NP-MRD: Showing NP-Card for (1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione (NP0238190)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 21:32:23 UTC

Updated at

2022-09-06 21:32:23 UTC

NP-MRD ID

NP0238190

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione

Description

(1R,2R,16S,18S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]Henicosa-4(12),5(9),6,10,14-pentaene-13,17-dione belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. (1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione is found in Garcinia cantleyana. Based on a literature review very few articles have been published on (1R,2R,16S,18S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]Henicosa-4(12),5(9),6,10,14-pentaene-13,17-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062223322D          

 37 42  0  0  1  0            999 V2000
    0.1052    1.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3339    1.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    0.5617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5419    1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    0.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211    1.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7108    2.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938    1.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2178    1.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782    2.4089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9972    1.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1525    0.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8586    0.0440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710   -0.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2925   -1.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0299   -1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9119   -2.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9155   -2.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8489   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5285   -0.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7491    0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0708   -0.3218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -0.1772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9390   -0.9171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5672   -0.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6565   -1.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476   -2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1217   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8970   -1.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3087   -0.6170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1628   -1.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9897   -1.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279   -2.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -2.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5759   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -0.3476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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
 15 18  1  0  0  0  0
 14 19  2  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
  5 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
  3 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 30 36  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END

     RDKit          3D

 69 74  0  0  0  0  0  0  0  0999 V2000
   -4.1513   -4.5762   -0.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1840   -3.2259   -0.7821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0740   -2.5171   -0.4958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8622   -3.0438   -1.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7476   -2.4608   -0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5668   -3.0326   -1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7334   -4.2018   -1.5182 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7556   -2.2419   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0267   -2.7162   -0.9824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -4.0226   -1.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1096   -1.9241   -0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -0.6322   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8040    0.3118    0.1158 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2070    1.3997    0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8860    2.6743    0.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493    2.4044    1.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208    3.1910    2.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7679    3.6411   -0.0523 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532    1.1439    0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605   -0.1534   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654   -0.9466   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2922   -0.4577   -0.0847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875   -1.1718   -0.1535 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5277   -1.5232    1.2059 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6057   -2.5645    0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1282   -0.1969    1.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978    0.5649    2.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4202   -0.3866    2.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3511    0.5178    0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9822   -0.2681   -0.6694 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5033    0.6927   -1.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5181    1.6604   -2.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4263    2.9371   -1.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5163    3.8760   -2.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3048    3.4695   -0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519   -1.0913   -1.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1215   -0.7358   -1.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1851   -4.9542   -0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4962   -5.0989   -1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9767   -4.9246    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9503   -3.7867   -2.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0843   -4.3593   -1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1179   -2.2866   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9165    2.6337    0.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7953    2.9564    1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502    1.3222    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8268    4.0242    2.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2444    3.6600    1.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9903    2.4125    2.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8912    3.1551   -0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.8218    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7832   -1.8559    1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4255   -2.5517    1.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0694   -3.5569    1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8131    1.5292    1.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1380    0.0192    2.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908    0.8416    3.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2260   -0.6922    1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2082   -1.1245    3.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6431    0.5806    2.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401    0.0716   -2.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5790    1.1962   -1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3605    1.3363   -2.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160    4.8577   -2.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003    3.5116   -3.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2137    3.9795   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951    3.1393    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044    3.1854   -1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3441    4.5640   -0.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3 25  1  0
 25 24  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  6
 31 32  1  0
 32 33  2  3
 33 34  1  0
 33 35  1  0
 30 36  1  0
 36 37  2  0
 30 23  1  0
 23 22  1  1
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 14  2  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 36  3  1  0
  5 23  1  0
  4  3  1  0
 23 24  1  0
  8 21  1  0
 12 20  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 25 53  1  0
 25 54  1  0
 24 52  1  1
 27 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
 31 61  1  0
 31 62  1  0
 32 63  1  0
 34 64  1  0
 34 65  1  0
 34 66  1  0
 35 67  1  0
 35 68  1  0
 35 69  1  0
 19 51  1  0
 11 43  1  0
 10 42  1  0
  4 41  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
M  END


  Mrv1652309062223322D          

 37 42  0  0  1  0            999 V2000
    0.1052    1.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3339    1.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    0.5617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5419    1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    0.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211    1.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7108    2.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938    1.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2178    1.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782    2.4089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9972    1.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1525    0.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8586    0.0440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710   -0.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2925   -1.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0299   -1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9119   -2.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9155   -2.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8489   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5285   -0.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7491    0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0708   -0.3218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -0.1772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9390   -0.9171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5672   -0.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6565   -1.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476   -2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1217   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8970   -1.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3087   -0.6170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1628   -1.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9897   -1.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279   -2.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013   -2.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5759   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -0.3476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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
 15 18  1  0  0  0  0
 14 19  2  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
  5 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
  3 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 30 36  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0238190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]12C[C@@H]3C(C)(C)O[C@](CC=C(C)C)(C1=O)[C@@]31OC3=C4C=C(OC4=CC(O)=C3C(=O)C1=C2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O8/c1-14(2)8-9-28-24(32)27(34-7)12-16-22(31)21-17(30)11-18-15(10-20(35-18)25(3,4)33)23(21)36-29(16,28)19(13-27)26(5,6)37-28/h8,10-12,19,30,33H,9,13H2,1-7H3/t19-,27-,28-,29+/m1/s1

> <INCHI_KEY>
CDUISSFLKYDRMU-BQZVHNDTSA-N

> <FORMULA>
C29H32O8

> <MOLECULAR_WEIGHT>
508.567

> <EXACT_MASS>
508.20971799

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.238954143804996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,16S,18S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0^{2,14}.0^{2,18}.0^{4,12}.0^{5,9}]henicosa-4,6,9,11,14-pentaene-13,17-dione

> <JCHEM_LOGP>
4.129833974000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.56416317783929

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.890819538713852

> <JCHEM_PKA_STRONGEST_BASIC>
-2.835688036057533

> <JCHEM_POLAR_SURFACE_AREA>
115.43

> <JCHEM_REFRACTIVITY>
135.8253

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,16S,18S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0^{2,14}.0^{2,18}.0^{4,12}.0^{5,9}]henicosa-4,6,9,11,14-pentaene-13,17-dione

> <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       0.196   3.713   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.623   2.180   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.868   1.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.878   2.233   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.192   1.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.266   2.505   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.060   4.104   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.708   1.889   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.873   2.896   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.986   4.497   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.328   2.391   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.618   0.879   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.936   0.082   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.586  -1.418   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.746  -2.672   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.122  -1.869   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.902  -3.792   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.042  -4.138   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.051  -1.548   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.453  -0.129   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.998   0.376   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.732  -0.601   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.114  -0.331   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.620  -1.712   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.925  -0.125   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.092  -3.211   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.822  -4.711   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.094  -4.534   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.674  -2.575   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.443  -1.152   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.037  -2.525   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.581  -3.097   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.839  -4.616   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.653  -5.598   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.282  -5.151   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.075  -0.290   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.496  -0.649   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25   36                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   14   20                                                       
CONECT   20   19   12   21                                                  
CONECT   21   20    8   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    5   24   30                                             
CONECT   24   23   25   26                                                  
CONECT   25   24    3                                                       
CONECT   26   24   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30                                                       
CONECT   30   29   23   31   36                                             
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   30    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂O₈

Average Mass

508.5670 Da

Monoisotopic Mass

508.20972 Da

IUPAC Name

(1R,2R,16S,18S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0^{2,14}.0^{2,18}.0^{4,12}.0^{5,9}]henicosa-4,6,9,11,14-pentaene-13,17-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@]12C[C@@H]3C(C)(C)O[C@](CC=C(C)C)(C1=O)[C@@]31OC3=C4C=C(OC4=CC(O)=C3C(=O)C1=C2)C(C)(C)O

InChI Identifier

InChI=1S/C29H32O8/c1-14(2)8-9-28-24(32)27(34-7)12-16-22(31)21-17(30)11-18-15(10-20(35-18)25(3,4)33)23(21)36-29(16,28)19(13-27)26(5,6)37-28/h8,10-12,19,30,33H,9,13H2,1-7H3/t19-,27-,28-,29+/m1/s1

InChI Key

CDUISSFLKYDRMU-BQZVHNDTSA-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
Garcinia cantleyana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Monoterpenoid
Aromatic monoterpenoid
Benzofuran
Aryl ketone
Cyclohexenone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Oxepane
Benzenoid
Vinylogous acid
Furan
Tetrahydrofuran
Tertiary alcohol
Heteroaromatic compound
Ketone
Oxacycle
Dialkyl ether
Ether
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic alcohol
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	4.13	ChemAxon
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	115.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135.83 m³·mol⁻¹	ChemAxon
Polarizability	54.24 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

163036655

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione (NP0238190)

MOL for NP0238190 ((1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione)

3D MOL for NP0238190 ((1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione)

3D SDF for NP0238190 ((1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione)

3D-SDF for NP0238190 ((1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione)

PDB for NP0238190 ((1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione)

3D PDB for NP0238190 ((1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione)

SMILES for NP0238190 ((1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione)

INCHI for NP0238190 ((1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione)

Structure for NP0238190 ((1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione)

3D Structure for NP0238190 ((1r,2r,16s,18s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-16-methoxy-20,20-dimethyl-18-(3-methylbut-2-en-1-yl)-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,6,9,11,14-pentaene-13,17-dione)