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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:43 UTC

Update Date

2022-03-07 02:52:56 UTC

HMDB ID

HMDB0031374

Secondary Accession Numbers

HMDB31374

Metabolite Identification

Common Name

(1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide

Description

(1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 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 (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide.

Structure

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

HMDB0031374
     RDKit          3D
(1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-o...
 52 53  0  0  0  0  0  0  0  0999 V2000
   -0.2000   -1.8413   -2.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8809   -1.9679   -2.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6963   -3.1320   -1.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2937   -4.3195   -2.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253   -2.7453   -1.4472 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9532   -1.3257   -1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930   -1.1269    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -0.1540    0.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7734   -0.4087    2.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2578    1.2022    0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9986    1.7831   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5890    2.1730   -0.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4637    1.6157   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7866    2.3511   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709    0.3847    0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109    0.0373    0.1079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    0.0024    1.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8772    0.2930    2.2855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6853   -0.3529    0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474   -0.2932    2.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401    0.6716   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7707    0.2707   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9070   -0.8261    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5396   -0.9059   -1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
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 24 52  1  0
M  END


  Mrv0541 02241209462D          

 24 25  0  0  0  0            999 V2000
   -2.1353   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353   -0.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -1.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7080   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211    0.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4211    1.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0062    2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7219    2.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 19 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031374

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)C(=O)OC1CC2C(OC(=O)C2=C)\C=C(C)\CC\C=C1/C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-6-13(3)19(21)23-17-11-16-15(5)20(22)24-18(16)10-12(2)8-7-9-14(17)4/h9-10,13,16-18H,5-8,11H2,1-4H3/b12-10+,14-9+

> <INCHI_KEY>
HNBSPEQFYAYDLE-LSBMZBKTSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.4339

> <EXACT_MASS>
332.198759384

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.92095294650849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-methylbutanoate

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
4.714571780333334

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.6677344221184836

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
94.41579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031374
     RDKit          3D
(1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-o...
 52 53  0  0  0  0  0  0  0  0999 V2000
   -0.2000   -1.8413   -2.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8809   -1.9679   -2.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6963   -3.1320   -1.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2937   -4.3195   -2.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
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 23 51  1  0
 24 52  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.986  -0.040   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.986  -1.581   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.653  -2.352   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.322  -1.581   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.322  -0.040   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.653   0.728   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.012  -2.352   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.342  -1.581   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.342  -0.040   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.012   0.728   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.330  -3.855   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.856  -4.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.478  -2.617   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.551  -1.376   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.012   2.270   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.653  -3.893   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.627  -5.353   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.986  -2.301   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.322   3.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.322   4.582   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.653   2.270   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.653   5.353   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.012   5.353   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.348   4.582   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    7                                                       
CONECT    5    6   10   14                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    5    9   15                                                  
CONECT   11    7   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13    8   12   18                                                  
CONECT   14    5                                                            
CONECT   15   10   19                                                       
CONECT   16    3                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   15   20   21                                                  
CONECT   20   19   22   23                                                  
CONECT   21   19                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0031374
HETATM    1  C1  UNL     1      -0.200  -1.841  -2.816  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.881  -1.968  -2.067  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.696  -3.132  -1.877  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.294  -4.320  -2.088  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.925  -2.745  -1.447  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.953  -1.326  -1.118  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.693  -1.127   0.112  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.842  -0.154   0.966  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.773  -0.409   2.186  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.258   1.202   0.995  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.999   1.783  -0.327  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.589   2.173  -0.616  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.464   1.616  -0.337  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.787   2.351  -0.820  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.071   0.385   0.359  1.00  0.00           C  
HETATM   16  O3  UNL     1      -1.311   0.037   0.108  1.00  0.00           O  
HETATM   17  C14 UNL     1      -2.265   0.002   1.110  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.877   0.293   2.286  1.00  0.00           O  
HETATM   19  C15 UNL     1      -3.685  -0.353   0.861  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.447  -0.293   2.162  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.340   0.672  -0.072  1.00  0.00           C  
HETATM   22  C18 UNL     1      -5.771   0.271  -0.292  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.907  -0.826   0.125  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.540  -0.906  -1.209  1.00  0.00           C  
HETATM   25  H1  UNL     1      -0.584  -2.646  -3.381  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.700  -0.886  -2.848  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.468  -0.933  -2.040  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.302  -2.048   0.407  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.739   0.100   2.003  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.942  -1.477   2.301  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.327   0.010   3.083  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.904   1.891   1.621  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.298   1.235   1.595  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.650   2.736  -0.375  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.424   1.222  -1.204  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.577   3.146  -1.194  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.389   2.539   0.111  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.565   3.310  -1.254  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.373   1.690  -1.495  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.082   0.578   1.454  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.757  -1.326   0.371  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.838  -0.629   3.022  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.786   0.743   2.399  1.00  0.00           H  
HETATM   44  H20 UNL     1      -5.377  -0.917   2.052  1.00  0.00           H  
HETATM   45  H21 UNL     1      -4.341   1.676   0.411  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.767   0.745  -1.006  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.948  -0.807  -0.241  1.00  0.00           H  
HETATM   48  H24 UNL     1      -6.128   0.632  -1.300  1.00  0.00           H  
HETATM   49  H25 UNL     1      -6.466   0.759   0.442  1.00  0.00           H  
HETATM   50  H26 UNL     1       1.555  -1.042   0.996  1.00  0.00           H  
HETATM   51  H27 UNL     1       0.172  -1.696   0.176  1.00  0.00           H  
HETATM   52  H28 UNL     1       1.377   0.009  -1.839  1.00  0.00           H  
CONECT    1    2    2   25   26
CONECT    2    3   24
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   24   27
CONECT    7    8    8   28
CONECT    8    9   10
CONECT    9   29   30   31
CONECT   10   11   32   33
CONECT   11   12   34   35
CONECT   12   13   13   36
CONECT   13   14   15
CONECT   14   37   38   39
CONECT   15   16   23   40
CONECT   16   17
CONECT   17   18   18   19
CONECT   19   20   21   41
CONECT   20   42   43   44
CONECT   21   22   45   46
CONECT   22   47   48   49
CONECT   23   24   50   51
CONECT   24   52
END

HMDB0031374
     RDKit          3D
(1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-o...
 52 53  0  0  0  0  0  0  0  0999 V2000
   -0.2000   -1.8413   -2.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8809   -1.9679   -2.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6963   -3.1320   -1.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2937   -4.3195   -2.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253   -2.7453   -1.4472 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9532   -1.3257   -1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930   -1.1269    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -0.1540    0.9661 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7734   -0.4087    2.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2578    1.2022    0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9986    1.7831   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5890    2.1730   -0.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4637    1.6157   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7866    2.3511   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709    0.3847    0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109    0.0373    0.1079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    0.0024    1.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8772    0.2930    2.2855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6853   -0.3529    0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474   -0.2932    2.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401    0.6716   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7707    0.2707   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9070   -0.8261    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5396   -0.9059   -1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5842   -2.6463   -3.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -0.8862   -2.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4680   -0.9333   -2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3017   -2.0480    0.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7395    0.0999    2.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420   -1.4766    2.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3274    0.0099    3.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9045    1.8911    1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2975    1.2347    1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6503    2.7362   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4241    1.2225   -1.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5766    3.1458   -1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887    2.5394    0.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5654    3.3101   -1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3733    1.6897   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822    0.5784    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7570   -1.3261    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381   -0.6289    3.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7860    0.7433    2.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3765   -0.9171    2.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3410    1.6764    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7671    0.7452   -1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9480   -0.8074   -0.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1280    0.6319   -1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4663    0.7588    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554   -1.0418    0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725   -1.6961    0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773    0.0088   -1.8395 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 15 23  1  0
 23 24  1  0
 24  2  1  0
 24  6  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,10-Dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-5-yl 2-methylbutanoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₄

Average Molecular Weight

332.4339

Monoisotopic Molecular Weight

332.198759384

IUPAC Name

6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-methylbutanoate

Traditional Name

6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1CC2C(OC(=O)C2=C)\C=C(C)\CC\C=C1/C

InChI Identifier

InChI=1S/C20H28O4/c1-6-13(3)19(21)23-17-11-16-15(5)20(22)24-18(16)10-12(2)8-7-9-14(17)4/h9-10,13,16-18H,5-8,11H2,1-4H3/b12-10+,14-9+

InChI Key

HNBSPEQFYAYDLE-LSBMZBKTSA-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
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen 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: HMDB0031374)

Source

Endogenous

Endogenous (HMDB: HMDB0031374)

Plant

Plant (HMDB: HMDB0031374)

Animal

Animal (HMDB: HMDB0031374)

Exogenous

Food

Food (HMDB: HMDB0031374)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0031374)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031374)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031374)

Lipid metabolism pathway (HMDB: HMDB0031374)

Cellular process

Cell signaling (HMDB: HMDB0031374)

Biochemical process

Lipid transport (HMDB: HMDB0031374)

Role

Biological role

Energy source (HMDB: HMDB0031374)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031374)

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	0.013 g/L	ALOGPS
logP	4.54	ALOGPS
logP	4.71	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.42 m³·mol⁻¹	ChemAxon
Polarizability	36.92 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]+	180.41	31661259
DarkChem	[M-H]-	179.009	31661259
DeepCCS	[M+H]+	185.587	30932474
DeepCCS	[M-H]-	183.229	30932474
DeepCCS	[M-2H]-	217.154	30932474
DeepCCS	[M+Na]+	192.381	30932474
AllCCS	[M+H]+	184.0	32859911
AllCCS	[M+H-H2O]+	181.0	32859911
AllCCS	[M+NH4]+	186.7	32859911
AllCCS	[M+Na]+	187.5	32859911
AllCCS	[M-H]-	185.9	32859911
AllCCS	[M+Na-2H]-	186.3	32859911
AllCCS	[M+HCOO]-	187.0	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.	8.93 minutes	32390414
Predicted by Siyang on May 30, 2022	19.0289 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.68 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3262.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	465.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	221.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	216.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	113.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	705.8 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	873.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1619.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	648.8 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	1536.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	493.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	467.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	320.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	451.0 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide	CCC(C)C(=O)OC1CC2C(OC(=O)C2=C)\C=C(C)\CC\C=C1/C	3109.8	Standard polar	33892256
(1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide	CCC(C)C(=O)OC1CC2C(OC(=O)C2=C)\C=C(C)\CC\C=C1/C	2348.5	Standard non polar	33892256
(1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide	CCC(C)C(=O)OC1CC2C(OC(=O)C2=C)\C=C(C)\CC\C=C1/C	2405.7	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,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5i-9350000000-a191eae139b5af9cc69c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-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,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 10V, Positive-QTOF	splash10-001i-4079000000-00ab522d513863d61539	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 20V, Positive-QTOF	splash10-053i-9352000000-2c3dd9f4f63409a14db3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 40V, Positive-QTOF	splash10-0a4i-9300000000-d458e1759f728159994e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 10V, Negative-QTOF	splash10-001i-0049000000-c186be84476cb3eba93c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 20V, Negative-QTOF	splash10-0f8i-4397000000-ce452a019d80e4c789c6	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 40V, Negative-QTOF	splash10-0zfr-8950000000-134105f3c04d8013e811	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 10V, Positive-QTOF	splash10-001i-0090000000-0c877456b34e6881f19c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 20V, Positive-QTOF	splash10-001r-0290000000-009a472d19ccb01c8af2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 40V, Positive-QTOF	splash10-0019-4891000000-7b45d8f591260d5c9692	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 10V, Negative-QTOF	splash10-001i-0069000000-5fb8bef97e7a610d5cad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 20V, Negative-QTOF	splash10-0059-4291000000-9d6d6050fdaf2639af32	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 40V, Negative-QTOF	splash10-0pb9-9120000000-2824f20d487ad597b0a4	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

FDB003441

KNApSAcK ID

Not Available

Chemspider ID

35013353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751161

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 (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide (HMDB0031374)

MOL for HMDB0031374 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

3D MOL for HMDB0031374 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

3D SDF for HMDB0031374 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

3D-SDF for HMDB0031374 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

PDB for HMDB0031374 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

3D PDB for HMDB0031374 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

SMILES for HMDB0031374 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

INCHI for HMDB0031374 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

Structure for HMDB0031374 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

3D Structure for HMDB0031374 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra