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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:49:45 UTC

Update Date

2022-03-07 02:55:00 UTC

HMDB ID

HMDB0036664

Secondary Accession Numbers

HMDB36664

Metabolite Identification

Common Name

Ketopelenolide a

Description

Ketopelenolide a belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a small amount of articles have been published on Ketopelenolide a.

Structure

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

HMDB0036664
     RDKit          3D
Ketopelenolide a
 40 41  0  0  0  0  0  0  0  0999 V2000
   -2.9966   -2.3142    1.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131   -1.2190    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8849   -0.4533   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.6382   -1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308    1.7448   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523    2.0905    0.7466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747    2.4810   -0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990    2.9296    0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6049    1.7618   -1.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.7377   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    1.0269   -0.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3847   -0.0217   -0.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4371    0.0532   -1.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5611   -1.2256   -0.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890   -1.6289    0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1573   -0.6072   -0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1267   -1.4970   -0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7599   -1.0278    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3193   -1.8783    2.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8643   -2.6188    0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3519   -3.1924    1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9619   -0.6548   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    1.1025   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4536    0.2134   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7087    3.4109   -0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3207    2.3133    1.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746    4.0087    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2082    2.9212    0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3108    2.5636   -1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    1.2609   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652    0.8849    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034   -2.0269   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0134   -1.7071    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6215   -0.9643    1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -2.6655    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0118   -0.5012   -1.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5403   -1.9016   -1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6329   -2.4508    0.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411    0.0195    1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -1.6062    1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END


  Mrv0541 05061309162D          

 18 19  0  0  0  0            999 V2000
    5.6722    1.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -0.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    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  1  0  0  0  0
  9  5  2  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 16 13  2  0  0  0  0
 17 15  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036664

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CC\C(C)=C/CC(=O)C(C)CC2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,10-12,14H,4,6-8H2,1-3H3/b9-5-

> <INCHI_KEY>
KLZWSNKEPLKAOS-UITAMQMPSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.93645357564451

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,10-trimethyl-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-2,9-dione

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.0009334203333324

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.151926490452496

> <JCHEM_PKA_STRONGEST_BASIC>
-6.937407616792015

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
70.1143

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,10-trimethyl-3H,3aH,4H,5H,8H,10H,11H,11aH-cyclodeca[b]furan-2,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036664
     RDKit          3D
Ketopelenolide a
 40 41  0  0  0  0  0  0  0  0999 V2000
   -2.9966   -2.3142    1.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131   -1.2190    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8849   -0.4533   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.6382   -1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308    1.7448   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523    2.0905    0.7466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747    2.4810   -0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990    2.9296    0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6049    1.7618   -1.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.7377   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    1.0269   -0.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3847   -0.0217   -0.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4371    0.0532   -1.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5611   -1.2256   -0.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890   -1.6289    0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1573   -0.6072   -0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1267   -1.4970   -0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7599   -1.0278    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3193   -1.8783    2.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8643   -2.6188    0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3519   -3.1924    1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9619   -0.6548   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    1.1025   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4536    0.2134   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7087    3.4109   -0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3207    2.3133    1.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746    4.0087    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2082    2.9212    0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3108    2.5636   -1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    1.2609   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652    0.8849    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034   -2.0269   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0134   -1.7071    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6215   -0.9643    1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -2.6655    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0118   -0.5012   -1.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5403   -1.9016   -1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6329   -2.4508    0.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411    0.0195    1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -1.6062    1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  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      10.588   2.424   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.389  -4.531   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.331   1.544   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.259   0.006   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.918  -2.397   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.467  -1.508   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.379  -2.325   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   12                                                       
CONECT    7    5   13                                                       
CONECT    8   10   14                                                       
CONECT    9    1    4    5                                                  
CONECT   10    2    8   13                                                  
CONECT   11    3   12   15                                                  
CONECT   12    6   11   14                                                  
CONECT   13    7   10   16                                                  
CONECT   14    8   12   18                                                  
CONECT   15   11   17   18                                                  
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0036664
HETATM    1  C1  UNL     1      -2.997  -2.314   1.245  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.213  -1.219   0.554  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.885  -0.453  -0.299  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.213   0.638  -1.021  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.731   1.745  -0.186  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.452   2.091   0.747  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.475   2.481  -0.352  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.099   2.930   0.988  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.605   1.762  -1.082  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.342   0.738  -0.221  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.745   1.027  -0.382  1.00  0.00           O  
HETATM   12  C10 UNL     1       3.385  -0.022  -0.991  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.437   0.053  -1.674  1.00  0.00           O  
HETATM   14  C11 UNL     1       2.561  -1.226  -0.659  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.889  -1.629   0.737  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.157  -0.607  -0.768  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.127  -1.497  -0.244  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.760  -1.028   0.835  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.319  -1.878   2.214  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.864  -2.619   0.637  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.352  -3.192   1.433  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.962  -0.655  -0.455  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.965   1.103  -1.730  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.454   0.213  -1.704  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.709   3.411  -0.931  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.321   2.313   1.786  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.175   4.009   1.176  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.208   2.921   0.965  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.311   2.564  -1.457  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.261   1.261  -2.020  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.165   0.885   0.853  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.703  -2.027  -1.410  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.013  -1.707   1.411  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.622  -0.964   1.211  1.00  0.00           H  
HETATM   35  H17 UNL     1       3.319  -2.665   0.692  1.00  0.00           H  
HETATM   36  H18 UNL     1       1.012  -0.501  -1.887  1.00  0.00           H  
HETATM   37  H19 UNL     1      -0.540  -1.902  -1.068  1.00  0.00           H  
HETATM   38  H20 UNL     1       0.633  -2.451   0.106  1.00  0.00           H  
HETATM   39  H21 UNL     1      -0.641   0.020   1.158  1.00  0.00           H  
HETATM   40  H22 UNL     1      -0.567  -1.606   1.792  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4   22
CONECT    4    5   23   24
CONECT    5    6    6    7
CONECT    7    8    9   25
CONECT    8   26   27   28
CONECT    9   10   29   30
CONECT   10   11   16   31
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   16   32
CONECT   15   33   34   35
CONECT   16   17   36
CONECT   17   18   37   38
CONECT   18   39   40
END

HMDB0036664
     RDKit          3D
Ketopelenolide a
 40 41  0  0  0  0  0  0  0  0999 V2000
   -2.9966   -2.3142    1.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131   -1.2190    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8849   -0.4533   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.6382   -1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308    1.7448   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523    2.0905    0.7466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747    2.4810   -0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990    2.9296    0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6049    1.7618   -1.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.7377   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    1.0269   -0.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3847   -0.0217   -0.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4371    0.0532   -1.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5611   -1.2256   -0.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890   -1.6289    0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1573   -0.6072   -0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1267   -1.4970   -0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7599   -1.0278    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3193   -1.8783    2.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8643   -2.6188    0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3519   -3.1924    1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9619   -0.6548   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    1.1025   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4536    0.2134   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7087    3.4109   -0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3207    2.3133    1.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746    4.0087    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2082    2.9212    0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3108    2.5636   -1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    1.2609   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652    0.8849    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034   -2.0269   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0134   -1.7071    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6215   -0.9643    1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -2.6655    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0118   -0.5012   -1.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5403   -1.9016   -1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6329   -2.4508    0.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411    0.0195    1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -1.6062    1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-oxo-1(10)-Germacren-12,6-olide	HMDB
Ketopelenolid-a	HMDB
Oxopelenolide a	HMDB

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.3334

Monoisotopic Molecular Weight

250.15689457

IUPAC Name

3,6,10-trimethyl-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-2,9-dione

Traditional Name

3,6,10-trimethyl-3H,3aH,4H,5H,8H,10H,11H,11aH-cyclodeca[b]furan-2,9-dione

CAS Registry Number

17909-92-1

SMILES

CC1C2CC\C(C)=C/CC(=O)C(C)CC2OC1=O

InChI Identifier

InChI=1S/C15H22O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,10-12,14H,4,6-8H2,1-3H3/b9-5-

InChI Key

KLZWSNKEPLKAOS-UITAMQMPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036664)
Cell membrane (HMDB: HMDB0036664)

Cellular substructure

Extracellular (HMDB: HMDB0036664)
Membrane (HMDB: HMDB0036664)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036664)

Source

Endogenous

Endogenous (HMDB: HMDB0036664)

Plant

Plant (HMDB: HMDB0036664)

Animal

Animal (HMDB: HMDB0036664)

Exogenous

Food

Food (HMDB: HMDB0036664)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036664)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036664)

Cellular process

Cell signaling (HMDB: HMDB0036664)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036664)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036664)

Nutrient

Nutrient (HMDB: HMDB0036664)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036664)

Emulsifier (HMDB: HMDB0036664)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	114 °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	0.27 g/L	ALOGPS
logP	2.69	ALOGPS
logP	3	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	16.15	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.11 m³·mol⁻¹	ChemAxon
Polarizability	27.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	159.463	31661259
DarkChem	[M-H]-	152.969	31661259
DeepCCS	[M+H]+	160.428	30932474
DeepCCS	[M-H]-	158.07	30932474
DeepCCS	[M-2H]-	191.33	30932474
DeepCCS	[M+Na]+	166.521	30932474
AllCCS	[M+H]+	159.2	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	162.7	32859911
AllCCS	[M+Na]+	163.7	32859911
AllCCS	[M-H]-	164.9	32859911
AllCCS	[M+Na-2H]-	165.1	32859911
AllCCS	[M+HCOO]-	165.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ketopelenolide a	CC1C2CC\C(C)=C/CC(=O)C(C)CC2OC1=O	2767.7	Standard polar	33892256
Ketopelenolide a	CC1C2CC\C(C)=C/CC(=O)C(C)CC2OC1=O	2014.8	Standard non polar	33892256
Ketopelenolide a	CC1C2CC\C(C)=C/CC(=O)C(C)CC2OC1=O	2089.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ketopelenolide a,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C/C=C(/C)CCC2C(C1)OC(=O)C2C	2144.9	Semi standard non polar	33892256
Ketopelenolide a,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C/C=C(/C)CCC2C(C1)OC(=O)C2C	2026.0	Standard non polar	33892256
Ketopelenolide a,1TMS,isomer #2	C/C1=C/C=C(O[Si](C)(C)C)C(C)CC2OC(=O)C(C)C2CC1	2217.7	Semi standard non polar	33892256
Ketopelenolide a,1TMS,isomer #2	C/C1=C/C=C(O[Si](C)(C)C)C(C)CC2OC(=O)C(C)C2CC1	1982.4	Standard non polar	33892256
Ketopelenolide a,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C/C=C(/C)CCC2C(C1)OC(=O)C2C	2368.2	Semi standard non polar	33892256
Ketopelenolide a,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C/C=C(/C)CCC2C(C1)OC(=O)C2C	2253.4	Standard non polar	33892256
Ketopelenolide a,1TBDMS,isomer #2	C/C1=C/C=C(O[Si](C)(C)C(C)(C)C)C(C)CC2OC(=O)C(C)C2CC1	2440.8	Semi standard non polar	33892256
Ketopelenolide a,1TBDMS,isomer #2	C/C1=C/C=C(O[Si](C)(C)C(C)(C)C)C(C)CC2OC(=O)C(C)C2CC1	2147.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ketopelenolide a GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-7940000000-bbda2c5a6b8c6e8c9c77	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketopelenolide a 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 - Ketopelenolide a 10V, Positive-QTOF	splash10-0udi-0290000000-a0a03e0506e0ea85dd31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 20V, Positive-QTOF	splash10-0udi-3890000000-5fe492b4d6aabb5dd633	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 40V, Positive-QTOF	splash10-1000-9500000000-6f037a2dac50170a67fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 10V, Negative-QTOF	splash10-0002-0090000000-e34b4fe85e6fd851bbca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 20V, Negative-QTOF	splash10-052b-0190000000-cff3accc943516cb1e1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 40V, Negative-QTOF	splash10-0006-9210000000-28463701c7a16359d049	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 10V, Negative-QTOF	splash10-0002-0090000000-0dd1e5565d33dd37f20a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 20V, Negative-QTOF	splash10-056s-0590000000-9378de90e875d461e723	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 40V, Negative-QTOF	splash10-00pi-2790000000-b01858e15d19eb379baf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 10V, Positive-QTOF	splash10-0udi-0090000000-a2e6b66e384510551893	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 20V, Positive-QTOF	splash10-0kei-0690000000-cc5a8f2f186f000c8a54	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketopelenolide a 40V, Positive-QTOF	splash10-056r-0910000000-08bcb1635047109c1dfc	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

FDB015591

KNApSAcK ID

C00012210

Chemspider ID

35014186

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12304831

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 Ketopelenolide a (HMDB0036664)

MOL for HMDB0036664 (Ketopelenolide a)

3D MOL for HMDB0036664 (Ketopelenolide a)

3D SDF for HMDB0036664 (Ketopelenolide a)

3D-SDF for HMDB0036664 (Ketopelenolide a)

PDB for HMDB0036664 (Ketopelenolide a)

3D PDB for HMDB0036664 (Ketopelenolide a)

SMILES for HMDB0036664 (Ketopelenolide a)

INCHI for HMDB0036664 (Ketopelenolide a)

Structure for HMDB0036664 (Ketopelenolide a)

3D Structure for HMDB0036664 (Ketopelenolide a)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra