NP-MRD: Showing NP-Card for 14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate (NP0196597)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 14:43:01 UTC

Updated at

2022-09-04 14:43:01 UTC

NP-MRD ID

NP0196597

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate

Description

14-Hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadec-4-en-16-yl acetate 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. 14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate is found in Picrasma quassioides. 14-Hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadec-4-en-16-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161501442D          

 43 47  0  0  0  0            999 V2000
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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
    3.5724    3.7125    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
    1.4289    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  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
    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
    3.5724   -1.2375    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  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
    0.0000   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100    2.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    2.7621    0.0000 O   0  0  0  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
   -2.1434   -0.4125    0.0000 O   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
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    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
  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  9 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 33 42  1  0  0  0  0
 42 43  1  0  0  0  0
M  END

     RDKit          3D

 89 93  0  0  0  0  0  0  0  0999 V2000
   -6.8715    3.0062   -1.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1308    1.8139   -1.4273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7387    1.8882   -1.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121    3.0717   -1.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536    3.2026   -0.9763 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0945    4.1858   -2.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9428    1.8832   -1.2050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4905    1.9706   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1406    0.7999   -0.3050 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4854    0.7134   -0.7539 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1737   -0.0350    0.1615 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5365   -0.1427   -0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3736    0.3746    0.8043 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0618    1.4405    0.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2712    1.0098   -0.3199 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7942    2.0645   -1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0051    1.7046   -1.8308 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2421    0.8911    0.8455 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3894    2.1655    1.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5695    0.0092    1.8753 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1688    0.7611    2.9734 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3272   -0.6708    1.3179 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7498   -1.3816    2.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326   -1.4319    0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549   -1.4748    0.3652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4227   -2.8412    0.1464 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3304   -3.7856    1.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4049   -3.2705   -1.1560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341   -2.7261    0.6800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4717   -3.9582    0.6381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7476   -4.4538    1.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6715   -1.7044   -0.0526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6519   -1.3158    0.9170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9596   -1.7682    0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9837   -1.3707    1.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3134   -2.5572   -0.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9576   -0.5752   -0.6963 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4841   -0.5368   -0.6331 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1258   -0.9153   -2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6712    0.7599   -0.4956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9815    1.0686    0.9205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439    0.6778   -1.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3172   -0.3313   -1.8655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9558    2.7662   -1.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5884    3.7034   -2.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7102    3.4268   -0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7195    3.9564   -1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3763    3.6881   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1959    3.6967   -2.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0337    4.3470   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6933    5.1113   -1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0464    1.7059   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1008    2.2380   -1.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3217    2.8506   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    0.9161    0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186    0.4666    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202    0.7873    1.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1587    0.0667   -0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9973    3.0040   -0.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0826    2.2357   -2.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4293    0.9318   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2057    0.4724    0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5553    2.6973    1.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2490   -0.8114    2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3035    0.4357    3.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5674   -1.3860    0.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3428   -2.0735    2.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206   -2.1712   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9906   -1.7695    1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701   -1.1308    1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4113   -3.7620    0.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315   -4.8113    1.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417   -3.3395    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3464   -3.9053   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208   -2.4775    1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4188   -3.6977    2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3028   -5.3890    1.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8585   -4.5306    2.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2492   -2.3428   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6761   -0.5639    2.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2539   -2.2979    2.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9094   -1.1285    1.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774   -0.7311   -1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6681   -1.4309   -2.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888   -0.0051   -2.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885   -1.5618   -1.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326    0.4938    1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7778    2.1463    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0595    0.9572    1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 29  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 32 37  1  0
 37 38  1  0
 38 39  1  6
 38  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 42  1  0
 42 43  2  0
 42 40  1  0
 40 41  1  1
  9 10  1  0
 10 11  1  0
 11 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  6
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 26 29  1  0
 22 13  1  0
 40 37  1  0
 25 38  1  0
 40  7  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 29 75  1  1
 32 79  1  6
 35 80  1  0
 35 81  1  0
 35 82  1  0
 37 83  1  6
 39 84  1  0
 39 85  1  0
 39 86  1  0
  9 55  1  1
  8 53  1  0
  8 54  1  0
  7 52  1  6
  5 48  1  1
  6 49  1  0
  6 50  1  0
  6 51  1  0
  4 47  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
 41 87  1  0
 41 88  1  0
 41 89  1  0
 11 56  1  1
 24 68  1  0
 24 69  1  0
 25 70  1  1
 27 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 13 57  1  1
 15 58  1  6
 16 59  1  0
 16 60  1  0
 17 61  1  0
 18 62  1  6
 19 63  1  0
 20 64  1  1
 21 65  1  0
 22 66  1  6
 23 67  1  0
M  END


  Mrv1533004161501442D          

 43 47  0  0  0  0            999 V2000
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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
    3.5724    3.7125    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
    1.4289    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  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
    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
    3.5724   -1.2375    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  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
    0.0000   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100    2.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    2.7621    0.0000 O   0  0  0  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
   -2.1434   -0.4125    0.0000 O   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
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    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
  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  9 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 33 42  1  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196597

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(OC(C)=O)C2C3(C)C(CC4C(C)C=C(OC)C(=O)C24C)OC(CC3C1(C)O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O13/c1-12-8-15(38-6)25(36)28(3)14(12)9-18-29(4)17(30(5,37)26(39-7)23(24(28)29)40-13(2)32)10-19(42-18)43-27-22(35)21(34)20(33)16(11-31)41-27/h8,12,14,16-24,26-27,31,33-35,37H,9-11H2,1-7H3

> <INCHI_KEY>
RVSPJJOFLXFFDA-UHFFFAOYSA-N

> <FORMULA>
C30H46O13

> <MOLECULAR_WEIGHT>
614.685

> <EXACT_MASS>
614.293841541

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
63.602551837152376

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate

> <ALOGPS_LOGP>
0.33

> <JCHEM_LOGP>
-0.6756146993333342

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.097464465436833

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.19392135230811

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847573125177

> <JCHEM_POLAR_SURFACE_AREA>
190.67

> <JCHEM_REFRACTIVITY>
148.02060000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.205   3.904   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.518   5.156   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   23                                                  
CONECT   10    9   11   12   28                                             
CONECT   11   10                                                            
CONECT   12   10   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    9   14   24                                             
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   10   29                                                  
CONECT   29   28    3   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26   33                                                       
CONECT   33   32   34   42                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   33   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
14-Hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0,.0,]heptadec-4-en-16-yl acetic acid	Generator
14-Hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetic acid	Generator

Chemical Formula

C₃₀H₄₆O₁₃

Average Mass

614.6850 Da

Monoisotopic Mass

614.29384 Da

IUPAC Name

14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate

Traditional Name

14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate

CAS Registry Number

Not Available

SMILES

COC1C(OC(C)=O)C2C3(C)C(CC4C(C)C=C(OC)C(=O)C24C)OC(CC3C1(C)O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C30H46O13/c1-12-8-15(38-6)25(36)28(3)14(12)9-18-29(4)17(30(5,37)26(39-7)23(24(28)29)40-13(2)32)10-19(42-18)43-27-22(35)21(34)20(33)16(11-31)41-27/h8,12,14,16-24,26-27,31,33-35,37H,9-11H2,1-7H3

InChI Key

RVSPJJOFLXFFDA-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 quassioides	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
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Naphthalene
Cyclohexenone
Monosaccharide
Oxane
Pyran
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Polyol
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Acetal
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.33	ALOGPS
logP	-0.68	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	190.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	148.02 m³·mol⁻¹	ChemAxon
Polarizability	63.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

177199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate (NP0196597)

MOL for NP0196597 (14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

3D MOL for NP0196597 (14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

3D SDF for NP0196597 (14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

3D-SDF for NP0196597 (14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

PDB for NP0196597 (14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

3D PDB for NP0196597 (14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

SMILES for NP0196597 (14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

INCHI for NP0196597 (14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

Structure for NP0196597 (14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

3D Structure for NP0196597 (14-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-11-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)