NP-MRD: Showing NP-Card for [3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid (NP0059607)

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Record Information

Version

2.0

Created at

2022-04-28 04:50:03 UTC

Updated at

2022-04-28 04:50:03 UTC

NP-MRD ID

NP0059607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid

Description

(1S,2S,4R,5R,6R,7S,9R,12S)-7-(acetyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-12-yl pyridine-3-carboxylate belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). [3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid is found in Orthosphenia mexicana. Based on a literature review very few articles have been published on (1S,2S,4R,5R,6R,7S,9R,12S)-7-(acetyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-12-yl pyridine-3-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206502D          

 42 46  0  0  1  0            999 V2000
    1.1500    0.6634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5568    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4112    1.4682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8267    0.7055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4150   -0.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9585   -0.7318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7894   -0.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    0.1004    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6582    0.7789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5751    1.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731    1.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1637    0.6456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0092    1.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8444    2.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0880    2.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5273    3.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7709    4.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5753    4.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1361    3.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8925    3.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357   -0.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6863   -1.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1554   -1.6069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071   -0.6302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9577   -0.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5014   -0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554   -0.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099    0.3253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1186    1.0960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928    2.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1124    2.8511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740    2.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285    2.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763    3.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357    2.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902    1.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147    1.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817    2.4920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3663    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442    4.2957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    4.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
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 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  8 21  1  6  0  0  0
  6 22  1  1  0  0  0
  6 23  1  6  0  0  0
  5 24  1  6  0  0  0
 24 25  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5 28  1  0  0  0  0
  1 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
  4 38  1  1  0  0  0
  3 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
M  END

     RDKit          3D

 79 83  0  0  0  0  0  0  0  0999 V2000
    2.9580    2.0681   -1.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368    1.7744   -1.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779    2.6959   -1.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0996    0.4718   -1.3811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2435    0.1639   -1.1254 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8189   -0.5367   -2.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1586   -1.1586   -2.0627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7620   -0.6832   -0.7238 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9501    0.6924   -0.7077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2213    1.2152   -0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1603    0.4005   -0.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5298    2.6367   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9462    4.9681   -0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2527    5.3653   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1669    4.3649   -0.2961 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9034   -3.2744   -2.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2442   -1.6244    1.5456 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.1694   -2.1250    2.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070   -2.0778    1.9747 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8701   -3.3163    2.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5314   -1.4513    0.6354 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8249   -0.8593    0.7104 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -1.3479   -0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230   -2.2933   -0.7957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2410   -0.7501    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    0.2561    0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7586    0.8817    1.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8754    0.5102    0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0781    1.1484    0.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1633    2.1641    1.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0332    2.5456    2.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8578    1.9065    2.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4736   -0.4688    0.1765 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.3937    1.3218   -2.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9474    0.2049   -3.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8635   -1.1458   -2.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1530    5.6983   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1222   -3.2334   -2.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8473   -0.2779   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8 18  1  0
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 17 12  1  0
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 37 73  1  0
 38 74  1  0
 39 75  1  0
 40 76  1  0
 42 77  1  0
 42 78  1  0
 42 79  1  0
M  END


  Mrv1652304282206502D          

 42 46  0  0  1  0            999 V2000
    1.1500    0.6634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5568    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4112    1.4682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8267    0.7055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4150   -0.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9585   -0.7318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7894   -0.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    0.1004    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6582    0.7789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5751    1.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731    1.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1637    0.6456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0092    1.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8444    2.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0880    2.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5273    3.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7709    4.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5753    4.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1361    3.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8925    3.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357   -0.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6863   -1.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1554   -1.6069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071   -0.6302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9577   -0.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5014   -0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554   -0.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099    0.3253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1186    1.0960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928    2.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1124    2.8511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740    2.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285    2.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763    3.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357    2.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902    1.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147    1.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817    2.4920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3663    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442    4.2957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    4.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  8 21  1  6  0  0  0
  6 22  1  1  0  0  0
  6 23  1  6  0  0  0
  5 24  1  6  0  0  0
 24 25  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5 28  1  0  0  0  0
  1 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
  4 38  1  1  0  0  0
  3 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0059607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@H]2[C@H](OC(=O)C3=CC=CN=C3)[C@]3(OC2(C)C)[C@@](C)(O)C[C@@H](O)[C@H](OC(=O)\C=C\C2=CC=CC=C2)[C@@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C32H37NO9/c1-19(34)39-24-16-22-26(41-28(37)21-12-9-15-33-18-21)32(42-29(22,2)3)30(4,38)17-23(35)27(31(24,32)5)40-25(36)14-13-20-10-7-6-8-11-20/h6-15,18,22-24,26-27,35,38H,16-17H2,1-5H3/b14-13+/t22-,23-,24+,26+,27+,30+,31-,32+/m1/s1

> <INCHI_KEY>
VOPIONKNVUFWFB-ZTYMGEEKSA-N

> <FORMULA>
C32H37NO9

> <MOLECULAR_WEIGHT>
579.646

> <EXACT_MASS>
579.246831775

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
60.36322145445335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4R,5R,6R,7S,9R,12S)-7-(acetyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-12-yl pyridine-3-carboxylate

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
2.9104084243333337

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.304627283000737

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.522471796696006

> <JCHEM_PKA_STRONGEST_BASIC>
3.2398484077705585

> <JCHEM_POLAR_SURFACE_AREA>
141.48000000000002

> <JCHEM_REFRACTIVITY>
150.049

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,5R,6R,7S,9R,12S)-7-(acetyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-12-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.147   1.238   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.906   2.668   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.501   2.741   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.277   1.317   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.508  -0.140   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.522  -1.366   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.074  -1.222   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.714   0.187   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.829   1.454   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.540   1.981   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.217   2.176   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.506   1.205   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.217   3.487   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.776   3.842   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.231   5.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.184   6.443   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.639   7.914   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.141   8.256   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.187   7.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.733   5.655   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.213  -0.559   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.014  -2.964   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.890  -2.999   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.187  -1.176   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.788  -0.337   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.936  -1.736   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.103  -0.296   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.378   0.607   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.955   2.046   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.533   3.748   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.943   5.322   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.818   4.069   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.360   5.539   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.143   5.878   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.187   4.746   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      -0.728   3.275   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       0.774   2.937   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.508   2.578   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.006   4.652   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.417   6.511   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.816   8.019   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.752   8.111   0.000  0.00  0.00           C+0
CONECT    1    2   25   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5    9   38                                             
CONECT    5    4    6   24   28                                             
CONECT    6    5    7   22   23                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    8                                                            
CONECT   22    6                                                            
CONECT   23    6                                                            
CONECT   24    5   25                                                       
CONECT   25   24    1   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    5    1   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38    4                                                            
CONECT   39    3   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,4R,5R,6R,7S,9R,12S)-7-(Acetyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0,]dodecan-12-yl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₃₂H₃₇NO₉

Average Mass

579.6460 Da

Monoisotopic Mass

579.24683 Da

IUPAC Name

(1S,2S,4R,5R,6R,7S,9R,12S)-7-(acetyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-12-yl pyridine-3-carboxylate

Traditional Name

(1S,2S,4R,5R,6R,7S,9R,12S)-7-(acetyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-12-yl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H]2[C@H](OC(=O)C3=CC=CN=C3)[C@]3(OC2(C)C)[C@@](C)(O)C[C@@H](O)[C@H](OC(=O)\C=C\C2=CC=CC=C2)[C@@]13C

InChI Identifier

InChI=1S/C32H37NO9/c1-19(34)39-24-16-22-26(41-28(37)21-12-9-15-33-18-21)32(42-29(22,2)3)30(4,38)17-23(35)27(31(24,32)5)40-25(36)14-13-20-10-7-6-8-11-20/h6-15,18,22-24,26-27,35,38H,16-17H2,1-5H3/b14-13+/t22-,23-,24+,26+,27+,30+,31-,32+/m1/s1

InChI Key

VOPIONKNVUFWFB-ZTYMGEEKSA-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
Orthosphenia mexicana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Cinnamic acid ester
Cinnamic acid or derivatives
Tricarboxylic acid or derivatives
Pyridine carboxylic acid or derivatives
Pyridine carboxylic acid
Styrene
Oxepane
Fatty acid ester
Fatty acyl
Benzenoid
Pyridine
Monocyclic benzene moiety
Cyclitol or derivatives
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	3.39	ALOGPS
logP	2.91	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.52	ChemAxon
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	141.48 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	150.05 m³·mol⁻¹	ChemAxon
Polarizability	60.36 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

162856321

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for [3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid (NP0059607)

MOL for NP0059607 ([3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid)

3D MOL for NP0059607 ([3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid)

3D SDF for NP0059607 ([3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid)

3D-SDF for NP0059607 ([3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid)

PDB for NP0059607 ([3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid)

3D PDB for NP0059607 ([3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid)

SMILES for NP0059607 ([3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid)

INCHI for NP0059607 ([3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid)

Structure for NP0059607 ([3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid)

3D Structure for NP0059607 ([3R-[3alpha,5beta,5aalpha,6alpha(E),7beta,9beta,9aalpha,10R*]]-5-(Acetyloxy)octahydro-7,9-dihydroxy-2,2,5a,9-tetramethyl-6-[(1-oxo-3-phenyl-2-propenyl)oxy]-2H-3,9a-methano-1-benzoxepin-10-yl ester 3-pyridinecarboxylic acid)