NP-MRD: Showing NP-Card for methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate (NP0280468)

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Record Information

Version

2.0

Created at

2022-09-09 06:16:48 UTC

Updated at

2022-09-09 06:16:48 UTC

NP-MRD ID

NP0280468

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate

Description

Methyl (1'S,2S,2'S,3R,4E,4'S,6'R,7'S)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]Decan]-9'-ene-10'-carboxylate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate is found in Morinda coreia. Based on a literature review very few articles have been published on methyl (1'S,2S,2'S,3R,4E,4'S,6'R,7'S)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]Decan]-9'-ene-10'-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092208162D          

 43 48  0  0  1  0            999 V2000
    5.8135    4.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3069    3.8140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6176    3.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4348    2.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110    2.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4217    1.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0979    1.0962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5913    0.4450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020   -0.3192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7192   -0.4323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299   -1.1966    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8471   -1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1577   -2.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233   -1.8478    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8339   -2.6121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061   -1.7347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1995   -2.3859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954   -0.9704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5782   -0.8573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    1.8605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2938    2.5117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8310    3.1946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2364    3.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0385    2.9656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0114    2.1410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9843    1.3165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918    1.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9112    0.3116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7290    1.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045    1.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687    1.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5156    2.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089    2.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6978    3.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2621    3.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    4.7079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625    3.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9982    4.6538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    4.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    3.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2356    2.4216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0065    3.2141    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  6  0  0  0
  8 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22  5  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  2  0  0  0  0
 33 41  1  0  0  0  0
 30 42  1  0  0  0  0
 26 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END

     RDKit          3D

 75 80  0  0  0  0  0  0  0  0999 V2000
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    3.5363    4.8190   -0.4627 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0525    3.7751    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3139    3.7712    0.4053 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    2.7793    0.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8306    1.8082    1.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738    0.8631    2.2407 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9414    0.2632    1.3963 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1715   -0.4556    2.2634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4296   -1.8107    2.1547 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2610   -2.4971    1.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738   -3.8293    1.5628 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4115   -4.1065    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492   -3.4141   -0.6589 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0962    3.9774   -0.0733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1763    2.6670   -0.4627 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.9666    1.9864    1.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8506    2.4295    2.5414 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4429    1.1636   -0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5713    2.0477    0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7320    0.4297   -1.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3774   -1.0656   -2.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6956   -0.9682   -3.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7283    0.5084   -5.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571    0.5217   -2.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9091   -0.2511   -0.8347 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4882   -0.4961    0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4986   -2.8175    4.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436    1.1130   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6981    3.6101   -1.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4269    2.3732   -1.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4427   -0.4660   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2794   -1.6778   -2.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9609   -2.2201   -4.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919    1.5984   -5.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
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 40 70  1  0
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 41 73  1  0
M  END


  Mrv1652309092208162D          

 43 48  0  0  1  0            999 V2000
    5.8135    4.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3069    3.8140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6176    3.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4348    2.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110    2.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4217    1.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0979    1.0962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5913    0.4450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020   -0.3192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7192   -0.4323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299   -1.1966    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8471   -1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1577   -2.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233   -1.8478    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8339   -2.6121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061   -1.7347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1995   -2.3859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954   -0.9704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5782   -0.8573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    1.8605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2938    2.5117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8310    3.1946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2364    3.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0385    2.9656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0114    2.1410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9843    1.3165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918    1.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9112    0.3116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7290    1.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045    1.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687    1.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5156    2.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089    2.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6978    3.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2621    3.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    4.7079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625    3.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9982    4.6538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    4.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    3.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2356    2.4216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0065    3.2141    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  6  0  0  0
  8 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22  5  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  2  0  0  0  0
 33 41  1  0  0  0  0
 30 42  1  0  0  0  0
 26 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0280468

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]2[C@@H]1[C@@H]1O[C@@H]1[C@]21OC(=O)\C([C@H]1O)=C(/C)C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O15/c1-9(10-4-5-12(30)13(6-10)37-2)15-22(34)28(43-25(15)36)17-16(21-23(28)41-21)11(24(35)38-3)8-39-26(17)42-27-20(33)19(32)18(31)14(7-29)40-27/h4-6,8,14,16-23,26-27,29-34H,7H2,1-3H3/b15-9+/t14-,16+,17-,18-,19+,20-,21-,22+,23-,26-,27-,28-/m0/s1

> <INCHI_KEY>
SJCFCUVFNPSCIP-ZKMOGSMTSA-N

> <FORMULA>
C28H32O15

> <MOLECULAR_WEIGHT>
608.549

> <EXACT_MASS>
608.17412033

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
58.16380268995785

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1'S,2S,2'S,3R,4E,4'S,6'R,7'S)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

> <JCHEM_LOGP>
-1.0523501426666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.142992774119536

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.772251062265962

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601929886

> <JCHEM_POLAR_SURFACE_AREA>
223.42999999999998

> <JCHEM_REFRACTIVITY>
137.79429999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'S,2S,2'S,3R,4E,4'S,6'R,7'S)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      10.852   8.335   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.906   7.119   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.486   5.693   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.012   5.482   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.541   4.477   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.120   3.051   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.175   1.835   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.649   2.046   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.704   0.831   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.284  -0.596   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.809  -0.807   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.389  -2.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.915  -2.445   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.494  -3.871   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.443  -3.449   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.023  -4.876   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.918  -3.238   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.972  -4.454   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.338  -1.811   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.813  -1.600   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.070   3.473   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.015   4.688   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.151   5.963   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.041   7.031   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.672   5.536   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.621   3.997   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.571   2.457   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.091   2.030   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.568   0.582   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.228   3.305   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.688   3.355   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.875   2.048   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.962   4.713   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.577   4.764   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.303   6.122   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.489   7.430   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.215   8.788   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.050   7.379   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.863   8.687   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.403   8.637   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.776   6.021   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.173   4.520   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.745   6.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   26                                                  
CONECT   22   21    5   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   25                                                       
CONECT   25   24   23   26                                                  
CONECT   26   25   21   27   42                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   42                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   41                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   33                                                       
CONECT   42   30   26   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1's,2S,2's,3R,4E,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0,]decan]-9'-ene-10'-carboxylic acid	Generator

Chemical Formula

C₂₈H₃₂O₁₅

Average Mass

608.5490 Da

Monoisotopic Mass

608.17412 Da

IUPAC Name

methyl (1'S,2S,2'S,3R,4E,4'S,6'R,7'S)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0^{2,4}]decan]-9'-ene-10'-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]2[C@@H]1[C@@H]1O[C@@H]1[C@]21OC(=O)\C([C@H]1O)=C(/C)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C28H32O15/c1-9(10-4-5-12(30)13(6-10)37-2)15-22(34)28(43-25(15)36)17-16(21-23(28)41-21)11(24(35)38-3)8-39-26(17)42-27-20(33)19(32)18(31)14(7-29)40-27/h4-6,8,14,16-23,26-27,29-34H,7H2,1-3H3/b15-9+/t14-,16+,17-,18-,19+,20-,21-,22+,23-,26-,27-,28-/m0/s1

InChI Key

SJCFCUVFNPSCIP-ZKMOGSMTSA-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
Morinda coreia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Terpene lactone
Glycosyl compound
O-glycosyl compound
Aromatic monoterpenoid
Methoxyphenol
Monoterpenoid
Phenylpropene
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Methyl ester
Vinylogous ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Lactone
Polyol
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Oxacycle
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	-1.1	ChemAxon
pKa (Strongest Acidic)	9.77	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	223.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.79 m³·mol⁻¹	ChemAxon
Polarizability	58.16 Å³	ChemAxon
Number of Rings	6	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

163189373

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate (NP0280468)

MOL for NP0280468 (methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

3D MOL for NP0280468 (methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

3D SDF for NP0280468 (methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

3D-SDF for NP0280468 (methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

PDB for NP0280468 (methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

3D PDB for NP0280468 (methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

SMILES for NP0280468 (methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

INCHI for NP0280468 (methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

Structure for NP0280468 (methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)

3D Structure for NP0280468 (methyl (1's,2s,2's,3r,4e,4's,6'r,7's)-3-hydroxy-4-[1-(4-hydroxy-3-methoxyphenyl)ethylidene]-5-oxo-7'-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3',8'-dioxaspiro[oxolane-2,5'-tricyclo[4.4.0.0²,⁴]decan]-9'-ene-10'-carboxylate)