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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:51:01 UTC

Update Date

2023-02-21 17:26:38 UTC

HMDB ID

HMDB0038529

Secondary Accession Numbers

HMDB38529

Metabolite Identification

Common Name

5,9:6,9-Diepoxy-4-megastigmene

Description

5,9:6,9-Diepoxy-4-megastigmene 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. 5,9:6,9-Diepoxy-4-megastigmene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,9:6,9-diepoxy-4-megastigmene has been detected, but not quantified in, alcoholic beverages. This could make 5,9:6,9-diepoxy-4-megastigmene a potential biomarker for the consumption of these foods.

Structure

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

HMDB0038529
     RDKit          3D
5,9:6,9-Diepoxy-4-megastigmene
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.3025    0.7818    1.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271    0.3411    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413   -1.1672    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5492   -1.4170    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070   -0.0367    0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292    0.8545    0.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0541    0.1564   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9638   -0.3263   -2.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -1.0315   -1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -0.6314   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3664    0.2042    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078    1.6621    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    0.0053    2.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2227    0.8622   -1.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3724    0.6918   -1.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -0.0146    1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0248    1.6811    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835    0.9780    0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572   -1.6200   -0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576   -1.5760    1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2535   -1.7429    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -2.1199   -0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9348   -0.1877   -3.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9978   -0.8345   -2.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9846   -2.1418   -1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773   -0.0917   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5701   -1.5335    0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549    1.8307   -0.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633    2.3310    0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279    1.8550    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9170    0.8008    2.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164   -1.0059    2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3385   -0.0465    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3873    0.5438   -2.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9629    1.9455   -1.9551 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  7 14  1  0
 14 15  1  0
  6  2  1  0
 15  2  1  0
 11  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
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
M  END


  Mrv0541 02241214482D          

 15 17  0  0  0  0            999 V2000
   -2.0030   -0.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0030    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818    1.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    1.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010    1.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824   -1.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818   -0.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8811   -1.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0798    0.3202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407   -0.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -0.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010   -0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1215    0.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030    0.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  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>
HMDB0038529

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3(O1)C(CO2)=CCCC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O2/c1-11(2)6-4-5-10-9-14-12(3)7-8-13(10,11)15-12/h5H,4,6-9H2,1-3H3

> <INCHI_KEY>
AKKNWGRLXKHQDH-UHFFFAOYSA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.70072792226603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2,9-trimethyl-8,12-dioxatricyclo[7.2.1.0¹,⁶]dodec-5-ene

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
2.569776631999999

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0856394940000405

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
59.9983

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,9-trimethyl-8,12-dioxatricyclo[7.2.1.0¹,⁶]dodec-5-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038529
     RDKit          3D
5,9:6,9-Diepoxy-4-megastigmene
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.3025    0.7818    1.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271    0.3411    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413   -1.1672    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5492   -1.4170    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070   -0.0367    0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292    0.8545    0.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0541    0.1564   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9638   -0.3263   -2.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -1.0315   -1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -0.6314   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3664    0.2042    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078    1.6621    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    0.0053    2.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2227    0.8622   -1.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3724    0.6918   -1.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -0.0146    1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0248    1.6811    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835    0.9780    0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572   -1.6200   -0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576   -1.5760    1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2535   -1.7429    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -2.1199   -0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9348   -0.1877   -3.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9978   -0.8345   -2.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9846   -2.1418   -1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773   -0.0917   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5701   -1.5335    0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549    1.8307   -0.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633    2.3310    0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279    1.8550    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9170    0.8008    2.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164   -1.0059    2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3385   -0.0465    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3873    0.5438   -2.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9629    1.9455   -1.9551 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  7 14  1  0
 14 15  1  0
  6  2  1  0
 15  2  1  0
 11  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
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 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      -3.739  -0.149   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.739   1.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.393   2.093   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.196   1.345   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.001   2.243   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.495   1.944   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.140  -2.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.393  -0.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.645  -2.243   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.149   0.598   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.196  -0.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.001  -1.196   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.495  -0.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.093   0.598   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.739   0.598   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5   14                                                       
CONECT    7    8                                                            
CONECT    8    1    7    9   11                                             
CONECT    9    8                                                            
CONECT   10   11   14                                                       
CONECT   11    4    8   10   12                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    6   10   13   15                                             
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0038529
HETATM    1  C1  UNL     1       3.302   0.782   1.018  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.127   0.341   0.153  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.041  -1.167   0.262  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.549  -1.417   0.393  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.007  -0.037   0.114  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.929   0.855   0.652  1.00  0.00           O  
HETATM    7  C6  UNL     1       0.054   0.156  -1.360  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.964  -0.326  -2.057  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.120  -1.031  -1.464  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.405  -0.631  -0.046  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.366   0.204   0.593  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.708   1.662   0.366  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.375   0.005   2.115  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.223   0.862  -1.916  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.372   0.692  -1.157  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.616  -0.015   1.718  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.025   1.681   1.610  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.183   0.978   0.354  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.457  -1.620  -0.667  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.558  -1.576   1.131  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.254  -1.743   1.388  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.272  -2.120  -0.422  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.935  -0.188  -3.143  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.998  -0.835  -2.116  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.985  -2.142  -1.475  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.377  -0.092  -0.024  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.570  -1.533   0.615  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.755   1.831  -0.737  1.00  0.00           H  
HETATM   29  H14 UNL     1      -0.963   2.331   0.843  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.728   1.855   0.758  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.917   0.801   2.625  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.816  -1.006   2.273  1.00  0.00           H  
HETATM   33  H18 UNL     1      -0.338  -0.046   2.514  1.00  0.00           H  
HETATM   34  H19 UNL     1       1.387   0.544  -2.956  1.00  0.00           H  
HETATM   35  H20 UNL     1       0.963   1.946  -1.955  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   11
CONECT    7    8    8   14
CONECT    8    9   23
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12   13
CONECT   12   28   29   30
CONECT   13   31   32   33
CONECT   14   15   34   35
END

HMDB0038529
     RDKit          3D
5,9:6,9-Diepoxy-4-megastigmene
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.3025    0.7818    1.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271    0.3411    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413   -1.1672    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5492   -1.4170    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070   -0.0367    0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292    0.8545    0.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0541    0.1564   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9638   -0.3263   -2.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -1.0315   -1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -0.6314   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3664    0.2042    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078    1.6621    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    0.0053    2.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2227    0.8622   -1.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3724    0.6918   -1.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -0.0146    1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0248    1.6811    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835    0.9780    0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572   -1.6200   -0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576   -1.5760    1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2535   -1.7429    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -2.1199   -0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9348   -0.1877   -3.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9978   -0.8345   -2.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9846   -2.1418   -1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773   -0.0917   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5701   -1.5335    0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549    1.8307   -0.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633    2.3310    0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279    1.8550    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9170    0.8008    2.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164   -1.0059    2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3385   -0.0465    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3873    0.5438   -2.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9629    1.9455   -1.9551 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  7 14  1  0
 14 15  1  0
  6  2  1  0
 15  2  1  0
 11  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
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2,9-Trimethyl-8,12-dioxatricyclo[7.2.1.01,6]dodec-5-ene	HMDB

Chemical Formula

C₁₃H₂₀O₂

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

IUPAC Name

2,2,9-trimethyl-8,12-dioxatricyclo[7.2.1.0¹,⁶]dodec-5-ene

Traditional Name

2,2,9-trimethyl-8,12-dioxatricyclo[7.2.1.0¹,⁶]dodec-5-ene

CAS Registry Number

133661-30-0

SMILES

CC12CCC3(O1)C(CO2)=CCCC3(C)C

InChI Identifier

InChI=1S/C13H20O2/c1-11(2)6-4-5-10-9-14-12(3)7-8-13(10,11)15-12/h5H,4,6-9H2,1-3H3

InChI Key

AKKNWGRLXKHQDH-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

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038529)
Cell membrane (HMDB: HMDB0038529)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038529)

Source

Exogenous

Food

Food (HMDB: HMDB0038529)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038529)

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	0.42 g/L	ALOGPS
logP	3.36	ALOGPS
logP	2.57	ChemAxon
logS	-2.7	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	60 m³·mol⁻¹	ChemAxon
Polarizability	23.7 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]+	148.843	31661259
DarkChem	[M-H]-	143.35	31661259
DeepCCS	[M-2H]-	185.486	30932474
DeepCCS	[M+Na]+	160.487	30932474
AllCCS	[M+H]+	147.1	32859911
AllCCS	[M+H-H2O]+	143.0	32859911
AllCCS	[M+NH4]+	150.9	32859911
AllCCS	[M+Na]+	152.0	32859911
AllCCS	[M-H]-	155.7	32859911
AllCCS	[M+Na-2H]-	155.9	32859911
AllCCS	[M+HCOO]-	156.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,9:6,9-Diepoxy-4-megastigmene	CC12CCC3(O1)C(CO2)=CCCC3(C)C	1859.4	Standard polar	33892256
5,9:6,9-Diepoxy-4-megastigmene	CC12CCC3(O1)C(CO2)=CCCC3(C)C	1404.5	Standard non polar	33892256
5,9:6,9-Diepoxy-4-megastigmene	CC12CCC3(O1)C(CO2)=CCCC3(C)C	1446.3	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-4-megastigmene GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-4900000000-c020ea74bbdad36ea1ae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,9:6,9-Diepoxy-4-megastigmene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,9:6,9-Diepoxy-4-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-4-megastigmene 10V, Positive-QTOF	splash10-0a4i-0190000000-1fce9484c17d26ec5abb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-4-megastigmene 20V, Positive-QTOF	splash10-0a4i-7490000000-c9dcbda04d77e56d9d3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-4-megastigmene 40V, Positive-QTOF	splash10-066u-9100000000-78067b13adbfe3cf73cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-4-megastigmene 10V, Negative-QTOF	splash10-0a4i-0090000000-c3f19a789e66c47793c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-4-megastigmene 20V, Negative-QTOF	splash10-0a4i-0390000000-9b48e9ba54e35d1f7dfd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-4-megastigmene 40V, Negative-QTOF	splash10-03g1-2900000000-a6b4f826e06d77e63f51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-4-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-4-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-4-megastigmene 40V, Negative-QTOF	splash10-0a6r-0970000000-5f400a5c7a78b094f6fc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-4-megastigmene 10V, Positive-QTOF	splash10-0a4i-0090000000-6638fe304d1153357042	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-4-megastigmene 20V, Positive-QTOF	splash10-0aor-8290000000-fae4b607f59976ddc26e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,9:6,9-Diepoxy-4-megastigmene 40V, Positive-QTOF	splash10-003f-8920000000-b05a4714f5bbd8a6db9e	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB017914

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73817713

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-4-megastigmene (HMDB0038529)

MOL for HMDB0038529 (5,9:6,9-Diepoxy-4-megastigmene)

3D MOL for HMDB0038529 (5,9:6,9-Diepoxy-4-megastigmene)

3D SDF for HMDB0038529 (5,9:6,9-Diepoxy-4-megastigmene)

3D-SDF for HMDB0038529 (5,9:6,9-Diepoxy-4-megastigmene)

PDB for HMDB0038529 (5,9:6,9-Diepoxy-4-megastigmene)

3D PDB for HMDB0038529 (5,9:6,9-Diepoxy-4-megastigmene)

SMILES for HMDB0038529 (5,9:6,9-Diepoxy-4-megastigmene)

INCHI for HMDB0038529 (5,9:6,9-Diepoxy-4-megastigmene)

Structure for HMDB0038529 (5,9:6,9-Diepoxy-4-megastigmene)

3D Structure for HMDB0038529 (5,9:6,9-Diepoxy-4-megastigmene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra