NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0288731)

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Record Information

Version

2.0

Created at

2022-09-09 18:33:47 UTC

Updated at

2022-09-09 18:33:47 UTC

NP-MRD ID

NP0288731

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(2S,3R,4S,5R,6R)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2H-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol 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. (2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Vaccinium corymbosum and Vaccinium myrtillus. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2H-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092220332D          

 34 37  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
    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  2  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
    0.0000   -4.1250    0.0000 C   0  0  2  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
   -0.7145    2.0625    0.0000 O   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
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
  5 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    2.9331   -4.4453    1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6076   -3.7348    0.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3690   -2.4054   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174   -1.7435    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1636   -0.4211    0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1660    0.3944    1.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7764    1.6109    1.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3805    2.8477    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157    3.9418    1.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7295    5.1962    0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598    6.3014    1.3883 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6261    5.3043    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1032    4.1848   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1919    4.3484   -1.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2765    2.9480    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    1.7165   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0158    0.5226    0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6760   -0.6463   -0.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3011   -1.3684    0.9007 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9282   -2.5035    0.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1493   -2.3816   -0.0851 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9661   -2.0571   -1.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -1.9163   -2.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0946   -1.4435    0.5989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1056   -1.0182   -0.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4602   -0.2427    1.1997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5675    0.8532    0.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0827   -0.4165    1.7328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0580   -0.7260    3.0915 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596    0.2152   -0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7978   -0.4409   -1.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4879    0.2246   -2.4726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0651   -1.7731   -1.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0189   -2.4667   -1.9966 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8295   -4.2598    1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889   -5.5253    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3533   -4.1073    2.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8811   -2.2466    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9320   -0.1201    2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753    3.7984    2.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082    6.7754    2.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3498    6.2980   -0.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7943    3.6522   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707    1.7976   -0.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4400   -1.7063    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6272   -3.3934   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034   -2.8513   -2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3893   -1.1227   -1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3318   -0.9920   -2.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300   -2.0064    1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8684   -1.6766   -0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007    0.0783    2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424    0.9886    0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755    0.5912    1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361   -0.0234    3.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6712    1.2679   -0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1698   -0.2339   -3.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1728   -3.4416   -1.7822 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 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 33 34  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 33  3  1  0
 17  6  1  0
 28 19  1  0
 15  8  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
 30 56  1  0
 32 57  1  0
 34 58  1  0
  6 39  1  1
  9 40  1  0
 11 41  1  0
 12 42  1  0
 14 43  1  0
 16 44  1  0
 19 45  1  1
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  1
 25 51  1  0
 26 52  1  1
 27 53  1  0
 28 54  1  1
 29 55  1  0
M  END


  Mrv1652309092220332D          

 34 37  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
    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  2  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
    0.0000   -4.1250    0.0000 C   0  0  2  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
   -0.7145    2.0625    0.0000 O   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
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 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
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 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
  5 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288731

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(O)=C1O)C1OC2=CC(O)=CC(O)=C2C=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O12/c1-31-14-3-8(2-12(26)17(14)27)21-15(6-10-11(25)4-9(24)5-13(10)32-21)33-22-20(30)19(29)18(28)16(7-23)34-22/h2-6,16,18-30H,7H2,1H3/t16-,18+,19+,20-,21?,22-/m1/s1

> <INCHI_KEY>
JIHKBJWYHOVTJN-KGSSGPCFSA-N

> <FORMULA>
C22H24O12

> <MOLECULAR_WEIGHT>
480.422

> <EXACT_MASS>
480.126776213

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.63874170116709

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2H-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-0.3829564989999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.480314988385897

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.832373938161055

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810921633037086

> <JCHEM_POLAR_SURFACE_AREA>
198.76

> <JCHEM_REFRACTIVITY>
114.36960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2H-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-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  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   34  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   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7   17                                                  
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                                                       
CONECT   17   16    6   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28                                                            
CONECT   30    5   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₁₂

Average Mass

480.4220 Da

Monoisotopic Mass

480.12678 Da

IUPAC Name

(2S,3R,4S,5R,6R)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2H-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5R,6R)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2H-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(O)=C1O)C1OC2=CC(O)=CC(O)=C2C=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C22H24O12/c1-31-14-3-8(2-12(26)17(14)27)21-15(6-10-11(25)4-9(24)5-13(10)32-21)33-22-20(30)19(29)18(28)16(7-23)34-22/h2-6,16,18-30H,7H2,1H3/t16-,18+,19+,20-,21?,22-/m1/s1

InChI Key

JIHKBJWYHOVTJN-KGSSGPCFSA-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
Vaccinium corymbosum	LOTUS Database	35616633
Vaccinium myrtillus	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
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flav-3-ene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Methoxyphenol
Anisole
Catechol
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Secondary alcohol
Oxacycle
Ether
Polyol
Organoheterocyclic compound
Acetal
Primary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	-0.38	ChemAxon
pKa (Strongest Acidic)	8.83	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	198.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.37 m³·mol⁻¹	ChemAxon
Polarizability	45.64 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

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

57357857

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0288731)

MOL for NP0288731 ((2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0288731 ((2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0288731 ((2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0288731 ((2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0288731 ((2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0288731 ((2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0288731 ((2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0288731 ((2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0288731 ((2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0288731 ((2s,3r,4s,5r,6r)-2-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-2h-chromen-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)