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Showing metabocard for Epomusenin A (HMDB0029982)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:58 UTC
Update Date2022-03-07 02:52:23 UTC
HMDB IDHMDB0029982
Secondary Accession Numbers
  • HMDB29982
Metabolite Identification
Common NameEpomusenin A
DescriptionEpomusenin 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
Data?1563861920
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029982 (Epomusenin A)


  Mrv0541 05061304572D          

 40 41  0  0  0  0            999 V2000
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M  END
Download

3D MOL for HMDB0029982 (Epomusenin A)

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
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   -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
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 37106  1  0
M  END
Download

3D SDF for HMDB0029982 (Epomusenin A)


  Mrv0541 05061304572D          

 40 41  0  0  0  0            999 V2000
  -15.9987    5.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2597    9.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2842    6.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5698    5.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8553    6.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1408    5.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4263    6.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7119    5.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9974    6.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2829    5.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5685    6.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5823    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8466    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8540    5.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0267   10.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  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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 40 36  1  0  0  0  0
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

$$$$
Download

3D-SDF for HMDB0029982 (Epomusenin A)

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
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    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
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 39 40  2  0
 19 17  1  0
 39 34  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  2 44  1  0
  2 45  1  0
  3 46  1  0
  3 47  1  0
  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
Download

PDB for HMDB0029982 (Epomusenin A)

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
Download

3D PDB for HMDB0029982 (Epomusenin A)

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
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SMILES for HMDB0029982 (Epomusenin A)

CCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCCCC1=CC(C)OC1=O
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INCHI for HMDB0029982 (Epomusenin A)

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-
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC37H66O3
Average Molecular Weight558.9181
Monoisotopic Molecular Weight558.501195978
IUPAC Name3-(14-{3-[(3Z)-hexadec-3-en-1-yl]oxiran-2-yl}tetradecyl)-5-methyl-2,5-dihydrofuran-2-one
Traditional Name3-(14-{3-[(3Z)-hexadec-3-en-1-yl]oxiran-2-yl}tetradecyl)-5-methyl-5H-furan-2-one
CAS Registry Number178330-55-7
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 KeyCQXDIWLWKUBMCF-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentAnnonaceous 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 FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.7e-10 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.0e-05 g/LALOGPS
logP10.74ALOGPS
logP13.47ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)15.12ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.83 ŲChemAxon
Rotatable Bond Count29ChemAxon
Refractivity173.29 m³·mol⁻¹ChemAxon
Polarizability75.39 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+243.02331661259
DarkChem[M-H]-242.55831661259
DeepCCS[M+H]+251.23630932474
DeepCCS[M-H]-248.07930932474
DeepCCS[M-2H]-283.76130932474
DeepCCS[M+Na]+260.05130932474
AllCCS[M+H]+258.032859911
AllCCS[M+H-H2O]+256.732859911
AllCCS[M+NH4]+259.232859911
AllCCS[M+Na]+259.532859911
AllCCS[M-H]-244.032859911
AllCCS[M+Na-2H]-249.632859911
AllCCS[M+HCOO]-255.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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. Predicted by Afia on May 17, 2022.8.79 minutes32390414
Predicted by Siyang on May 30, 202244.667 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20220.7 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid5724.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid1257.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid486.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid662.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid1072.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid1987.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid1693.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)128.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid4249.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid1160.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid3393.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid1595.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid947.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate1130.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA1123.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water10.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Epomusenin ACCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCCCC1=CC(C)OC1=O4903.7Standard polar33892256
Epomusenin ACCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCCCC1=CC(C)OC1=O4075.7Standard non polar33892256
Epomusenin ACCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCCCC1=CC(C)OC1=O4347.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epomusenin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4s-2294400000-45956a51490e83ba5e232017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 10V, Positive-QTOFsplash10-0a4i-0011190000-4664cc339a731bd98cc42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 20V, Positive-QTOFsplash10-0a4u-1291230000-b629465209aa11f4b4532016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 40V, Positive-QTOFsplash10-0a4r-2491500000-c3c04ab520f5edd849682016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 10V, Negative-QTOFsplash10-0a4i-0011090000-9e183e6c419e92c99fb62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 20V, Negative-QTOFsplash10-0bt9-1031090000-7489177498eb8e7001c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 40V, Negative-QTOFsplash10-01p6-2090000000-4b2a89494330b812e6382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 10V, Negative-QTOFsplash10-0a4i-0000090000-245c651b8a21489bd15f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 20V, Negative-QTOFsplash10-0a4i-2012090000-e782c8e62c4677726cb82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 40V, Negative-QTOFsplash10-03dr-4215290000-d1c9bd4f762303b8ac792021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 10V, Positive-QTOFsplash10-0a4l-0011190000-3557f72772c5a4817ba92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 20V, Positive-QTOFsplash10-06xx-1001090000-c36711e3c3843b5764272021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin A 40V, Positive-QTOFsplash10-0536-9100000000-704aedd1f318e51082772021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001269
KNApSAcK IDC00044156
Chemspider ID8682451
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10507050
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1812761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.