NP-MRD: Showing NP-Card for (+)-Gynoside B (NP0079068)

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Record Information

Version

1.0

Created at

2022-04-29 00:08:25 UTC

Updated at

2022-04-29 00:08:25 UTC

NP-MRD ID

NP0079068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Gynoside B

Description

(2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-{[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-16-hydroxy-14-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. (+)-Gynoside B is found in Gynostemma pentaphyllum . Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-{[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-16-hydroxy-14-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202082D          

 56 62  0  0  1  0            999 V2000
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114   -1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6537   -1.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4710   -1.4224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6162   -0.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8887   -0.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0426   -2.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6143   -2.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4478   -2.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6375   -1.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932   -1.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776    1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    2.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416    0.0722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1613   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6931   -1.3344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5052   -1.1892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7855   -0.4133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2537    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5340    0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3461    1.1386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6264    1.9145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4385    2.0597    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9704    1.4290    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6901    0.6531    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8779    0.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2219    0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0340    0.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7825    1.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7188    2.8356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0946    2.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5976   -0.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0370   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4128   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6007   -2.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814    1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  6  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 13 16  1  1  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 11 20  1  1  0  0  0
  4 21  1  1  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  6  0  0  0
 33 32  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  1  0  0  0
 40 39  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 40 45  1  0  0  0  0
 44 46  1  6  0  0  0
 46 47  1  0  0  0  0
 43 48  1  6  0  0  0
 42 49  1  6  0  0  0
 41 50  1  1  0  0  0
 37 51  1  6  0  0  0
 36 52  1  6  0  0  0
 35 53  1  6  0  0  0
 53 54  1  0  0  0  0
 25 55  1  6  0  0  0
  3 56  1  6  0  0  0
M  END

     RDKit          3D

128134  0  0  0  0  0  0  0  0999 V2000
   10.9606   -0.6190   -1.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4816   -0.8910   -1.4670 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2033   -2.2142   -0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1806   -1.0857   -2.8141 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6698    0.2325   -0.8908 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0520    0.5975    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7477    1.1995    1.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7429    0.3073    0.2447 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7317   -0.9587    1.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3829    0.8991    0.2560 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4175    2.3434   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734    2.6806   -0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    1.4124   -0.3494 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8888    1.4344    1.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3356    0.3601   -0.6311 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8971   -1.0278   -0.5254 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6245   -1.8553   -1.4236 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4668   -1.3331   -0.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541   -0.1963   -0.6595 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0980   -0.4428   -0.9595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2113   -0.5861   -2.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2190   -1.7768   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990   -2.0189   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3986   -0.8914    0.5392 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7692   -1.1448    0.4860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3012   -1.4048    1.7135 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6674   -2.7965    1.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8824   -2.9856    3.1950 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9529   -4.4373    3.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9846   -5.1043    2.9149 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5856   -0.6788    1.9465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5619    0.5854    1.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5761    0.8437    0.5273 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1171    1.0920   -0.7525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1184    0.6892   -1.6376 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6509    0.9489   -3.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6228    0.5602   -3.9587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3849    1.4545   -1.3083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9684    1.9927   -2.4315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0653    2.5918   -0.3516 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1402    3.4456   -0.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5055    1.9414    0.9222 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6260    1.4725    1.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946    0.4535    0.0009 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4552    1.4638    1.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9284    0.7565   -1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0448    2.1661   -1.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2698   -0.3868   -0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4810   -1.5746   -1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3000    0.1316   -2.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3505   -2.0916    0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0345   -2.8950   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2183   -2.6145   -1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8995    1.1335   -1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8616    1.3742    0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4224   -0.2232    1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6243    1.0687    2.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7359    2.2249    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4713   -1.8646    0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9416   -0.8019    1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6669   -1.0809    1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0055    1.0068    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8761    3.0235    0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9422    2.3438   -1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    3.4754    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    3.1434   -1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    2.2472    1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8157    1.7634    1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0878    0.4953    1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7133    0.5326   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309   -1.4426    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9974   -1.2383   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1366   -2.1652   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3323   -1.7543   -1.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5607   -0.0849    0.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815   -1.1417   -2.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2734    0.3122   -3.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5434   -1.3006   -2.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -2.5689   -0.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2146   -1.8137    0.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8237   -2.9260    0.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2075   -2.2271   -1.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -0.9623    1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5632   -1.2932    2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9994   -2.5211    3.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292202082D          

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M  END
> <DATABASE_ID>
NP0079068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H]1CC[C@](C)(O1)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C42H72O14/c1-37(2)24-10-15-40(6)25(17-21(45)28-20(9-14-41(28,40)7)42(8)16-12-27(56-42)38(3,4)51)39(24,5)13-11-26(37)54-36-34(32(49)30(47)23(19-44)53-36)55-35-33(50)31(48)29(46)22(18-43)52-35/h20-36,43-51H,9-19H2,1-8H3/t20-,21+,22+,23+,24-,25+,26-,27-,28-,29-,30-,31-,32-,33+,34+,35-,36-,39-,40+,41+,42-/m0/s1

> <INCHI_KEY>
VBWLFPXNVMBQCR-BCXWYSQBSA-N

> <FORMULA>
C42H72O14

> <MOLECULAR_WEIGHT>
801.024

> <EXACT_MASS>
800.492206998

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
128

> <JCHEM_AVERAGE_POLARIZABILITY>
88.55280201978087

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-{[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-16-hydroxy-14-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
1.77

> <JCHEM_LOGP>
1.0115312753333314

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.692945883393431

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.087333394068143

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835766873476

> <JCHEM_POLAR_SURFACE_AREA>
228.21999999999997

> <JCHEM_REFRACTIVITY>
200.9

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-{[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-16-hydroxy-14-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.928  -2.940   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.554  -2.866   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.079  -2.655   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.350  -1.139   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.992  -0.413   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.146  -3.766   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.213  -4.876   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.036  -4.833   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.257  -2.698   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.574  -2.293   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.332   3.252   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.028   3.743   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.691   0.135   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.168  -1.314   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.160  -2.491   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.676  -2.220   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.200  -0.771   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.207   0.406   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.730   1.854   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -6.246   2.125   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.769   3.574   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -8.285   3.845   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -9.278   2.667   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -8.755   1.219   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -7.239   0.948   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -9.748   0.042   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0     -11.263   0.313   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0     -10.794   2.939   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -8.809   5.293   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -5.777   4.751   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -6.716  -0.500   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -5.669  -3.397   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -2.637  -3.939   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -1.121  -4.210   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       5.939   2.832   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4   22   56                                             
CONECT    4    3    5   10   21                                             
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   15   20                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   11                                                       
CONECT   16   13   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   11                                                            
CONECT   21    4                                                            
CONECT   22    3   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24    2   26   55                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   24   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   53                                                  
CONECT   36   35   37   52                                                  
CONECT   37   36   38   51                                                  
CONECT   38   37   33   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   45                                                  
CONECT   41   40   42   50                                                  
CONECT   42   41   43   49                                                  
CONECT   43   42   44   48                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44   40                                                       
CONECT   46   44   47                                                       
CONECT   47   46                                                            
CONECT   48   43                                                            
CONECT   49   42                                                            
CONECT   50   41                                                            
CONECT   51   37                                                            
CONECT   52   36                                                            
CONECT   53   35   54                                                       
CONECT   54   53                                                            
CONECT   55   25                                                            
CONECT   56    3                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₇₂O₁₄

Average Mass

801.0240 Da

Monoisotopic Mass

800.49221 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1CC[C@](C)(O1)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@@]21C

InChI Identifier

InChI=1S/C42H72O14/c1-37(2)24-10-15-40(6)25(17-21(45)28-20(9-14-41(28,40)7)42(8)16-12-27(56-42)38(3,4)51)39(24,5)13-11-26(37)54-36-34(32(49)30(47)23(19-44)53-36)55-35-33(50)31(48)29(46)22(18-43)52-35/h20-36,43-51H,9-19H2,1-8H3/t20-,21+,22+,23+,24-,25+,26-,27-,28-,29-,30-,31-,32-,33+,34+,35-,36-,39-,40+,41+,42-/m0/s1

InChI Key

VBWLFPXNVMBQCR-BCXWYSQBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Gynostemma pentaphyllum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Steroidal glycoside
14-alpha-methylsteroid
Hydroxysteroid
12-hydroxysteroid
Steroid
O-glycosyl compound
Glycosyl compound
Disaccharide
Oxane
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.77	ALOGPS
logP	1.01	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	228.22 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	200.9 m³·mol⁻¹	ChemAxon
Polarizability	88.55 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162909787

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Gynoside B (NP0079068)

MOL for NP0079068 ((+)-Gynoside B)

3D MOL for NP0079068 ((+)-Gynoside B)

3D SDF for NP0079068 ((+)-Gynoside B)

3D-SDF for NP0079068 ((+)-Gynoside B)

PDB for NP0079068 ((+)-Gynoside B)

3D PDB for NP0079068 ((+)-Gynoside B)

SMILES for NP0079068 ((+)-Gynoside B)

INCHI for NP0079068 ((+)-Gynoside B)

Structure for NP0079068 ((+)-Gynoside B)

3D Structure for NP0079068 ((+)-Gynoside B)