NP-MRD: Showing NP-Card for Procyanidin B5 (NP0049079)

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Record Information

Version

2.0

Created at

2022-03-17 21:06:48 UTC

Updated at

2022-03-17 21:06:48 UTC

NP-MRD ID

NP0049079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Procyanidin B5

Description

Procyanidin B5, also known as ec-(4b,6)-ec or procyanidol B5, 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''. Procyanidin B5 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Procyanidin B5 is found, on average, in the highest concentration within a few different foods, such as european plums, apples, and custard apples and in a lower concentration in peach (var.), Sweet cherries, and tea. Procyanidin B5 has also been detected, but not quantified in, several different foods, such as yellow zucchinis, grape wines, kiwis, ceylon cinnamons, and common pea. Procyanidin B5 is found in Aesculus hippocastanum , Areca catechu , Betula spp., Calluna vulgaris , Campylotropis hirella, Cinnamomum bejolghota, Cinnamomum cassia Blume. , Cinnamomum comphora, Cinnamomum obtusifolium Nees., Cinnamomum spp., Cistus incanus, Coleogyne ramosissima Torr., Davallia mariesii, Dioscorea cirrhosa, Fagopyrum homotropicum, Fragaria spp., Garcinia mangostana , Illicium anisatum , Malus sylvestris , Picea abies , Pinus radiata, Pinus sylvestris , Pinus taeda, Quercus miyagii, Quercus petraea , Quercus spp., Rheum sp., Rhododendron ponticum, Rosa cymosa, Rubus fruticosus , Rubus spp. , Rumex thyrsiflorus , Salix caprea , Salix sieboldiana, Salix spp. and Vaccinium vitis idaea. This could make procyanidin B5 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241219322D          

 42 47  0  0  0  0            999 V2000
   -0.4403   -1.0916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7972   -0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2097    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7972    1.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2097    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0347    0.3373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4472    1.0518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0347    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4472    2.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222    2.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2722    1.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222    1.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7472    1.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4403    1.7662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278    1.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4403    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2653    0.3373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6778    1.0518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2653    1.7662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979   -1.5766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2653   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778   -0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028   -0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028   -1.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778   -1.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153   -2.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153    0.3373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028    1.0518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9153    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028    2.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153    3.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028    3.9096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7403    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1528    2.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7403    3.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1528    3.9096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  6  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  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
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  6  0  0  0
 23 34  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 33  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  2  0  0  0  0
 35 39  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 41  2  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 22 21  1  1  0  0  0
M  END


  Mrv0541 02241219322D          

 42 47  0  0  0  0            999 V2000
   -0.4403   -1.0916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7972   -0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2097    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7972    1.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2097    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0347    0.3373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4472    1.0518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0347    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4472    2.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222    2.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2722    1.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222    1.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7472    1.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4403    1.7662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278    1.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4403    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2653    0.3373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6778    1.0518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2653    1.7662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979   -1.5766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2653   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778   -0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028   -0.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028   -1.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778   -1.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153   -2.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153    0.3373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028    1.0518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9153    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028    2.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153    3.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028    3.9096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7403    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1528    2.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7403    3.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1528    3.9096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  6  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  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
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  6  0  0  0
 23 34  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 33  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  2  0  0  0  0
 35 39  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 41  2  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 22 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0049079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(O[C@H]1C1=CC=C(O)C(O)=C1)C=C(O)C([C@@H]1[C@@H](O)[C@H](OC3=CC(O)=CC(O)=C13)C1=CC(O)=C(O)C=C1)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21?,26-,28-,29+,30-/m1/s1

> <INCHI_KEY>
GMISZFQPFDAPGI-WXXMRKNTSA-N

> <FORMULA>
C30H26O12

> <MOLECULAR_WEIGHT>
578.5202

> <EXACT_MASS>
578.142426296

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
57.18979630138711

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
3.1157450136666665

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.131417482712479

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.696085363131802

> <JCHEM_PKA_STRONGEST_BASIC>
-5.176745497915186

> <JCHEM_POLAR_SURFACE_AREA>
220.75999999999996

> <JCHEM_REFRACTIVITY>
146.50799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.822  -2.038   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.052  -0.704   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.488  -0.704   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.258   0.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.488   1.963   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.258   3.297   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.798   0.630   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.568   1.963   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.798   3.297   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.568   4.631   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.188   4.631   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.418   3.297   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.878   3.297   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.108   1.963   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.878   0.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.418   0.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.188   1.963   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.728   1.963   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.822   3.297   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.052   1.963   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.822   0.630   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.362   0.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.132   1.963   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.362   3.297   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.116  -2.943   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.362  -2.038   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.132  -0.704   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.672  -0.704   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.442  -2.038   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.672  -3.371   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.132  -3.371   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.442  -4.705   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.442   0.630   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.672   1.963   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.442   3.297   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.672   4.631   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.442   5.964   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.672   7.298   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.982   3.297   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -7.752   4.631   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.982   5.964   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -7.752   7.298   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    9                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    6    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14    8   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   18                                                  
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20    5   19   21                                                  
CONECT   21    2   20   22                                                  
CONECT   22   23   27   21                                                  
CONECT   23   22   24   34                                                  
CONECT   24   23                                                            
CONECT   25   26                                                            
CONECT   26   25   27   31                                                  
CONECT   27   22   26   28                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   26   30                                                       
CONECT   32   30                                                            
CONECT   33   28   34                                                       
CONECT   34   23   33   35                                                  
CONECT   35   34   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   41                                                  
CONECT   38   37                                                            
CONECT   39   35   40                                                       
CONECT   40   39   41                                                       
CONECT   41   37   40   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
EC-(4b,6)-ec	HMDB
Epicatechin(4b->6)epicatechin	HMDB
Epicatechin-(4beta-6)-epicatechin	HMDB
Proanthocyanidin b5	HMDB
Procyanidin dimer b5	HMDB
Procyanidol b5	HMDB

Chemical Formula

C₃₀H₂₆O₁₂

Average Mass

578.5202 Da

Monoisotopic Mass

578.14243 Da

IUPAC Name

(2S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

(2S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

CAS Registry Number

12798-57-1

SMILES

OC1CC2=C(O[C@H]1C1=CC=C(O)C(O)=C1)C=C(O)C([C@@H]1[C@@H](O)[C@H](OC3=CC(O)=CC(O)=C13)C1=CC(O)=C(O)C=C1)=C2O

InChI Identifier

InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21?,26-,28-,29+,30-/m1/s1

InChI Key

GMISZFQPFDAPGI-WXXMRKNTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinidia chinensis	FooDB	PHENOL EXPLORER
Aesculus hippocastanum	Plant	KNApSAcK
Ananas comosus	FooDB	PHENOL EXPLORER
Annona reticulata	FooDB	PHENOL EXPLORER
Areca catechu	Plant	KNApSAcK
Betula spp.	Plant	KNApSAcK
Calluna vulgaris	Plant	KNApSAcK
Campylotropis hirella	Plant	KNApSAcK
Capsicum annuum	FooDB	PHENOL EXPLORER
Castanea	FooDB	PHENOL EXPLORER
Cicer arietinum	FooDB	PHENOL EXPLORER
Cinnamomum	FooDB	KNAPSACK
Cinnamomum aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum bejolghota	Plant	KNApSAcK
Cinnamomum cassia Blume.	Plant	KNApSAcK
Cinnamomum comphora	Plant	KNApSAcK
Cinnamomum obtusifolium Nees.	Plant	KNApSAcK
Cinnamomum spp.	Plant	KNApSAcK
Cinnamomum verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cistus incanus	Plant	KNApSAcK
Coleogyne ramosissima Torr.	Plant	KNApSAcK
Cucurbita	FooDB	PHENOL EXPLORER
Cydonia oblonga	FooDB	PHENOL EXPLORER
Daucus carota ssp. sativus	FooDB	PHENOL EXPLORER
Davallia mariesii	Plant	KNApSAcK
Dioscorea cirrhosa	Plant	KNApSAcK
Diospyros kaki	FooDB	PHENOL EXPLORER
Fagopyrum esculentum	FooDB	KNAPSACK
Fagopyrum homotropicum	Plant	KNApSAcK
Ficus carica	FooDB	PHENOL EXPLORER
Fragaria spp.	Plant	KNApSAcK
Fragaria x ananassa	FooDB	PHENOL EXPLORER
Garcinia mangostana	Plant	KNApSAcK
Illicium anisatum	Plant	KNApSAcK
Lactuca sativa	FooDB	PHENOL EXPLORER
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lens culinaris	FooDB	PHENOL EXPLORER
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Malus sylvestris	Plant	KNApSAcK
Mespilus germanica	FooDB	PHENOL EXPLORER
Musa acuminata	FooDB	PHENOL EXPLORER
Persea americana	FooDB	PHENOL EXPLORER
Phaseolus vulgaris	FooDB	PHENOL EXPLORER
Picea abies	Plant	KNApSAcK
Pinus radiata	Plant	KNApSAcK
Pinus sylvestris	Plant	KNApSAcK
Pinus taeda	Plant	KNApSAcK
Pisum sativum	FooDB	PHENOL EXPLORER
Prunus armeniaca	FooDB	PHENOL EXPLORER
Prunus avium	FooDB	PHENOL EXPLORER
Prunus domestica	FooDB	PHENOL EXPLORER
Prunus persica var. persica	FooDB	PHENOL EXPLORER
Punica granatum	FooDB	PHENOL EXPLORER
Pyrus communis	FooDB	PHENOL EXPLORER
Quercus miyagii	Plant	KNApSAcK
Quercus petraea	Plant	KNApSAcK
Quercus spp.	Plant	KNApSAcK
Rheum sp.	Plant	KNApSAcK
Rhododendron ponticum	Plant	KNApSAcK
Ribes rubrum	FooDB	PHENOL EXPLORER
Rosa cymosa	Plant	KNApSAcK
Rubus fruticosus	Plant	KNApSAcK
Rubus idaeus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rubus spp.	Plant	KNApSAcK
Rumex thyrsiflorus	Plant	KNApSAcK
Salix caprea	Plant	KNApSAcK
Salix sieboldiana	Plant	KNApSAcK
Salix spp.	Plant	KNApSAcK
Solanum lycopersicum var. lycopersicum	FooDB	PHENOL EXPLORER
Solanum melongena	FooDB	PHENOL EXPLORER
Theobroma cacao	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Triticum aestivum	FooDB	PHENOL EXPLORER
Vaccinium vitis idaea	Plant	KNApSAcK
Vaccinium vitis-idaea	FooDB	KNAPSACK
Vicia faba	FooDB	PHENOL EXPLORER
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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

Not Available

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	2.31	ALOGPS
logP	3.12	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.7	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	57.19 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

HMDB0038366

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017706

KNApSAcK ID

C00009076

Chemspider ID

Not Available

KEGG Compound ID

C17640

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Procyanidin B5

METLIN ID

Not Available

PubChem Compound

131752343

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Procyanidin B5 (NP0049079)

MOL for NP0049079 (Procyanidin B5)

3D MOL for NP0049079 (Procyanidin B5)

3D SDF for NP0049079 (Procyanidin B5)

3D-SDF for NP0049079 (Procyanidin B5)

PDB for NP0049079 (Procyanidin B5)

3D PDB for NP0049079 (Procyanidin B5)

SMILES for NP0049079 (Procyanidin B5)

INCHI for NP0049079 (Procyanidin B5)

Structure for NP0049079 (Procyanidin B5)

3D Structure for NP0049079 (Procyanidin B5)