NP-MRD: Showing NP-Card for 2,3-Dihydro-5'-hydroxyrobustaflavone (NP0054324)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 00:43:01 UTC

Updated at

2022-04-28 00:43:01 UTC

NP-MRD ID

NP0054324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-Dihydro-5'-hydroxyrobustaflavone

Description

6-{5-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-2,3-dihydroxyphenyl}-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. 2,3-Dihydro-5'-hydroxyrobustaflavone is found in Plagiomnium cuspidatum and Plagiomnium undulatum. Based on a literature review very few articles have been published on 6-{5-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-2,3-dihydroxyphenyl}-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202432D          

 41 46  0  0  1  0            999 V2000
   -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 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
   -2.8579   -2.4750    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   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   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
   -5.0013   -0.4125    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   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
   -5.7158    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
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 O   0  0  0  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
   -0.7145   -2.8875    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
    0.0000   -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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.0000   -2.4750    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
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 10 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
  9 17  1  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
  4 20  1  0  0  0  0
  3 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 22 27  2  0  0  0  0
 27 28  1  0  0  0  0
 25 29  1  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
 24 32  1  0  0  0  0
 32 33  2  0  0  0  0
 30 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 37 40  1  0  0  0  0
 23 41  1  0  0  0  0
M  END

     RDKit          3D

 61 66  0  0  0  0  0  0  0  0999 V2000
   -4.9148   -3.0296    1.1842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688   -1.8328    0.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7249   -1.0280    0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0692    0.4170    0.6034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8842    1.2317    0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    2.5256   -0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0413    3.3779   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227    4.6675   -0.9262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797    2.8469   -0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3068    3.6371   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195    1.5505    0.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8641    1.0850    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506    1.2613    1.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9222    1.8730    2.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8721    0.8204    1.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5201    0.2107    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7526   -0.1912    0.4752 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4395   -0.7835   -0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8126   -1.1697   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3683   -0.9254    1.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6572   -1.2695    1.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4678   -1.8889    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7709   -2.2367    0.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9462   -2.1468   -0.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6326   -1.7914   -1.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8357   -0.9945   -1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5095   -0.5746   -1.8493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139   -0.7472   -2.9321 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8252    0.0388   -0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281    0.4738   -0.9098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8488    0.2935   -2.0981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917    0.7597    0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0385    0.5863   -0.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2503   -0.0784   -0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4384    0.4763   -0.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5951   -0.2372   -0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7760    0.3329   -1.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5791   -1.4670    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4082   -2.0173    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3427   -3.2525    1.0941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2324   -1.3156    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261   -1.1012    1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0244   -1.4474    0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    0.8249    1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0898    2.9465   -0.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950    5.3028   -1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2768    4.5815   -1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4537    1.9859    3.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.9523    2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7229   -0.4283    1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0670   -1.0625    2.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0161   -3.1338    1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5781   -2.6348   -1.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2674   -2.0168   -2.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3682   -1.4748   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1099    0.5905   -2.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4029   -0.2505    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4209    1.4505   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8090    1.2226   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5015   -2.0236    0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1963   -3.7718    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 19 25  1  0
 25 24  2  0
 19 18  1  0
 18 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 30 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 12 11  1  0
 11 32  2  0
 32  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 41  1  0
 41 34  2  0
 34 33  1  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 39 40  1  0
 24 22  1  0
 17 18  1  0
  9 11  1  0
 33  4  1  0
 16 29  1  0
 39 41  1  0
 23 52  1  0
 21 51  1  0
 20 50  1  0
 25 54  1  0
 24 53  1  0
 26 55  1  0
 31 56  1  0
 14 48  1  0
 15 49  1  0
 32 57  1  0
  6 45  1  0
  8 46  1  0
 10 47  1  0
  4 44  1  1
  3 42  1  0
  3 43  1  0
 35 58  1  0
 37 59  1  0
 38 60  1  0
 40 61  1  0
M  END


  Mrv1652304282202432D          

 41 46  0  0  1  0            999 V2000
   -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 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
   -2.8579   -2.4750    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   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   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
   -5.0013   -0.4125    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   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
   -5.7158    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
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 O   0  0  0  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
   -0.7145   -2.8875    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
    0.0000   -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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.0000   -2.4750    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
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 10 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
  9 17  1  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
  4 20  1  0  0  0  0
  3 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 22 27  2  0  0  0  0
 27 28  1  0  0  0  0
 25 29  1  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
 24 32  1  0  0  0  0
 32 33  2  0  0  0  0
 30 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 37 40  1  0  0  0  0
 23 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C(=C(O)C=C2O1)C1=CC(=CC(O)=C1O)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H20O11/c31-14-3-1-12(2-4-14)22-10-20(36)28-25(40-22)11-18(34)26(30(28)39)16-5-13(6-21(37)29(16)38)23-9-19(35)27-17(33)7-15(32)8-24(27)41-23/h1-8,10-11,23,31-34,37-39H,9H2/t23-/m0/s1

> <INCHI_KEY>
CXUZKWBMLDRVJW-QHCPKHFHSA-N

> <FORMULA>
C30H20O11

> <MOLECULAR_WEIGHT>
556.479

> <EXACT_MASS>
556.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
55.73440113800896

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{5-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-2,3-dihydroxyphenyl}-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
4.912211408333333

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.390966262722641

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.1822594249531635

> <JCHEM_PKA_STRONGEST_BASIC>
-5.0613197440636

> <JCHEM_POLAR_SURFACE_AREA>
194.20999999999998

> <JCHEM_REFRACTIVITY>
145.26279999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{5-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-2,3-dihydroxyphenyl}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.669   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.336   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0     -12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7                                                       
CONECT   14   10   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16    9                                                       
CONECT   18   16                                                            
CONECT   19   14                                                            
CONECT   20    4                                                            
CONECT   21    3                                                            
CONECT   22    2   23   27                                                  
CONECT   23   22   24   41                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
CONECT   29   25   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   24   33                                                  
CONECT   33   32                                                            
CONECT   34   30   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
CONECT   40   37                                                            
CONECT   41   23                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₀O₁₁

Average Mass

556.4790 Da

Monoisotopic Mass

556.10056 Da

IUPAC Name

6-{5-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-2,3-dihydroxyphenyl}-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

6-{5-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-2,3-dihydroxyphenyl}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C(=C(O)C=C2O1)C1=CC(=CC(O)=C1O)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O

InChI Identifier

InChI=1S/C30H20O11/c31-14-3-1-12(2-4-14)22-10-20(36)28-25(40-22)11-18(34)26(30(28)39)16-5-13(6-21(37)29(16)38)23-9-19(35)27-17(33)7-15(32)8-24(27)41-23/h1-8,10-11,23,31-34,37-39H,9H2/t23-/m0/s1

InChI Key

CXUZKWBMLDRVJW-QHCPKHFHSA-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
Mnium cuspidatum	Plant	KNApSAcK
Plagiomnium undulatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Flavone
Hydroxyflavonoid
Flavan
Biphenol
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl ketone
Aryl alkyl ketone
Catechol
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
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	4	ALOGPS
logP	4.91	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	6.18	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	194.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	145.26 m³·mol⁻¹	ChemAxon
Polarizability	55.73 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

162907847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,3-Dihydro-5'-hydroxyrobustaflavone (NP0054324)

MOL for NP0054324 (2,3-Dihydro-5'-hydroxyrobustaflavone)

3D MOL for NP0054324 (2,3-Dihydro-5'-hydroxyrobustaflavone)

3D SDF for NP0054324 (2,3-Dihydro-5'-hydroxyrobustaflavone)

3D-SDF for NP0054324 (2,3-Dihydro-5'-hydroxyrobustaflavone)

PDB for NP0054324 (2,3-Dihydro-5'-hydroxyrobustaflavone)

3D PDB for NP0054324 (2,3-Dihydro-5'-hydroxyrobustaflavone)

SMILES for NP0054324 (2,3-Dihydro-5'-hydroxyrobustaflavone)

INCHI for NP0054324 (2,3-Dihydro-5'-hydroxyrobustaflavone)

Structure for NP0054324 (2,3-Dihydro-5'-hydroxyrobustaflavone)

3D Structure for NP0054324 (2,3-Dihydro-5'-hydroxyrobustaflavone)