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Showing metabocard for Annonisin (HMDB0031394)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:51 UTC
Update Date2022-03-07 02:52:57 UTC
HMDB IDHMDB0031394
Secondary Accession Numbers
  • HMDB31394
Metabolite Identification
Common NameAnnonisin
DescriptionAnnonisin 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 Annonisin.
Structure
Data?1563862120
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031394 (Annonisin)


  Mrv0541 05061305552D          

 43 45  0  0  0  0            999 V2000
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M  END
Download

3D MOL for HMDB0031394 (Annonisin)

HMDB0031394
     RDKit          3D
Annonisin
105107  0  0  0  0  0  0  0  0999 V2000
  -12.4791   -1.4518    1.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
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 34100  1  0
 36101  1  0
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 38103  1  0
 38104  1  0
 38105  1  0
M  END
Download

3D SDF for HMDB0031394 (Annonisin)


  Mrv0541 05061305552D          

 43 45  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0031394

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCC(O)CCCC(O)CC1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H62O8/c1-3-4-5-6-7-8-9-10-17-29(38)31-19-21-33(42-31)34-22-20-32(43-34)30(39)18-12-11-14-27(36)15-13-16-28(37)24-26-23-25(2)41-35(26)40/h23,25,27-34,36-39H,3-22,24H2,1-2H3

> <INCHI_KEY>
ZZFFUICBXFIPAB-UHFFFAOYSA-N

> <FORMULA>
C35H62O8

> <MOLECULAR_WEIGHT>
610.862

> <EXACT_MASS>
610.44446896

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
74.54003873350203

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-3-(2,6,11-trihydroxy-11-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
5.16

> <JCHEM_LOGP>
6.406336076333335

> <ALOGPS_LOGS>
-5.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.379898069035093

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.851672293414829

> <JCHEM_PKA_STRONGEST_BASIC>
-1.273821527855442

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
168.86409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-3-(2,6,11-trihydroxy-11-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0031394 (Annonisin)

HMDB0031394
     RDKit          3D
Annonisin
105107  0  0  0  0  0  0  0  0999 V2000
  -12.4791   -1.4518    1.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5107    1.7048    1.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5220    2.6508    3.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0327    3.6332    3.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 40 41  2  0
 20 42  1  0
 16 43  1  0
 43 13  1  0
 42 17  1  0
 40 35  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  2 48  1  0
  3 49  1  0
  3 50  1  0
  4 51  1  0
  4 52  1  0
  5 53  1  0
  5 54  1  0
  6 55  1  0
  6 56  1  0
  7 57  1  0
  7 58  1  0
  8 59  1  0
  8 60  1  0
  9 61  1  0
  9 62  1  0
 10 63  1  0
 10 64  1  0
 11 65  1  0
 12 66  1  0
 13 67  1  0
 14 68  1  0
 14 69  1  0
 15 70  1  0
 15 71  1  0
 16 72  1  0
 17 73  1  0
 18 74  1  0
 18 75  1  0
 19 76  1  0
 19 77  1  0
 20 78  1  0
 21 79  1  0
 22 80  1  0
 23 81  1  0
 23 82  1  0
 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
 28 90  1  0
 29 91  1  0
 29 92  1  0
 30 93  1  0
 30 94  1  0
 31 95  1  0
 31 96  1  0
 32 97  1  0
 33 98  1  0
 34 99  1  0
 34100  1  0
 36101  1  0
 37102  1  0
 38103  1  0
 38104  1  0
 38105  1  0
M  END
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PDB for HMDB0031394 (Annonisin)

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     -29.081  17.044   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.969  15.756   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -27.747  16.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -26.414  17.044   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -25.080  16.274   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -23.746  17.044   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -22.412  16.274   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -21.079  17.044   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -19.745  16.274   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -18.411  17.044   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.669  15.399   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.003  14.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.665  15.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.336  14.629   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.332  14.629   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.999  14.629   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -17.078  16.274   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.337  15.399   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -14.249  14.743   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.165  16.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -12.743  14.422   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.671  17.251   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.407  14.773   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.666  14.629   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.437  15.917   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.000  15.399   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.002  15.399   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.333  15.399   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -15.744  17.044   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.671  14.629   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -14.410  16.274   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.004  15.399   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -11.973  15.756   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.441  15.917   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.161  16.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.002  16.939   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.333  16.939   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -15.744  18.584   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -6.671  13.089   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       7.017  17.961   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       9.667  17.251   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -13.003  16.900   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -9.411  14.773   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   25                                                            
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   17                                                       
CONECT   11   12   14                                                       
CONECT   12   11   18                                                       
CONECT   13   15   16                                                       
CONECT   14   11   27                                                       
CONECT   15   13   27                                                       
CONECT   16   13   28                                                       
CONECT   17   10   29                                                       
CONECT   18   12   30                                                       
CONECT   19   21   31                                                       
CONECT   20   22   32                                                       
CONECT   21   19   33                                                       
CONECT   22   20   34                                                       
CONECT   23   25   26                                                       
CONECT   24   26   28                                                       
CONECT   25    2   23   41                                                  
CONECT   26   23   24   35                                                  
CONECT   27   14   15   36                                                  
CONECT   28   16   24   37                                                  
CONECT   29   17   31   38                                                  
CONECT   30   18   32   39                                                  
CONECT   31   19   29   42                                                  
CONECT   32   20   30   43                                                  
CONECT   33   21   34   42                                                  
CONECT   34   22   33   43                                                  
CONECT   35   26   40   41                                                  
CONECT   36   27                                                            
CONECT   37   28                                                            
CONECT   38   29                                                            
CONECT   39   30                                                            
CONECT   40   35                                                            
CONECT   41   25   35                                                       
CONECT   42   31   33                                                       
CONECT   43   32   34                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END
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3D PDB for HMDB0031394 (Annonisin)

COMPND    HMDB0031394
HETATM    1  C1  UNL     1     -12.479  -1.452   1.136  1.00  0.00           C  
HETATM    2  C2  UNL     1     -12.148  -1.386   2.600  1.00  0.00           C  
HETATM    3  C3  UNL     1     -10.727  -1.674   2.877  1.00  0.00           C  
HETATM    4  C4  UNL     1      -9.677  -0.773   2.382  1.00  0.00           C  
HETATM    5  C5  UNL     1      -9.536  -0.528   0.936  1.00  0.00           C  
HETATM    6  C6  UNL     1      -8.356   0.389   0.613  1.00  0.00           C  
HETATM    7  C7  UNL     1      -8.511   1.705   1.272  1.00  0.00           C  
HETATM    8  C8  UNL     1      -7.378   2.670   0.938  1.00  0.00           C  
HETATM    9  C9  UNL     1      -7.292   2.978  -0.502  1.00  0.00           C  
HETATM   10  C10 UNL     1      -6.188   3.895  -0.839  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.798   3.459  -0.565  1.00  0.00           C  
HETATM   12  O1  UNL     1      -4.465   3.180   0.734  1.00  0.00           O  
HETATM   13  C12 UNL     1      -4.335   2.339  -1.474  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.764   0.969  -0.987  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.522   0.095  -1.157  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.599   1.030  -1.848  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.180   0.680  -1.687  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.647   0.671  -0.280  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.638  -0.132  -0.487  1.00  0.00           C  
HETATM   20  C19 UNL     1       0.495  -0.767  -1.827  1.00  0.00           C  
HETATM   21  C20 UNL     1       0.781  -2.220  -1.839  1.00  0.00           C  
HETATM   22  O2  UNL     1       0.545  -2.702  -3.153  1.00  0.00           O  
HETATM   23  C21 UNL     1       2.017  -2.789  -1.340  1.00  0.00           C  
HETATM   24  C22 UNL     1       3.347  -2.473  -1.915  1.00  0.00           C  
HETATM   25  C23 UNL     1       3.774  -1.070  -1.802  1.00  0.00           C  
HETATM   26  C24 UNL     1       5.121  -0.735  -2.379  1.00  0.00           C  
HETATM   27  C25 UNL     1       6.302  -1.406  -1.797  1.00  0.00           C  
HETATM   28  O3  UNL     1       6.266  -2.781  -1.911  1.00  0.00           O  
HETATM   29  C26 UNL     1       6.532  -0.943  -0.370  1.00  0.00           C  
HETATM   30  C27 UNL     1       7.720  -1.582   0.282  1.00  0.00           C  
HETATM   31  C28 UNL     1       8.971  -1.279  -0.501  1.00  0.00           C  
HETATM   32  C29 UNL     1      10.153  -1.855   0.161  1.00  0.00           C  
HETATM   33  O4  UNL     1       9.953  -3.258   0.230  1.00  0.00           O  
HETATM   34  C30 UNL     1      10.454  -1.363   1.523  1.00  0.00           C  
HETATM   35  C31 UNL     1      10.726   0.085   1.593  1.00  0.00           C  
HETATM   36  C32 UNL     1      11.947   0.545   1.925  1.00  0.00           C  
HETATM   37  C33 UNL     1      11.954   2.018   1.918  1.00  0.00           C  
HETATM   38  C34 UNL     1      12.433   2.578   3.229  1.00  0.00           C  
HETATM   39  O5  UNL     1      10.621   2.379   1.734  1.00  0.00           O  
HETATM   40  C35 UNL     1       9.890   1.246   1.476  1.00  0.00           C  
HETATM   41  O6  UNL     1       8.656   1.314   1.188  1.00  0.00           O  
HETATM   42  O7  UNL     1      -0.901  -0.631  -2.129  1.00  0.00           O  
HETATM   43  O8  UNL     1      -2.915   2.312  -1.377  1.00  0.00           O  
HETATM   44  H1  UNL     1     -12.697  -0.455   0.712  1.00  0.00           H  
HETATM   45  H2  UNL     1     -11.715  -1.975   0.548  1.00  0.00           H  
HETATM   46  H3  UNL     1     -13.408  -2.107   0.988  1.00  0.00           H  
HETATM   47  H4  UNL     1     -12.831  -2.124   3.128  1.00  0.00           H  
HETATM   48  H5  UNL     1     -12.480  -0.407   3.035  1.00  0.00           H  
HETATM   49  H6  UNL     1     -10.477  -2.761   2.625  1.00  0.00           H  
HETATM   50  H7  UNL     1     -10.626  -1.692   4.014  1.00  0.00           H  
HETATM   51  H8  UNL     1      -9.756   0.226   2.902  1.00  0.00           H  
HETATM   52  H9  UNL     1      -8.691  -1.183   2.749  1.00  0.00           H  
HETATM   53  H10 UNL     1     -10.434  -0.020   0.476  1.00  0.00           H  
HETATM   54  H11 UNL     1      -9.411  -1.479   0.341  1.00  0.00           H  
HETATM   55  H12 UNL     1      -8.112   0.388  -0.443  1.00  0.00           H  
HETATM   56  H13 UNL     1      -7.472  -0.119   1.112  1.00  0.00           H  
HETATM   57  H14 UNL     1      -8.497   1.648   2.386  1.00  0.00           H  
HETATM   58  H15 UNL     1      -9.463   2.200   0.993  1.00  0.00           H  
HETATM   59  H16 UNL     1      -6.471   2.300   1.437  1.00  0.00           H  
HETATM   60  H17 UNL     1      -7.642   3.625   1.486  1.00  0.00           H  
HETATM   61  H18 UNL     1      -8.252   3.528  -0.766  1.00  0.00           H  
HETATM   62  H19 UNL     1      -7.331   2.087  -1.169  1.00  0.00           H  
HETATM   63  H20 UNL     1      -6.283   4.291  -1.896  1.00  0.00           H  
HETATM   64  H21 UNL     1      -6.352   4.836  -0.226  1.00  0.00           H  
HETATM   65  H22 UNL     1      -4.149   4.361  -0.841  1.00  0.00           H  
HETATM   66  H23 UNL     1      -3.861   3.861   1.160  1.00  0.00           H  
HETATM   67  H24 UNL     1      -4.564   2.524  -2.529  1.00  0.00           H  
HETATM   68  H25 UNL     1      -5.567   0.511  -1.557  1.00  0.00           H  
HETATM   69  H26 UNL     1      -4.969   1.069   0.091  1.00  0.00           H  
HETATM   70  H27 UNL     1      -3.195  -0.282  -0.189  1.00  0.00           H  
HETATM   71  H28 UNL     1      -3.744  -0.805  -1.787  1.00  0.00           H  
HETATM   72  H29 UNL     1      -2.838   1.005  -2.966  1.00  0.00           H  
HETATM   73  H30 UNL     1      -0.499   1.377  -2.271  1.00  0.00           H  
HETATM   74  H31 UNL     1      -1.339   0.161   0.409  1.00  0.00           H  
HETATM   75  H32 UNL     1      -0.418   1.692   0.108  1.00  0.00           H  
HETATM   76  H33 UNL     1       1.540   0.500  -0.477  1.00  0.00           H  
HETATM   77  H34 UNL     1       0.707  -0.894   0.325  1.00  0.00           H  
HETATM   78  H35 UNL     1       0.977  -0.238  -2.659  1.00  0.00           H  
HETATM   79  H36 UNL     1      -0.087  -2.726  -1.233  1.00  0.00           H  
HETATM   80  H37 UNL     1       1.003  -2.128  -3.820  1.00  0.00           H  
HETATM   81  H38 UNL     1       2.069  -2.706  -0.181  1.00  0.00           H  
HETATM   82  H39 UNL     1       1.901  -3.944  -1.422  1.00  0.00           H  
HETATM   83  H40 UNL     1       4.136  -3.143  -1.433  1.00  0.00           H  
HETATM   84  H41 UNL     1       3.338  -2.828  -2.987  1.00  0.00           H  
HETATM   85  H42 UNL     1       3.813  -0.770  -0.718  1.00  0.00           H  
HETATM   86  H43 UNL     1       3.056  -0.396  -2.315  1.00  0.00           H  
HETATM   87  H44 UNL     1       5.144  -0.885  -3.483  1.00  0.00           H  
HETATM   88  H45 UNL     1       5.252   0.378  -2.211  1.00  0.00           H  
HETATM   89  H46 UNL     1       7.192  -1.081  -2.401  1.00  0.00           H  
HETATM   90  H47 UNL     1       6.567  -3.020  -2.834  1.00  0.00           H  
HETATM   91  H48 UNL     1       6.688   0.144  -0.368  1.00  0.00           H  
HETATM   92  H49 UNL     1       5.643  -1.218   0.254  1.00  0.00           H  
HETATM   93  H50 UNL     1       7.749  -1.229   1.326  1.00  0.00           H  
HETATM   94  H51 UNL     1       7.519  -2.685   0.288  1.00  0.00           H  
HETATM   95  H52 UNL     1       9.004  -0.225  -0.782  1.00  0.00           H  
HETATM   96  H53 UNL     1       8.864  -1.804  -1.539  1.00  0.00           H  
HETATM   97  H54 UNL     1      11.051  -1.665  -0.505  1.00  0.00           H  
HETATM   98  H55 UNL     1       9.688  -3.570  -0.687  1.00  0.00           H  
HETATM   99  H56 UNL     1       9.530  -1.574   2.160  1.00  0.00           H  
HETATM  100  H57 UNL     1      11.310  -1.929   1.989  1.00  0.00           H  
HETATM  101  H58 UNL     1      12.801  -0.053   2.163  1.00  0.00           H  
HETATM  102  H59 UNL     1      12.609   2.402   1.078  1.00  0.00           H  
HETATM  103  H60 UNL     1      12.045   1.984   4.061  1.00  0.00           H  
HETATM  104  H61 UNL     1      13.522   2.651   3.234  1.00  0.00           H  
HETATM  105  H62 UNL     1      12.033   3.633   3.272  1.00  0.00           H  
CONECT    1    2   44   45   46
CONECT    2    3   47   48
CONECT    3    4   49   50
CONECT    4    5   51   52
CONECT    5    6   53   54
CONECT    6    7   55   56
CONECT    7    8   57   58
CONECT    8    9   59   60
CONECT    9   10   61   62
CONECT   10   11   63   64
CONECT   11   12   13   65
CONECT   12   66
CONECT   13   14   43   67
CONECT   14   15   68   69
CONECT   15   16   70   71
CONECT   16   17   43   72
CONECT   17   18   42   73
CONECT   18   19   74   75
CONECT   19   20   76   77
CONECT   20   21   42   78
CONECT   21   22   23   79
CONECT   22   80
CONECT   23   24   81   82
CONECT   24   25   83   84
CONECT   25   26   85   86
CONECT   26   27   87   88
CONECT   27   28   29   89
CONECT   28   90
CONECT   29   30   91   92
CONECT   30   31   93   94
CONECT   31   32   95   96
CONECT   32   33   34   97
CONECT   33   98
CONECT   34   35   99  100
CONECT   35   36   36   40
CONECT   36   37  101
CONECT   37   38   39  102
CONECT   38  103  104  105
CONECT   39   40
CONECT   40   41   41
END
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SMILES for HMDB0031394 (Annonisin)

CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCC(O)CCCC(O)CC1=CC(C)OC1=O
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INCHI for HMDB0031394 (Annonisin)

InChI=1S/C35H62O8/c1-3-4-5-6-7-8-9-10-17-29(38)31-19-21-33(42-31)34-22-20-32(43-34)30(39)18-12-11-14-27(36)15-13-16-28(37)24-26-23-25(2)41-35(26)40/h23,25,27-34,36-39H,3-22,24H2,1-2H3
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SynonymsNot Available
Chemical FormulaC35H62O8
Average Molecular Weight610.862
Monoisotopic Molecular Weight610.44446896
IUPAC Name5-methyl-3-(2,6,11-trihydroxy-11-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-2,5-dihydrofuran-2-one
Traditional Name5-methyl-3-(2,6,11-trihydroxy-11-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5H-furan-2-one
CAS Registry Number194413-43-9
SMILES
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCC(O)CCCC(O)CC1=CC(C)OC1=O
InChI Identifier
InChI=1S/C35H62O8/c1-3-4-5-6-7-8-9-10-17-29(38)31-19-21-33(42-31)34-22-20-32(43-34)30(39)18-12-11-14-27(36)15-13-16-28(37)24-26-23-25(2)41-35(26)40/h23,25,27-34,36-39H,3-22,24H2,1-2H3
InChI KeyZZFFUICBXFIPAB-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentAnnonaceous acetogenins
Alternative Parents
Substituents
  • Annonaceae acetogenin skeleton
  • Long chain fatty alcohol
  • 2-furanone
  • Dihydrofuran
  • Tetrahydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Polyol
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • 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 roleIndustrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0012 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0028 g/LALOGPS
logP5.16ALOGPS
logP6.41ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)13.85ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity168.86 m³·mol⁻¹ChemAxon
Polarizability74.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+249.48931661259
DarkChem[M-H]-240.87131661259
DeepCCS[M+H]+256.55230932474
DeepCCS[M-H]-254.15630932474
DeepCCS[M-2H]-287.03930932474
DeepCCS[M+Na]+262.58930932474
AllCCS[M+H]+270.732859911
AllCCS[M+H-H2O]+269.632859911
AllCCS[M+NH4]+271.732859911
AllCCS[M+Na]+272.032859911
AllCCS[M-H]-239.332859911
AllCCS[M+Na-2H]-243.932859911
AllCCS[M+HCOO]-249.132859911

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, 2022.7.94 minutes32390414
Predicted by Siyang on May 30, 202219.9616 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.88 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid84.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid4359.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid192.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid277.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid173.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid690.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid1102.8 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 Acid774.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)259.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1986.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid775.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid2387.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid571.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid542.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate249.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA258.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water8.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AnnonisinCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCC(O)CCCC(O)CC1=CC(C)OC1=O4649.9Standard polar33892256
AnnonisinCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCC(O)CCCC(O)CC1=CC(C)OC1=O4009.2Standard non polar33892256
AnnonisinCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCC(O)CCCC(O)CC1=CC(C)OC1=O4597.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Annonisin,1TMS,isomer #1CCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(O)CCCCC(O)CCCC(O)CC3=CC(C)OC3=O)O2)O14777.7Semi standard non polar33892256
Annonisin,1TMS,isomer #2CCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCC(O)CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O14773.5Semi standard non polar33892256
Annonisin,1TMS,isomer #3CCCCCCCCCCC(O)C1CCC(C2CCC(C(O)CCCCC(CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O14781.3Semi standard non polar33892256
Annonisin,1TMS,isomer #4CCCCCCCCCCC(O)C1CCC(C2CCC(C(O)CCCCC(O)CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O14757.7Semi standard non polar33892256
Annonisin,2TMS,isomer #1CCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(CCCCC(O)CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O14727.7Semi standard non polar33892256
Annonisin,2TMS,isomer #2CCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(O)CCCCC(CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O14734.5Semi standard non polar33892256
Annonisin,2TMS,isomer #3CCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(O)CCCCC(O)CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C)O2)O14716.0Semi standard non polar33892256
Annonisin,2TMS,isomer #4CCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCC(CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C)O[Si](C)(C)C)O2)O14732.5Semi standard non polar33892256
Annonisin,2TMS,isomer #5CCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCC(O)CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C)O[Si](C)(C)C)O2)O14711.3Semi standard non polar33892256
Annonisin,2TMS,isomer #6CCCCCCCCCCC(O)C1CCC(C2CCC(C(O)CCCCC(CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C)O[Si](C)(C)C)O2)O14706.4Semi standard non polar33892256
Annonisin,3TMS,isomer #1CCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(CCCCC(CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C)O[Si](C)(C)C)O2)O14665.3Semi standard non polar33892256
Annonisin,3TMS,isomer #2CCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(CCCCC(O)CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C)O[Si](C)(C)C)O2)O14644.0Semi standard non polar33892256
Annonisin,3TMS,isomer #3CCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(O)CCCCC(CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C)O[Si](C)(C)C)O2)O14635.6Semi standard non polar33892256
Annonisin,3TMS,isomer #4CCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCC(CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O2)O14633.4Semi standard non polar33892256
Annonisin,4TMS,isomer #1CCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C2CCC(C(CCCCC(CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O2)O14556.9Semi standard non polar33892256
Annonisin,1TBDMS,isomer #1CCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(O)CCCCC(O)CCCC(O)CC3=CC(C)OC3=O)O2)O14992.2Semi standard non polar33892256
Annonisin,1TBDMS,isomer #2CCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCC(O)CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O14990.1Semi standard non polar33892256
Annonisin,1TBDMS,isomer #3CCCCCCCCCCC(O)C1CCC(C2CCC(C(O)CCCCC(CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O14998.5Semi standard non polar33892256
Annonisin,1TBDMS,isomer #4CCCCCCCCCCC(O)C1CCC(C2CCC(C(O)CCCCC(O)CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O14985.3Semi standard non polar33892256
Annonisin,2TBDMS,isomer #1CCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(CCCCC(O)CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O15164.4Semi standard non polar33892256
Annonisin,2TBDMS,isomer #2CCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(O)CCCCC(CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O15161.2Semi standard non polar33892256
Annonisin,2TBDMS,isomer #3CCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C2CCC(C(O)CCCCC(O)CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O2)O15155.6Semi standard non polar33892256
Annonisin,2TBDMS,isomer #4CCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCC(CCCC(O)CC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)O15158.8Semi standard non polar33892256
Annonisin,2TBDMS,isomer #5CCCCCCCCCCC(O)C1CCC(C2CCC(C(CCCCC(O)CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)O15153.0Semi standard non polar33892256
Annonisin,2TBDMS,isomer #6CCCCCCCCCCC(O)C1CCC(C2CCC(C(O)CCCCC(CCCC(CC3=CC(C)OC3=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O2)O15154.6Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB003463
KNApSAcK IDC00044086
Chemspider ID35013362
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751165
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1826151
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.