NP-MRD: Showing NP-Card for (+)-Gigantrionenin (NP0079503)

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Record Information

Version

1.0

Created at

2022-04-29 00:31:25 UTC

Updated at

2022-04-29 00:31:25 UTC

NP-MRD ID

NP0079503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Gigantrionenin

Description

Gigantrionenin 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. (+)-Gigantrionenin is found in Goniothalamus giganteus. It was first documented in 1992 (PMID: 1479382). Based on a literature review very few articles have been published on gigantrionenin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202312D          

 43 44  0  0  1  0            999 V2000
  -12.5951    4.7903    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.5089    5.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7019    5.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2894    5.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4690    4.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8415    4.4548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3664    6.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5459    6.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2103    7.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3899    7.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0543    8.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2338    8.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8983    9.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0778    9.1420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6653    9.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583    9.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7721    8.8645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5258    8.5289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576    8.4520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.6287    8.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8029    7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5173    7.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997    7.6270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0576    7.6270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3096    4.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  1  6  1  0  0  0  0
  3  7  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
 14 13  1  6  0  0  0
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 38 39  1  0  0  0  0
 23 40  1  1  0  0  0
 22 41  1  1  0  0  0
 19 42  1  6  0  0  0
  1 43  1  1  0  0  0
M  END

     RDKit          3D

109110  0  0  0  0  0  0  0  0999 V2000
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 15 72  1  0
 16 73  1  0
 16 74  1  0
 17 75  1  6
 18 76  1  0
 19 77  1  6
 20 78  1  0
 21 79  1  0
 21 80  1  0
 22 81  1  0
 22 82  1  0
 23 83  1  1
 24 84  1  0
 25 85  1  6
 26 86  1  0
 26 87  1  0
 27 88  1  0
 27 89  1  0
 28 90  1  1
 29 91  1  0
 29 92  1  0
 30 93  1  0
 30 94  1  0
 31 95  1  0
 31 96  1  0
 32 97  1  0
 32 98  1  0
 33 99  1  0
 33100  1  0
 34101  1  0
 34102  1  0
 35103  1  0
 35104  1  0
 37105  1  0
 38106  1  6
 39107  1  0
 39108  1  0
 39109  1  0
M  END


  Mrv1652304292202312D          

 43 44  0  0  1  0            999 V2000
  -12.5951    4.7903    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.5089    5.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7019    5.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2894    5.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4690    4.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8415    4.4548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3664    6.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5459    6.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2103    7.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3899    7.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0543    8.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2338    8.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8983    9.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0778    9.1420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6653    9.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583    9.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7721    8.8645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5258    8.5289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576    8.4520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3431    8.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287    8.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    8.8645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1997    8.4520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4853    8.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708    8.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708    7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563    7.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582    7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726    7.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016    7.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160    7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2305    7.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9450    7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595    7.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739    7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0884    7.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8029    7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5173    7.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997    7.6270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    9.6895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576    7.6270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3096    4.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  1  6  1  0  0  0  0
  3  7  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
 14 13  1  6  0  0  0
 14 15  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
 14 18  1  0  0  0  0
 17 19  1  1  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  2  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
 30 31  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
 34 35  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
 23 40  1  1  0  0  0
 22 41  1  1  0  0  0
 19 42  1  6  0  0  0
  1 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0079503

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC\C=C/CC[C@@H](O)[C@H](O)CC[C@H](O)[C@@H]1CC[C@@H](CCCCCCCC2=C[C@H](C)OC2=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O6/c1-3-4-5-6-7-8-9-10-11-12-13-14-18-21-24-33(38)34(39)26-27-35(40)36-28-25-32(43-36)23-20-17-15-16-19-22-31-29-30(2)42-37(31)41/h14,18,29-30,32-36,38-40H,3-13,15-17,19-28H2,1-2H3/b18-14-/t30-,32+,33+,34+,35-,36-/m0/s1

> <INCHI_KEY>
HASWAOYLTAODRS-VKJZEEHVSA-N

> <FORMULA>
C37H66O6

> <MOLECULAR_WEIGHT>
606.929

> <EXACT_MASS>
606.485939845

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
77.04601788305965

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-methyl-3-{7-[(2R,5S)-5-[(1S,4R,5R,8Z)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl]heptyl}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
8.31

> <JCHEM_LOGP>
9.620188838333332

> <ALOGPS_LOGS>
-6.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.861928665794604

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.277926940670362

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1463433441545154

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
177.99230000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.37e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-methyl-3-{7-[(2R,5S)-5-[(1S,4R,5R,8Z)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl]heptyl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0     -23.511   8.942   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -23.350  10.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -21.844  10.794   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -21.074   9.460   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -19.542   9.299   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0     -22.104   8.316   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0     -21.217  12.201   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -19.686  12.362   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -19.059  13.768   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -17.528  13.929   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -16.901  15.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -15.370  15.497   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -14.743  16.904   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -13.212  17.065   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.442  18.399   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.936  18.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.775  16.547   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -12.181  15.921   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.441  15.777   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.107  16.547   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.774  15.777   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.440  16.547   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.106  15.777   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.772  16.547   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.439  15.777   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.439  14.237   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.105  13.467   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.229  14.237   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.562  13.467   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.896  14.237   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.230  13.467   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.563  14.237   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.897  13.467   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.231  14.237   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.564  13.467   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.898  14.237   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.232  13.467   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.565  14.237   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.899  13.467   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.106  14.237   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -5.440  18.087   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -9.441  14.237   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0     -24.845   8.172   0.000  0.00  0.00           C+0
CONECT    1    2    6   43                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    1                                                       
CONECT    7    3    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   19                                                  
CONECT   18   17   14                                                       
CONECT   19   17   20   42                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   41                                                  
CONECT   23   22   24   40                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   23                                                            
CONECT   41   22                                                            
CONECT   42   19                                                            
CONECT   43    1                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   88    0
END

View in JSmol

Synonyms

Value	Source
Gigantetronenin	MeSH

Chemical Formula

C₃₇H₆₆O₆

Average Mass

606.9290 Da

Monoisotopic Mass

606.48594 Da

IUPAC Name

(5S)-5-methyl-3-{7-[(2R,5S)-5-[(1S,4R,5R,8Z)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl]heptyl}-2,5-dihydrofuran-2-one

Traditional Name

(5S)-5-methyl-3-{7-[(2R,5S)-5-[(1S,4R,5R,8Z)-1,4,5-trihydroxyhenicos-8-en-1-yl]oxolan-2-yl]heptyl}-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC\C=C/CC[C@@H](O)[C@H](O)CC[C@H](O)[C@@H]1CC[C@@H](CCCCCCCC2=C[C@H](C)OC2=O)O1

InChI Identifier

InChI=1S/C37H66O6/c1-3-4-5-6-7-8-9-10-11-12-13-14-18-21-24-33(38)34(39)26-27-35(40)36-28-25-32(43-36)23-20-17-15-16-19-22-31-29-30(2)42-37(31)41/h14,18,29-30,32-36,38-40H,3-13,15-17,19-28H2,1-2H3/b18-14-/t30-,32+,33+,34+,35-,36-/m0/s1

InChI Key

HASWAOYLTAODRS-VKJZEEHVSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Goniothalamus giganteus	Plant	KNApSAcK

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

secondary alcohol (CHEBI:65963 )
butenolide (CHEBI:65963 )
polyketide (CHEBI:65963 )
triol (CHEBI:65963 )
oxolanes (CHEBI:65963 )

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	8.31	ALOGPS
logP	9.62	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	13.28	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	177.99 m³·mol⁻¹	ChemAxon
Polarizability	77.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00044122

Chemspider ID

4580430

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5470005

PDB ID

Not Available

ChEBI ID

65963

Good Scents ID

Not Available

References

General References

Fang XP, Anderson JE, Smith DL, McLaughlin JL, Wood KV: Gigantetronenin and gigantrionenin: novel cytotoxic acetogenins from Goniothalamus giganteus. J Nat Prod. 1992 Nov;55(11):1655-63. doi: 10.1021/np50089a015. [PubMed:1479382 ]

Showing NP-Card for (+)-Gigantrionenin (NP0079503)

MOL for NP0079503 ((+)-Gigantrionenin)

3D MOL for NP0079503 ((+)-Gigantrionenin)

3D SDF for NP0079503 ((+)-Gigantrionenin)

3D-SDF for NP0079503 ((+)-Gigantrionenin)

PDB for NP0079503 ((+)-Gigantrionenin)

3D PDB for NP0079503 ((+)-Gigantrionenin)

SMILES for NP0079503 ((+)-Gigantrionenin)

INCHI for NP0079503 ((+)-Gigantrionenin)

Structure for NP0079503 ((+)-Gigantrionenin)

3D Structure for NP0079503 ((+)-Gigantrionenin)