NP-MRD: Showing NP-Card for (6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid (NP0300294)

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Record Information

Version

2.0

Created at

2022-09-10 12:37:11 UTC

Updated at

2022-09-10 12:37:11 UTC

NP-MRD ID

NP0300294

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid

Description

(6Z,9Z,17R)-17-hydroxy-N-[2-(5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid is found in Withania somnifera. Based on a literature review very few articles have been published on (6Z,9Z,17R)-17-hydroxy-N-[2-(5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102214372D          

 55 58  0  0  1  0            999 V2000
    8.7168   -5.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4312   -5.5553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4312   -4.7303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1457   -5.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8602   -5.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5747   -5.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2891   -5.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0036   -5.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7181   -5.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4325   -5.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4325   -6.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7181   -7.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0036   -6.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2891   -7.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2891   -8.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0036   -8.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7181   -8.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4325   -8.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1470   -8.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1470   -7.2053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8615   -8.4428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5760   -8.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2904   -8.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0049   -8.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0911   -7.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8981   -7.0383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3106   -7.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1176   -7.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3725   -8.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8205   -9.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0754  -10.1066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5234  -10.7197    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.7783  -11.5043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2263  -12.1174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.4812  -12.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2882  -13.0736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5431  -13.8582    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.3501  -14.0297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6051  -14.8144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.4120  -14.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6670  -15.7705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0530  -15.4275    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.3080  -16.2121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2461  -15.2559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.6940  -15.8690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9911  -14.4713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1841  -14.2998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4193  -11.9459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8673  -12.5590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1644  -11.1613    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3574  -10.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7164  -10.5482    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.4615   -9.7636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0135   -9.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7586   -8.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  4  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 39 42  1  0  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 44 45  1  6  0  0  0
 44 46  1  0  0  0  0
 37 46  1  0  0  0  0
 46 47  1  1  0  0  0
 34 48  1  0  0  0  0
 48 49  1  1  0  0  0
 48 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 32 52  1  0  0  0  0
 52 53  1  1  0  0  0
 30 54  1  0  0  0  0
 54 55  2  0  0  0  0
 24 55  1  0  0  0  0
 27 55  1  0  0  0  0
M  END

     RDKit          3D

117120  0  0  0  0  0  0  0  0999 V2000
   12.4805    1.7977    2.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3165    0.3225    2.5876 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6008   -0.3331    3.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9124   -0.0107    2.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4998    0.7097    0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4076    0.3391   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0391    1.0185   -1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6465    0.6695   -1.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4938   -0.8255   -2.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1493   -1.2009   -2.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3286   -2.0227   -1.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7238   -2.6606   -0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -2.4027    0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9841   -1.6086    0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3003   -0.7328   -0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8644   -1.2011   -0.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0671   -0.3693   -1.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6511   -0.7958   -1.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.7611   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -1.6735   -0.3553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9450   -0.0613    0.6881 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6172    0.8866    1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7412    1.9602    2.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    2.6384    0.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    3.8294    0.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5231    4.1067   -0.6132 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4503    3.1578   -0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5755    2.9455   -1.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306    1.8108   -1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539    0.8799   -0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7712   -0.2658   -0.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8952   -0.7212   -0.7197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0556   -0.5864    0.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0779   -1.1330   -0.7114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.4133   -0.5123   -0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9353   -0.5619    0.7458 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1672    0.0473    0.7275 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.2224    1.2151    1.5219 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3914    1.8735    1.0851 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.4007    3.3197    1.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2988    3.9448    0.9170 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5703    1.1084    1.6353 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.7084    1.8584    1.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6149   -0.2474    0.9647 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.6085   -0.9969    1.5587 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2614   -0.9124    1.1134 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.2229   -1.9910    0.2342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0627   -2.6195   -0.4295 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9602   -3.2551   -1.2558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6473   -3.1315   -0.5795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1041   -3.5597    0.6309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7342   -2.1391   -1.2222 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7903   -2.2174   -2.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224    1.1050    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1471    2.2236    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3713    2.3587    1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7408    2.1062    3.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4942    1.9583    3.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0192   -0.0359    1.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4251   -0.8716    3.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2341    0.2869    3.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8456   -1.1101    1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4318    0.5098    0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5554    1.8043    1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5683   -0.7398   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4214    0.7622    0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1119    2.1074   -1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7714    0.6978   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4712    1.1910   -2.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8984    1.0407   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9515   -1.3476   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1655   -1.0318   -3.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7439   -0.7728   -3.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3354   -2.2523   -2.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8340   -2.6461   -0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5643   -3.7949   -0.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3222   -2.9651    1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.5798    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1906    0.2739    0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7777   -0.4283   -1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8570   -2.2870   -0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -1.1596    0.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5477   -0.5773   -2.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2128    0.7055   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -1.8260   -1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1766   -0.1219   -2.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666   -1.5330   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2252    0.4028    2.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4400    2.6661    2.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0905    1.5456    2.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000    4.4453    0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5211    4.9488   -1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309102214372D          

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  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
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  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
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 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
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 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
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 42 44  1  0  0  0  0
 44 45  1  6  0  0  0
 44 46  1  0  0  0  0
 37 46  1  0  0  0  0
 46 47  1  1  0  0  0
 34 48  1  0  0  0  0
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 48 50  1  0  0  0  0
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 32 52  1  0  0  0  0
 52 53  1  1  0  0  0
 30 54  1  0  0  0  0
 54 55  2  0  0  0  0
 24 55  1  0  0  0  0
 27 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)CCCCCC\C=C/C\C=C/CCCCC(O)=NCCC1=CNC2=CC=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C40H62N2O13/c1-25(44)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-32(45)41-20-19-26-22-42-29-18-17-27(21-28(26)29)53-40-38(51)36(49)34(47)31(55-40)24-52-39-37(50)35(48)33(46)30(23-43)54-39/h2-3,6,8,17-18,21-22,25,30-31,33-40,42-44,46-51H,4-5,7,9-16,19-20,23-24H2,1H3,(H,41,45)/b3-2-,8-6-/t25-,30-,31-,33-,34-,35+,36+,37-,38-,39-,40-/m1/s1

> <INCHI_KEY>
ZWPVRCFACRKFAE-UHNNSHPUSA-N

> <FORMULA>
C40H62N2O13

> <MOLECULAR_WEIGHT>
778.937

> <EXACT_MASS>
778.425190064

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
117

> <JCHEM_AVERAGE_POLARIZABILITY>
85.77908917586373

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6Z,9Z,17R)-17-hydroxy-N-[2-(5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid

> <JCHEM_LOGP>
2.9629693709999994

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.906212270796194

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.403128138571265

> <JCHEM_PKA_STRONGEST_BASIC>
4.359945452469056

> <JCHEM_POLAR_SURFACE_AREA>
247.13999999999996

> <JCHEM_REFRACTIVITY>
204.49860000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6Z,9Z,17R)-17-hydroxy-N-[2-(5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      16.271 -11.140   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.605 -10.370   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      17.605  -8.830   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      18.939 -11.140   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.272 -10.370   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.606 -11.140   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.940 -10.370   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.273 -11.140   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.607 -10.370   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.941 -11.140   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.941 -12.680   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.607 -13.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.273 -12.680   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.940 -13.450   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.940 -14.990   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.273 -15.760   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.607 -14.990   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.941 -15.760   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.274 -14.990   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      28.274 -13.450   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      29.608 -15.760   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      30.942 -14.990   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.275 -15.760   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.609 -14.990   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.770 -13.458   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      35.276 -13.138   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      36.046 -14.472   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      37.553 -14.792   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      38.029 -16.257   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      36.998 -17.401   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      37.474 -18.866   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      36.444 -20.010   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      36.920 -21.475   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      35.889 -22.619   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      36.365 -24.084   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      37.871 -24.404   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      38.347 -25.869   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      39.854 -26.189   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      40.329 -27.653   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      41.836 -27.974   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      42.312 -29.438   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      39.299 -28.798   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      39.775 -30.263   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      37.793 -28.478   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      36.762 -29.622   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      37.317 -27.013   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      35.810 -26.693   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      34.383 -22.299   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      33.352 -23.443   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      33.907 -20.834   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      32.401 -20.514   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      34.937 -19.690   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      34.461 -18.225   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      35.492 -17.081   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      35.016 -15.616   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   55                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   55                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   54                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   52                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   48                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   46                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   39   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   37   47                                                  
CONECT   47   46                                                            
CONECT   48   34   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   32   53                                                  
CONECT   53   52                                                            
CONECT   54   30   55                                                       
CONECT   55   54   24   27                                                  
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

View in JSmol

Synonyms

Value	Source
(6Z,9Z,17R)-17-Hydroxy-N-[2-(5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H-indol-3-yl)ethyl]octadeca-6,9-dienimidate	Generator

Chemical Formula

C₄₀H₆₂N₂O₁₃

Average Mass

778.9370 Da

Monoisotopic Mass

778.42519 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H](O)CCCCCC\C=C/C\C=C/CCCCC(O)=NCCC1=CNC2=CC=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C12

InChI Identifier

InChI=1S/C40H62N2O13/c1-25(44)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-32(45)41-20-19-26-22-42-29-18-17-27(21-28(26)29)53-40-38(51)36(49)34(47)31(55-40)24-52-39-37(50)35(48)33(46)30(23-43)54-39/h2-3,6,8,17-18,21-22,25,30-31,33-40,42-44,46-51H,4-5,7,9-16,19-20,23-24H2,1H3,(H,41,45)/b3-2-,8-6-/t25-,30-,31-,33-,34-,35+,36+,37-,38-,39-,40-/m1/s1

InChI Key

ZWPVRCFACRKFAE-UHNNSHPUSA-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
Withania somnifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
O-glycosyl compound
Disaccharide
3-alkylindole
Indole or derivatives
Indole
Oxane
Benzenoid
Substituted pyrrole
N-acyl-amine
Fatty acyl
Fatty amide
Heteroaromatic compound
Pyrrole
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Organic nitrogen compound
Carbonyl group
Primary alcohol
Organopnictogen compound
Organonitrogen 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	2.96	ChemAxon
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	4.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	247.14 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	204.5 m³·mol⁻¹	ChemAxon
Polarizability	85.78 Å³	ChemAxon
Number of Rings	4	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

9666025

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11491218

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid (NP0300294)

MOL for NP0300294 ((6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid)

3D MOL for NP0300294 ((6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid)

3D SDF for NP0300294 ((6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid)

3D-SDF for NP0300294 ((6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid)

PDB for NP0300294 ((6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid)

3D PDB for NP0300294 ((6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid)

SMILES for NP0300294 ((6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid)

INCHI for NP0300294 ((6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid)

Structure for NP0300294 ((6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid)

3D Structure for NP0300294 ((6z,9z,17r)-17-hydroxy-n-[2-(5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)ethyl]octadeca-6,9-dienimidic acid)