NP-MRD: Showing NP-Card for Procyanidin B2 (NP0030547)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2021-06-19 21:52:42 UTC

Updated at

2021-08-20 00:00:18 UTC

NP-MRD ID

NP0030547

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Procyanidin B2

Provided By

JEOL Database JEOL Logo

Description

Procyanidin B2, also known as procyanidol B2 or ec-(4b,8)-ec, 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 B2 is considered to be a flavonoid. Procyanidin B2 is found, on average, in the highest concentration within a few different foods, such as cocoa powder, chocolate, and broad beans (Vicia faba) and in a lower concentration in teas (Camellia sinensis), common beans (Phaseolus vulgaris), and sherry. Procyanidin B2 has also been detected, but not quantified in, several different foods, such as bulgur, cocoa beans (Theobroma cacao), common peas (Pisum sativum), oriental wheats (Triticum turanicum), and barleys (Hordeum vulgare). This could make procyanidin B2 a potential biomarker for the consumption of these foods. Procyanidin B2 is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Procyanidin B2 is found in Albizia lebbeck, Alhagi sparsifolia, Apis cerana, Apocynum venetum, Areca catechu , Banisteriopsis caapi, Begonia fagifolia, Bergenia purpurascens, Betula pubescens , Byrsonima crassifolia , Calluna vulgaris , Camellia japonica , Camellia reticulata, Camellia sinensis var.assamica , Campylotropis hirella, Cassia fistula , Cecropia glaziovii, Chamaerops humilis , Cinchona pubescens, Cinnamomum bejolghota, Cinnamomum burmannii, Cinnamomum camphora , Cinnamomum cirrhosa, Cistus incanus, Cola nitida, Coleogyne ramosissima, Crataegus laevigata, Crataegus monogyma, Crataegus monogyna , Crataegus sinaica, Croton lechleri, Cryptocarya obovata, Davallia divaricata, Dioscorea alata , Dioscorea bulbifera , Dioscorea cirrhosa, Fagopyrum cymosum , Fallopia multiflora, Fragaria spp., Fragaria vesca , Garcinia mangostana, Geranium sanguineum, Humulus lupulus, Hypericum erectum, Juniperus sabina, Kandelia candel, Larix gmelini, Lindera umbellata, Lotus corniculatus, Lotus uliginosus, Malus domestica, Malus sylvestris, Gymnosporia senegalensis, Melastoma candidum, Metroxylon sagu , Metroxylon sagus, Nelia pillansii, Paullinia cupana, Picea abies , Pinus sylvestris, Platanus orientalis, Populus canescens, Potentilla erecta , Potentilla viscosa, Prunus dulcis, Pseudotsuga menziesii, Psorospermum febrifugum, Pyrola incarnata, Pyrus spp., Quercus marilandica, Quercus miyagii, Rheum sp., Rhizophora stylosa, Riedeliella graciliflora, Rosa cymosa, Rosa henryi, Rosa laevigata , Rubus spp. , Rumex acetosa, Salix caprea , Salix daphnoides, Saxifraga stolonifera, Sideroxylon inerme, Sideroxylon inerme L. , Taxus mairei, Thujopsis dolobrata, Trichilia catigua, Uncaria gambir , Uncaria sinensis , Urceola micrantha, Vaccinium vitis-idaea , Vigna angularis , Zanthoxylum piperitum and Ziziphus jujuba. It was first documented in 2012 (PMID: 22042007). Based on a literature review a significant number of articles have been published on Procyanidin B2 (PMID: 23250807) (PMID: 23285083) (PMID: 23360097) (PMID: 23460126).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123523D          

 68 73  0  0  0  0            999 V2000
   -3.4448   -4.6024    0.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185   -4.0375    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7358   -3.9768    2.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -3.3514    2.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101   -3.3183    3.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276   -2.7656    1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806   -2.8606    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937   -3.5018   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3774   -2.3912   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884   -1.3195   -0.7558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9719   -0.8713   -2.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    0.4555   -2.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782    0.8992   -3.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2638    0.0125   -4.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850    0.3852   -5.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8148   -1.3006   -4.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -2.1667   -5.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -1.7497   -3.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079   -1.7524    0.3142 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0815   -2.8969   -0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -2.1292    1.6262 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6599   -0.9607    2.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7548   -0.8628    3.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8134   -1.7324    3.4985 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8496    0.1587    4.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8751    1.1444    4.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9602    2.1561    5.3975 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8051    1.1351    3.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908    0.0665    2.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    0.0241    1.7571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063    0.7718    2.1328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5725    0.5186    1.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8239    1.3875    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8097    1.0935   -0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402   -0.0773   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4993   -0.3635   -1.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980   -0.9602    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0276   -2.1170    0.2552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306   -0.6662    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153    2.2371    2.3931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4009    2.8215    1.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061    2.2589    3.6203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5796   -4.7049   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -4.4173    2.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -3.8094    4.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -3.5442   -1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6942   -0.4646   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2926    1.1563   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4210    1.9271   -3.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304    1.3230   -5.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634   -1.6341   -5.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358   -2.7810   -3.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0437   -0.9573    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -3.4708   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.9632    2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8611   -2.2283    2.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7002    0.1751    5.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527    2.0180    5.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9015    0.3520    3.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    2.3094   -0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990    1.7740   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8875   -1.2072   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214   -2.7060    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1488   -1.3539    1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9962    2.8624    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    2.1711    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121    2.1407    4.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3151    3.2225    3.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0  0  0  0
 18 16  1  0  0  0  0
 22 23  2  0  0  0  0
  7  8  1  0  0  0  0
 23 25  1  0  0  0  0
  8  2  2  0  0  0  0
 25 26  2  0  0  0  0
 26 28  1  0  0  0  0
 29 22  1  0  0  0  0
 29 28  2  0  0  0  0
  7  6  2  0  0  0  0
 13 12  2  0  0  0  0
 12 11  1  0  0  0  0
 11 18  2  0  0  0  0
 14 15  1  0  0  0  0
 16 14  2  0  0  0  0
 29 30  1  0  0  0  0
 28 42  1  0  0  0  0
 42 40  1  0  0  0  0
 40 31  1  0  0  0  0
 31 30  1  0  0  0  0
 26 27  1  0  0  0  0
  7  9  1  0  0  0  0
 31 32  1  0  0  0  0
  6 21  1  0  0  0  0
 40 41  1  0  0  0  0
 21 19  1  0  0  0  0
 32 39  2  0  0  0  0
 19 10  1  0  0  0  0
 39 37  1  0  0  0  0
 10  9  1  0  0  0  0
 37 35  2  0  0  0  0
  2  3  1  0  0  0  0
 35 34  1  0  0  0  0
  2  1  1  0  0  0  0
 34 33  2  0  0  0  0
 33 32  1  0  0  0  0
 14 13  1  0  0  0  0
 35 36  1  0  0  0  0
  4  5  1  0  0  0  0
 37 38  1  0  0  0  0
 21 22  1  0  0  0  0
  3  4  2  0  0  0  0
 23 24  1  0  0  0  0
 19 20  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 18 52  1  0  0  0  0
 13 49  1  0  0  0  0
 12 48  1  0  0  0  0
 15 50  1  0  0  0  0
  3 44  1  0  0  0  0
  8 46  1  0  0  0  0
 21 55  1  1  0  0  0
 19 53  1  1  0  0  0
 10 47  1  1  0  0  0
  1 43  1  0  0  0  0
  5 45  1  0  0  0  0
 20 54  1  0  0  0  0
 25 57  1  0  0  0  0
 42 67  1  0  0  0  0
 42 68  1  0  0  0  0
 40 65  1  1  0  0  0
 31 59  1  1  0  0  0
 27 58  1  0  0  0  0
 41 66  1  0  0  0  0
 39 64  1  0  0  0  0
 34 61  1  0  0  0  0
 33 60  1  0  0  0  0
 36 62  1  0  0  0  0
 38 63  1  0  0  0  0
 24 56  1  0  0  0  0
 17 51  1  0  0  0  0
M  END

     RDKit          3D

 68 73  0  0  0  0  0  0  0  0999 V2000
   -3.4448   -4.6024    0.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185   -4.0375    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7358   -3.9768    2.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -3.3514    2.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101   -3.3183    3.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276   -2.7656    1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806   -2.8606    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937   -3.5018   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3774   -2.3912   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884   -1.3195   -0.7558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9719   -0.8713   -2.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    0.4555   -2.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782    0.8992   -3.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2638    0.0125   -4.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850    0.3852   -5.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8148   -1.3006   -4.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -2.1667   -5.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -1.7497   -3.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079   -1.7524    0.3142 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0815   -2.8969   -0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -2.1292    1.6262 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6599   -0.9607    2.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7548   -0.8628    3.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8134   -1.7324    3.4985 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8496    0.1587    4.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8751    1.1444    4.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9602    2.1561    5.3975 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8051    1.1351    3.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908    0.0665    2.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    0.0241    1.7571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063    0.7718    2.1328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5725    0.5186    1.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8239    1.3875    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8097    1.0935   -0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402   -0.0773   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4993   -0.3635   -1.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980   -0.9602    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0276   -2.1170    0.2552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306   -0.6662    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153    2.2371    2.3931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4009    2.8215    1.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061    2.2589    3.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5796   -4.7049   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -4.4173    2.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -3.8094    4.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -3.5442   -1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6942   -0.4646   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2926    1.1563   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4210    1.9271   -3.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304    1.3230   -5.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634   -1.6341   -5.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358   -2.7810   -3.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0437   -0.9573    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -3.4708   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.9632    2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8611   -2.2283    2.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7002    0.1751    5.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527    2.0180    5.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9015    0.3520    3.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    2.3094   -0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990    1.7740   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8875   -1.2072   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214   -2.7060    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1488   -1.3539    1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9962    2.8624    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    2.1711    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121    2.1407    4.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3151    3.2225    3.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0
 18 16  1  0
 22 23  2  0
  7  8  1  0
 23 25  1  0
  8  2  2  0
 25 26  2  0
 26 28  1  0
 29 22  1  0
 29 28  2  0
  7  6  2  0
 13 12  2  0
 12 11  1  0
 11 18  2  0
 14 15  1  0
 16 14  2  0
 29 30  1  0
 28 42  1  0
 42 40  1  0
 40 31  1  0
 31 30  1  0
 26 27  1  0
  7  9  1  0
 31 32  1  0
  6 21  1  0
 40 41  1  0
 21 19  1  0
 32 39  2  0
 19 10  1  0
 39 37  1  0
 10  9  1  0
 37 35  2  0
  2  3  1  0
 35 34  1  0
  2  1  1  0
 34 33  2  0
 33 32  1  0
 14 13  1  0
 35 36  1  0
  4  5  1  0
 37 38  1  0
 21 22  1  0
  3  4  2  0
 23 24  1  0
 19 20  1  0
 16 17  1  0
 10 11  1  0
 18 52  1  0
 13 49  1  0
 12 48  1  0
 15 50  1  0
  3 44  1  0
  8 46  1  0
 21 55  1  1
 19 53  1  1
 10 47  1  1
  1 43  1  0
  5 45  1  0
 20 54  1  0
 25 57  1  0
 42 67  1  0
 42 68  1  0
 40 65  1  1
 31 59  1  1
 27 58  1  0
 41 66  1  0
 39 64  1  0
 34 61  1  0
 33 60  1  0
 36 62  1  0
 38 63  1  0
 24 56  1  0
 17 51  1  0
M  END


  Mrv1652306192123523D          

 68 73  0  0  0  0            999 V2000
   -3.4448   -4.6024    0.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185   -4.0375    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7358   -3.9768    2.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -3.3514    2.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101   -3.3183    3.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276   -2.7656    1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806   -2.8606    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937   -3.5018   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3774   -2.3912   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884   -1.3195   -0.7558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9719   -0.8713   -2.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    0.4555   -2.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782    0.8992   -3.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2638    0.0125   -4.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850    0.3852   -5.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8148   -1.3006   -4.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -2.1667   -5.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -1.7497   -3.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079   -1.7524    0.3142 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0815   -2.8969   -0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -2.1292    1.6262 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6599   -0.9607    2.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7548   -0.8628    3.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8134   -1.7324    3.4985 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8496    0.1587    4.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8751    1.1444    4.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9602    2.1561    5.3975 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8051    1.1351    3.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908    0.0665    2.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    0.0241    1.7571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063    0.7718    2.1328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5725    0.5186    1.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8239    1.3875    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8097    1.0935   -0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402   -0.0773   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4993   -0.3635   -1.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980   -0.9602    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0276   -2.1170    0.2552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306   -0.6662    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153    2.2371    2.3931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4009    2.8215    1.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061    2.2589    3.6203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5796   -4.7049   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -4.4173    2.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -3.8094    4.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -3.5442   -1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6942   -0.4646   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2926    1.1563   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4210    1.9271   -3.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304    1.3230   -5.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634   -1.6341   -5.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358   -2.7810   -3.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0437   -0.9573    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -3.4708   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.9632    2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8611   -2.2283    2.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7002    0.1751    5.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527    2.0180    5.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9015    0.3520    3.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    2.3094   -0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990    1.7740   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8875   -1.2072   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214   -2.7060    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1488   -1.3539    1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9962    2.8624    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    2.1711    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121    2.1407    4.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3151    3.2225    3.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0  0  0  0
 18 16  1  0  0  0  0
 22 23  2  0  0  0  0
  7  8  1  0  0  0  0
 23 25  1  0  0  0  0
  8  2  2  0  0  0  0
 25 26  2  0  0  0  0
 26 28  1  0  0  0  0
 29 22  1  0  0  0  0
 29 28  2  0  0  0  0
  7  6  2  0  0  0  0
 13 12  2  0  0  0  0
 12 11  1  0  0  0  0
 11 18  2  0  0  0  0
 14 15  1  0  0  0  0
 16 14  2  0  0  0  0
 29 30  1  0  0  0  0
 28 42  1  0  0  0  0
 42 40  1  0  0  0  0
 40 31  1  0  0  0  0
 31 30  1  0  0  0  0
 26 27  1  0  0  0  0
  7  9  1  0  0  0  0
 31 32  1  0  0  0  0
  6 21  1  0  0  0  0
 40 41  1  0  0  0  0
 21 19  1  0  0  0  0
 32 39  2  0  0  0  0
 19 10  1  0  0  0  0
 39 37  1  0  0  0  0
 10  9  1  0  0  0  0
 37 35  2  0  0  0  0
  2  3  1  0  0  0  0
 35 34  1  0  0  0  0
  2  1  1  0  0  0  0
 34 33  2  0  0  0  0
 33 32  1  0  0  0  0
 14 13  1  0  0  0  0
 35 36  1  0  0  0  0
  4  5  1  0  0  0  0
 37 38  1  0  0  0  0
 21 22  1  0  0  0  0
  3  4  2  0  0  0  0
 23 24  1  0  0  0  0
 19 20  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 18 52  1  0  0  0  0
 13 49  1  0  0  0  0
 12 48  1  0  0  0  0
 15 50  1  0  0  0  0
  3 44  1  0  0  0  0
  8 46  1  0  0  0  0
 21 55  1  1  0  0  0
 19 53  1  1  0  0  0
 10 47  1  1  0  0  0
  1 43  1  0  0  0  0
  5 45  1  0  0  0  0
 20 54  1  0  0  0  0
 25 57  1  0  0  0  0
 42 67  1  0  0  0  0
 42 68  1  0  0  0  0
 40 65  1  1  0  0  0
 31 59  1  1  0  0  0
 27 58  1  0  0  0  0
 41 66  1  0  0  0  0
 39 64  1  0  0  0  0
 34 61  1  0  0  0  0
 33 60  1  0  0  0  0
 36 62  1  0  0  0  0
 38 63  1  0  0  0  0
 24 56  1  0  0  0  0
 17 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030547

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(O[H])=C1[H])[C@]([H])(C1=C(O[H])C([H])=C(O[H])C3=C1O[C@]([H])(C1=C([H])C(O[H])=C(O[H])C([H])=C1[H])[C@]([H])(O[H])C3([H])[H])[C@@]([H])(O[H])[C@]([H])(O2)C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

> <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-/m1/s1

> <INCHI_KEY>
XFZJEEAOWLFHDH-NFJBMHMQSA-N

> <FORMULA>
C30H26O12

> <MOLECULAR_WEIGHT>
578.526

> <EXACT_MASS>
578.142426277

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
57.15317190753751

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-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 B2

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 73  0  0  0  0  0  0  0  0999 V2000
   -3.4448   -4.6024    0.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185   -4.0375    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7358   -3.9768    2.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -3.3514    2.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101   -3.3183    3.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276   -2.7656    1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806   -2.8606    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937   -3.5018   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3774   -2.3912   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884   -1.3195   -0.7558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9719   -0.8713   -2.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    0.4555   -2.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782    0.8992   -3.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2638    0.0125   -4.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850    0.3852   -5.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8148   -1.3006   -4.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -2.1667   -5.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -1.7497   -3.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079   -1.7524    0.3142 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0815   -2.8969   -0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -2.1292    1.6262 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6599   -0.9607    2.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7548   -0.8628    3.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8134   -1.7324    3.4985 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8496    0.1587    4.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8751    1.1444    4.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9602    2.1561    5.3975 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8051    1.1351    3.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908    0.0665    2.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    0.0241    1.7571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063    0.7718    2.1328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5725    0.5186    1.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8239    1.3875    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8097    1.0935   -0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402   -0.0773   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4993   -0.3635   -1.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980   -0.9602    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0276   -2.1170    0.2552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306   -0.6662    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153    2.2371    2.3931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4009    2.8215    1.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061    2.2589    3.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5796   -4.7049   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -4.4173    2.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -3.8094    4.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -3.5442   -1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6942   -0.4646   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2926    1.1563   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4210    1.9271   -3.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304    1.3230   -5.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634   -1.6341   -5.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358   -2.7810   -3.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0437   -0.9573    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -3.4708   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.9632    2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8611   -2.2283    2.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7002    0.1751    5.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527    2.0180    5.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9015    0.3520    3.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    2.3094   -0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990    1.7740   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8875   -1.2072   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214   -2.7060    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1488   -1.3539    1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9962    2.8624    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    2.1711    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121    2.1407    4.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3151    3.2225    3.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0
 18 16  1  0
 22 23  2  0
  7  8  1  0
 23 25  1  0
  8  2  2  0
 25 26  2  0
 26 28  1  0
 29 22  1  0
 29 28  2  0
  7  6  2  0
 13 12  2  0
 12 11  1  0
 11 18  2  0
 14 15  1  0
 16 14  2  0
 29 30  1  0
 28 42  1  0
 42 40  1  0
 40 31  1  0
 31 30  1  0
 26 27  1  0
  7  9  1  0
 31 32  1  0
  6 21  1  0
 40 41  1  0
 21 19  1  0
 32 39  2  0
 19 10  1  0
 39 37  1  0
 10  9  1  0
 37 35  2  0
  2  3  1  0
 35 34  1  0
  2  1  1  0
 34 33  2  0
 33 32  1  0
 14 13  1  0
 35 36  1  0
  4  5  1  0
 37 38  1  0
 21 22  1  0
  3  4  2  0
 23 24  1  0
 19 20  1  0
 16 17  1  0
 10 11  1  0
 18 52  1  0
 13 49  1  0
 12 48  1  0
 15 50  1  0
  3 44  1  0
  8 46  1  0
 21 55  1  1
 19 53  1  1
 10 47  1  1
  1 43  1  0
  5 45  1  0
 20 54  1  0
 25 57  1  0
 42 67  1  0
 42 68  1  0
 40 65  1  1
 31 59  1  1
 27 58  1  0
 41 66  1  0
 39 64  1  0
 34 61  1  0
 33 60  1  0
 36 62  1  0
 38 63  1  0
 24 56  1  0
 17 51  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -3.445  -4.602   0.667  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.219  -4.037   0.867  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.736  -3.977   2.167  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.513  -3.351   2.409  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.010  -3.318   3.679  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.228  -2.766   1.370  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.281  -2.861   0.067  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.494  -3.502  -0.190  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.377  -2.391  -1.039  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.288  -1.319  -0.756  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.972  -0.871  -2.041  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.435   0.456  -2.154  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.078   0.899  -3.314  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.264   0.013  -4.366  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.885   0.385  -5.526  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.815  -1.301  -4.265  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.003  -2.167  -5.304  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.174  -1.750  -3.118  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.308  -1.752   0.314  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.082  -2.897  -0.108  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.584  -2.129   1.626  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.660  -0.961   2.614  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.755  -0.863   3.497  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.813  -1.732   3.498  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.850   0.159   4.440  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.875   1.144   4.483  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.960   2.156   5.397  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.805   1.135   3.586  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.691   0.067   2.672  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.335   0.024   1.757  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.506   0.772   2.133  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.572   0.519   1.077  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.824   1.387   0.002  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.810   1.093  -0.947  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.540  -0.077  -0.832  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.499  -0.364  -1.760  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.298  -0.960   0.213  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.028  -2.117   0.255  0.00  0.00           O+0
HETATM   39  C   UNK     0      -3.331  -0.666   1.168  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.115   2.237   2.393  0.00  0.00           C+0
HETATM   41  O   UNK     0      -0.401   2.821   1.290  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.206   2.259   3.620  0.00  0.00           C+0
HETATM   43  H   UNK     0      -3.580  -4.705  -0.294  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.315  -4.417   2.972  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.600  -3.809   4.274  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.864  -3.544  -1.210  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.694  -0.465  -0.412  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.293   1.156  -1.333  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.421   1.927  -3.373  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.130   1.323  -5.448  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.463  -1.634  -5.983  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.836  -2.781  -3.074  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.044  -0.957   0.484  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.477  -3.471  -0.618  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.143  -2.963   2.074  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.861  -2.228   2.664  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.700   0.175   5.114  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.753   2.018   5.943  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.902   0.352   3.071  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.262   2.309  -0.124  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.999   1.774  -1.772  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.888  -1.207  -1.454  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.621  -2.706   0.921  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.149  -1.354   1.989  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.996   2.862   2.574  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.274   2.171   1.022  0.00  0.00           H+0
HETATM   67  H   UNK     0      -0.812   2.141   4.527  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.315   3.223   3.669  0.00  0.00           H+0
CONECT    1    2   43                                                       
CONECT    2    8    3    1                                                  
CONECT    3    2    4   44                                                  
CONECT    4    6    5    3                                                  
CONECT    5    4   45                                                       
CONECT    6    4    7   21                                                  
CONECT    7    8    6    9                                                  
CONECT    8    7    2   46                                                  
CONECT    9    7   10                                                       
CONECT   10   19    9   11   47                                             
CONECT   11   12   18   10                                                  
CONECT   12   13   11   48                                                  
CONECT   13   12   14   49                                                  
CONECT   14   15   16   13                                                  
CONECT   15   14   50                                                       
CONECT   16   18   14   17                                                  
CONECT   17   16   51                                                       
CONECT   18   16   11   52                                                  
CONECT   19   21   10   20   53                                             
CONECT   20   19   54                                                       
CONECT   21    6   19   22   55                                             
CONECT   22   23   29   21                                                  
CONECT   23   22   25   24                                                  
CONECT   24   23   56                                                       
CONECT   25   23   26   57                                                  
CONECT   26   25   28   27                                                  
CONECT   27   26   58                                                       
CONECT   28   26   29   42                                                  
CONECT   29   22   28   30                                                  
CONECT   30   29   31                                                       
CONECT   31   40   30   32   59                                             
CONECT   32   31   39   33                                                  
CONECT   33   34   32   60                                                  
CONECT   34   35   33   61                                                  
CONECT   35   37   34   36                                                  
CONECT   36   35   62                                                       
CONECT   37   39   35   38                                                  
CONECT   38   37   63                                                       
CONECT   39   32   37   64                                                  
CONECT   40   42   31   41   65                                             
CONECT   41   40   66                                                       
CONECT   42   28   40   67   68                                             
CONECT   43    1                                                            
CONECT   44    3                                                            
CONECT   45    5                                                            
CONECT   46    8                                                            
CONECT   47   10                                                            
CONECT   48   12                                                            
CONECT   49   13                                                            
CONECT   50   15                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   27                                                            
CONECT   59   31                                                            
CONECT   60   33                                                            
CONECT   61   34                                                            
CONECT   62   36                                                            
CONECT   63   38                                                            
CONECT   64   39                                                            
CONECT   65   40                                                            
CONECT   66   41                                                            
CONECT   67   42                                                            
CONECT   68   42                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  146    0
END

RDKit          3D

68 73  0  0  0  0  0  0  0  0999 V2000
   -3.4448   -4.6024    0.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185   -4.0375    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7358   -3.9768    2.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5133   -3.3514    2.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101   -3.3183    3.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276   -2.7656    1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806   -2.8606    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937   -3.5018   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3774   -2.3912   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884   -1.3195   -0.7558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9719   -0.8713   -2.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    0.4555   -2.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782    0.8992   -3.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2638    0.0125   -4.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850    0.3852   -5.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8148   -1.3006   -4.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032   -2.1667   -5.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -1.7497   -3.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079   -1.7524    0.3142 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0815   -2.8969   -0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -2.1292    1.6262 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6599   -0.9607    2.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7548   -0.8628    3.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8134   -1.7324    3.4985 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8496    0.1587    4.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8751    1.1444    4.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9602    2.1561    5.3975 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8051    1.1351    3.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908    0.0665    2.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    0.0241    1.7571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063    0.7718    2.1328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5725    0.5186    1.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8239    1.3875    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8097    1.0935   -0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402   -0.0773   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4993   -0.3635   -1.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980   -0.9602    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0276   -2.1170    0.2552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306   -0.6662    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153    2.2371    2.3931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4009    2.8215    1.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061    2.2589    3.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5796   -4.7049   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -4.4173    2.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -3.8094    4.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -3.5442   -1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6942   -0.4646   -0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2926    1.1563   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4210    1.9271   -3.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304    1.3230   -5.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634   -1.6341   -5.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8358   -2.7810   -3.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0437   -0.9573    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -3.4708   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.9632    2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8611   -2.2283    2.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7002    0.1751    5.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527    2.0180    5.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9015    0.3520    3.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    2.3094   -0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990    1.7740   -1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8875   -1.2072   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214   -2.7060    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1488   -1.3539    1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9962    2.8624    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    2.1711    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121    2.1407    4.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3151    3.2225    3.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0
 18 16  1  0
 22 23  2  0
  7  8  1  0
 23 25  1  0
  8  2  2  0
 25 26  2  0
 26 28  1  0
 29 22  1  0
 29 28  2  0
  7  6  2  0
 13 12  2  0
 12 11  1  0
 11 18  2  0
 14 15  1  0
 16 14  2  0
 29 30  1  0
 28 42  1  0
 42 40  1  0
 40 31  1  0
 31 30  1  0
 26 27  1  0
  7  9  1  0
 31 32  1  0
  6 21  1  0
 40 41  1  0
 21 19  1  0
 32 39  2  0
 19 10  1  0
 39 37  1  0
 10  9  1  0
 37 35  2  0
  2  3  1  0
 35 34  1  0
  2  1  1  0
 34 33  2  0
 33 32  1  0
 14 13  1  0
 35 36  1  0
  4  5  1  0
 37 38  1  0
 21 22  1  0
  3  4  2  0
 23 24  1  0
 19 20  1  0
 16 17  1  0
 10 11  1  0
 18 52  1  0
 13 49  1  0
 12 48  1  0
 15 50  1  0
  3 44  1  0
  8 46  1  0
 21 55  1  1
 19 53  1  1
 10 47  1  1
  1 43  1  0
  5 45  1  0
 20 54  1  0
 25 57  1  0
 42 67  1  0
 42 68  1  0
 40 65  1  1
 31 59  1  1
 27 58  1  0
 41 66  1  0
 39 64  1  0
 34 61  1  0
 33 60  1  0
 36 62  1  0
 38 63  1  0
 24 56  1  0
 17 51  1  0
M  END

View in JSmol

Synonyms

Value	Source
EC-(4b,8)-ec	ChEBI
Epicathechin-(4beta->8)-epicathechin	ChEBI
Proanthocyanidin b2	ChEBI
Procyanidol b2	ChEBI
Epicathechin-(4b->8)-epicathechin	Generator
Epicathechin-(4β->8)-epicathechin	Generator
(+)-Procyanidin b2	HMDB
2,3-cis-Proanthocyanidin	HMDB
cis,Cis"-4,8"-bi(3,3',4',5,7-pentahydroxyflavane)	HMDB
Procyanidin dimer b2	HMDB

Chemical Formula

C₃₀H₂₆O₁₂

Average Mass

578.5260 Da

Monoisotopic Mass

578.14243 Da

IUPAC Name

(2R,3R)-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 B2

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C(O[H])=C1[H])[C@]([H])(C1=C(O[H])C([H])=C(O[H])C3=C1O[C@]([H])(C1=C([H])C(O[H])=C(O[H])C([H])=C1[H])[C@]([H])(O[H])C3([H])[H])[C@@]([H])(O[H])[C@]([H])(O2)C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

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-/m1/s1

InChI Key

XFZJEEAOWLFHDH-NFJBMHMQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinidia chinensis	FooDB	PHENOL EXPLORER
Aesculus hippocastanum	KNApSAcK Database	22123792
Albizia lebbeck	LOTUS Database	35616633
Alhagi sparsifolia	LOTUS Database	35616633
Ananas comosus	FooDB	PHENOL EXPLORER
Annona reticulata	FooDB	PHENOL EXPLORER
Apis cerana	LOTUS Database	35616633
Apocynum venetum	LOTUS Database	35616633
Arachis hypogaea	KNApSAcK Database	22123792
Areca catechu	Plant	KNApSAcK
Averrhoa carambola	FooDB	KNAPSACK
Averrhoa carambola L.	KNApSAcK Database	22123792
Banisteriopsis caapi	LOTUS Database	35616633
Begonia fagifolia	LOTUS Database	35616633
Bergenia purpurascens	Plant	KNApSAcK
Betula pubescens	Plant	KNApSAcK
Byrsonima crassifolia	Plant	KNApSAcK
Calluna vulgaris	Plant	KNApSAcK
Camellia japonica	Plant	KNApSAcK
Camellia reticulata	LOTUS Database	35616633
Camellia sinensis	KNApSAcK Database	22123792
Camellia sinensis var.assamica	Plant	KNApSAcK
Campylotropis hirella	Plant	KNApSAcK
Capsicum annuum	FooDB	PHENOL EXPLORER
Cassia fistula	Plant	KNApSAcK
Castanea	FooDB	PHENOL EXPLORER
Cecropia glaziovii	LOTUS Database	35616633
Chamaerops humilis	Plant	KNApSAcK
Cicer arietinum	FooDB	PHENOL EXPLORER
Cinchona pubescens	LOTUS Database	35616633
Cinnamomum	FooDB	KNAPSACK
Cinnamomum aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum bejolghota	LOTUS Database	35616633
Cinnamomum burmanni	LOTUS Database	35616633
Cinnamomum camphora	Plant	KNApSAcK
Cinnamomum cassia Blume.	KNApSAcK Database	22123792
Cinnamomum cirrhosa	Plant	KNApSAcK
Cinnamomum obtusifolium Nees.	KNApSAcK Database	22123792
Cinnamomum spp.	KNApSAcK Database	22123792
Cinnamomum verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cistus incanus	Plant	KNApSAcK
Cola nitida	LOTUS Database	35616633
Coleogyne ramosissima	LOTUS Database	35616633
Coleogyne ramosissima Torr.	KNApSAcK Database	22123792
Cotoneaster spp.	KNApSAcK Database	22123792
Crataegus laevigata	LOTUS Database	35616633
Crataegus monogyma	JEOL database	Khan, M. L., et al, Magn. Reson. Chem. 35, 854 (1997)
Crataegus monogyna	Plant	KNApSAcK
Crataegus pinnatifida var major	KNApSAcK Database	22123792
Crataegus sinaica	LOTUS Database	35616633
Crataegus spp.	KNApSAcK Database	22123792
Croton lechleri	LOTUS Database	35616633
Cryptocarya obovata	LOTUS Database	35616633
Cucurbita	FooDB	PHENOL EXPLORER
Cydonia oblonga	FooDB	PHENOL EXPLORER
Daucus carota ssp. sativus	FooDB	PHENOL EXPLORER
Davallia divaricata	LOTUS Database	35616633
Davallia mariesii	KNApSAcK Database	22123792
Dioscorea alata	Plant	KNApSAcK
Dioscorea bulbifera	Plant	KNApSAcK
Dioscorea cirrhosa	LOTUS Database	35616633
Diospyros kaki	FooDB	PHENOL EXPLORER
Ecdysanthera utilis	KNApSAcK Database	22123792
Eriobotrya japonica	KNApSAcK Database	22123792
Fagopyrum cymosum	Plant	KNApSAcK
Fagopyrum esculentum	KNApSAcK Database	22123792
Fagopyrum homotropicum	KNApSAcK Database	22123792
Fallopia multiflora	LOTUS Database	35616633
Ficus carica	FooDB	PHENOL EXPLORER
Fragaria spp.	Plant	KNApSAcK
Fragaria vesca	Plant	KNApSAcK
Fragaria x ananassa	FooDB	PHENOL EXPLORER
Garcinia mangostana	LOTUS Database	35616633
Geranium sanguineum	LOTUS Database	35616633
Guazuma ulmifolia	KNApSAcK Database	22123792
Humulus lupulus	LOTUS Database	35616633
Hypericum erectum	LOTUS Database	35616633
Juniperus sabina	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Lactuca sativa	FooDB	PHENOL EXPLORER
Larix gmelini	Plant	KNApSAcK
Laurus nobilis	KNApSAcK Database	22123792
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lens culinaris	FooDB	PHENOL EXPLORER
Lindera umbellata	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Lotus uliginosus	LOTUS Database	35616633
Malus	FooDB	KNAPSACK
Malus domestica	LOTUS Database	35616633
Malus pumila	FooDB	9818410
Malus spp.	KNApSAcK Database	22123792
Malus sylvestris	LOTUS Database	35616633
Maytenus senegalensis	LOTUS Database	35616633
Melastoma candidum	LOTUS Database	35616633
Mespilus germanica	FooDB	PHENOL EXPLORER
Metroxylon sagu	Plant	KNApSAcK
Metroxylon sagus	Plant	KNApSAcK
Musa acuminata	FooDB	PHENOL EXPLORER
Nelia pillansii	LOTUS Database	35616633
Paullinia cupana	LOTUS Database	35616633
Persea americana	FooDB	PHENOL EXPLORER
Persea gratissima	KNApSAcK Database	22123792
Phaseolus vulgaris	FooDB	PHENOL EXPLORER
Picea abies	Plant	KNApSAcK
Pinus sylvestris	LOTUS Database	35616633
Pisum sativum	FooDB	PHENOL EXPLORER
Platanus orientalis	LOTUS Database	35616633
Populus canescens	Plant	KNApSAcK
Potentilla erecta	Plant	KNApSAcK
Potentilla viscosa	Plant	KNApSAcK
Prunus armeniaca	FooDB	PHENOL EXPLORER
Prunus avium	FooDB	PHENOL EXPLORER
Prunus domestica	FooDB	PHENOL EXPLORER
Prunus dulcis	LOTUS Database	35616633
Prunus persica var. persica	FooDB	PHENOL EXPLORER
Pseudotsuga menziesii	LOTUS Database	35616633
Psidium guajava	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psorospermum febrifugum	LOTUS Database	35616633
Punica granatum	KNApSAcK Database	22123792
Pyrola incarnata	Plant	KNApSAcK
Pyrus communis	FooDB	PHENOL EXPLORER
Pyrus spp.	Plant	KNApSAcK
Quercus marilandica	Plant	KNApSAcK
Quercus miyagii	Plant	KNApSAcK
Rheum sp.	Plant	KNApSAcK
Rhizophora stylosa	LOTUS Database	35616633
Ribes rubrum	FooDB	PHENOL EXPLORER
Riedeliella graciliflora	Plant	KNApSAcK
Rosa cymosa	Plant	KNApSAcK
Rosa henryi	Plant	KNApSAcK
Rosa laevigata	Plant	KNApSAcK
Rubus chamaemorus	FooDB	PHENOL EXPLORER
Rubus idaeus	FooDB	PHENOL EXPLORER
Rubus spp.	Plant	KNApSAcK
Rumex acetosa	LOTUS Database	35616633
Salix caprea	Plant	KNApSAcK
Salix daphnoides	Plant	KNApSAcK
Saraca asoca	KNApSAcK Database	22123792
Saxifraga stolonifera	LOTUS Database	35616633
Sideroxylon inerme	LOTUS Database	35616633
Sideroxylon inerme L.	Plant	KNApSAcK
Solanum lycopersicum var. lycopersicum	FooDB	PHENOL EXPLORER
Solanum melongena	FooDB	PHENOL EXPLORER
Taxus mairei	LOTUS Database	35616633
Theobroma cacao	KNApSAcK Database	22123792
Thujopsis dolabrata	Plant	KNApSAcK
Trichilia catigua	LOTUS Database	35616633
Triticum aestivum	FooDB	PHENOL EXPLORER
Uncaria gambir	Plant	KNApSAcK
Uncaria sinensis	Plant	KNApSAcK
Urceola micrantha	LOTUS Database	35616633
Vaccinium macrocarpon	KNApSAcK Database	22123792
Vaccinium myritillus	KNApSAcK Database	22123792
Vaccinium myrtillus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium vitis-idaea	Plant	KNApSAcK
Viburnum burkwoodii	KNApSAcK Database	22123792
Vicia faba	FooDB	PHENOL EXPLORER
Vigna angularis	Plant	KNApSAcK
Vitis labrusca	FooDB	PHENOL EXPLORER
Vitis vinifera	KNApSAcK Database	22123792
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zanthoxylum piperitum	LOTUS Database	35616633
Ziziphus jujuba	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:75632 )
proanthocyanidin (CHEBI:75632 )
biflavonoid (CHEBI:75632 )
hydroxyflavan (CHEBI:75632 )
Proanthocyanidins (C17639 )
Proanthocyanidins (LMPK12030002 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	955.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	20.86 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.300 (est)	The Good Scents Company Information System

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	57.15 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

HMDB0033973

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Procyanidin_B2

METLIN ID

Not Available

PubChem Compound

122738

PDB ID

Not Available

ChEBI ID

75632

Good Scents ID

rw1699201

References

General References

Rodriguez-Ramiro I, Ramos S, Bravo L, Goya L, Martin MA: Procyanidin B2 induces Nrf2 translocation and glutathione S-transferase P1 expression via ERKs and p38-MAPK pathways and protect human colonic cells against oxidative stress. Eur J Nutr. 2012 Oct;51(7):881-92. doi: 10.1007/s00394-011-0269-1. Epub 2011 Nov 1. [PubMed:22042007 ]
Braunlich M, Christensen H, Johannesen S, Slimestad R, Wangensteen H, Malterud KE, Barsett H: In vitro inhibition of cytochrome P450 3A4 by Aronia melanocarpa constituents. Planta Med. 2013 Jan;79(2):137-41. doi: 10.1055/s-0032-1328055. Epub 2012 Dec 18. [PubMed:23250807 ]
Yu F, Li BY, Li XL, Cai Q, Zhang Z, Cheng M, Yin M, Wang JF, Zhang JH, Lu WD, Zhou RH, Gao HQ: Proteomic analysis of aorta and protective effects of grape seed procyanidin B2 in db/db mice reveal a critical role of milk fat globule epidermal growth factor-8 in diabetic arterial damage. PLoS One. 2012;7(12):e52541. doi: 10.1371/journal.pone.0052541. Epub 2012 Dec 21. [PubMed:23285083 ]
Zardo DM, Silva KM, Guyot S, Nogueira A: Phenolic profile and antioxidant capacity of the principal apples produced in Brazil. Int J Food Sci Nutr. 2013 Aug;64(5):611-20. doi: 10.3109/09637486.2013.763909. Epub 2013 Jan 29. [PubMed:23360097 ]
Bai X, Zhang H, Ren S: Antioxidant activity and HPLC analysis of polyphenol-enriched extracts from industrial apple pomace. J Sci Food Agric. 2013 Aug 15;93(10):2502-6. doi: 10.1002/jsfa.6066. Epub 2013 Mar 4. [PubMed:23460126 ]
Khan, M. L., et al. (1997). Khan, M. L., et al, Magn. Reson. Chem. 35, 854 (1997). Mag. Reson. Chem..

Showing NP-Card for Procyanidin B2 (NP0030547)

MOL for NP0030547 (Procyanidin B2)

3D MOL for NP0030547 (Procyanidin B2)

3D SDF for NP0030547 (Procyanidin B2)

3D-SDF for NP0030547 (Procyanidin B2)

PDB for NP0030547 (Procyanidin B2)

3D PDB for NP0030547 (Procyanidin B2)

SMILES for NP0030547 (Procyanidin B2)

INCHI for NP0030547 (Procyanidin B2)

Structure for NP0030547 (Procyanidin B2)

3D Structure for NP0030547 (Procyanidin B2)