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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:59:40 UTC

Update Date

2022-03-07 02:55:04 UTC

HMDB ID

HMDB0036818

Secondary Accession Numbers

HMDB36818

Metabolite Identification

Common Name

Vitispirane

Description

Vitispirane belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Vitispirane is an earthy, floral, and fruity tasting compound. Vitispirane has been detected, but not quantified in, several different foods, such as alcoholic beverages, evergreen blackberries (Rubus laciniatus), common grapes (Vitis vinifera), blackberries (Rubus), and grape wine. This could make vitispirane a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vitispirane.

Structure

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

HMDB0036818
     RDKit          3D
Vitispirane
 34 35  0  0  0  0  0  0  0  0999 V2000
    0.6901    2.4406   -0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    1.6662   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3748    2.2877    0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096    1.5515    0.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    0.0857    0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2902   -0.5096   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055   -1.9670    0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0131   -0.4159   -1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0582    0.2047   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9114   -0.3353   -1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764   -0.4662   -0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0545   -0.0738    0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7907   -1.0830    1.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -0.1310    1.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102    3.4948   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    2.0075   -1.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5542    3.3543    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    2.0079    1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842   -0.3664    0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171   -0.1591    1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -2.0335    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8451   -2.5846   -0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566   -2.3115    0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254   -1.1112   -2.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298    0.6157   -1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -0.6673   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640   -1.3811   -1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9124    0.2835   -2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615    0.1409   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576   -1.5225   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3819    0.9622    1.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2960   -1.1147    2.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8614   -0.7877    1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7660   -2.0821    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  9  2  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
M  END

Vitispirane
  Mrv1572001071617102D          
  Mrv0541 01231311432D          
 14 15  0  0  0  0            999 V2000
    1.2695    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8253   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9068   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    1.1270    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
    1.6820   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  1  2  0  0  0  0
 10  6  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  1  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036818

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2(O1)C(=C)C=CCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O/c1-10-6-5-8-12(3,4)13(10)9-7-11(2)14-13/h5-6,11H,1,7-9H2,2-4H3

> <INCHI_KEY>
DUPDJVDPPBFBPL-UHFFFAOYSA-N

> <FORMULA>
C13H20O

> <MOLECULAR_WEIGHT>
192.302

> <EXACT_MASS>
192.151415264

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
22.83171455197106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,10,10-trimethyl-6-methylidene-1-oxaspiro[4.5]dec-7-ene

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
3.146293936666667

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.221549307460428

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
60.03450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,10,10-trimethyl-6-methylidene-1-oxaspiro[4.5]dec-7-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036818
     RDKit          3D
Vitispirane
 34 35  0  0  0  0  0  0  0  0999 V2000
    0.6901    2.4406   -0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    1.6662   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3748    2.2877    0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096    1.5515    0.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    0.0857    0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2902   -0.5096   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055   -1.9670    0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0131   -0.4159   -1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0582    0.2047   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9114   -0.3353   -1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764   -0.4662   -0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0545   -0.0738    0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7907   -1.0830    1.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -0.1310    1.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102    3.4948   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    2.0075   -1.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5542    3.3543    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    2.0079    1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842   -0.3664    0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171   -0.1591    1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -2.0335    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8451   -2.5846   -0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566   -2.3115    0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254   -1.1112   -2.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298    0.6157   -1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -0.6673   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640   -1.3811   -1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9124    0.2835   -2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615    0.1409   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576   -1.5225   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3819    0.9622    1.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2960   -1.1147    2.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8614   -0.7877    1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7660   -2.0821    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  9  2  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Vitispirane                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       2.370   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.407  -2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.693  -1.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.450   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.140   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.465   2.016   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7    9   11                                                       
CONECT    8    5   12                                                       
CONECT    9    7   13                                                       
CONECT   10    1    6   13                                                  
CONECT   11    2    7   14                                                  
CONECT   12    3    4    8   13                                             
CONECT   13    9   10   12   14                                             
CONECT   14   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0036818
HETATM    1  C1  UNL     1       0.690   2.441  -0.901  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.175   1.666  -0.286  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.375   2.288   0.257  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.310   1.551   0.834  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.175   0.086   0.949  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.290  -0.510  -0.122  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.105  -1.967   0.237  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.013  -0.416  -1.427  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.058   0.205  -0.147  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.911  -0.335  -1.230  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.276  -0.466  -0.624  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.054  -0.074   0.802  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.791  -1.083   1.675  1.00  0.00           C  
HETATM   14  O1  UNL     1       0.683  -0.131   1.024  1.00  0.00           O  
HETATM   15  H1  UNL     1       0.510   3.495  -0.994  1.00  0.00           H  
HETATM   16  H2  UNL     1       1.595   2.008  -1.317  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.554   3.354   0.216  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.192   2.008   1.234  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.184  -0.366   0.847  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.717  -0.159   1.928  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.329  -2.033   1.042  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.845  -2.585  -0.642  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.057  -2.312   0.695  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.625  -1.111  -2.200  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.030   0.616  -1.830  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.094  -0.667  -1.214  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.564  -1.381  -1.491  1.00  0.00           H  
HETATM   28  H14 UNL     1       0.912   0.284  -2.156  1.00  0.00           H  
HETATM   29  H15 UNL     1       3.061   0.141  -1.124  1.00  0.00           H  
HETATM   30  H16 UNL     1       2.658  -1.523  -0.715  1.00  0.00           H  
HETATM   31  H17 UNL     1       2.382   0.962   1.040  1.00  0.00           H  
HETATM   32  H18 UNL     1       2.296  -1.115   2.674  1.00  0.00           H  
HETATM   33  H19 UNL     1       3.861  -0.788   1.766  1.00  0.00           H  
HETATM   34  H20 UNL     1       2.766  -2.082   1.199  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3    9
CONECT    3    4    4   17
CONECT    4    5   18
CONECT    5    6   19   20
CONECT    6    7    8    9
CONECT    7   21   22   23
CONECT    8   24   25   26
CONECT    9   10   14
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   14   31
CONECT   13   32   33   34
END

HMDB0036818
     RDKit          3D
Vitispirane
 34 35  0  0  0  0  0  0  0  0999 V2000
    0.6901    2.4406   -0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    1.6662   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3748    2.2877    0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096    1.5515    0.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    0.0857    0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2902   -0.5096   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055   -1.9670    0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0131   -0.4159   -1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0582    0.2047   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9114   -0.3353   -1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764   -0.4662   -0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0545   -0.0738    0.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7907   -1.0830    1.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -0.1310    1.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102    3.4948   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    2.0075   -1.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5542    3.3543    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    2.0079    1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842   -0.3664    0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171   -0.1591    1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -2.0335    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8451   -2.5846   -0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566   -2.3115    0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254   -1.1112   -2.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298    0.6157   -1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -0.6673   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640   -1.3811   -1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9124    0.2835   -2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615    0.1409   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576   -1.5225   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3819    0.9622    1.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2960   -1.1147    2.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8614   -0.7877    1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7660   -2.0821    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  9  2  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,10,10-Trimethyl-6-methylidene-1-oxaspiro[4.5]dec-7-ene	HMDB
6,9-Epoxy-3,5(13)-megastigmadiene	HMDB

Chemical Formula

C₁₃H₂₀O

Average Molecular Weight

192.302

Monoisotopic Molecular Weight

192.151415264

IUPAC Name

2,10,10-trimethyl-6-methylidene-1-oxaspiro[4.5]dec-7-ene

Traditional Name

2,10,10-trimethyl-6-methylidene-1-oxaspiro[4.5]dec-7-ene

CAS Registry Number

65416-59-3

SMILES

CC1CCC2(O1)C(=C)C=CCC2(C)C

InChI Identifier

InChI=1S/C13H20O/c1-10-6-5-8-12(3,4)13(10)9-7-11(2)14-13/h5-6,11H,1,7-9H2,2-4H3

InChI Key

DUPDJVDPPBFBPL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	49.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	258.00 to 259.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	5.08 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.619 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	4.25	ALOGPS
logP	3.15	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	60.03 m³·mol⁻¹	ChemAxon
Polarizability	22.83 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]+	146.13	31661259
DarkChem	[M-H]-	145.337	31661259
DeepCCS	[M+H]+	148.811	30932474
DeepCCS	[M-H]-	146.453	30932474
DeepCCS	[M-2H]-	180.478	30932474
DeepCCS	[M+Na]+	155.291	30932474
AllCCS	[M+H]+	142.9	32859911
AllCCS	[M+H-H2O]+	138.7	32859911
AllCCS	[M+NH4]+	146.9	32859911
AllCCS	[M+Na]+	148.0	32859911
AllCCS	[M-H]-	150.7	32859911
AllCCS	[M+Na-2H]-	151.3	32859911
AllCCS	[M+HCOO]-	152.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vitispirane	CC1CCC2(O1)C(=C)C=CCC2(C)C	1505.9	Standard polar	33892256
Vitispirane	CC1CCC2(O1)C(=C)C=CCC2(C)C	1285.1	Standard non polar	33892256
Vitispirane	CC1CCC2(O1)C(=C)C=CCC2(C)C	1331.9	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 - Vitispirane GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gv-2900000000-2739a1eb76ca5414d126	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitispirane 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 - Vitispirane 10V, Positive-QTOF	splash10-0006-1900000000-744c2618d9fcad65a6eb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 20V, Positive-QTOF	splash10-00kf-6900000000-eda4218a528077619319	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 40V, Positive-QTOF	splash10-0gb9-9100000000-0940e73441b1b0b4f7ee	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 10V, Negative-QTOF	splash10-0006-0900000000-593d1022019da0a50f12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 20V, Negative-QTOF	splash10-0006-0900000000-e5d36e0a67335cf33415	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 40V, Negative-QTOF	splash10-0a70-3900000000-57f58811e3bfef9b8148	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 10V, Positive-QTOF	splash10-0006-0900000000-9cc3e24333b35d1cc976	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 20V, Positive-QTOF	splash10-000l-5900000000-868d984a13f8e20c1337	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 40V, Positive-QTOF	splash10-000i-9500000000-1e1f155e383051c8cb17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 10V, Negative-QTOF	splash10-0006-0900000000-14436e4d9ff8d032db54	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 20V, Negative-QTOF	splash10-0006-0900000000-f2d4c7e0561b1f59c4d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitispirane 40V, Negative-QTOF	splash10-02tl-4900000000-f45993d01a55623763bf	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	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

FDB015765

KNApSAcK ID

C00058171

Chemspider ID

4953381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6450832

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1065661

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 Vitispirane (HMDB0036818)

MOL for HMDB0036818 (Vitispirane)

3D MOL for HMDB0036818 (Vitispirane)

3D SDF for HMDB0036818 (Vitispirane)

3D-SDF for HMDB0036818 (Vitispirane)

PDB for HMDB0036818 (Vitispirane)

3D PDB for HMDB0036818 (Vitispirane)

SMILES for HMDB0036818 (Vitispirane)

INCHI for HMDB0036818 (Vitispirane)

Structure for HMDB0036818 (Vitispirane)

3D Structure for HMDB0036818 (Vitispirane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra