NP-MRD: Showing NP-Card for Phyllolactone D (NP0333176)

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Record Information

Version

2.0

Created at

2024-05-12 03:43:10 UTC

Updated at

2026-02-18 12:07:21 UTC

NP-MRD ID

NP0333176

Natural Product DOI

https://doi.org/10.57994/2501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phyllolactone D

Description

Phyllolactone D 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. Phyllolactone D was first documented in 2022 (PMID: 35727327). Based on a literature review very few articles have been published on Phyllolactone D.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01242306192D          

 41 45  0  0  1  0            999 V2000
    5.1979    1.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816    1.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1403    0.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666   -0.0491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6880   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623   -0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390    0.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0141    0.4627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4157    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -0.2580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0358   -0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607   -0.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1892    0.4501    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876   -0.2705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2109   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860   -0.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611   -1.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378   -0.2956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129   -0.3082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4685   -1.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580   -0.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5889   -1.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9353    0.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618   -0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -1.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -1.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9410    1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.4376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9627   -0.2831    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908    1.1708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9924    1.8915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5690    2.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    2.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9706    3.3202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 10 13  1  6  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  0  0  0  0
 32 18  1  0  0  0  0
 32 33  1  1  0  0  0
 34 32  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 37 36  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END


  Mrv2104 01242306192D          

 41 45  0  0  1  0            999 V2000
    5.1979    1.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3816    1.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1403    0.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666   -0.0491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6880   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623   -0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8390    0.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0141    0.4627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4157    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -0.2580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0358   -0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8607   -0.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1892    0.4501    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876   -0.2705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2109   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860   -0.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611   -1.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378   -0.2956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129   -0.3082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4685   -1.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580   -0.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5889   -1.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104    0.4000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9353    0.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618   -0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -1.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -1.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9410    1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.4376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9627   -0.2831    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908    1.1708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9924    1.8915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5690    2.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    2.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9706    3.3202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 10 13  1  6  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  0  0  0  0
 32 18  1  0  0  0  0
 32 33  1  1  0  0  0
 34 32  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 37 36  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@@]3(C)[C@]4([H])CCC5=C(C(=O)O[C@H]5C)[C@@]4(C)[C@H](C[C@]3([H])[C@@]1(C)CC[C@@H](OC(=O)CC)[C@@]2(C)CC)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H48O6/c1-9-26(34)38-24-14-16-30(6)21(29(24,5)10-2)13-15-31(7)22-12-11-20-18(3)36-28(35)27(20)32(22,8)25(17-23(30)31)37-19(4)33/h18,21-25H,9-17H2,1-8H3/t18-,21-,22-,23+,24+,25-,29-,30-,31-,32+/m0/s1

> <INCHI_KEY>
FOJBYUBLLYNGHS-USZLPWJASA-N

> <FORMULA>
C32H48O6

> <MOLECULAR_WEIGHT>
528.73

> <EXACT_MASS>
528.345089266

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
60.55806632349508

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,5aS,5bR,7aR,8S,9R,11aR,11bR,13S,13aS)-13-(acetyloxy)-8-ethyl-3,5b,8,11a,13a-pentamethyl-1-oxo-1H,3H,4H,5H,5aH,5bH,6H,7H,7aH,8H,9H,10H,11H,11aH,11bH,12H,13H,13aH-chryseno[1,2-c]furan-9-yl propanoate

> <JCHEM_LOGP>
6.068803436666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.892456005744375

> <JCHEM_PKA_STRONGEST_BASIC>
-6.506298786095263

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
144.20699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,5aS,5bR,7aR,8S,9R,11aR,11bR,13S,13aS)-13-(acetyloxy)-8-ethyl-3,5b,8,11a,13a-pentamethyl-1-oxo-3H,4H,5H,5aH,6H,7H,7aH,9H,10H,11H,11bH,12H,13H-chryseno[1,2-c]furan-9-yl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JAN-23         0                                  
HETATM    1  O   UNK     0       9.703   3.548   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.046   2.047   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.462   1.442   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.324  -0.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.484  -1.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.823  -0.435   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.033   0.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.493   0.864   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.243   2.209   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.743  -0.482   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.534  -1.803   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.073  -1.780   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       5.953   0.840   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       5.204  -0.505   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.994  -1.827   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.454  -1.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.914  -1.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.124  -0.552   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       0.584  -0.575   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.875  -2.088   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.855  -1.124   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.099  -2.644   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.206   0.747   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.746   0.723   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.496  -0.622   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.035  -0.645   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.785  -1.991   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.705  -1.944   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.543   2.092   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.083   2.115   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.874   0.793   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.623   2.139   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.413   0.817   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0       3.664  -0.528   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0       5.163   2.162   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.703   2.185   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.452   3.531   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.662   4.853   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.122   4.829   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       7.412   6.198   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10   37                                             
CONECT    9    8                                                            
CONECT   10    8   11   13   14                                             
CONECT   11   10   12                                                       
CONECT   12   11    6                                                       
CONECT   13   10                                                            
CONECT   14   10   15   16   34                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   32                                             
CONECT   19   18                                                            
CONECT   20   18   21   22   24                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   20   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26                                                            
CONECT   30   24   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   18   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   14   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36    8   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₈O₆

Average Mass

528.7300 Da

Monoisotopic Mass

528.34509 Da

IUPAC Name

(3S,5aS,5bR,7aR,8S,9R,11aR,11bR,13S,13aS)-13-(acetyloxy)-8-ethyl-3,5b,8,11a,13a-pentamethyl-1-oxo-1H,3H,4H,5H,5aH,5bH,6H,7H,7aH,8H,9H,10H,11H,11aH,11bH,12H,13H,13aH-chryseno[1,2-c]furan-9-yl propanoate

Traditional Name

(3S,5aS,5bR,7aR,8S,9R,11aR,11bR,13S,13aS)-13-(acetyloxy)-8-ethyl-3,5b,8,11a,13a-pentamethyl-1-oxo-3H,4H,5H,5aH,6H,7H,7aH,9H,10H,11H,11bH,12H,13H-chryseno[1,2-c]furan-9-yl propanoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@@]3(C)[C@]4([H])CCC5=C(C(=O)O[C@H]5C)[C@@]4(C)[C@H](C[C@]3([H])[C@@]1(C)CC[C@@H](OC(=O)CC)[C@@]2(C)CC)OC(C)=O

InChI Identifier

InChI=1S/C32H48O6/c1-9-26(34)38-24-14-16-30(6)21(29(24,5)10-2)13-15-31(7)22-12-11-20-18(3)36-28(35)27(20)32(22,8)25(17-23(30)31)37-19(4)33/h18,21-25H,9-17H2,1-8H3/t18-,21-,22-,23+,24+,25-,29-,30-,31-,32+/m0/s1

InChI Key

FOJBYUBLLYNGHS-USZLPWJASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 800.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-18	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Phyllospongia bergquistae		Not Available
Phyllospongia bergquistae		Not Available

Chemical Taxonomy

Description

This compound 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
Sesterterpenoid
Scalarane sesterterpenoid
Retinoid ester
Steroid
16-oxasteroid
Fatty alcohol ester
Tricarboxylic acid or derivatives
Fatty acid ester
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	6.07	ChemAxon
pKa (Strongest Acidic)	8.89	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	144.21 m³·mol⁻¹	ChemAxon
Polarizability	60.56 Å³	ChemAxon
Number of Rings	5	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hayes S, Taki AC, Lum KY, Byrne JJ, White JM, Ekins MG, Gasser RB, Davis RA: Identification of Anthelmintic Bishomoscalarane Sesterterpenes from the Australian Marine Sponge Phyllospongia bergquistae and Structure Revision of Phyllolactones A-D. J Nat Prod. 2022 Jul 22;85(7):1723-1729. doi: 10.1021/acs.jnatprod.2c00229. Epub 2022 Jun 21. [PubMed:35727327 ]
DOI: 10.1021/acs.jnatprod.2c00229

Showing NP-Card for Phyllolactone D (NP0333176)

MOL for NP0333176 (Phyllolactone D)

3D MOL for NP0333176 (Phyllolactone D)

3D SDF for NP0333176 (Phyllolactone D)

3D-SDF for NP0333176 (Phyllolactone D)

PDB for NP0333176 (Phyllolactone D)

3D PDB for NP0333176 (Phyllolactone D)

SMILES for NP0333176 (Phyllolactone D)

INCHI for NP0333176 (Phyllolactone D)

Structure for NP0333176 (Phyllolactone D)

3D Structure for NP0333176 (Phyllolactone D)