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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:59 UTC

Update Date

2022-03-07 02:53:25 UTC

HMDB ID

HMDB0032649

Secondary Accession Numbers

HMDB32649

Metabolite Identification

Common Name

4,5-Epoxy-11(13)-guaien-12,8-olide

Description

4,5-Epoxy-11(13)-guaien-12,8-olide belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 4,5-Epoxy-11(13)-guaien-12,8-olide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0032649
     RDKit          3D
4,5-Epoxy-11(13)-guaien-12,8-olide
 38 41  0  0  0  0  0  0  0  0999 V2000
    2.6741   -2.8273    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639   -1.6328   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176   -0.8134   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307   -1.1727   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3385    0.4268   -0.9579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1005    0.5929   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690    1.5492   -0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0816    1.8771    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2485    3.3350   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030    1.0407   -0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066    1.1570    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1141    0.0136    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880   -1.0860   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718   -2.4320    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -1.0958   -1.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900   -0.4167   -0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -0.9575    0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5001   -0.8104   -0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6265   -3.2818    0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764   -3.3634    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328    0.7826    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7291    1.0291   -1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614    2.4560   -1.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252    1.6872    1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0556    3.6022    0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169    3.6669   -1.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599    3.9095    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    1.4385   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090    2.1219    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8016    0.8731    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6940    0.4371   -0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724   -0.3040    1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604   -2.6269    0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6564   -2.5147    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9736   -3.2656   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437   -0.4158    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -2.0374    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.9422   -1.5813 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
 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 10  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
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END


  Mrv0541 05061306372D          

 18 21  0  0  0  0            999 V2000
    1.1859    2.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4818   -1.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0300   -0.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2078    1.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    0.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3689    1.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564   -0.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5439    1.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4079   -0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997    0.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0295    0.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8832    0.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292    0.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5048   -0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131    0.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8335    0.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7049    1.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2254   -0.6882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  6  1  0  0  0  0
  9  2  2  0  0  0  0
 10  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  4  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14  5  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  2  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032649

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC2OC(=O)C(=C)C2CC23OC2(C)CCC13

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-6-12-10(9(2)13(16)17-12)7-15-11(8)4-5-14(15,3)18-15/h8,10-12H,2,4-7H2,1,3H3

> <INCHI_KEY>
AIHKZOVNPAYCEL-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.39558480544267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,13-dimethyl-4-methylidene-6,14-dioxatetracyclo[8.4.0.0¹,¹³.0³,⁷]tetradecan-5-one

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.5356971516666666

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.249433459843176

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
66.0395

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,13-dimethyl-4-methylidene-6,14-dioxatetracyclo[8.4.0.0¹,¹³.0³,⁷]tetradecan-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032649
     RDKit          3D
4,5-Epoxy-11(13)-guaien-12,8-olide
 38 41  0  0  0  0  0  0  0  0999 V2000
    2.6741   -2.8273    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639   -1.6328   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176   -0.8134   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307   -1.1727   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3385    0.4268   -0.9579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1005    0.5929   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690    1.5492   -0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0816    1.8771    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2485    3.3350   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030    1.0407   -0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066    1.1570    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1141    0.0136    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880   -1.0860   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718   -2.4320    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -1.0958   -1.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900   -0.4167   -0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -0.9575    0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5001   -0.8104   -0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6265   -3.2818    0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764   -3.3634    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328    0.7826    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7291    1.0291   -1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614    2.4560   -1.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252    1.6872    1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0556    3.6022    0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169    3.6669   -1.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599    3.9095    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    1.4385   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090    2.1219    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8016    0.8731    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6940    0.4371   -0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724   -0.3040    1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604   -2.6269    0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6564   -2.5147    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9736   -3.2656   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437   -0.4158    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -2.0374    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.9422   -1.5813 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
 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 10  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
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 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       2.214   4.348   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.499  -2.068   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.056  -1.794   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.388   1.894   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.217   0.478   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.422   2.961   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.652  -0.413   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.882   2.961   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.361  -0.535   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.039   0.255   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.922   1.757   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.382   1.757   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.521   0.478   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.942  -0.535   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.264   0.255   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.023   0.136   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.916   1.894   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.287  -1.285   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4    5   11                                                       
CONECT    5    4   14                                                       
CONECT    6    8   12                                                       
CONECT    7   10   15                                                       
CONECT    8    1    6   11                                                  
CONECT    9    2   10   13                                                  
CONECT   10    7    9   12                                                  
CONECT   11    4    8   15                                                  
CONECT   12    6   10   17                                                  
CONECT   13    9   16   17                                                  
CONECT   14    3    5   15   18                                             
CONECT   15    7   11   14   18                                             
CONECT   16   13                                                            
CONECT   17   12   13                                                       
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

COMPND    HMDB0032649
HETATM    1  C1  UNL     1       2.674  -2.827   0.423  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.664  -1.633  -0.123  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.818  -0.813  -0.476  1.00  0.00           C  
HETATM    4  O1  UNL     1       5.031  -1.173  -0.362  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.338   0.427  -0.958  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.100   0.593  -0.342  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.169   1.549  -0.992  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.082   1.877   0.014  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.248   3.335  -0.085  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.103   1.041  -0.291  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.207   1.157   0.749  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.114   0.014   0.278  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.188  -1.086  -0.120  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.272  -2.432   0.558  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.565  -1.096  -1.344  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.890  -0.417  -0.353  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.301  -0.957   0.330  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.500  -0.810  -0.519  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.627  -3.282   0.648  1.00  0.00           H  
HETATM   20  H2  UNL     1       1.776  -3.363   0.652  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.233   0.783   0.746  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.729   1.029  -1.893  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.661   2.456  -1.396  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.425   1.687   1.057  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.056   3.602   0.595  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.417   3.667  -1.138  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.660   3.909   0.249  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.560   1.438  -1.244  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.709   2.122   0.732  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.802   0.873   1.736  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.694   0.437  -0.579  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.772  -0.304   1.103  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.360  -2.627   0.762  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.656  -2.515   1.455  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.974  -3.266  -0.140  1.00  0.00           H  
HETATM   36  H18 UNL     1       0.444  -0.416   1.298  1.00  0.00           H  
HETATM   37  H19 UNL     1       0.128  -2.037   0.552  1.00  0.00           H  
HETATM   38  H20 UNL     1       1.227  -0.942  -1.581  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   24
CONECT    9   25   26   27
CONECT   10   11   16   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   15   16
CONECT   14   33   34   35
CONECT   15   16
CONECT   16   17
CONECT   17   18   36   37
CONECT   18   38
END

HMDB0032649
     RDKit          3D
4,5-Epoxy-11(13)-guaien-12,8-olide
 38 41  0  0  0  0  0  0  0  0999 V2000
    2.6741   -2.8273    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639   -1.6328   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176   -0.8134   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307   -1.1727   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3385    0.4268   -0.9579 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1005    0.5929   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690    1.5492   -0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0816    1.8771    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2485    3.3350   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030    1.0407   -0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066    1.1570    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1141    0.0136    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880   -1.0860   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718   -2.4320    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -1.0958   -1.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900   -0.4167   -0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -0.9575    0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5001   -0.8104   -0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6265   -3.2818    0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764   -3.3634    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328    0.7826    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7291    1.0291   -1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614    2.4560   -1.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252    1.6872    1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0556    3.6022    0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169    3.6669   -1.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599    3.9095    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    1.4385   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090    2.1219    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8016    0.8731    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6940    0.4371   -0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724   -0.3040    1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604   -2.6269    0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6564   -2.5147    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9736   -3.2656   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437   -0.4158    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -2.0374    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.9422   -1.5813 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
 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 10  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
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 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
4alpha,5alpha-Epoxy-10alpha,14H-inuviscolide	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

9,13-dimethyl-4-methylidene-6,14-dioxatetracyclo[8.4.0.0¹,¹³.0³,⁷]tetradecan-5-one

Traditional Name

9,13-dimethyl-4-methylidene-6,14-dioxatetracyclo[8.4.0.0¹,¹³.0³,⁷]tetradecan-5-one

CAS Registry Number

68776-54-5

SMILES

CC1CC2OC(=O)C(=C)C2CC23OC2(C)CCC13

InChI Identifier

InChI=1S/C15H20O3/c1-8-6-12-10(9(2)13(16)17-12)7-15-11(8)4-5-14(15,3)18-15/h8,10-12H,2,4-7H2,1,3H3

InChI Key

AIHKZOVNPAYCEL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0032649)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032649)

Source

Endogenous

Endogenous (HMDB: HMDB0032649)

Plant

Plant (HMDB: HMDB0032649)

Animal

Animal (HMDB: HMDB0032649)

Exogenous

Food

Food (HMDB: HMDB0032649)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0032649)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0032649)

Cellular process

Cell signaling (HMDB: HMDB0032649)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0032649)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0032649)

Nutrient

Nutrient (HMDB: HMDB0032649)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032649)

Emulsifier (HMDB: HMDB0032649)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.54	ChemAxon
logS	-3.4	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	66.04 m³·mol⁻¹	ChemAxon
Polarizability	27.4 Å³	ChemAxon
Number of Rings	4	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]+	155.854	31661259
DarkChem	[M-H]-	153.457	31661259
DeepCCS	[M-2H]-	190.538	30932474
DeepCCS	[M+Na]+	165.792	30932474
AllCCS	[M+H]+	158.2	32859911
AllCCS	[M+H-H2O]+	154.5	32859911
AllCCS	[M+NH4]+	161.6	32859911
AllCCS	[M+Na]+	162.5	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	164.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,5-Epoxy-11(13)-guaien-12,8-olide	CC1CC2OC(=O)C(=C)C2CC23OC2(C)CCC13	2680.9	Standard polar	33892256
4,5-Epoxy-11(13)-guaien-12,8-olide	CC1CC2OC(=O)C(=C)C2CC23OC2(C)CCC13	1883.1	Standard non polar	33892256
4,5-Epoxy-11(13)-guaien-12,8-olide	CC1CC2OC(=O)C(=C)C2CC23OC2(C)CCC13	2127.1	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 - 4,5-Epoxy-11(13)-guaien-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ugr-6930000000-22ac545b8ac3ea999d6a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Epoxy-11(13)-guaien-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 - 4,5-Epoxy-11(13)-guaien-12,8-olide 10V, Positive-QTOF	splash10-0002-0290000000-d230874a5a340ed06b86	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 20V, Positive-QTOF	splash10-0032-0790000000-4b9d787ec83ca5a0d5f5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 40V, Positive-QTOF	splash10-0zfu-9200000000-0acb774635bbf10eb77a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 10V, Negative-QTOF	splash10-0002-0090000000-4e9f2f82e50715dadc30	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 20V, Negative-QTOF	splash10-0f6t-0090000000-600e903ffd01d7aff85d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 40V, Negative-QTOF	splash10-0uxr-9410000000-7976bdc228269a3ed374	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 10V, Positive-QTOF	splash10-0002-0090000000-bf3c91f3d743135e201a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 20V, Positive-QTOF	splash10-0002-0290000000-8beea45082fa7ef13938	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 40V, Positive-QTOF	splash10-0002-3890000000-33ec4bc269887fda66ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 20V, Negative-QTOF	splash10-0002-0090000000-61b17a23641394f122ab	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Epoxy-11(13)-guaien-12,8-olide 40V, Negative-QTOF	splash10-00r5-8980000000-0e0ff8c9bdb1f77cb99d	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB010598

KNApSAcK ID

C00021708

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14313753

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 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 4,5-Epoxy-11(13)-guaien-12,8-olide (HMDB0032649)

MOL for HMDB0032649 (4,5-Epoxy-11(13)-guaien-12,8-olide)

3D MOL for HMDB0032649 (4,5-Epoxy-11(13)-guaien-12,8-olide)

3D SDF for HMDB0032649 (4,5-Epoxy-11(13)-guaien-12,8-olide)

3D-SDF for HMDB0032649 (4,5-Epoxy-11(13)-guaien-12,8-olide)

PDB for HMDB0032649 (4,5-Epoxy-11(13)-guaien-12,8-olide)

3D PDB for HMDB0032649 (4,5-Epoxy-11(13)-guaien-12,8-olide)

SMILES for HMDB0032649 (4,5-Epoxy-11(13)-guaien-12,8-olide)

INCHI for HMDB0032649 (4,5-Epoxy-11(13)-guaien-12,8-olide)

Structure for HMDB0032649 (4,5-Epoxy-11(13)-guaien-12,8-olide)

3D Structure for HMDB0032649 (4,5-Epoxy-11(13)-guaien-12,8-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra