NP-MRD: Showing NP-Card for 4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate (NP0283882)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 11:20:07 UTC

Updated at

2022-09-09 11:20:07 UTC

NP-MRD ID

NP0283882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate

Description

4-Hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadecan-16-yl 2H-1,3-benzodioxole-5-carboxylate 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. 4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate is found in Picrasma javanica. Based on a literature review very few articles have been published on 4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadecan-16-yl 2H-1,3-benzodioxole-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092213202D          

 37 42  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004   -3.8701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9853   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004   -5.2049    0.0000 O   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
    2.1434   -2.0625    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  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
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 22 36  1  0  0  0  0
 11 36  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

 71 76  0  0  0  0  0  0  0  0999 V2000
    1.7995   -2.4195   -2.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832   -1.9670   -1.6192 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2414   -2.2737   -0.3439 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1108   -1.0846    0.6053 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2853   -0.3676    0.3473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3980   -0.4140    1.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -1.1612    2.1967 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151    0.3061    0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6812    0.2047    1.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8671    0.9013    1.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9966    1.7160    0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9298    1.8309   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7585    1.1233   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3373    2.7035   -1.4141 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7084    2.9671   -1.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0263    2.5260   -0.0200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1795   -0.3769    0.5993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1183    1.1273    0.5280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0390    1.5500    1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6717    1.7107   -0.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415    1.0687   -1.4689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0285    3.0738   -1.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7532    3.1063   -2.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8312    3.8242   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9254    2.9066    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4144    1.6836    1.0491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4816    0.7127    1.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6076   -0.4873    0.4742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2418   -1.4504    1.3344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6332   -2.6422    1.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3872   -3.1381    2.7203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768   -3.3208    0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615   -2.4500   -0.3815 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9344   -3.1162   -0.1027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7773   -4.4006   -0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299   -0.9902   -0.1680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4588   -0.4128   -1.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6225   -1.9911   -1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8969   -3.4993   -2.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733   -1.9706   -3.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1345   -2.8712    0.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3100   -1.6009    1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5676   -0.4401    2.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7060    0.8239    2.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197    1.2093   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8870    4.0592   -1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3052    2.4384   -2.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5589   -0.4862    1.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4607    2.4312    2.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906    0.7926    2.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8490    1.9639    1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1334    3.7131   -1.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409    3.4704   -2.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    4.6934   -0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1984    4.1814    0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6401    3.4543    0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932    2.5796   -0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    2.1909    2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4603    1.2837    1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4772    0.4404    2.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4292   -0.3137   -0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111   -3.4573   -0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9183   -4.3155    0.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368   -2.7395   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9327   -3.4414    0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891   -5.1062   -0.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3907   -4.1807   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600   -4.8607   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650    0.6424   -1.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -0.8005   -2.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571   -0.8629   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 34  1  0
 34 35  1  0
 34 33  1  0
 33 32  1  0
 32 30  1  0
 30 31  2  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  1  0
 22 20  1  0
 20 21  2  0
 20 18  1  0
 18 19  1  1
 18 17  1  0
 17  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
 17 36  1  0
 36 37  1  6
  4  3  1  0
 13  8  1  0
 36 33  1  0
 36 28  1  0
 18 26  1  0
 12 11  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  1
 34 65  1  1
 35 66  1  0
 35 67  1  0
 35 68  1  0
 33 64  1  6
 32 62  1  0
 32 63  1  0
 28 61  1  6
 27 59  1  0
 27 60  1  0
 26 58  1  1
 25 56  1  0
 25 57  1  0
 24 54  1  0
 24 55  1  0
 22 52  1  6
 23 53  1  0
 19 49  1  0
 19 50  1  0
 19 51  1  0
 17 48  1  1
  4 42  1  1
  9 43  1  0
 10 44  1  0
 15 46  1  0
 15 47  1  0
 13 45  1  0
 37 69  1  0
 37 70  1  0
 37 71  1  0
M  END


  Mrv1652309092213202D          

 37 42  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004   -3.8701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9853   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004   -5.2049    0.0000 O   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
    2.1434   -2.0625    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  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
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 22 36  1  0  0  0  0
 11 36  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(C)C2CC(=O)OC3CC4CCC(O)C(=O)C4(C)C(C1OC(=O)C1=CC=C4OCOC4=C1)C23C

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O9/c1-13-16-11-21(30)36-20-10-15-6-7-17(29)25(31)27(15,2)24(28(16,20)3)23(22(13)33-4)37-26(32)14-5-8-18-19(9-14)35-12-34-18/h5,8-9,13,15-17,20,22-24,29H,6-7,10-12H2,1-4H3

> <INCHI_KEY>
LTWXTBMMHUDLGU-UHFFFAOYSA-N

> <FORMULA>
C28H34O9

> <MOLECULAR_WEIGHT>
514.571

> <EXACT_MASS>
514.220282675

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
53.20897101052757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-16-yl 2H-1,3-benzodioxole-5-carboxylate

> <JCHEM_LOGP>
3.316026484333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.392402867823218

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5019629856141243

> <JCHEM_POLAR_SURFACE_AREA>
117.59000000000002

> <JCHEM_REFRACTIVITY>
128.33960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-16-yl 2H-1,3-benzodioxole-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.134  -7.224   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      13.039  -8.470   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.134  -9.716   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   36                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   36                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   36                                                  
CONECT   23   22    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   27                                                       
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   22   11    6   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0,.0,]heptadecan-16-yl 2H-1,3-benzodioxole-5-carboxylic acid	Generator

Chemical Formula

C₂₈H₃₄O₉

Average Mass

514.5710 Da

Monoisotopic Mass

514.22028 Da

IUPAC Name

4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-16-yl 2H-1,3-benzodioxole-5-carboxylate

Traditional Name

4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-16-yl 2H-1,3-benzodioxole-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC1C(C)C2CC(=O)OC3CC4CCC(O)C(=O)C4(C)C(C1OC(=O)C1=CC=C4OCOC4=C1)C23C

InChI Identifier

InChI=1S/C28H34O9/c1-13-16-11-21(30)36-20-10-15-6-7-17(29)25(31)27(15,2)24(28(16,20)3)23(22(13)33-4)37-26(32)14-5-8-18-19(9-14)35-12-34-18/h5,8-9,13,15-17,20,22-24,29H,6-7,10-12H2,1-4H3

InChI Key

LTWXTBMMHUDLGU-UHFFFAOYSA-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
Picrasma 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

Quassinoid
Naphthopyran
Naphthalene
Benzodioxole
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Benzenoid
Pyran
Oxane
Cyclic alcohol
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Ether
Oxacycle
Dialkyl ether
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.32	ChemAxon
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	117.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	128.34 m³·mol⁻¹	ChemAxon
Polarizability	53.21 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163192406

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate (NP0283882)

MOL for NP0283882 (4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate)

3D MOL for NP0283882 (4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate)

3D SDF for NP0283882 (4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate)

3D-SDF for NP0283882 (4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate)

PDB for NP0283882 (4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate)

3D PDB for NP0283882 (4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate)

SMILES for NP0283882 (4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate)

INCHI for NP0283882 (4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate)

Structure for NP0283882 (4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate)

3D Structure for NP0283882 (4-hydroxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-16-yl 2h-1,3-benzodioxole-5-carboxylate)