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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:46:11 UTC

Update Date

2022-03-07 02:56:31 UTC

HMDB ID

HMDB0040233

Secondary Accession Numbers

HMDB40233

Metabolite Identification

Common Name

2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one

Description

2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 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. 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one has been detected, but not quantified in, alcoholic beverages and fruits. This could make 2,3,5,6,8,8a-hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one.

Structure

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

HMDB0040233
     RDKit          3D
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one
 35 36  0  0  0  0  0  0  0  0999 V2000
    3.8549    0.6230   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3443    0.5367   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510    1.7705   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2968    1.5542    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751    0.3571    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390    0.2786    0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2614    1.4903    1.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    0.1555   -0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1034   -0.9323    1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3059   -2.1070    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796   -3.1066    0.3674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805   -1.9594    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5646   -0.8508   -0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010   -1.3816   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9137   -0.5700    0.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1642    1.5858   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2530   -0.1825    0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3675    0.5817   -1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    0.4320   -1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339    1.8912    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325    2.6760   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3134    2.4557    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    1.7026    1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1734    1.2186    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221    2.3591    0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2886   -0.7572   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5851    0.1329   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3638    1.0117   -1.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -1.0975    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711   -0.6795    2.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6996   -2.8907    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4598   -1.6585    1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049   -0.6445   -2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3950   -1.6936   -1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -2.3014   -1.6085 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15  2  1  0
 13  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
M  END


  Mrv0541 05061311422D          

 15 16  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    3.5724    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
    2.8579    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
    4.2868    2.4750    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
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  2  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  2  0  0  0  0
 15  9  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040233

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC=C2C(C)(C)CC(=O)CC2(C)O1

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

> <INCHI_KEY>
PYUYJSFTZPYHDW-UHFFFAOYSA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.901773859143123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,5,8a-tetramethyl-3,5,6,7,8,8a-hexahydro-2H-1-benzopyran-7-one

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.1931104676666666

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.998135056625795

> <JCHEM_PKA_STRONGEST_BASIC>
-4.21868563013397

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
60.708800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5,5,8a-tetramethyl-2,3,6,8-tetrahydro-1-benzopyran-7-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0040233
     RDKit          3D
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one
 35 36  0  0  0  0  0  0  0  0999 V2000
    3.8549    0.6230   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3443    0.5367   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510    1.7705   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2968    1.5542    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751    0.3571    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390    0.2786    0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2614    1.4903    1.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    0.1555   -0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1034   -0.9323    1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3059   -2.1070    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796   -3.1066    0.3674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805   -1.9594    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5646   -0.8508   -0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010   -1.3816   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9137   -0.5700    0.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1642    1.5858   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2530   -0.1825    0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3675    0.5817   -1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    0.4320   -1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339    1.8912    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325    2.6760   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3134    2.4557    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    1.7026    1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1734    1.2186    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221    2.3591    0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2886   -0.7572   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5851    0.1329   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3638    1.0117   -1.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -1.0975    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711   -0.6795    2.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6996   -2.8907    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4598   -1.6585    1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049   -0.6445   -2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3950   -1.6936   -1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -2.3014   -1.6085 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15  2  1  0
 13  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.325   0.360   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.345   0.360   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002   4.620   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    9                                                       
CONECT    6    5   11                                                       
CONECT    7   10   12                                                       
CONECT    8   10   13                                                       
CONECT    9    1    5   15                                                  
CONECT   10    7    8   14                                                  
CONECT   11    6   12   13                                                  
CONECT   12    2    3    7   11                                             
CONECT   13    4    8   11   15                                             
CONECT   14   10                                                            
CONECT   15    9   13                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0040233
HETATM    1  C1  UNL     1       3.855   0.623  -0.494  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.344   0.537  -0.664  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.751   1.771  -0.044  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.297   1.554   0.143  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.275   0.357   0.086  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.739   0.279   0.291  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.261   1.490   1.046  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.500   0.156  -0.987  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.103  -0.932   1.159  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.306  -2.107   0.731  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.880  -3.107   0.367  1.00  0.00           O  
HETATM   12  C11 UNL     1       0.180  -1.959   0.783  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.565  -0.851  -0.176  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.401  -1.382  -1.570  1.00  0.00           C  
HETATM   15  O2  UNL     1       1.914  -0.570   0.060  1.00  0.00           O  
HETATM   16  H1  UNL     1       4.164   1.586  -0.045  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.253  -0.183   0.138  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.367   0.582  -1.492  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.066   0.432  -1.737  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.234   1.891   0.965  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.933   2.676  -0.658  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.313   2.456   0.337  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.480   1.703   1.833  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.173   1.219   1.622  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.422   2.359   0.398  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.289  -0.757  -1.555  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.585   0.133  -0.731  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.364   1.012  -1.666  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.188  -1.098   1.121  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.771  -0.679   2.191  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.700  -2.891   0.483  1.00  0.00           H  
HETATM   32  H17 UNL     1       0.460  -1.658   1.816  1.00  0.00           H  
HETATM   33  H18 UNL     1      -0.005  -0.645  -2.286  1.00  0.00           H  
HETATM   34  H19 UNL     1       1.395  -1.694  -1.998  1.00  0.00           H  
HETATM   35  H20 UNL     1      -0.224  -2.301  -1.608  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   15   19
CONECT    3    4   20   21
CONECT    4    5    5   22
CONECT    5    6   13
CONECT    6    7    8    9
CONECT    7   23   24   25
CONECT    8   26   27   28
CONECT    9   10   29   30
CONECT   10   11   11   12
CONECT   12   13   31   32
CONECT   13   14   15
CONECT   14   33   34   35
END

HMDB0040233
     RDKit          3D
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one
 35 36  0  0  0  0  0  0  0  0999 V2000
    3.8549    0.6230   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3443    0.5367   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510    1.7705   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2968    1.5542    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751    0.3571    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390    0.2786    0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2614    1.4903    1.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    0.1555   -0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1034   -0.9323    1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3059   -2.1070    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796   -3.1066    0.3674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805   -1.9594    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5646   -0.8508   -0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010   -1.3816   -1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9137   -0.5700    0.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1642    1.5858   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2530   -0.1825    0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3675    0.5817   -1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    0.4320   -1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339    1.8912    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325    2.6760   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3134    2.4557    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    1.7026    1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1734    1.2186    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221    2.3591    0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2886   -0.7572   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5851    0.1329   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3638    1.0117   -1.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -1.0975    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711   -0.6795    2.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6996   -2.8907    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4598   -1.6585    1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049   -0.6445   -2.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3950   -1.6936   -1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -2.3014   -1.6085 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15  2  1  0
 13  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 12 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
3,4-dihydro-3-Oxoedulan	HMDB

Chemical Formula

C₁₃H₂₀O₂

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

IUPAC Name

2,5,5,8a-tetramethyl-3,5,6,7,8,8a-hexahydro-2H-1-benzopyran-7-one

Traditional Name

2,5,5,8a-tetramethyl-2,3,6,8-tetrahydro-1-benzopyran-7-one

CAS Registry Number

20194-67-6

SMILES

CC1CC=C2C(C)(C)CC(=O)CC2(C)O1

InChI Identifier

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

InChI Key

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040233)
Cell membrane (HMDB: HMDB0040233)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040233)

Source

Exogenous

Exogenous (HMDB: HMDB0040233)

Food

Food (HMDB: HMDB0040233)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0040233)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040233)

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.51 g/L	ALOGPS
logP	3.07	ALOGPS
logP	2.19	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	19	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	60.71 m³·mol⁻¹	ChemAxon
Polarizability	23.9 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]+	149.817	31661259
DarkChem	[M-H]-	145.705	31661259
DeepCCS	[M+H]+	152.723	30932474
DeepCCS	[M-H]-	150.365	30932474
DeepCCS	[M-2H]-	184.42	30932474
DeepCCS	[M+Na]+	159.593	30932474
AllCCS	[M+H]+	146.9	32859911
AllCCS	[M+H-H2O]+	142.8	32859911
AllCCS	[M+NH4]+	150.6	32859911
AllCCS	[M+Na]+	151.7	32859911
AllCCS	[M-H]-	154.5	32859911
AllCCS	[M+Na-2H]-	155.0	32859911
AllCCS	[M+HCOO]-	155.8	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.	5.27 minutes	32390414
Predicted by Siyang on May 30, 2022	16.14 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.73 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2317.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	488.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	268.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	137.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	695.7 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	719.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1219.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	442.9 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	1394.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	446.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	390.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	492.2 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one	CC1CC=C2C(C)(C)CC(=O)CC2(C)O1	2104.4	Standard polar	33892256
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one	CC1CC=C2C(C)(C)CC(=O)CC2(C)O1	1448.4	Standard non polar	33892256
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one	CC1CC=C2C(C)(C)CC(=O)CC2(C)O1	1478.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one,1TMS,isomer #1	CC1CC=C2C(C)(C)CC(O[Si](C)(C)C)=CC2(C)O1	1651.3	Semi standard non polar	33892256
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one,1TMS,isomer #1	CC1CC=C2C(C)(C)CC(O[Si](C)(C)C)=CC2(C)O1	1530.3	Standard non polar	33892256
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one,1TMS,isomer #2	CC1CC=C2C(C)(C)C=C(O[Si](C)(C)C)CC2(C)O1	1629.4	Semi standard non polar	33892256
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one,1TMS,isomer #2	CC1CC=C2C(C)(C)C=C(O[Si](C)(C)C)CC2(C)O1	1574.6	Standard non polar	33892256
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one,1TBDMS,isomer #1	CC1CC=C2C(C)(C)CC(O[Si](C)(C)C(C)(C)C)=CC2(C)O1	1923.7	Semi standard non polar	33892256
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one,1TBDMS,isomer #1	CC1CC=C2C(C)(C)CC(O[Si](C)(C)C(C)(C)C)=CC2(C)O1	1758.6	Standard non polar	33892256
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one,1TBDMS,isomer #2	CC1CC=C2C(C)(C)C=C(O[Si](C)(C)C(C)(C)C)CC2(C)O1	1888.8	Semi standard non polar	33892256
2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one,1TBDMS,isomer #2	CC1CC=C2C(C)(C)C=C(O[Si](C)(C)C(C)(C)C)CC2(C)O1	1801.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0wt9-1900000000-5fb27da915f579be0e4d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-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 - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 10V, Positive-QTOF	splash10-0a4i-0490000000-1ba6f5b7812e077d7ac5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 20V, Positive-QTOF	splash10-0aor-3920000000-d14d417115aa1c9bde3c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 40V, Positive-QTOF	splash10-0pbc-9600000000-619dd413880e79e55e69	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 10V, Negative-QTOF	splash10-0a4i-0090000000-dfb742e2a3be2ceb4621	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 20V, Negative-QTOF	splash10-0a4i-0190000000-5c0936adb44d2f43b05c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 40V, Negative-QTOF	splash10-0a4i-9700000000-90867c9fccfa1e38da8f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 10V, Positive-QTOF	splash10-0a4i-0590000000-9de79424715997bee799	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 20V, Positive-QTOF	splash10-01z9-8900000000-5558f86d51bebaf3783d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 40V, Positive-QTOF	splash10-00kb-9800000000-81b30ef091d2e67c823b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 10V, Negative-QTOF	splash10-0a4i-0090000000-43a9bdbf7663e467c30d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 20V, Negative-QTOF	splash10-0a4i-0090000000-ac23213061ed0fcba5e9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 40V, Negative-QTOF	splash10-0a4i-2920000000-19ee273a89e765e872fb	2021-09-25	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

FDB019948

KNApSAcK ID

C00054418

Chemspider ID

470508

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

540316

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1882381

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 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one (HMDB0040233)

MOL for HMDB0040233 (2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one)

3D MOL for HMDB0040233 (2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one)

3D SDF for HMDB0040233 (2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one)

3D-SDF for HMDB0040233 (2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one)

PDB for HMDB0040233 (2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one)

3D PDB for HMDB0040233 (2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one)

SMILES for HMDB0040233 (2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one)

INCHI for HMDB0040233 (2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one)

Structure for HMDB0040233 (2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one)

3D Structure for HMDB0040233 (2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra