   -0.4550   -0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229   -0.9744    0.4937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254   -0.5333    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534    0.0055   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1647   -0.0927    0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7434    1.2219    0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1035    2.5154    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    1.1649    1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5679   -0.1713    1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -0.3931    2.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2956   -1.2635    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902   -0.8033   -0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038    0.1629   -1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359   -1.9601   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435   -0.0220   -1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9579   -0.0975   -2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6825    1.3329   -1.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484   -1.0415    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3326    0.5077   -0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783   -0.6752    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3090    2.8478    1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005    2.5555    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253    3.3349    0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053    2.0364    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380   -2.1523    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2019   -1.5767    0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744    0.7188   -0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    0.8372   -1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2341   -0.3966   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453   -2.4313   -0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830   -1.6926   -2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4390   -2.7524   -1.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  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
  4 19  1  0
  5 20  1  0
  6 21  1  0
  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      -2.420   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.754  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.754  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.420  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.086  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.086  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.087  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.247  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.509   1.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.021   1.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.247   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.581  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.915   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.915   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.248  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6    9   10                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5   11                                                  
CONECT    7    3                                                            
CONECT    8    5                                                            
CONECT    9    1                                                            
CONECT   10    1                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0303055
HETATM    1  C1  UNL     1       3.742   0.243  -1.364  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.548  -0.455  -0.075  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.523  -0.974   0.494  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.225  -0.533   0.523  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.153   0.005  -0.046  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.165  -0.093   0.586  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.743   1.222   0.959  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.104   2.515   0.778  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.952   1.165   1.502  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.568  -0.171   1.669  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.330  -0.393   2.641  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.296  -1.263   0.695  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.190  -0.803  -0.265  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.804   0.163  -1.238  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.636  -1.960  -1.022  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.744  -0.022  -1.797  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.958  -0.098  -2.080  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.682   1.333  -1.163  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.048  -1.042   1.474  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.333   0.508  -0.987  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.078  -0.675   1.528  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.309   2.848   1.768  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.701   2.556   0.039  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.825   3.335   0.494  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.505   2.036   1.827  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.938  -2.152   1.254  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.202  -1.577   0.144  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.674   0.719  -0.812  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.044   0.837  -1.664  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.234  -0.397  -2.118  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.245  -2.431  -0.587  1.00  0.00           H  
HETATM   32  H17 UNL     1      -0.483  -1.693  -2.105  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.439  -2.752  -1.053  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5    5   19
CONECT    5    6   20
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

HMDB0303055
     RDKit          3D
3-Oxo-alpha-lonone
 33 33  0  0  0  0  0  0  0  0999 V2000
    3.7420    0.2429   -1.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476   -0.4550   -0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229   -0.9744    0.4937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254   -0.5333    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534    0.0055   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1647   -0.0927    0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7434    1.2219    0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1035    2.5154    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    1.1649    1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5679   -0.1713    1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -0.3931    2.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2956   -1.2635    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902   -0.8033   -0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038    0.1629   -1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359   -1.9601   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435   -0.0220   -1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9579   -0.0975   -2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6825    1.3329   -1.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484   -1.0415    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3326    0.5077   -0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783   -0.6752    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3090    2.8478    1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005    2.5555    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253    3.3349    0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053    2.0364    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380   -2.1523    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2019   -1.5767    0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744    0.7188   -0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    0.8372   -1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2341   -0.3966   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453   -2.4313   -0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830   -1.6926   -2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4390   -2.7524   -1.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  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
  4 19  1  0
  5 20  1  0
  6 21  1  0
  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
3-oxo-a-Ionone	Generator
3-oxo-Α-ionone	Generator
3-oxo-a-Lonone	Generator
3-oxo-Α-lonone	Generator

Chemical Formula

C₁₃H₁₈O₂

Average Molecular Weight

206.2808

Monoisotopic Molecular Weight

206.13067982

IUPAC Name

3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

Traditional Name

3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

CC(=O)\C=C\C1C(C)=CC(=O)CC1(C)C

InChI Identifier

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

InChI Key

MLYOGKJJENFVJN-AATRIKPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Cyclohexenone
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Cyclic ketone
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0303055)

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	2.16	ALOGPS
logP	2.5	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	19.34	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	62.71 m³·mol⁻¹	ChemAxon
Polarizability	23.24 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]+	146.236	32859911
AllCCS	[M+H-H2O]+	142.274	32859911
AllCCS	[M+Na]+	150.986	32859911
AllCCS	[M+NH4]+	149.923	32859911
AllCCS	[M-H]-	152.163	32859911
AllCCS	[M+Na-2H]-	152.945	32859911
AllCCS	[M+HCOO]-	153.902	32859911
DeepCCS	[M+H]+	152.294	30932474
DeepCCS	[M-H]-	149.899	30932474
DeepCCS	[M-2H]-	183.142	30932474
DeepCCS	[M+Na]+	158.207	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Oxo-alpha-lonone,1TMS,isomer #1	CC(=O)/C=C/C1C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1775.7	Semi standard non polar	33892256
3-Oxo-alpha-lonone,1TMS,isomer #1	CC(=O)/C=C/C1C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1647.9	Standard non polar	33892256
3-Oxo-alpha-lonone,1TMS,isomer #1	CC(=O)/C=C/C1C(C)=CC(O[Si](C)(C)C)=CC1(C)C	2040.6	Standard polar	33892256
3-Oxo-alpha-lonone,1TMS,isomer #2	C=C(/C=C/C1C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C	1852.6	Semi standard non polar	33892256
3-Oxo-alpha-lonone,1TMS,isomer #2	C=C(/C=C/C1C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C	1799.9	Standard non polar	33892256
3-Oxo-alpha-lonone,1TMS,isomer #2	C=C(/C=C/C1C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C	1961.6	Standard polar	33892256
3-Oxo-alpha-lonone,2TMS,isomer #1	C=C(/C=C/C1C(C)=CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	1848.9	Semi standard non polar	33892256
3-Oxo-alpha-lonone,2TMS,isomer #1	C=C(/C=C/C1C(C)=CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	1856.6	Standard non polar	33892256
3-Oxo-alpha-lonone,2TMS,isomer #1	C=C(/C=C/C1C(C)=CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	2033.8	Standard polar	33892256
3-Oxo-alpha-lonone,1TBDMS,isomer #1	CC(=O)/C=C/C1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	2007.5	Semi standard non polar	33892256
3-Oxo-alpha-lonone,1TBDMS,isomer #1	CC(=O)/C=C/C1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	1891.8	Standard non polar	33892256
3-Oxo-alpha-lonone,1TBDMS,isomer #1	CC(=O)/C=C/C1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	2166.3	Standard polar	33892256
3-Oxo-alpha-lonone,1TBDMS,isomer #2	C=C(/C=C/C1C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C(C)(C)C	2068.5	Semi standard non polar	33892256
3-Oxo-alpha-lonone,1TBDMS,isomer #2	C=C(/C=C/C1C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C(C)(C)C	2042.6	Standard non polar	33892256
3-Oxo-alpha-lonone,1TBDMS,isomer #2	C=C(/C=C/C1C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C(C)(C)C	2102.6	Standard polar	33892256
3-Oxo-alpha-lonone,2TBDMS,isomer #1	C=C(/C=C/C1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2284.9	Semi standard non polar	33892256
3-Oxo-alpha-lonone,2TBDMS,isomer #1	C=C(/C=C/C1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2309.9	Standard non polar	33892256
3-Oxo-alpha-lonone,2TBDMS,isomer #1	C=C(/C=C/C1C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2256.2	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 - 3-Oxo-alpha-lonone 10V, Positive-QTOF	splash10-0a4r-0960000000-36e5a40826633286d331	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 20V, Positive-QTOF	splash10-052r-2920000000-d3b5e6389b3520e813d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 40V, Positive-QTOF	splash10-0ab9-5900000000-d2f85f9302cb1f4a774d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 10V, Negative-QTOF	splash10-0a4i-0290000000-996a14212e413d5dc93b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 20V, Negative-QTOF	splash10-0a4i-0790000000-eeef5c813a1f5215f490	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 40V, Negative-QTOF	splash10-000i-3900000000-36568f084bc150620453	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 10V, Positive-QTOF	splash10-05i0-1920000000-6a379e12bec44cca93f5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 20V, Positive-QTOF	splash10-00ei-5900000000-87b04afd70c9d5e1f8fd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 40V, Positive-QTOF	splash10-00dl-9800000000-06ac0734c0af27258cab	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 10V, Negative-QTOF	splash10-0a4i-0090000000-5535f56d1e770e37902d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 20V, Negative-QTOF	splash10-01p9-0910000000-a7ab5c76ebed3ded5763	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-lonone 40V, Negative-QTOF	splash10-0072-1910000000-a803b87d5c0e3f6ef201	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

FDB007536

KNApSAcK ID

Not Available

Chemspider ID

4515999

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5363685

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 3-Oxo-alpha-lonone (HMDB0303055)

MOL for HMDB0303055 (3-Oxo-alpha-lonone)

3D MOL for HMDB0303055 (3-Oxo-alpha-lonone)

3D SDF for HMDB0303055 (3-Oxo-alpha-lonone)

3D-SDF for HMDB0303055 (3-Oxo-alpha-lonone)

PDB for HMDB0303055 (3-Oxo-alpha-lonone)

3D PDB for HMDB0303055 (3-Oxo-alpha-lonone)

SMILES for HMDB0303055 (3-Oxo-alpha-lonone)

INCHI for HMDB0303055 (3-Oxo-alpha-lonone)

Structure for HMDB0303055 (3-Oxo-alpha-lonone)

3D Structure for HMDB0303055 (3-Oxo-alpha-lonone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra