NP-MRD: Showing NP-Card for Procyanidin B3 (NP0137003)

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Record Information

Version

2.0

Created at

2022-05-30 16:38:42 UTC

Updated at

2022-05-30 16:38:42 UTC

NP-MRD ID

NP0137003

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Procyanidin B3

Description

Procyanidin B3, also known as C-(4a,8)-C, belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Thus, procyanidin B3 is considered to be a flavonoid lipid molecule. Procyanidin B3 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Procyanidin B3 is found, on average, in the highest concentration within a few different foods, such as quinces, barley, and broad beans and in a lower concentration in sweet cherries, yellow wax beans, and apples. Procyanidin B3 has also been detected, but not quantified in, several different foods, such as guava, carrots, apple ciders, millets, and common wheats. This could make procyanidin B3 a potential biomarker for the consumption of these foods. Procyanidin B3 is found in Acacia baileyana, Actinidia chinensis, Aesculus hippocastanum, Bergenia purpurascens, Betula ovalifolia, Betula pubescens, Calluna vulgaris, Camellia sinensis, Chimarrhis turbinata, Cistus incanus, Coleogyne ramosissima, Cornus kousa, Cryptomeria japonica, Daucus carota, Erythroxylum novogranatense, Eucalyptus ovata, Fragaria ananassa, Geranium thunbergii, Hamamelis virginiana, Humulus lupulus, Juglans sigillata, Juniperus sabina, Larix gmelinii, Lens culinaris, Lespedeza capitata, Liquidambar styraciflua, Lotus pedunculatus, Malus pumila, Oenothera biennis, Paeonia obovata, Paullinia cupana, Phaseolus vulgaris, Pinus sylvestris, Potentilla longifolia, Prunus dulcis, Prunus persica, Pseudotsuga menziesii, Psidium guajava, Pyrola incarnata, Quercus dentata, Quercus ilex, Quercus marilandica, Quercus miyagii, Quercus phillyraeoides, Quercus robur, Rhodiola semenovii, Rosa cymosa, Rosa henryi, Rosa rugosa, Rumex acetosa, Salix caprea, Sanguisorba officinalis, Taxus mairei, Toona sinensis, Vaccinium vitis-idaea, Vicia faba, Vigna angularis and Vitis vinifera. Procyanidin B3 was first documented in 2010 (PMID: 20131846). A proanthocyanidin consisting of two molecules of (+)-catechin joined by a bond between positions 4 and 8' in alpha-configuration (PMID: 20568787) (PMID: 20955177) (PMID: 21950419) (PMID: 22629448).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Procyanidin dimer B3
  Mrv1572001071617282D          

 43 48  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  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    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    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
    3.5724    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  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -1.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221   -2.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221   -3.0496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6924   -1.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6924   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068   -0.5746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1213   -0.9871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1213   -1.8121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8358   -2.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068   -2.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358    0.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503    0.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503    1.4879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647    0.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792    0.6629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4511   -0.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  2 14  1  0  0  0  0
  7 14  1  0  0  0  0
  5 15  1  6  0  0  0
 15 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
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
  2 23  1  6  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  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 28 34  1  0  0  0  0
 31 35  1  6  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 35 42  1  0  0  0  0
 24 43  1  0  0  0  0
M  END

     RDKit          3D

 68 73  0  0  0  0  0  0  0  0999 V2000
   -2.5018   -5.4293    2.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1222   -4.2457    1.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489   -4.1809    1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5407   -3.0054    0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392   -3.0336   -0.3226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3420   -1.8797    0.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072   -1.9346    1.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9051   -3.0919    1.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -0.7642    1.2292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    0.4851    0.8903 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8882    1.4264    0.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0429    1.0992    0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0897    2.0008   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0275    3.2584    0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0859    4.1634    0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8759    3.5905    1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8226    4.8577    1.7637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8239    2.6845    1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9111    0.4185   -0.3642 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1833    1.6445   -0.3781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852   -0.6505   -0.2186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1964   -0.8929   -1.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8026   -1.4913   -2.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087   -1.9336   -2.4980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0831   -1.6594   -3.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131   -1.2513   -3.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091   -1.4270   -5.1100 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8278   -0.6485   -2.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -0.4839   -1.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824    0.1266   -0.6155 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1971    0.0616   -0.5758 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7644    0.7531    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3503    1.9974    0.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9025    2.6357    2.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8997    2.0033    2.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4589    2.6267    3.9056 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440    0.7540    2.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3537    0.1578    3.1837 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7766    0.1574    1.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8081    0.5355   -1.8724 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1817    0.2309   -1.7956 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2343   -0.2132   -3.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0684   -6.1327    1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3507   -5.0839    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799   -3.8812   -0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345   -3.1044    2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0800    0.8659    1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0787    0.1051   -0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9771    1.7283   -0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9987    5.0764    0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0525    5.2192    2.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388    2.9893    1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728    0.4247   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7444    1.7789    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784   -0.2435    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6659   -1.8617   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640   -2.1314   -4.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8615   -1.1058   -5.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4498   -1.0325   -0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5613    2.5161    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5803    3.6135    2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1927    2.1757    4.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7112   -0.7589    2.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1135   -0.8197    1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7391    1.6289   -1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2798   -0.7464   -1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8390   -1.1219   -3.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283    0.4501   -3.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  1  0
 19 20  1  0
 19 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  8  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
 10 11  1  0
 11 18  2  0
 18 16  1  0
 16 17  1  0
 16 14  2  0
 14 15  1  0
 14 13  1  0
 13 12  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 40  1  0
 40 41  1  0
 40 42  1  0
 31 32  1  0
 32 39  2  0
 39 37  1  0
 37 38  1  0
 37 35  2  0
 35 36  1  0
 35 34  1  0
 34 33  2  0
  6 21  1  0
 12 11  1  0
 29 22  1  0
 33 32  1  0
  6  7  1  0
 42 28  1  0
 21 55  1  1
 19 53  1  6
 20 54  1  0
 10 47  1  1
  8 46  1  0
  1 43  1  0
  3 44  1  0
  5 45  1  0
 18 52  1  0
 17 51  1  0
 15 50  1  0
 13 49  1  0
 12 48  1  0
 24 56  1  0
 25 57  1  0
 27 58  1  0
 31 59  1  1
 40 65  1  6
 41 66  1  0
 42 67  1  0
 42 68  1  0
 39 64  1  0
 38 63  1  0
 36 62  1  0
 34 61  1  0
 33 60  1  0
M  END

Procyanidin dimer B3
  Mrv1572001071617282D          

 43 48  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  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    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    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
    3.5724    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  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -1.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221   -2.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221   -3.0496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6924   -1.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6924   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068   -0.5746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1213   -0.9871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1213   -1.8121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8358   -2.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068   -2.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358    0.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503    0.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503    1.4879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647    0.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792    0.6629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4511   -0.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  2 14  1  0  0  0  0
  7 14  1  0  0  0  0
  5 15  1  6  0  0  0
 15 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
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
  2 23  1  6  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  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 28 34  1  0  0  0  0
 31 35  1  6  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 35 42  1  0  0  0  0
 24 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137003

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1([C@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C(O)C=C(O)C2=C1O[C@@H]([C@@H](O)C2)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1

> <INCHI_KEY>
XFZJEEAOWLFHDH-AVFWISQGSA-N

> <FORMULA>
C30H26O12

> <MOLECULAR_WEIGHT>
578.526

> <EXACT_MASS>
578.142426277

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
57.266604009835376

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
3.1157450136666665

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.12686840566425

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.693248815093794

> <JCHEM_PKA_STRONGEST_BASIC>
-5.176560370760915

> <JCHEM_POLAR_SURFACE_AREA>
220.75999999999996

> <JCHEM_REFRACTIVITY>
146.50799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
procyanidin B3

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Procyanidin dimer B3                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.041  -1.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.375  -1.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.375  -3.383   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.041  -4.153   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.041  -5.693   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.292  -3.383   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.292  -1.843   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.626  -1.073   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.960  -1.843   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.960  -3.383   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.293  -4.153   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.626  -4.153   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.293  -1.073   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.293   0.467   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.627   1.237   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.627   2.777   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.961   0.467   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       9.295   1.237   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       7.961  -1.073   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.627  -1.843   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.709  -1.072   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14   23                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    2    7                                                  
CONECT   15    5   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   15                                                       
CONECT   23    2   24   29                                                  
CONECT   24   23   25   43                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   34                                                  
CONECT   29   28   23   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   28                                                       
CONECT   35   31   36   42                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   35                                                       
CONECT   43   24                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
C-(4a,8)-C	ChEBI
Catechin(4a->8)catechin	ChEBI
Catechin-(4alpha->8)-catechin	ChEBI
Proanthocyanidin b3	ChEBI
Catechin-(4a->8)-catechin	Generator
Catechin-(4α->8)-catechin	Generator
2,3-trans-Proanthocyanidin	HMDB
Afzelechin-(4alpha->8)-afzelechin	HMDB
Procyanidin b-3	HMDB

Chemical Formula

C₃₀H₂₆O₁₂

Average Mass

578.5260 Da

Monoisotopic Mass

578.14243 Da

IUPAC Name

(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

procyanidin B3

CAS Registry Number

Not Available

SMILES

[H][C@@]1([C@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C(O)C=C(O)C2=C1O[C@@H]([C@@H](O)C2)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1

InChI Key

XFZJEEAOWLFHDH-AVFWISQGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acacia baileyana	LOTUS Database	35616633
Actinidia chinensis	LOTUS Database	35616633
Aesculus hippocastanum	LOTUS Database	35616633
Bergenia purpurascens	LOTUS Database	35616633
Betula ovalifolia	LOTUS Database	35616633
Betula pubescens	LOTUS Database	35616633
Calluna vulgaris	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Chimarrhis turbinata	LOTUS Database	35616633
Cistus incanus	LOTUS Database	35616633
Coleogyne ramosissima	LOTUS Database	35616633
Cornus kousa	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Erythroxylum novogranatense	LOTUS Database	35616633
Eucalyptus ovata	LOTUS Database	35616633
Fragaria x ananassa	LOTUS Database	35616633
Geranium thunbergii	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Juglans sigillata	LOTUS Database	35616633
Juniperus sabina	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Lens culinaris	LOTUS Database	35616633
Lespedeza capitata	LOTUS Database	35616633
Liquidambar styraciflua	LOTUS Database	35616633
Lotus pedunculatus	LOTUS Database	35616633
Malus pumila	LOTUS Database	35616633
Oenothera biennis	LOTUS Database	35616633
Paeonia obovata	LOTUS Database	35616633
Paullinia cupana	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Pinus sylvestris	LOTUS Database	35616633
Potentilla viscosa	LOTUS Database	35616633
Prunus dulcis	LOTUS Database	35616633
Prunus persica	LOTUS Database	35616633
Pseudotsuga menziesii	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633
Pyrola incarnata	LOTUS Database	35616633
Quercus dentata	LOTUS Database	35616633
Quercus ilex	LOTUS Database	35616633
Quercus marilandica	LOTUS Database	35616633
Quercus miyagii	LOTUS Database	35616633
Quercus phillyraeoides	LOTUS Database	35616633
Quercus robur	LOTUS Database	35616633
Rhodiola semenovii	LOTUS Database	35616633
Rosa cymosa	LOTUS Database	35616633
Rosa henryi	LOTUS Database	35616633
Rosa rugosa	LOTUS Database	35616633
Rumex acetosa	LOTUS Database	35616633
Salix caprea	LOTUS Database	35616633
Sanguisorba officinalis	LOTUS Database	35616633
Taxus mairei	LOTUS Database	35616633
Toona sinensis	LOTUS Database	35616633
Vaccinium vitis-idaea	LOTUS Database	35616633
Vicia faba	LOTUS Database	35616633
Vigna angularis	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

B-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Flavan-3-ol
Hydroxyflavonoid
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan
Chromane
1-benzopyran
Benzopyran
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:75630 )
proanthocyanidin (CHEBI:75630 )
biflavonoid (CHEBI:75630 )
hydroxyflavan (CHEBI:75630 )
Proanthocyanidins (LMPK12030003 )

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	2.29	ALOGPS
logP	3.12	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	220.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	146.51 m³·mol⁻¹	ChemAxon
Polarizability	57.27 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033974

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Procyanidin_B3

METLIN ID

Not Available

PubChem Compound

146798

PDB ID

Not Available

ChEBI ID

75630

Good Scents ID

Not Available

References

General References

Cruz L, Bras NF, Teixeira N, Mateus N, Ramos MJ, Dangles O, De Freitas V: Vinylcatechin dimers are much better copigments for anthocyanins than catechin dimer procyanidin b3. J Agric Food Chem. 2010 Mar 10;58(5):3159-66. doi: 10.1021/jf9037419. [PubMed:20131846 ]
Oizumi Y, Mohri Y, Hirota M, Makabe H: Synthesis of procyanidin B3 and its anti-inflammatory activity. the effect of 4-alkoxy group of catechin electrophile in the Yb(OTf)(3)-catalyzed condensation with catechin nucleophile. J Org Chem. 2010 Jul 16;75(14):4884-6. doi: 10.1021/jo1009382. [PubMed:20568787 ]
Choi KC, Park S, Lim BJ, Seong AR, Lee YH, Shiota M, Yokomizo A, Naito S, Na Y, Yoon HG: Procyanidin B3, an inhibitor of histone acetyltransferase, enhances the action of antagonist for prostate cancer cells via inhibition of p300-dependent acetylation of androgen receptor. Biochem J. 2011 Jan 1;433(1):235-44. doi: 10.1042/BJ20100980. [PubMed:20955177 ]
Goncalves R, Mateus N, De Freitas V: Influence of carbohydrates on the interaction of procyanidin B3 with trypsin. J Agric Food Chem. 2011 Nov 9;59(21):11794-802. doi: 10.1021/jf203060s. Epub 2011 Oct 10. [PubMed:21950419 ]
Aini H, Ochi H, Iwata M, Okawa A, Koga D, Okazaki M, Sano A, Asou Y: Procyanidin B3 prevents articular cartilage degeneration and heterotopic cartilage formation in a mouse surgical osteoarthritis model. PLoS One. 2012;7(5):e37728. doi: 10.1371/journal.pone.0037728. Epub 2012 May 22. [PubMed:22629448 ]

Showing NP-Card for Procyanidin B3 (NP0137003)

MOL for NP0137003 (Procyanidin B3)

3D MOL for NP0137003 (Procyanidin B3)

3D SDF for NP0137003 (Procyanidin B3)

3D-SDF for NP0137003 (Procyanidin B3)

PDB for NP0137003 (Procyanidin B3)

3D PDB for NP0137003 (Procyanidin B3)

SMILES for NP0137003 (Procyanidin B3)

INCHI for NP0137003 (Procyanidin B3)

Structure for NP0137003 (Procyanidin B3)

3D Structure for NP0137003 (Procyanidin B3)