NP-MRD: Showing NP-Card for (6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate (NP0213424)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 12:24:35 UTC

Updated at

2022-09-05 12:24:35 UTC

NP-MRD ID

NP0213424

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

Description

Eriodictyol 7-(6-galloylglucoside) belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Eriodictyol 7-(6-galloylglucoside) is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Eriodictyol 7-(6-galloylglucoside) has been detected, but not quantified in, fruits. (6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate is found in Balanophora harlandii and Phyllanthus emblica. This could make eriodictyol 7-(6-galloylglucoside) a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061311302D          

 43 47  0  0  0  0            999 V2000
    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 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
   -3.5724   -2.8875    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
    1.4289    0.8250    0.0000 C   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
    4.2868    0.8250    0.0000 C   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
    5.0013   -0.4125    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    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
    2.1434    1.2375    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   -2.4750    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    0.0000    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
    0.0000   -2.4750    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
   -4.2868   -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  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
    1.4289   -1.6500    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  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
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   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
    0.7145   -0.4125    0.0000 O   0  0  0  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
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
 10  1  1  0  0  0  0
 10  3  2  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 13  2  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 17  4  1  0  0  0  0
 18  5  2  0  0  0  0
 19  8  1  0  0  0  0
 19 10  1  0  0  0  0
 20  7  2  0  0  0  0
 21  9  1  0  0  0  0
 22 15  2  0  0  0  0
 22 16  1  0  0  0  0
 22 20  1  0  0  0  0
 23 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24 21  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 11  1  0  0  0  0
 28 26  1  0  0  0  0
 29 13  1  0  0  0  0
 30 14  1  0  0  0  0
 31 15  1  0  0  0  0
 32 16  2  0  0  0  0
 33 17  1  0  0  0  0
 34 18  1  0  0  0  0
 35 23  1  0  0  0  0
 36 24  1  0  0  0  0
 37 25  1  0  0  0  0
 38 26  1  0  0  0  0
 39 27  2  0  0  0  0
 40  9  1  0  0  0  0
 40 27  1  0  0  0  0
 41 12  1  0  0  0  0
 41 28  1  0  0  0  0
 42 19  1  0  0  0  0
 42 20  1  0  0  0  0
 43 21  1  0  0  0  0
 43 28  1  0  0  0  0
M  END

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
   -4.5752   -3.2218   -0.1700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1344   -2.1367    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3594   -1.0497    0.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9642   -1.1836    0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3407    0.1383    0.9500 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9875   -0.0359    1.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439    1.1399    0.9501 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2894    1.3590   -0.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6249    1.4595   -0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040    1.6805   -1.9672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3267    1.7855   -2.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7220    2.0065   -3.6497 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565    1.6862   -1.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047    1.4708   -0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576    1.3611    0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0335    1.3680    0.8263 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3929    1.2545    0.4789 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8547   -0.1229    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6352   -0.5217   -0.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0763   -1.8286   -0.9428 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7091   -2.7522   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1056   -4.0805   -0.1004 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9341   -2.4014    1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5675   -3.3648    2.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5131   -1.0914    1.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7091    2.1393   -0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7597    1.7990   -1.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0989    1.6099   -2.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0586    2.3333    1.4373 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4332    2.1489    2.7462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2721    2.5648    0.5785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2686    3.2162    1.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7843    1.2634    0.0526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3692    1.1060   -1.2582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5793   -1.9416   -0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3776   -3.0081   -0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7639   -2.8671   -0.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5885   -3.9153   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3646   -1.6581   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7389   -1.4738   -0.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5430   -0.6128    0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1063    0.6066    0.4707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1738   -0.7431    0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155   -1.6037   -0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581   -1.9040    1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7270    0.3635    1.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5643    1.0276    1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306    1.7639   -2.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0003    2.0831   -4.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4515    1.1913    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9675    1.6804    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9414    0.1803   -1.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6935   -2.0961   -1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6773   -4.3577   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0002   -3.1237    2.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8992   -0.7893    2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4047    3.1808   -0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7563    2.1317   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587    3.2058    1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427    2.7647    3.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9609    3.2613   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0673    4.1855    1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8960    1.2860    0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221    0.1871   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9360   -3.9625   -0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2597   -4.8482   -1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3808   -2.2037   -0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0890    0.8223    0.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5212    0.0878    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 31 33  1  0
 33 34  1  0
 33  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 41 43  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 27  1  0
 27 28  2  0
 27 26  1  0
 26 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 17 18  1  0
 18 25  2  0
 25 23  1  0
 23 24  1  0
 23 21  2  0
 21 22  1  0
 21 20  1  0
 20 19  2  0
  7 29  1  0
 29 30  1  0
 29 31  1  0
 43 35  1  0
 15  9  1  0
 19 18  1  0
 14 13  1  0
 32 62  1  0
 31 61  1  6
 33 63  1  6
 34 64  1  0
  5 46  1  1
  4 44  1  0
  4 45  1  0
 36 65  1  0
 38 66  1  0
 40 67  1  0
 42 68  1  0
 43 69  1  0
  7 47  1  1
 10 48  1  0
 12 49  1  0
 26 57  1  0
 26 58  1  0
 17 51  1  1
 15 50  1  0
 25 56  1  0
 24 55  1  0
 22 54  1  0
 20 53  1  0
 19 52  1  0
 29 59  1  1
 30 60  1  0
M  END


  Mrv0541 05061311302D          

 43 47  0  0  0  0            999 V2000
    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 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
   -3.5724   -2.8875    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
    1.4289    0.8250    0.0000 C   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
    4.2868    0.8250    0.0000 C   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
    5.0013   -0.4125    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    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
    2.1434    1.2375    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   -2.4750    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    0.0000    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
    0.0000   -2.4750    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
   -4.2868   -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  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
    1.4289   -1.6500    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  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
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   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
    0.7145   -0.4125    0.0000 O   0  0  0  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
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
 10  1  1  0  0  0  0
 10  3  2  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 13  2  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 17  4  1  0  0  0  0
 18  5  2  0  0  0  0
 19  8  1  0  0  0  0
 19 10  1  0  0  0  0
 20  7  2  0  0  0  0
 21  9  1  0  0  0  0
 22 15  2  0  0  0  0
 22 16  1  0  0  0  0
 22 20  1  0  0  0  0
 23 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24 21  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 11  1  0  0  0  0
 28 26  1  0  0  0  0
 29 13  1  0  0  0  0
 30 14  1  0  0  0  0
 31 15  1  0  0  0  0
 32 16  2  0  0  0  0
 33 17  1  0  0  0  0
 34 18  1  0  0  0  0
 35 23  1  0  0  0  0
 36 24  1  0  0  0  0
 37 25  1  0  0  0  0
 38 26  1  0  0  0  0
 39 27  2  0  0  0  0
 40  9  1  0  0  0  0
 40 27  1  0  0  0  0
 41 12  1  0  0  0  0
 41 28  1  0  0  0  0
 42 19  1  0  0  0  0
 42 20  1  0  0  0  0
 43 21  1  0  0  0  0
 43 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(O)C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC(O)=C(O)C=C2)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H26O15/c29-13-2-1-10(3-14(13)30)19-8-16(32)22-15(31)6-12(7-20(22)42-19)41-28-26(38)25(37)24(36)21(43-28)9-40-27(39)11-4-17(33)23(35)18(34)5-11/h1-7,19,21,24-26,28-31,33-38H,8-9H2

> <INCHI_KEY>
SHPCBRSOJXQRDY-UHFFFAOYSA-N

> <FORMULA>
C28H26O15

> <MOLECULAR_WEIGHT>
602.497

> <EXACT_MASS>
602.127170162

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
56.664445154548716

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
1.848078519

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.150861256869463

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.067591811780655

> <JCHEM_PKA_STRONGEST_BASIC>
-3.678965823839513

> <JCHEM_POLAR_SURFACE_AREA>
253.1299999999999

> <JCHEM_REFRACTIVITY>
141.1798

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.390   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      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -2.310   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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668  -2.310   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -4.620   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  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1   13                                                       
CONECT    3   10   14                                                       
CONECT    4   11   17                                                       
CONECT    5   11   18                                                       
CONECT    6   12   15                                                       
CONECT    7   12   20                                                       
CONECT    8   16   19                                                       
CONECT    9   21   40                                                       
CONECT   10    1    3   19                                                  
CONECT   11    4    5   27                                                  
CONECT   12    6    7   41                                                  
CONECT   13    2   14   29                                                  
CONECT   14    3   13   30                                                  
CONECT   15    6   22   31                                                  
CONECT   16    8   22   32                                                  
CONECT   17    4   23   33                                                  
CONECT   18    5   23   34                                                  
CONECT   19    8   10   42                                                  
CONECT   20    7   22   42                                                  
CONECT   21    9   24   43                                                  
CONECT   22   15   16   20                                                  
CONECT   23   17   18   35                                                  
CONECT   24   21   25   36                                                  
CONECT   25   24   26   37                                                  
CONECT   26   25   28   38                                                  
CONECT   27   11   39   40                                                  
CONECT   28   26   41   43                                                  
CONECT   29   13                                                            
CONECT   30   14                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
CONECT   33   17                                                            
CONECT   34   18                                                            
CONECT   35   23                                                            
CONECT   36   24                                                            
CONECT   37   25                                                            
CONECT   38   26                                                            
CONECT   39   27                                                            
CONECT   40    9   27                                                       
CONECT   41   12   28                                                       
CONECT   42   19   20                                                       
CONECT   43   21   28                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
(6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₈H₂₆O₁₅

Average Mass

602.4970 Da

Monoisotopic Mass

602.12717 Da

IUPAC Name

(6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

Traditional Name

(6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC1C(O)C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC(O)=C(O)C=C2)C1O

InChI Identifier

InChI=1S/C28H26O15/c29-13-2-1-10(3-14(13)30)19-8-16(32)22-15(31)6-12(7-20(22)42-19)41-28-26(38)25(37)24(36)21(43-28)9-40-27(39)11-4-17(33)23(35)18(34)5-11/h1-7,19,21,24-26,28-31,33-38H,8-9H2

InChI Key

SHPCBRSOJXQRDY-UHFFFAOYSA-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

Species Name	Source	Reference
Balanophora harlandii	LOTUS Database	35616633
Phyllanthus emblica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2-prenylated xanthones

Alternative Parents

Substituents

2-prenylated xanthone
Chromone
Anisole
Styrene
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Tertiary alcohol
Ether
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	1.5	ALOGPS
logP	1.85	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.07	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	253.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	141.18 m³·mol⁻¹	ChemAxon
Polarizability	56.66 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

HMDB0039921

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019583

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

74819398

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate (NP0213424)

MOL for NP0213424 ((6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D MOL for NP0213424 ((6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D SDF for NP0213424 ((6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0213424 ((6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

PDB for NP0213424 ((6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D PDB for NP0213424 ((6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

SMILES for NP0213424 ((6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

INCHI for NP0213424 ((6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

Structure for NP0213424 ((6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D Structure for NP0213424 ((6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)