Np mrd loader

Showing NP-Card for Peonidin 3-(2-(6-(E)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-beta-D-glucoside (NP0339438)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-11 21:51:23 UTC
Updated at2024-09-11 21:51:24 UTC
NP-MRD IDNP0339438
Secondary Accession NumbersNone
Natural Product Identification
Common NamePeonidin 3-(2-(6-(E)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-beta-D-glucoside
DescriptionNaringenin 4'-O-glucuronide belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid. Naringenin 4'-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339438 (Peonidin 3-(2-(6-(E)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-beta-D-glucoside)


  Mrv0541 02271201312D          

 67 73  0  0  1  0            999 V2000
    1.4289    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.4000    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158   -1.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -1.7250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2869   -1.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2869   -0.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4303   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4303   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -1.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.7250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.7250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4290   -0.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1435    0.7501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.0749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -6.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -5.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.4999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303   -6.6749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.1999    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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 21  1  0  0  0  0
 27 15  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  6  0  0  0
 25 29  1  1  0  0  0
 24 30  1  6  0  0  0
 23 31  1  1  0  0  0
 31 32  1  0  0  0  0
 11 33  1  0  0  0  0
 39 33  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 39  1  0  0  0  0
 38 40  1  6  0  0  0
 37 41  1  1  0  0  0
 36 42  1  6  0  0  0
 35 43  1  1  0  0  0
 43 44  1  0  0  0  0
 50 40  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 45 50  1  0  0  0  0
 49 51  1  6  0  0  0
 48 52  1  1  0  0  0
 47 53  1  6  0  0  0
 46 54  1  1  0  0  0
 54 55  1  0  0  0  0
 66 55  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 56 61  1  0  0  0  0
 57 62  1  0  0  0  0
 58 63  1  0  0  0  0
 61 64  1  0  0  0  0
 64 65  2  0  0  0  0
 65 66  1  0  0  0  0
 66 67  2  0  0  0  0
M  CHG  1  21   1
M  END
Download

3D MOL for NP0339438 (Peonidin 3-(2-(6-(E)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-beta-D-glucoside)

Download
3D SDF for NP0339438 (Peonidin 3-(2-(6-(E)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-beta-D-glucoside)

  Mrv0541 02271201312D          

 67 73  0  0  1  0            999 V2000
    1.4289    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.4000    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158   -1.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -1.7250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2869   -1.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2869   -0.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4303   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4303   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -1.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.7250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.7250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4290   -0.4875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1435    0.7501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.0749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -6.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -5.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.4999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4303   -6.6749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.1999    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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 21  1  0  0  0  0
 27 15  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  6  0  0  0
 25 29  1  1  0  0  0
 24 30  1  6  0  0  0
 23 31  1  1  0  0  0
 31 32  1  0  0  0  0
 11 33  1  0  0  0  0
 39 33  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 39  1  0  0  0  0
 38 40  1  6  0  0  0
 37 41  1  1  0  0  0
 36 42  1  6  0  0  0
 35 43  1  1  0  0  0
 43 44  1  0  0  0  0
 50 40  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 45 50  1  0  0  0  0
 49 51  1  6  0  0  0
 48 52  1  1  0  0  0
 47 53  1  6  0  0  0
 46 54  1  1  0  0  0
 54 55  1  0  0  0  0
 66 55  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 56 61  1  0  0  0  0
 57 62  1  0  0  0  0
 58 63  1  0  0  0  0
 61 64  1  0  0  0  0
 64 65  2  0  0  0  0
 65 66  1  0  0  0  0
 66 67  2  0  0  0  0
M  CHG  1  21   1
M  END
> <DATABASE_ID>
NP0339438

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](COC(=O)\C=C\C3=CC=C(O)C(O)=C3)[C@@H](O)[C@H](O)[C@H]2O)C=C2C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=CC2=[O+]1

> <INCHI_IDENTIFIER>
InChI=1S/C43H48O24/c1-59-25-9-17(4-6-21(25)48)39-26(12-19-23(61-39)10-18(46)11-24(19)62-41-37(57)34(54)31(51)27(13-44)64-41)63-43-40(36(56)32(52)28(14-45)65-43)67-42-38(58)35(55)33(53)29(66-42)15-60-30(50)7-3-16-2-5-20(47)22(49)8-16/h2-12,27-29,31-38,40-45,51-58H,13-15H2,1H3,(H3-,46,47,48,49,50)/p+1/t27-,28-,29-,31-,32-,33-,34+,35+,36+,37-,38-,40-,41-,42+,43-/m1/s1

> <INCHI_KEY>
HFNKXOBZVJNMRG-FRWPPZSRSA-O

> <FORMULA>
C43H49O24

> <MOLECULAR_WEIGHT>
949.8348

> <EXACT_MASS>
949.261377496

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
90.71925932456776

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
-1.2320000000000046

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.337462644727445

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.660263281523082

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6789468869085615

> <JCHEM_POLAR_SURFACE_AREA>
387.27000000000004

> <JCHEM_REFRACTIVITY>
228.82700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339438 (Peonidin 3-(2-(6-(E)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-beta-D-glucoside)
Download
PDB for NP0339438 (Peonidin 3-(2-(6-(E)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-beta-D-glucoside)
HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0       2.667   2.170   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667   3.710   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   4.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   6.020   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   6.790   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   6.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   6.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   4.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   3.710   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   3.710   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   2.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   1.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   2.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668   1.400   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.668  -0.140   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -8.002   2.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   3.710   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.336   4.480   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.668   4.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335   3.710   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001   4.480   0.000  0.00  0.00           O+1
HETATM   22  O   UNK     0      -9.336  -0.140   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -10.669  -0.910   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.669  -2.450   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.336  -3.220   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.002  -2.450   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.002  -0.910   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.668  -3.220   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -9.336  -4.760   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0     -12.003  -3.220   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -12.003  -0.140   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -13.337  -0.910   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.334   1.400   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -2.667  -0.910   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.667  -2.450   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.334  -3.220   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000  -2.450   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000  -0.910   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.334  -0.140   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.334  -0.140   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       1.334  -3.220   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -1.334  -4.760   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -4.001  -3.220   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -4.001  -4.760   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       2.667  -2.450   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       4.001  -3.220   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.335  -2.450   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       5.335  -0.910   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.001  -0.140   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       2.667  -0.910   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       4.001   1.400   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       6.668  -0.140   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       6.668  -3.220   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       4.001  -4.760   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       5.335  -5.530   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       8.002 -11.690   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       9.336 -12.460   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      10.669 -11.690   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      10.669 -10.150   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       9.336  -9.380   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       8.002 -10.150   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       9.336 -14.000   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      12.003 -12.460   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0       6.668  -9.380   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       6.668  -7.840   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       5.335  -7.070   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       4.001  -7.840   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   21                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   27                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13   21                                                  
CONECT   21   20   10                                                       
CONECT   22   23   27                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   15   26   22                                                  
CONECT   28   26                                                            
CONECT   29   25                                                            
CONECT   30   24                                                            
CONECT   31   23   32                                                       
CONECT   32   31                                                            
CONECT   33   11   39                                                       
CONECT   34   35   39                                                       
CONECT   35   34   36   43                                                  
CONECT   36   35   37   42                                                  
CONECT   37   36   38   41                                                  
CONECT   38   37   39   40                                                  
CONECT   39   33   38   34                                                  
CONECT   40   38   50                                                       
CONECT   41   37                                                            
CONECT   42   36                                                            
CONECT   43   35   44                                                       
CONECT   44   43                                                            
CONECT   45   46   50                                                       
CONECT   46   45   47   54                                                  
CONECT   47   46   48   53                                                  
CONECT   48   47   49   52                                                  
CONECT   49   48   50   51                                                  
CONECT   50   40   49   45                                                  
CONECT   51   49                                                            
CONECT   52   48                                                            
CONECT   53   47                                                            
CONECT   54   46   55                                                       
CONECT   55   54   66                                                       
CONECT   56   57   61                                                       
CONECT   57   56   58   62                                                  
CONECT   58   57   59   63                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   56   64                                                  
CONECT   62   57                                                            
CONECT   63   58                                                            
CONECT   64   61   65                                                       
CONECT   65   64   66                                                       
CONECT   66   55   65   67                                                  
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  146    0
END

Download
3D PDB for NP0339438 (Peonidin 3-(2-(6-(E)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-beta-D-glucoside)
Download
SMILES for NP0339438 (Peonidin 3-(2-(6-(E)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-beta-D-glucoside)
COC1=C(O)C=CC(=C1)C1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](COC(=O)\C=C\C3=CC=C(O)C(O)=C3)[C@@H](O)[C@H](O)[C@H]2O)C=C2C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=CC2=[O+]1
Download
INCHI for NP0339438 (Peonidin 3-(2-(6-(E)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-beta-D-glucoside)
InChI=1S/C43H48O24/c1-59-25-9-17(4-6-21(25)48)39-26(12-19-23(61-39)10-18(46)11-24(19)62-41-37(57)34(54)31(51)27(13-44)64-41)63-43-40(36(56)32(52)28(14-45)65-43)67-42-38(58)35(55)33(53)29(66-42)15-60-30(50)7-3-16-2-5-20(47)22(49)8-16/h2-12,27-29,31-38,40-45,51-58H,13-15H2,1H3,(H3-,46,47,48,49,50)/p+1/t27-,28-,29-,31-,32-,33-,34+,35+,36+,37-,38-,40-,41-,42+,43-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
Peonidin 3-O-(2-O-(6-O-(e)-caffeoyl-beta-D-glucosyl)-beta-D-glucoside) 5-O-beta-D-glucosideHMDB
Peonidin 3-(2-(6-(e)-caffeoyl-b-D-glucosyl)-b-D-glucoside) 5-b-D-glucosideGenerator
Peonidin 3-(2-(6-(e)-caffeoyl-β-D-glucosyl)-β-D-glucoside) 5-β-D-glucosideGenerator
Chemical FormulaC43H49O24
Average Mass949.8348 Da
Monoisotopic Mass949.26138 Da
IUPAC Name3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
Traditional Name3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(=C1)C1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](COC(=O)\C=C\C3=CC=C(O)C(O)=C3)[C@@H](O)[C@H](O)[C@H]2O)C=C2C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=CC2=[O+]1
InChI Identifier
InChI=1S/C43H48O24/c1-59-25-9-17(4-6-21(25)48)39-26(12-19-23(61-39)10-18(46)11-24(19)62-41-37(57)34(54)31(51)27(13-44)64-41)63-43-40(36(56)32(52)28(14-45)65-43)67-42-38(58)35(55)33(53)29(66-42)15-60-30(50)7-3-16-2-5-20(47)22(49)8-16/h2-12,27-29,31-38,40-45,51-58H,13-15H2,1H3,(H3-,46,47,48,49,50)/p+1/t27-,28-,29-,31-,32-,33-,34+,35+,36+,37-,38-,40-,41-,42+,43-/m1/s1
InChI KeyHFNKXOBZVJNMRG-FRWPPZSRSA-O
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentFlavonoid O-glucuronides  
Alternative Parents
Substituents
  • Flavonoid-4p-o-glucuronide
    • 

  • Flavanone
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Hydroxyflavonoid
    • 

  • Flavan
    • 

  • Phenolic glycoside
    • 

  • 1-o-glucuronide
    • 

  • O-glucuronide
    • 

  • Glucuronic acid or derivatives
    • 

  • Hexose monosaccharide
    • 

  • Glycosyl compound
    • 

  • Chromone
    • 

  • O-glycosyl compound
    • 

  • Chromane
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Phenol ether
    • 

  • Aryl ketone
    • 

  • Phenoxy compound
    • 

  • Aryl alkyl ketone
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Beta-hydroxy acid
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Pyran
    • 

  • Oxane
    • 

  • Benzenoid
    • 

  • Hydroxy acid
    • 

  • Monosaccharide
    • 

  • Monocyclic benzene moiety
    • 

  • Vinylogous acid
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Acetal
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.98ALOGPS
logP-1.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area387.27 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity228.83 m³·mol⁻¹ChemAxon
Polarizability90.72 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0041759  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029929  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91312540  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References