NP-MRD: Showing NP-Card for 2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one (NP0052817)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 23:44:19 UTC

Updated at

2022-04-27 23:44:19 UTC

NP-MRD ID

NP0052817

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one

Description

[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2R)-2-methylbutanoate belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. 2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one is found in Arnica chamissonis. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2R)-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201442D          

 40 43  0  0  1  0            999 V2000
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    0.8250    0.0000 O   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
   -1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   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
    2.1434   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  3 20  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 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
 28 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  1  1  0  0  0
 27 38  1  1  0  0  0
 26 39  1  6  0  0  0
 25 40  1  1  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
   -7.7475    3.5572   -1.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2261    2.6007   -0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0837    1.7685   -1.0628 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9067    2.5850   -1.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7420    0.6972   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3962    0.6228    0.9619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7425   -0.2319   -0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4616   -1.2297    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3313   -2.1372    0.1770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1922   -1.4273   -0.0198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1087   -1.8751    0.7528 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0137   -1.0987    0.5271 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910   -1.2591    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0999   -0.1213    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4358   -0.2042   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1050    0.9329   -0.4889 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3753    0.9297   -0.7869 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0978    2.2091   -0.9899 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4258    2.2884   -1.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0863    3.4776   -1.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3983    4.6624   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0713    5.8479   -1.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0427    4.6250   -1.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3575    5.8298   -0.9131 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4182    3.4089   -0.8627 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0085   -0.2800   -0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601   -1.4989   -0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9483   -2.5822   -0.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0150   -1.4506   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2762   -2.6001   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -3.8272   -0.2953 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -2.4610    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356   -3.6532    0.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3239   -4.2467    1.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5886   -1.8084    2.2148 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5109   -2.0130    3.0719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570   -2.9401    2.4222 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4825   -2.5642    3.4132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713   -3.2635    1.1651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6758   -4.3870    0.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9668    3.8988   -2.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5568    3.0668   -2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1674    4.4366   -1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0602    1.9333   -0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9587    3.1776    0.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4657    1.2479   -1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0254    1.9461   -1.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1344    3.0089   -2.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6880    3.4283   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3776   -1.8911    0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3137   -0.8859    1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6972   -2.6202   -0.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9082   -2.9357    0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6210    0.8322    0.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9990    1.3860   -1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1514    3.4695   -1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0486    5.8523   -1.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732    6.6832   -1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3688    3.4158   -0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0668   -0.3392   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286   -4.2782   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3438   -4.6117    1.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791   -5.0680    1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6988   -3.5219    2.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0462   -0.8048    2.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7252   -2.6608    3.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9552   -3.8141    2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7620   -3.3796    3.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3300   -3.5165    1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7941   -4.3382   -0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 32  2  0
 32 33  1  0
 33 34  1  0
 32 30  1  0
 30 31  1  0
 30 29  2  0
 29 27  1  0
 27 28  2  0
 27 26  1  0
 26 17  2  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 11 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39  9  1  0
 14 13  1  0
 25 18  1  0
 15 29  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  2 44  1  0
  2 45  1  0
  3 46  1  6
  4 47  1  0
  4 48  1  0
  4 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  6
 11 53  1  6
 34 62  1  0
 34 63  1  0
 34 64  1  0
 31 61  1  0
 26 60  1  0
 14 54  1  0
 19 55  1  0
 20 56  1  0
 22 57  1  0
 24 58  1  0
 25 59  1  0
 35 65  1  1
 36 66  1  0
 37 67  1  1
 38 68  1  0
 39 69  1  1
 40 70  1  0
M  END


  Mrv1652304282201442D          

 40 43  0  0  1  0            999 V2000
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    0.8250    0.0000 O   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
   -1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   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
    2.1434   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  3 20  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 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
 28 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  1  1  0  0  0
 27 38  1  1  0  0  0
 26 39  1  6  0  0  0
 25 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0052817

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O13/c1-4-11(2)26(35)37-10-19-21(31)23(33)24(34)27(40-19)39-18-9-17-20(22(32)25(18)36-3)15(30)8-16(38-17)12-5-6-13(28)14(29)7-12/h5-9,11,19,21,23-24,27-29,31-34H,4,10H2,1-3H3/t11-,19-,21-,23+,24-,27-/m1/s1

> <INCHI_KEY>
SLCJQMHYGNUWLY-YOGRAHPASA-N

> <FORMULA>
C27H30O13

> <MOLECULAR_WEIGHT>
562.524

> <EXACT_MASS>
562.168641026

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.80958793540475

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2R)-2-methylbutanoate

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.106600653666666

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.765534174286087

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.826728255262602

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491030247556058

> <JCHEM_POLAR_SURFACE_AREA>
201.67

> <JCHEM_REFRACTIVITY>
136.45630000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2R)-2-methylbutanoate

> <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      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.003   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.336   0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -10.669   3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0     -13.337   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334  -8.470   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.000 -10.780   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -5.335 -10.780   0.000  0.00  0.00           O+0
CONECT    1    2    6   23                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16                                                            
CONECT   19   15                                                            
CONECT   20    3                                                            
CONECT   21    2   22                                                       
CONECT   22   21                                                            
CONECT   23    1   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   40                                                  
CONECT   26   25   27   39                                                  
CONECT   27   26   28   38                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34                                                            
CONECT   38   27                                                            
CONECT   39   26                                                            
CONECT   40   25                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2R)-2-methylbutanoic acid	Generator

Chemical Formula

C₂₇H₃₀O₁₃

Average Mass

562.5240 Da

Monoisotopic Mass

562.16864 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2R)-2-methylbutanoate

Traditional Name

[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2R)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H30O13/c1-4-11(2)26(35)37-10-19-21(31)23(33)24(34)27(40-19)39-18-9-17-20(22(32)25(18)36-3)15(30)8-16(38-17)12-5-6-13(28)14(29)7-12/h5-9,11,19,21,23-24,27-29,31-34H,4,10H2,1-3H3/t11-,19-,21-,23+,24-,27-/m1/s1

InChI Key

SLCJQMHYGNUWLY-YOGRAHPASA-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
Arnica chamissonis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Saccharolipid
6-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Catechol
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.26	ALOGPS
logP	2.11	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.46 m³·mol⁻¹	ChemAxon
Polarizability	55.81 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

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

163105978

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one (NP0052817)

MOL for NP0052817 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one)

3D MOL for NP0052817 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one)

3D SDF for NP0052817 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one)

3D-SDF for NP0052817 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one)

PDB for NP0052817 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one)

3D PDB for NP0052817 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one)

SMILES for NP0052817 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one)

INCHI for NP0052817 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one)

Structure for NP0052817 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one)

3D Structure for NP0052817 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[[6-O-(2-methyl-1-oxobutyl)-beta-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one)