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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:55:12 UTC

Update Date

2022-03-07 02:54:18 UTC

HMDB ID

HMDB0034984

Secondary Accession Numbers

HMDB34984

Metabolite Identification

Common Name

(5R,6S)-5,6-Epoxy-7-megastigmen-9-one

Description

(5R,6S)-5,6-Epoxy-7-megastigmen-9-one 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 (5R,6S)-5,6-Epoxy-7-megastigmen-9-one is a sweet, berry, and fruity tasting compound (5R,6S)-5,6-Epoxy-7-megastigmen-9-one has been detected, but not quantified in, watermelons (Citrullus lanatus). This could make (5R,6S)-5,6-epoxy-7-megastigmen-9-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (5R,6S)-5,6-Epoxy-7-megastigmen-9-one.

Structure

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

HMDB0034984
     RDKit          3D
(5R,6S)-5,6-Epoxy-7-megastigmen-9-one
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.2263   -0.0905   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840   -0.8414    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9741   -1.4957    1.6645 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148   -0.8279    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2599   -0.1623   -0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2259   -0.1417   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -0.4644   -1.7377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9912   -1.2421   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -2.6374   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4618   -1.1431   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187   -0.0644    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084    1.2285    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8177    1.1681    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503    1.5424    1.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3280    2.2380   -0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2120   -0.5621   -0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921    0.9857    0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7718   -0.0780   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3519   -1.3854    1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145    0.4070   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4526   -2.7128   -1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238   -3.2857   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -3.1033    0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0113   -0.8414   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374   -2.0877   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150   -0.2886    1.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8960   -0.0483    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051    2.1126    0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6538    1.3314   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1955    2.5225    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3133    0.7909    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967    1.6936    2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7393    2.4630   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    3.1469   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5783    1.8737   -1.9443 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
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  8  6  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
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
M  END


  Mrv0541 02241208502D          

 15 16  0  0  0  0            999 V2000
   -0.4121   -1.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4951   -0.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799    0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371    0.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773    0.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4951    0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2470    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424    0.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674    0.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799    1.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3299   -0.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6504    1.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8977    0.1237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034984

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)\C=C\C12OC1(C)CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O2/c1-10(14)6-9-13-11(2,3)7-5-8-12(13,4)15-13/h6,9H,5,7-8H2,1-4H3/b9-6+

> <INCHI_KEY>
ZTJZJYUGOJYHCU-RMKNXTFCSA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.947806853468908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}but-3-en-2-one

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
2.801826208666667

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.834268000666622

> <JCHEM_PKA_STRONGEST_BASIC>
-4.273887743309496

> <JCHEM_POLAR_SURFACE_AREA>
29.6

> <JCHEM_REFRACTIVITY>
60.553799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-4-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}but-3-en-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034984
     RDKit          3D
(5R,6S)-5,6-Epoxy-7-megastigmen-9-one
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.2263   -0.0905   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840   -0.8414    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9741   -1.4957    1.6645 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148   -0.8279    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2599   -0.1623   -0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2259   -0.1417   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -0.4644   -1.7377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9912   -1.2421   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -2.6374   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4618   -1.1431   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187   -0.0644    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084    1.2285    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8177    1.1681    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503    1.5424    1.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3280    2.2380   -0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2120   -0.5621   -0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921    0.9857    0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7718   -0.0780   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3519   -1.3854    1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145    0.4070   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4526   -2.7128   -1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238   -3.2857   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -3.1033    0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0113   -0.8414   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374   -2.0877   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150   -0.2886    1.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8960   -0.0483    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051    2.1126    0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6538    1.3314   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1955    2.5225    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3133    0.7909    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967    1.6936    2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7393    2.4630   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    3.1469   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5783    1.8737   -1.9443 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
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  8  6  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
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 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      -0.769  -2.849   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.924  -1.308   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.309  -1.924   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.696  -1.308   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.696   0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.309   1.001   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.078   1.771   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.924   0.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.461   0.384   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.386   1.617   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.926   1.617   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.696   2.849   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.616  -1.616   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.081   2.387   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.542   0.231   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   13                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   14                                             
CONECT    7    6    8                                                       
CONECT    8    2    6    7    9                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11                                                            
CONECT   13    2                                                            
CONECT   14    6                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0034984
HETATM    1  C1  UNL     1       4.226  -0.090  -0.198  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.384  -0.841   0.766  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.974  -1.496   1.664  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.915  -0.828   0.682  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.260  -0.162  -0.233  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.226  -0.142  -0.327  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.574  -0.464  -1.738  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.991  -1.242  -0.551  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.457  -2.637  -0.642  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.462  -1.143  -0.361  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.819  -0.064   0.661  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.308   1.229   0.033  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.818   1.168   0.044  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.350   1.542   1.432  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.328   2.238  -0.943  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.212  -0.562  -0.248  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.292   0.986   0.095  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.772  -0.078  -1.231  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.352  -1.385   1.400  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.815   0.407  -0.966  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.453  -2.713  -1.267  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.224  -3.286  -1.153  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.329  -3.103   0.366  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.011  -0.841  -1.298  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.937  -2.088  -0.037  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.215  -0.289   1.563  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.896  -0.048   0.836  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.605   2.113   0.668  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.654   1.331  -1.002  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.196   2.522   1.414  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.313   0.791   1.877  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.197   1.694   2.135  1.00  0.00           H  
HETATM   33  H18 UNL     1       0.739   2.463  -0.789  1.00  0.00           H  
HETATM   34  H19 UNL     1      -0.923   3.147  -0.707  1.00  0.00           H  
HETATM   35  H20 UNL     1      -0.578   1.874  -1.944  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    8   13
CONECT    7    8
CONECT    8    9   10
CONECT    9   21   22   23
CONECT   10   11   24   25
CONECT   11   12   26   27
CONECT   12   13   28   29
CONECT   13   14   15
CONECT   14   30   31   32
CONECT   15   33   34   35
END

HMDB0034984
     RDKit          3D
(5R,6S)-5,6-Epoxy-7-megastigmen-9-one
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.2263   -0.0905   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840   -0.8414    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9741   -1.4957    1.6645 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148   -0.8279    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2599   -0.1623   -0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2259   -0.1417   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -0.4644   -1.7377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9912   -1.2421   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -2.6374   -0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4618   -1.1431   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187   -0.0644    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084    1.2285    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8177    1.1681    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503    1.5424    1.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3280    2.2380   -0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2120   -0.5621   -0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921    0.9857    0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7718   -0.0780   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3519   -1.3854    1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145    0.4070   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4526   -2.7128   -1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238   -3.2857   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -3.1033    0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0113   -0.8414   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374   -2.0877   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150   -0.2886    1.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8960   -0.0483    0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051    2.1126    0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6538    1.3314   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1955    2.5225    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3133    0.7909    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967    1.6936    2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7393    2.4630   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    3.1469   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5783    1.8737   -1.9443 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
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  8  6  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
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6-Epoxy-beta-ionone	MeSH

Chemical Formula

C₁₃H₂₀O₂

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

IUPAC Name

(3E)-4-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}but-3-en-2-one

Traditional Name

(3E)-4-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}but-3-en-2-one

CAS Registry Number

Not Available

SMILES

CC(=O)\C=C\C12OC1(C)CCCC2(C)C

InChI Identifier

InChI=1S/C13H20O2/c1-10(14)6-9-13-11(2,3)7-5-8-12(13,4)15-13/h6,9H,5,7-8H2,1-4H3/b9-6+

InChI Key

ZTJZJYUGOJYHCU-RMKNXTFCSA-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
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Oxacycle
Ether
Oxirane
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

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	48.5 - 49.5 °C	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	0.048 g/L	ALOGPS
logP	3.2	ALOGPS
logP	2.8	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	19.83	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.55 m³·mol⁻¹	ChemAxon
Polarizability	23.95 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M-2H]-	181.69	30932474
DeepCCS	[M+Na]+	156.758	30932474
AllCCS	[M+H]+	147.2	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	150.9	32859911
AllCCS	[M+Na]+	151.9	32859911
AllCCS	[M-H]-	155.0	32859911
AllCCS	[M+Na-2H]-	155.6	32859911
AllCCS	[M+HCOO]-	156.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(5R,6S)-5,6-Epoxy-7-megastigmen-9-one	CC(=O)\C=C\C12OC1(C)CCCC2(C)C	2045.7	Standard polar	33892256
(5R,6S)-5,6-Epoxy-7-megastigmen-9-one	CC(=O)\C=C\C12OC1(C)CCCC2(C)C	1462.7	Standard non polar	33892256
(5R,6S)-5,6-Epoxy-7-megastigmen-9-one	CC(=O)\C=C\C12OC1(C)CCCC2(C)C	1466.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(5R,6S)-5,6-Epoxy-7-megastigmen-9-one,1TMS,isomer #1	C=C(/C=C/C12OC1(C)CCCC2(C)C)O[Si](C)(C)C	1640.1	Semi standard non polar	33892256
(5R,6S)-5,6-Epoxy-7-megastigmen-9-one,1TMS,isomer #1	C=C(/C=C/C12OC1(C)CCCC2(C)C)O[Si](C)(C)C	1611.0	Standard non polar	33892256
(5R,6S)-5,6-Epoxy-7-megastigmen-9-one,1TBDMS,isomer #1	C=C(/C=C/C12OC1(C)CCCC2(C)C)O[Si](C)(C)C(C)(C)C	1880.1	Semi standard non polar	33892256
(5R,6S)-5,6-Epoxy-7-megastigmen-9-one,1TBDMS,isomer #1	C=C(/C=C/C12OC1(C)CCCC2(C)C)O[Si](C)(C)C(C)(C)C	1862.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one EI-B (Non-derivatized)	splash10-00di-3900000000-642601a39cf4828a95cc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one EI-B (Non-derivatized)	splash10-00di-3900000000-642601a39cf4828a95cc	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-9800000000-13d41ca061e64c920db9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 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 - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 10V, Positive-QTOF	splash10-0a4l-1980000000-ab9ee34d0704e1203f75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 20V, Positive-QTOF	splash10-052f-6930000000-677e48043052ae8aa6eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 40V, Positive-QTOF	splash10-05nf-9100000000-c9569a9bf6b01df749fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 10V, Negative-QTOF	splash10-0a4i-0390000000-25629cabf4557eb256b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 20V, Negative-QTOF	splash10-0a4i-1980000000-3ff703712ae234f70567	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 40V, Negative-QTOF	splash10-0080-3900000000-d31c654648f4308ec251	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 10V, Negative-QTOF	splash10-066r-0980000000-30ceab1651a7cfac80dc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 20V, Negative-QTOF	splash10-000i-0920000000-c6d7089ea87e89a6ca35	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 40V, Negative-QTOF	splash10-05g0-0910000000-a61bfd0db05ab7db837b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 10V, Positive-QTOF	splash10-052f-0940000000-3fbf6630fa03ee051c9a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 20V, Positive-QTOF	splash10-0a4l-1970000000-c4f484b79f9008b6e759	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5R,6S)-5,6-Epoxy-7-megastigmen-9-one 40V, Positive-QTOF	splash10-009f-9300000000-a4b084ffa5ef5aab4e26	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB013585

KNApSAcK ID

Not Available

Chemspider ID

4509354

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352481

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 (5R,6S)-5,6-Epoxy-7-megastigmen-9-one (HMDB0034984)

MOL for HMDB0034984 ((5R,6S)-5,6-Epoxy-7-megastigmen-9-one)

3D MOL for HMDB0034984 ((5R,6S)-5,6-Epoxy-7-megastigmen-9-one)

3D SDF for HMDB0034984 ((5R,6S)-5,6-Epoxy-7-megastigmen-9-one)

3D-SDF for HMDB0034984 ((5R,6S)-5,6-Epoxy-7-megastigmen-9-one)

PDB for HMDB0034984 ((5R,6S)-5,6-Epoxy-7-megastigmen-9-one)

3D PDB for HMDB0034984 ((5R,6S)-5,6-Epoxy-7-megastigmen-9-one)

SMILES for HMDB0034984 ((5R,6S)-5,6-Epoxy-7-megastigmen-9-one)

INCHI for HMDB0034984 ((5R,6S)-5,6-Epoxy-7-megastigmen-9-one)

Structure for HMDB0034984 ((5R,6S)-5,6-Epoxy-7-megastigmen-9-one)

3D Structure for HMDB0034984 ((5R,6S)-5,6-Epoxy-7-megastigmen-9-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra