NP-MRD: Showing NP-Card for (1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione (NP0312899)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 10:04:07 UTC

Updated at

2022-09-11 10:04:07 UTC

NP-MRD ID

NP0312899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione

Description

(1S,4R,5R,6S,7S,8R,11R,13S,17S,18S,19R)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]Nonadec-14-ene-9,16-dione 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. (1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione is found in Hannoa klaineana and Quassia undulata. Based on a literature review very few articles have been published on (1S,4R,5R,6S,7S,8R,11R,13S,17S,18S,19R)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]Nonadec-14-ene-9,16-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112212042D          

 40 45  0  0  1  0            999 V2000
    4.2776   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -1.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -1.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0153   -0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7343    0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3055    0.1285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3148    0.9535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5864   -0.2759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5582    0.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771   -1.1009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8441   -1.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -1.0237    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4748   -1.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244   -1.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468   -1.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -0.3668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0647    0.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -0.4458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7097   -1.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003   -1.7208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3547   -2.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6186   -2.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365   -1.3485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8271   -1.7998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821   -0.5247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9182   -0.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4915   -0.0734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5371    0.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.0815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1919    0.8811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4050    1.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260    1.9341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7938    1.4306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6710    2.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5522    1.0725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7312    1.8778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3374    1.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2504    0.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228   -0.1622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7540    0.1200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10  2  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 39 38  1  6  0  0  0
 29 39  1  1  0  0  0
 12 39  1  0  0  0  0
 40 39  1  6  0  0  0
  8 40  1  0  0  0  0
 35 40  1  0  0  0  0
M  END

     RDKit          3D

 76 81  0  0  0  0  0  0  0  0999 V2000
   -4.6731   -2.6356    2.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377   -2.2114    0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9762   -2.5729   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4956   -2.1272   -1.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -2.8012   -2.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6942   -0.8914   -1.5979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4029   -0.0243   -2.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3265   -0.2552   -0.2487 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5413    0.4516    0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0383   -1.4179    0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3377   -0.9728    1.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852   -0.4490    1.4815 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4819   -1.5133    0.6542 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2653   -1.1177   -0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849   -1.7284   -1.5391 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602    0.1427   -0.2115 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8834   -0.2124    0.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2031   -0.2874    0.5518 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7688   -1.5493    0.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8894   -1.6071   -0.0948 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5026   -2.9810   -0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9090   -3.3944    1.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9426   -0.6005    0.2940 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8490   -0.5144   -0.7644 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3832    0.7698    0.5261 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3328    1.5390    1.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0778    0.6949    1.2972 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4992    1.9529    1.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424    1.2921    0.0972 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0299    2.3597   -0.8955 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8734    2.1805   -2.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5692    1.0514   -2.8739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271    2.7585   -1.3840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5168    2.4646   -2.7566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830    2.0881   -0.6797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6100    2.2843   -1.4280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537    2.6448    0.5913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700    1.9097    1.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1888    0.7568    0.6424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1365    0.6092   -0.4847 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4706   -1.8404    3.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820   -3.5920    2.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7635   -2.8366    2.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8561   -3.1519    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7174   -1.2069   -2.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1984   -0.2918   -3.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2095    0.7958   -0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1865   -0.3018    0.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3716    1.2458    0.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3182   -2.0788    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1494   -1.9071    2.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9023   -0.3079    2.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064   -0.2272    2.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7324    0.2609   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085   -0.0455   -0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5397   -1.3403   -1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3988   -2.9214   -0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8184   -3.7166   -0.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1060   -3.6684    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5242   -0.9697    1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2348    0.3976   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1484    1.2317   -0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3537    1.3738    2.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3038    0.2518    2.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427    2.2979    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5937    1.7259    1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4800    3.3142   -0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6016    3.0616   -2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9499    2.3069   -1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4153    1.2377   -3.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220    3.8498   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    3.2529   -3.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5711    3.1817   -1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535    2.6075    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3032    1.6123    2.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6206    0.3127   -1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  1
  8 40  1  0
 40 35  1  0
 35 36  1  6
 35 37  1  0
 37 38  1  0
 39 38  1  1
 39 12  1  0
 12 11  1  0
 11 10  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 16 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  1  0
 10  2  1  0
 27 18  1  0
 10  8  1  0
 39 40  1  0
 29 39  1  0
 33 35  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  3 44  1  0
  6 45  1  6
  7 46  1  0
  9 47  1  0
  9 48  1  0
  9 49  1  0
 40 76  1  6
 36 73  1  0
 38 74  1  0
 38 75  1  0
 12 53  1  1
 11 51  1  0
 11 52  1  0
 10 50  1  6
 16 54  1  6
 18 55  1  6
 20 56  1  6
 21 57  1  0
 21 58  1  0
 22 59  1  0
 23 60  1  1
 24 61  1  0
 25 62  1  6
 26 63  1  0
 27 64  1  1
 28 65  1  0
 29 66  1  1
 30 67  1  1
 31 68  1  0
 31 69  1  0
 32 70  1  0
 33 71  1  6
 34 72  1  0
M  END


  Mrv1652309112212042D          

 40 45  0  0  1  0            999 V2000
    4.2776   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -1.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -1.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0153   -0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7343    0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3055    0.1285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3148    0.9535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5864   -0.2759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5582    0.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771   -1.1009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8441   -1.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -1.0237    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4748   -1.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244   -1.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468   -1.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -0.3668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0647    0.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -0.4458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7097   -1.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003   -1.7208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3547   -2.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6186   -2.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365   -1.3485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8271   -1.7998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821   -0.5247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9182   -0.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4915   -0.0734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5371    0.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.0815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1919    0.8811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4050    1.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260    1.9341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7938    1.4306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6710    2.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5522    1.0725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7312    1.8778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3374    1.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2504    0.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228   -0.1622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7540    0.1200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10  2  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 39 38  1  6  0  0  0
 29 39  1  1  0  0  0
 12 39  1  0  0  0  0
 40 39  1  6  0  0  0
  8 40  1  0  0  0  0
 35 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312899

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)[C@@H](O)[C@]2(C)[C@H]3[C@@]4(O)OC[C@@]33[C@@H](C[C@@H]12)OC(=O)[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H]3[C@@H](CO)[C@H]4O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O14/c1-8-3-11(29)20(34)24(2)10(8)4-13-25-7-37-26(36,23(24)25)19(33)9(5-27)14(25)18(21(35)39-13)40-22-17(32)16(31)15(30)12(6-28)38-22/h3,9-10,12-20,22-23,27-28,30-34,36H,4-7H2,1-2H3/t9-,10+,12-,13-,14-,15-,16+,17-,18-,19-,20-,22+,23-,24-,25+,26+/m1/s1

> <INCHI_KEY>
SYVOZHUKDPLDTP-AHHZTHGVSA-N

> <FORMULA>
C26H36O14

> <MOLECULAR_WEIGHT>
572.56

> <EXACT_MASS>
572.210505839

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.52758922216586

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,5R,6S,7S,8R,11R,13S,17S,18S,19R)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0^{1,7}.0^{4,19}.0^{13,18}]nonadec-14-ene-9,16-dione

> <JCHEM_LOGP>
-3.942647563333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.14518379553296

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.867613583084895

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6392160816659382

> <JCHEM_POLAR_SURFACE_AREA>
232.89999999999995

> <JCHEM_REFRACTIVITY>
128.61450000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5R,6S,7S,8R,11R,13S,17S,18S,19R)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0^{1,7}.0^{4,19}.0^{13,18}]nonadec-14-ene-9,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       7.985  -4.380   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -2.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.344  -2.085   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.362  -0.545   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.704   0.210   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.037   0.240   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.054   1.780   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.695  -0.515   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.642   1.024   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.677  -2.055   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.309  -2.744   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.010  -1.911   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.753  -2.841   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.352  -2.213   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.087  -3.091   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.253  -0.685   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.121   0.010   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.410  -0.832   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.325  -2.370   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.614  -3.212   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.529  -4.750   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.155  -5.445   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.988  -2.517   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.277  -3.360   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.073  -0.979   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.447  -0.284   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.784  -0.137   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.869   1.401   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.560   0.152   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.225   1.645   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.756   2.107   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.422   3.610   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.348   2.670   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.119   4.193   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.764   2.002   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.098   3.505   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.230   2.007   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.067   0.438   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.149  -0.303   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.141   0.224   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   40                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   39                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16   30   39                                                  
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37   40                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   29   12   40                                             
CONECT   40   39    8   35                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₁₄

Average Mass

572.5600 Da

Monoisotopic Mass

572.21051 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)[C@@H](O)[C@]2(C)[C@H]3[C@@]4(O)OC[C@@]33[C@@H](C[C@@H]12)OC(=O)[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H]3[C@@H](CO)[C@H]4O

InChI Identifier

InChI=1S/C26H36O14/c1-8-3-11(29)20(34)24(2)10(8)4-13-25-7-37-26(36,23(24)25)19(33)9(5-27)14(25)18(21(35)39-13)40-22-17(32)16(31)15(30)12(6-28)38-22/h3,9-10,12-20,22-23,27-28,30-34,36H,4-7H2,1-2H3/t9-,10+,12-,13-,14-,15-,16+,17-,18-,19-,20-,22+,23-,24-,25+,26+/m1/s1

InChI Key

SYVOZHUKDPLDTP-AHHZTHGVSA-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
Hannoa klaineana	LOTUS Database	35616633
Quassia undulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

Triterpenoid
C-20 quassinoid skeleton
Quassinoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Naphthopyran
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Naphthalene
Delta valerolactone
Cyclohexenone
Delta_valerolactone
Oxepane
Fatty acyl
Monosaccharide
Oxane
Pyran
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Ketone
Cyclic ketone
Lactone
Polyol
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

162984014

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione (NP0312899)

MOL for NP0312899 ((1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione)

3D MOL for NP0312899 ((1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione)

3D SDF for NP0312899 ((1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione)

3D-SDF for NP0312899 ((1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione)

PDB for NP0312899 ((1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione)

3D PDB for NP0312899 ((1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione)

SMILES for NP0312899 ((1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione)

INCHI for NP0312899 ((1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione)

Structure for NP0312899 ((1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione)

3D Structure for NP0312899 ((1s,4r,5r,6s,7s,8r,11r,13s,17s,18s,19r)-4,5,17-trihydroxy-6-(hydroxymethyl)-14,18-dimethyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione)