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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:21:16 UTC

Update Date

2022-03-07 02:53:47 UTC

HMDB ID

HMDB0033607

Secondary Accession Numbers

HMDB33607

Metabolite Identification

Common Name

Artemoin D

Description

Artemoin D 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 significant number of articles have been published on Artemoin D.

Structure

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


  Mrv0541 05061307142D          

 39 39  0  0  0  0            999 V2000
   -9.5188   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0416   20.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8043   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0898   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3753   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6609   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9464   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2319   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5175   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8030   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3740   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6286   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3430   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  1  1  0  0  0  0
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 39 31  1  0  0  0  0
 39 35  1  0  0  0  0
M  END

HMDB0033607
     RDKit          3D
Artemoin D
105105  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 05061307142D          

 39 39  0  0  0  0            999 V2000
   -9.5188   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0033607

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H66O4/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-25-28-33(36)34(37)29-26-23-20-17-14-13-15-18-21-24-27-32-30-31(2)39-35(32)38/h30-31,33-34,36-37H,3-29H2,1-2H3

> <INCHI_KEY>
CAGLXILDKKCMCR-UHFFFAOYSA-N

> <FORMULA>
C35H66O4

> <MOLECULAR_WEIGHT>
550.8961

> <EXACT_MASS>
550.4961106

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
74.23462967356853

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(13,14-dihydroxytriacontyl)-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
9.85

> <JCHEM_LOGP>
11.779610253666664

> <ALOGPS_LOGS>
-7.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.941437150411005

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.883475303328535

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1440192571762076

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
166.4833

> <JCHEM_ROTATABLE_BOND_COUNT>
29

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.93e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(13,14-dihydroxytriacontyl)-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033607
     RDKit          3D
Artemoin D
105105  0  0  0  0  0  0  0  0999 V2000
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 24 83  1  0
 24 84  1  0
 25 85  1  0
 25 86  1  0
 26 87  1  0
 26 88  1  0
 27 89  1  0
 27 90  1  0
 28 91  1  0
 28 92  1  0
 29 93  1  0
 29 94  1  0
 30 95  1  0
 30 96  1  0
 31 97  1  0
 31 98  1  0
 32 99  1  0
 32100  1  0
 34101  1  0
 35102  1  0
 36103  1  0
 36104  1  0
 36105  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     -17.768  37.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.211  37.687   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -16.435  36.560   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -15.101  37.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.767  36.560   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.434  37.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.100  36.560   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.766  37.330   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.433  36.560   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.099  37.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.765  36.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.431  37.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.240  37.330   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.906  36.560   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.574  36.560   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.098  36.560   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.573  37.330   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.907  37.330   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.764  37.330   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.239  36.560   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.241  36.560   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.430  36.560   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.905  37.330   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.575  37.330   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.903  37.330   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.572  36.560   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.908  36.560   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.237  36.560   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.238  37.330   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.649  36.703   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.679  37.848   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.242  37.330   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.571  37.330   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.904  36.560   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.403  38.861   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.571  38.870   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.904  35.020   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      21.259  39.892   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      23.909  39.182   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   31                                                            
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   12                                                       
CONECT   12   11   16                                                       
CONECT   13   14   15                                                       
CONECT   14   13   17                                                       
CONECT   15   13   18                                                       
CONECT   16   12   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   32                                                       
CONECT   28   25   33                                                       
CONECT   29   26   34                                                       
CONECT   30   31   32                                                       
CONECT   31    2   30   39                                                  
CONECT   32   27   30   35                                                  
CONECT   33   28   34   36                                                  
CONECT   34   29   33   37                                                  
CONECT   35   32   38   39                                                  
CONECT   36   33                                                            
CONECT   37   34                                                            
CONECT   38   35                                                            
CONECT   39   31   35                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

COMPND    HMDB0033607
HETATM    1  C1  UNL     1     -11.489   1.593  -0.576  1.00  0.00           C  
HETATM    2  C2  UNL     1     -12.567   1.537   0.489  1.00  0.00           C  
HETATM    3  C3  UNL     1     -12.014   0.933   1.763  1.00  0.00           C  
HETATM    4  C4  UNL     1     -11.533  -0.455   1.463  1.00  0.00           C  
HETATM    5  C5  UNL     1     -10.970  -1.113   2.715  1.00  0.00           C  
HETATM    6  C6  UNL     1     -10.522  -2.488   2.321  1.00  0.00           C  
HETATM    7  C7  UNL     1      -9.470  -2.527   1.263  1.00  0.00           C  
HETATM    8  C8  UNL     1      -8.208  -1.796   1.731  1.00  0.00           C  
HETATM    9  C9  UNL     1      -7.235  -1.884   0.617  1.00  0.00           C  
HETATM   10  C10 UNL     1      -5.893  -1.204   0.887  1.00  0.00           C  
HETATM   11  C11 UNL     1      -6.034   0.230   1.171  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.849   0.998   1.515  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.678   1.165   0.656  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.868  -0.029   0.375  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.687   0.303  -0.586  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.773   1.332  -0.040  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.325   1.695  -0.964  1.00  0.00           C  
HETATM   18  O1  UNL     1      -0.136   2.195  -2.200  1.00  0.00           O  
HETATM   19  C18 UNL     1       1.459   0.774  -1.170  1.00  0.00           C  
HETATM   20  O2  UNL     1       1.915   0.198   0.017  1.00  0.00           O  
HETATM   21  C19 UNL     1       1.328  -0.272  -2.214  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.598  -1.106  -2.279  1.00  0.00           C  
HETATM   23  C21 UNL     1       3.780  -0.265  -2.644  1.00  0.00           C  
HETATM   24  C22 UNL     1       5.042  -1.110  -2.741  1.00  0.00           C  
HETATM   25  C23 UNL     1       6.180  -0.231  -3.132  1.00  0.00           C  
HETATM   26  C24 UNL     1       6.489   0.874  -2.157  1.00  0.00           C  
HETATM   27  C25 UNL     1       6.883   0.246  -0.835  1.00  0.00           C  
HETATM   28  C26 UNL     1       7.218   1.209   0.214  1.00  0.00           C  
HETATM   29  C27 UNL     1       8.238   2.227   0.115  1.00  0.00           C  
HETATM   30  C28 UNL     1       9.657   2.133  -0.043  1.00  0.00           C  
HETATM   31  C29 UNL     1      10.439   1.597  -1.139  1.00  0.00           C  
HETATM   32  C30 UNL     1      10.380   0.158  -1.466  1.00  0.00           C  
HETATM   33  C31 UNL     1      10.785  -0.688  -0.292  1.00  0.00           C  
HETATM   34  C32 UNL     1      10.119  -1.606   0.347  1.00  0.00           C  
HETATM   35  C33 UNL     1      10.924  -2.170   1.437  1.00  0.00           C  
HETATM   36  C34 UNL     1      10.220  -1.820   2.741  1.00  0.00           C  
HETATM   37  O3  UNL     1      12.137  -1.471   1.363  1.00  0.00           O  
HETATM   38  C35 UNL     1      12.101  -0.558   0.324  1.00  0.00           C  
HETATM   39  O4  UNL     1      13.012   0.243  -0.043  1.00  0.00           O  
HETATM   40  H1  UNL     1     -11.465   0.712  -1.220  1.00  0.00           H  
HETATM   41  H2  UNL     1     -10.513   1.677  -0.032  1.00  0.00           H  
HETATM   42  H3  UNL     1     -11.623   2.520  -1.183  1.00  0.00           H  
HETATM   43  H4  UNL     1     -12.982   2.517   0.724  1.00  0.00           H  
HETATM   44  H5  UNL     1     -13.425   0.896   0.154  1.00  0.00           H  
HETATM   45  H6  UNL     1     -11.222   1.544   2.214  1.00  0.00           H  
HETATM   46  H7  UNL     1     -12.865   0.859   2.490  1.00  0.00           H  
HETATM   47  H8  UNL     1     -12.376  -1.060   1.089  1.00  0.00           H  
HETATM   48  H9  UNL     1     -10.763  -0.389   0.664  1.00  0.00           H  
HETATM   49  H10 UNL     1     -10.112  -0.536   3.100  1.00  0.00           H  
HETATM   50  H11 UNL     1     -11.777  -1.223   3.456  1.00  0.00           H  
HETATM   51  H12 UNL     1     -11.411  -3.072   1.974  1.00  0.00           H  
HETATM   52  H13 UNL     1     -10.125  -3.020   3.216  1.00  0.00           H  
HETATM   53  H14 UNL     1      -9.821  -2.159   0.278  1.00  0.00           H  
HETATM   54  H15 UNL     1      -9.152  -3.585   1.123  1.00  0.00           H  
HETATM   55  H16 UNL     1      -7.915  -2.270   2.670  1.00  0.00           H  
HETATM   56  H17 UNL     1      -8.521  -0.724   1.844  1.00  0.00           H  
HETATM   57  H18 UNL     1      -7.001  -2.945   0.367  1.00  0.00           H  
HETATM   58  H19 UNL     1      -7.694  -1.449  -0.292  1.00  0.00           H  
HETATM   59  H20 UNL     1      -5.405  -1.296  -0.140  1.00  0.00           H  
HETATM   60  H21 UNL     1      -5.297  -1.761   1.583  1.00  0.00           H  
HETATM   61  H22 UNL     1      -6.763   0.377   2.053  1.00  0.00           H  
HETATM   62  H23 UNL     1      -6.626   0.733   0.341  1.00  0.00           H  
HETATM   63  H24 UNL     1      -5.236   2.031   1.868  1.00  0.00           H  
HETATM   64  H25 UNL     1      -4.461   0.608   2.534  1.00  0.00           H  
HETATM   65  H26 UNL     1      -2.981   1.873   1.242  1.00  0.00           H  
HETATM   66  H27 UNL     1      -3.876   1.791  -0.262  1.00  0.00           H  
HETATM   67  H28 UNL     1      -2.306  -0.359   1.312  1.00  0.00           H  
HETATM   68  H29 UNL     1      -3.325  -0.896  -0.100  1.00  0.00           H  
HETATM   69  H30 UNL     1      -2.093   0.507  -1.577  1.00  0.00           H  
HETATM   70  H31 UNL     1      -1.146  -0.693  -0.637  1.00  0.00           H  
HETATM   71  H32 UNL     1      -1.389   2.255   0.180  1.00  0.00           H  
HETATM   72  H33 UNL     1      -0.406   0.986   0.959  1.00  0.00           H  
HETATM   73  H34 UNL     1       0.788   2.653  -0.495  1.00  0.00           H  
HETATM   74  H35 UNL     1      -0.486   1.448  -2.752  1.00  0.00           H  
HETATM   75  H36 UNL     1       2.309   1.457  -1.566  1.00  0.00           H  
HETATM   76  H37 UNL     1       1.617   0.704   0.813  1.00  0.00           H  
HETATM   77  H38 UNL     1       0.509  -0.978  -2.125  1.00  0.00           H  
HETATM   78  H39 UNL     1       1.200   0.190  -3.245  1.00  0.00           H  
HETATM   79  H40 UNL     1       2.794  -1.498  -1.242  1.00  0.00           H  
HETATM   80  H41 UNL     1       2.462  -1.992  -2.908  1.00  0.00           H  
HETATM   81  H42 UNL     1       3.605   0.254  -3.588  1.00  0.00           H  
HETATM   82  H43 UNL     1       3.977   0.430  -1.776  1.00  0.00           H  
HETATM   83  H44 UNL     1       5.181  -1.627  -1.775  1.00  0.00           H  
HETATM   84  H45 UNL     1       4.892  -1.865  -3.520  1.00  0.00           H  
HETATM   85  H46 UNL     1       7.133  -0.830  -3.212  1.00  0.00           H  
HETATM   86  H47 UNL     1       5.957   0.186  -4.138  1.00  0.00           H  
HETATM   87  H48 UNL     1       7.319   1.465  -2.597  1.00  0.00           H  
HETATM   88  H49 UNL     1       5.637   1.583  -2.029  1.00  0.00           H  
HETATM   89  H50 UNL     1       5.868  -0.219  -0.485  1.00  0.00           H  
HETATM   90  H51 UNL     1       7.484  -0.635  -0.987  1.00  0.00           H  
HETATM   91  H52 UNL     1       6.238   1.664   0.593  1.00  0.00           H  
HETATM   92  H53 UNL     1       7.503   0.558   1.133  1.00  0.00           H  
HETATM   93  H54 UNL     1       7.893   3.057  -0.646  1.00  0.00           H  
HETATM   94  H55 UNL     1       8.075   2.891   1.081  1.00  0.00           H  
HETATM   95  H56 UNL     1      10.060   3.237   0.097  1.00  0.00           H  
HETATM   96  H57 UNL     1      10.131   1.723   0.967  1.00  0.00           H  
HETATM   97  H58 UNL     1      10.261   2.165  -2.120  1.00  0.00           H  
HETATM   98  H59 UNL     1      11.567   1.825  -0.989  1.00  0.00           H  
HETATM   99  H60 UNL     1       9.430  -0.160  -1.843  1.00  0.00           H  
HETATM  100  H61 UNL     1      11.126  -0.081  -2.314  1.00  0.00           H  
HETATM  101  H62 UNL     1       9.101  -1.923   0.111  1.00  0.00           H  
HETATM  102  H63 UNL     1      11.064  -3.271   1.343  1.00  0.00           H  
HETATM  103  H64 UNL     1       9.979  -2.749   3.323  1.00  0.00           H  
HETATM  104  H65 UNL     1      10.854  -1.132   3.326  1.00  0.00           H  
HETATM  105  H66 UNL     1       9.240  -1.334   2.569  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3   43   44
CONECT    3    4   45   46
CONECT    4    5   47   48
CONECT    5    6   49   50
CONECT    6    7   51   52
CONECT    7    8   53   54
CONECT    8    9   55   56
CONECT    9   10   57   58
CONECT   10   11   59   60
CONECT   11   12   61   62
CONECT   12   13   63   64
CONECT   13   14   65   66
CONECT   14   15   67   68
CONECT   15   16   69   70
CONECT   16   17   71   72
CONECT   17   18   19   73
CONECT   18   74
CONECT   19   20   21   75
CONECT   20   76
CONECT   21   22   77   78
CONECT   22   23   79   80
CONECT   23   24   81   82
CONECT   24   25   83   84
CONECT   25   26   85   86
CONECT   26   27   87   88
CONECT   27   28   89   90
CONECT   28   29   91   92
CONECT   29   30   93   94
CONECT   30   31   95   96
CONECT   31   32   97   98
CONECT   32   33   99  100
CONECT   33   34   34   38
CONECT   34   35  101
CONECT   35   36   37  102
CONECT   36  103  104  105
CONECT   37   38
CONECT   38   39   39
END

HMDB0033607
     RDKit          3D
Artemoin D
105105  0  0  0  0  0  0  0  0999 V2000
  -11.4887    1.5929   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5672    1.5370    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0143    0.9326    1.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5331   -0.4553    1.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9695   -1.1127    2.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5216   -2.4879    2.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4696   -2.5273    1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2081   -1.7962    1.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2349   -1.8843    0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8933   -1.2041    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0341    0.2295    1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8489    0.9978    1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785    1.1649    0.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8679   -0.0286    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    0.3031   -0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728    1.3321   -0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    1.6951   -0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1356    2.1952   -2.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4588    0.7741   -1.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154    0.1976    0.0174 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3281   -0.2717   -2.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5976   -1.1064   -2.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800   -0.2648   -2.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0420   -1.1100   -2.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1797   -0.2305   -3.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4891    0.8740   -2.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8832    0.2465   -0.8351 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2184    1.2093    0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2375    2.2267    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6565    2.1326   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4390    1.5974   -1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3805    0.1582   -1.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7851   -0.6883   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1186   -1.6057    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9241   -2.1696    1.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2201   -1.8203    2.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1367   -1.4710    1.3628 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1012   -0.5582    0.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0117    0.2428   -0.0433 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4647    0.7125   -1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5128    1.6768   -0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6226    2.5196   -1.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9818    2.5171    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -12.8649    0.8588    2.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3760   -1.0604    1.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.1522   -3.5848    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9147   -2.2696    2.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5208   -0.7240    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0010   -2.9448    0.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6939   -1.4494   -0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4048   -1.2963   -0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3094    1.4575   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6171    0.7044    0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5093   -0.9782   -2.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1997    0.1896   -3.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7945   -1.4981   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623   -1.9917   -2.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6050    0.2535   -3.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771    0.4297   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1807   -1.6274   -1.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8924   -1.8653   -3.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1332   -0.8301   -3.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9569    0.1864   -4.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3188    1.4654   -2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6371    1.5832   -2.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8678   -0.2189   -0.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4839   -0.6346   -0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2376    1.6643    0.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5025    0.5575    1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8935    3.0573   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0746    2.8912    1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0595    3.2366    0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1312    1.7229    0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2608    2.1650   -2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5671    1.8254   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4303   -0.1599   -1.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1260   -0.0808   -2.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1013   -1.9226    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0642   -3.2709    1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9789   -2.7488    3.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8537   -1.1319    3.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2404   -1.3341    2.5691 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

Value	Source
3-(13,14-Dihydroxytriacontyl)-5-methyl-2(5H)-furanone	HMDB

Chemical Formula

C₃₅H₆₆O₄

Average Molecular Weight

550.8961

Monoisotopic Molecular Weight

550.4961106

IUPAC Name

3-(13,14-dihydroxytriacontyl)-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

3-(13,14-dihydroxytriacontyl)-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O

InChI Identifier

InChI=1S/C35H66O4/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-25-28-33(36)34(37)29-26-23-20-17-14-13-15-18-21-24-27-32-30-31(2)39-35(32)38/h30-31,33-34,36-37H,3-29H2,1-2H3

InChI Key

CAGLXILDKKCMCR-UHFFFAOYSA-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
Long chain fatty alcohol
2-furanone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
1,2-diol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0033607)
Cell membrane (HMDB: HMDB0033607)

Biofluid or Excreta

Urine (HMDB: HMDB0033607)

Cellular substructure

Extracellular (HMDB: HMDB0033607)
Membrane (HMDB: HMDB0033607)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033607)

Source

Endogenous

Endogenous (HMDB: HMDB0033607)

Plant

Plant (HMDB: HMDB0033607)

Animal

Animal (HMDB: HMDB0033607)

Exogenous

Food

Food (HMDB: HMDB0033607)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033607)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033607)

Cellular process

Cell signaling (HMDB: HMDB0033607)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033607)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033607)

Nutrient

Nutrient (HMDB: HMDB0033607)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033607)

Emulsifier (HMDB: HMDB0033607)

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	4.9e-05 g/L	ALOGPS
logP	9.85	ALOGPS
logP	11.78	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	166.48 m³·mol⁻¹	ChemAxon
Polarizability	74.23 Å³	ChemAxon
Number of Rings	1	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]+	244.382	31661259
DarkChem	[M-H]-	243.504	31661259
DeepCCS	[M+H]+	248.827	30932474
DeepCCS	[M-H]-	245.581	30932474
DeepCCS	[M-2H]-	281.353	30932474
DeepCCS	[M+Na]+	257.643	30932474
AllCCS	[M+H]+	260.4	32859911
AllCCS	[M+H-H2O]+	259.2	32859911
AllCCS	[M+NH4]+	261.5	32859911
AllCCS	[M+Na]+	261.8	32859911
AllCCS	[M-H]-	234.0	32859911
AllCCS	[M+Na-2H]-	238.4	32859911
AllCCS	[M+HCOO]-	243.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artemoin D	CCCCCCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O	4481.0	Standard polar	33892256
Artemoin D	CCCCCCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O	3963.5	Standard non polar	33892256
Artemoin D	CCCCCCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O	4301.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artemoin D,1TMS,isomer #1	CCCCCCCCCCCCCCCCC(O[Si](C)(C)C)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O	4187.6	Semi standard non polar	33892256
Artemoin D,1TMS,isomer #2	CCCCCCCCCCCCCCCCC(O)C(CCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C	4187.4	Semi standard non polar	33892256
Artemoin D,2TMS,isomer #1	CCCCCCCCCCCCCCCCC(O[Si](C)(C)C)C(CCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C	4118.8	Semi standard non polar	33892256
Artemoin D,1TBDMS,isomer #1	CCCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O	4445.1	Semi standard non polar	33892256
Artemoin D,1TBDMS,isomer #2	CCCCCCCCCCCCCCCCC(O)C(CCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C(C)(C)C	4444.9	Semi standard non polar	33892256
Artemoin D,2TBDMS,isomer #1	CCCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(CCCCCCCCCCCCC1=CC(C)OC1=O)O[Si](C)(C)C(C)(C)C	4626.5	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 - Artemoin D GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pc1-2190110000-301424c6108cda5dd00a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artemoin D GC-MS (2 TMS) - 70eV, Positive	splash10-004i-8706809000-b97157c9ce2088a19f13	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artemoin D GC-MS ("Artemoin D,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artemoin D GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artemoin D GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artemoin D GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artemoin D GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artemoin D GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	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 - Artemoin D 10V, Positive-QTOF	splash10-0udi-0010190000-94dccb7dae160e54d615	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 20V, Positive-QTOF	splash10-016r-2490130000-39adfbcfaa9e52a6b6f6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 40V, Positive-QTOF	splash10-004i-3960200000-966316d44cff4ed699fa	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 10V, Negative-QTOF	splash10-0002-0010090000-655a18c3d9e8bf700bd8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 20V, Negative-QTOF	splash10-052b-1090060000-dc6a25f5f71586fe4352	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 40V, Negative-QTOF	splash10-0kcr-2090000000-6ac706b6299a162fc9a8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 10V, Positive-QTOF	splash10-0159-1020190000-218716ec151cd2ba60e1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 20V, Positive-QTOF	splash10-0f89-2000190000-8206749ededec3b55b1c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 40V, Positive-QTOF	splash10-052f-9001000000-02b7c1be001b562672e5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 10V, Negative-QTOF	splash10-0002-0013090000-728d172cb2bfe65016f3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 20V, Negative-QTOF	splash10-0002-2062090000-2be9f3ebd341812d05a9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artemoin D 40V, Negative-QTOF	splash10-054n-3291010000-8acac13b2e68f1b4417a	2021-09-25	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

FDB011695

KNApSAcK ID

C00038515

Chemspider ID

35013641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751462

PDB ID

Not Available

ChEBI ID

134011

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 Artemoin D (HMDB0033607)

MOL for HMDB0033607 (Artemoin D)

3D MOL for HMDB0033607 (Artemoin D)

3D SDF for HMDB0033607 (Artemoin D)

3D-SDF for HMDB0033607 (Artemoin D)

PDB for HMDB0033607 (Artemoin D)

3D PDB for HMDB0033607 (Artemoin D)

SMILES for HMDB0033607 (Artemoin D)

INCHI for HMDB0033607 (Artemoin D)

Structure for HMDB0033607 (Artemoin D)

3D Structure for HMDB0033607 (Artemoin D)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra