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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 18:22:57 UTC

Update Date

2021-09-23 18:22:57 UTC

HMDB ID

HMDB0302517

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Proanthocyanidins

Description

Proanthocyanidins, also known as zangrado or polyhydroxyflavan-3-ol, is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids 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''. Proanthocyanidins is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Proanthocyanidins can be found in a number of food items such as roselle, allspice, cocoa bean, and sweet bay, which makes proanthocyanidins a potential biomarker for the consumption of these food products. Proanthocyanidins were discovered in 1947 by Jacques Masquelier, who developed and patented techniques for the extraction of oligomeric proanthocyanidins from pine bark and grape seeds. Often associated with consumer products made from cranberries, grape seeds or red wine, proanthocyanidins were once proposed as factors inhibiting urinary tract infections in women, but this research has been refuted by expert scientific committees .

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1533007131513372D          

 48 53  0  0  1  0            999 V2000
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    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
 12  2  2  0  0  0  0
 12  3  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  4  2  0  0  0  0
 14  5  1  0  0  0  0
 15  8  2  0  0  0  0
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 27 46  1  1  0  0  0
 47 28  1  0  0  0  0
 29 48  1  1  0  0  0
M  END

HMDB0302517
     RDKit          3D
Proanthocyanidins
 71 76  0  0  0  0  0  0  0  0999 V2000
    7.5079    0.6600   -2.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1556    0.9376   -3.0261 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    1.1236   -2.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4445    0.0407   -1.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6872   -1.2499   -2.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4420    0.2655   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1561    1.5146   -0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972    1.7402    0.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338    1.0277    0.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6681   -0.1784    1.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4644   -0.6987    2.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8810   -2.8486    1.0052 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3182   -0.3598   -0.2706 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7656   -1.3839   -1.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8373   -2.2207   -1.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5053   -2.1026   -1.4758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165   -3.2047   -2.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5503   -3.3014   -3.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8962   -4.2983   -3.9681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4815   -2.4714   -2.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0964   -1.4895   -1.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446   -0.6530   -0.9921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7446   -0.1097    0.2872 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7779    0.8837    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2418    1.8303   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2058    2.7532    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7124    2.7404    1.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2614    1.8073    2.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3040    0.8943    1.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3991    0.5326    0.2445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5098    1.7271   -0.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6806    0.0480    2.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411    1.4788    2.1874 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9602    1.9900    2.1969 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958    2.5810   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8902    2.3765   -1.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6560    3.4363   -2.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8805    1.2370   -1.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1135   -1.9909   -1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0708    3.6916    2.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6798    1.8231    3.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1604    0.8807    1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3296    1.4755   -1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5566   -0.4963    2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    0.0003    3.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    2.1281    2.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3026    2.0832    3.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3857    3.3115   -2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
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  5 47  1  0
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 37 65  1  0
 38 66  1  0
 38 67  1  0
 39 68  1  1
 40 69  1  0
 41 70  1  0
 43 71  1  0
M  END

  Mrv1533007131513372D          

 48 53  0  0  1  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073    0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
 12  2  2  0  0  0  0
 12  3  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  4  2  0  0  0  0
 14  5  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 17 16  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
 20  6  1  0  0  0  0
 21  7  2  0  0  0  0
 22 10  1  0  0  0  0
 23  9  2  0  0  0  0
 24 18  2  0  0  0  0
 24 23  1  0  0  0  0
 25 19  2  0  0  0  0
 26 24  1  0  0  0  0
 26 25  1  1  0  0  0
 27 26  1  0  0  0  0
 28 13  1  0  0  0  0
 28 22  1  0  0  0  0
 29 12  1  6  0  0  0
 29 27  1  0  0  0  0
 30 16  2  0  0  0  0
 30 25  1  0  0  0  0
 31 20  2  0  0  0  0
 31 21  1  0  0  0  0
 32 14  1  0  0  0  0
 33 15  1  0  0  0  0
 34 17  1  0  0  0  0
 35 18  1  0  0  0  0
 36 19  1  0  0  0  0
 37 20  1  0  0  0  0
 38 21  1  0  0  0  0
 22 39  1  6  0  0  0
 27 40  1  6  0  0  0
 41  1  1  0  0  0  0
 41 31  1  0  0  0  0
 42 23  1  0  0  0  0
 42 29  1  0  0  0  0
 43 28  1  0  0  0  0
 43 30  1  0  0  0  0
 22 44  1  1  0  0  0
 26 45  1  6  0  0  0
 27 46  1  1  0  0  0
 47 28  1  0  0  0  0
 29 48  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302517

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(O)CC2=C(OC1([H])C1=CC(O)=C(OC)C(O)=C1)C(=C(O)C=C2O)[C@@]1([H])C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC=C(O)C=C2)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1

> <INCHI_KEY>
JPFCOVZKLAXXOE-XBNSMERZSA-N

> <FORMULA>
C31H28O12

> <MOLECULAR_WEIGHT>
592.553

> <EXACT_MASS>
592.158076342

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
58.52443308041734

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
3.261639069666667

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.288151039305365

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.859260425953432

> <JCHEM_PKA_STRONGEST_BASIC>
-3.460183570638237

> <JCHEM_POLAR_SURFACE_AREA>
209.75999999999996

> <JCHEM_REFRACTIVITY>
150.99030000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R)-4-[(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302517
     RDKit          3D
Proanthocyanidins
 71 76  0  0  0  0  0  0  0  0999 V2000
    7.5079    0.6600   -2.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1556    0.9376   -3.0261 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    1.1236   -2.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4445    0.0407   -1.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6872   -1.2499   -2.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4420    0.2655   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1561    1.5146   -0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972    1.7402    0.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338    1.0277    0.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6681   -0.1784    1.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4644   -0.6987    2.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2106   -1.8883    2.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0719   -2.3683    3.7862 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0932   -2.5931    2.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585   -2.1375    1.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810   -2.8486    1.0052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4624   -0.9324    0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182   -0.3598   -0.2706 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7656   -1.3839   -1.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8373   -2.2207   -1.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5053   -2.1026   -1.4758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165   -3.2047   -2.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5503   -3.3014   -3.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8962   -4.2983   -3.9681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4815   -2.4714   -2.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0964   -1.4895   -1.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446   -0.6530   -0.9921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7446   -0.1097    0.2872 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7779    0.8837    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2418    1.8303   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2058    2.7532    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7124    2.7404    1.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6776    3.6627    1.8901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2614    1.8073    2.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3040    0.8943    1.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3991    0.5326    0.2445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5098    1.7271   -0.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6806    0.0480    2.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411    1.4788    2.1874 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9602    1.9900    2.1969 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958    2.5810   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8902    2.3765   -1.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6560    3.4363   -2.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5208   -0.4244   -2.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8805    1.2370   -1.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1433    0.7146   -3.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135   -1.9909   -1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8654   -0.5737   -0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8841    2.8552    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -3.2560    4.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1096   -3.5352    2.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0616   -3.7255    1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518    0.3297   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2200   -2.6796   -1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4360   -3.8157   -3.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181   -5.1973   -3.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -2.6082   -2.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7997   -0.9212    1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588    1.8594   -1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5941    3.5122   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0708    3.6916    2.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6798    1.8231    3.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9764    0.1739    2.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1604    0.8807    1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3296    1.4755   -1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5566   -0.4963    2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    0.0003    3.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    2.1281    2.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3026    2.0832    3.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6859    3.5861   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3857    3.3115   -2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  2  0
 28 36  1  0
 36 37  1  0
 11 38  1  0
 38 39  1  0
 39 40  1  0
  7 41  1  0
 41 42  2  0
 42 43  1  0
 42  3  1  0
 39  8  1  0
 17 10  1  0
 36 18  1  0
 26 19  1  0
 35 29  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  5 47  1  0
  6 48  1  0
  8 49  1  0
 13 50  1  0
 14 51  1  0
 16 52  1  0
 18 53  1  6
 21 54  1  0
 22 55  1  0
 24 56  1  0
 25 57  1  0
 28 58  1  1
 30 59  1  0
 31 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
 36 64  1  1
 37 65  1  0
 38 66  1  0
 38 67  1  0
 39 68  1  1
 40 69  1  0
 41 70  1  0
 43 71  1  0
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.534   0.161   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   44  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       8.002  -1.540   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.335  -1.540   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
CONECT    1   41                                                            
CONECT    2    4   12                                                       
CONECT    3    5   12                                                       
CONECT    4    2   14                                                       
CONECT    5    3   14                                                       
CONECT    6   13   20                                                       
CONECT    7   13   21                                                       
CONECT    8   15   18                                                       
CONECT    9   15   23                                                       
CONECT   10   16   22                                                       
CONECT   11   17   19                                                       
CONECT   12    2    3   29                                                  
CONECT   13    6    7   28                                                  
CONECT   14    4    5   32                                                  
CONECT   15    8    9   33                                                  
CONECT   16   10   17   30                                                  
CONECT   17   11   16   34                                                  
CONECT   18    8   24   35                                                  
CONECT   19   11   25   36                                                  
CONECT   20    6   31   37                                                  
CONECT   21    7   31   38                                                  
CONECT   22   10   28   39   44                                             
CONECT   23    9   24   42                                                  
CONECT   24   18   23   26                                                  
CONECT   25   19   26   30                                                  
CONECT   26   24   25   27   45                                             
CONECT   27   26   29   40   46                                             
CONECT   28   13   22   43   47                                             
CONECT   29   12   27   42   48                                             
CONECT   30   16   25   43                                                  
CONECT   31   20   21   41                                                  
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   20                                                            
CONECT   38   21                                                            
CONECT   39   22                                                            
CONECT   40   27                                                            
CONECT   41    1   31                                                       
CONECT   42   23   29                                                       
CONECT   43   28   30                                                       
CONECT   44   22                                                            
CONECT   45   26                                                            
CONECT   46   27                                                            
CONECT   47   28                                                            
CONECT   48   29                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

COMPND    HMDB0302517
HETATM    1  C1  UNL     1       7.508   0.660  -2.720  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.156   0.938  -3.026  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.174   1.124  -2.100  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.445   0.041  -1.650  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.687  -1.250  -2.120  1.00  0.00           O  
HETATM    6  C4  UNL     1       3.442   0.265  -0.699  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.156   1.515  -0.197  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.097   1.740   0.810  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.934   1.028   0.554  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.668  -0.178   1.174  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.464  -0.699   2.159  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.211  -1.888   2.778  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.072  -2.368   3.786  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.093  -2.593   2.384  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.758  -2.138   1.401  1.00  0.00           C  
HETATM   16  O5  UNL     1      -1.881  -2.849   1.005  1.00  0.00           O  
HETATM   17  C12 UNL     1      -0.462  -0.932   0.804  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.318  -0.360  -0.271  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.766  -1.384  -1.238  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.837  -2.221  -1.808  1.00  0.00           C  
HETATM   21  O6  UNL     1       0.505  -2.103  -1.476  1.00  0.00           O  
HETATM   22  C16 UNL     1      -1.216  -3.205  -2.729  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.550  -3.301  -3.041  1.00  0.00           C  
HETATM   24  O7  UNL     1      -2.896  -4.298  -3.968  1.00  0.00           O  
HETATM   25  C18 UNL     1      -3.481  -2.471  -2.478  1.00  0.00           C  
HETATM   26  C19 UNL     1      -3.096  -1.489  -1.558  1.00  0.00           C  
HETATM   27  O8  UNL     1      -4.045  -0.653  -0.992  1.00  0.00           O  
HETATM   28  C20 UNL     1      -3.745  -0.110   0.287  1.00  0.00           C  
HETATM   29  C21 UNL     1      -4.778   0.884   0.698  1.00  0.00           C  
HETATM   30  C22 UNL     1      -5.242   1.830  -0.192  1.00  0.00           C  
HETATM   31  C23 UNL     1      -6.206   2.753   0.207  1.00  0.00           C  
HETATM   32  C24 UNL     1      -6.712   2.740   1.488  1.00  0.00           C  
HETATM   33  O9  UNL     1      -7.678   3.663   1.890  1.00  0.00           O  
HETATM   34  C25 UNL     1      -6.261   1.807   2.380  1.00  0.00           C  
HETATM   35  C26 UNL     1      -5.304   0.894   1.977  1.00  0.00           C  
HETATM   36  C27 UNL     1      -2.399   0.533   0.244  1.00  0.00           C  
HETATM   37  O10 UNL     1      -2.510   1.727  -0.511  1.00  0.00           O  
HETATM   38  C28 UNL     1       2.681   0.048   2.595  1.00  0.00           C  
HETATM   39  C29 UNL     1       2.641   1.479   2.187  1.00  0.00           C  
HETATM   40  O11 UNL     1       3.960   1.990   2.197  1.00  0.00           O  
HETATM   41  C30 UNL     1       3.896   2.581  -0.661  1.00  0.00           C  
HETATM   42  C31 UNL     1       4.890   2.376  -1.601  1.00  0.00           C  
HETATM   43  O12 UNL     1       5.656   3.436  -2.089  1.00  0.00           O  
HETATM   44  H1  UNL     1       7.521  -0.424  -2.404  1.00  0.00           H  
HETATM   45  H2  UNL     1       7.881   1.237  -1.863  1.00  0.00           H  
HETATM   46  H3  UNL     1       8.143   0.715  -3.626  1.00  0.00           H  
HETATM   47  H4  UNL     1       4.113  -1.991  -1.745  1.00  0.00           H  
HETATM   48  H5  UNL     1       2.865  -0.574  -0.342  1.00  0.00           H  
HETATM   49  H6  UNL     1       1.884   2.855   0.787  1.00  0.00           H  
HETATM   50  H7  UNL     1       1.824  -3.256   4.203  1.00  0.00           H  
HETATM   51  H8  UNL     1      -0.110  -3.535   2.873  1.00  0.00           H  
HETATM   52  H9  UNL     1      -2.062  -3.726   1.467  1.00  0.00           H  
HETATM   53  H10 UNL     1      -0.652   0.330  -0.891  1.00  0.00           H  
HETATM   54  H11 UNL     1       1.220  -2.680  -1.856  1.00  0.00           H  
HETATM   55  H12 UNL     1      -0.436  -3.816  -3.128  1.00  0.00           H  
HETATM   56  H13 UNL     1      -3.118  -5.197  -3.549  1.00  0.00           H  
HETATM   57  H14 UNL     1      -4.511  -2.608  -2.773  1.00  0.00           H  
HETATM   58  H15 UNL     1      -3.800  -0.921   1.016  1.00  0.00           H  
HETATM   59  H16 UNL     1      -4.859   1.859  -1.203  1.00  0.00           H  
HETATM   60  H17 UNL     1      -6.594   3.512  -0.465  1.00  0.00           H  
HETATM   61  H18 UNL     1      -8.071   3.692   2.802  1.00  0.00           H  
HETATM   62  H19 UNL     1      -6.680   1.823   3.383  1.00  0.00           H  
HETATM   63  H20 UNL     1      -4.976   0.174   2.717  1.00  0.00           H  
HETATM   64  H21 UNL     1      -2.160   0.881   1.273  1.00  0.00           H  
HETATM   65  H22 UNL     1      -2.330   1.475  -1.466  1.00  0.00           H  
HETATM   66  H23 UNL     1       3.557  -0.496   2.219  1.00  0.00           H  
HETATM   67  H24 UNL     1       2.690   0.000   3.704  1.00  0.00           H  
HETATM   68  H25 UNL     1       2.093   2.128   2.908  1.00  0.00           H  
HETATM   69  H26 UNL     1       4.303   2.083   3.128  1.00  0.00           H  
HETATM   70  H27 UNL     1       3.686   3.586  -0.275  1.00  0.00           H  
HETATM   71  H28 UNL     1       6.386   3.311  -2.775  1.00  0.00           H  
CONECT    1    2   44   45   46
CONECT    2    3
CONECT    3    4    4   42
CONECT    4    5    6
CONECT    5   47
CONECT    6    7    7   48
CONECT    7    8   41
CONECT    8    9   39   49
CONECT    9   10
CONECT   10   11   11   17
CONECT   11   12   38
CONECT   12   13   14   14
CONECT   13   50
CONECT   14   15   51
CONECT   15   16   17   17
CONECT   16   52
CONECT   17   18
CONECT   18   19   36   53
CONECT   19   20   20   26
CONECT   20   21   22
CONECT   21   54
CONECT   22   23   23   55
CONECT   23   24   25
CONECT   24   56
CONECT   25   26   26   57
CONECT   26   27
CONECT   27   28
CONECT   28   29   36   58
CONECT   29   30   30   35
CONECT   30   31   59
CONECT   31   32   32   60
CONECT   32   33   34
CONECT   33   61
CONECT   34   35   35   62
CONECT   35   63
CONECT   36   37   64
CONECT   37   65
CONECT   38   39   66   67
CONECT   39   40   68
CONECT   40   69
CONECT   41   42   42   70
CONECT   42   43
CONECT   43   71
END

HMDB0302517
     RDKit          3D
Proanthocyanidins
 71 76  0  0  0  0  0  0  0  0999 V2000
    7.5079    0.6600   -2.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1556    0.9376   -3.0261 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    1.1236   -2.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4445    0.0407   -1.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6872   -1.2499   -2.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4420    0.2655   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1561    1.5146   -0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972    1.7402    0.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338    1.0277    0.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6681   -0.1784    1.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4644   -0.6987    2.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2106   -1.8883    2.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0719   -2.3683    3.7862 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0932   -2.5931    2.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585   -2.1375    1.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810   -2.8486    1.0052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4624   -0.9324    0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182   -0.3598   -0.2706 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7656   -1.3839   -1.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8373   -2.2207   -1.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5053   -2.1026   -1.4758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165   -3.2047   -2.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5503   -3.3014   -3.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8962   -4.2983   -3.9681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4815   -2.4714   -2.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0964   -1.4895   -1.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0446   -0.6530   -0.9921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7446   -0.1097    0.2872 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7779    0.8837    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2418    1.8303   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2058    2.7532    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7124    2.7404    1.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6776    3.6627    1.8901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2614    1.8073    2.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3040    0.8943    1.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3991    0.5326    0.2445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5098    1.7271   -0.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6806    0.0480    2.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411    1.4788    2.1874 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9602    1.9900    2.1969 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958    2.5810   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8902    2.3765   -1.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6560    3.4363   -2.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5208   -0.4244   -2.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8805    1.2370   -1.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1433    0.7146   -3.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135   -1.9909   -1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8654   -0.5737   -0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8841    2.8552    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -3.2560    4.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1096   -3.5352    2.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0616   -3.7255    1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518    0.3297   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2200   -2.6796   -1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4360   -3.8157   -3.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181   -5.1973   -3.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -2.6082   -2.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7997   -0.9212    1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588    1.8594   -1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5941    3.5122   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0708    3.6916    2.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6798    1.8231    3.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9764    0.1739    2.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1604    0.8807    1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3296    1.4755   -1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5566   -0.4963    2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    0.0003    3.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    2.1281    2.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3026    2.0832    3.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6859    3.5861   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3857    3.3115   -2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  2  0
 28 36  1  0
 36 37  1  0
 11 38  1  0
 38 39  1  0
 39 40  1  0
  7 41  1  0
 41 42  2  0
 42 43  1  0
 42  3  1  0
 39  8  1  0
 17 10  1  0
 36 18  1  0
 26 19  1  0
 35 29  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  5 47  1  0
  6 48  1  0
  8 49  1  0
 13 50  1  0
 14 51  1  0
 16 52  1  0
 18 53  1  6
 21 54  1  0
 22 55  1  0
 24 56  1  0
 25 57  1  0
 28 58  1  1
 30 59  1  0
 31 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
 36 64  1  1
 37 65  1  0
 38 66  1  0
 38 67  1  0
 39 68  1  1
 40 69  1  0
 41 70  1  0
 43 71  1  0
M  END

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Synonyms

Value	Source
Zangrado	MeSH
Polyhydroxyflavan-3-ol	MeSH
Proanthocyanidins	MeSH
Polymers, anthocyanidin	MeSH
Procyanidins	MeSH
Anthocyanidin polymers	MeSH
Condensed tannin	MeSH
Condensed tannins	MeSH
Tannin, condensed	MeSH
Tannins, condensed	MeSH
Proanthocyanidin	MeSH

Chemical Formula

C₃₁H₂₈O₁₂

Average Molecular Weight

592.553

Monoisotopic Molecular Weight

592.158076342

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)CC2=C(OC1([H])C1=CC(O)=C(OC)C(O)=C1)C(=C(O)C=C2O)[C@@]1([H])C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC=C(O)C=C2)[C@]1([H])O

InChI Identifier

InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1

InChI Key

JPFCOVZKLAXXOE-XBNSMERZSA-N

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
Epigallocatechin
Catechin
4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Chromane
Benzopyran
1-benzopyran
Methoxyphenol
Resorcinol
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302517)

Food

Fruit

Drupe

Apricot (FooDB: FOOD00144)

Tropical fruit

Cherimoya (FooDB: FOOD00326)

Vegetable

Fruit vegetable

Avocado (FooDB: FOOD00130)

Cereal and cereal product

Cereal

Common buckwheat (FooDB: FOOD00079)

Herb and spice

Spice

Herb

Sweet bay (FooDB: FOOD00097)
Roselle (FooDB: FOOD00447)

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Synthetic

Personal care products

Deodorant (HMDB: HMDB0302517)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0302517)
Antioxidant (HMDB: HMDB0302517)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0302517)

Antimicrobial agent

Gram(+)icide (HMDB: HMDB0302517)

Hepatoprotective (HMDB: HMDB0302517)

Antielastase (HMDB: HMDB0302517)
Beta-glucuronidase inhibitor (HMDB: HMDB0302517)
Collagenase inhibitor (HMDB: HMDB0302517)
Hyaluronidase inhibitor (HMDB: HMDB0302517)
Ornithine-decarboxylase inhibitor (HMDB: HMDB0302517)

Anti alopecic (HMDB: HMDB0302517)
Anti atherosclerotic (HMDB: HMDB0302517)
Anti bacterial (HMDB: HMDB0302517)
Anti CVI (HMDB: HMDB0302517)
Anti diabetic (HMDB: HMDB0302517)
Anti edemic (HMDB: HMDB0302517)
Anti histaminic (HMDB: HMDB0302517)
Anti ischemic (HMDB: HMDB0302517)
Anti periodontal (HMDB: HMDB0302517)
Anti plaque (HMDB: HMDB0302517)
Anti proliferant (HMDB: HMDB0302517)
Anti retinopathic (HMDB: HMDB0302517)
Anti septic (HMDB: HMDB0302517)
Anti stroke (HMDB: HMDB0302517)
Capillariprotective (HMDB: HMDB0302517)
Cardioprotective (HMDB: HMDB0302517)
Collagenic (HMDB: HMDB0302517)
Propecic (HMDB: HMDB0302517)
Vasorelaxant (HMDB: HMDB0302517)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.42	ALOGPS
logP	3.26	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.86	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	209.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	150.99 m³·mol⁻¹	ChemAxon
Polarizability	58.52 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	240.039	32859911
AllCCS	[M+H-H2O]+	238.539	32859911
AllCCS	[M+Na]+	241.783	32859911
AllCCS	[M+NH4]+	241.398	32859911
AllCCS	[M-H]-	234.768	32859911
AllCCS	[M+Na-2H]-	236.709	32859911
AllCCS	[M+HCOO]-	238.994	32859911
DeepCCS	[M+H]+	221.931	30932474
DeepCCS	[M-H]-	220.095	30932474
DeepCCS	[M-2H]-	253.786	30932474
DeepCCS	[M+Na]+	227.603	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Proanthocyanidins,2TMS,isomer #16	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	5441.5	Semi standard non polar	33892256
Proanthocyanidins,2TMS,isomer #16	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	4695.2	Standard non polar	33892256
Proanthocyanidins,2TMS,isomer #16	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	7504.8	Standard polar	33892256
Proanthocyanidins,3TMS,isomer #13	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	5264.1	Semi standard non polar	33892256
Proanthocyanidins,3TMS,isomer #13	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	4541.4	Standard non polar	33892256
Proanthocyanidins,3TMS,isomer #13	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	6949.2	Standard polar	33892256
Proanthocyanidins,3TMS,isomer #34	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	5249.9	Semi standard non polar	33892256
Proanthocyanidins,3TMS,isomer #34	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	4565.2	Standard non polar	33892256
Proanthocyanidins,3TMS,isomer #34	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	6893.0	Standard polar	33892256
Proanthocyanidins,3TMS,isomer #44	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	5208.7	Semi standard non polar	33892256
Proanthocyanidins,3TMS,isomer #44	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	4527.3	Standard non polar	33892256
Proanthocyanidins,3TMS,isomer #44	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	6845.4	Standard polar	33892256
Proanthocyanidins,3TMS,isomer #48	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	5205.5	Semi standard non polar	33892256
Proanthocyanidins,3TMS,isomer #48	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	4549.9	Standard non polar	33892256
Proanthocyanidins,3TMS,isomer #48	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	6841.8	Standard polar	33892256
Proanthocyanidins,3TMS,isomer #49	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	5238.7	Semi standard non polar	33892256
Proanthocyanidins,3TMS,isomer #49	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	4595.9	Standard non polar	33892256
Proanthocyanidins,3TMS,isomer #49	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	6723.6	Standard polar	33892256
Proanthocyanidins,3TMS,isomer #50	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	5229.2	Semi standard non polar	33892256
Proanthocyanidins,3TMS,isomer #50	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	4608.6	Standard non polar	33892256
Proanthocyanidins,3TMS,isomer #50	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	6905.6	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #12	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	5131.4	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #12	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	4456.7	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #12	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	6520.4	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #22	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	5067.5	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #22	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	4409.9	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #22	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	6462.3	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #32	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	5064.8	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #32	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	4439.6	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #32	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	6482.0	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #33	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	5077.4	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #33	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	4482.5	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #33	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	6408.5	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #34	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	5082.3	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #34	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	4514.9	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #34	COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	6526.5	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #47	COC1=C(O[Si](C)(C)C)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	5152.2	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #47	COC1=C(O[Si](C)(C)C)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	4437.6	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #47	COC1=C(O[Si](C)(C)C)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	6456.6	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #57	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	5062.0	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #57	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	4426.6	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #57	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	6445.0	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #67	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	5069.7	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #67	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	4453.2	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #67	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	6447.7	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #68	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	5102.7	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #68	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	4493.3	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #68	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C	6376.2	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #69	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C	5090.6	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #69	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C	4511.2	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #69	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C	6492.8	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #77	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	5012.2	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #77	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	4410.3	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #77	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	6406.5	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #78	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	5027.6	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #78	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	4453.3	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #78	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	6341.6	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #79	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	5009.2	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #79	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	4463.3	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #79	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	6451.8	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #83	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	5036.6	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #83	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	4473.5	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #83	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O	6351.8	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #84	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	5020.3	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #84	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	4495.3	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #84	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	6455.8	Standard polar	33892256
Proanthocyanidins,4TMS,isomer #85	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	5035.1	Semi standard non polar	33892256
Proanthocyanidins,4TMS,isomer #85	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	4535.1	Standard non polar	33892256
Proanthocyanidins,4TMS,isomer #85	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O	6381.8	Standard polar	33892256
Proanthocyanidins,2TBDMS,isomer #16	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	5904.0	Semi standard non polar	33892256
Proanthocyanidins,2TBDMS,isomer #16	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	4974.7	Standard non polar	33892256
Proanthocyanidins,2TBDMS,isomer #16	COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O	7221.3	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 10V, Negative-QTOF	splash10-0006-0101190000-b31c9c0fca7d80ef20c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 20V, Negative-QTOF	splash10-00e9-0914230000-a4c705979f1d6fc67fa9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 40V, Negative-QTOF	splash10-004i-1910000000-b98ec34dc51f84414709	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 10V, Negative-QTOF	splash10-0006-0000090000-dfcbeb46abd0824fb3bc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 20V, Negative-QTOF	splash10-00dl-0130390000-4369984b9fad807701a3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 40V, Negative-QTOF	splash10-00c9-1916640000-0346683242ed543fd142	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 10V, Positive-QTOF	splash10-0006-0114590000-7fd73466ae61d7b32ff8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 20V, Positive-QTOF	splash10-0a4i-0446920000-e90bb0a2e1c1e3714cb4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 40V, Positive-QTOF	splash10-0abc-0591110000-df08b8a7f2f9b441aeaf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 10V, Positive-QTOF	splash10-0006-0010190000-1a235a0283d9b9f0a78e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 20V, Positive-QTOF	splash10-0a4i-0214940000-42cf8f12882748e6f4f9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proanthocyanidins 40V, Positive-QTOF	splash10-0ktf-0901480000-9a31aa132b216973a0a5	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004901

KNApSAcK ID

C00002934

Chemspider ID

97167

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108065

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Proanthocyanidins (HMDB0302517)

MOL for HMDB0302517 (Proanthocyanidins)

3D MOL for HMDB0302517 (Proanthocyanidins)

3D SDF for HMDB0302517 (Proanthocyanidins)

3D-SDF for HMDB0302517 (Proanthocyanidins)

PDB for HMDB0302517 (Proanthocyanidins)

3D PDB for HMDB0302517 (Proanthocyanidins)

SMILES for HMDB0302517 (Proanthocyanidins)

INCHI for HMDB0302517 (Proanthocyanidins)

Structure for HMDB0302517 (Proanthocyanidins)

3D Structure for HMDB0302517 (Proanthocyanidins)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra