NP-MRD: Showing NP-Card for 3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one (NP0251824)

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Record Information

Version

2.0

Created at

2022-09-07 15:08:04 UTC

Updated at

2022-09-07 15:08:04 UTC

NP-MRD ID

NP0251824

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one

Description

Squamotacin, also known as glaucanisin, 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. Squamotacin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Squamotacin has been detected, but not quantified in, fruits. 3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one is found in Annona squamosa. This could make squamotacin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305142D          

 44 46  0  0  0  0            999 V2000
   -8.7035   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7163   18.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9890   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2746   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5601   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8456   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1312   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4167   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7022   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3033   18.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5889   18.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0178   18.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2733   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8744   18.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7323   18.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1599   18.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8443   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6708   18.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303   19.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1233   19.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3438   18.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1299   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.4834   19.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3383   19.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628   18.1139    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
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
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 28  2  1  0  0  0  0
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 41 37  2  0  0  0  0
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 43 33  1  0  0  0  0
 43 35  1  0  0  0  0
 44 34  1  0  0  0  0
 44 36  1  0  0  0  0
M  END

     RDKit          3D

110112  0  0  0  0  0  0  0  0999 V2000
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 40 41  1  0
 41 42  2  0
 44 15  1  0
 43 19  1  0
 41 36  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  0
  2 49  1  0
  3 50  1  0
  3 51  1  0
  4 52  1  0
  4 53  1  0
  5 54  1  0
  5 55  1  0
  6 56  1  0
  6 57  1  0
  7 58  1  0
  7 59  1  0
  8 60  1  0
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  9 62  1  0
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 12 69  1  0
 13 70  1  6
 14 71  1  0
 15 72  1  1
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 17 75  1  0
 17 76  1  0
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 19 78  1  1
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 20 80  1  0
 21 81  1  0
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 22 83  1  6
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 24 85  1  0
 25 86  1  0
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 26 88  1  0
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 27 90  1  0
 27 91  1  0
 28 92  1  0
 28 93  1  0
 29 94  1  0
 29 95  1  0
 30 96  1  0
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 31 98  1  0
 31 99  1  0
 32100  1  0
 32101  1  0
 33102  1  6
 34103  1  0
 35104  1  0
 35105  1  0
 37106  1  0
 38107  1  1
 39108  1  0
 39109  1  0
 39110  1  0
M  END


  Mrv0541 05061305142D          

 44 46  0  0  0  0            999 V2000
   -8.7035   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7163   18.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9890   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2746   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5601   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8456   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1312   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4167   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7022   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3033   18.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5889   18.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0178   18.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2733   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8744   18.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7323   18.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5588   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1599   18.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4467   18.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8443   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4454   18.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6708   18.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303   19.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4778   17.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233   19.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3438   18.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8757   18.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8959   18.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5902   18.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1612   18.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299   19.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7310   18.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   18.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   18.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   18.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7108   18.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6764   19.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1612   19.2745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299   20.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7310   17.2120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0633   19.8220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4834   19.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3383   19.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628   18.1139    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
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  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
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 28  2  1  0  0  0  0
 28 26  1  0  0  0  0
 29 26  2  0  0  0  0
 29 27  1  0  0  0  0
 30 19  1  0  0  0  0
 30 27  1  0  0  0  0
 31 20  1  0  0  0  0
 32 21  1  0  0  0  0
 33 22  1  0  0  0  0
 33 31  1  0  0  0  0
 34 23  1  0  0  0  0
 34 32  1  0  0  0  0
 35 24  1  0  0  0  0
 36 25  1  0  0  0  0
 36 35  1  0  0  0  0
 37 29  1  0  0  0  0
 38 30  1  0  0  0  0
 39 31  1  0  0  0  0
 40 32  1  0  0  0  0
 41 37  2  0  0  0  0
 42 28  1  0  0  0  0
 42 37  1  0  0  0  0
 43 33  1  0  0  0  0
 43 35  1  0  0  0  0
 44 34  1  0  0  0  0
 44 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251824

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCC(O)CC1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-11-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3

> <INCHI_KEY>
GXZZLWVQYXFTJE-UHFFFAOYSA-N

> <FORMULA>
C37H66O7

> <MOLECULAR_WEIGHT>
622.9157

> <EXACT_MASS>
622.480854466

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
77.97863152759962

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.99

> <JCHEM_LOGP>
8.682191933333334

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.379912503383732

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.851679326137901

> <JCHEM_PKA_STRONGEST_BASIC>
-2.722022871174217

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
176.39659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.39e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,11-dihydroxy-11-{5-[5-(1-hydroxytridecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5-methyl-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     -16.247  36.084   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.470  34.796   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.913  35.314   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.579  36.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.246  35.314   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.912  36.084   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.578  35.314   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.245  36.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.911  35.314   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.577  36.084   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.499  34.439   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.166  33.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.833  33.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.243  35.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.832  34.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.167  34.439   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.910  36.084   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.498  33.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.501  33.669   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.576  35.314   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.165  34.439   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.252  33.783   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.337  35.970   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.759  33.462   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.830  36.291   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.908  33.813   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.168  33.669   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      25.939  34.957   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      23.502  34.439   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.834  34.439   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.242  36.084   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.831  33.669   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.091  35.314   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.497  34.439   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.529  34.796   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.060  34.957   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      23.663  35.970   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      20.834  35.979   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -0.242  37.624   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       8.831  32.129   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      22.518  37.001   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      25.169  36.291   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       2.498  35.941   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       6.091  33.813   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   28                                                            
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   14                                                       
CONECT   11   12   13                                                       
CONECT   12   11   15                                                       
CONECT   13   11   16                                                       
CONECT   14   10   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15   21                                                       
CONECT   19   16   30                                                       
CONECT   20   17   31                                                       
CONECT   21   18   32                                                       
CONECT   22   24   33                                                       
CONECT   23   25   34                                                       
CONECT   24   22   35                                                       
CONECT   25   23   36                                                       
CONECT   26   28   29                                                       
CONECT   27   29   30                                                       
CONECT   28    2   26   42                                                  
CONECT   29   26   27   37                                                  
CONECT   30   19   27   38                                                  
CONECT   31   20   33   39                                                  
CONECT   32   21   34   40                                                  
CONECT   33   22   31   43                                                  
CONECT   34   23   32   44                                                  
CONECT   35   24   36   43                                                  
CONECT   36   25   35   44                                                  
CONECT   37   29   41   42                                                  
CONECT   38   30                                                            
CONECT   39   31                                                            
CONECT   40   32                                                            
CONECT   41   37                                                            
CONECT   42   28   37                                                       
CONECT   43   33   35                                                       
CONECT   44   34   36                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

View in JSmol

Synonyms

Value	Source
Glaucanisin	HMDB

Chemical Formula

C₃₇H₆₆O₇

Average Mass

622.9157 Da

Monoisotopic Mass

622.48085 Da

IUPAC Name

3-(2,11-dihydroxy-11-{5-[5-(1-hydroxytridecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

3-(2,11-dihydroxy-11-{5-[5-(1-hydroxytridecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCC(O)CC1=CC(C)OC1=O

InChI Identifier

InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-11-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3

InChI Key

GXZZLWVQYXFTJE-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 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
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

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	6.99	ALOGPS
logP	8.68	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	176.4 m³·mol⁻¹	ChemAxon
Polarizability	77.98 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

HMDB0030444

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002309

KNApSAcK ID

Not Available

Chemspider ID

13820111

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21848333

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one (NP0251824)

MOL for NP0251824 (3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one)

3D MOL for NP0251824 (3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one)

3D SDF for NP0251824 (3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one)

3D-SDF for NP0251824 (3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one)

PDB for NP0251824 (3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one)

3D PDB for NP0251824 (3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one)

SMILES for NP0251824 (3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one)

INCHI for NP0251824 (3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one)

Structure for NP0251824 (3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one)

3D Structure for NP0251824 (3-{2,11-dihydroxy-11-[5'-(1-hydroxytridecyl)-[2,2'-bioxolan]-5-yl]undecyl}-5-methyl-5h-furan-2-one)