NP-MRD: Showing NP-Card for methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate (NP0309238)

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Record Information

Version

2.0

Created at

2022-09-11 03:42:07 UTC

Updated at

2022-09-11 03:42:07 UTC

NP-MRD ID

NP0309238

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate

Description

Dehydrobruceantinol 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,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate is found in Brucea antidysenterica and Brucea javanica. Based on a literature review very few articles have been published on Dehydrobruceantinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205422D          

 43 47  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
   -2.8579    0.8250    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
   -3.1599   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.8250    0.0000 C   0  0  0  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
    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  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  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  0  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  0  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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 10 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 27 26  1  6  0  0  0
  8 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39  8  1  1  0  0  0
 39 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
  5 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END

     RDKit          3D

 79 83  0  0  0  0  0  0  0  0999 V2000
    1.7942   -4.9709   -1.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139   -4.2210   -1.3221 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4276   -3.3295   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449   -3.1559    0.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8494   -2.6040   -0.1848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7362   -2.9835   -1.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318   -1.8750   -1.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1968   -0.7813   -0.5898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7258   -1.1447   -0.4480 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1412   -0.2974    0.3171 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1212    0.2957   -0.6005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4649    0.3127   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -0.1909    0.8737 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948    0.8812   -1.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7819    0.9326   -0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2401    0.3554    0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7613    1.5614   -1.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0482    2.0941   -2.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8660    0.6119   -2.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3593    2.6423   -1.0588 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7103    3.7208   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4155    4.8384    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4745    3.8021   -0.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6577    0.9408    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341    1.4051    1.8667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3781    1.4629   -0.3593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2629    0.5954   -1.0993 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6068    1.2952   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1638    1.0242    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5158    2.0265    1.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3735    3.4421    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0401    1.8264    2.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3775    2.7863    3.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1248    0.4451    2.9567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6094    0.1615    4.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7677   -0.5200    2.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2574   -0.3809    0.8159 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3430   -1.0302   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9251   -1.0772    0.6856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9960   -2.5407    0.9248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5934   -3.2981   -0.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5312   -2.9913    1.0845 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9726   -2.4820    2.2311 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9310   -5.6096   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7066   -4.3762   -1.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4415   -2.0005   -1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -1.4872   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580   -1.1062   -1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6652   -0.6227    1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1735    1.3061   -2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9884   -0.7466    0.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    0.7984    1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657    0.3655    0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6368    1.1947   -3.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7768    2.5672   -3.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2829    2.8345   -2.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5169   -0.3585   -2.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4519    1.1399   -2.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5755    0.5146   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3188    5.7920   -0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9537    5.0612    1.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4949    4.6103    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9646    0.6848   -2.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3217    0.9065   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4816    2.3790   -1.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9302    3.5453   -0.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8135    4.1366    1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5585   -0.1764    4.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8765   -1.5348    2.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2873   -0.4950    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5242   -2.0787    0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2655   -0.7934   -1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3050   -0.6649    1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4489   -2.7386    1.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1508   -4.0440    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272   -4.1024    1.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205   -2.4707    2.9725 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  6
  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  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 10 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 34 36  2  0
 36 37  1  0
 37 38  1  6
 37 39  1  0
 39 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
  9  5  1  0
 37 29  1  0
 42  5  1  0
 27  8  1  0
 39  8  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  7 47  1  0
  7 48  1  0
  9 49  1  6
 10 50  1  1
 14 51  1  0
 16 52  1  0
 16 53  1  0
 16 54  1  0
 18 55  1  0
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 22 61  1  0
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 27 64  1  6
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 31 67  1  0
 31 68  1  0
 31 69  1  0
 35 70  1  0
 36 71  1  0
 38 72  1  0
 38 73  1  0
 38 74  1  0
 39 75  1  1
 40 76  1  1
 41 77  1  0
 42 78  1  1
 43 79  1  0
M  END


  Mrv1652309112205422D          

 43 47  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
   -2.8579    0.8250    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
   -3.1599   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.8250    0.0000 C   0  0  0  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
    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  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  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  0  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  0  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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 10 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 27 26  1  6  0  0  0
  8 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39  8  1  1  0  0  0
 39 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
  5 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0309238

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]12OC[C@@]34[C@H]1[C@@H](OC(=O)\C=C(/C)C(C)(C)OC(C)=O)C(=O)O[C@@H]3CC1=C(C)C(=O)C(O)=C[C@]1(C)[C@H]4[C@@H](O)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O13/c1-12(27(4,5)43-14(3)31)8-18(33)42-21-23-29-11-40-30(23,26(38)39-7)24(36)20(35)22(29)28(6)10-16(32)19(34)13(2)15(28)9-17(29)41-25(21)37/h8,10,17,20-24,32,35-36H,9,11H2,1-7H3/b12-8+/t17-,20-,21-,22-,23-,24+,28+,29-,30+/m1/s1

> <INCHI_KEY>
MJOFLSVJDZIFKV-UUTDASJCSA-N

> <FORMULA>
C30H36O13

> <MOLECULAR_WEIGHT>
604.605

> <EXACT_MASS>
604.215591219

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.721014068769485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2S,3R,6R,13S,14R,15R,16S,17S)-3-{[(2E)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadeca-8,11-diene-17-carboxylate

> <JCHEM_LOGP>
0.20215917933333244

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.74625096452116

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.288487302695877

> <JCHEM_PKA_STRONGEST_BASIC>
-3.330453002471182

> <JCHEM_POLAR_SURFACE_AREA>
192.18999999999997

> <JCHEM_REFRACTIVITY>
145.8023

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,3R,6R,13S,14R,15R,16S,17S)-3-{[(2E)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadeca-8,11-diene-17-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-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      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.898  -2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.438   0.564   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -9.336   0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   43  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   42                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   27   39                                             
CONECT    9    8    5   10                                                  
CONECT   10    9   11   24                                                  
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   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   10   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26    8   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   29   38   39                                             
CONECT   38   37                                                            
CONECT   39   37    8   40                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40    5   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₁₃

Average Mass

604.6050 Da

Monoisotopic Mass

604.21559 Da

IUPAC Name

methyl (1R,2S,3R,6R,13S,14R,15R,16S,17S)-3-{[(2E)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadeca-8,11-diene-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)(C)OC(C)=O)C(=O)O[C@@H]3CC1=C(C)C(=O)C(O)=C[C@]1(C)[C@H]4[C@@H](O)[C@@H]2O

InChI Identifier

InChI=1S/C30H36O13/c1-12(27(4,5)43-14(3)31)8-18(33)42-21-23-29-11-40-30(23,26(38)39-7)24(36)20(35)22(29)28(6)10-16(32)19(34)13(2)15(28)9-17(29)41-25(21)37/h8,10,17,20-24,32,35-36H,9,11H2,1-7H3/b12-8+/t17-,20-,21-,22-,23-,24+,28+,29-,30+/m1/s1

InChI Key

MJOFLSVJDZIFKV-UUTDASJCSA-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 antidysenterica	LOTUS Database	35616633
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
Quassinoid
Naphthopyranone
Naphthopyran
Tetracarboxylic acid or derivatives
Naphthalene
Furopyran
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Pyranone
Oxepane
Beta-hydroxy acid
Hydroxy acid
Oxane
Pyran
Fatty acyl
Cyclic alcohol
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Secondary alcohol
Lactone
Cyclic ketone
Ketone
Carboxylic acid ester
1,2-diol
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Enol
Ether
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.2	ChemAxon
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	192.19 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	145.8 m³·mol⁻¹	ChemAxon
Polarizability	59.72 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

32774088

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54604632

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,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate (NP0309238)

MOL for NP0309238 (methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate)

3D MOL for NP0309238 (methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate)

3D SDF for NP0309238 (methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate)

3D-SDF for NP0309238 (methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate)

PDB for NP0309238 (methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate)

3D PDB for NP0309238 (methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate)

SMILES for NP0309238 (methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate)

INCHI for NP0309238 (methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate)

Structure for NP0309238 (methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate)

3D Structure for NP0309238 (methyl (1r,2s,3r,6r,13s,14r,15r,16s,17s)-3-{[(2e)-4-(acetyloxy)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadeca-8,11-diene-17-carboxylate)