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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:09 UTC

Update Date

2022-03-07 02:53:26 UTC

HMDB ID

HMDB0032679

Secondary Accession Numbers

HMDB32679

Metabolite Identification

Common Name

Annuionone A

Description

Annuionone A belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Annuionone A has been detected, but not quantified in, fats and oils and sunflowers (Helianthus annuus). This could make annuionone a a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Annuionone A.

Structure

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

HMDB0032679
     RDKit          3D
Annuionone A
 36 37  0  0  0  0  0  0  0  0999 V2000
    4.7047   -0.1738    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285    0.3818   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992    1.5001   -0.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221   -0.4238    0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399    0.4222    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4066   -0.0840    0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3852    1.0417    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8611    2.3901    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870    0.8617   -1.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817   -0.2929   -1.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8935   -1.0922   -0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -2.3698   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3575   -1.4222   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1168   -0.5644    0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0785   -1.0102    1.1655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    0.8538    0.8165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2798    0.5167    0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6249   -1.1873    0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2044   -0.2539   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -0.6391    1.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1648   -1.3975   -0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1571    1.4278    0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9753    0.7086   -0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -0.4172    1.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    2.4178    1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1491    2.7313   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6787    3.1371    0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330    1.7610   -1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593    0.7909   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754   -3.2222   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357   -2.3625   -1.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3230   -2.7252    0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8160   -1.3655   -1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -2.5103   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4294    1.5495    0.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375    1.0219    1.9066 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 11  6  1  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv0541 02241211562D          

 16 17  0  0  0  0            999 V2000
   -1.7859    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848   -0.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    1.2378    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
  2  7  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  4 15  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6 13  1  0  0  0  0
  6 16  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032679

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CCC1C2(C)COC1(C)CC(=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O3/c1-9(14)4-5-11-12(2)6-10(15)7-13(11,3)16-8-12/h11H,4-8H2,1-3H3

> <INCHI_KEY>
WFJIRKYCKBTOGT-UHFFFAOYSA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.2961

> <EXACT_MASS>
224.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.59849854794941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5-dimethyl-8-(3-oxobutyl)-6-oxabicyclo[3.2.1]octan-3-one

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.2694524119999993

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.625012372954878

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.55645680433328

> <JCHEM_PKA_STRONGEST_BASIC>
-4.172842955372412

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
60.57950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5-dimethyl-8-(3-oxobutyl)-6-oxabicyclo[3.2.1]octan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032679
     RDKit          3D
Annuionone A
 36 37  0  0  0  0  0  0  0  0999 V2000
    4.7047   -0.1738    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285    0.3818   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992    1.5001   -0.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221   -0.4238    0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399    0.4222    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4066   -0.0840    0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3852    1.0417    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8611    2.3901    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870    0.8617   -1.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817   -0.2929   -1.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8935   -1.0922   -0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -2.3698   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3575   -1.4222   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1168   -0.5644    0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0785   -1.0102    1.1655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    0.8538    0.8165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2798    0.5167    0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6249   -1.1873    0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2044   -0.2539   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -0.6391    1.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1648   -1.3975   -0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1571    1.4278    0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9753    0.7086   -0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -0.4172    1.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    2.4178    1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1491    2.7313   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6787    3.1371    0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330    1.7610   -1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593    0.7909   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754   -3.2222   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357   -2.3625   -1.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3230   -2.7252    0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8160   -1.3655   -1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -2.5103   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4294    1.5495    0.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375    1.0219    1.9066 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 11  6  1  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  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      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001  -2.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.671  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.671   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.001   0.768   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.669  -2.311   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.664   0.768   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.999   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.334   0.768   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.669   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.334   2.311   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.772  -0.567   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.001  -1.617   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.664  -2.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.001   2.311   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14   15                                             
CONECT    5    4    6    8                                                  
CONECT    6    1    5   13   16                                             
CONECT    7    2                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    6   14                                                       
CONECT   14    4   13                                                       
CONECT   15    4                                                            
CONECT   16    6                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0032679
HETATM    1  C1  UNL     1       4.705  -0.174   0.078  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.328   0.382  -0.027  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.199   1.500  -0.486  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.122  -0.424   0.426  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.940   0.422   0.181  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.407  -0.084   0.548  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.385   1.042   0.192  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.861   2.390   0.580  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.487   0.862  -1.302  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.782  -0.293  -1.630  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.893  -1.092  -0.461  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.153  -2.370  -0.545  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.357  -1.422  -0.318  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.117  -0.564   0.590  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.079  -1.010   1.166  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.724   0.854   0.817  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.280   0.517   0.723  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.625  -1.187   0.486  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.204  -0.254  -0.916  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.320  -0.639   1.499  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.165  -1.398  -0.081  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.157   1.428   0.667  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.975   0.709  -0.920  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.522  -0.417   1.573  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.377   2.418   1.564  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.149   2.731  -0.199  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.679   3.137   0.613  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.033   1.761  -1.767  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.559   0.791  -1.617  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.875  -3.222  -0.805  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.536  -2.363  -1.418  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.323  -2.725   0.371  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.816  -1.365  -1.325  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.457  -2.510  -0.028  1.00  0.00           H  
HETATM   35  H19 UNL     1      -3.429   1.549   0.363  1.00  0.00           H  
HETATM   36  H20 UNL     1      -2.738   1.022   1.907  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    4
CONECT    4    5   20   21
CONECT    5    6   22   23
CONECT    6    7   11   24
CONECT    7    8    9   16
CONECT    8   25   26   27
CONECT    9   10   28   29
CONECT   10   11
CONECT   11   12   13
CONECT   12   30   31   32
CONECT   13   14   33   34
CONECT   14   15   15   16
CONECT   16   35   36
END

HMDB0032679
     RDKit          3D
Annuionone A
 36 37  0  0  0  0  0  0  0  0999 V2000
    4.7047   -0.1738    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285    0.3818   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992    1.5001   -0.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221   -0.4238    0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399    0.4222    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4066   -0.0840    0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3852    1.0417    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8611    2.3901    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870    0.8617   -1.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817   -0.2929   -1.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8935   -1.0922   -0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -2.3698   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3575   -1.4222   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1168   -0.5644    0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0785   -1.0102    1.1655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    0.8538    0.8165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2798    0.5167    0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6249   -1.1873    0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2044   -0.2539   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3200   -0.6391    1.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1648   -1.3975   -0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1571    1.4278    0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9753    0.7086   -0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -0.4172    1.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    2.4178    1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1491    2.7313   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6787    3.1371    0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330    1.7610   -1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593    0.7909   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8754   -3.2222   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357   -2.3625   -1.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3230   -2.7252    0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8160   -1.3655   -1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -2.5103   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4294    1.5495    0.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375    1.0219    1.9066 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 11  6  1  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Annuionone a	HMDB
5,13-Epoxy-3,9-megastigmanedione	HMDB

Chemical Formula

C₁₃H₂₀O₃

Average Molecular Weight

224.2961

Monoisotopic Molecular Weight

224.141244506

IUPAC Name

1,5-dimethyl-8-(3-oxobutyl)-6-oxabicyclo[3.2.1]octan-3-one

Traditional Name

1,5-dimethyl-8-(3-oxobutyl)-6-oxabicyclo[3.2.1]octan-3-one

CAS Registry Number

201288-96-2

SMILES

CC(=O)CCC1C2(C)COC1(C)CC(=O)C2

InChI Identifier

InChI=1S/C13H20O3/c1-9(14)4-5-11-12(2)6-10(15)7-13(11,3)16-8-12/h11H,4-8H2,1-3H3

InChI Key

WFJIRKYCKBTOGT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Tetrahydrofuran
Cyclic ketone
Ketone
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032679)

Source

Endogenous

Endogenous (HMDB: HMDB0032679)

Plant

Plant (HMDB: HMDB0032679)

Exogenous

Food

Food (HMDB: HMDB0032679)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0032679)

Role

Biological role

Energy source (HMDB: HMDB0032679)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032679)

Emulsifier (HMDB: HMDB0032679)

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	3015 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.52 g/L	ALOGPS
logP	1.39	ALOGPS
logP	1.27	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	18.56	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.58 m³·mol⁻¹	ChemAxon
Polarizability	24.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	150.769	31661259
DarkChem	[M-H]-	147.392	31661259
DeepCCS	[M+H]+	150.604	30932474
DeepCCS	[M-H]-	148.246	30932474
DeepCCS	[M-2H]-	182.215	30932474
DeepCCS	[M+Na]+	157.107	30932474
AllCCS	[M+H]+	151.4	32859911
AllCCS	[M+H-H2O]+	147.7	32859911
AllCCS	[M+NH4]+	154.9	32859911
AllCCS	[M+Na]+	155.9	32859911
AllCCS	[M-H]-	158.0	32859911
AllCCS	[M+Na-2H]-	158.5	32859911
AllCCS	[M+HCOO]-	159.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Annuionone A	CC(=O)CCC1C2(C)COC1(C)CC(=O)C2	2608.0	Standard polar	33892256
Annuionone A	CC(=O)CCC1C2(C)COC1(C)CC(=O)C2	1604.5	Standard non polar	33892256
Annuionone A	CC(=O)CCC1C2(C)COC1(C)CC(=O)C2	1720.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Annuionone A,1TMS,isomer #1	CC(=CCC1C2(C)COC1(C)CC(=O)C2)O[Si](C)(C)C	1858.2	Semi standard non polar	33892256
Annuionone A,1TMS,isomer #1	CC(=CCC1C2(C)COC1(C)CC(=O)C2)O[Si](C)(C)C	1819.5	Standard non polar	33892256
Annuionone A,1TMS,isomer #2	CC(=O)CCC1C2(C)C=C(O[Si](C)(C)C)CC1(C)OC2	1786.7	Semi standard non polar	33892256
Annuionone A,1TMS,isomer #2	CC(=O)CCC1C2(C)C=C(O[Si](C)(C)C)CC1(C)OC2	1699.9	Standard non polar	33892256
Annuionone A,1TMS,isomer #3	CC(=O)CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C)C2	1804.0	Semi standard non polar	33892256
Annuionone A,1TMS,isomer #3	CC(=O)CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C)C2	1705.1	Standard non polar	33892256
Annuionone A,1TMS,isomer #4	C=C(CCC1C2(C)COC1(C)CC(=O)C2)O[Si](C)(C)C	1755.8	Semi standard non polar	33892256
Annuionone A,1TMS,isomer #4	C=C(CCC1C2(C)COC1(C)CC(=O)C2)O[Si](C)(C)C	1838.0	Standard non polar	33892256
Annuionone A,2TMS,isomer #1	CC(=CCC1C2(C)C=C(O[Si](C)(C)C)CC1(C)OC2)O[Si](C)(C)C	1883.2	Semi standard non polar	33892256
Annuionone A,2TMS,isomer #1	CC(=CCC1C2(C)C=C(O[Si](C)(C)C)CC1(C)OC2)O[Si](C)(C)C	1854.7	Standard non polar	33892256
Annuionone A,2TMS,isomer #2	CC(=CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C)C2)O[Si](C)(C)C	1910.8	Semi standard non polar	33892256
Annuionone A,2TMS,isomer #2	CC(=CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C)C2)O[Si](C)(C)C	1853.4	Standard non polar	33892256
Annuionone A,2TMS,isomer #3	C=C(CCC1C2(C)C=C(O[Si](C)(C)C)CC1(C)OC2)O[Si](C)(C)C	1805.3	Semi standard non polar	33892256
Annuionone A,2TMS,isomer #3	C=C(CCC1C2(C)C=C(O[Si](C)(C)C)CC1(C)OC2)O[Si](C)(C)C	1868.7	Standard non polar	33892256
Annuionone A,2TMS,isomer #4	C=C(CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C)C2)O[Si](C)(C)C	1831.7	Semi standard non polar	33892256
Annuionone A,2TMS,isomer #4	C=C(CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C)C2)O[Si](C)(C)C	1876.5	Standard non polar	33892256
Annuionone A,1TBDMS,isomer #1	CC(=CCC1C2(C)COC1(C)CC(=O)C2)O[Si](C)(C)C(C)(C)C	2080.5	Semi standard non polar	33892256
Annuionone A,1TBDMS,isomer #1	CC(=CCC1C2(C)COC1(C)CC(=O)C2)O[Si](C)(C)C(C)(C)C	2070.0	Standard non polar	33892256
Annuionone A,1TBDMS,isomer #2	CC(=O)CCC1C2(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)OC2	2020.9	Semi standard non polar	33892256
Annuionone A,1TBDMS,isomer #2	CC(=O)CCC1C2(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)OC2	1911.3	Standard non polar	33892256
Annuionone A,1TBDMS,isomer #3	CC(=O)CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C(C)(C)C)C2	2033.9	Semi standard non polar	33892256
Annuionone A,1TBDMS,isomer #3	CC(=O)CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C(C)(C)C)C2	1908.8	Standard non polar	33892256
Annuionone A,1TBDMS,isomer #4	C=C(CCC1C2(C)COC1(C)CC(=O)C2)O[Si](C)(C)C(C)(C)C	1983.4	Semi standard non polar	33892256
Annuionone A,1TBDMS,isomer #4	C=C(CCC1C2(C)COC1(C)CC(=O)C2)O[Si](C)(C)C(C)(C)C	2076.8	Standard non polar	33892256
Annuionone A,2TBDMS,isomer #1	CC(=CCC1C2(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)OC2)O[Si](C)(C)C(C)(C)C	2352.3	Semi standard non polar	33892256
Annuionone A,2TBDMS,isomer #1	CC(=CCC1C2(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)OC2)O[Si](C)(C)C(C)(C)C	2286.5	Standard non polar	33892256
Annuionone A,2TBDMS,isomer #2	CC(=CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C(C)(C)C)C2)O[Si](C)(C)C(C)(C)C	2379.9	Semi standard non polar	33892256
Annuionone A,2TBDMS,isomer #2	CC(=CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C(C)(C)C)C2)O[Si](C)(C)C(C)(C)C	2270.3	Standard non polar	33892256
Annuionone A,2TBDMS,isomer #3	C=C(CCC1C2(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)OC2)O[Si](C)(C)C(C)(C)C	2261.2	Semi standard non polar	33892256
Annuionone A,2TBDMS,isomer #3	C=C(CCC1C2(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)OC2)O[Si](C)(C)C(C)(C)C	2269.2	Standard non polar	33892256
Annuionone A,2TBDMS,isomer #4	C=C(CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C(C)(C)C)C2)O[Si](C)(C)C(C)(C)C	2287.9	Semi standard non polar	33892256
Annuionone A,2TBDMS,isomer #4	C=C(CCC1C2(C)COC1(C)C=C(O[Si](C)(C)C(C)(C)C)C2)O[Si](C)(C)C(C)(C)C	2259.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Annuionone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-3910000000-161e113b3cd1300cff11	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annuionone A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annuionone A 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 - Annuionone A 10V, Positive-QTOF	splash10-056r-0290000000-0746b6e7d23999186969	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 20V, Positive-QTOF	splash10-0a6r-3690000000-910e978b17a0a21f8d94	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 40V, Positive-QTOF	splash10-0udu-6900000000-a403605f69601abcd035	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 10V, Negative-QTOF	splash10-00di-0090000000-16e05dcc1c45448fa314	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 20V, Negative-QTOF	splash10-05fr-3290000000-c66eef7900af9e533fe9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 40V, Negative-QTOF	splash10-0a4l-6910000000-6da78e0fe08b734ba50c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 10V, Negative-QTOF	splash10-00di-0090000000-25ff68a3fa868b5c35d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 20V, Negative-QTOF	splash10-00di-2590000000-f02d77e65e74ef37f2fb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 40V, Negative-QTOF	splash10-0a4u-9710000000-0f43fa207a4f5625ad7d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 10V, Positive-QTOF	splash10-004i-0490000000-e8d1ca59cc840f31af09	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 20V, Positive-QTOF	splash10-0570-2960000000-466ac44151ae51ff5e3f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone A 40V, Positive-QTOF	splash10-052o-4920000000-98f8901cb63591a3aefa	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB010634

KNApSAcK ID

C00035806

Chemspider ID

35013465

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72828705

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1830801

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 Annuionone A (HMDB0032679)

MOL for HMDB0032679 (Annuionone A)

3D MOL for HMDB0032679 (Annuionone A)

3D SDF for HMDB0032679 (Annuionone A)

3D-SDF for HMDB0032679 (Annuionone A)

PDB for HMDB0032679 (Annuionone A)

3D PDB for HMDB0032679 (Annuionone A)

SMILES for HMDB0032679 (Annuionone A)

INCHI for HMDB0032679 (Annuionone A)

Structure for HMDB0032679 (Annuionone A)

3D Structure for HMDB0032679 (Annuionone A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra