NP-MRD: Showing NP-Card for 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one (NP0266349)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-08 10:40:06 UTC

Updated at

2022-09-08 10:40:06 UTC

NP-MRD ID

NP0266349

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one is found in Calendula officinalis. It was first documented in 2022 (PMID: 36104165). Based on a literature review a significant number of articles have been published on 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one (PMID: 36104164) (PMID: 36104163) (PMID: 36104162) (PMID: 36104161).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082212402D          

 44 48  0  0  1  0            999 V2000
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   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
   -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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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
    2.1434   -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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  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   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  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
    0.0000    0.8250    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
   -1.4289    0.8250    0.0000 C   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
  1  2  1  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  1  0  0  0  0
  6  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
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  6 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  1  0  0  0
 22 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 20 39  1  0  0  0  0
 39 40  1  1  0  0  0
  5 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
  3 43  1  0  0  0  0
 43 44  1  0  0  0  0
M  END

     RDKit          3D

 76 80  0  0  0  0  0  0  0  0999 V2000
   -6.0036    3.8408   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7166    4.2287   -0.6232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7885    3.2078   -0.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0314    1.9028   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0898    0.8708   -0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4716   -0.4911   -0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8019   -0.7497   -0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3091   -1.9208   -0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6774   -2.1644   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2395   -3.3902   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6062   -3.6271   -0.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4032   -4.4480    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0363   -4.2595    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1588   -5.3070    0.5428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4928   -2.9980    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401   -2.7666    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4033   -3.7341    0.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6005   -1.4858   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2471   -1.3195   -0.0519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130   -1.0290    1.1056 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1810    0.1402    1.0337 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432    0.0984    0.2306 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8088    1.5267    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8658    1.7923   -0.5922 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1193    1.4247   -0.4229 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9080    2.6220   -0.4040 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2043    2.3397   -0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3487    2.0479    1.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8734    1.2795   -0.8529 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6010    1.8362   -1.9107 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117    0.1745   -1.3549 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9393   -0.9274   -0.4989 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6593    0.7229   -1.6862 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7777   -0.1804   -2.2240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169   -0.7644    0.9466 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6372   -0.2163    2.1722 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7164   -2.1627    1.1076 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8420   -2.8110   -0.1017 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3313   -2.1586    1.6465 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4199   -1.9718    3.0502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8779    1.2415   -1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5940    2.5851   -1.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372    3.5590   -1.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173    4.8757   -1.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7245    4.6724   -0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4206    3.0031   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9010    3.4763    0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0008    1.6151   -0.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3198   -1.3225   -0.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3012   -2.9230   -0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8008   -5.4325    0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5570   -6.2319    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3019   -0.8719    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1197   -0.2417   -0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9556    2.2001   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904    1.8785    1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4466    0.8414    0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7791    3.2994   -0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3240    2.0361    1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9377    2.8112    1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8048    1.0654    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6496    0.7989   -0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7398    1.1008   -2.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4790   -0.2103   -2.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5988   -0.8648    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205    1.5054   -2.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -1.1106   -2.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107   -0.9423    0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968   -0.9747    2.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3972   -2.6854    1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3558   -2.2970   -0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311   -3.1093    1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4313   -1.5709    3.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784    0.5395   -1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6345    2.8795   -1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783    5.6317   -1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 41  2  0
 41 42  1  0
 42 43  2  0
 43 44  1  0
  5  6  1  0
  6 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 22 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
 43  3  1  0
  7  6  1  0
 39 20  1  0
  8 15  1  0
 33 25  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  4 48  1  0
 41 74  1  0
 42 75  1  0
 44 76  1  0
 20 53  1  1
 22 54  1  6
 23 55  1  0
 23 56  1  0
 25 57  1  1
 27 58  1  1
 28 59  1  0
 28 60  1  0
 28 61  1  0
 29 62  1  1
 30 63  1  0
 31 64  1  6
 32 65  1  0
 33 66  1  6
 34 67  1  0
 35 68  1  6
 36 69  1  0
 37 70  1  1
 38 71  1  0
 39 72  1  1
 40 73  1  0
 14 52  1  0
 12 51  1  0
 11 50  1  0
  9 49  1  0
M  END


  Mrv1652309082212402D          

 44 48  0  0  1  0            999 V2000
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   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
   -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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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
    2.1434   -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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  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   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  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
    0.0000    0.8250    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
   -1.4289    0.8250    0.0000 C   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
  1  2  1  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  1  0  0  0  0
  6  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
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  6 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  1  0  0  0
 22 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 20 39  1  0  0  0  0
 39 40  1  1  0  0  0
  5 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
  3 43  1  0  0  0  0
 43 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1=C(O[C@@H]2O[C@@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16-,18-,19+,21+,22-,23+,24+,27+,28-/m0/s1

> <INCHI_KEY>
UIDGLYUNOUKLBM-VSPWMBJUSA-N

> <FORMULA>
C28H32O16

> <MOLECULAR_WEIGHT>
624.548

> <EXACT_MASS>
624.16903495

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
58.42523869996061

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.7228669189999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.934067305727981

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.374288546780733

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648686043788379

> <JCHEM_POLAR_SURFACE_AREA>
254.51999999999995

> <JCHEM_REFRACTIVITY>
144.62740000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+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  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   43                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   41                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    6   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   39                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   25   34                                                  
CONECT   34   33                                                            
CONECT   35   22   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   20   40                                                  
CONECT   40   39                                                            
CONECT   41    5   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42    3   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₁₆

Average Mass

624.5480 Da

Monoisotopic Mass

624.16903 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1=C(O[C@@H]2O[C@@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16-,18-,19+,21+,22-,23+,24+,27+,28-/m0/s1

InChI Key

UIDGLYUNOUKLBM-VSPWMBJUSA-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
Calendula officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
1-benzopyran
Methoxyphenol
Benzopyran
Phenol ether
Phenoxy compound
Anisole
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	-0.72	ChemAxon
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	254.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	144.63 m³·mol⁻¹	ChemAxon
Polarizability	58.43 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

97543949

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bamat NA, Orians CM, Abbasi S, Morley CJ, Ross Russell R, Panitch HB, Handley SC, Foglia EE, Posencheg MA, Kirpalani H: Use of ventilation/perfusion mismatch to guide individualised CPAP level selection in preterm infants: a feasibility trial. Arch Dis Child Fetal Neonatal Ed. 2022 Sep 14. pii: archdischild-2022-324474. doi: 10.1136/archdischild-2022-324474. [PubMed:36104165 ]
Kopel D, Gottschalk CH: The Epidemiology of Primary Headache Disorders. Semin Neurol. 2022 Sep 14. doi: 10.1055/a-1942-6823. [PubMed:36104164 ]
Cleary NM, O'Gorman A: Hyaluronidase for localised infusion site reaction during continuous subcutaneous infusion. BMJ Support Palliat Care. 2022 Sep 14. pii: spcare-2022-003909. doi: 10.1136/spcare-2022-003909. [PubMed:36104163 ]
Hayes J, Waldron D, Levins KJ, Gaffney L, Azhar M, Beatty S, Mannion E: Methadone prescribed as an analgesic by a specialist palliative medicine team in an acute hospital inpatient setting: retrospective study. BMJ Support Palliat Care. 2022 Sep 14. pii: spcare-2022-003586. doi: 10.1136/spcare-2022-003586. [PubMed:36104162 ]
Peiro I, Milla J, Arribas L, Hurtos L, Gonzalez-Tampan AR, Bellver M, Fort E, Molina-Mata K, Joudanin JR, Valcarcel J, Gonzalez-Barboteo J: Venting percutaneous radiologic gastrostomy in malignant bowel obstruction: safety and effectiveness in a comprehensive cancer centre. BMJ Support Palliat Care. 2022 Sep 14. pii: spcare-2022-003895. doi: 10.1136/spcare-2022-003895. [PubMed:36104161 ]
LOTUS database [Link]

Showing NP-Card for 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one (NP0266349)

MOL for NP0266349 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0266349 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0266349 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0266349 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0266349 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0266349 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0266349 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0266349 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0266349 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0266349 (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one)