NP-MRD: Showing NP-Card for 3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one (NP0249164)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 11:38:58 UTC

Updated at

2022-09-07 11:38:58 UTC

NP-MRD ID

NP0249164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

CHEMBL1929194 belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. 3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one is found in Lotus edulis. Based on a literature review very few articles have been published on CHEMBL1929194.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072213382D          

 40 44  0  0  1  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  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
    0.7145   -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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.8579    0.8250    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 O   0  0  0  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
    3.6194    1.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    2.0945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6131    2.9150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5063    2.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0583    1.6530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9543    1.3099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7389    1.0550    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
    4.2868   -1.6500    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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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   -1.6500    0.0000 C   0  0  2  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
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  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
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 13 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 10 33  1  0  0  0  0
 33 34  2  0  0  0  0
  6 34  1  0  0  0  0
  4 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  1  0  0  0
M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
   -6.8800    0.4325   -2.6767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3121    0.2124   -1.2796 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5991   -0.9845   -1.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8929   -1.0429   -0.0722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3309    0.2091    0.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998    0.5027    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6457    1.8338    0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062    2.1864    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0381    3.5122    0.7870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175    1.2031    0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0067    1.5117    0.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894    2.6859    0.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711    0.4820    0.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031    0.8334    0.9451 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0732    1.2874   -0.1749 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4068    2.6173    0.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6890    2.8674   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2017    1.6803   -1.0647 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8746    1.7709   -2.4036 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6704    1.4186   -0.8575 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3623    2.4836   -1.4318 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3487    0.5865   -0.4185 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2283   -0.4892   -1.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676   -0.8014    0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4400   -1.9679    0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7378   -2.0160    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5301   -3.1714    0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0295   -4.3352    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7884   -5.4903    0.2962 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229   -4.2980   -0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9485   -3.1668    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591   -1.0341    0.4608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6654   -0.1368    0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0098   -0.4518    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509   -1.3740    0.9677 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6759   -2.4607    0.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8434   -0.1464    1.0788 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7903   -0.2857    2.0744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4293    0.1214   -0.2751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.0777    1.3443   -0.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0799    0.2361   -3.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7527   -0.2334   -2.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2299    1.4805   -2.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6555    1.0702   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1712   -1.8609   -0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031    2.5996    0.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682    4.0673    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4404    1.2192   -1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7299    3.7659   -0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3524    3.1489    0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919    2.6896   -2.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9227    0.5221   -1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9521    1.2998    0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4273    3.2653   -0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667    0.2748    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7759   -0.1278   -2.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1672   -1.1224    1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5520   -3.1485    1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3247   -5.6372   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -5.2112   -0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9094   -3.1585   -0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423   -1.5123    0.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5182   -1.6244    1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4266   -2.6137    1.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1638    0.7063    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6649    0.4300    2.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1166   -0.6991   -0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4133    2.0440   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 13 24  2  0
 24 32  1  0
 32 33  1  0
 33 34  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
  4 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39  2  1  0
 34  6  1  0
 31 25  1  0
 33 10  1  0
 22 15  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  2 44  1  1
  4 45  1  6
  7 46  1  0
  9 47  1  0
 15 48  1  6
 17 49  1  0
 17 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  1
 23 56  1  0
 34 62  1  0
 26 57  1  0
 27 58  1  0
 29 59  1  0
 30 60  1  0
 31 61  1  0
 35 63  1  1
 36 64  1  0
 37 65  1  1
 38 66  1  0
 39 67  1  6
 40 68  1  0
M  END


  Mrv1652309072213382D          

 40 44  0  0  1  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  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
    0.7145   -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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.8579    0.8250    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 O   0  0  0  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
    3.6194    1.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    2.0945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6131    2.9150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5063    2.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0583    1.6530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9543    1.3099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7389    1.0550    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
    4.2868   -1.6500    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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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   -1.6500    0.0000 C   0  0  2  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
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  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
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 13 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 10 33  1  0  0  0  0
 33 34  2  0  0  0  0
  6 34  1  0  0  0  0
  4 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0249164

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@H]4OC[C@@](O)(CO)[C@@H]4O)=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O14/c1-10-17(30)19(32)20(33)24(37-10)38-13-6-14(29)16-15(7-13)39-21(11-2-4-12(28)5-3-11)22(18(16)31)40-25-23(34)26(35,8-27)9-36-25/h2-7,10,17,19-20,23-25,27-30,32-35H,8-9H2,1H3/t10-,17-,19+,20+,23+,24-,25+,26-/m0/s1

> <INCHI_KEY>
SVQKJHRWPYLYKM-IFHXNFKFSA-N

> <FORMULA>
C26H28O14

> <MOLECULAR_WEIGHT>
564.496

> <EXACT_MASS>
564.147905582

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.97435267265945

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.5680915153333327

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.556661715740743

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.083345775704748

> <JCHEM_PKA_STRONGEST_BASIC>
-3.142388183026722

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999995

> <JCHEM_REFRACTIVITY>
132.15220000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.756   2.445   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.232   3.910   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.772   3.910   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.611   5.441   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.278   4.230   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.309   3.086   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.248   2.445   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.713   1.969   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   35                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   33                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   22                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   18   15   23                                                  
CONECT   23   22                                                            
CONECT   24   13   25   32                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
CONECT   32   24   33                                                       
CONECT   33   32   10   34                                                  
CONECT   34   33    6                                                       
CONECT   35    4   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    2   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₁₄

Average Mass

564.4960 Da

Monoisotopic Mass

564.14791 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@H]4OC[C@@](O)(CO)[C@@H]4O)=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H28O14/c1-10-17(30)19(32)20(33)24(37-10)38-13-6-14(29)16-15(7-13)39-21(11-2-4-12(28)5-3-11)22(18(16)31)40-25-23(34)26(35,8-27)9-36-25/h2-7,10,17,19-20,23-25,27-30,32-35H,8-9H2,1H3/t10-,17-,19+,20+,23+,24-,25+,26-/m0/s1

InChI Key

SVQKJHRWPYLYKM-IFHXNFKFSA-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
Lotus edulis	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Pyran
Monocyclic benzene moiety
Oxane
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Oxolane
Vinylogous acid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
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	-0.57	ChemAxon
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	132.15 m³·mol⁻¹	ChemAxon
Polarizability	53.97 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

28430074

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25067849

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one (NP0249164)

MOL for NP0249164 (3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0249164 (3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0249164 (3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0249164 (3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

PDB for NP0249164 (3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0249164 (3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

SMILES for NP0249164 (3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

INCHI for NP0249164 (3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

Structure for NP0249164 (3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0249164 (3-{[(2r,3s,4s)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)