NP-MRD: Showing NP-Card for purpureacin-1 (NP0229580)

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Record Information

Version

2.0

Created at

2022-09-06 09:42:35 UTC

Updated at

2022-09-06 09:42:35 UTC

NP-MRD ID

NP0229580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

purpureacin-1

Description

Bullatanocin, also known as squamostatin C or annonin IV, 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. Bullatanocin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Bullatanocin has been detected, but not quantified in, alcoholic beverages and fruits. purpureacin-1 is found in Annona atemoya, Annona cherimola, Annona glabra, Annona purpurea, Eurytides marcellus, Annona rensoniana and Annona mucosa. This could make bullatanocin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241209052D          

 45 47  0  0  0  0            999 V2000
    7.9188    3.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1320    2.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6135    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0619    1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7662    0.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9520    0.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6563   -0.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6198   -2.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3240   -2.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5084   -2.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1345   -3.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189   -3.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9253   -2.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0068    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4321    1.3065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9020    2.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5003    1.2611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 43  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 44  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 42  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
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 17 36  1  0  0  0  0
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 29 41  1  0  0  0  0
 30 31  1  0  0  0  0
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 31 32  1  0  0  0  0
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 33 39  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
M  END

     RDKit          3D

111113  0  0  0  0  0  0  0  0999 V2000
   12.4455   -1.1591    4.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8815   -0.4455    3.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6821   -0.7178    1.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1066    0.0061    0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6999   -0.4253    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0683    0.2693   -0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0281    1.7779   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3973    2.4543   -1.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
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 34 36  1  0
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 37 38  2  0
 38 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 42 43  2  0
 26 44  1  0
 45 13  1  0
 44 23  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  1
 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  6
 18 76  1  0
 19 77  1  0
 19 78  1  0
 20 79  1  0
 20 80  1  0
 21 81  1  6
 22 82  1  0
 23 83  1  1
 24 84  1  0
 24 85  1  0
 25 86  1  0
 25 87  1  0
 26 88  1  1
 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  6
 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 02241209052D          

 45 47  0  0  0  0            999 V2000
    7.9188    3.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1320    2.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6135    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0619    1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7662    0.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9520    0.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6563   -0.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8408   -0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5451   -1.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308   -1.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4338   -1.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6198   -2.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3240   -2.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5084   -2.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1345   -3.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189   -3.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1895   -2.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9253   -2.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5003    3.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1647    2.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3423    2.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0068    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1872    1.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8515    0.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0319    0.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6949    0.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8752    0.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5369   -0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186   -0.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3446   -1.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186   -2.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1355   -2.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3983   -2.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289   -1.6831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.5237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552   -2.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365   -2.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9736   -2.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -2.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200   -3.6967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2690   -0.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4321    1.3065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9020    2.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8595    1.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5003    1.2611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 43  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 44  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 42  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 36  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 41  1  0  0  0  0
 30 31  1  0  0  0  0
 30 34  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 39  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0229580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCC(O)C1CCC(O1)C(O)CCC(O)C1CCC(CCCCCCCC(O)CC2=CC(C)OC2=O)O1

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

> <INCHI_KEY>
HKMBLJVHVBJAIH-UHFFFAOYSA-N

> <FORMULA>
C37H66O8

> <MOLECULAR_WEIGHT>
638.9151

> <EXACT_MASS>
638.475769088

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
78.47954580805492

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[9-(5-{1,4-dihydroxy-4-[5-(1-hydroxyundecyl)oxolan-2-yl]butyl}oxolan-2-yl)-2-hydroxynonyl]-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
5.83

> <JCHEM_LOGP>
7.295473406333334

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.139604101039698

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.687926253569302

> <JCHEM_PKA_STRONGEST_BASIC>
-2.722022871174243

> <JCHEM_POLAR_SURFACE_AREA>
125.68

> <JCHEM_REFRACTIVITY>
178.0661

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
purpureacin-1

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      14.782   6.901   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.180   5.414   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.212   4.215   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.049   2.922   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.497   1.484   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.977   1.243   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.425  -0.195   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.903  -0.436   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.351  -1.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.831  -2.113   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.276  -3.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.757  -3.792   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.205  -5.232   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.682  -5.473   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.984  -6.841   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.462  -6.603   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.220  -5.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.594  -4.382   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0     -17.734   6.315   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -17.107   4.908   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -15.572   4.744   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -14.946   3.340   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.416   3.178   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -12.789   1.771   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.260   1.610   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -10.630   0.203   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.100   0.041   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.469  -1.366   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.941  -1.527   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.243  -2.898   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.941  -4.271   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.853  -5.360   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.477  -4.659   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.721  -3.142   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.770  -2.844   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.850  -4.382   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.441  -5.219   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.817  -4.521   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.106  -5.360   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -3.024  -6.901   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -6.102  -0.234   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      12.007   2.439   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      16.617   4.862   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      16.538   3.322   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      17.734   2.354   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   43                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   44                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   42                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   14   17                                                       
CONECT   19   20                                                            
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   41                                                  
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   39                                                  
CONECT   34   30   33                                                       
CONECT   35   36                                                            
CONECT   36   17   35   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   33   38   40                                                  
CONECT   40   39                                                            
CONECT   41   29                                                            
CONECT   42    6                                                            
CONECT   43    2   44                                                       
CONECT   44    4   43   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

View in JSmol

Synonyms

Value	Source
Annonin IV	HMDB
Cherimolin 2	HMDB
Crassiflorin	HMDB
Purpureacin 1	HMDB
Squamostatin C	HMDB
Bullatalicin	HMDB
Bullatanocin	MeSH

Chemical Formula

C₃₇H₆₆O₈

Average Mass

638.9151 Da

Monoisotopic Mass

638.47577 Da

IUPAC Name

3-[9-(5-{1,4-dihydroxy-4-[5-(1-hydroxyundecyl)oxolan-2-yl]butyl}oxolan-2-yl)-2-hydroxynonyl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

purpureacin-1

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC(O)C1CCC(O1)C(O)CCC(O)C1CCC(CCCCCCCC(O)CC2=CC(C)OC2=O)O1

InChI Identifier

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

InChI Key

HKMBLJVHVBJAIH-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 atemoya	LOTUS Database	35616633
Annona cherimola	LOTUS Database	35616633
Annona glabra	LOTUS Database	35616633
Annona purpurea	LOTUS Database	35616633
Eurytides marcellus	LOTUS Database	35616633
Rollinia membranacea	LOTUS Database	35616633
Rollinia mucosa	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
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

polyketide (CHEBI:8643 )

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	5.83	ALOGPS
logP	7.3	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	13.69	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	78.48 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