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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:02:04 UTC

Update Date

2022-03-07 02:55:30 UTC

HMDB ID

HMDB0037776

Secondary Accession Numbers

HMDB37776

Metabolite Identification

Common Name

5,9:6,9-Diepoxy-3-megastigmene

Description

5,9:6,9-Diepoxy-3-megastigmene belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. 5,9:6,9-Diepoxy-3-megastigmene has been detected, but not quantified in, alcoholic beverages and fruits. This could make 5,9:6,9-diepoxy-3-megastigmene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,9:6,9-Diepoxy-3-megastigmene.

Structure

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

HMDB0037776
     RDKit          3D
5,9:6,9-Diepoxy-3-megastigmene
 35 37  0  0  0  0  0  0  0  0999 V2000
    2.9805   -0.7905    1.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440   -0.3515    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0204   -1.0448   -0.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996   -0.7867   -1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351   -0.1303   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414   -0.7762    0.8779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854   -0.3681    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407   -1.8608    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3207   -0.0883   -1.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9815    0.3406    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3477    1.6052    1.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346    2.0423    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    1.2466   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5595    2.0652   -1.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871    1.0144    0.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5064   -0.9119    2.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -0.1072    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -1.8148    1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7812   -0.6386   -1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0916   -2.1229   -0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -1.7397   -1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6739   -0.1952   -2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158   -2.0882    0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276   -2.2659    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -2.4169   -0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3250   -0.5397   -1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034    0.9624   -1.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8937   -0.6655   -2.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8824   -0.3304    2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0829    0.4980    1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294    2.2256    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805    2.9960    1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9239    3.0847   -0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3580    1.7015   -1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997    2.2517   -1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  6  2  1  0
 15  2  1  0
 13  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
M  END


  Mrv0541 02241214222D          

 15 17  0  0  0  0            999 V2000
    1.1141    0.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884    1.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534    0.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6091   -1.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0316   -0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -1.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7741    0.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    0.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309   -0.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2059   -0.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037776

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3(O1)C(C)(O2)C=CCC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O2/c1-10(2)6-5-7-11(3)13(10)9-8-12(4,14-11)15-13/h5,7H,6,8-9H2,1-4H3

> <INCHI_KEY>
QXHORPLJTIHQGR-UHFFFAOYSA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.68911048904984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2,6,8-tetramethyl-7,11-dioxatricyclo[6.2.1.0¹,⁶]undec-4-ene

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
2.8128595783333337

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.112339254337954

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
59.941300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,6,8-tetramethyl-7,11-dioxatricyclo[6.2.1.0¹,⁶]undec-4-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037776
     RDKit          3D
5,9:6,9-Diepoxy-3-megastigmene
 35 37  0  0  0  0  0  0  0  0999 V2000
    2.9805   -0.7905    1.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440   -0.3515    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0204   -1.0448   -0.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996   -0.7867   -1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351   -0.1303   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414   -0.7762    0.8779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854   -0.3681    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407   -1.8608    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3207   -0.0883   -1.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9815    0.3406    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3477    1.6052    1.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346    2.0423    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    1.2466   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5595    2.0652   -1.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871    1.0144    0.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5064   -0.9119    2.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -0.1072    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -1.8148    1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7812   -0.6386   -1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0916   -2.1229   -0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -1.7397   -1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6739   -0.1952   -2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158   -2.0882    0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276   -2.2659    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -2.4169   -0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3250   -0.5397   -1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034    0.9624   -1.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8937   -0.6655   -2.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8824   -0.3304    2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0829    0.4980    1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294    2.2256    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805    2.9960    1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9239    3.0847   -0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3580    1.7015   -1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997    2.2517   -1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  6  2  1  0
 15  2  1  0
 13  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  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       2.080   1.694   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.312   1.078   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.312  -0.462   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.538   2.618   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.692   1.078   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.846   1.694   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.004  -2.156   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.926  -1.078   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.464  -2.618   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.312   0.924   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.924   0.461   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.924  -1.232   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.384  -1.694   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.692  -0.462   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.692  -0.001   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    5                                                            
CONECT    5    1    4    6   14                                             
CONECT    6    5   11                                                       
CONECT    7    8                                                            
CONECT    8    3    7    9   14                                             
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11    6   10   12   15                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    5    8   13   15                                             
CONECT   15   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0037776
HETATM    1  C1  UNL     1       2.981  -0.790   1.471  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.944  -0.351   0.507  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.020  -1.045  -0.837  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.600  -0.787  -1.361  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.035  -0.130  -0.194  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.641  -0.776   0.878  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.485  -0.368   0.006  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.641  -1.861   0.257  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.321  -0.088  -1.226  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.981   0.341   1.211  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.348   1.605   1.552  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.235   2.042   1.008  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.453   1.247  -0.011  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.559   2.065  -1.267  1.00  0.00           C  
HETATM   15  O2  UNL     1       1.787   1.014   0.410  1.00  0.00           O  
HETATM   16  H1  UNL     1       2.506  -0.912   2.476  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.827  -0.107   1.473  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.342  -1.815   1.194  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.781  -0.639  -1.500  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.092  -2.123  -0.653  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.093  -1.740  -1.624  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.674  -0.195  -2.270  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.516  -2.088   0.883  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.728  -2.266   0.782  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.657  -2.417  -0.723  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.325  -0.540  -1.026  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.403   0.962  -1.480  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.894  -0.665  -2.072  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.882  -0.330   2.108  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.083   0.498   1.075  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.829   2.226   2.305  1.00  0.00           H  
HETATM   32  H17 UNL     1       0.180   2.996   1.312  1.00  0.00           H  
HETATM   33  H18 UNL     1       0.924   3.085  -0.940  1.00  0.00           H  
HETATM   34  H19 UNL     1       1.358   1.701  -1.958  1.00  0.00           H  
HETATM   35  H20 UNL     1      -0.400   2.252  -1.766  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    6   15
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6    7   13
CONECT    7    8    9   10
CONECT    8   23   24   25
CONECT    9   26   27   28
CONECT   10   11   29   30
CONECT   11   12   12   31
CONECT   12   13   32
CONECT   13   14   15
CONECT   14   33   34   35
END

HMDB0037776
     RDKit          3D
5,9:6,9-Diepoxy-3-megastigmene
 35 37  0  0  0  0  0  0  0  0999 V2000
    2.9805   -0.7905    1.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440   -0.3515    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0204   -1.0448   -0.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996   -0.7867   -1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351   -0.1303   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414   -0.7762    0.8779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854   -0.3681    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407   -1.8608    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3207   -0.0883   -1.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9815    0.3406    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3477    1.6052    1.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346    2.0423    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    1.2466   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5595    2.0652   -1.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871    1.0144    0.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5064   -0.9119    2.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -0.1072    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -1.8148    1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7812   -0.6386   -1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0916   -2.1229   -0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -1.7397   -1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6739   -0.1952   -2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158   -2.0882    0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276   -2.2659    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -2.4169   -0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3250   -0.5397   -1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034    0.9624   -1.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8937   -0.6655   -2.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8824   -0.3304    2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0829    0.4980    1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294    2.2256    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805    2.9960    1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9239    3.0847   -0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3580    1.7015   -1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997    2.2517   -1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  6  2  1  0
 15  2  1  0
 13  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2,6,8-Tetramethyl-7,11-dioxatricyclo[6.2.1.01,6]undec-4-ene	HMDB

Chemical Formula

C₁₃H₂₀O₂

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

IUPAC Name

2,2,6,8-tetramethyl-7,11-dioxatricyclo[6.2.1.0¹,⁶]undec-4-ene

Traditional Name

2,2,6,8-tetramethyl-7,11-dioxatricyclo[6.2.1.0¹,⁶]undec-4-ene

CAS Registry Number

Not Available

SMILES

CC12CCC3(O1)C(C)(O2)C=CCC3(C)C

InChI Identifier

InChI=1S/C13H20O2/c1-10(2)6-5-7-11(3)13(10)9-8-12(4,14-11)15-13/h5,7H,6,8-9H2,1-4H3

InChI Key

QXHORPLJTIHQGR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Oxane
Tetrahydrofuran
Meta-dioxolane
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037776)
Cell membrane (HMDB: HMDB0037776)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037776)

Source

Exogenous

Exogenous (HMDB: HMDB0037776)

Food

Food (HMDB: HMDB0037776)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0037776)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Emulsifier (HMDB: HMDB0037776)

Biological role

Nutrient (HMDB: HMDB0037776)

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
Water Solubility	0.044 g/L	ALOGPS
logP	3.29	ALOGPS
logP	2.81	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	59.94 m³·mol⁻¹	ChemAxon
Polarizability	23.69 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	148.836	31661259
DarkChem	[M-H]-	144.814	31661259
DeepCCS	[M-2H]-	185.718	30932474
DeepCCS	[M+Na]+	160.867	30932474
AllCCS	[M+H]+	145.6	32859911
AllCCS	[M+H-H2O]+	141.5	32859911
AllCCS	[M+NH4]+	149.4	32859911
AllCCS	[M+Na]+	150.5	32859911
AllCCS	[M-H]-	155.3	32859911
AllCCS	[M+Na-2H]-	155.6	32859911
AllCCS	[M+HCOO]-	156.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	5.31 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5135 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.4 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2352.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	410.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	224.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	804.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	681.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	72.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1272.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	329.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1352.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	570.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	296.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	509.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	531.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,9:6,9-Diepoxy-3-megastigmene	CC12CCC3(O1)C(C)(O2)C=CCC3(C)C	1648.3	Standard polar	33892256
5,9:6,9-Diepoxy-3-megastigmene	CC12CCC3(O1)C(C)(O2)C=CCC3(C)C	1318.8	Standard non polar	33892256
5,9:6,9-Diepoxy-3-megastigmene	CC12CCC3(O1)C(C)(O2)C=CCC3(C)C	1328.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7900000000-069396d45e3b6a79f3fc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 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 - 5,9:6,9-Diepoxy-3-megastigmene 10V, Positive-QTOF	splash10-0a4i-0090000000-4eb8ff4e89af04ef391b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 20V, Positive-QTOF	splash10-0a4i-9370000000-51e39f808704eed721fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 40V, Positive-QTOF	splash10-0aou-9100000000-6eaa43d87f99b1cbbf8e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 10V, Negative-QTOF	splash10-0a4i-0090000000-913dedc56c9efc8c09b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 20V, Negative-QTOF	splash10-0a4i-0390000000-09a5c5562cb95e2c3376	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 40V, Negative-QTOF	splash10-004l-2900000000-239ded508c2665de6ff0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 10V, Negative-QTOF	splash10-0a4i-0090000000-43a9bdbf7663e467c30d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 20V, Negative-QTOF	splash10-0a4i-0090000000-43a9bdbf7663e467c30d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 40V, Negative-QTOF	splash10-0a4i-0290000000-24af5dcd0be210980e3e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 10V, Positive-QTOF	splash10-0a4i-0090000000-6638fe304d1153357042	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 20V, Positive-QTOF	splash10-0a4i-0490000000-bc26c8a44dd80ba2d79c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-3-megastigmene 40V, Positive-QTOF	splash10-0a4i-9680000000-48e8eead4c0453a4a331	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB016918

KNApSAcK ID

Not Available

Chemspider ID

35014468

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73817712

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 5,9:6,9-Diepoxy-3-megastigmene (HMDB0037776)

MOL for HMDB0037776 (5,9:6,9-Diepoxy-3-megastigmene)

3D MOL for HMDB0037776 (5,9:6,9-Diepoxy-3-megastigmene)

3D SDF for HMDB0037776 (5,9:6,9-Diepoxy-3-megastigmene)

3D-SDF for HMDB0037776 (5,9:6,9-Diepoxy-3-megastigmene)

PDB for HMDB0037776 (5,9:6,9-Diepoxy-3-megastigmene)

3D PDB for HMDB0037776 (5,9:6,9-Diepoxy-3-megastigmene)

SMILES for HMDB0037776 (5,9:6,9-Diepoxy-3-megastigmene)

INCHI for HMDB0037776 (5,9:6,9-Diepoxy-3-megastigmene)

Structure for HMDB0037776 (5,9:6,9-Diepoxy-3-megastigmene)

3D Structure for HMDB0037776 (5,9:6,9-Diepoxy-3-megastigmene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra