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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:33:58 UTC

Update Date

2022-03-07 02:52:23 UTC

HMDB ID

HMDB0029982

Secondary Accession Numbers

HMDB29982

Metabolite Identification

Common Name

Epomusenin A

Description

Epomusenin A belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Based on a literature review a small amount of articles have been published on Epomusenin A.

Structure

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


  Mrv0541 05061304572D          

 40 41  0  0  0  0            999 V2000
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M  END

HMDB0029982
     RDKit          3D
Epomusenin A
106107  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 05061304572D          

 40 41  0  0  0  0            999 V2000
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    4.6066   10.9274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4086    9.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
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 33  2  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0029982

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCCCC1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O3/c1-3-4-5-6-7-8-9-10-11-15-18-21-24-27-30-35-36(40-35)31-28-25-22-19-16-13-12-14-17-20-23-26-29-34-32-33(2)39-37(34)38/h21,24,32-33,35-36H,3-20,22-23,25-31H2,1-2H3/b24-21-

> <INCHI_KEY>
CQXDIWLWKUBMCF-FLFQWRMESA-N

> <FORMULA>
C37H66O3

> <MOLECULAR_WEIGHT>
558.9181

> <EXACT_MASS>
558.501195978

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
75.39101562157921

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(14-{3-[(3Z)-hexadec-3-en-1-yl]oxiran-2-yl}tetradecyl)-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
10.74

> <JCHEM_LOGP>
13.468529499333334

> <ALOGPS_LOGS>
-7.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.115322232239539

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2017282866762695

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
173.2918

> <JCHEM_ROTATABLE_BOND_COUNT>
29

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(14-{3-[(3Z)-hexadec-3-en-1-yl]oxiran-2-yl}tetradecyl)-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029982
     RDKit          3D
Epomusenin A
106107  0  0  0  0  0  0  0  0999 V2000
   -8.0841   -3.6839    3.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0232   -2.5316    2.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 48  1  0
  4 49  1  0
  5 50  1  0
  5 51  1  0
  6 52  1  0
  6 53  1  0
  7 54  1  0
  7 55  1  0
  8 56  1  0
  8 57  1  0
  9 58  1  0
  9 59  1  0
 10 60  1  0
 10 61  1  0
 11 62  1  0
 11 63  1  0
 12 64  1  0
 12 65  1  0
 13 66  1  0
 14 67  1  0
 15 68  1  0
 15 69  1  0
 16 70  1  0
 16 71  1  0
 17 72  1  0
 19 73  1  0
 20 74  1  0
 20 75  1  0
 21 76  1  0
 21 77  1  0
 22 78  1  0
 22 79  1  0
 23 80  1  0
 23 81  1  0
 24 82  1  0
 24 83  1  0
 25 84  1  0
 25 85  1  0
 26 86  1  0
 26 87  1  0
 27 88  1  0
 27 89  1  0
 28 90  1  0
 28 91  1  0
 29 92  1  0
 29 93  1  0
 30 94  1  0
 30 95  1  0
 31 96  1  0
 31 97  1  0
 32 98  1  0
 32 99  1  0
 33100  1  0
 33101  1  0
 35102  1  0
 36103  1  0
 37104  1  0
 37105  1  0
 37106  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     -29.864  11.112   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.551  18.193   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -28.531  11.882   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -27.197  11.112   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -25.863  11.882   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -24.529  11.112   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -23.196  11.882   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -21.862  11.112   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -20.528  11.882   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -19.195  11.112   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -17.861  11.882   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.247  17.066   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.087  17.836   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.580  17.836   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -16.527  11.112   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.421  17.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.914  17.066   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -15.194  11.882   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.754  17.836   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.248  17.836   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -13.860  11.112   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.088  17.066   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.582  17.066   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -12.526  11.882   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.422  17.836   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.915  17.836   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -12.526  13.422   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.755  17.066   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.249  17.066   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -11.193  14.192   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -9.089  17.836   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.989  17.209   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.020  18.354   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.583  17.836   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -11.193  15.732   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.423  17.066   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.743  19.367   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.599  20.398   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      11.250  19.688   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -11.963  17.066   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   33                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   15                                                       
CONECT   12   13   14                                                       
CONECT   13   12   16                                                       
CONECT   14   12   17                                                       
CONECT   15   11   18                                                       
CONECT   16   13   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15   21                                                       
CONECT   19   16   22                                                       
CONECT   20   17   23                                                       
CONECT   21   18   24                                                       
CONECT   22   19   25                                                       
CONECT   23   20   26                                                       
CONECT   24   21   27                                                       
CONECT   25   22   28                                                       
CONECT   26   23   29                                                       
CONECT   27   24   30                                                       
CONECT   28   25   31                                                       
CONECT   29   26   34                                                       
CONECT   30   27   35                                                       
CONECT   31   28   36                                                       
CONECT   32   33   34                                                       
CONECT   33    2   32   39                                                  
CONECT   34   29   32   37                                                  
CONECT   35   30   36   40                                                  
CONECT   36   31   35   40                                                  
CONECT   37   34   38   39                                                  
CONECT   38   37                                                            
CONECT   39   33   37                                                       
CONECT   40   35   36                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

COMPND    HMDB0029982
HETATM    1  C1  UNL     1      -8.084  -3.684   3.016  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.023  -2.532   2.516  1.00  0.00           C  
HETATM    3  C3  UNL     1      -9.940  -3.161   1.538  1.00  0.00           C  
HETATM    4  C4  UNL     1     -11.023  -2.360   0.977  1.00  0.00           C  
HETATM    5  C5  UNL     1     -10.758  -1.111   0.238  1.00  0.00           C  
HETATM    6  C6  UNL     1     -10.214   0.035   0.981  1.00  0.00           C  
HETATM    7  C7  UNL     1     -10.019   1.272   0.118  1.00  0.00           C  
HETATM    8  C8  UNL     1      -9.074   1.070  -1.034  1.00  0.00           C  
HETATM    9  C9  UNL     1      -9.011   2.396  -1.761  1.00  0.00           C  
HETATM   10  C10 UNL     1      -8.146   2.466  -2.933  1.00  0.00           C  
HETATM   11  C11 UNL     1      -6.720   2.189  -2.928  1.00  0.00           C  
HETATM   12  C12 UNL     1      -5.838   3.034  -2.081  1.00  0.00           C  
HETATM   13  C13 UNL     1      -6.084   2.878  -0.658  1.00  0.00           C  
HETATM   14  C14 UNL     1      -5.176   2.447   0.197  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.809   2.070  -0.171  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.642   0.587   0.229  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.273   0.072  -0.068  1.00  0.00           C  
HETATM   18  O1  UNL     1      -1.729   0.047  -1.325  1.00  0.00           O  
HETATM   19  C18 UNL     1      -1.313   1.111  -0.565  1.00  0.00           C  
HETATM   20  C19 UNL     1       0.048   1.104   0.120  1.00  0.00           C  
HETATM   21  C20 UNL     1       0.758  -0.183  -0.048  1.00  0.00           C  
HETATM   22  C21 UNL     1       2.085  -0.238   0.594  1.00  0.00           C  
HETATM   23  C22 UNL     1       3.172   0.565   0.027  1.00  0.00           C  
HETATM   24  C23 UNL     1       3.078   2.019  -0.139  1.00  0.00           C  
HETATM   25  C24 UNL     1       4.412   2.622  -0.641  1.00  0.00           C  
HETATM   26  C25 UNL     1       5.543   2.405   0.317  1.00  0.00           C  
HETATM   27  C26 UNL     1       6.808   3.040  -0.235  1.00  0.00           C  
HETATM   28  C27 UNL     1       7.936   2.847   0.724  1.00  0.00           C  
HETATM   29  C28 UNL     1       8.292   1.423   1.025  1.00  0.00           C  
HETATM   30  C29 UNL     1       8.674   0.647  -0.187  1.00  0.00           C  
HETATM   31  C30 UNL     1       9.058  -0.795   0.151  1.00  0.00           C  
HETATM   32  C31 UNL     1      10.221  -0.864   1.049  1.00  0.00           C  
HETATM   33  C32 UNL     1      10.703  -2.189   1.517  1.00  0.00           C  
HETATM   34  C33 UNL     1      11.070  -3.143   0.451  1.00  0.00           C  
HETATM   35  C34 UNL     1      12.336  -3.546   0.273  1.00  0.00           C  
HETATM   36  C35 UNL     1      12.382  -4.479  -0.851  1.00  0.00           C  
HETATM   37  C36 UNL     1      13.002  -5.769  -0.338  1.00  0.00           C  
HETATM   38  O2  UNL     1      11.050  -4.716  -1.191  1.00  0.00           O  
HETATM   39  C37 UNL     1      10.219  -3.873  -0.470  1.00  0.00           C  
HETATM   40  O3  UNL     1       8.961  -3.762  -0.583  1.00  0.00           O  
HETATM   41  H1  UNL     1      -7.481  -3.941   2.128  1.00  0.00           H  
HETATM   42  H2  UNL     1      -7.524  -3.337   3.882  1.00  0.00           H  
HETATM   43  H3  UNL     1      -8.800  -4.520   3.230  1.00  0.00           H  
HETATM   44  H4  UNL     1      -9.437  -2.023   3.358  1.00  0.00           H  
HETATM   45  H5  UNL     1      -8.309  -1.840   1.979  1.00  0.00           H  
HETATM   46  H6  UNL     1     -10.419  -4.094   2.027  1.00  0.00           H  
HETATM   47  H7  UNL     1      -9.356  -3.659   0.699  1.00  0.00           H  
HETATM   48  H8  UNL     1     -11.654  -3.078   0.330  1.00  0.00           H  
HETATM   49  H9  UNL     1     -11.822  -2.121   1.789  1.00  0.00           H  
HETATM   50  H10 UNL     1     -11.740  -0.794  -0.219  1.00  0.00           H  
HETATM   51  H11 UNL     1     -10.031  -1.322  -0.613  1.00  0.00           H  
HETATM   52  H12 UNL     1      -9.342  -0.063   1.599  1.00  0.00           H  
HETATM   53  H13 UNL     1     -11.044   0.349   1.713  1.00  0.00           H  
HETATM   54  H14 UNL     1      -9.685   2.103   0.757  1.00  0.00           H  
HETATM   55  H15 UNL     1     -11.038   1.536  -0.273  1.00  0.00           H  
HETATM   56  H16 UNL     1      -8.081   0.830  -0.624  1.00  0.00           H  
HETATM   57  H17 UNL     1      -9.425   0.256  -1.704  1.00  0.00           H  
HETATM   58  H18 UNL     1     -10.120   2.478  -2.164  1.00  0.00           H  
HETATM   59  H19 UNL     1      -9.014   3.214  -1.042  1.00  0.00           H  
HETATM   60  H20 UNL     1      -8.640   1.827  -3.752  1.00  0.00           H  
HETATM   61  H21 UNL     1      -8.336   3.514  -3.391  1.00  0.00           H  
HETATM   62  H22 UNL     1      -6.313   2.321  -3.997  1.00  0.00           H  
HETATM   63  H23 UNL     1      -6.464   1.119  -2.665  1.00  0.00           H  
HETATM   64  H24 UNL     1      -4.798   2.852  -2.430  1.00  0.00           H  
HETATM   65  H25 UNL     1      -6.083   4.118  -2.402  1.00  0.00           H  
HETATM   66  H26 UNL     1      -7.053   3.130  -0.185  1.00  0.00           H  
HETATM   67  H27 UNL     1      -5.474   2.361   1.292  1.00  0.00           H  
HETATM   68  H28 UNL     1      -3.629   2.198  -1.234  1.00  0.00           H  
HETATM   69  H29 UNL     1      -3.075   2.642   0.459  1.00  0.00           H  
HETATM   70  H30 UNL     1      -4.458   0.015  -0.266  1.00  0.00           H  
HETATM   71  H31 UNL     1      -3.808   0.544   1.318  1.00  0.00           H  
HETATM   72  H32 UNL     1      -1.872  -0.720   0.603  1.00  0.00           H  
HETATM   73  H33 UNL     1      -1.642   2.100  -0.884  1.00  0.00           H  
HETATM   74  H34 UNL     1      -0.175   1.188   1.236  1.00  0.00           H  
HETATM   75  H35 UNL     1       0.584   1.979  -0.149  1.00  0.00           H  
HETATM   76  H36 UNL     1       0.911  -0.396  -1.164  1.00  0.00           H  
HETATM   77  H37 UNL     1       0.106  -1.013   0.343  1.00  0.00           H  
HETATM   78  H38 UNL     1       2.418  -1.320   0.755  1.00  0.00           H  
HETATM   79  H39 UNL     1       1.911   0.133   1.674  1.00  0.00           H  
HETATM   80  H40 UNL     1       4.114   0.272   0.617  1.00  0.00           H  
HETATM   81  H41 UNL     1       3.479   0.162  -1.015  1.00  0.00           H  
HETATM   82  H42 UNL     1       2.713   2.599   0.712  1.00  0.00           H  
HETATM   83  H43 UNL     1       2.413   2.291  -1.042  1.00  0.00           H  
HETATM   84  H44 UNL     1       4.187   3.683  -0.815  1.00  0.00           H  
HETATM   85  H45 UNL     1       4.580   2.168  -1.636  1.00  0.00           H  
HETATM   86  H46 UNL     1       5.733   1.367   0.586  1.00  0.00           H  
HETATM   87  H47 UNL     1       5.273   2.954   1.253  1.00  0.00           H  
HETATM   88  H48 UNL     1       7.103   2.592  -1.200  1.00  0.00           H  
HETATM   89  H49 UNL     1       6.689   4.127  -0.396  1.00  0.00           H  
HETATM   90  H50 UNL     1       8.803   3.430   0.334  1.00  0.00           H  
HETATM   91  H51 UNL     1       7.592   3.290   1.700  1.00  0.00           H  
HETATM   92  H52 UNL     1       9.112   1.475   1.799  1.00  0.00           H  
HETATM   93  H53 UNL     1       7.445   0.959   1.572  1.00  0.00           H  
HETATM   94  H54 UNL     1       9.470   1.100  -0.782  1.00  0.00           H  
HETATM   95  H55 UNL     1       7.764   0.553  -0.828  1.00  0.00           H  
HETATM   96  H56 UNL     1       9.292  -1.258  -0.861  1.00  0.00           H  
HETATM   97  H57 UNL     1       8.189  -1.313   0.565  1.00  0.00           H  
HETATM   98  H58 UNL     1      11.064  -0.299   0.542  1.00  0.00           H  
HETATM   99  H59 UNL     1      10.020  -0.255   1.979  1.00  0.00           H  
HETATM  100  H60 UNL     1      11.583  -2.067   2.225  1.00  0.00           H  
HETATM  101  H61 UNL     1       9.932  -2.674   2.209  1.00  0.00           H  
HETATM  102  H62 UNL     1      13.203  -3.224   0.878  1.00  0.00           H  
HETATM  103  H63 UNL     1      12.975  -4.077  -1.712  1.00  0.00           H  
HETATM  104  H64 UNL     1      13.150  -5.756   0.764  1.00  0.00           H  
HETATM  105  H65 UNL     1      14.001  -5.939  -0.776  1.00  0.00           H  
HETATM  106  H66 UNL     1      12.400  -6.665  -0.558  1.00  0.00           H  
CONECT    1    2   41   42   43
CONECT    2    3   44   45
CONECT    3    4   46   47
CONECT    4    5   48   49
CONECT    5    6   50   51
CONECT    6    7   52   53
CONECT    7    8   54   55
CONECT    8    9   56   57
CONECT    9   10   58   59
CONECT   10   11   60   61
CONECT   11   12   62   63
CONECT   12   13   64   65
CONECT   13   14   14   66
CONECT   14   15   67
CONECT   15   16   68   69
CONECT   16   17   70   71
CONECT   17   18   19   72
CONECT   18   19
CONECT   19   20   73
CONECT   20   21   74   75
CONECT   21   22   76   77
CONECT   22   23   78   79
CONECT   23   24   80   81
CONECT   24   25   82   83
CONECT   25   26   84   85
CONECT   26   27   86   87
CONECT   27   28   88   89
CONECT   28   29   90   91
CONECT   29   30   92   93
CONECT   30   31   94   95
CONECT   31   32   96   97
CONECT   32   33   98   99
CONECT   33   34  100  101
CONECT   34   35   35   39
CONECT   35   36  102
CONECT   36   37   38  103
CONECT   37  104  105  106
CONECT   38   39
CONECT   39   40   40
END

HMDB0029982
     RDKit          3D
Epomusenin A
106107  0  0  0  0  0  0  0  0999 V2000
   -8.0841   -3.6839    3.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0232   -2.5316    2.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9399   -3.1607    1.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0228   -2.3597    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7577   -1.1112    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2139    0.0348    0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0194    1.2724    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0745    1.0699   -1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0110    2.3964   -1.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1457    2.4663   -2.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7200    2.1891   -2.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8384    3.0335   -2.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0836    2.8780   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1765    2.4468    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8090    2.0697   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6423    0.5867    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2726    0.0724   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292    0.0471   -1.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130    1.1115   -0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0484    1.1037    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7585   -0.1827   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0848   -0.2383    0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1720    0.5645    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0780    2.0195   -0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123    2.6217   -0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0576   -0.7946    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3358   -3.5461    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.0021   -5.7695   -0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0500   -4.7160   -1.1913 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2185   -3.8734   -0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5922    3.2901    1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1117    1.4749    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1891   -1.3134    0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0645   -0.2990    0.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0198   -0.2554    1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9754   -4.0769   -1.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3996   -6.6650   -0.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₇H₆₆O₃

Average Molecular Weight

558.9181

Monoisotopic Molecular Weight

558.501195978

IUPAC Name

3-(14-{3-[(3Z)-hexadec-3-en-1-yl]oxiran-2-yl}tetradecyl)-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

3-(14-{3-[(3Z)-hexadec-3-en-1-yl]oxiran-2-yl}tetradecyl)-5-methyl-5H-furan-2-one

CAS Registry Number

178330-55-7

SMILES

CCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCCCC1=CC(C)OC1=O

InChI Identifier

InChI=1S/C37H66O3/c1-3-4-5-6-7-8-9-10-11-15-18-21-24-27-30-35-36(40-35)31-28-25-22-19-16-13-12-14-17-20-23-26-29-34-32-33(2)39-37(34)38/h21,24,32-33,35-36H,3-20,22-23,25-31H2,1-2H3/b24-21-

InChI Key

CQXDIWLWKUBMCF-FLFQWRMESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
2-furanone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0029982)
Cell membrane (HMDB: HMDB0029982)

Biofluid or Excreta

Urine (HMDB: HMDB0029982)

Cellular substructure

Membrane (HMDB: HMDB0029982)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029982)

Source

Endogenous

Endogenous (HMDB: HMDB0029982)

Plant

Plant (HMDB: HMDB0029982)

Animal

Animal (HMDB: HMDB0029982)

Exogenous

Food

Food (HMDB: HMDB0029982)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0029982)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0029982)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0029982)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0029982)

Nutrient

Nutrient (HMDB: HMDB0029982)

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	3.7e-10 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.0e-05 g/L	ALOGPS
logP	10.74	ALOGPS
logP	13.47	ChemAxon
logS	-7.7	ALOGPS
pKa (Strongest Acidic)	15.12	ChemAxon
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	29	ChemAxon
Refractivity	173.29 m³·mol⁻¹	ChemAxon
Polarizability	75.39 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	243.023	31661259
DarkChem	[M-H]-	242.558	31661259
DeepCCS	[M+H]+	251.236	30932474
DeepCCS	[M-H]-	248.079	30932474
DeepCCS	[M-2H]-	283.761	30932474
DeepCCS	[M+Na]+	260.051	30932474
AllCCS	[M+H]+	258.0	32859911
AllCCS	[M+H-H2O]+	256.7	32859911
AllCCS	[M+NH4]+	259.2	32859911
AllCCS	[M+Na]+	259.5	32859911
AllCCS	[M-H]-	244.0	32859911
AllCCS	[M+Na-2H]-	249.6	32859911
AllCCS	[M+HCOO]-	255.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epomusenin A	CCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCCCC1=CC(C)OC1=O	4903.7	Standard polar	33892256
Epomusenin A	CCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCCCC1=CC(C)OC1=O	4075.7	Standard non polar	33892256
Epomusenin A	CCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCCCC1=CC(C)OC1=O	4347.3	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 - Epomusenin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4s-2294400000-45956a51490e83ba5e23	2017-09-01	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 - Epomusenin A 10V, Positive-QTOF	splash10-0a4i-0011190000-4664cc339a731bd98cc4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 20V, Positive-QTOF	splash10-0a4u-1291230000-b629465209aa11f4b453	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 40V, Positive-QTOF	splash10-0a4r-2491500000-c3c04ab520f5edd84968	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 10V, Negative-QTOF	splash10-0a4i-0011090000-9e183e6c419e92c99fb6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 20V, Negative-QTOF	splash10-0bt9-1031090000-7489177498eb8e7001c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 40V, Negative-QTOF	splash10-01p6-2090000000-4b2a89494330b812e638	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 10V, Negative-QTOF	splash10-0a4i-0000090000-245c651b8a21489bd15f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 20V, Negative-QTOF	splash10-0a4i-2012090000-e782c8e62c4677726cb8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 40V, Negative-QTOF	splash10-03dr-4215290000-d1c9bd4f762303b8ac79	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 10V, Positive-QTOF	splash10-0a4l-0011190000-3557f72772c5a4817ba9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 20V, Positive-QTOF	splash10-06xx-1001090000-c36711e3c3843b576427	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epomusenin A 40V, Positive-QTOF	splash10-0536-9100000000-704aedd1f318e5108277	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB001269

KNApSAcK ID

C00044156

Chemspider ID

8682451

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10507050

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1812761

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 Epomusenin A (HMDB0029982)

MOL for HMDB0029982 (Epomusenin A)

3D MOL for HMDB0029982 (Epomusenin A)

3D SDF for HMDB0029982 (Epomusenin A)

3D-SDF for HMDB0029982 (Epomusenin A)

PDB for HMDB0029982 (Epomusenin A)

3D PDB for HMDB0029982 (Epomusenin A)

SMILES for HMDB0029982 (Epomusenin A)

INCHI for HMDB0029982 (Epomusenin A)

Structure for HMDB0029982 (Epomusenin A)

3D Structure for HMDB0029982 (Epomusenin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra