NP-MRD: Showing NP-Card for methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate (NP0208774)

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Record Information

Version

2.0

Created at

2022-09-05 05:54:52 UTC

Updated at

2022-09-05 05:54:52 UTC

NP-MRD ID

NP0208774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate

Description

Methyl (3aS,4S,5S,11aS)-5-(acetyloxy)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review very few articles have been published on methyl (3aS,4S,5S,11aS)-5-(acetyloxy)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052207542D          

 33 34  0  0  1  0            999 V2000
    2.9609   -0.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780    0.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487    0.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733    0.5863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4764    1.6611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009    1.6895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8315    2.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6439    2.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1745    2.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9257    1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0200    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4894   -0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7712   -0.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1040   -1.2334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5836   -1.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8654   -1.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -0.0049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1464   -0.6366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4282   -1.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2406   -1.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8976   -2.0437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3952    0.7705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0858    0.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688   -0.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611    0.5416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594   -0.8735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1946   -0.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7242   -1.1829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -1.6383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1576   -2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8330   -1.7528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828    0.9141    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  6  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  1  0  0  0
 23 33  1  0  0  0  0
 33  2  1  1  0  0  0
  6 33  1  0  0  0  0
M  END

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
    1.0789    1.2643   -3.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3286    0.2339   -3.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2705   -1.0376   -3.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1365   -1.5153   -4.6091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9225   -1.6278   -3.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2216   -1.2140   -2.1045 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7216   -2.3000   -1.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050   -2.5148   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7528   -3.6391    0.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2768   -1.6258    0.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8014   -1.1035    1.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7144    0.3308    1.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543    1.3790    1.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4950    2.6825    2.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7715    2.7348    3.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300    3.8891    1.4018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719    5.1284    2.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1134    1.5783   -0.1526 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3782    1.6110   -0.8334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9172    2.6832   -1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2473    2.5461   -2.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2986    3.7587   -1.4851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146    0.6730   -0.7711 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5845   -0.1910    0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521   -0.1373    0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5561    0.8129   -0.2963 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6593   -1.0672    1.1914 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2458   -0.2493    2.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8795   -2.0366    1.7706 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8472   -1.6772    0.4867 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7320   -2.4696    1.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919   -2.5445   -0.5037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6605    0.1228   -2.0485 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7399    1.1903   -4.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628    2.2039   -2.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587   -1.1923   -2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0818   -2.9910   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3683   -4.5203    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2859   -3.9346    0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0201   -3.4897    1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6970   -0.9193   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449   -2.3591    0.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323   -1.6191    2.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7715   -1.4903    2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9382    0.5336    3.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664    5.9456    1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9970    4.9564    2.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2941    5.3628    2.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7668    2.6672   -0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7633    3.5335   -1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0865    2.3460   -3.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8663    1.7727   -1.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7207    1.3850   -1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0216    0.4286    1.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441   -0.9065    3.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3851    0.4035    2.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2006   -2.9466    1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4569   -0.8636    0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1015   -1.8642    2.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6323   -2.7745    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1920   -3.3346    1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -2.8394   -1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4686    0.8385   -2.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 33  1  0
 33 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  1
 27 30  1  0
 30 31  1  0
 30 32  1  0
 23 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 13  1  0
 33  6  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 12 45  1  0
 11 43  1  0
 11 44  1  0
 10 41  1  0
 10 42  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
  7 37  1  0
  6 36  1  6
  1 34  1  0
  1 35  1  0
 33 63  1  6
 23 53  1  6
 28 54  1  0
 28 55  1  0
 28 56  1  0
 29 57  1  0
 30 58  1  6
 31 59  1  0
 31 60  1  0
 31 61  1  0
 32 62  1  0
 18 49  1  1
 21 50  1  0
 21 51  1  0
 21 52  1  0
M  END


  Mrv1652309052207542D          

 33 34  0  0  1  0            999 V2000
    2.9609   -0.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780    0.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487    0.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733    0.5863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4764    1.6611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009    1.6895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8315    2.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6439    2.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1745    2.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9257    1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0200    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4894   -0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7712   -0.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1040   -1.2334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5836   -1.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8654   -1.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -0.0049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1464   -0.6366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4282   -1.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2406   -1.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8976   -2.0437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3952    0.7705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0858    0.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688   -0.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611    0.5416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594   -0.8735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1946   -0.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7242   -1.1829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -1.6383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1576   -2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8330   -1.7528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828    0.9141    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  6  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  1  0  0  0
 23 33  1  0  0  0  0
 33  2  1  1  0  0  0
  6 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0208774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CCC\C(C)=C/[C@@H]2OC(=O)C(=C)[C@@H]2[C@H](OC(=O)[C@@](C)(O)[C@@H](C)O)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O10/c1-11-8-7-9-15(21(27)30-6)18(31-14(4)25)19(33-22(28)23(5,29)13(3)24)17-12(2)20(26)32-16(17)10-11/h9-10,13,16-19,24,29H,2,7-8H2,1,3-6H3/b11-10-,15-9?/t13-,16+,17+,18+,19+,23+/m1/s1

> <INCHI_KEY>
WKVRXCYBZOWRLM-OXSVANTFSA-N

> <FORMULA>
C23H30O10

> <MOLECULAR_WEIGHT>
466.483

> <EXACT_MASS>
466.183897166

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.72543050132613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (3aS,4S,5S,11aS)-5-(acetyloxy)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_LOGP>
1.5591266490000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.818242984627805

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.671465624734736

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2297160305667134

> <JCHEM_POLAR_SURFACE_AREA>
145.66000000000003

> <JCHEM_REFRACTIVITY>
114.38580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3aS,4S,5S,11aS)-5-(acetyloxy)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.527  -0.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.559   0.558   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.198   1.621   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.750   1.094   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.623   3.101   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.162   3.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.152   4.333   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.669   4.065   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.659   5.244   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.195   2.618   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.711   2.349   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.237   0.902   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.247  -0.277   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.773  -1.725   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.527  -2.302   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.289  -1.993   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.815  -3.440   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.730  -0.009   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.740  -1.188   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.266  -2.636   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.783  -2.904   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.276  -3.815   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.204   1.438   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.627   0.011   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.102  -0.203   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.154   1.011   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.524  -1.631   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.097  -1.053   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.952  -2.208   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.947  -3.058   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.894  -4.272   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.422  -3.272   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.688   1.706   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   23    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
Methyl (3as,4S,5S,11as)-5-(acetyloxy)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylic acid	Generator

Chemical Formula

C₂₃H₃₀O₁₀

Average Mass

466.4830 Da

Monoisotopic Mass

466.18390 Da

IUPAC Name

methyl (3aS,4S,5S,11aS)-5-(acetyloxy)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

methyl (3aS,4S,5S,11aS)-5-(acetyloxy)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CCC\C(C)=C/[C@@H]2OC(=O)C(=C)[C@@H]2[C@H](OC(=O)[C@@](C)(O)[C@@H](C)O)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C23H30O10/c1-11-8-7-9-15(21(27)30-6)18(31-14(4)25)19(33-22(28)23(5,29)13(3)24)17-12(2)20(26)32-16(17)10-11/h9-10,13,16-19,24,29H,2,7-8H2,1,3-6H3/b11-10-,15-9?/t13-,16+,17+,18+,19+,23+/m1/s1

InChI Key

WKVRXCYBZOWRLM-OXSVANTFSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Germacrane sesquiterpenoid
Tetracarboxylic acid or derivatives
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.56	ChemAxon
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	114.39 m³·mol⁻¹	ChemAxon
Polarizability	45.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

163194631

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate (NP0208774)

MOL for NP0208774 (methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D MOL for NP0208774 (methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D SDF for NP0208774 (methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D-SDF for NP0208774 (methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

PDB for NP0208774 (methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D PDB for NP0208774 (methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

SMILES for NP0208774 (methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

INCHI for NP0208774 (methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

Structure for NP0208774 (methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D Structure for NP0208774 (methyl (3as,4s,5s,11as)-5-(acetyloxy)-4-{[(2s,3r)-2,3-dihydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)