NP-MRD: Showing NP-Card for 3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one (NP0328334)

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Record Information

Version

1.0

Created at

2022-09-12 11:43:06 UTC

Updated at

2022-09-12 11:43:06 UTC

NP-MRD ID

NP0328334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one

Description

Annoreticuin-9-one 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. 3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one is found in Annona reticulata and Annona squamosa. Annoreticuin-9-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307301920032D          

 48 49  0  0  1  0            999 V2000
   16.7857   -5.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.6296   -5.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2941   -4.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4736   -4.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1380   -3.4542    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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 31 45  1  1  0  0  0
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 33 47  1  6  0  0  0
 34 48  1  1  0  0  0
M  END

     RDKit          3D

104105  0  0  0  0  0  0  0  0999 V2000
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 30 93  1  0
 29 90  1  0
 29 91  1  0
 28 88  1  0
 28 89  1  0
 25 86  1  0
 25 87  1  0
 24 84  1  0
 24 85  1  0
 23 82  1  0
 23 83  1  0
 22 80  1  0
 22 81  1  0
 21 78  1  0
 21 79  1  0
 19 76  1  1
 20 77  1  0
 18 75  1  1
 17 73  1  0
 17 74  1  0
 16 71  1  0
 16 72  1  0
 15 70  1  6
 13 68  1  1
 14 69  1  0
 12 66  1  0
 12 67  1  0
 11 64  1  0
 11 65  1  0
 10 62  1  0
 10 63  1  0
  9 60  1  0
  9 61  1  0
  8 58  1  0
  8 59  1  0
  7 56  1  0
  7 57  1  0
  6 54  1  0
  6 55  1  0
  5 52  1  0
  5 53  1  0
  4 50  1  0
  4 51  1  0
  3 48  1  0
  3 49  1  0
  2 46  1  0
  2 47  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
 34 98  1  0
 34 99  1  0
 36100  1  0
 37101  1  1
 38102  1  0
 38103  1  0
 38104  1  0
M  END


  Mrv1652307301920032D          

 48 49  0  0  1  0            999 V2000
   16.7857   -5.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5081    0.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4501   -5.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6296   -5.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2941   -4.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4736   -4.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1380   -3.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3176   -3.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9820   -2.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1615   -2.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8260   -1.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7628    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0483    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0055   -1.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4773    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3339    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6699   -0.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9264    0.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3744    1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356    1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876    0.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8494   -0.8483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9062    1.3099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5139   -0.0946    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6207    0.8974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4681    0.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194    2.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    0.0724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3645   -1.5157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9062    2.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551   -0.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2751   -0.0946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7069    0.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369   -0.0720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    1.7224    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3344   -0.1808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9062    0.4849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947   -0.7357    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6639    1.7213    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 24 23  1  0  0  0  0
 27  2  1  0  0  0  0
 27 25  1  0  0  0  0
 28 25  2  0  0  0  0
 28 26  1  0  0  0  0
 29 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 20  1  0  0  0  0
 30 26  1  0  0  0  0
 31 21  1  0  0  0  0
 32 22  1  0  0  0  0
 33 23  1  0  0  0  0
 31 33  1  0  0  0  0
 34 24  1  6  0  0  0
 32 34  1  0  0  0  0
 35 28  1  0  0  0  0
 36 29  2  0  0  0  0
 37 30  1  0  0  0  0
 31 38  1  0  0  0  0
 32 39  1  0  0  0  0
 40 35  2  0  0  0  0
 41 27  1  0  0  0  0
 41 35  1  0  0  0  0
 33 42  1  1  0  0  0
 34 42  1  0  0  0  0
 43 27  1  0  0  0  0
 44 30  1  0  0  0  0
 31 45  1  1  0  0  0
 32 46  1  1  0  0  0
 33 47  1  6  0  0  0
 34 48  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0328334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(O)(CCCCC(=O)CCCCC[C@]([H])(O)[C@]1([H])CC[C@]([H])(O1)[C@@]([H])(O)CCCCCCCCCCCC)CC1=CC([H])(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H62O7/c1-3-4-5-6-7-8-9-10-11-14-21-31(38)33-23-24-34(42-33)32(39)22-15-12-13-18-29(36)19-16-17-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,30-34,37-39H,3-24,26H2,1-2H3/t27?,30?,31-,32-,33-,34-/m0/s1

> <INCHI_KEY>
QCICHLFBIUXRKT-YJWYFJGCSA-N

> <FORMULA>
C35H62O7

> <MOLECULAR_WEIGHT>
594.874

> <EXACT_MASS>
594.449554336

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
72.54572098351161

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
7.913755439666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.972783324347006

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.312196852597332

> <JCHEM_PKA_STRONGEST_BASIC>
-2.722030497831227

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
168.3151

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0      31.333 -10.990   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.548   1.318   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.707  -9.584   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.175  -9.423   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.549  -8.016   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.017  -7.855   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.391  -6.448   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.860  -6.287   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.233  -4.880   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.701  -4.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.075  -3.312   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.757   1.675   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.423   2.445   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.544  -3.151   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.091   2.445   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.089   2.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.755   1.675   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.090   1.675   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.422   1.675   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.421   2.445   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.917  -1.744   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.425   1.675   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.529   1.157   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.499   2.302   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.986   2.302   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.017   1.157   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.580   1.675   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.756   2.445   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.088   1.675   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.386  -1.583   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.758   2.445   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.759  -0.177   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.092   1.675   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.740   0.144   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.756   3.985   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.088   0.135   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      17.480  -2.829   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      14.758   3.985   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -1.596  -0.887   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -4.247  -0.177   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      16.253   0.144   0.000  0.00  0.00           O+0
HETATM   43  H   UNK     0      -5.856  -0.134   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.088   3.215   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      19.291  -0.337   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      14.758   0.905   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      16.790  -1.373   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      16.173   3.213   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2   27                                                            
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   14                                                       
CONECT   12   13   15                                                       
CONECT   13   12   18                                                       
CONECT   14   11   21                                                       
CONECT   15   12   22                                                       
CONECT   16   17   19                                                       
CONECT   17   16   20                                                       
CONECT   18   13   29                                                       
CONECT   19   16   29                                                       
CONECT   20   17   30                                                       
CONECT   21   14   31                                                       
CONECT   22   15   32                                                       
CONECT   23   24   33                                                       
CONECT   24   23   34                                                       
CONECT   25   27   28                                                       
CONECT   26   28   30                                                       
CONECT   27    2   25   41   43                                             
CONECT   28   25   26   35                                                  
CONECT   29   18   19   36                                                  
CONECT   30   20   26   37   44                                             
CONECT   31   21   33   38   45                                             
CONECT   32   22   34   39   46                                             
CONECT   33   23   31   42   47                                             
CONECT   34   24   32   42   48                                             
CONECT   35   28   40   41                                                  
CONECT   36   29                                                            
CONECT   37   30                                                            
CONECT   38   31                                                            
CONECT   39   32                                                            
CONECT   40   35                                                            
CONECT   41   27   35                                                       
CONECT   42   33   34                                                       
CONECT   43   27                                                            
CONECT   44   30                                                            
CONECT   45   31                                                            
CONECT   46   32                                                            
CONECT   47   33                                                            
CONECT   48   34                                                            
MASTER        0    0    0    0    0    0    0    0   48    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₆₂O₇

Average Mass

594.8740 Da

Monoisotopic Mass

594.44955 Da

IUPAC Name

3-[(13S)-2,13-dihydroxy-13-[(2S,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]C(O)(CCCCC(=O)CCCCC[C@]([H])(O)[C@]1([H])CC[C@]([H])(O1)[C@@]([H])(O)CCCCCCCCCCCC)CC1=CC([H])(C)OC1=O

InChI Identifier

InChI=1S/C35H62O7/c1-3-4-5-6-7-8-9-10-11-14-21-31(38)33-23-24-34(42-33)32(39)22-15-12-13-18-29(36)19-16-17-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,30-34,37-39H,3-24,26H2,1-2H3/t27?,30?,31-,32-,33-,34-/m0/s1

InChI Key

QCICHLFBIUXRKT-YJWYFJGCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona reticulata	LOTUS Database	35616633
Annona squamosa	LOTUS Database	35616633

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	7.91	ChemAxon
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	168.32 m³·mol⁻¹	ChemAxon
Polarizability	72.55 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020662

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44584478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one (NP0328334)

MOL for NP0328334 (3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one)

3D MOL for NP0328334 (3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one)

3D SDF for NP0328334 (3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one)

3D-SDF for NP0328334 (3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one)

PDB for NP0328334 (3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one)

3D PDB for NP0328334 (3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one)

SMILES for NP0328334 (3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one)

INCHI for NP0328334 (3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one)

Structure for NP0328334 (3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one)

3D Structure for NP0328334 (3-[(13s)-2,13-dihydroxy-13-[(2s,5s)-5-[(1s)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-5-methyl-5h-furan-2-one)