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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:47 UTC

Update Date

2022-03-07 02:52:57 UTC

HMDB ID

HMDB0031386

Secondary Accession Numbers

HMDB31386

Metabolite Identification

Common Name

(1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide

Description

(1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide.

Structure

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

HMDB0031386
     RDKit          3D
(1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.3796   -2.0315   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470   -0.8300   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764    0.4192   -0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8131    0.5401    0.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407    1.4050   -0.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770    0.9309   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407    1.6861   -0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    2.2013    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5109    3.3862    0.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0370    1.7460    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4553    0.5925   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -0.5744   -0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7985   -1.8770   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2428   -1.8390    1.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -3.0863   -0.3235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253   -2.3842   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5489   -1.4871    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894   -0.5308   -0.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4576   -2.1690   -0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -2.9360   -0.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955    1.1151    1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092    2.6210   -1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070    1.2331   -1.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4106    3.9064    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3339    4.1336    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3842    3.0550    1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7980    2.2127    0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4940    0.3144   -0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6283    1.0218   -1.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289   -0.2115    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256   -0.7170   -1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5891   -0.8180    1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181   -2.5324    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515   -2.2039    2.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088   -2.3276   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747   -1.1126    1.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3262   -2.2402    0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -0.6119   -1.4743 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 16 13  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
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 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
    3.0985   -0.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498    3.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970    1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973   -0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8617   -0.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6612    0.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1938    0.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523    2.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -0.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3481    2.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167    1.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2528    1.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2515    2.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125    2.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7202    1.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8129    2.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0536    1.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4393    2.1532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  2  2  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  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>
HMDB0031386

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C\CCC2(C)OC2CC2C(C1)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-5-4-6-15(3)13(18-15)8-11-10(2)14(16)17-12(11)7-9/h5,11-13H,2,4,6-8H2,1,3H3/b9-5-

> <INCHI_KEY>
RYQABBMOWVCVPW-UITAMQMPSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.896015071543516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8Z)-5,9-dimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.759477678333333

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.223623642520871

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
68.8609

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8Z)-5,9-dimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0031386
     RDKit          3D
(1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.3796   -2.0315   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470   -0.8300   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764    0.4192   -0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8131    0.5401    0.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407    1.4050   -0.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770    0.9309   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407    1.6861   -0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    2.2013    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5109    3.3862    0.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0370    1.7460    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4553    0.5925   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -0.5744   -0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7985   -1.8770   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2428   -1.8390    1.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -3.0863   -0.3235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253   -2.3842   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5489   -1.4871    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894   -0.5308   -0.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4576   -2.1690   -0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -2.9360   -0.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955    1.1151    1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092    2.6210   -1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070    1.2331   -1.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4106    3.9064    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3339    4.1336    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3842    3.0550    1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7980    2.2127    0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4940    0.3144   -0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6283    1.0218   -1.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289   -0.2115    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256   -0.7170   -1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5891   -0.8180    1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181   -2.5324    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515   -2.2039    2.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088   -2.3276   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747   -1.1126    1.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3262   -2.2402    0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -0.6119   -1.4743 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 16 13  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
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 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       5.784  -1.789   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.880   6.213   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.181   2.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.048  -0.272   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.475  -0.851   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.234   1.035   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.962   0.697   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.831   4.119   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.970  -0.481   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.250   4.718   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.258   3.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.072   2.233   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.336   3.749   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.677   4.139   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.344   2.571   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.984   4.953   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.567   2.603   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.820   4.019   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   15                                                       
CONECT    7    9   12                                                       
CONECT    8   11   13                                                       
CONECT    9    1    5    7                                                  
CONECT   10    2   11   14                                                  
CONECT   11    8   10   12                                                  
CONECT   12    7   11   17                                                  
CONECT   13    8   15   18                                                  
CONECT   14   10   16   17                                                  
CONECT   15    3    6   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    HMDB0031386
HETATM    1  C1  UNL     1       3.380  -2.031  -0.389  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.847  -0.830  -0.320  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.576   0.419  -0.184  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.813   0.540   0.089  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.641   1.405  -0.413  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.377   0.931  -0.065  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.241   1.686  -0.801  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.811   2.201   0.021  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.511   3.386   0.922  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.037   1.746   0.082  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.455   0.593  -0.742  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.632  -0.574  -0.742  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.799  -1.877  -0.118  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.243  -1.839   1.364  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.386  -3.086  -0.324  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.325  -2.384  -0.358  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.549  -1.487   0.437  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.389  -0.531  -0.369  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.458  -2.169  -0.346  1.00  0.00           H  
HETATM   20  H2  UNL     1       2.800  -2.936  -0.490  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.195   1.115   1.006  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.809   2.621  -1.166  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.007   1.233  -1.771  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.411   3.906   0.588  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.334   4.134   0.848  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.384   3.055   1.962  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.798   2.213   0.752  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.494   0.314  -0.420  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.628   1.022  -1.775  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.929  -0.211   0.043  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.226  -0.717  -1.756  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.589  -0.818   1.633  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.118  -2.532   1.476  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.451  -2.204   2.024  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.009  -2.328  -1.451  1.00  0.00           H  
HETATM   36  H18 UNL     1       0.175  -1.113   1.394  1.00  0.00           H  
HETATM   37  H19 UNL     1       1.326  -2.240   0.831  1.00  0.00           H  
HETATM   38  H20 UNL     1       1.147  -0.612  -1.474  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   10
CONECT    9   24   25   26
CONECT   10   11   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   15   16
CONECT   14   32   33   34
CONECT   15   16
CONECT   16   17   35
CONECT   17   18   36   37
CONECT   18   38
END

HMDB0031386
     RDKit          3D
(1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.3796   -2.0315   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470   -0.8300   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764    0.4192   -0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8131    0.5401    0.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407    1.4050   -0.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770    0.9309   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407    1.6861   -0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    2.2013    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5109    3.3862    0.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0370    1.7460    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4553    0.5925   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -0.5744   -0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7985   -1.8770   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2428   -1.8390    1.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -3.0863   -0.3235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253   -2.3842   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5489   -1.4871    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894   -0.5308   -0.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4576   -2.1690   -0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -2.9360   -0.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955    1.1151    1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092    2.6210   -1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070    1.2331   -1.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4106    3.9064    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3339    4.1336    0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3842    3.0550    1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7980    2.2127    0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4940    0.3144   -0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6283    1.0218   -1.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289   -0.2115    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256   -0.7170   -1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5891   -0.8180    1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181   -2.5324    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515   -2.2039    2.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088   -2.3276   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747   -1.1126    1.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3262   -2.2402    0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -0.6119   -1.4743 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 16 13  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
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 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
(1(10)e,4b,5a,8b)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide	Generator
(1(10)e,4Β,5α,8β)-4,5-epoxy-1(10),11(13)-germacradien-12,8-olide	Generator

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

(8Z)-5,9-dimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one

Traditional Name

(8Z)-5,9-dimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one

CAS Registry Number

68776-52-3

SMILES

C\C1=C\CCC2(C)OC2CC2C(C1)OC(=O)C2=C

InChI Identifier

InChI=1S/C15H20O3/c1-9-5-4-6-15(3)13(18-15)8-11-10(2)14(16)17-12(11)7-9/h5,11-13H,2,4,6-8H2,1,3H3/b9-5-

InChI Key

RYQABBMOWVCVPW-UITAMQMPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
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: HMDB0031386)

Source

Endogenous

Endogenous (HMDB: HMDB0031386)

Plant

Plant (HMDB: HMDB0031386)

Animal

Animal (HMDB: HMDB0031386)

Exogenous

Food

Food (HMDB: HMDB0031386)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0031386)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031386)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031386)

Lipid metabolism pathway (HMDB: HMDB0031386)

Cellular process

Cell signaling (HMDB: HMDB0031386)

Biochemical process

Lipid transport (HMDB: HMDB0031386)

Role

Biological role

Energy source (HMDB: HMDB0031386)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031386)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	131 °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	0.19 g/L	ALOGPS
logP	2.95	ALOGPS
logP	2.76	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	68.86 m³·mol⁻¹	ChemAxon
Polarizability	26.9 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]+	156.235	31661259
DarkChem	[M-H]-	151.855	31661259
DeepCCS	[M+H]+	158.768	30932474
DeepCCS	[M-H]-	156.41	30932474
DeepCCS	[M-2H]-	189.296	30932474
DeepCCS	[M+Na]+	164.861	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.	5.72 minutes	32390414
Predicted by Siyang on May 30, 2022	14.8163 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.12 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2634.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	406.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	200.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	100.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	637.0 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	700.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1229.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	398.8 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	1297.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	480.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	372.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	417.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	478.4 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	18.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide	C\C1=C\CCC2(C)OC2CC2C(C1)OC(=O)C2=C	2674.6	Standard polar	33892256
(1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide	C\C1=C\CCC2(C)OC2CC2C(C1)OC(=O)C2=C	1892.6	Standard non polar	33892256
(1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide	C\C1=C\CCC2(C)OC2CC2C(C1)OC(=O)C2=C	2144.2	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 - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-6970000000-62d6931d2d28fc7040b6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),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 - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 10V, Positive-QTOF	splash10-0002-0290000000-bad7eaaa81c9e2d2013b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 20V, Positive-QTOF	splash10-003s-2690000000-fc7c38c665d848c0b73a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 40V, Positive-QTOF	splash10-0159-9200000000-9d234ff0004ade870c11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 10V, Negative-QTOF	splash10-0002-0090000000-ee5e94f984a2f447120e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 20V, Negative-QTOF	splash10-0f6t-0090000000-b91cc2af66df8f1ca24c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 40V, Negative-QTOF	splash10-0gba-9310000000-45836c274a33da3d7dca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 10V, Positive-QTOF	splash10-0002-0090000000-b480e033d103202da8fc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 20V, Positive-QTOF	splash10-0f8a-0190000000-90c6692119c8cd915b55	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 40V, Positive-QTOF	splash10-0ugi-0590000000-3fd8b4edde7af6618752	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 10V, Negative-QTOF	splash10-0002-0090000000-3ef26a39d49de07a33cd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 20V, Negative-QTOF	splash10-002b-0090000000-d31953b18076f9907626	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide 40V, Negative-QTOF	splash10-004i-2690000000-c0f880b5a5e07c18c0d3	2021-09-24	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

FDB003453

KNApSAcK ID

Not Available

Chemspider ID

35013358

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13817976

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
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Showing metabocard for (1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide (HMDB0031386)

MOL for HMDB0031386 ((1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide)

3D MOL for HMDB0031386 ((1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide)

3D SDF for HMDB0031386 ((1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide)

3D-SDF for HMDB0031386 ((1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide)

PDB for HMDB0031386 ((1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide)

3D PDB for HMDB0031386 ((1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide)

SMILES for HMDB0031386 ((1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide)

INCHI for HMDB0031386 ((1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide)

Structure for HMDB0031386 ((1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),11(13)-germacradien-12,8-olide)

3D Structure for HMDB0031386 ((1(10)E,4beta,5alpha,8beta)-4,5-Epoxy-1(10),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