NP-MRD: Showing NP-Card for 3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium (NP0204030)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 23:37:44 UTC

Updated at

2022-09-04 23:37:44 UTC

NP-MRD ID

NP0204030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

Description

Cyanidin 3-O-(2-O-beta-D-glucuronosyl)-beta-D-glucoside belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. Thus, cyanidin 3-O-(2-O-beta-D-glucuronosyl)-beta-D-glucoside is considered to be a flavonoid. Cyanidin 3-O-(2-O-beta-D-glucuronosyl)-beta-D-glucoside is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium is found in Apis cerana. Based on a literature review very few articles have been published on cyanidin 3-O-(2-O-beta-D-glucuronosyl)-beta-D-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201372D          

 44 48  0  0  1  0            999 V2000
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  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
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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 O   0  3  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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
   -2.1434   -1.2375    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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
   -2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  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
 21 22  1  0  0  0  0
 11 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 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
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  1  1  0  0  0
  6 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
  4 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  CHG  1  21   1
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
    2.0431    4.2978    1.2519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359    3.3491    1.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0486    3.4859    3.1145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8948    2.1080    1.0786 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4185    2.1329   -0.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6222    0.9081   -0.7967 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8114    0.5661   -1.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0674   -0.5653   -1.6936 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3975   -0.1595   -1.7572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1119   -0.6539   -0.6687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122   -0.0243    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6788    1.3708    0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2954    2.0098    1.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848    3.4033    1.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6302    4.1638    0.6579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9103    4.0171    2.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470    3.2208    3.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1675    3.8746    4.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5562    1.8458    3.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307    1.2122    2.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9430   -0.0834    2.2971 O   0  0  0  0  0  3  0  0  0  0  0  0
   -2.3652   -0.7713    1.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -2.2230    1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183   -3.0681    0.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773   -4.4673    0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -5.0407    1.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881   -6.4257    1.6259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3938   -4.1848    2.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1568   -4.7390    3.4685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2398   -2.8243    2.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0277   -0.4160   -2.9344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763   -0.4606   -4.1089 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0671   -1.3522   -5.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549   -0.9055   -5.4236 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0757   -0.8312   -4.0814 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8295    0.3369   -4.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2886   -1.5873   -2.7810 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2404   -2.5017   -2.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1107    0.8181   -1.1246 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4213   -0.2841   -1.8895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7908    0.6685    0.2466 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1596    0.6655    0.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3513    1.7455    1.1857 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5435    1.2917    2.5127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9838    2.7958    3.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3424    1.2501    1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4592    0.1185   -0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2216   -1.0708   -0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808    0.9655   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    2.0118   -0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5925    5.1558    0.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8760    5.1020    2.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1210    4.1633    4.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0657    1.2501    4.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3156   -2.6916   -0.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075   -5.0959   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -6.8013    2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5948   -4.1239    4.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6950   -2.1683    3.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349    0.5649   -4.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518   -2.3934   -4.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4932   -1.3864   -6.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881   -1.5742   -5.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2995   -1.5060   -4.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8146    0.6582   -5.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2224   -2.1341   -2.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5380   -3.4424   -2.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4981    1.7683   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2210   -0.0290   -2.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4833   -0.3391    0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5012    1.5942    0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9742    2.6595    1.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3686    0.7752    2.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 33  1  0
 33 32  1  0
 32 31  1  0
 31  9  1  0
  9 10  1  0
 10 11  1  0
 11 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 19 17  1  0
 17 18  1  0
 17 16  2  0
 16 14  1  0
 14 15  1  0
 14 13  2  0
 13 12  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 43  1  0
 43 44  1  0
 43 41  1  0
 41 42  1  0
 41 39  1  0
 39 40  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  8 37  1  0
 37 38  1  0
 37 35  1  0
 35 36  1  0
 35 32  1  0
 12 11  2  0
 30 23  1  0
 39  6  1  0
 13 20  1  0
 34 63  1  0
 33 61  1  0
 33 62  1  0
 32 60  1  6
  9 49  1  1
 19 54  1  0
 18 53  1  0
 16 52  1  0
 15 51  1  0
 12 50  1  0
 24 55  1  0
 25 56  1  0
 27 57  1  0
 29 58  1  0
 30 59  1  0
  8 48  1  1
  6 47  1  1
  4 46  1  1
 43 72  1  6
 44 73  1  0
 41 70  1  1
 42 71  1  0
 39 68  1  6
 40 69  1  0
  3 45  1  0
 37 66  1  6
 38 67  1  0
 35 64  1  6
 36 65  1  0
M  CHG  1  21   1
M  END


  Mrv1652309052201372D          

 44 48  0  0  1  0            999 V2000
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  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
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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 O   0  3  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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
   -2.1434   -1.2375    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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
   -2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  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
 21 22  1  0  0  0  0
 11 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 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
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  1  1  0  0  0
  6 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
  4 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  CHG  1  21   1
M  END
> <DATABASE_ID>
NP0204030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C([O+]=C3C=C(O)C=C(O)C3=C2)C2=CC=C(O)C(O)=C2)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O17/c28-7-16-17(33)19(35)24(44-26-21(37)18(34)20(36)23(43-26)25(38)39)27(42-16)41-15-6-10-12(31)4-9(29)5-14(10)40-22(15)8-1-2-11(30)13(32)3-8/h1-6,16-21,23-24,26-28,33-37H,7H2,(H4-,29,30,31,32,38,39)/p+1/t16-,17-,18+,19+,20+,21-,23+,24-,26+,27-/m1/s1

> <INCHI_KEY>
QLKOQFLYESIQLL-ZJNQYPEASA-O

> <FORMULA>
C27H29O17

> <MOLECULAR_WEIGHT>
625.511

> <EXACT_MASS>
625.139925894

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
58.27916425446183

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3R,4S,5S,6R)-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

> <JCHEM_LOGP>
-1.3204

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.388488650756459

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9979815222784665

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7319808463688906

> <JCHEM_POLAR_SURFACE_AREA>
289.65999999999997

> <JCHEM_REFRACTIVITY>
148.53820000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6R)-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+1
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -5.335   1.540   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
HETATM   41  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   43                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   39                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   37                                                  
CONECT    9    8   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   11   23                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   23                                                       
CONECT   31    9   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    8   38                                                  
CONECT   38   37                                                            
CONECT   39    6   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    4   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychromenium-3-yl 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranoside	ChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychromenium-3-yl 2-O-b-D-glucopyranuronosyl-b-D-glucopyranoside	Generator
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychromenium-3-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranoside	Generator
Cyanidin 3-O-(2-O-b-D-glucuronosyl)-b-D-glucoside	Generator
Cyanidin 3-O-(2-O-β-D-glucuronosyl)-β-D-glucoside	Generator

Chemical Formula

C₂₇H₂₉O₁₇

Average Mass

625.5110 Da

Monoisotopic Mass

625.13993 Da

IUPAC Name

3-{[(2S,3R,4S,5S,6R)-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

Traditional Name

3-{[(2S,3R,4S,5S,6R)-3-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C([O+]=C3C=C(O)C=C(O)C3=C2)C2=CC=C(O)C(O)=C2)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H28O17/c28-7-16-17(33)19(35)24(44-26-21(37)18(34)20(36)23(43-26)25(38)39)27(42-16)41-15-6-10-12(31)4-9(29)5-14(10)40-22(15)8-1-2-11(30)13(32)3-8/h1-6,16-21,23-24,26-28,33-37H,7H2,(H4-,29,30,31,32,38,39)/p+1/t16-,17-,18+,19+,20+,21-,23+,24-,26+,27-/m1/s1

InChI Key

QLKOQFLYESIQLL-ZJNQYPEASA-O

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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-3-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
Beta-hydroxy acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Hydroxy acid
Benzenoid
Pyran
Monocyclic benzene moiety
Oxane
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Primary alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:61505 )
anthocyanin cation (CHEBI:61505 )

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	-1.3	ChemAxon
pKa (Strongest Acidic)	3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	289.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	148.54 m³·mol⁻¹	ChemAxon
Polarizability	58.28 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

26332246

KEGG Compound ID

C19762

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50909830

PDB ID

Not Available

ChEBI ID

61505

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium (NP0204030)

MOL for NP0204030 (3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium)

3D MOL for NP0204030 (3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium)

3D SDF for NP0204030 (3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium)

3D-SDF for NP0204030 (3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium)

PDB for NP0204030 (3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium)

3D PDB for NP0204030 (3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium)

SMILES for NP0204030 (3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium)

INCHI for NP0204030 (3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium)

Structure for NP0204030 (3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium)

3D Structure for NP0204030 (3-{[(2s,3r,4s,5s,6r)-3-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium)