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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:48 UTC

Update Date

2022-03-07 02:52:57 UTC

HMDB ID

HMDB0031387

Secondary Accession Numbers

HMDB31387

Metabolite Identification

Common Name

(1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide

Description

(1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide has been detected, but not quantified in, herbs and spices. This could make (1beta,4E,8beta,10alpha)-1,10-epoxy-4,11(13)-germacradien-12,8-olide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide.

Structure

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

HMDB0031387
     RDKit          3D
(1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.5605   -1.7490    0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8680   -0.8305    0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3703    0.0481   -0.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839   -0.0092   -1.5404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868    1.0119   -1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1433    0.3346   -0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0489    1.3295   -0.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072    1.9877    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2831    3.4014    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4755    1.3619    1.5778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    1.7907    0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680    0.6608    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -0.6946    0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6321   -1.5657   -0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7195   -1.8908   -1.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4023   -2.0278   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -1.7508    0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.4586    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943   -1.9544    0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0592   -2.3301    1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0178   -0.3403   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3756    2.1457   -1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8204    0.8964   -1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1107    3.9950   -0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    3.3806    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591    3.8625    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224    2.6337    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790    0.6873   -0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682    0.7587    0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   -0.5039    1.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6712   -1.2597    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -1.9156   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5975   -2.9040   -1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277   -1.1395   -2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2364   -2.6707   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3947   -2.6498    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.7942    1.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576    0.1528    1.2391 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
  3  5  1  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
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 11  8  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END


  Mrv0541 05061305552D          

 18 20  0  0  0  0            999 V2000
    3.4884   -1.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3704    0.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9097    2.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3482   -0.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7829   -0.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795   -0.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3469    0.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7380    1.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5473   -1.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7392    0.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9384    0.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5024    1.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058    0.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    1.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9372    1.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4985    2.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0337    1.9799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1249    1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  2  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 15  3  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031387

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C\CC2C(CC3(C)OC3CC1)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-4-6-11-10(2)14(16)17-12(11)8-15(3)13(18-15)7-5-9/h4,11-13H,2,5-8H2,1,3H3/b9-4-

> <INCHI_KEY>
ACDBVOJKXAGTJM-WTKPLQERSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.03210898137457

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8Z)-3,8-dimethyl-12-methylidene-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.686683672333333

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2241583989223805

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
68.8173

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8Z)-3,8-dimethyl-12-methylidene-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0031387
     RDKit          3D
(1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.5605   -1.7490    0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8680   -0.8305    0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3703    0.0481   -0.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839   -0.0092   -1.5404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868    1.0119   -1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1433    0.3346   -0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0489    1.3295   -0.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072    1.9877    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2831    3.4014    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4755    1.3619    1.5778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    1.7907    0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680    0.6608    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -0.6946    0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6321   -1.5657   -0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7195   -1.8908   -1.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4023   -2.0278   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -1.7508    0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.4586    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943   -1.9544    0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0592   -2.3301    1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0178   -0.3403   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3756    2.1457   -1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8204    0.8964   -1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1107    3.9950   -0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    3.3806    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591    3.8625    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224    2.6337    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790    0.6873   -0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682    0.7587    0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   -0.5039    1.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6712   -1.2597    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -1.9156   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5975   -2.9040   -1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277   -1.1395   -2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2364   -2.6707   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3947   -2.6498    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.7942    1.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576    0.1528    1.2391 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
  3  5  1  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
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 11  8  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  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       6.512  -3.410   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.891   0.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.431   4.266   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.117  -1.504   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.195  -1.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.108  -0.326   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.381   0.013   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.978   3.097   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.622  -1.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.713   1.581   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.218   1.211   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.404   2.518   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.491   1.549   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.823   3.117   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.483   2.727   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.131   3.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.396   3.696   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.966   2.997   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   11                                                       
CONECT    7    5   13                                                       
CONECT    8   12   15                                                       
CONECT    9    1    4    5                                                  
CONECT   10    2   11   14                                                  
CONECT   11    6   10   12                                                  
CONECT   12    8   11   17                                                  
CONECT   13    7   15   18                                                  
CONECT   14   10   16   17                                                  
CONECT   15    3    8   13   18                                             
CONECT   16   14                                                            
CONECT   17   12   14                                                       
CONECT   18   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0031387
HETATM    1  C1  UNL     1       3.561  -1.749   0.755  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.868  -0.831   0.114  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.370   0.048  -0.931  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.484  -0.009  -1.540  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.387   1.012  -1.171  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.143   0.335  -0.898  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.049   1.330  -0.894  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.307   1.988   0.375  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.283   3.401   0.566  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.475   1.362   1.578  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.618   1.791   0.917  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.468   0.661   0.419  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.924  -0.695   0.870  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.632  -1.566  -0.299  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.719  -1.891  -1.277  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.402  -2.028  -0.431  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.694  -1.751   0.482  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.436  -0.459   0.285  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.594  -1.954   0.573  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.059  -2.330   1.513  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.018  -0.340  -1.770  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.376   2.146  -1.620  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.820   0.896  -1.466  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.111   3.995  -0.304  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.370   3.381   0.543  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.159   3.862   1.463  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.122   2.634   1.446  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.679   0.687  -0.663  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.468   0.759   0.918  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.073  -0.504   1.514  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.671  -1.260   1.488  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.662  -1.916  -0.684  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.598  -2.904  -1.712  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.828  -1.139  -2.062  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.236  -2.671  -1.320  1.00  0.00           H  
HETATM   36  H18 UNL     1       1.395  -2.650   0.406  1.00  0.00           H  
HETATM   37  H19 UNL     1       0.429  -1.794   1.578  1.00  0.00           H  
HETATM   38  H20 UNL     1       1.458   0.153   1.239  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3   18
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   21
CONECT    7    8   22   23
CONECT    8    9   10   11
CONECT    9   24   25   26
CONECT   10   11
CONECT   11   12   27
CONECT   12   13   28   29
CONECT   13   14   30   31
CONECT   14   15   16   16
CONECT   15   32   33   34
CONECT   16   17   35
CONECT   17   18   36   37
CONECT   18   38
END

HMDB0031387
     RDKit          3D
(1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.5605   -1.7490    0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8680   -0.8305    0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3703    0.0481   -0.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839   -0.0092   -1.5404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868    1.0119   -1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1433    0.3346   -0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0489    1.3295   -0.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072    1.9877    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2831    3.4014    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4755    1.3619    1.5778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    1.7907    0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680    0.6608    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -0.6946    0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6321   -1.5657   -0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7195   -1.8908   -1.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4023   -2.0278   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -1.7508    0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.4586    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943   -1.9544    0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0592   -2.3301    1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0178   -0.3403   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3756    2.1457   -1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8204    0.8964   -1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1107    3.9950   -0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    3.3806    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591    3.8625    1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224    2.6337    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790    0.6873   -0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682    0.7587    0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   -0.5039    1.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6712   -1.2597    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -1.9156   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5975   -2.9040   -1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277   -1.1395   -2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2364   -2.6707   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3947   -2.6498    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.7942    1.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576    0.1528    1.2391 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
  3  5  1  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
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 11  8  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1b,4E,8b,10a)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide	Generator
(1Β,4E,8β,10α)-1,10-epoxy-4,11(13)-germacradien-12,8-olide	Generator

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

(8Z)-3,8-dimethyl-12-methylidene-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one

Traditional Name

(8Z)-3,8-dimethyl-12-methylidene-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one

CAS Registry Number

Not Available

SMILES

C\C1=C\CC2C(CC3(C)OC3CC1)OC(=O)C2=C

InChI Identifier

InChI=1S/C15H20O3/c1-9-4-6-11-10(2)14(16)17-12(11)8-15(3)13(18-15)7-5-9/h4,11-13H,2,5-8H2,1,3H3/b9-4-

InChI Key

ACDBVOJKXAGTJM-WTKPLQERSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031387)

Source

Endogenous

Endogenous (HMDB: HMDB0031387)

Plant

Plant (HMDB: HMDB0031387)

Exogenous

Food

Food (HMDB: HMDB0031387)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0031387)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0031387)

Role

Biological role

Energy source (HMDB: HMDB0031387)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031387)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	156 °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	0.2 g/L	ALOGPS
logP	2.95	ALOGPS
logP	2.69	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.82 m³·mol⁻¹	ChemAxon
Polarizability	27.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	158.284	31661259
DarkChem	[M-H]-	151.524	31661259
DeepCCS	[M+H]+	160.328	30932474
DeepCCS	[M-H]-	157.97	30932474
DeepCCS	[M-2H]-	190.856	30932474
DeepCCS	[M+Na]+	166.421	30932474
AllCCS	[M+H]+	159.3	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	164.2	32859911
AllCCS	[M+HCOO]-	164.3	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.	5.79 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0711 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.02 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2605.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	415.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	659.1 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	705.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1267.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	405.7 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	1303.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	485.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	423.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	475.1 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	30.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide	C\C1=C\CC2C(CC3(C)OC3CC1)OC(=O)C2=C	2674.6	Standard polar	33892256
(1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide	C\C1=C\CC2C(CC3(C)OC3CC1)OC(=O)C2=C	1895.0	Standard non polar	33892256
(1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide	C\C1=C\CC2C(CC3(C)OC3CC1)OC(=O)C2=C	2162.2	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 - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-6970000000-cc19ae8c2e048285a431	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 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 - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 10V, Positive-QTOF	splash10-0002-0190000000-65e2e4d65c4f84d4ff03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 20V, Positive-QTOF	splash10-0032-1690000000-f687d051f03a50eea27e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 40V, Positive-QTOF	splash10-0v03-9300000000-4c6e26bca9c185c8fc96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 10V, Negative-QTOF	splash10-0002-0090000000-bc4f63b7234e3b15d7b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 20V, Negative-QTOF	splash10-0f6t-0190000000-ecce73740b2212ea4e7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 40V, Negative-QTOF	splash10-0v00-9310000000-eafe14a0dd744ab8d368	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 10V, Positive-QTOF	splash10-0002-0090000000-aeb59e3dd1cb41c700e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 20V, Positive-QTOF	splash10-000t-0190000000-c50169a60cefa72255eb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 40V, Positive-QTOF	splash10-0m1r-1960000000-dc2cdab8b423c00a72ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 20V, Negative-QTOF	splash10-0002-3090000000-d48a400fcf2399e84d58	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide 40V, Negative-QTOF	splash10-004i-2490000000-3504ddda1737a0d041e0	2021-09-25	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

FDB003454

KNApSAcK ID

Not Available

Chemspider ID

35013359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751164

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 (1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide (HMDB0031387)

MOL for HMDB0031387 ((1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide)

3D MOL for HMDB0031387 ((1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide)

3D SDF for HMDB0031387 ((1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide)

3D-SDF for HMDB0031387 ((1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide)

PDB for HMDB0031387 ((1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide)

3D PDB for HMDB0031387 ((1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide)

SMILES for HMDB0031387 ((1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide)

INCHI for HMDB0031387 ((1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide)

Structure for HMDB0031387 ((1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide)

3D Structure for HMDB0031387 ((1beta,4E,8beta,10alpha)-1,10-Epoxy-4,11(13)-germacradien-12,8-olide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra