NP-MRD: Showing NP-Card for 5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one (NP0327510)

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Record Information

Version

1.0

Created at

2022-09-12 10:08:55 UTC

Updated at

2022-09-12 10:08:55 UTC

NP-MRD ID

NP0327510

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one

Description

Glacin A belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. 5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one is found in Annona glabra. It was first documented in 2000 (PMID: 11413487). Glacin A is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061306212D          

 42 43  0  0  0  0            999 V2000
  -12.4593   16.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1074   11.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1237   16.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3032   15.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9677   15.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1472   15.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8117   14.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9912   14.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6556   13.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2654   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8351   13.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8780   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7560   11.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2040   10.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7349   10.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2869   11.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7359    9.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8744   11.8523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5366   11.6807    0.0000 O   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
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  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
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 24 23  1  0  0  0  0
 27  2  1  0  0  0  0
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 29 18  1  0  0  0  0
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 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
 33 31  1  0  0  0  0
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 34 32  1  0  0  0  0
 35 28  1  0  0  0  0
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 40 35  2  0  0  0  0
 41 27  1  0  0  0  0
 41 35  1  0  0  0  0
 42 33  1  0  0  0  0
 42 34  1  0  0  0  0
M  END

     RDKit          3D

106107  0  0  0  0  0  0  0  0999 V2000
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 21 78  1  0
 21 79  1  0
 22 80  1  0
 22 81  1  0
 23 82  1  6
 24 83  1  0
 25 84  1  0
 25 85  1  0
 26 86  1  0
 26 87  1  0
 27 88  1  0
 27 89  1  0
 28 90  1  0
 28 91  1  0
 29 92  1  0
 29 93  1  0
 30 94  1  0
 30 95  1  0
 31 96  1  0
 31 97  1  0
 32 98  1  6
 33 99  1  0
 34100  1  0
 34101  1  0
 36102  1  0
 37103  1  6
 38104  1  0
 38105  1  0
 38106  1  0
M  END


  Mrv0541 05061306212D          

 42 43  0  0  0  0            999 V2000
  -12.4593   16.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1074   11.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1237   16.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3032   15.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9677   15.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1472   15.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8117   14.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9912   14.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6556   13.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2654   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8351   13.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8780   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8378   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4996   12.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0214   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7560   11.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2040   10.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7349   10.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2869   11.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9812   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6791   12.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7359   10.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3435   11.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4503   10.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0674   11.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635   11.6852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523   11.6852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1942   13.2734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7359    9.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4543   12.2328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8744   11.8523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5366   11.6807    0.0000 O   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
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  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 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 17  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
 33 31  1  0  0  0  0
 34 24  1  0  0  0  0
 34 32  1  0  0  0  0
 35 28  1  0  0  0  0
 36 29  1  0  0  0  0
 37 30  1  0  0  0  0
 38 31  1  0  0  0  0
 39 32  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
 42 33  1  0  0  0  0
 42 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327510

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C35H64O7/c1-3-4-5-6-7-8-12-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-10-9-11-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3

> <INCHI_KEY>
WRQFJAQUJPZSCT-UHFFFAOYSA-N

> <FORMULA>
C35H64O7

> <MOLECULAR_WEIGHT>
596.8785

> <EXACT_MASS>
596.465204402

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
74.78686935471339

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
6.31

> <JCHEM_LOGP>
7.706254638000001

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.380087784873801

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.85167871880019

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2743091032911185

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
169.3432

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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     -23.257  31.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.134  20.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -22.631  29.963   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -21.099  29.802   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -20.473  28.396   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -18.941  28.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -18.315  26.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -16.784  26.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.163  20.272   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.829  19.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.496  19.502   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -16.157  25.260   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.495  20.272   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.830  20.272   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -14.626  25.099   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.839  20.272   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.173  19.502   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.838  19.502   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.506  19.502   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.164  19.502   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -13.999  23.692   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.507  20.272   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.611  20.791   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -11.581  19.646   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.572  19.646   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.831  19.502   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.602  20.791   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.165  20.272   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.172  20.272   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.498  20.272   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -12.468  23.531   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.840  19.502   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -11.841  22.124   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.174  20.272   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.326  21.804   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.172  21.812   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       8.498  21.812   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -11.563  24.777   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -8.840  17.962   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      10.181  22.835   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      12.832  22.124   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -10.335  21.804   0.000  0.00  0.00           O+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   12                                                       
CONECT    9   10   11                                                       
CONECT   10    9   13                                                       
CONECT   11    9   14                                                       
CONECT   12    8   15                                                       
CONECT   13   10   18                                                       
CONECT   14   11   20                                                       
CONECT   15   12   21                                                       
CONECT   16   17   19                                                       
CONECT   17   16   22                                                       
CONECT   18   13   29                                                       
CONECT   19   16   29                                                       
CONECT   20   14   30                                                       
CONECT   21   15   31                                                       
CONECT   22   17   32                                                       
CONECT   23   24   33                                                       
CONECT   24   23   34                                                       
CONECT   25   27   28                                                       
CONECT   26   28   30                                                       
CONECT   27    2   25   41                                                  
CONECT   28   25   26   35                                                  
CONECT   29   18   19   36                                                  
CONECT   30   20   26   37                                                  
CONECT   31   21   33   38                                                  
CONECT   32   22   34   39                                                  
CONECT   33   23   31   42                                                  
CONECT   34   24   32   42                                                  
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                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₆₄O₇

Average Mass

596.8785 Da

Monoisotopic Mass

596.46520 Da

IUPAC Name

5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-2,5-dihydrofuran-2-one

Traditional Name

5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCC(O)CCCCCCCC(O)CC1=CC(C)OC1=O

InChI Identifier

InChI=1S/C35H64O7/c1-3-4-5-6-7-8-12-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-10-9-11-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3

InChI Key

WRQFJAQUJPZSCT-UHFFFAOYSA-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 glabra	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
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 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	6.31	ALOGPS
logP	7.71	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	169.34 m³·mol⁻¹	ChemAxon
Polarizability	74.79 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

HMDB0032092

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008808

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

85136945

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

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 ]
LOTUS database [Link]

Showing NP-Card for 5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one (NP0327510)

MOL for NP0327510 (5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

3D MOL for NP0327510 (5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

3D SDF for NP0327510 (5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

3D-SDF for NP0327510 (5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

PDB for NP0327510 (5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

3D PDB for NP0327510 (5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

SMILES for NP0327510 (5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

INCHI for NP0327510 (5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

Structure for NP0327510 (5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)

3D Structure for NP0327510 (5-methyl-3-{2,10,15-trihydroxy-15-[5-(1-hydroxyundecyl)oxolan-2-yl]pentadecyl}-5h-furan-2-one)