NP-MRD: Showing NP-Card for methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate (NP0174706)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 11:59:45 UTC

Updated at

2022-09-03 11:59:45 UTC

NP-MRD ID

NP0174706

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate

Description

Bruceanol A, also known as bruceanol-a, 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 (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate is found in Brucea antidysenterica. methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate was first documented in 2022 (PMID: 35895695). Based on a literature review very few articles have been published on Bruceanol A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032213592D          

 39 44  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  1  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  0  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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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   -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
    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  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
    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  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  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
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  6  0  0  0
  8 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35  8  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END

     RDKit          3D

 69 74  0  0  0  0  0  0  0  0999 V2000
    3.0422   -4.4100   -1.9647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8616   -3.7494   -1.5973 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6367   -2.3947   -1.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5464   -1.6891   -2.2253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3764   -1.7812   -1.3282 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4923   -2.7411   -0.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0924   -2.3079    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9292   -0.8025    0.2658 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5255   -0.7483   -0.2211 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5221   -1.1664    0.7860 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5560   -0.1983    0.8233 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -0.4259    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2494   -1.5897    0.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7891    0.7058    0.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3704    1.9828    0.9726 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2449    3.0478    1.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5868    2.8369    0.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0409    1.5664    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358    0.5218    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0192   -1.3444    2.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7820   -1.7842    3.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2817   -1.0427    2.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9827   -0.1728    1.6106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3732    0.0684    2.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3647    0.3676    0.9952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4484    1.1941    1.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6096    1.4618    2.9375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3092    1.7190    0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1162    1.4330   -0.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1046    1.3440   -1.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7605    1.2500   -1.2856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4393    2.4463   -1.9716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074    0.9179   -0.2602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0062    2.1758    0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8245   -0.2065   -0.7631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1903    0.0659   -2.0872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5747    1.2946   -2.2206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3220   -1.0955   -2.4752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0435   -2.0926   -3.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8989   -3.7284   -1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8633   -4.8862   -2.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228   -5.1972   -1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354   -2.8011    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -2.5924    0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7623    0.2534   -0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -2.1333    0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3143    2.1503    1.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130    4.0385    1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2882    3.6810    0.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0907    1.4085    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5466   -0.4521    0.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903    0.7890    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7189   -0.8533    2.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176    0.9104    2.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240   -0.6111    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6962    1.6039    3.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1985    0.6823    3.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1539    2.4759    3.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1431    2.3503    0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8305    0.4853   -2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315    3.1853   -1.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9504    2.2563   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840    3.0879   -0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898    2.4127    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5996   -1.0062   -1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988    0.0761   -2.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    1.2758   -3.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4671   -0.7666   -3.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3483   -2.7519   -3.4529 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  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 10 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  1
 33 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
  9  5  1  0
 19 14  1  0
 33 25  1  0
 38  5  1  0
 23  8  1  0
 35  8  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  7 43  1  0
  7 44  1  0
  9 45  1  6
 10 46  1  6
 15 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 23 52  1  6
 24 53  1  0
 24 54  1  0
 25 55  1  6
 27 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  0
 31 60  1  6
 32 61  1  0
 34 62  1  0
 34 63  1  0
 34 64  1  0
 35 65  1  6
 36 66  1  6
 37 67  1  0
 38 68  1  6
 39 69  1  0
M  END


  Mrv1652309032213592D          

 39 44  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  1  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  0  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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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   -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
    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  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
    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  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  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
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  6  0  0  0
  8 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35  8  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0174706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12OCC34[C@H]1[C@@H](OC(=O)C1=CC=CC=C1)C(=O)O[C@@H]3C[C@H]1C(C)=CC(=O)[C@@H](O)[C@]1(C)[C@H]4[C@@H](O)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O11/c1-12-9-15(29)21(31)26(2)14(12)10-16-27-11-37-28(25(35)36-3,22(32)17(30)19(26)27)20(27)18(24(34)38-16)39-23(33)13-7-5-4-6-8-13/h4-9,14,16-22,30-32H,10-11H2,1-3H3/t14-,16+,17+,18+,19+,20+,21+,22-,26-,27?,28+/m0/s1

> <INCHI_KEY>
QSNVEJIGBNLCQI-KMRSUJGASA-N

> <FORMULA>
C28H30O11

> <MOLECULAR_WEIGHT>
542.537

> <EXACT_MASS>
542.178811786

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.669070844713445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3R,6R,8S,12S,13S,14R,15R,16S,17R)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-17-carboxylate

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
0.47634940233333334

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.147428905243839

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.530897215732377

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3240344008114677

> <JCHEM_POLAR_SURFACE_AREA>
165.89000000000001

> <JCHEM_REFRACTIVITY>
130.35540000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,3R,6R,8S,12S,13S,14R,15R,16S,17R)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-17-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   39  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   38                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   23   35                                             
CONECT    9    8    5   10                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   10   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22    8   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   25   34   35                                             
CONECT   34   33                                                            
CONECT   35   33    8   36                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    5   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
Bruceanol-a	MeSH

Chemical Formula

C₂₈H₃₀O₁₁

Average Mass

542.5370 Da

Monoisotopic Mass

542.17881 Da

IUPAC Name

methyl (2S,3R,6R,8S,12S,13S,14R,15R,16S,17R)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-17-carboxylate

Traditional Name

methyl (2S,3R,6R,8S,12S,13S,14R,15R,16S,17R)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-17-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12OCC34[C@H]1[C@@H](OC(=O)C1=CC=CC=C1)C(=O)O[C@@H]3C[C@H]1C(C)=CC(=O)[C@@H](O)[C@]1(C)[C@H]4[C@@H](O)[C@@H]2O

InChI Identifier

InChI=1S/C28H30O11/c1-12-9-15(29)21(31)26(2)14(12)10-16-27-11-37-28(25(35)36-3,22(32)17(30)19(26)27)20(27)18(24(34)38-16)39-23(33)13-7-5-4-6-8-13/h4-9,14,16-22,30-32H,10-11H2,1-3H3/t14-,16+,17+,18+,19+,20+,21+,22-,26-,27?,28+/m0/s1

InChI Key

QSNVEJIGBNLCQI-KMRSUJGASA-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

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
Benzoate ester
Tricarboxylic acid or derivatives
Furopyran
Benzoic acid or derivatives
Benzoyl
Cyclohexenone
Oxepane
Delta_valerolactone
Delta valerolactone
Beta-hydroxy acid
Benzenoid
Pyran
Oxane
Hydroxy acid
Monocyclic benzene moiety
Methyl ester
Tetrahydrofuran
Furan
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	1.16	ALOGPS
logP	0.48	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.53	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.89 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.36 m³·mol⁻¹	ChemAxon
Polarizability	53.67 Å³	ChemAxon
Number of Rings	6	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

Not Available

Chemspider ID

113359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bruceanol A

METLIN ID

Not Available

PubChem Compound

127805

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bultum LE, Tolossa GB, Lee D: Combining empirical knowledge, in silico molecular docking and ADMET profiling to identify therapeutic phytochemicals from Brucea antidysentrica for acute myeloid leukemia. PLoS One. 2022 Jul 27;17(7):e0270050. doi: 10.1371/journal.pone.0270050. eCollection 2022. [PubMed:35895695 ]
LOTUS database [Link]

Showing NP-Card for methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate (NP0174706)

MOL for NP0174706 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

3D MOL for NP0174706 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

3D SDF for NP0174706 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

3D-SDF for NP0174706 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

PDB for NP0174706 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

3D PDB for NP0174706 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

SMILES for NP0174706 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

INCHI for NP0174706 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

Structure for NP0174706 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

3D Structure for NP0174706 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(benzoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)