NP-MRD: Showing NP-Card for Procyanidin B1 (NP0136957)

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Record Information

Version

2.0

Created at

2022-05-30 16:37:17 UTC

Updated at

2022-05-30 16:37:17 UTC

NP-MRD ID

NP0136957

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Procyanidin B1

Description

Procyanidin B1, also known as ec-(4b,8)-C or endotelon, 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 B1 is considered to be a flavonoid lipid molecule. Procyanidin B1 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Procyanidin B1 is found, on average, in the highest concentration within a few different foods, such as cocoa powders, peach (var.), And nectarines and in a lower concentration in quinces, green beans, and custard apples. Procyanidin B1 has also been detected, but not quantified in, several different foods, such as ceylon cinnamons, common wheats, lentils, green bell peppers, and chickpea. This could make procyanidin B1 a potential biomarker for the consumption of these foods. . Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat's claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach. Procyanidin B1 is found in Alhagi sparsifolia, Areca catechu, Bischofia javanica, Camellia sinensis, Cinnamomum aromaticum, Cinnamomum burmannii, Cistus incanus, Cola nitida, Coleogyne ramosissima, Croton lechleri, Cynomorium songaricum, Dioscorea bulbifera, Dioscorea cirrhosa, Erythroxylum novogranatense, Eucalyptus ovata, Illicium anisatum, Kandelia candel, Lens culinaris, Lotus pedunculatus, Malus domestica, Malus pumila, Paullinia cupana, Phaseolus vulgaris, Pinus sylvestris, Platycodon grandiflorus, Prunus persica, Pseudotsuga menziesii, Psidium guajava, Pyrola incarnata, Quercus miyagii, Quercus phillyraeoides, Rhododendron dauricum, Ribes rubrum, Rumex acetosa, Saraca asoca, Terminalia catappa, Vaccinium vitis-idaea, Vicia faba, Vitis vinifera and Zanthoxylum piperitum. Procyanidin B1 was first documented in 2011 (PMID: 21405989). A proanthocyanidin consisting of (-)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8' respectively in a beta-configuration (PMID: 22227333) (PMID: 22473647) (PMID: 23993614) (PMID: 24250715).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Procyanidin dimer B1
  Mrv1572001071617282D          

 42 47  0  0  1  0            999 V2000
    1.1608   -2.4631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8752   -2.8756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4463   -2.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -2.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826   -2.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826   -3.7006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6971   -2.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6971   -1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116   -1.2256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826   -1.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4463   -1.2256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608   -1.6381    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8752   -1.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752   -0.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -0.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187    0.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -1.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187   -1.6381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897   -1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826    0.0635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6971    0.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116    0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261    0.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261    1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8405    1.7135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116    1.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6971    1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826    1.7135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682    1.3010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4463    1.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4463    2.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608    2.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    2.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    2.9510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    1.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    1.3010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608    1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682    0.4760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4463    0.0635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116   -0.7615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 14 21  1  0  0  0  0
 22 10  1  1  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  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
 40 31  1  0  0  0  0
 40 22  1  0  0  0  0
 40 41  1  6  0  0  0
 24 42  1  0  0  0  0
M  END

     RDKit          3D

 68 73  0  0  0  0  0  0  0  0999 V2000
    0.6914    4.3672   -3.8773 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653    3.2627   -3.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    2.2200   -2.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9086    1.1060   -2.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8346    0.0543   -2.0360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3258    1.0685   -1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223    2.0958   -1.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8711    3.2035   -2.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4982    2.0374   -1.1470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1411    0.7560   -1.1311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0525    0.5878    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7723    0.9530    1.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6707    0.7702    2.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8996    0.2015    2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8223    0.0048    3.0923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2304   -0.1817    0.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4751   -0.7517    0.5656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3088    0.0182   -0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749   -0.3838   -1.3363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6865   -1.5643   -0.8262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140   -0.0461   -0.7718 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0612   -1.1635   -0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2611   -2.0854   -1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -2.0320   -2.8055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1173   -3.1649   -1.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864   -3.3553   -0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6308   -4.4417    0.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5743   -2.4111    0.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281   -1.3438    0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -0.4640    1.7135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848   -0.2909    2.6305 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8297    0.3773    1.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5313    1.4671    1.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5103    2.1789    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8312    1.8363    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7932    2.5824    0.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1490    0.7682    1.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4822    0.4240    1.6342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444    0.0606    2.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0162   -1.6257    3.1943 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9643   -2.0903    3.9850 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2978   -2.6207    2.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0786    5.1395   -4.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389    2.2207   -3.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133    0.1463   -2.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6035    4.0183   -2.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7975    0.7982   -2.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042    1.4016    1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4341    1.0636    3.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6656    0.2538    4.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6822   -1.0213   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6230   -0.3049   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0411   -0.5288   -2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6474   -1.6390   -0.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0359    0.4164    0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1832   -2.6979   -3.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2790   -3.8994   -2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0899   -4.5225    0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    0.4068    3.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011    1.7693    1.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2687    3.0169   -0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7685    2.3905    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -0.3526    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3929   -0.7820    2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9001   -1.6010    3.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1477   -1.6939    3.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0261   -3.6348    2.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -2.7490    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
 41 40  1  0
 40 42  1  0
 42 28  1  0
 28 26  2  0
 26 27  1  0
 26 25  1  0
 25 23  2  0
 23 24  1  0
 23 22  1  0
 22 21  1  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 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 22 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  2  0
 31 40  1  0
 39 32  1  0
 29 28  1  0
  6 21  1  0
 18 11  1  0
  6  7  1  0
 41 66  1  0
 40 65  1  1
 42 67  1  0
 42 68  1  0
 27 58  1  0
 25 57  1  0
 24 56  1  0
 21 55  1  1
 19 53  1  6
 20 54  1  0
 10 47  1  6
  8 46  1  0
  1 43  1  0
  3 44  1  0
  5 45  1  0
 12 48  1  0
 13 49  1  0
 15 50  1  0
 17 51  1  0
 18 52  1  0
 31 59  1  1
 33 60  1  0
 34 61  1  0
 36 62  1  0
 38 63  1  0
 39 64  1  0
M  END

Procyanidin dimer B1
  Mrv1572001071617282D          

 42 47  0  0  1  0            999 V2000
    1.1608   -2.4631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8752   -2.8756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4463   -2.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -2.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826   -2.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826   -3.7006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6971   -2.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6971   -1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116   -1.2256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826   -1.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682   -1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4463   -1.2256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608   -1.6381    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8752   -1.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752   -0.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -0.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187    0.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -1.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187   -1.6381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897   -1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826    0.0635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6971    0.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116    0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261    0.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261    1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8405    1.7135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116    1.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6971    1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9826    1.7135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682    1.3010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4463    1.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4463    2.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608    2.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    2.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    2.9510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    1.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    1.3010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608    1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2682    0.4760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4463    0.0635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116   -0.7615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 14 21  1  0  0  0  0
 22 10  1  1  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  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
 40 31  1  0  0  0  0
 40 22  1  0  0  0  0
 40 41  1  6  0  0  0
 24 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136957

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](O)[C@H](OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2O[C@@H]1C1=CC=C(O)C(O)=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-UKWJTHFESA-N

> <FORMULA>
C30H26O12

> <MOLECULAR_WEIGHT>
578.526

> <EXACT_MASS>
578.142426277

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
57.121978140681996

> <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,3R,4R)-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 B1

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Procyanidin dimer B1                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       2.167  -4.598   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.500  -5.368   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.833  -5.368   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.501  -4.598   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.834  -5.368   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.834  -6.908   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.168  -4.598   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.168  -3.058   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.502  -2.288   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.834  -2.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.501  -3.058   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.833  -2.288   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.167  -3.058   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.500  -2.288   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.500  -0.748   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.834   0.022   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.168  -0.748   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.502   0.022   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.168  -2.288   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.502  -3.058   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.834  -3.058   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.834   0.119   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.168   0.889   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.502   0.119   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.835   0.889   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.835   2.429   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.169   3.199   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.502   3.199   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.168   2.429   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.834   3.199   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.501   2.429   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.833   3.199   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.833   4.739   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.167   5.509   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.500   4.739   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.834   5.509   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.500   3.199   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.834   2.429   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.167   2.429   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.501   0.889   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.833   0.119   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -4.502  -1.421   0.000  0.00  0.00           O+0
CONECT    1    2    3   13                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    1   14                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14                                                       
CONECT   22   10   23   40                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25   42                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32                                                       
CONECT   40   31   22   41                                                  
CONECT   41   40                                                            
CONECT   42   24                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
EC-(4b,8)-C	ChEBI
Endotelon	ChEBI
Epicatechin(4beta->8)catechin	ChEBI
Epicatechin-(4beta->8)-ent-epicatechin	ChEBI
Proanthocyanidin b1	ChEBI
Procyanidin dimer b1	ChEBI
Epicatechin(4b->8)catechin	Generator
Epicatechin(4β->8)catechin	Generator
Epicatechin-(4b->8)-ent-epicatechin	Generator
Epicatechin-(4β->8)-ent-epicatechin	Generator
Procyanidin b	HMDB
Procyanidin D	HMDB
Procyanidol D	HMDB
Procyanidol oligomer	HMDB

Chemical Formula

C₃₀H₂₆O₁₂

Average Mass

578.5260 Da

Monoisotopic Mass

578.14243 Da

IUPAC Name

(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-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 B1

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](O)[C@H](OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2O[C@@H]1C1=CC=C(O)C(O)=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-UKWJTHFESA-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
Alhagi sparsifolia	LOTUS Database	35616633
Areca catechu	LOTUS Database	35616633
Bischofia javanica	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Cinnamomum aromaticum	LOTUS Database	35616633
Cinnamomum burmanni	LOTUS Database	35616633
Cistus incanus	LOTUS Database	35616633
Cola nitida	LOTUS Database	35616633
Coleogyne ramosissima	LOTUS Database	35616633
Croton lechleri	LOTUS Database	35616633
Cynomorium songaricum	LOTUS Database	35616633
Dioscorea bulbifera	LOTUS Database	35616633
Dioscorea cirrhosa	LOTUS Database	35616633
Erythroxylum novogranatense	LOTUS Database	35616633
Eucalyptus ovata	LOTUS Database	35616633
Illicium anisatum	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Lens culinaris	LOTUS Database	35616633
Lotus pedunculatus	LOTUS Database	35616633
Malus domestica	LOTUS Database	35616633
Malus pumila	LOTUS Database	35616633
Paullinia cupana	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Pinus sylvestris	LOTUS Database	35616633
Platycodon grandiflorus	LOTUS Database	35616633
Prunus persica	LOTUS Database	35616633
Pseudotsuga menziesii	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633
Pyrola incarnata	LOTUS Database	35616633
Quercus miyagii	LOTUS Database	35616633
Quercus phillyraeoides	LOTUS Database	35616633
Rhododendron dauricum	LOTUS Database	35616633
Ribes rubrum	LOTUS Database	35616633
Rumex acetosa	LOTUS Database	35616633
Saraca asoca	LOTUS Database	35616633
Terminalia catappa	LOTUS Database	35616633
Vaccinium vitis-idaea	LOTUS Database	35616633
Vicia faba	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Zanthoxylum piperitum	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:75633 )
proanthocyanidin (CHEBI:75633 )
biflavonoid (CHEBI:75633 )
hydroxyflavan (CHEBI:75633 )
Proanthocyanidins (LMPK12030001 )

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	57.12 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

HMDB0029754

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_B1

METLIN ID

Not Available

PubChem Compound

11250133

PDB ID

Not Available

ChEBI ID

75633

Good Scents ID

Not Available

References

General References

Terra X, Palozza P, Fernandez-Larrea J, Ardevol A, Blade C, Pujadas G, Salvado J, Arola L, Blay MT: Procyanidin dimer B1 and trimer C1 impair inflammatory response signalling in human monocytes. Free Radic Res. 2011 May;45(5):611-9. doi: 10.3109/10715762.2011.564165. [PubMed:21405989 ]
Shimada T, Tokuhara D, Tsubata M, Kamiya T, Kamiya-Sameshima M, Nagamine R, Takagaki K, Sai Y, Miyamoto K, Aburada M: Flavangenol (pine bark extract) and its major component procyanidin B1 enhance fatty acid oxidation in fat-loaded models. Eur J Pharmacol. 2012 Feb 29;677(1-3):147-53. doi: 10.1016/j.ejphar.2011.12.034. Epub 2011 Dec 29. [PubMed:22227333 ]
Bijak M, Saluk J, Ponczek MB, Nowak P: Antithrombin effect of polyphenol-rich extracts from black chokeberry and grape seeds. Phytother Res. 2013 Jan;27(1):71-6. doi: 10.1002/ptr.4682. Epub 2012 Apr 4. [PubMed:22473647 ]
Du H, Wu J, Li H, Zhong PX, Xu YJ, Li CH, Ji KX, Wang LS: Polyphenols and triterpenes from Chaenomeles fruits: chemical analysis and antioxidant activities assessment. Food Chem. 2013 Dec 15;141(4):4260-8. doi: 10.1016/j.foodchem.2013.06.109. Epub 2013 Jul 4. [PubMed:23993614 ]
Liu YC, Chen CJ, Lee MR, Li M, Hsieh WT, Chung JG, Ho HC: Peroxidase as the major protein constituent in areca nut and identification of its natural substrates. Evid Based Complement Alternat Med. 2013;2013:412851. doi: 10.1155/2013/412851. Epub 2013 Oct 24. [PubMed:24250715 ]

Showing NP-Card for Procyanidin B1 (NP0136957)

MOL for NP0136957 (Procyanidin B1)

3D MOL for NP0136957 (Procyanidin B1)

3D SDF for NP0136957 (Procyanidin B1)

3D-SDF for NP0136957 (Procyanidin B1)

PDB for NP0136957 (Procyanidin B1)

3D PDB for NP0136957 (Procyanidin B1)

SMILES for NP0136957 (Procyanidin B1)

INCHI for NP0136957 (Procyanidin B1)

Structure for NP0136957 (Procyanidin B1)

3D Structure for NP0136957 (Procyanidin B1)