NP-MRD: Showing NP-Card for pelargonidin 3-o-sophoroside (NP0178788)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 16:50:44 UTC

Updated at

2022-09-03 16:50:44 UTC

NP-MRD ID

NP0178788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pelargonidin 3-o-sophoroside

Description

Pelargonidin 3-O-sophoroside 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. pelargonidin 3-o-sophoroside is found in Rubus idaeus and Tropaeolum majus. pelargonidin 3-o-sophoroside was first documented in 2006 (PMID: 16968067). Pelargonidin 3-O-sophoroside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Pelargonidin 3-O-sophoroside
  Mrv1652309231721082D          

 42 46  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
   -2.8579    2.4749    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    1.2374    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    1.2374    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   -1.2374    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   -1.2374    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   -1.2374    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   -2.4749    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   -2.4749    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
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    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    2.4749    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    2.4749    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    2.4749    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    1.2374    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    2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  1  0  0  0
  5 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  6  0  0  0
M  CHG  1  20   1
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
    1.4087   -3.2535   -4.2623 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092   -1.8780   -4.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556   -1.4323   -2.9406 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6088   -1.8459   -1.7728 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3896   -1.3403   -0.7341 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7352   -1.2325    0.4978 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    0.0782    0.9187 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3286    0.4857    1.3958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7543    0.2269    0.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0539    0.5645    0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3791    1.3680    1.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6739    1.7608    2.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0050    2.5464    3.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817    3.0132    4.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3469    2.9335    3.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2813    2.4954    2.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6351    2.8618    2.7706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9456    1.6979    1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6436    1.3033    1.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2897    0.5633    0.2489 O   0  0  0  0  0  3  0  0  0  0  0  0
   -3.0644    0.1668   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8421   -0.6907   -1.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7409   -1.4414   -1.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6579   -2.1935   -2.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -2.2360   -3.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5650   -2.9706   -4.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7579   -1.4564   -3.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591   -0.7179   -2.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3703    1.9360    1.5795 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251    2.1595    2.7323 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8648    3.4622    2.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868    4.5316    2.3965 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534    1.0877    3.1408 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5822    0.2047    4.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    0.4055    1.9711 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6245    1.3187    1.4731 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466   -2.2788   -0.5940 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3974   -1.8940    0.4230 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907   -2.5026   -1.8701 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4233   -3.8826   -2.0575 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -1.8957   -3.0693 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4379   -0.8129   -3.4891 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6920   -3.6063   -5.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -1.5835   -5.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587   -1.3644   -4.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2080   -0.3201   -2.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -0.3311   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184    0.6836    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0622    0.1936    2.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424    1.7051    2.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1001    2.8344    4.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5602    3.5540    4.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8751    3.4398    3.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7509    1.3905    0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228   -1.4813   -0.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7805   -2.7926   -2.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -3.5539   -5.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5637   -1.4570   -4.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7565   -0.1235   -2.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4140    2.3432    3.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    3.7059    3.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734    3.4382    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4076    5.3236    2.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9510    1.5914    3.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3237   -0.2264    4.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272   -0.4797    2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4419    1.3973    0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011   -3.2582   -0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625   -2.6861    0.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3438   -2.1359   -1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3293   -4.0964   -3.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144   -2.6246   -3.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2604   -0.6957   -2.9593 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
  8 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
  5 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 41  3  1  0
 35  7  1  0
 21 10  1  0
 28 22  1  0
 19 12  1  0
  1 43  1  0
  2 44  1  0
  2 45  1  0
  3 46  1  1
  5 47  1  6
  7 48  1  6
  8 49  1  1
 11 50  1  0
 14 51  1  0
 15 52  1  0
 17 53  1  0
 18 54  1  0
 23 55  1  0
 24 56  1  0
 26 57  1  0
 27 58  1  0
 28 59  1  0
 30 60  1  1
 31 61  1  0
 31 62  1  0
 32 63  1  0
 33 64  1  1
 34 65  1  0
 35 66  1  1
 36 67  1  0
 37 68  1  1
 38 69  1  0
 39 70  1  1
 40 71  1  0
 41 72  1  6
 42 73  1  0
M  CHG  1  20   1
M  END

Pelargonidin 3-O-sophoroside
  Mrv1652309231721082D          

 42 46  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
   -2.8579    2.4749    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    1.2374    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    1.2374    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   -1.2374    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   -1.2374    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   -1.2374    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   -2.4749    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   -2.4749    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
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    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    2.4749    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    2.4749    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    2.4749    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    1.2374    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    2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  1  0  0  0
  5 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  6  0  0  0
M  CHG  1  20   1
M  END
> <DATABASE_ID>
NP0178788

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(O)C=C(O)C=C4[O+]=C3C3=CC=C(O)C=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O15/c28-8-17-19(33)21(35)23(37)26(40-17)42-25-22(36)20(34)18(9-29)41-27(25)39-16-7-13-14(32)5-12(31)6-15(13)38-24(16)10-1-3-11(30)4-2-10/h1-7,17-23,25-29,33-37H,8-9H2,(H2-,30,31,32)/p+1/t17-,18-,19-,20-,21+,22+,23-,25-,26+,27-/m1/s1

> <INCHI_KEY>
HASVPNDDKSXPGU-WGNLCONDSA-O

> <FORMULA>
C27H31O15

> <MOLECULAR_WEIGHT>
595.526

> <EXACT_MASS>
595.166295322

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.68058355932849

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
-1.4453000000000005

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.535847866101228

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.396815323828055

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648377595763173

> <JCHEM_POLAR_SURFACE_AREA>
252.35999999999996

> <JCHEM_REFRACTIVITY>
146.68990000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Pelargonidin 3-O-sophoroside                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-SEP-17         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  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+1
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334   3.850   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      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   10   22                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29    8   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    7   36                                                  
CONECT   36   35                                                            
CONECT   37    5   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39    3   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
Pelargonidin 3-sophoroside	ChEBI

Chemical Formula

C₂₇H₃₁O₁₅

Average Mass

595.5260 Da

Monoisotopic Mass

595.16630 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(O)C=C(O)C=C4[O+]=C3C3=CC=C(O)C=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H30O15/c28-8-17-19(33)21(35)23(37)26(40-17)42-25-22(36)20(34)18(9-29)41-27(25)39-16-7-13-14(32)5-12(31)6-15(13)38-24(16)10-1-3-11(30)4-2-10/h1-7,17-23,25-29,33-37H,8-9H2,(H2-,30,31,32)/p+1/t17-,18-,19-,20-,21+,22+,23-,25-,26+,27-/m1/s1

InChI Key

HASVPNDDKSXPGU-WGNLCONDSA-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
Rubus idaeus	LOTUS Database	35616633
Tropaeolum majus	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
7-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
4'-hydroxyflavonoid
Anthocyanidin
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Primary alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin glycoside (CHEBI:80437 )
Anthocyanidins (C16305 )
Anthocyanidins and anthocyanins (C16305 )

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	0.1	ALOGPS
logP	-1.4	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	252.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.69 m³·mol⁻¹	ChemAxon
Polarizability	56.68 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

C00006636

Chemspider ID

Not Available

KEGG Compound ID

C16305

BioCyc ID

CPD-7843

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724704

PDB ID

Not Available

ChEBI ID

134007

Good Scents ID

Not Available

References

General References

Chirinos R, Campos D, Betalleluz I, Giusti MM, Schwartz SJ, Tian Q, Pedreschi R, Larondelle Y: High-performance liquid chromatography with photodiode array detection (HPLC-DAD)/HPLC-mass spectrometry (MS) profiling of anthocyanins from Andean Mashua Tubers (Tropaeolum tuberosum Ruiz and Pavon) and their contribution to the overall antioxidant activity. J Agric Food Chem. 2006 Sep 20;54(19):7089-97. doi: 10.1021/jf0614140. [PubMed:16968067 ]
LOTUS database [Link]

Showing NP-Card for pelargonidin 3-o-sophoroside (NP0178788)

MOL for NP0178788 (pelargonidin 3-o-sophoroside)

3D MOL for NP0178788 (pelargonidin 3-o-sophoroside)

3D SDF for NP0178788 (pelargonidin 3-o-sophoroside)

3D-SDF for NP0178788 (pelargonidin 3-o-sophoroside)

PDB for NP0178788 (pelargonidin 3-o-sophoroside)

3D PDB for NP0178788 (pelargonidin 3-o-sophoroside)

SMILES for NP0178788 (pelargonidin 3-o-sophoroside)

INCHI for NP0178788 (pelargonidin 3-o-sophoroside)

Structure for NP0178788 (pelargonidin 3-o-sophoroside)

3D Structure for NP0178788 (pelargonidin 3-o-sophoroside)