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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:34:14 UTC

Update Date

2022-03-07 02:54:12 UTC

HMDB ID

HMDB0034672

Secondary Accession Numbers

HMDB34672

Metabolite Identification

Common Name

(5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol

Description

(5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol has been detected, but not quantified in, fruits. This could make (5alpha,8beta,9beta)-5,9-epoxy-3,6-megastigmadien-8-ol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol.

Structure

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

HMDB0034672
     RDKit          3D
(5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol
 35 36  0  0  0  0  0  0  0  0999 V2000
    3.8236    0.3906   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3127    0.4964   -0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022   -0.5280   -0.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4467   -0.6332   -0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793   -2.1048   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0197   -0.0585   -2.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937    0.2446   -2.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    0.0127   -1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7422    0.2656    0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -0.6476    1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380    1.7102    0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2716    0.1062    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3166    0.6368    1.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7855    0.4715    1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0106   -0.8282    1.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740   -0.7074    0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.9897    0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1479    0.7178   -1.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0341    1.5143   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216   -2.3175   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9634   -2.7321   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665   -2.4515   -1.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824    0.1207   -2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6150    0.6534   -3.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630    0.6887   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942   -1.0566   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -0.9829    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8818   -1.5508    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3765   -0.0871    1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321    2.0381   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350    1.7311    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2009    2.3702    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165    1.1713    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2695    1.2329    2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0126   -0.8766    2.8959 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14  2  1  0
 12  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  5 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
M  END


  Mrv0541 05061308002D          

 15 16  0  0  0  0            999 V2000
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
  9  1  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  4  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034672

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC2(C)C=CCC(C)(C)C2=CC1O

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

> <INCHI_KEY>
ULAJGYNCWKGREU-UHFFFAOYSA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.796649213598318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,5,8a-tetramethyl-3,5,6,8a-tetrahydro-2H-1-benzopyran-3-ol

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.0914103893333333

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.807491008787064

> <JCHEM_PKA_STRONGEST_BASIC>
-3.320403432756537

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
62.3915

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5,5,8a-tetramethyl-3,6-dihydro-2H-1-benzopyran-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034672
     RDKit          3D
(5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol
 35 36  0  0  0  0  0  0  0  0999 V2000
    3.8236    0.3906   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3127    0.4964   -0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022   -0.5280   -0.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4467   -0.6332   -0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793   -2.1048   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0197   -0.0585   -2.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937    0.2446   -2.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    0.0127   -1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7422    0.2656    0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -0.6476    1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380    1.7102    0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2716    0.1062    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3166    0.6368    1.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7855    0.4715    1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0106   -0.8282    1.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740   -0.7074    0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.9897    0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1479    0.7178   -1.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0341    1.5143   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216   -2.3175   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9634   -2.7321   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665   -2.4515   -1.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824    0.1207   -2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6150    0.6534   -3.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630    0.6887   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942   -1.0566   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -0.9829    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8818   -1.5508    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3765   -0.0871    1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321    2.0381   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350    1.7311    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2009    2.3702    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165    1.1713    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2695    1.2329    2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0126   -0.8766    2.8959 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14  2  1  0
 12  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  5 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.990   0.360   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.990   0.360   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5    6    7                                                       
CONECT    6    5   12                                                       
CONECT    7    5   13                                                       
CONECT    8   10   11                                                       
CONECT    9    1   10   15                                                  
CONECT   10    8    9   14                                                  
CONECT   11    8   12   13                                                  
CONECT   12    2    3    6   11                                             
CONECT   13    4    7   11   15                                             
CONECT   14   10                                                            
CONECT   15    9   13                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0034672
HETATM    1  C1  UNL     1       3.824   0.391  -0.015  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.313   0.496  -0.002  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.802  -0.528  -0.743  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.447  -0.633  -0.789  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.079  -2.105  -0.819  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.020  -0.059  -2.101  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.294   0.245  -2.303  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.270   0.013  -1.219  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.742   0.266   0.151  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.483  -0.648   1.124  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.038   1.710   0.577  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.272   0.106   0.273  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.317   0.637   1.328  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.786   0.471   1.439  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.011  -0.828   1.913  1.00  0.00           O  
HETATM   16  H1  UNL     1       4.074  -0.707   0.051  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.312   0.990   0.752  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.148   0.718  -1.030  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.034   1.514  -0.398  1.00  0.00           H  
HETATM   20  H5  UNL     1      -0.722  -2.318  -0.101  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.963  -2.732  -0.508  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.166  -2.451  -1.854  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.682   0.121  -2.914  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.615   0.653  -3.241  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.163   0.689  -1.363  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.594  -1.057  -1.276  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.852  -0.983   1.946  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.882  -1.551   0.613  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.376  -0.087   1.491  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.932   2.038  -0.010  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.235   1.731   1.665  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.201   2.370   0.330  1.00  0.00           H  
HETATM   33  H18 UNL     1      -0.217   1.171   2.093  1.00  0.00           H  
HETATM   34  H19 UNL     1       2.269   1.233   2.046  1.00  0.00           H  
HETATM   35  H20 UNL     1       2.013  -0.877   2.896  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   14   19
CONECT    3    4
CONECT    4    5    6   12
CONECT    5   20   21   22
CONECT    6    7    7   23
CONECT    7    8   24
CONECT    8    9   25   26
CONECT    9   10   11   12
CONECT   10   27   28   29
CONECT   11   30   31   32
CONECT   12   13   13
CONECT   13   14   33
CONECT   14   15   34
CONECT   15   35
END

HMDB0034672
     RDKit          3D
(5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol
 35 36  0  0  0  0  0  0  0  0999 V2000
    3.8236    0.3906   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3127    0.4964   -0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022   -0.5280   -0.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4467   -0.6332   -0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793   -2.1048   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0197   -0.0585   -2.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937    0.2446   -2.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    0.0127   -1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7422    0.2656    0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -0.6476    1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380    1.7102    0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2716    0.1062    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3166    0.6368    1.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7855    0.4715    1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0106   -0.8282    1.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740   -0.7074    0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.9897    0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1479    0.7178   -1.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0341    1.5143   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216   -2.3175   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9634   -2.7321   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665   -2.4515   -1.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824    0.1207   -2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6150    0.6534   -3.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630    0.6887   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942   -1.0566   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -0.9829    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8818   -1.5508    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3765   -0.0871    1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321    2.0381   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350    1.7311    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2009    2.3702    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165    1.1713    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2695    1.2329    2.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0126   -0.8766    2.8959 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14  2  1  0
 12  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  5 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5a,8b,9b)-5,9-Epoxy-3,6-megastigmadien-8-ol	Generator
(5Α,8β,9β)-5,9-epoxy-3,6-megastigmadien-8-ol	Generator

Chemical Formula

C₁₃H₂₀O₂

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

IUPAC Name

2,5,5,8a-tetramethyl-3,5,6,8a-tetrahydro-2H-1-benzopyran-3-ol

Traditional Name

2,5,5,8a-tetramethyl-3,6-dihydro-2H-1-benzopyran-3-ol

CAS Registry Number

69927-26-0

SMILES

CC1OC2(C)C=CCC(C)(C)C2=CC1O

InChI Identifier

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

InChI Key

ULAJGYNCWKGREU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Pyran
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034672)
Cell membrane (HMDB: HMDB0034672)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034672)

Source

Exogenous

Exogenous (HMDB: HMDB0034672)

Food

Food (HMDB: HMDB0034672)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034672)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034672)

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	0.84 g/L	ALOGPS
logP	2.65	ALOGPS
logP	2.09	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.81	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	62.39 m³·mol⁻¹	ChemAxon
Polarizability	23.8 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
DarkChem	[M+H]+	149.951	31661259
DarkChem	[M-H]-	149.058	31661259
DeepCCS	[M+H]+	151.703	30932474
DeepCCS	[M-H]-	149.345	30932474
DeepCCS	[M-2H]-	184.059	30932474
DeepCCS	[M+Na]+	159.2	30932474
AllCCS	[M+H]+	147.4	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	151.2	32859911
AllCCS	[M+Na]+	152.3	32859911
AllCCS	[M-H]-	153.8	32859911
AllCCS	[M+Na-2H]-	154.3	32859911
AllCCS	[M+HCOO]-	155.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol	CC1OC2(C)C=CCC(C)(C)C2=CC1O	2072.3	Standard polar	33892256
(5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol	CC1OC2(C)C=CCC(C)(C)C2=CC1O	1333.3	Standard non polar	33892256
(5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol	CC1OC2(C)C=CCC(C)(C)C2=CC1O	1460.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol,1TMS,isomer #1	CC1OC2(C)C=CCC(C)(C)C2=CC1O[Si](C)(C)C	1597.1	Semi standard non polar	33892256
(5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol,1TBDMS,isomer #1	CC1OC2(C)C=CCC(C)(C)C2=CC1O[Si](C)(C)C(C)(C)C	1864.0	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 - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-02be-1900000000-50673c77d967cfc1c572	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-4690000000-dd0cd6dd039bf7bfa9f9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 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 - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 10V, Positive-QTOF	splash10-0a4i-0390000000-8ac7fe8c998208a5d440	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 20V, Positive-QTOF	splash10-0a5c-4930000000-2073fdfbc1994b86b671	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 40V, Positive-QTOF	splash10-05nf-9300000000-92a339b50d461ea13ac0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 10V, Negative-QTOF	splash10-0a4i-0190000000-bee12e7ea7abadc20a69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 20V, Negative-QTOF	splash10-0a4i-1690000000-27e171ee63d59d44b349	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 40V, Negative-QTOF	splash10-0fki-2900000000-de405cc0ac99ba2c01b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 10V, Negative-QTOF	splash10-0a4i-0090000000-43a9bdbf7663e467c30d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 20V, Negative-QTOF	splash10-0a4i-0390000000-c96381353ab7a6076e38	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 40V, Negative-QTOF	splash10-0a4i-1970000000-b9acf1c5359ad8eea6b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 10V, Positive-QTOF	splash10-0a4i-0590000000-cd4f90b217f5ca6089a8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 20V, Positive-QTOF	splash10-0a4i-2960000000-df5b77f04e17aaa0a8ff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol 40V, Positive-QTOF	splash10-02vl-9200000000-da44e3b16e242295a855	2021-09-23	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

FDB013198

KNApSAcK ID

Not Available

Chemspider ID

35013768

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101415508

PDB ID

Not Available

ChEBI ID

167940

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 (5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol (HMDB0034672)

MOL for HMDB0034672 ((5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol)

3D MOL for HMDB0034672 ((5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol)

3D SDF for HMDB0034672 ((5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol)

3D-SDF for HMDB0034672 ((5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol)

PDB for HMDB0034672 ((5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol)

3D PDB for HMDB0034672 ((5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol)

SMILES for HMDB0034672 ((5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol)

INCHI for HMDB0034672 ((5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol)

Structure for HMDB0034672 ((5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol)

3D Structure for HMDB0034672 ((5alpha,8beta,9beta)-5,9-Epoxy-3,6-megastigmadien-8-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra