NP-MRD: Showing NP-Card for 5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid (NP0052792)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 23:43:17 UTC

Updated at

2022-04-27 23:43:17 UTC

NP-MRD ID

NP0052792

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid

Description

6-Hydroxyapigenin 7-glucuronosyl-(1->2)-glucuronide belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Thus, 6-hydroxyapigenin 7-glucuronosyl-(1->2)-glucuronide is considered to be a flavonoid. 5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid is found in Perilla ocimoides. Based on a literature review very few articles have been published on 6-hydroxyapigenin 7-glucuronosyl-(1->2)-glucuronide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201432D          

 45 49  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   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    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  2  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
   -4.2868    3.3000    0.0000 C   0  0  0  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
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
  3 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  6  0  0  0
 24 32  1  1  0  0  0
 23 33  1  6  0  0  0
 34 33  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 34 40  1  0  0  0  0
 39 41  1  1  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 36 44  1  1  0  0  0
 35 45  1  6  0  0  0
M  END

     RDKit          3D

 71 75  0  0  0  0  0  0  0  0999 V2000
   -2.5448   -3.6058   -4.5858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1059   -4.1526   -3.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8447   -5.3132   -3.7542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -3.5166   -2.2753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1569   -2.3597   -2.3532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818   -2.0983   -1.0117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7550   -1.2081   -1.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597   -1.3367   -0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4037   -0.2120   -0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7328   -0.2184   -0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4818    0.8600   -0.6392 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584    0.8992   -0.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4835    2.1688   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7851    3.2892   -0.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4281    4.4968   -1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7790    4.6377   -0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4073    5.8575   -1.0461 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4599    3.5155   -0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8325    2.2926   -0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3783   -0.2412    0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6430   -1.4208    0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524   -2.5012    0.5859 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3046   -1.3900   -0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5156   -2.5510    0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362   -3.7019    0.4485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1759   -2.4945   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4187   -3.6322   -0.1712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0219   -1.5308   -0.2736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5792   -1.1471    0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6539    0.2112    1.1963 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3922    0.7784    1.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4096    2.1535    1.2586 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1015    2.6672    1.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167    1.9350    2.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481    4.0313    1.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993    2.8604    1.9665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9530    3.9002    1.1196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6809    2.0643    2.3622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2147    2.5089    3.5889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4499    0.5739    2.4456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6584   -0.0869    2.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465   -2.6173   -0.2711 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2951   -2.1737    0.1813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2704   -3.0963   -1.6972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2353   -4.0934   -1.7628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8997   -5.9780   -2.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3936   -4.2085   -1.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337   -3.0818   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    0.7145   -1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    3.2400   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9035    5.4044   -1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8034    6.1378   -1.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5334    3.5706   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4198    1.4460    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4306   -0.2630    0.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6618   -4.5639    0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7830   -4.5009    0.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3700   -0.6789   -0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0708    0.7633    0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4206    2.3520    0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6517    4.6465    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1257    3.3995    2.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9395    3.9300    1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199    2.1942    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7653    3.3347    3.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8060    0.4018    3.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4712   -0.9923    2.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6662   -3.4567    0.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8670   -1.8680   -0.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6211   -2.1991   -2.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1833   -4.7462   -1.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 38  1  0
 38 40  1  0
 40 41  1  0
 40 30  1  0
 30 29  1  0
 29 28  1  0
 28 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 44  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 26  2  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 23  2  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 12  2  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 30 31  1  0
 31 32  1  0
 32 36  1  0
 36 37  1  0
 32 33  1  0
 33 35  1  0
 33 34  2  0
 36 38  1  0
  6 28  1  0
  9  8  1  0
 19 13  1  0
 10 23  1  0
 39 65  1  0
 38 64  1  6
 40 66  1  1
 41 67  1  0
 30 59  1  6
 28 58  1  6
 42 68  1  1
 43 69  1  0
 44 70  1  6
 45 71  1  0
  4 47  1  1
  6 48  1  1
 27 57  1  0
 25 56  1  0
 20 55  1  0
  9 49  1  0
 14 50  1  0
 15 51  1  0
 17 52  1  0
 18 53  1  0
 19 54  1  0
  3 46  1  0
 32 60  1  6
 36 62  1  1
 37 63  1  0
 35 61  1  0
M  END


  Mrv1652304282201432D          

 45 49  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   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    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  2  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
   -4.2868    3.3000    0.0000 C   0  0  0  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
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
  3 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  6  0  0  0
 24 32  1  1  0  0  0
 23 33  1  6  0  0  0
 34 33  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 34 40  1  0  0  0  0
 39 41  1  1  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 36 44  1  1  0  0  0
 35 45  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052792

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H](O[C@H]2OC2=C(O)C(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)C(O)=O)O[C@@H]([C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O18/c28-8-3-1-7(2-4-8)10-5-9(29)13-11(41-10)6-12(14(30)15(13)31)42-27-23(19(35)18(34)22(44-27)25(39)40)45-26-20(36)16(32)17(33)21(43-26)24(37)38/h1-6,16-23,26-28,30-36H,(H,37,38)(H,39,40)/t16-,17-,18-,19-,20+,21-,22-,23+,26-,27+/m0/s1

> <INCHI_KEY>
IBLZNWWZRXJQAK-DBFWEQBMSA-N

> <FORMULA>
C27H26O18

> <MOLECULAR_WEIGHT>
638.487

> <EXACT_MASS>
638.111913997

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
59.00509633451247

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
-0.995230851

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.145294707465744

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.518064127125469

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9485410726340797

> <JCHEM_POLAR_SURFACE_AREA>
299.65999999999997

> <JCHEM_REFRACTIVITY>
139.1873

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001   3.850   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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -9.336   6.930   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19    3                                                            
CONECT   20    2                                                            
CONECT   21    1   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   33                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25                                                            
CONECT   32   24                                                            
CONECT   33   23   34                                                       
CONECT   34   33   35   40                                                  
CONECT   35   34   36   45                                                  
CONECT   36   35   37   44                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39   34                                                       
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   36                                                            
CONECT   45   35                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₆O₁₈

Average Mass

638.4870 Da

Monoisotopic Mass

638.11191 Da

IUPAC Name

(2S,3S,4S,5R,6S)-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H](O[C@H]2OC2=C(O)C(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)C(O)=O)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C27H26O18/c28-8-3-1-7(2-4-8)10-5-9(29)13-11(41-10)6-12(14(30)15(13)31)42-27-23(19(35)18(34)22(44-27)25(39)40)45-26-20(36)16(32)17(33)21(43-26)24(37)38/h1-6,16-23,26-28,30-36H,(H,37,38)(H,39,40)/t16-,17-,18-,19-,20+,21-,22-,23+,26-,27+/m0/s1

InChI Key

IBLZNWWZRXJQAK-DBFWEQBMSA-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
Perilla ocimoides	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glucuronides

Alternative Parents

Substituents

Flavonoid-7-o-glucuronide
Flavonoid-7-o-glycoside
Hydroxyflavonoid
Flavone
6-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Phenolic glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Pyran
Hydroxy acid
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
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	0.92	ALOGPS
logP	-1	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.52	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	299.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.19 m³·mol⁻¹	ChemAxon
Polarizability	59.01 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

C00004488

Chemspider ID

103885158

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102158504

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid (NP0052792)

MOL for NP0052792 (5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid)

3D MOL for NP0052792 (5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid)

3D SDF for NP0052792 (5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid)

3D-SDF for NP0052792 (5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid)

PDB for NP0052792 (5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid)

3D PDB for NP0052792 (5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid)

SMILES for NP0052792 (5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid)

INCHI for NP0052792 (5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid)

Structure for NP0052792 (5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid)

3D Structure for NP0052792 (5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-Glucopyranosiduronic acid)