NP-MRD: Showing NP-Card for (1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid (NP0227405)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 06:42:55 UTC

Updated at

2022-09-06 06:42:55 UTC

NP-MRD ID

NP0227405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid

Description

CHEMBL3342216 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. (1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid is found in Brucea javanica. Based on a literature review very few articles have been published on CHEMBL3342216.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062208422D          

 36 40  0  0  1  0            999 V2000
   -2.5733    3.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554    3.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4404    3.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2526    2.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    2.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1197    3.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681    1.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8859    2.1006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2319    2.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719    3.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0553    2.8813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044    2.1874    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3237    2.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680    1.7463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6821    1.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9738    2.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2046    1.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0188    1.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130    0.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4355   -0.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0988    0.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5763    0.9746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2756    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7552    0.8600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5884    0.0576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2027   -0.4931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8133   -0.1941    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5880   -0.9877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706    0.4454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7748   -0.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0441   -0.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0980   -0.9731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543    0.7672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9811    1.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0807    1.4337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4803    1.3961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  1  0  0  0
 12 35  1  0  0  0  0
 24 35  1  1  0  0  0
 36 35  1  6  0  0  0
  8 36  1  0  0  0  0
 29 36  1  0  0  0  0
M  END

     RDKit          2D

 66 70  0  0  0  0  0  0  0  0999 V2000
   -8.6834    1.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2926    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0838   -0.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1106    1.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7198    1.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5110   -0.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378    2.3156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1470    1.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351    3.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9499    4.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4086    3.6844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    2.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1328    3.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    2.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6741    2.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9859    4.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7888    1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2154    2.0639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4769    0.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916   -0.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0503   -0.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9356    0.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237   -0.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5090    0.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2664   -1.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663   -1.2523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1369   -1.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6287   -3.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -1.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6161   -1.0216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0890   -3.1235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -1.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0741    2.1544    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2453    0.2017    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1215    2.9832    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8751   -1.9403    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5692   -0.6636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5984   -0.2461    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3193    3.4394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0910    0.5880    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    4.1750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5952    4.5447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    4.3263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5593    3.6078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978    5.5385    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4531    3.7595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378    4.7290    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3301    1.0602    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9107   -1.5590    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120   -1.7649    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930   -2.2882    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8817   -1.6109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259   -1.6968    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7438   -1.2717    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -2.7673    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319   -2.5422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0038   -3.0245    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1055   -4.3983    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3025   -4.0051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147    1.2436    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2600   -1.1321    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3180   -0.0226    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8 36  1  0
 36 35  1  0
 35 34  1  1
 34 33  1  0
 33 29  1  0
 29 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 24  1  0
 24 22  1  0
 22 23  1  1
 22 21  1  0
 21 19  1  0
 19 20  2  0
 19 17  1  0
 17 18  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
 29 30  1  6
 30 32  1  0
 30 31  2  0
  9  8  1  0
 29 36  1  0
 14 22  1  0
 24 35  1  0
 12 35  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  8 44  1  6
 36 66  1  1
 34 64  1  0
 34 65  1  0
 27 61  1  1
 28 62  1  0
 25 59  1  6
 26 60  1  0
 24 58  1  6
 23 55  1  0
 23 56  1  0
 23 57  1  0
 21 53  1  0
 21 54  1  0
 18 52  1  0
 16 49  1  0
 16 50  1  0
 16 51  1  0
 14 48  1  6
 13 46  1  0
 13 47  1  0
 12 45  1  1
 32 63  1  0
M  END


  Mrv1652309062208422D          

 36 40  0  0  1  0            999 V2000
   -2.5733    3.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554    3.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4404    3.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2526    2.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    2.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1197    3.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681    1.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8859    2.1006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2319    2.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719    3.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0553    2.8813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044    2.1874    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3237    2.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680    1.7463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6821    1.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9738    2.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2046    1.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0188    1.3744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130    0.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4355   -0.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0988    0.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5763    0.9746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2756    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7552    0.8600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5884    0.0576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2027   -0.4931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8133   -0.1941    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5880   -0.9877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706    0.4454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7748   -0.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0441   -0.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0980   -0.9731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543    0.7672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9811    1.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0807    1.4337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4803    1.3961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  1  0  0  0
 12 35  1  0  0  0  0
 24 35  1  1  0  0  0
 36 35  1  6  0  0  0
  8 36  1  0  0  0  0
 29 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(=O)O[C@@H]1[C@@H]2[C@@]34CO[C@]2([C@@H](O)[C@H](O)[C@@H]3[C@@]2(C)CC(=O)C(O)=C(C)[C@@H]2C[C@H]4OC1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O11/c1-9(2)5-14(27)36-17-19-24-8-34-25(19,22(32)33)20(30)16(29)18(24)23(4)7-12(26)15(28)10(3)11(23)6-13(24)35-21(17)31/h5,11,13,16-20,28-30H,6-8H2,1-4H3,(H,32,33)/t11-,13+,16+,17+,18+,19+,20-,23-,24+,25+/m0/s1

> <INCHI_KEY>
RIYGDELXURVOBZ-HVCNMUSHSA-N

> <FORMULA>
C25H30O11

> <MOLECULAR_WEIGHT>
506.504

> <EXACT_MASS>
506.178811786

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
33.42135984638297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3R,6R,8R,13S,14R,15R,16S,17R)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-17-carboxylic acid

> <JCHEM_LOGP>
0.09240429400000033

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.713118003962425

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4618303615468196

> <JCHEM_PKA_STRONGEST_BASIC>
-3.322002943573577

> <JCHEM_POLAR_SURFACE_AREA>
176.89

> <JCHEM_REFRACTIVITY>
120.14819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,6R,8R,13S,14R,15R,16S,17R)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-17-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.803   5.756   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.277   5.958   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.689   7.381   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.338   4.737   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.812   4.940   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.224   6.363   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.127   3.719   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.654   3.921   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.299   5.303   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.441   6.581   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.837   5.378   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.675   4.083   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.204   4.411   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.220   3.260   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.740   3.509   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.284   4.949   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.715   2.317   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.235   2.566   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.171   0.876   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.146  -0.315   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.651   0.627   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.676   1.819   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.114   0.385   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.143   1.605   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.832   0.108   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.978  -0.920   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.385  -0.362   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.964  -1.844   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.372   0.831   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.446  -0.400   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.082  -0.214   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.050  -1.816   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.035   1.432   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.831   2.794   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.884   2.676   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.763   2.606   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   35                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   14   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25   35                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   33   36                                             
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   29   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   12   24   36                                             
CONECT   36   35    8   29                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₁₁

Average Mass

506.5040 Da

Monoisotopic Mass

506.17881 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CC(=O)O[C@@H]1[C@@H]2[C@@]34CO[C@]2([C@@H](O)[C@H](O)[C@@H]3[C@@]2(C)CC(=O)C(O)=C(C)[C@@H]2C[C@H]4OC1=O)C(O)=O

InChI Identifier

InChI=1S/C25H30O11/c1-9(2)5-14(27)36-17-19-24-8-34-25(19,22(32)33)20(30)16(29)18(24)23(4)7-12(26)15(28)10(3)11(23)6-13(24)35-21(17)31/h5,11,13,16-20,28-30H,6-8H2,1-4H3,(H,32,33)/t11-,13+,16+,17+,18+,19+,20-,23-,24+,25+/m0/s1

InChI Key

RIYGDELXURVOBZ-HVCNMUSHSA-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
Polycyclic triterpenoid
C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Furopyran
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Cyclohexenone
Fatty acid ester
Oxepane
Delta valerolactone
Delta_valerolactone
Pyran
Fatty acyl
Oxane
Hydroxy acid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Furan
Tetrahydrofuran
Carboxylic acid ester
Ketone
1,2-diol
Cyclic ketone
Lactone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Enol
Ether
Polyol
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen 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

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

8566916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10391474

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid (NP0227405)

MOL for NP0227405 ((1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid)

3D MOL for NP0227405 ((1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid)

3D SDF for NP0227405 ((1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid)

3D-SDF for NP0227405 ((1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid)

PDB for NP0227405 ((1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid)

3D PDB for NP0227405 ((1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid)

SMILES for NP0227405 ((1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid)

INCHI for NP0227405 ((1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid)

Structure for NP0227405 ((1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid)

3D Structure for NP0227405 ((1r,2s,3r,6r,8r,13s,14r,15r,16s,17r)-10,15,16-trihydroxy-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylic acid)