NP-MRD: Showing NP-Card for Frachinoside (NP0063108)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 07:35:38 UTC

Updated at

2022-04-28 07:35:38 UTC

NP-MRD ID

NP0063108

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Frachinoside

Description

Methyl (2R,3R,4S)-3-ethenyl-4-(2-oxo-2-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-hydroxy-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methoxy}ethyl)-2-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Frachinoside is found in Fraxinus chinensis . Based on a literature review very few articles have been published on methyl (2R,3R,4S)-3-ethenyl-4-(2-oxo-2-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-hydroxy-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methoxy}ethyl)-2-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209352D          

 51 55  0  0  1  0            999 V2000
   -4.2868    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5737    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5737    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1447    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 11  1  1  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
 13 22  1  6  0  0  0
  2 23  1  1  0  0  0
 23 24  2  0  0  0  0
  1 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 34 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 40 47  1  0  0  0  0
 38 48  1  0  0  0  0
 33 49  1  1  0  0  0
 32 50  1  6  0  0  0
 31 51  1  1  0  0  0
M  END

     RDKit          3D

 89 93  0  0  0  0  0  0  0  0999 V2000
   -2.3482    0.0584    2.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1228   -0.1373    0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9946    0.3069   -0.3794 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3865    1.3203   -1.2936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1593    2.0163   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0219    1.1967   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4571    0.3573   -1.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901    1.2716    0.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806    0.5447    1.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9334    0.8085    0.4647 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9806    0.0673    0.9609 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2336    0.4296    0.4418 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9478   -0.6505   -0.0085 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1715   -1.1837    0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5406   -2.3684   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7544   -2.9630   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0841   -4.0637   -0.8844 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2441   -4.5938   -0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5549   -5.6541   -1.2860 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1981   -4.0996    0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8901   -2.9471    0.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6533   -2.3771    0.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3345   -1.2287    1.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0864   -0.6438    1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8300    0.5206    1.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0236    1.3530   -0.7804 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2886    1.5970   -1.3328 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3433    2.6365   -0.3944 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8318    3.2168   -1.5559 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2086    2.2967    0.5402 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5503    2.6417    1.8245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3020    2.4808   -1.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408    3.2566   -2.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7673    4.2479   -3.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0450    2.9064   -3.7039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7101    3.5703   -4.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2623    2.8170   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4393    2.0324    0.3348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3874    0.6251    0.0236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9173   -0.1213    1.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0357   -0.8697    0.6838 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1005   -0.2848    1.3120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2028   -0.9774    1.6043 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.3530   -0.4016    0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5143   -1.0949    1.0460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2217   -2.4444    1.4157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6387   -2.8705    0.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8575   -2.9784    1.7746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6504   -2.7442    3.1321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7930   -2.2957    0.9502 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7029   -3.0365   -0.2464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6702   -0.2936    2.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2187    0.5912    2.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2273   -0.7097    0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0697   -0.6626   -1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1304    0.8996   -2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8345    2.7144   -1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575    2.6524    0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018    0.8975    2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4795   -0.5522    1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6691    0.5368   -0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7820    0.9854    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8014   -2.7861   -1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1582   -4.5876    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6273   -2.5431    1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0343   -0.7574    2.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4665    0.9404    2.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4478    0.7603   -1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8380    2.1518   -0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0478    3.3265    0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458    3.5922   -1.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2902    2.8063    0.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7116    2.7928    2.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    2.9128   -5.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2445    4.5311   -5.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210    3.7176   -5.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690    3.6960   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0369    0.3855   -0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1895   -0.6924   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5386   -0.7539    2.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4087    0.6774    1.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0314   -0.5218   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1881   -0.8599    0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9375   -2.8955    2.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5970   -3.1267    0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8594   -4.0790    1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4298   -2.3109    3.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8257   -2.4824    1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2088   -2.4996   -0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
 36 35  1  0
 35 33  1  0
 33 34  2  0
 33 32  1  0
 32 37  2  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 43 46  1  0
 46 47  1  0
 46 48  1  0
 48 49  1  0
 48 50  1  0
 50 51  1  0
 39  3  1  0
  3  2  1  0
  2  1  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 24  2  0
 24 25  1  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  2  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 12 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  4 32  1  0
 30 10  1  0
 50 41  1  0
 15 14  1  0
 16 22  1  0
 36 74  1  0
 36 75  1  0
 36 76  1  0
 37 77  1  0
 39 78  1  6
 41 79  1  6
 43 80  1  1
 44 81  1  0
 44 82  1  0
 45 83  1  0
 46 84  1  1
 47 85  1  0
 48 86  1  1
 49 87  1  0
 50 88  1  1
 51 89  1  0
  3 55  1  6
  2 54  1  0
  1 52  1  0
  1 53  1  0
  4 56  1  6
  5 57  1  0
  5 58  1  0
  9 59  1  0
  9 60  1  0
 10 61  1  6
 12 62  1  1
 25 67  1  0
 23 66  1  0
 21 65  1  0
 20 64  1  0
 15 63  1  0
 26 68  1  6
 27 69  1  0
 28 70  1  1
 29 71  1  0
 30 72  1  6
 31 73  1  0
M  END


  Mrv1652304282209352D          

 51 55  0  0  1  0            999 V2000
   -4.2868    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5737    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5737    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1447    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 11  1  1  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
 13 22  1  6  0  0  0
  2 23  1  1  0  0  0
 23 24  2  0  0  0  0
  1 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 34 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 40 47  1  0  0  0  0
 38 48  1  0  0  0  0
 33 49  1  1  0  0  0
 32 50  1  6  0  0  0
 31 51  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0063108

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@H](O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CC(=O)OC[C@@H]1O[C@@H](OC2=C(O)C=C3C=CC(=O)OC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C32H38O19/c1-3-13-14(15(29(43)44-2)10-46-30(13)51-32-28(42)25(39)23(37)19(9-33)49-32)7-22(36)45-11-20-24(38)26(40)27(41)31(50-20)48-18-8-17-12(6-16(18)34)4-5-21(35)47-17/h3-6,8,10,13-14,19-20,23-28,30-34,37-42H,1,7,9,11H2,2H3/t13-,14+,19+,20+,23-,24-,25+,26+,27-,28-,30-,31-,32+/m1/s1

> <INCHI_KEY>
YNOUJPHGTJKBFJ-LHEHEVGASA-N

> <FORMULA>
C32H38O19

> <MOLECULAR_WEIGHT>
726.637

> <EXACT_MASS>
726.200729004

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
67.78521223892243

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R,3R,4S)-3-ethenyl-4-(2-oxo-2-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-hydroxy-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methoxy}ethyl)-2-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <ALOGPS_LOGP>
-0.42

> <JCHEM_LOGP>
-1.9587029439999997

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.905203276348518

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.687767625718616

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615592584

> <JCHEM_POLAR_SURFACE_AREA>
286.89

> <JCHEM_REFRACTIVITY>
163.60860000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4S,5R,6R)-5-ethenyl-4-(2-oxo-2-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-hydroxy-2-oxochromen-7-yl)oxy]oxan-2-yl]methoxy}ethyl)-6-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -10.669  10.780   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.335  10.780   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -6.668  13.090   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -12.003   8.470   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -13.337   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -14.670   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -16.004   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -16.004  10.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -14.670  11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -13.337  10.780   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -14.670  13.090   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -16.004  13.860   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -17.338  11.550   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0     -17.338   8.470   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0     -14.670   6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -8.002   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -5.335   6.160   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    6   25                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15                                                            
CONECT   21   14                                                            
CONECT   22   13                                                            
CONECT   23    2   24                                                       
CONECT   24   23                                                            
CONECT   25    1   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   51                                                  
CONECT   32   31   33   50                                                  
CONECT   33   32   34   49                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   30                                                       
CONECT   36   34   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39   48                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   47                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41   37                                                       
CONECT   43   41   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   40                                                       
CONECT   48   38                                                            
CONECT   49   33                                                            
CONECT   50   32                                                            
CONECT   51   31                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2R,3R,4S)-3-ethenyl-4-(2-oxo-2-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-hydroxy-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methoxy}ethyl)-2-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₃₂H₃₈O₁₉

Average Mass

726.6370 Da

Monoisotopic Mass

726.20073 Da

IUPAC Name

methyl (2R,3R,4S)-3-ethenyl-4-(2-oxo-2-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-hydroxy-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methoxy}ethyl)-2-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (4S,5R,6R)-5-ethenyl-4-(2-oxo-2-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-hydroxy-2-oxochromen-7-yl)oxy]oxan-2-yl]methoxy}ethyl)-6-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@H](O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CC(=O)OC[C@@H]1O[C@@H](OC2=C(O)C=C3C=CC(=O)OC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C32H38O19/c1-3-13-14(15(29(43)44-2)10-46-30(13)51-32-28(42)25(39)23(37)19(9-33)49-32)7-22(36)45-11-20-24(38)26(40)27(41)31(50-20)48-18-8-17-12(6-16(18)34)4-5-21(35)47-17/h3-6,8,10,13-14,19-20,23-28,30-34,37-42H,1,7,9,11H2,2H3/t13-,14+,19+,20+,23-,24-,25+,26+,27-,28-,30-,31-,32+/m1/s1

InChI Key

YNOUJPHGTJKBFJ-LHEHEVGASA-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
Fraxinus chinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin o-glycoside
Coumarin-7-o-glycoside
Saccharolipid
Terpene glycoside
Terpene lactone
Phenolic glycoside
Hydroxycoumarin
O-glycosyl compound
Secoiridoid-skeleton
Glycosyl compound
1-benzopyran
Monoterpenoid
Bicyclic monoterpenoid
Benzopyran
Aromatic monoterpenoid
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
Pyranone
Benzenoid
Pyran
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	-0.42	ALOGPS
logP	-2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.69	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	286.89 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	163.61 m³·mol⁻¹	ChemAxon
Polarizability	67.79 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163056133

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Frachinoside (NP0063108)

MOL for NP0063108 (Frachinoside)

3D MOL for NP0063108 (Frachinoside)

3D SDF for NP0063108 (Frachinoside)

3D-SDF for NP0063108 (Frachinoside)

PDB for NP0063108 (Frachinoside)

3D PDB for NP0063108 (Frachinoside)

SMILES for NP0063108 (Frachinoside)

INCHI for NP0063108 (Frachinoside)

Structure for NP0063108 (Frachinoside)

3D Structure for NP0063108 (Frachinoside)