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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:54:07 UTC

Update Date

2022-03-07 02:53:37 UTC

HMDB ID

HMDB0033165

Secondary Accession Numbers

HMDB33165

Metabolite Identification

Common Name

4-Deoxyannoreticuin

Description

4-Deoxyannoreticuin 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 4-Deoxyannoreticuin.

Structure

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


  Mrv0541 02241209392D          

 41 42  0  0  0  0            999 V2000
   -3.0353    1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064    1.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977    1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0117    1.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012    1.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2031    1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117    1.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4977    1.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3064    1.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7107    1.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5213    1.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1405   -0.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9773   -0.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1686    0.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6011   -0.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924   -0.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449   -0.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7688   -0.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1405   -1.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9256    0.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0744    1.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 40  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 39  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
M  END

HMDB0033165
     RDKit          3D
4-Deoxyannoreticuin
105106  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 02241209392D          

 41 42  0  0  0  0            999 V2000
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 40  1  0  0  0  0
  3  4  2  0  0  0  0
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  4 39  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0033165

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCC(O)CCCCCCC1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H64O6/c1-3-4-5-6-7-8-9-10-11-18-23-31(37)33-25-26-34(41-33)32(38)24-19-14-17-22-30(36)21-16-13-12-15-20-29-27-28(2)40-35(29)39/h27-28,30-34,36-38H,3-26H2,1-2H3

> <INCHI_KEY>
JHKNWORCLXKZFL-UHFFFAOYSA-N

> <FORMULA>
C35H64O6

> <MOLECULAR_WEIGHT>
580.8791

> <EXACT_MASS>
580.47028978

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
74.39489252524834

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{7,13-dihydroxy-13-[5-(1-hydroxytridecyl)oxolan-2-yl]tridecyl}-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
7.55

> <JCHEM_LOGP>
9.092973164999997

> <ALOGPS_LOGS>
-6.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.43247480361821

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.873469719970899

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2743089042992626

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
167.6737

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.39e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{7,13-dihydroxy-13-[5-(1-hydroxytridecyl)oxolan-2-yl]tridecyl}-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033165
     RDKit          3D
4-Deoxyannoreticuin
105106  0  0  0  0  0  0  0  0999 V2000
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  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  0
  2 46  1  0
  3 47  1  0
  3 48  1  0
  4 49  1  0
  4 50  1  0
  5 51  1  0
  5 52  1  0
  6 53  1  0
  6 54  1  0
  7 55  1  0
  7 56  1  0
  8 57  1  0
  8 58  1  0
  9 59  1  0
  9 60  1  0
 10 61  1  0
 10 62  1  0
 11 63  1  0
 11 64  1  0
 12 65  1  0
 12 66  1  0
 13 67  1  0
 14 68  1  0
 15 69  1  0
 16 70  1  0
 16 71  1  0
 17 72  1  0
 17 73  1  0
 18 74  1  0
 19 75  1  0
 20 76  1  0
 21 77  1  0
 21 78  1  0
 22 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
 27 88  1  0
 28 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
 32 98  1  0
 33 99  1  0
 33100  1  0
 35101  1  0
 36102  1  0
 37103  1  0
 37104  1  0
 37105  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.666   2.114   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.305   2.719   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.796   2.114   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.889   3.322   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.376   3.474   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.379   2.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.889   1.965   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.796   3.322   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.305   3.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.060   1.965   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.573   1.965   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.596  -1.664   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.291  -0.154   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.781   0.299   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.722  -0.604   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.212  -0.154   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.004  -1.210   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.643  -0.604   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.435  -1.664   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.074  -1.057   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.286  -1.664   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.643  -0.756   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.004  -1.511   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.703  -3.024   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.342  -3.779   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.421  -3.474   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.911  -3.928   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.911  -5.441   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.421  -6.043   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.328  -4.686   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.841  -4.686   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.596  -6.043   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.596  -3.325   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.841  -2.117   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.596  -0.756   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.841   0.601   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.328   0.601   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.190   6.043   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.796   4.530   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.305   4.229   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       7.606   3.715   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   39                                                  
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   37   41                                                  
CONECT   12   13                                                            
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24                                                            
CONECT   26   27   30                                                       
CONECT   27   24   26   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   26   29   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   11   36                                                       
CONECT   38   39                                                            
CONECT   39    4   38   40                                                  
CONECT   40    2   39                                                       
CONECT   41   11                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   84    0
END

COMPND    HMDB0033165
HETATM    1  C1  UNL     1     -12.944   3.130  -1.160  1.00  0.00           C  
HETATM    2  C2  UNL     1     -12.794   2.356   0.118  1.00  0.00           C  
HETATM    3  C3  UNL     1     -11.936   1.154  -0.114  1.00  0.00           C  
HETATM    4  C4  UNL     1     -10.553   1.590  -0.600  1.00  0.00           C  
HETATM    5  C5  UNL     1      -9.769   0.313  -0.800  1.00  0.00           C  
HETATM    6  C6  UNL     1      -8.372   0.604  -1.278  1.00  0.00           C  
HETATM    7  C7  UNL     1      -7.586  -0.682  -1.475  1.00  0.00           C  
HETATM    8  C8  UNL     1      -7.489  -1.465  -0.189  1.00  0.00           C  
HETATM    9  C9  UNL     1      -6.822  -0.724   0.911  1.00  0.00           C  
HETATM   10  C10 UNL     1      -5.408  -0.305   0.656  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.497  -1.477   0.397  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.071  -1.099   0.155  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.854  -0.202  -1.037  1.00  0.00           C  
HETATM   14  O1  UNL     1      -3.305  -0.868  -2.199  1.00  0.00           O  
HETATM   15  C14 UNL     1      -1.396   0.097  -1.236  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.782   0.966  -0.199  1.00  0.00           C  
HETATM   17  C16 UNL     1       0.614   0.343  -0.051  1.00  0.00           C  
HETATM   18  C17 UNL     1       0.251  -1.100  -0.333  1.00  0.00           C  
HETATM   19  C18 UNL     1       1.398  -1.968  -0.694  1.00  0.00           C  
HETATM   20  O2  UNL     1       0.960  -3.235  -0.977  1.00  0.00           O  
HETATM   21  C19 UNL     1       2.473  -1.974   0.429  1.00  0.00           C  
HETATM   22  C20 UNL     1       1.911  -2.462   1.686  1.00  0.00           C  
HETATM   23  C21 UNL     1       2.793  -2.533   2.863  1.00  0.00           C  
HETATM   24  C22 UNL     1       3.942  -3.410   2.924  1.00  0.00           C  
HETATM   25  C23 UNL     1       5.132  -3.252   2.098  1.00  0.00           C  
HETATM   26  C24 UNL     1       5.879  -1.925   2.371  1.00  0.00           C  
HETATM   27  O3  UNL     1       5.063  -0.856   2.086  1.00  0.00           O  
HETATM   28  C25 UNL     1       7.111  -1.979   1.538  1.00  0.00           C  
HETATM   29  C26 UNL     1       8.004  -0.816   1.701  1.00  0.00           C  
HETATM   30  C27 UNL     1       7.400   0.485   1.352  1.00  0.00           C  
HETATM   31  C28 UNL     1       8.503   1.553   1.520  1.00  0.00           C  
HETATM   32  C29 UNL     1       7.934   2.888   1.180  1.00  0.00           C  
HETATM   33  C30 UNL     1       7.440   3.025  -0.207  1.00  0.00           C  
HETATM   34  C31 UNL     1       8.465   2.933  -1.272  1.00  0.00           C  
HETATM   35  C32 UNL     1       9.771   2.809  -1.207  1.00  0.00           C  
HETATM   36  C33 UNL     1      10.399   2.750  -2.565  1.00  0.00           C  
HETATM   37  C34 UNL     1      11.185   1.471  -2.737  1.00  0.00           C  
HETATM   38  O4  UNL     1       9.326   2.870  -3.428  1.00  0.00           O  
HETATM   39  C35 UNL     1       8.151   2.975  -2.725  1.00  0.00           C  
HETATM   40  O5  UNL     1       6.982   3.089  -3.171  1.00  0.00           O  
HETATM   41  O6  UNL     1      -0.642  -1.054  -1.399  1.00  0.00           O  
HETATM   42  H1  UNL     1     -13.902   3.704  -1.194  1.00  0.00           H  
HETATM   43  H2  UNL     1     -12.065   3.782  -1.275  1.00  0.00           H  
HETATM   44  H3  UNL     1     -13.032   2.384  -1.999  1.00  0.00           H  
HETATM   45  H4  UNL     1     -13.781   2.001   0.515  1.00  0.00           H  
HETATM   46  H5  UNL     1     -12.316   3.001   0.895  1.00  0.00           H  
HETATM   47  H6  UNL     1     -12.372   0.476  -0.860  1.00  0.00           H  
HETATM   48  H7  UNL     1     -11.771   0.600   0.848  1.00  0.00           H  
HETATM   49  H8  UNL     1     -10.601   2.228  -1.481  1.00  0.00           H  
HETATM   50  H9  UNL     1     -10.091   2.148   0.235  1.00  0.00           H  
HETATM   51  H10 UNL     1     -10.279  -0.281  -1.581  1.00  0.00           H  
HETATM   52  H11 UNL     1      -9.776  -0.220   0.173  1.00  0.00           H  
HETATM   53  H12 UNL     1      -7.885   1.268  -0.554  1.00  0.00           H  
HETATM   54  H13 UNL     1      -8.466   1.150  -2.238  1.00  0.00           H  
HETATM   55  H14 UNL     1      -8.173  -1.295  -2.189  1.00  0.00           H  
HETATM   56  H15 UNL     1      -6.605  -0.487  -1.952  1.00  0.00           H  
HETATM   57  H16 UNL     1      -8.489  -1.795   0.095  1.00  0.00           H  
HETATM   58  H17 UNL     1      -6.901  -2.388  -0.434  1.00  0.00           H  
HETATM   59  H18 UNL     1      -7.467   0.138   1.191  1.00  0.00           H  
HETATM   60  H19 UNL     1      -6.857  -1.397   1.818  1.00  0.00           H  
HETATM   61  H20 UNL     1      -5.069   0.224   1.593  1.00  0.00           H  
HETATM   62  H21 UNL     1      -5.294   0.411  -0.157  1.00  0.00           H  
HETATM   63  H22 UNL     1      -4.500  -2.097   1.333  1.00  0.00           H  
HETATM   64  H23 UNL     1      -4.882  -2.146  -0.395  1.00  0.00           H  
HETATM   65  H24 UNL     1      -2.626  -0.707   1.069  1.00  0.00           H  
HETATM   66  H25 UNL     1      -2.541  -2.060  -0.100  1.00  0.00           H  
HETATM   67  H26 UNL     1      -3.433   0.715  -0.895  1.00  0.00           H  
HETATM   68  H27 UNL     1      -4.251  -0.649  -2.375  1.00  0.00           H  
HETATM   69  H28 UNL     1      -1.340   0.675  -2.208  1.00  0.00           H  
HETATM   70  H29 UNL     1      -1.279   0.792   0.777  1.00  0.00           H  
HETATM   71  H30 UNL     1      -0.721   2.035  -0.468  1.00  0.00           H  
HETATM   72  H31 UNL     1       1.211   0.714  -0.903  1.00  0.00           H  
HETATM   73  H32 UNL     1       1.043   0.509   0.933  1.00  0.00           H  
HETATM   74  H33 UNL     1      -0.325  -1.491   0.533  1.00  0.00           H  
HETATM   75  H34 UNL     1       1.918  -1.544  -1.573  1.00  0.00           H  
HETATM   76  H35 UNL     1      -0.003  -3.389  -0.740  1.00  0.00           H  
HETATM   77  H36 UNL     1       3.233  -2.647   0.024  1.00  0.00           H  
HETATM   78  H37 UNL     1       2.871  -0.962   0.504  1.00  0.00           H  
HETATM   79  H38 UNL     1       1.423  -3.502   1.540  1.00  0.00           H  
HETATM   80  H39 UNL     1       0.995  -1.867   2.014  1.00  0.00           H  
HETATM   81  H40 UNL     1       3.136  -1.479   3.173  1.00  0.00           H  
HETATM   82  H41 UNL     1       2.144  -2.768   3.810  1.00  0.00           H  
HETATM   83  H42 UNL     1       3.527  -4.486   2.837  1.00  0.00           H  
HETATM   84  H43 UNL     1       4.332  -3.453   4.020  1.00  0.00           H  
HETATM   85  H44 UNL     1       5.002  -3.341   1.019  1.00  0.00           H  
HETATM   86  H45 UNL     1       5.903  -4.067   2.380  1.00  0.00           H  
HETATM   87  H46 UNL     1       6.106  -1.924   3.470  1.00  0.00           H  
HETATM   88  H47 UNL     1       5.081  -0.742   1.091  1.00  0.00           H  
HETATM   89  H48 UNL     1       6.758  -2.040   0.462  1.00  0.00           H  
HETATM   90  H49 UNL     1       7.649  -2.961   1.735  1.00  0.00           H  
HETATM   91  H50 UNL     1       8.930  -0.938   1.072  1.00  0.00           H  
HETATM   92  H51 UNL     1       8.307  -0.753   2.786  1.00  0.00           H  
HETATM   93  H52 UNL     1       6.568   0.761   2.054  1.00  0.00           H  
HETATM   94  H53 UNL     1       6.993   0.472   0.341  1.00  0.00           H  
HETATM   95  H54 UNL     1       9.344   1.220   0.924  1.00  0.00           H  
HETATM   96  H55 UNL     1       8.772   1.503   2.612  1.00  0.00           H  
HETATM   97  H56 UNL     1       7.133   3.153   1.915  1.00  0.00           H  
HETATM   98  H57 UNL     1       8.757   3.641   1.404  1.00  0.00           H  
HETATM   99  H58 UNL     1       6.865   4.007  -0.313  1.00  0.00           H  
HETATM  100  H59 UNL     1       6.653   2.268  -0.438  1.00  0.00           H  
HETATM  101  H60 UNL     1      10.355   2.777  -0.274  1.00  0.00           H  
HETATM  102  H61 UNL     1      11.088   3.631  -2.630  1.00  0.00           H  
HETATM  103  H62 UNL     1      12.207   1.655  -2.297  1.00  0.00           H  
HETATM  104  H63 UNL     1      11.286   1.143  -3.774  1.00  0.00           H  
HETATM  105  H64 UNL     1      10.639   0.679  -2.173  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3   45   46
CONECT    3    4   47   48
CONECT    4    5   49   50
CONECT    5    6   51   52
CONECT    6    7   53   54
CONECT    7    8   55   56
CONECT    8    9   57   58
CONECT    9   10   59   60
CONECT   10   11   61   62
CONECT   11   12   63   64
CONECT   12   13   65   66
CONECT   13   14   15   67
CONECT   14   68
CONECT   15   16   41   69
CONECT   16   17   70   71
CONECT   17   18   72   73
CONECT   18   19   41   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   28   87
CONECT   27   88
CONECT   28   29   89   90
CONECT   29   30   91   92
CONECT   30   31   93   94
CONECT   31   32   95   96
CONECT   32   33   97   98
CONECT   33   34   99  100
CONECT   34   35   35   39
CONECT   35   36  101
CONECT   36   37   38  102
CONECT   37  103  104  105
CONECT   38   39
CONECT   39   40   40
END

HMDB0033165
     RDKit          3D
4-Deoxyannoreticuin
105106  0  0  0  0  0  0  0  0999 V2000
  -12.9435    3.1302   -1.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7935    2.3558    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9360    1.1536   -0.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5528    1.5898   -0.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7687    0.3130   -0.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3722    0.6037   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5864   -0.6817   -1.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4890   -1.4649   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8220   -0.7239    0.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4084   -0.3047    0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4973   -1.4774    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0707   -1.0989    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8537   -0.2018   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046   -0.8684   -2.1991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958    0.0971   -1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    0.9661   -0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139    0.3429   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2512   -1.1004   -0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3980   -1.9676   -0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9604   -3.2353   -0.9766 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727   -1.9744    0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -2.4621    1.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7928   -2.5327    2.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420   -3.4102    2.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1319   -3.2525    2.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8786   -1.9246    2.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0634   -0.8557    2.0863 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1111   -1.9788    1.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -0.8160    1.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3998    0.4849    1.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5032    1.5528    1.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9344    2.8883    1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4396    3.0247   -0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4651    2.9327   -1.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7705    2.8087   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3992    2.7504   -2.5651 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1845    1.4709   -2.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3262    2.8705   -3.4276 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1505    2.9752   -2.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9819    3.0894   -3.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424   -1.0542   -1.3994 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9021    3.7041   -1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0648    3.7818   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0320    2.3843   -1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7809    2.0009    0.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3161    3.0011    0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3718    0.4763   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7714    0.5995    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6008    2.2276   -1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0912    2.1481    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2788   -0.2815   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7755   -0.2199    0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8853    1.2684   -0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4657    1.1504   -2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1728   -1.2947   -2.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6053   -0.4872   -1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4894   -1.7946    0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9009   -2.3879   -0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4673    0.1376    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8570   -1.3975    1.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0691    0.2236    1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2944    0.4111   -0.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5001   -2.0971    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8823   -2.1458   -0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6261   -0.7074    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5411   -2.0601   -0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330    0.7152   -0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2507   -0.6486   -2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401    0.6747   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785    0.7923    0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7207    2.0349   -0.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111    0.7136   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431    0.5093    0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3252   -1.4906    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9183   -1.5439   -1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0027   -3.3893   -0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2330   -2.6473    0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8706   -0.9624    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225   -3.5021    1.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.8670    2.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1355   -1.4793    3.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1440   -2.7682    3.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5274   -4.4865    2.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3315   -3.4526    4.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0022   -3.3413    1.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9035   -4.0671    2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058   -1.9242    3.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0808   -0.7416    1.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7584   -2.0403    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6488   -2.9614    1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9298   -0.9381    1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3067   -0.7533    2.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5679    0.7608    2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9928    0.4717    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3442    1.2200    0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7721    1.5030    2.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325    3.1531    1.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7567    3.6410    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8652    4.0073   -0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6527    2.2675   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3549    2.7771   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0884    3.6313   -2.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2067    1.6549   -2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2856    1.1429   -3.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6388    0.6788   -2.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₅H₆₄O₆

Average Molecular Weight

580.8791

Monoisotopic Molecular Weight

580.47028978

IUPAC Name

3-{7,13-dihydroxy-13-[5-(1-hydroxytridecyl)oxolan-2-yl]tridecyl}-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

3-{7,13-dihydroxy-13-[5-(1-hydroxytridecyl)oxolan-2-yl]tridecyl}-5-methyl-5H-furan-2-one

CAS Registry Number

206192-79-2

SMILES

CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCC(O)CCCCCCC1=CC(C)OC1=O

InChI Identifier

InChI=1S/C35H64O6/c1-3-4-5-6-7-8-9-10-11-18-23-31(37)33-25-26-34(41-33)32(38)24-19-14-17-22-30(36)21-16-13-12-15-20-29-27-28(2)40-35(29)39/h27-28,30-34,36-38H,3-26H2,1-2H3

InChI Key

JHKNWORCLXKZFL-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
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0033165)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033165)

Source

Exogenous

Food

Food (HMDB: HMDB0033165)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0033165)

Endogenous

Plant

Plant (HMDB: HMDB0033165)

Animal

Animal (HMDB: HMDB0033165)

Endogenous (HMDB: HMDB0033165)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033165)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033165)

Lipid metabolism pathway (HMDB: HMDB0033165)

Cellular process

Cell signaling (HMDB: HMDB0033165)

Biochemical process

Lipid transport (HMDB: HMDB0033165)

Role

Biological role

Energy source (HMDB: HMDB0033165)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033165)

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	4.8e-06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00054 g/L	ALOGPS
logP	7.55	ALOGPS
logP	9.09	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	13.87	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	167.67 m³·mol⁻¹	ChemAxon
Polarizability	74.39 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	244.599	31661259
DarkChem	[M-H]-	240.386	31661259
DeepCCS	[M+H]+	253.429	30932474
DeepCCS	[M-H]-	251.071	30932474
DeepCCS	[M-2H]-	284.949	30932474
DeepCCS	[M+Na]+	260.178	30932474
AllCCS	[M+H]+	266.5	32859911
AllCCS	[M+H-H2O]+	265.3	32859911
AllCCS	[M+NH4]+	267.6	32859911
AllCCS	[M+Na]+	267.9	32859911
AllCCS	[M-H]-	236.4	32859911
AllCCS	[M+Na-2H]-	240.8	32859911
AllCCS	[M+HCOO]-	245.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.56 minutes	32390414
Predicted by Siyang on May 30, 2022	27.5481 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.07 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	71.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4653.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	450.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	318.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	782.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1336.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1069.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	194.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2660.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	865.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2677.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	867.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	635.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	327.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	496.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Deoxyannoreticuin	CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCC(O)CCCCCCC1=CC(C)OC1=O	4490.3	Standard polar	33892256
4-Deoxyannoreticuin	CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCC(O)CCCCCCC1=CC(C)OC1=O	4111.9	Standard non polar	33892256
4-Deoxyannoreticuin	CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCC(O)CCCCCCC1=CC(C)OC1=O	4432.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Deoxyannoreticuin,1TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCCC(O)CCCCCCC2=CC(C)OC2=O)O1	4419.1	Semi standard non polar	33892256
4-Deoxyannoreticuin,1TMS,isomer #2	CCCCCCCCCCCCC(O)C1CCC(C(CCCCCC(O)CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C)O1	4418.9	Semi standard non polar	33892256
4-Deoxyannoreticuin,1TMS,isomer #3	CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCCC(CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C)O1	4461.4	Semi standard non polar	33892256
4-Deoxyannoreticuin,2TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(CCCCCC(O)CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C)O1	4383.2	Semi standard non polar	33892256
4-Deoxyannoreticuin,2TMS,isomer #2	CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(O)CCCCCC(CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C)O1	4386.2	Semi standard non polar	33892256
4-Deoxyannoreticuin,2TMS,isomer #3	CCCCCCCCCCCCC(O)C1CCC(C(CCCCCC(CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1	4387.0	Semi standard non polar	33892256
4-Deoxyannoreticuin,3TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C1CCC(C(CCCCCC(CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C)O[Si](C)(C)C)O1	4342.4	Semi standard non polar	33892256
4-Deoxyannoreticuin,1TBDMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCCC(O)CCCCCCC2=CC(C)OC2=O)O1	4646.4	Semi standard non polar	33892256
4-Deoxyannoreticuin,1TBDMS,isomer #2	CCCCCCCCCCCCC(O)C1CCC(C(CCCCCC(O)CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	4646.1	Semi standard non polar	33892256
4-Deoxyannoreticuin,1TBDMS,isomer #3	CCCCCCCCCCCCC(O)C1CCC(C(O)CCCCCC(CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	4687.2	Semi standard non polar	33892256
4-Deoxyannoreticuin,2TBDMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(CCCCCC(O)CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	4851.1	Semi standard non polar	33892256
4-Deoxyannoreticuin,2TBDMS,isomer #2	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C1CCC(C(O)CCCCCC(CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O1	4846.8	Semi standard non polar	33892256
4-Deoxyannoreticuin,2TBDMS,isomer #3	CCCCCCCCCCCCC(O)C1CCC(C(CCCCCC(CCCCCCC2=CC(C)OC2=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	4846.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0292-1379220000-52e1e65661b7c6146ee9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (1 TMS) - 70eV, Positive	splash10-007x-3029212000-20904c38483ae93e9776	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS ("4-Deoxyannoreticuin,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Deoxyannoreticuin GC-MS (TBDMS_2_3) - 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 - 4-Deoxyannoreticuin 10V, Positive-QTOF	splash10-03e9-0010090000-ec286d369252282f6c03	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 20V, Positive-QTOF	splash10-02t9-3941150000-bfbc00ec5dcbefb56e11	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 40V, Positive-QTOF	splash10-014i-6932200000-8ae262fbf63a94044d10	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 10V, Negative-QTOF	splash10-004i-0000090000-370cdc2d0c930033c18f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 20V, Negative-QTOF	splash10-02vj-1353090000-5ce932cc2e03a894097c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 40V, Negative-QTOF	splash10-05mn-3397020000-289eb69a9eb061bd5d04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 10V, Positive-QTOF	splash10-01ot-0011190000-e2058cbcf9d862715d02	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 20V, Positive-QTOF	splash10-03dj-0010090000-14ef596199cd724f8b4e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 40V, Positive-QTOF	splash10-0007-9122000000-741a6a4d7f1a702143c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 10V, Negative-QTOF	splash10-004i-0000090000-a352987f66a5f6a639c9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 20V, Negative-QTOF	splash10-004i-1143090000-a765a1dae49b55b1fd08	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Deoxyannoreticuin 40V, Negative-QTOF	splash10-01ox-6279020000-c7cebbc39fbc14614838	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

FDB011173

KNApSAcK ID

C00054953

Chemspider ID

35013553

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74394480

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1833571

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 4-Deoxyannoreticuin (HMDB0033165)

MOL for HMDB0033165 (4-Deoxyannoreticuin)

3D MOL for HMDB0033165 (4-Deoxyannoreticuin)

3D SDF for HMDB0033165 (4-Deoxyannoreticuin)

3D-SDF for HMDB0033165 (4-Deoxyannoreticuin)

PDB for HMDB0033165 (4-Deoxyannoreticuin)

3D PDB for HMDB0033165 (4-Deoxyannoreticuin)

SMILES for HMDB0033165 (4-Deoxyannoreticuin)

INCHI for HMDB0033165 (4-Deoxyannoreticuin)

Structure for HMDB0033165 (4-Deoxyannoreticuin)

3D Structure for HMDB0033165 (4-Deoxyannoreticuin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra