NP-MRD: Showing NP-Card for 5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one (NP0291484)

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Record Information

Version

1.0

Created at

2022-09-09 22:35:55 UTC

Updated at

2022-09-09 22:35:55 UTC

NP-MRD ID

NP0291484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one

Description

Purpureacin 2 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. Purpureacin 2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Purpureacin 2 has been detected, but not quantified in, alcoholic beverages and fruits. 5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one is found in Annona crassiflora and Annona purpurea. This could make purpureacin 2 a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061312102D          

 45 47  0  0  0  0            999 V2000
  -16.1602   10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2597    9.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -14.7313   10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -13.3023   10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6228    9.2193    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
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 44 33  1  0  0  0  0
 44 35  1  0  0  0  0
 45 34  1  0  0  0  0
 45 36  1  0  0  0  0
M  END

     RDKit          3D

111113  0  0  0  0  0  0  0  0999 V2000
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 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 42 43  2  0
 45 13  1  0
 44 17  1  0
 42 37  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  2 49  1  0
  2 50  1  0
  3 51  1  0
  3 52  1  0
  4 53  1  0
  4 54  1  0
  5 55  1  0
  5 56  1  0
  6 57  1  0
  6 58  1  0
  7 59  1  0
  7 60  1  0
  8 61  1  0
  8 62  1  0
  9 63  1  0
  9 64  1  0
 10 65  1  0
 10 66  1  0
 11 67  1  6
 12 68  1  0
 13 69  1  6
 14 70  1  0
 14 71  1  0
 15 72  1  0
 15 73  1  0
 16 74  1  6
 17 75  1  1
 18 76  1  0
 18 77  1  0
 19 78  1  0
 19 79  1  0
 20 80  1  1
 21 81  1  6
 22 82  1  0
 23 83  1  0
 23 84  1  0
 24 85  1  0
 24 86  1  0
 25 87  1  6
 26 88  1  0
 27 89  1  0
 27 90  1  0
 28 91  1  0
 28 92  1  0
 29 93  1  0
 29 94  1  0
 30 95  1  0
 30 96  1  0
 31 97  1  0
 31 98  1  0
 32 99  1  0
 32100  1  0
 33101  1  0
 33102  1  0
 34103  1  1
 35104  1  0
 36105  1  0
 36106  1  0
 38107  1  0
 39108  1  6
 40109  1  0
 40110  1  0
 40111  1  0
M  END


  Mrv0541 05061312102D          

 45 47  0  0  0  0            999 V2000
  -16.1602   10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2597    9.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4457   10.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7313   10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0168   10.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3023   10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5879   10.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8734   10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8466    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1322    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1589   10.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2756    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4444   10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9901    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7300   10.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7257    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4402    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2148    9.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9554   10.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4078    9.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7623   10.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8871    9.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4392    9.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7045    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0155   10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3010   10.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8691    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9953    9.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1748    9.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2197   10.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112   10.3798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7045   10.3798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0155   11.2612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547    8.3173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066   10.9274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0267   10.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5473   10.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228    9.2193    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
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 20 19  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  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 16  1  0  0  0  0
 29 19  1  0  0  0  0
 30 17  1  0  0  0  0
 30 26  1  0  0  0  0
 31 18  1  0  0  0  0
 32 20  1  0  0  0  0
 33 21  1  0  0  0  0
 33 31  1  0  0  0  0
 34 22  1  0  0  0  0
 34 32  1  0  0  0  0
 35 23  1  0  0  0  0
 36 24  1  0  0  0  0
 36 35  1  0  0  0  0
 37 28  1  0  0  0  0
 38 29  1  0  0  0  0
 39 30  1  0  0  0  0
 40 31  1  0  0  0  0
 41 32  1  0  0  0  0
 42 37  2  0  0  0  0
 43 27  1  0  0  0  0
 43 37  1  0  0  0  0
 44 33  1  0  0  0  0
 44 35  1  0  0  0  0
 45 34  1  0  0  0  0
 45 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291484

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O8/c1-3-4-5-6-7-8-12-15-18-31(40)33-21-23-35(44-33)36-24-22-34(45-36)32(41)20-19-29(38)16-13-10-9-11-14-17-30(39)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3

> <INCHI_KEY>
DDFDZKSKODBLSR-UHFFFAOYSA-N

> <FORMULA>
C37H66O8

> <MOLECULAR_WEIGHT>
638.9151

> <EXACT_MASS>
638.475769088

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
79.38866450718338

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-3-(2,10,13-trihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
5.77

> <JCHEM_LOGP>
7.295473406333334

> <ALOGPS_LOGS>
-5.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.341244899315793

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.83294161667439

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6861967452645743

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
178.06609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-3-(2,10,13-trihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-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     -30.166  19.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.551  18.193   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -28.832  18.711   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -27.498  19.481   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -26.165  18.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -24.831  19.481   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -23.497  18.711   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -22.164  19.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.580  17.836   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.247  17.066   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.914  17.066   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -20.830  18.711   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.087  17.836   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.248  17.836   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -19.496  19.481   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.421  17.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.582  17.066   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -18.163  18.711   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.088  17.066   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.422  17.836   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -15.334  17.179   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.250  19.367   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.828  16.859   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.756  19.688   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.989  17.209   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.249  17.066   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.020  18.354   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.583  17.836   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.754  17.836   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.915  17.836   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -16.829  19.481   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.755  17.066   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -15.495  18.711   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -9.089  17.836   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -13.058  18.193   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -11.526  18.354   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.743  19.367   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.754  19.376   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       6.915  19.376   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -16.829  21.021   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -7.755  15.526   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       8.599  20.398   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      11.250  19.688   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0     -14.088  19.337   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0     -10.496  17.209   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   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   29                                                       
CONECT   17   14   30                                                       
CONECT   18   15   31                                                       
CONECT   19   20   29                                                       
CONECT   20   19   32                                                       
CONECT   21   23   33                                                       
CONECT   22   24   34                                                       
CONECT   23   21   35                                                       
CONECT   24   22   36                                                       
CONECT   25   27   28                                                       
CONECT   26   28   30                                                       
CONECT   27    2   25   43                                                  
CONECT   28   25   26   37                                                  
CONECT   29   16   19   38                                                  
CONECT   30   17   26   39                                                  
CONECT   31   18   33   40                                                  
CONECT   32   20   34   41                                                  
CONECT   33   21   31   44                                                  
CONECT   34   22   32   45                                                  
CONECT   35   23   36   44                                                  
CONECT   36   24   35   45                                                  
CONECT   37   28   42   43                                                  
CONECT   38   29                                                            
CONECT   39   30                                                            
CONECT   40   31                                                            
CONECT   41   32                                                            
CONECT   42   37                                                            
CONECT   43   27   37                                                       
CONECT   44   33   35                                                       
CONECT   45   34   36                                                       
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

View in JSmol

Synonyms

Value	Source
12-Hydroxybullatacin	HMDB

Chemical Formula

C₃₇H₆₆O₈

Average Mass

638.9151 Da

Monoisotopic Mass

638.47577 Da

IUPAC Name

5-methyl-3-(2,10,13-trihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-2,5-dihydrofuran-2-one

Traditional Name

5-methyl-3-(2,10,13-trihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C37H66O8/c1-3-4-5-6-7-8-12-15-18-31(40)33-21-23-35(44-33)36-24-22-34(45-36)32(41)20-19-29(38)16-13-10-9-11-14-17-30(39)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3

InChI Key

DDFDZKSKODBLSR-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 crassiflora	LOTUS Database	35616633
Annona purpurea	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	5.77	ALOGPS
logP	7.3	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	13.83	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	178.07 m³·mol⁻¹	ChemAxon
Polarizability	79.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0040839

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020661

KNApSAcK ID

Not Available

Chemspider ID

2958831

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3728292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one (NP0291484)

MOL for NP0291484 (5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one)

3D MOL for NP0291484 (5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one)

3D SDF for NP0291484 (5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one)

3D-SDF for NP0291484 (5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one)

PDB for NP0291484 (5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one)

3D PDB for NP0291484 (5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one)

SMILES for NP0291484 (5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one)

INCHI for NP0291484 (5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one)

Structure for NP0291484 (5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one)

3D Structure for NP0291484 (5-methyl-3-{2,10,13-trihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5h-furan-2-one)