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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:42:35 UTC

Update Date

2022-03-07 02:56:09 UTC

HMDB ID

HMDB0039299

Secondary Accession Numbers

HMDB39299

Metabolite Identification

Common Name

3,3'-Di-O-galloylprocyanidin B5

Description

3,3'-Di-O-galloylprocyanidin 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''. 3,3'-Di-O-galloylprocyanidin B5 has been detected, but not quantified in, several different foods, such as red tea, black tea, herbal tea, green tea, and green vegetables. This could make 3,3'-di-O-galloylprocyanidin B5 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,3'-Di-O-galloylprocyanidin B5.

Structure

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


  Mrv0541 02241217352D          

 64 71  0  0  0  0            999 V2000
   -2.0496    2.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641    3.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4786    3.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1930    3.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9075    3.8356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4786    2.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3351    2.5981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3351    3.4231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0496    3.8356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    5.8981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2888    3.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7165    4.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 53  1  0  0  0  0
  7 53  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  6  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
  7 19  1  0  0  0  0
  8 20  1  6  0  0  0
 30 20  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
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 21 26  1  0  0  0  0
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 57 62  1  0  0  0  0
 55 63  1  0  0  0  0
 63 64  2  0  0  0  0
M  END

HMDB0039299
     RDKit          3D
3,3'-Di-O-galloylprocyanidin B5
 98105  0  0  0  0  0  0  0  0999 V2000
    4.5077   -0.3818   -3.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6900   -0.0703   -2.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6783   -0.4160   -1.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4815   -1.0922   -1.7463 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2785   -0.2416   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937   -0.5506   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4483   -1.7579    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3797   -2.0526    1.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683   -1.0844    1.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031   -1.3954    2.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3654    0.1635    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622    1.1194    1.5290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7986    2.3061    2.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792    2.3697    2.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3251    1.2699    2.3635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0356    3.4968    3.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8655    4.6024    3.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4026    5.6921    4.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033    4.5181    3.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341    3.3751    2.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2625    2.0315    2.8602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1540    1.3306    3.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3486    1.5696    0.5095 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.6604    0.8289   -1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550    1.8909   -2.1906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1087   -0.1628   -2.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6782   -1.3347   -2.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241217352D          

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M  END
> <DATABASE_ID>
HMDB0039299

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C44H34O20/c45-19-11-25(50)34-32(12-19)62-41(16-2-4-22(47)24(49)6-16)42(64-44(60)18-9-29(54)39(58)30(55)10-18)36(34)35-26(51)14-31-20(37(35)56)13-33(40(61-31)15-1-3-21(46)23(48)5-15)63-43(59)17-7-27(52)38(57)28(53)8-17/h1-12,14,33,36,40-42,45-58H,13H2/t33-,36-,40-,41-,42-/m1/s1

> <INCHI_KEY>
LFBGVECYPPCVDS-QNPRKUGLSA-N

> <FORMULA>
C44H34O20

> <MOLECULAR_WEIGHT>
882.7288

> <EXACT_MASS>
882.164343528

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
82.70938209757075

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
6.284952780999999

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.306770124709642

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.765192316743891

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4873751499504

> <JCHEM_POLAR_SURFACE_AREA>
354.28000000000003

> <JCHEM_REFRACTIVITY>
218.0374

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039299
     RDKit          3D
3,3'-Di-O-galloylprocyanidin B5
 98105  0  0  0  0  0  0  0  0999 V2000
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    1.2785   -0.2416   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937   -0.5506   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4134   -0.9184   -4.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2901   -0.7306   -6.3576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9887    0.0190   -4.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5041    0.4011   -0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5512    1.6137   -0.6484 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6726   -2.7280   -0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8385   -2.2990    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9799   -2.5739    1.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0020   -3.3147    1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1738   -3.6272    1.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8515   -3.7532   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8734   -4.4984   -0.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7126   -3.4672   -0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9032    0.6125   -1.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1748    0.9884   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3537    1.6365   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6535    2.0325    1.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3094    1.9364   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4829    2.5907   -0.8259 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0377    1.5583   -2.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9928    1.8598   -3.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8499    0.9096   -2.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085   -1.2354   -2.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6760   -0.1444   -2.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6579    0.8093   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3185   -3.0167    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834   -2.2877    3.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9635    0.6103    2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3120    1.2780    2.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916    3.5850    3.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2870    6.4960    4.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8607    5.3568    3.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1201    2.7444    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2741    3.1130    2.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8548    1.8336    4.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1685   -1.7321    4.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7593   -2.5531    2.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7893   -0.5214    1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842    2.4118   -0.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8007   -1.5367   -1.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7884   -3.6318   -1.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8266   -3.8895   -5.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6058   -1.4262   -7.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5386    0.9431   -4.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137    1.9522   -1.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077   -3.2571   -1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0507   -1.7166    1.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1082   -2.2403    2.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2399   -3.2813    2.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7791   -4.8261   -1.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6735   -3.8505   -1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405    0.7616    0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375    1.8678    1.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1457    2.7856   -1.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9390    1.6527   -4.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6995    0.6391   -3.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
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M  END

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  C   UNK     0      -3.826   4.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.160   4.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.160   6.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.493   7.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.827   6.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -9.161   7.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.493   4.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.492   4.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.492   6.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.826   7.160   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.175  11.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.175   9.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.159   8.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.159   7.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.175   6.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.509   7.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.509   8.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.842   9.470   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.493   2.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.159   4.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.509   2.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.175   1.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.175   0.230   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.509  -0.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.842   0.230   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.842   1.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.176   2.540   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.176  -0.540   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.509  -2.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.159   2.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.492   1.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -10.671   3.495   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.671   1.955   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -12.004   1.185   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -12.004  -0.355   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.671  -1.125   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -10.671  -2.665   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -9.337   1.185   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.337  -0.355   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -12.004   4.265   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -13.338   3.495   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0     -13.338   1.955   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -18.673   3.495   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0     -17.339   4.265   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -16.006   3.495   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -14.672   4.265   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -14.672   5.805   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -16.006   6.575   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -17.339   5.805   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0     -18.673   6.575   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -8.003   1.955   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0     -12.004   5.805   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -7.827   4.850   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -14.672   7.345   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -13.338   8.115   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -13.338   9.655   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -14.672  10.425   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -16.005   9.655   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -16.005   8.115   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0     -17.339   7.345   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0     -17.339  10.425   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0     -14.672  11.965   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0     -12.004   7.345   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0     -10.671   8.115   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   53                                                  
CONECT    6    5                                                            
CONECT    7    2   53   19                                                  
CONECT    8    1    9   20                                                  
CONECT    9    8   10   14                                                  
CONECT   10    3    9                                                       
CONECT   11   12                                                            
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14    9   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   18                                                  
CONECT   18   17                                                            
CONECT   19    7                                                            
CONECT   20    8   30                                                       
CONECT   21   22   26                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   24                                                            
CONECT   30   20   22   31                                                  
CONECT   31   30                                                            
CONECT   32   33   40   53                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35   42                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   39                                                  
CONECT   37   36                                                            
CONECT   38   33   39   51                                                  
CONECT   39   36   38                                                       
CONECT   40   32   41   52                                                  
CONECT   41   40   42   46                                                  
CONECT   42   34   41                                                       
CONECT   43   44                                                            
CONECT   44   43   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   41   45   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   44   48   50                                                  
CONECT   50   49                                                            
CONECT   51   38                                                            
CONECT   52   40   63                                                       
CONECT   53    5    7   32                                                  
CONECT   54   55   59                                                       
CONECT   55   54   56   63                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   62                                                  
CONECT   58   57   59   61                                                  
CONECT   59   58   54   60                                                  
CONECT   60   59                                                            
CONECT   61   58                                                            
CONECT   62   57                                                            
CONECT   63   52   55   64                                                  
CONECT   64   63                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  142    0
END

COMPND    HMDB0039299
HETATM    1  O1  UNL     1       4.508  -0.382  -3.405  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.690  -0.070  -2.202  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.678  -0.416  -1.320  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.481  -1.092  -1.746  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.278  -0.242  -1.585  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.394  -0.551  -0.461  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.448  -1.758   0.150  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.380  -2.053   1.198  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.268  -1.084   1.609  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.103  -1.395   2.674  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.365   0.164   1.020  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.362   1.119   1.529  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.799   2.306   2.211  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.479   2.370   2.612  1.00  0.00           C  
HETATM   15  O4  UNL     1       0.325   1.270   2.364  1.00  0.00           O  
HETATM   16  C12 UNL     1      -0.036   3.497   3.228  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.865   4.602   3.475  1.00  0.00           C  
HETATM   18  O5  UNL     1      -0.403   5.692   4.080  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.203   4.518   3.061  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.634   3.375   2.442  1.00  0.00           C  
HETATM   21  O6  UNL     1      -3.971   3.266   2.021  1.00  0.00           O  
HETATM   22  C16 UNL     1      -4.494   2.244   1.236  1.00  0.00           C  
HETATM   23  C17 UNL     1      -5.371   1.378   1.997  1.00  0.00           C  
HETATM   24  C18 UNL     1      -6.263   2.032   2.860  1.00  0.00           C  
HETATM   25  C19 UNL     1      -7.154   1.331   3.639  1.00  0.00           C  
HETATM   26  C20 UNL     1      -7.210  -0.042   3.605  1.00  0.00           C  
HETATM   27  O7  UNL     1      -8.117  -0.724   4.400  1.00  0.00           O  
HETATM   28  C21 UNL     1      -6.334  -0.685   2.758  1.00  0.00           C  
HETATM   29  O8  UNL     1      -6.401  -2.073   2.734  1.00  0.00           O  
HETATM   30  C22 UNL     1      -5.436   0.026   1.974  1.00  0.00           C  
HETATM   31  C23 UNL     1      -3.349   1.570   0.510  1.00  0.00           C  
HETATM   32  O9  UNL     1      -3.782   0.620  -0.404  1.00  0.00           O  
HETATM   33  C24 UNL     1      -3.660   0.829  -1.755  1.00  0.00           C  
HETATM   34  O10 UNL     1      -3.155   1.891  -2.191  1.00  0.00           O  
HETATM   35  C25 UNL     1      -4.109  -0.163  -2.719  1.00  0.00           C  
HETATM   36  C26 UNL     1      -4.678  -1.335  -2.273  1.00  0.00           C  
HETATM   37  C27 UNL     1      -5.108  -2.283  -3.182  1.00  0.00           C  
HETATM   38  O11 UNL     1      -5.671  -3.439  -2.709  1.00  0.00           O  
HETATM   39  C28 UNL     1      -4.984  -2.092  -4.536  1.00  0.00           C  
HETATM   40  O12 UNL     1      -5.410  -3.034  -5.462  1.00  0.00           O  
HETATM   41  C29 UNL     1      -4.413  -0.918  -4.980  1.00  0.00           C  
HETATM   42  O13 UNL     1      -4.290  -0.731  -6.358  1.00  0.00           O  
HETATM   43  C30 UNL     1      -3.989   0.019  -4.079  1.00  0.00           C  
HETATM   44  C31 UNL     1      -0.504   0.401  -0.030  1.00  0.00           C  
HETATM   45  O14 UNL     1      -0.551   1.614  -0.648  1.00  0.00           O  
HETATM   46  O15 UNL     1       1.353  -2.688  -0.299  1.00  0.00           O  
HETATM   47  C32 UNL     1       2.455  -2.439  -1.133  1.00  0.00           C  
HETATM   48  C33 UNL     1       3.673  -2.728  -0.328  1.00  0.00           C  
HETATM   49  C34 UNL     1       3.838  -2.299   0.969  1.00  0.00           C  
HETATM   50  C35 UNL     1       4.980  -2.574   1.721  1.00  0.00           C  
HETATM   51  C36 UNL     1       6.002  -3.315   1.141  1.00  0.00           C  
HETATM   52  O16 UNL     1       7.174  -3.627   1.838  1.00  0.00           O  
HETATM   53  C37 UNL     1       5.852  -3.753  -0.161  1.00  0.00           C  
HETATM   54  O17 UNL     1       6.873  -4.498  -0.752  1.00  0.00           O  
HETATM   55  C38 UNL     1       4.713  -3.467  -0.881  1.00  0.00           C  
HETATM   56  C39 UNL     1       5.903   0.613  -1.800  1.00  0.00           C  
HETATM   57  C40 UNL     1       6.175   0.988  -0.512  1.00  0.00           C  
HETATM   58  C41 UNL     1       7.354   1.636  -0.210  1.00  0.00           C  
HETATM   59  O18 UNL     1       7.654   2.032   1.106  1.00  0.00           O  
HETATM   60  C42 UNL     1       8.309   1.936  -1.176  1.00  0.00           C  
HETATM   61  O19 UNL     1       9.483   2.591  -0.826  1.00  0.00           O  
HETATM   62  C43 UNL     1       8.038   1.558  -2.474  1.00  0.00           C  
HETATM   63  O20 UNL     1       8.993   1.860  -3.431  1.00  0.00           O  
HETATM   64  C44 UNL     1       6.850   0.910  -2.756  1.00  0.00           C  
HETATM   65  H1  UNL     1       2.608  -1.235  -2.864  1.00  0.00           H  
HETATM   66  H2  UNL     1       0.676  -0.144  -2.539  1.00  0.00           H  
HETATM   67  H3  UNL     1       1.658   0.809  -1.407  1.00  0.00           H  
HETATM   68  H4  UNL     1      -0.319  -3.017   1.668  1.00  0.00           H  
HETATM   69  H5  UNL     1      -2.083  -2.288   3.149  1.00  0.00           H  
HETATM   70  H6  UNL     1      -2.963   0.610   2.343  1.00  0.00           H  
HETATM   71  H7  UNL     1       1.312   1.278   2.648  1.00  0.00           H  
HETATM   72  H8  UNL     1       0.992   3.585   3.557  1.00  0.00           H  
HETATM   73  H9  UNL     1      -0.287   6.496   4.461  1.00  0.00           H  
HETATM   74  H10 UNL     1      -2.861   5.357   3.240  1.00  0.00           H  
HETATM   75  H11 UNL     1      -5.120   2.744   0.439  1.00  0.00           H  
HETATM   76  H12 UNL     1      -6.274   3.113   2.939  1.00  0.00           H  
HETATM   77  H13 UNL     1      -7.855   1.834   4.316  1.00  0.00           H  
HETATM   78  H14 UNL     1      -8.168  -1.732   4.386  1.00  0.00           H  
HETATM   79  H15 UNL     1      -5.759  -2.553   2.113  1.00  0.00           H  
HETATM   80  H16 UNL     1      -4.789  -0.521   1.339  1.00  0.00           H  
HETATM   81  H17 UNL     1      -2.884   2.412  -0.064  1.00  0.00           H  
HETATM   82  H18 UNL     1      -4.801  -1.537  -1.213  1.00  0.00           H  
HETATM   83  H19 UNL     1      -5.788  -3.632  -1.718  1.00  0.00           H  
HETATM   84  H20 UNL     1      -5.827  -3.889  -5.120  1.00  0.00           H  
HETATM   85  H21 UNL     1      -4.606  -1.426  -7.020  1.00  0.00           H  
HETATM   86  H22 UNL     1      -3.539   0.943  -4.434  1.00  0.00           H  
HETATM   87  H23 UNL     1      -0.014   1.952  -1.410  1.00  0.00           H  
HETATM   88  H24 UNL     1       2.408  -3.257  -1.914  1.00  0.00           H  
HETATM   89  H25 UNL     1       3.051  -1.717   1.444  1.00  0.00           H  
HETATM   90  H26 UNL     1       5.108  -2.240   2.728  1.00  0.00           H  
HETATM   91  H27 UNL     1       7.240  -3.281   2.798  1.00  0.00           H  
HETATM   92  H28 UNL     1       6.779  -4.826  -1.701  1.00  0.00           H  
HETATM   93  H29 UNL     1       4.674  -3.851  -1.901  1.00  0.00           H  
HETATM   94  H30 UNL     1       5.440   0.762   0.248  1.00  0.00           H  
HETATM   95  H31 UNL     1       7.038   1.868   1.881  1.00  0.00           H  
HETATM   96  H32 UNL     1      10.146   2.786  -1.568  1.00  0.00           H  
HETATM   97  H33 UNL     1       8.939   1.653  -4.401  1.00  0.00           H  
HETATM   98  H34 UNL     1       6.699   0.639  -3.804  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   56
CONECT    3    4
CONECT    4    5   47   65
CONECT    5    6   66   67
CONECT    6    7    7   44
CONECT    7    8   46
CONECT    8    9    9   68
CONECT    9   10   11
CONECT   10   69
CONECT   11   12   44   44
CONECT   12   13   31   70
CONECT   13   14   14   20
CONECT   14   15   16
CONECT   15   71
CONECT   16   17   17   72
CONECT   17   18   19
CONECT   18   73
CONECT   19   20   20   74
CONECT   20   21
CONECT   21   22
CONECT   22   23   31   75
CONECT   23   24   24   30
CONECT   24   25   76
CONECT   25   26   26   77
CONECT   26   27   28
CONECT   27   78
CONECT   28   29   30   30
CONECT   29   79
CONECT   30   80
CONECT   31   32   81
CONECT   32   33
CONECT   33   34   34   35
CONECT   35   36   36   43
CONECT   36   37   82
CONECT   37   38   39   39
CONECT   38   83
CONECT   39   40   41
CONECT   40   84
CONECT   41   42   43   43
CONECT   42   85
CONECT   43   86
CONECT   44   45
CONECT   45   87
CONECT   46   47
CONECT   47   48   88
CONECT   48   49   49   55
CONECT   49   50   89
CONECT   50   51   51   90
CONECT   51   52   53
CONECT   52   91
CONECT   53   54   55   55
CONECT   54   92
CONECT   55   93
CONECT   56   57   57   64
CONECT   57   58   94
CONECT   58   59   60   60
CONECT   59   95
CONECT   60   61   62
CONECT   61   96
CONECT   62   63   64   64
CONECT   63   97
CONECT   64   98
END

HMDB0039299
     RDKit          3D
3,3'-Di-O-galloylprocyanidin B5
 98105  0  0  0  0  0  0  0  0999 V2000
    4.5077   -0.3818   -3.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6900   -0.0703   -2.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6783   -0.4160   -1.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4815   -1.0922   -1.7463 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2785   -0.2416   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937   -0.5506   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4483   -1.7579    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3797   -2.0526    1.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683   -1.0844    1.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031   -1.3954    2.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3654    0.1635    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622    1.1194    1.5290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7986    2.3061    2.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792    2.3697    2.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3251    1.2699    2.3635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0356    3.4968    3.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8655    4.6024    3.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4026    5.6921    4.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033    4.5181    3.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341    3.3751    2.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9706    3.2659    2.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4941    2.2442    1.2364 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3711    1.3780    1.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2625    2.0315    2.8602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1540    1.3306    3.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2097   -0.0417    3.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1175   -0.7240    4.4003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3340   -0.6852    2.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4014   -2.0726    2.7344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4365    0.0257    1.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486    1.5696    0.5095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7821    0.6200   -0.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604    0.8289   -1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550    1.8909   -2.1906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1087   -0.1628   -2.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6782   -1.3347   -2.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1084   -2.2835   -3.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6710   -3.4394   -2.7089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9839   -2.0919   -4.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4103   -3.0337   -5.4618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134   -0.9184   -4.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2901   -0.7306   -6.3576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9887    0.0190   -4.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5041    0.4011   -0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5512    1.6137   -0.6484 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3526   -2.6883   -0.2990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552   -2.4395   -1.1331 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6726   -2.7280   -0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8385   -2.2990    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9799   -2.5739    1.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0020   -3.3147    1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1738   -3.6272    1.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8515   -3.7532   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8734   -4.4984   -0.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7126   -3.4672   -0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9032    0.6125   -1.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1748    0.9884   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3537    1.6365   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6535    2.0325    1.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3094    1.9364   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4829    2.5907   -0.8259 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0377    1.5583   -2.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9928    1.8598   -3.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8499    0.9096   -2.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085   -1.2354   -2.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6760   -0.1444   -2.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6579    0.8093   -1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3185   -3.0167    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834   -2.2877    3.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9635    0.6103    2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3120    1.2780    2.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916    3.5850    3.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2870    6.4960    4.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8607    5.3568    3.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1201    2.7444    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2741    3.1130    2.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8548    1.8336    4.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1685   -1.7321    4.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7593   -2.5531    2.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7893   -0.5214    1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842    2.4118   -0.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8007   -1.5367   -1.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7884   -3.6318   -1.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8266   -3.8895   -5.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6058   -1.4262   -7.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5386    0.9431   -4.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137    1.9522   -1.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077   -3.2571   -1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0507   -1.7166    1.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1082   -2.2403    2.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2399   -3.2813    2.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7791   -4.8261   -1.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6735   -3.8505   -1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405    0.7616    0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375    1.8678    1.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1457    2.7856   -1.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9390    1.6527   -4.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6995    0.6391   -3.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
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 24 25  1  0
 25 26  2  0
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 28 29  1  0
 28 30  2  0
 22 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
 39 40  1  0
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 41 43  2  0
 11 44  2  0
 44 45  1  0
  7 46  1  0
 46 47  1  0
 47 48  1  0
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 49 50  1  0
 50 51  2  0
 51 52  1  0
 51 53  1  0
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  2 56  1  0
 56 57  2  0
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 44  6  1  0
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 20 13  1  0
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  4 65  1  6
  5 66  1  0
  5 67  1  0
  8 68  1  0
 10 69  1  0
 12 70  1  1
 15 71  1  0
 16 72  1  0
 18 73  1  0
 19 74  1  0
 22 75  1  6
 24 76  1  0
 25 77  1  0
 27 78  1  0
 29 79  1  0
 30 80  1  0
 31 81  1  6
 36 82  1  0
 38 83  1  0
 40 84  1  0
 42 85  1  0
 43 86  1  0
 45 87  1  0
 47 88  1  6
 49 89  1  0
 50 90  1  0
 52 91  1  0
 54 92  1  0
 55 93  1  0
 57 94  1  0
 59 95  1  0
 61 96  1  0
 63 97  1  0
 64 98  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-O-Galloylepicatechin-(4beta->6)-epicatechin-3-O-gallate	HMDB
Procyanidin b-5 3,3'-di-O-gallate	HMDB
Procyanidin b5 3,3'-di-O-gallate	HMDB
(2R,3R)-2-(3,4-Dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acid	Generator
Procyanidin b5 3,3'-digallic acid	Generator

Chemical Formula

C₄₄H₃₄O₂₀

Average Molecular Weight

882.7288

Monoisotopic Molecular Weight

882.164343528

IUPAC Name

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

Traditional Name

CAS Registry Number

106533-60-2

SMILES

OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1

InChI Identifier

InChI=1S/C44H34O20/c45-19-11-25(50)34-32(12-19)62-41(16-2-4-22(47)24(49)6-16)42(64-44(60)18-9-29(54)39(58)30(55)10-18)36(34)35-26(51)14-31-20(37(35)56)13-33(40(61-31)15-1-3-21(46)23(48)5-15)63-43(59)17-7-27(52)38(57)28(53)8-17/h1-12,14,33,36,40-42,45-58H,13H2/t33-,36-,40-,41-,42-/m1/s1

InChI Key

LFBGVECYPPCVDS-QNPRKUGLSA-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
Proanthocyanidin
Bi- and polyflavonoid skeleton
Catechin gallate
Catechin
Hydroxyflavonoid
Flavan-3-ol
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Flavan
Galloyl ester
Gallic acid or derivatives
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
P-hydroxybenzoic acid alkyl ester
Benzoate ester
Chromane
Benzopyran
1-benzopyran
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
Catechol
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Polyol
Ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0039299)

Cellular substructure

Membrane (HMDB: HMDB0039299)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039299)

Source

Exogenous

Food

Food (HMDB: HMDB0039299)

Tea

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0039299)

Not Available

Nutrient (HMDB: HMDB0039299)

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
Water Solubility	0.1 g/L	ALOGPS
logP	3.91	ALOGPS
logP	6.28	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.77	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	354.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	218.04 m³·mol⁻¹	ChemAxon
Polarizability	82.71 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	274.319	30932474
DeepCCS	[M-H]-	272.596	30932474
DeepCCS	[M-2H]-	306.628	30932474
DeepCCS	[M+Na]+	280.535	30932474
AllCCS	[M+H]+	281.4	32859911
AllCCS	[M+H-H2O]+	281.3	32859911
AllCCS	[M+NH4]+	281.3	32859911
AllCCS	[M+Na]+	281.3	32859911
AllCCS	[M-H]-	271.1	32859911
AllCCS	[M+Na-2H]-	275.1	32859911
AllCCS	[M+HCOO]-	279.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Di-O-galloylprocyanidin B5	OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1	11415.9	Standard polar	33892256
3,3'-Di-O-galloylprocyanidin B5	OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1	6816.0	Standard non polar	33892256
3,3'-Di-O-galloylprocyanidin B5	OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1	8620.4	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 10V, Positive-QTOF	splash10-0h0r-0510090450-63ffcd0d28bc59174ac6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 20V, Positive-QTOF	splash10-0f6x-0962370210-d5100a5daad246a350c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 40V, Positive-QTOF	splash10-0zfr-0980010010-d685131fe4fbd1c54354	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 10V, Negative-QTOF	splash10-001i-0300000390-81e6ebc0684396851459	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 20V, Negative-QTOF	splash10-0gdi-0903100440-bbdd35b047bcb5fc9ecf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 40V, Negative-QTOF	splash10-016r-0900001000-b02b0171cd108205f5ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 10V, Negative-QTOF	splash10-003r-0010000590-2866434216c3712c0e99	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 20V, Negative-QTOF	splash10-03e9-0501120790-93b127f1f166f07b2c83	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 40V, Negative-QTOF	splash10-00b9-1300010290-47d215c25d269d17708c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 10V, Positive-QTOF	splash10-02h9-0100012960-9834338d49f07b6c2547	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 20V, Positive-QTOF	splash10-01si-0300132890-6c868b630a67f9eac48d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 40V, Positive-QTOF	splash10-004i-0500041490-5256c67a9468e6492173	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB018845

KNApSAcK ID

C00009207

Chemspider ID

2343127

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3086518

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3,3'-Di-O-galloylprocyanidin B5 (HMDB0039299)

MOL for HMDB0039299 (3,3'-Di-O-galloylprocyanidin B5)

3D MOL for HMDB0039299 (3,3'-Di-O-galloylprocyanidin B5)

3D SDF for HMDB0039299 (3,3'-Di-O-galloylprocyanidin B5)

3D-SDF for HMDB0039299 (3,3'-Di-O-galloylprocyanidin B5)

PDB for HMDB0039299 (3,3'-Di-O-galloylprocyanidin B5)

3D PDB for HMDB0039299 (3,3'-Di-O-galloylprocyanidin B5)

SMILES for HMDB0039299 (3,3'-Di-O-galloylprocyanidin B5)

INCHI for HMDB0039299 (3,3'-Di-O-galloylprocyanidin B5)

Structure for HMDB0039299 (3,3'-Di-O-galloylprocyanidin B5)

3D Structure for HMDB0039299 (3,3'-Di-O-galloylprocyanidin B5)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra