NP-MRD: Showing NP-Card for Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside) (NP0052592)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 23:34:50 UTC

Updated at

2022-04-27 23:34:50 UTC

NP-MRD ID

NP0052592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside)

Description

[(2S,3R,4S,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid belongs to the class of organic compounds known as flavonoid-8-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C8-position. Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside) is found in Althaea officinalis . Based on a literature review very few articles have been published on [(2S,3R,4S,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201342D          

 37 40  0  0  1  0            999 V2000
   -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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  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
   -1.4289    2.4750    0.0000 C   0  0  2  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
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   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
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    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
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    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
    2.1434   -0.4125    0.0000 C   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   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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
    3.5724    1.2375    0.0000 C   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
    4.2868   -0.0000    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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   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    0.0000    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
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
  9 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 36  1  0  0  0  0
  1 37  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    7.0096    2.9172    0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7208    2.6431    1.1519 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855    1.6626    0.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6220    1.4918    1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7583    0.5296    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1171   -0.3141   -0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1503   -1.3189   -0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4149   -2.2125   -1.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229   -3.1700   -2.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8477   -3.9503   -3.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2893   -3.2004   -1.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6692   -4.1128   -2.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5091   -5.0466   -3.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953   -4.0535   -1.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103   -3.1394   -0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3406   -3.1277    0.2585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1624   -2.2237    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3637   -1.2903    1.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8924   -0.0385    0.7149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8988    0.9261    0.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089    2.2126    0.6972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2896    2.9420   -0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1898    2.2726   -1.3637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546    2.3679    0.0579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6345    2.1379   -1.3161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7223    1.5477    0.7529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5358    2.3080    1.5713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588    0.4007    1.5304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0290   -0.5357    1.7592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4009   -0.7409    3.3679 S   0  0  2  0  0  6  0  0  0  0  0  0
   -3.9110   -2.0785    3.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9070   -0.6889    3.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323    0.4544    4.3302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0566   -2.2793   -0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9536   -1.4030   -0.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3706   -0.1541   -0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2454    0.8266   -0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9850    3.7298   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6488    3.2350    1.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5081    2.0291    0.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3233    2.1515    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706    0.3968    1.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3987   -2.1767   -2.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2464   -5.2243   -3.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6377   -4.7757   -1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0674   -3.7704    0.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1771    0.0470   -0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3847    2.6947    1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6981    2.8188    0.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5029    4.0123   -0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166    1.3049   -1.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569    3.4402    0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4963    1.7202   -1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3440    1.0651   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4334    2.4240    1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759    0.8739    2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2403    1.3211    4.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825   -0.7962   -1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2238    0.9170   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 36  1  0
 36 37  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 30 29  1  6
 30 33  1  0
 30 31  2  0
 30 32  2  0
 17 34  2  0
 34 35  1  0
 37  3  1  0
 35  7  1  0
 34 11  1  0
 28 19  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  0
 36 58  1  0
 37 59  1  0
  8 43  1  0
 13 44  1  0
 14 45  1  0
 16 46  1  0
 19 47  1  6
 21 48  1  1
 22 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  6
 25 53  1  0
 26 54  1  6
 27 55  1  0
 28 56  1  1
 33 57  1  0
M  END


  Mrv1652304282201342D          

 37 40  0  0  1  0            999 V2000
   -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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  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
   -1.4289    2.4750    0.0000 C   0  0  2  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
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   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
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    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
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    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
    2.1434   -0.4125    0.0000 C   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   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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
    3.5724    1.2375    0.0000 C   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
    4.2868   -0.0000    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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   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    0.0000    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
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
  9 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 36  1  0  0  0  0
  1 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C(O[C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]3OS(O)(=O)=O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O14S/c1-32-10-4-2-9(3-5-10)14-7-12(25)16-11(24)6-13(26)19(20(16)33-14)35-22-21(36-37(29,30)31)18(28)17(27)15(8-23)34-22/h2-7,15,17-18,21-24,26-28H,8H2,1H3,(H,29,30,31)/t15-,17+,18-,21+,22-/m0/s1

> <INCHI_KEY>
ICXGFKZMXFCHLZ-MFOVYWPASA-N

> <FORMULA>
C22H22O14S

> <MOLECULAR_WEIGHT>
542.46

> <EXACT_MASS>
542.073026562

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
49.584451697728454

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,3R,4S,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.28

> <JCHEM_LOGP>
-1.715266037412221

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.963438343628177

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.321500747694137

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810940272950566

> <JCHEM_POLAR_SURFACE_AREA>
218.73999999999995

> <JCHEM_REFRACTIVITY>
121.51329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3R,4S,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

> <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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   19  S   UNK     0       0.000   6.160   0.000  0.00  0.00           S+0
HETATM   20  O   UNK     0      -1.540   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.540   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   37                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    9   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23    5   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25    4   27                                                  
CONECT   27   26                                                            
CONECT   28   24   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   31   35                                                       
CONECT   35   34                                                            
CONECT   36    3                                                            
CONECT   37    1                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
[(2S,3R,4S,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonate	Generator
[(2S,3R,4S,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxidanesulphonate	Generator
[(2S,3R,4S,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxidanesulphonic acid	Generator

Chemical Formula

C₂₂H₂₂O₁₄S

Average Mass

542.4600 Da

Monoisotopic Mass

542.07303 Da

IUPAC Name

[(2S,3R,4S,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

Traditional Name

[(2S,3R,4S,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C(O[C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]3OS(O)(=O)=O)=C2O1

InChI Identifier

InChI=1S/C22H22O14S/c1-32-10-4-2-9(3-5-10)14-7-12(25)16-11(24)6-13(26)19(20(16)33-14)35-22-21(36-37(29,30)31)18(28)17(27)15(8-23)34-22/h2-7,15,17-18,21-24,26-28H,8H2,1H3,(H,29,30,31)/t15-,17+,18-,21+,22-/m0/s1

InChI Key

ICXGFKZMXFCHLZ-MFOVYWPASA-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
Althaea officinalis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-8-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-8-O-glycosides

Alternative Parents

Substituents

Flavonoid-8-o-glycoside
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Organic sulfuric acid or derivatives
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	0.28	ALOGPS
logP	-1.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	218.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.51 m³·mol⁻¹	ChemAxon
Polarizability	49.58 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

163056015

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside) (NP0052592)

MOL for NP0052592 (Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside))

3D MOL for NP0052592 (Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside))

3D SDF for NP0052592 (Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside))

3D-SDF for NP0052592 (Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside))

PDB for NP0052592 (Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside))

3D PDB for NP0052592 (Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside))

SMILES for NP0052592 (Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside))

INCHI for NP0052592 (Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside))

Structure for NP0052592 (Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside))

3D Structure for NP0052592 (Isoscutellarein 4'-methyl ether 8-(2''-sulfatoglucoside))