NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0299771)

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Record Information

Version

2.0

Created at

2022-09-10 11:47:25 UTC

Updated at

2022-09-10 11:47:25 UTC

NP-MRD ID

NP0299771

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

Description

Quercetagetin 7-methyl ether 3-glucoside 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. Thus, quercetagetin 7-methyl ether 3-glucoside is considered to be a flavonoid. 2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Paepalanthus vellozioides. Based on a literature review very few articles have been published on Quercetagetin 7-methyl ether 3-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102213472D          

 35 38  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
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -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
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  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
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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  2  0  0  0  0
 11 12  1  0  0  0  0
 11 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
  7 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
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 18 27  1  0  0  0  0
 27 28  1  6  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  3 34  2  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    6.8909   -1.6449   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9340   -2.6335   -0.4202 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5728   -2.4042   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130   -1.1203   -0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -0.8036   -0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3565    0.4248   -0.2074 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0560    0.7971   -0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7866    2.2124   -0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947    2.8547   -0.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733    4.2191   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509    4.9604    0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3133    6.3260    0.7664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6400    4.3569    0.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6723    5.1300    1.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    3.0209    0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012   -0.1334   -0.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2434    0.1268   -0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286   -0.0229    0.6868 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5742   -1.3196    0.6860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7871   -1.4399    0.0883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8088   -2.7323   -0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0341   -2.9164   -1.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1397   -0.3227   -0.8571 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4557   -0.5343   -1.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1018    1.0313   -0.1876 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8861    2.0330   -1.1309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0710    0.9987    0.9092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7722    0.5920    2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5211   -1.4666   -0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421   -2.3272   -0.8304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391   -1.8110   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2842   -3.1009   -0.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407   -4.1150   -0.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6432   -3.3935   -0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0587   -4.7056   -0.8810 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0099   -0.9509   -1.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8535   -2.0760    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5462   -1.0014    0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -0.2894   -0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2096    2.3322   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119    4.7125   -0.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0762    6.8572    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5618    4.7066    1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7429    2.5681    0.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -0.0376    1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6247   -1.5216    0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5799   -3.5986   -0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881   -2.6881   -1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779   -3.8887   -1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018   -0.3330   -1.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5293   -0.6723   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0835    1.2822    0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7409    2.4134   -1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745    1.9845    1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652    0.0923    2.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811   -5.0724   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0382   -4.9552   -0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 34  2  0
 34 35  1  0
 34 32  1  0
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 32 31  2  0
 31 29  1  0
 29 30  2  0
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 17 18  1  0
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 19 20  1  0
 20 21  1  0
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 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 16  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  4  3  1  0
 15  8  1  0
  5 31  1  0
 27 18  1  0
  1 36  1  0
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  1 38  1  0
 35 57  1  0
 33 56  1  0
 18 45  1  1
 20 46  1  1
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  6
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 25 52  1  1
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 27 54  1  1
 28 55  1  0
  4 39  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 14 43  1  0
 15 44  1  0
M  END


  Mrv1652309102213472D          

 35 38  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
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -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
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  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
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
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 16 17  1  0  0  0  0
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 18 19  1  0  0  0  0
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 23 25  1  0  0  0  0
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 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  2  0  0  0  0
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  3 34  2  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0299771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C(O)=C2C(=O)C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(OC2=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O13/c1-32-11-5-10-13(16(28)14(11)26)17(29)21(20(33-10)7-2-3-8(24)9(25)4-7)35-22-19(31)18(30)15(27)12(6-23)34-22/h2-5,12,15,18-19,22-28,30-31H,6H2,1H3/t12-,15-,18+,19-,22+/m1/s1

> <INCHI_KEY>
AGKJZAUTPQSZRO-VWGICKAWSA-N

> <FORMULA>
C22H22O13

> <MOLECULAR_WEIGHT>
494.405

> <EXACT_MASS>
494.106040768

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.45536449728491

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <JCHEM_LOGP>
-0.30250656166666734

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.58382431331282

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.35688550186622

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98109237118166

> <JCHEM_POLAR_SURFACE_AREA>
215.82999999999998

> <JCHEM_REFRACTIVITY>
115.73870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -0.770   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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8                                                       
CONECT   16    7   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    5   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₃

Average Mass

494.4050 Da

Monoisotopic Mass

494.10604 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(O)=C2C(=O)C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(OC2=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C22H22O13/c1-32-11-5-10-13(16(28)14(11)26)17(29)21(20(33-10)7-2-3-8(24)9(25)4-7)35-22-19(31)18(30)15(27)12(6-23)34-22/h2-5,12,15,18-19,22-28,30-31H,6H2,1H3/t12-,15-,18+,19-,22+/m1/s1

InChI Key

AGKJZAUTPQSZRO-VWGICKAWSA-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
Paepalanthus vellozioides	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
7-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
6-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Phenol
Monosaccharide
Pyran
Monocyclic benzene moiety
Benzenoid
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Primary alcohol
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.3	ChemAxon
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	215.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.74 m³·mol⁻¹	ChemAxon
Polarizability	46.46 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00005651

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

100978776

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0299771)

MOL for NP0299771 (2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0299771 (2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0299771 (2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0299771 (2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0299771 (2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0299771 (2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0299771 (2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0299771 (2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0299771 (2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0299771 (2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)