NP-MRD: Showing NP-Card for methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate (NP0251522)

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Record Information

Version

2.0

Created at

2022-09-07 14:44:31 UTC

Updated at

2022-09-07 14:44:31 UTC

NP-MRD ID

NP0251522

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate

Description

Javanicolide C belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate is found in Brucea javanica. Based on a literature review very few articles have been published on Javanicolide C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216442D          

 37 41  0  0  1  0            999 V2000
   -1.4668   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -1.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0746   -0.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8342   -0.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7065   -1.3057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8166   -0.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  9  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33  8  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
    3.4608    4.3513   -2.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542    3.8238   -1.6711 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9685    2.4517   -1.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490    1.7075   -2.1434 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131    1.9263   -1.1239 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0797    3.0399   -0.7357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0257    2.6004    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139    1.1743    0.5150 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7888    1.2045    0.1692 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4546   -0.0846    0.2547 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8466    0.1141    0.5671 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582   -0.5328   -0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5383   -1.2964   -1.0636 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2382   -0.2702    0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2391   -0.8554   -0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6539   -0.6059   -0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9691   -1.7972   -1.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296   -0.7870    1.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0914   -2.0012    1.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2540   -0.0131    2.3800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7961    0.8822    1.9627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0873    0.2791    2.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6255   -0.7744    1.4972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9428   -1.2533    2.0424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6902   -1.9874    3.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6434   -2.2263    1.1389 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9127   -3.4573    1.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7918   -2.5280   -0.0450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7768   -3.4486    0.2893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2689   -1.3483   -0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7592   -0.2225    0.0732 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7930    0.8447    0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969    0.1785   -0.3651 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2872    0.5350   -1.8243 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3241    1.3010   -2.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0112    1.2045   -2.1977 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9106    0.3000   -2.7771 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401    5.3943   -2.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846    3.7571   -3.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2313    4.3890   -1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9808    3.2312    1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0099    2.7390   -0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2353    1.9013    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -0.7594   -0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4865    0.4046    1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6507   -0.1545    1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2541   -1.5416   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1192    0.0580   -0.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9179   -2.1810   -1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4886   -1.2274   -2.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3986   -2.6912   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302    1.8145    2.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8560   -0.2649    3.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584    1.0169    2.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9182   -1.6444    1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6149   -0.4036    2.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4697   -1.2927    4.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9359   -2.7660    3.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6462   -2.4880    3.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6486   -1.8681    0.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8007   -3.4010    2.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4441   -3.0984   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761   -4.3780    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0663   -0.9527   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739   -1.7531   -1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7515    0.3186    0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6553    1.5868    0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0572    1.3388   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803   -0.7722   -0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3119   -0.4066   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    1.0557   -3.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843    1.9625   -3.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3404    0.6471   -3.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  6
  5  6  1  0
  6  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
 10 18  1  0
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 18 20  1  0
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 22 23  1  0
 23 24  1  0
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 33 34  1  0
 34 35  1  0
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 36 37  1  0
  9  5  1  0
 31 23  1  0
 36  5  1  0
 21  8  1  0
 33  8  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  7 41  1  0
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  9 43  1  1
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 29 63  1  0
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 32 66  1  0
 32 67  1  0
 32 68  1  0
 33 69  1  6
 34 70  1  6
 35 71  1  0
 36 72  1  6
 37 73  1  0
M  END


  Mrv1652309072216442D          

 37 41  0  0  1  0            999 V2000
   -1.4668   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -1.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0746   -0.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8342   -0.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7065   -1.3057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8166   -0.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  9  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33  8  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0251522

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]12OC[C@@]34[C@H]1[C@@H](OC(=O)C=C(C)C)C(=O)O[C@@H]3C[C@H]1[C@H](C)[C@H](O)[C@H](O)C[C@]1(C)[C@H]4[C@@H](O)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h6,11-14,16-21,27,29-31H,7-9H2,1-5H3/t11-,12-,13+,14+,16-,17+,18+,19+,20+,21-,24-,25+,26-/m0/s1

> <INCHI_KEY>
HGWAIHIPTWRNHL-QFWHAJIVSA-N

> <FORMULA>
C26H36O11

> <MOLECULAR_WEIGHT>
524.563

> <EXACT_MASS>
524.225761979

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.127611089830395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2S,3R,6R,8S,9S,10S,11R,13S,14R,15R,16S,17S)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadecane-17-carboxylate

> <JCHEM_LOGP>
-0.40166031233333344

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.746909283201486

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.705291340207683

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1561637386697186

> <JCHEM_POLAR_SURFACE_AREA>
169.04999999999998

> <JCHEM_REFRACTIVITY>
124.43580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,3R,6R,8S,9S,10S,11R,13S,14R,15R,16S,17S)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadecane-17-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.738  -2.462   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.265  -2.912   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.139  -1.861   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.557  -1.260   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.185  -2.437   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.391  -1.143   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.667  -4.620   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    9   36                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21   33                                             
CONECT    9    8    5   10                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   10   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    8   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   23   32   33                                             
CONECT   32   31                                                            
CONECT   33   31    8   34                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    5   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₁₁

Average Mass

524.5630 Da

Monoisotopic Mass

524.22576 Da

IUPAC Name

methyl (1R,2S,3R,6R,8S,9S,10S,11R,13S,14R,15R,16S,17S)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadecane-17-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]12OC[C@@]34[C@H]1[C@@H](OC(=O)C=C(C)C)C(=O)O[C@@H]3C[C@H]1[C@H](C)[C@H](O)[C@H](O)C[C@]1(C)[C@H]4[C@@H](O)[C@@H]2O

InChI Identifier

InChI=1S/C26H36O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h6,11-14,16-21,27,29-31H,7-9H2,1-5H3/t11-,12-,13+,14+,16-,17+,18+,19+,20+,21-,24-,25+,26-/m0/s1

InChI Key

HGWAIHIPTWRNHL-QFWHAJIVSA-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
Brucea javanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

Triterpenoid
C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Furopyran
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
Hydroxy acid
Fatty acyl
Oxane
Pyran
Tetrahydrofuran
Enoate ester
Methyl ester
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Furan
Secondary alcohol
Carboxylic acid ester
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Polyol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen 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	-0.4	ChemAxon
pKa (Strongest Acidic)	12.71	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	169.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.44 m³·mol⁻¹	ChemAxon
Polarizability	53.13 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00051028

Chemspider ID

9389687

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11214625

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate (NP0251522)

MOL for NP0251522 (methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate)

3D MOL for NP0251522 (methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate)

3D SDF for NP0251522 (methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate)

3D-SDF for NP0251522 (methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate)

PDB for NP0251522 (methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate)

3D PDB for NP0251522 (methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate)

SMILES for NP0251522 (methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate)

INCHI for NP0251522 (methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate)

Structure for NP0251522 (methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate)

3D Structure for NP0251522 (methyl (1r,2s,3r,6r,8s,9s,10s,11r,13s,14r,15r,16s,17s)-10,11,15,16-tetrahydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4-oxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadecane-17-carboxylate)