NP-MRD: Showing NP-Card for 5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one (NP0301482)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 14:28:25 UTC

Updated at

2022-09-10 14:28:25 UTC

NP-MRD ID

NP0301482

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

Description

Genistein 7-o-rutinoside belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Thus, genistein 7-O-rutinoside is considered to be a flavonoid. 5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one was first documented in 2022 (PMID: 35288618). Based on a literature review very few articles have been published on Genistein 7-o-rutinoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102216282D          

 41 45  0  0  1  0            999 V2000
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    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
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    1.4289    0.0000    0.0000 C   0  0  0  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
    2.1434   -0.4125    0.0000 C   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 O   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
    4.2868   -0.0000    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
    5.0013    1.2375    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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    0.7145   -2.8875    0.0000 C   0  0  2  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
    0.7145   -3.7125    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 18 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 11 29  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  6  0  0  0
  4 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END

     RDKit          3D

 71 75  0  0  0  0  0  0  0  0999 V2000
   -6.5027   -2.0431    2.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2648   -1.3892    0.9290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4408   -0.8935   -0.0528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7512    0.2436    0.3563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7539    0.5521   -0.5571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5022    0.5382    0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757    0.8842   -1.0051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2415    0.8759   -0.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    1.1120   -1.2848 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7440    0.0768   -1.2689 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0561    0.1645   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6715    1.2952   -0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0003    1.3138   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228    2.4554    0.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7226    0.1461   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0647    0.0920    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6275    1.1477    0.6014 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7874   -1.0749    0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875   -1.1246    0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6986   -2.1364    1.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0484   -2.1574    1.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9179   -1.1807    1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2595   -1.2395    1.5738 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4046   -0.1656    0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0708   -0.1435    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -2.1967   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -2.1495   -0.6544 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1402   -1.0260   -0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -1.0034   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6247    1.3646   -2.7032 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0129    2.6956   -2.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6211    0.3844   -3.2163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0767   -0.6109   -4.0144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4691   -0.1949   -2.0959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7540   -0.4860   -2.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7938    1.3630    0.4493 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1232    2.5304    0.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7023    0.9922    1.6015 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0327    1.1780    2.8053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2614   -0.3981    1.4557 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.4279   -0.4240    0.6851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5287   -2.3956    1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3847   -1.3616    2.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0760   -2.9319    2.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8628   -2.2201    0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2895    0.0661    1.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2993   -0.4786    0.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4054    1.2798    0.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6929    1.8393   -1.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2862    2.0448   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1548    2.2359   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1888    3.3502    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0196   -2.9213    1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4412   -2.9580    2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9221   -0.5513    1.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0742    0.6179    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6343    0.6510   -0.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6116   -3.1519   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618   -1.9216   -1.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3041    1.2516   -3.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2130    3.2934   -2.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3381    0.9551   -3.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8490   -1.1027   -4.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9441   -1.0958   -1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8403   -1.4663   -2.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3462    1.3800   -0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0949    3.1598   -0.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5518    1.7027    1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2204    2.0789    3.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5596   -0.7410    2.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2980    0.0237   -0.1855 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
  9 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  4 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 40  2  1  0
 34  7  1  0
 29 11  1  0
 25 19  1  0
 28 15  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  6
  4 46  1  1
  6 47  1  0
  6 48  1  0
  7 49  1  6
  9 50  1  1
 12 51  1  0
 14 52  1  0
 26 58  1  0
 29 59  1  0
 20 53  1  0
 21 54  1  0
 23 55  1  0
 24 56  1  0
 25 57  1  0
 30 60  1  6
 31 61  1  0
 32 62  1  6
 33 63  1  0
 34 64  1  1
 35 65  1  0
 36 66  1  6
 37 67  1  0
 38 68  1  1
 39 69  1  0
 40 70  1  1
 41 71  1  0
M  END


  Mrv1652309102216282D          

 41 45  0  0  1  0            999 V2000
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    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
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    1.4289    0.0000    0.0000 C   0  0  0  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
    2.1434   -0.4125    0.0000 C   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 O   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
    4.2868   -0.0000    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
    5.0013    1.2375    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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    0.7145   -2.8875    0.0000 C   0  0  2  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
    0.7145   -3.7125    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 18 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 11 29  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  6  0  0  0
  4 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0301482

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C(=COC4=C3)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O14/c1-10-19(30)22(33)24(35)26(39-10)38-9-17-21(32)23(34)25(36)27(41-17)40-13-6-15(29)18-16(7-13)37-8-14(20(18)31)11-2-4-12(28)5-3-11/h2-8,10,17,19,21-30,32-36H,9H2,1H3/t10-,17+,19-,21+,22+,23-,24+,25+,26+,27+/m0/s1

> <INCHI_KEY>
XIQCIPHUIZGDLB-SEPMLUPWSA-N

> <FORMULA>
C27H30O14

> <MOLECULAR_WEIGHT>
578.523

> <EXACT_MASS>
578.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
56.17699773123998

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <JCHEM_LOGP>
0.08487861733333353

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.972782620341015

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.272991240968967

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121823516836606

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
134.69690000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   36                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   28                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19                                                       
CONECT   26   18   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   15   29                                                  
CONECT   29   28   11                                                       
CONECT   30    9   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    7   35                                                  
CONECT   35   34                                                            
CONECT   36    4   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38    2   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₁₄

Average Mass

578.5230 Da

Monoisotopic Mass

578.16356 Da

IUPAC Name

5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C(=COC4=C3)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H30O14/c1-10-19(30)22(33)24(35)26(39-10)38-9-17-21(32)23(34)25(36)27(41-17)40-13-6-15(29)18-16(7-13)37-8-14(20(18)31)11-2-4-12(28)5-3-11/h2-8,10,17,19,21-30,32-36H,9H2,1H3/t10-,17+,19-,21+,22+,23-,24+,25+,26+,27+/m0/s1

InChI Key

XIQCIPHUIZGDLB-SEPMLUPWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid O-glycosides

Direct Parent

Isoflavonoid O-glycosides

Alternative Parents

Substituents

Isoflavonoid o-glycoside
Isoflavonoid-7-o-glycoside
Hydroxyisoflavonoid
Isoflavone
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Oxane
Pyran
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	0.085	ChemAxon
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.7 m³·mol⁻¹	ChemAxon
Polarizability	56.18 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

31121353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76315025

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sun J, Li M, Lin T, Wang D, Chen J, Zhang Y, Mu Q, Su H, Wu N, Liu A, Yu Y, Liu Y, Wang S, Yu X, Guo J, Yu W: Cell cycle arrest is an important mechanism of action of compound Kushen injection in the prevention of colorectal cancer. Sci Rep. 2022 Mar 14;12(1):4384. doi: 10.1038/s41598-022-08336-4. [PubMed:35288618 ]
LOTUS database [Link]

Showing NP-Card for 5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one (NP0301482)

MOL for NP0301482 (5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0301482 (5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0301482 (5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0301482 (5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0301482 (5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0301482 (5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0301482 (5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0301482 (5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0301482 (5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0301482 (5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)