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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:46:03 UTC

Update Date

2021-09-23 03:46:03 UTC

HMDB ID

HMDB0301932

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Epicatechin-(4beta->8)-epicatechin 3'-gallate

Description

Epicatechin-(4beta->8)-epicatechin 3'-gallate 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''. Epicatechin-(4beta->8)-epicatechin 3'-gallate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Epicatechin-(4beta->8)-epicatechin 3'-gallate can be synthesized from gallic acid. Epicatechin-(4beta->8)-epicatechin 3'-gallate can also be synthesized into procyanidin B2. Epicatechin-(4beta->8)-epicatechin 3'-gallate can be found in common buckwheat, common grape, and tea, which makes epicatechin-(4beta->8)-epicatechin 3'-gallate a potential biomarker for the consumption of these food products.

Structure

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

  Mrv0541 10221206002D          

 53 59  0  0  0  0            999 V2000
   -9.3278    2.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3278    2.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0423    3.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7568    2.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7568    2.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0423    1.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8988    2.0165    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8988    2.8415    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6133    3.2541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6133    1.6040    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0423    0.7791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4713    3.2540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1844    3.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7554    3.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7554    4.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4699    4.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1844    4.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0409    4.4915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4699    5.3165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8420   -1.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1276   -1.5060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1276   -3.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6986   -1.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9842   -0.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2696   -3.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8406   -5.6308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8407   -3.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2695   -6.4559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6986   -3.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4131   -4.3935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  9  2  1  0  0  0  0
  2  1  1  0  0  0  0
  1 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  6 11  1  0  0  0  0
  4 12  1  0  0  0  0
  8 13  1  6  0  0  0
 17 13  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
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 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
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 21 22  2  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
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 27 26  1  0  0  0  0
 27 30  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 33 31  2  0  0  0  0
 31 34  1  0  0  0  0
 32 33  1  0  0  0  0
 32 36  2  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 29 39  1  6  0  0  0
 22 40  1  0  0  0  0
 10 21  1  1  0  0  0
 35 41  1  0  0  0  0
  7 42  1  6  0  0  0
 52 39  1  0  0  0  0
 43 44  2  0  0  0  0
 43 48  1  0  0  0  0
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 44 49  1  0  0  0  0
 45 50  1  0  0  0  0
 43 51  1  0  0  0  0
 47 52  1  0  0  0  0
 52 53  2  0  0  0  0
M  END

HMDB0301932
     RDKit          3D
Epicatechin-(4beta->8)-epicatechin 3'-gallate
 83 89  0  0  0  0  0  0  0  0999 V2000
    4.6461   -1.1799   -2.7515 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740   -0.8761   -1.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1990   -0.2281   -1.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2584    0.1275   -2.3425 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1877    1.6214   -2.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249    2.3115   -1.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5799    3.5831   -1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    4.3140   -1.5947 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6979    4.1871   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4108    3.5001    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2499    4.1242    1.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6765    2.2222   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8606    1.5069    0.2237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8845    1.2767    1.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957    1.2434    2.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023    1.4323    1.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7522    1.0311    3.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9383    0.8433    4.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9377    0.6285    5.8436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1057    0.8793    3.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3772    1.8562    0.4165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5388    1.2962   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5271    1.6633   -1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7596    0.3115   -1.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8669   -0.1251   -2.4466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8873   -0.5524   -1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1531   -1.9143   -1.2101 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1443    1.9404   -0.3803 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.2136    1.6516   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378    0.3764   -1.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3417   -1.2364   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912   -0.9631    0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9958   -1.2816    1.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5418   -2.5980   -0.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0014    2.9999   -0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9874    1.8156   -2.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003   -0.6923   -3.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002   -0.9094    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -3.0672    1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1550   -0.4853    1.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7446   -2.0610   -1.8716 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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 31 24  1  0
  4 54  1  6
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  8 57  1  0
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 48 80  1  0
 50 81  1  0
 52 82  1  0
 53 83  1  0
M  END

  Mrv0541 10221206002D          

 53 59  0  0  0  0            999 V2000
   -9.3278    2.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3278    2.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0423    3.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7568    2.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9  2  1  0  0  0  0
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 10 21  1  1  0  0  0
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  7 42  1  6  0  0  0
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 52 53  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301932

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1[C@H](OC2=CC(O)=CC(O)=C2[C@@H]1C1=C(O)C=C(O)C2=C1O[C@@H]([C@@H](C2)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C37H30O16/c38-16-9-23(44)29-27(10-16)51-35(14-2-4-19(40)22(43)6-14)33(49)31(29)30-24(45)12-20(41)17-11-28(52-37(50)15-7-25(46)32(48)26(47)8-15)34(53-36(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,28,31,33-35,38-49H,11H2/t28-,31-,33-,34-,35-/m1/s1

> <INCHI_KEY>
VLFKNLZNDSEVBZ-BTWXELLASA-N

> <FORMULA>
C37H30O16

> <MOLECULAR_WEIGHT>
730.6245

> <EXACT_MASS>
730.153384912

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
68.50189909051352

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
4.700348897333333

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.848679852950948

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.025033737550777

> <JCHEM_PKA_STRONGEST_BASIC>
-5.214620821846933

> <JCHEM_POLAR_SURFACE_AREA>
287.5199999999999

> <JCHEM_REFRACTIVITY>
182.27270000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.37e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301932
     RDKit          3D
Epicatechin-(4beta->8)-epicatechin 3'-gallate
 83 89  0  0  0  0  0  0  0  0999 V2000
    4.6461   -1.1799   -2.7515 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740   -0.8761   -1.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1990   -0.2281   -1.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2584    0.1275   -2.3425 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1877    1.6214   -2.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249    2.3115   -1.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5799    3.5831   -1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    4.3140   -1.5947 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6979    4.1871   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4108    3.5001    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2499    4.1242    1.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6765    2.2222   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8606    1.5069    0.2237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8845    1.2767    1.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957    1.2434    2.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023    1.4323    1.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7522    1.0311    3.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9383    0.8433    4.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9377    0.6285    5.8436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1057    0.8793    3.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824    1.0954    2.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701    1.1317    1.6228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3772    1.8562    0.4165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5388    1.2962   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4283    2.1357   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5271    1.6633   -1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7596    0.3115   -1.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8669   -0.1251   -2.4466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8873   -0.5524   -1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1531   -1.9143   -1.2101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7857   -0.0610   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1443    1.9404   -0.3803 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4124    1.2476   -1.5967 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2136    1.6516   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378    0.3764   -1.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9088   -0.4673   -2.1735 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9426   -1.7857   -1.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9883   -1.8491   -0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211   -3.0441    0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0070   -4.2274   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -5.4191    0.5547 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616   -4.2140   -1.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494   -5.4289   -2.1828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295   -2.9886   -2.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -1.2364   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912   -0.9631    0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9958   -1.2816    1.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7019   -0.9903    3.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1877   -1.8886    1.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1566   -2.2433    2.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4392   -2.1630    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6522   -2.7802   -0.1519 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5358   -1.8438   -0.8351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885   -0.2621   -3.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2020    2.0366   -2.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7246    1.7520   -3.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3800    4.0096   -2.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9224    5.2011    0.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    3.6565    1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7344    0.4371   -0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894    1.4259    2.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1661    0.9993    4.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8806   -0.3139    6.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0733    0.7406    4.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7051    2.8984    0.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2315    3.2173   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1775    2.4059   -2.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0014    2.9999   -0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5003   -0.6923   -3.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002   -0.9094    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8948   -2.9904   -3.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1550   -0.4853    1.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2747   -1.1756    3.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0322   -2.0726    3.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8397   -2.9836   -1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7446   -2.0610   -1.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
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  5  6  1  0
  6  7  2  0
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 10 11  1  0
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 15 16  1  0
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 18 19  1  0
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 45 46  2  0
 46 47  1  0
 47 48  1  0
 47 49  2  0
 49 50  1  0
 49 51  1  0
 51 52  1  0
 51 53  2  0
 36  4  1  0
 44 37  1  0
 53 45  1  0
 34  6  1  0
 32 13  1  0
 21 14  1  0
 31 24  1  0
  4 54  1  6
  5 55  1  0
  5 56  1  0
  8 57  1  0
  9 58  1  0
 11 59  1  0
 13 60  1  6
 16 61  1  0
 17 62  1  0
 19 63  1  0
 20 64  1  0
 23 65  1  1
 25 66  1  0
 26 67  1  0
 28 68  1  0
 30 69  1  0
 31 70  1  0
 32 71  1  6
 33 72  1  0
 36 73  1  6
 38 74  1  0
 39 75  1  0
 41 76  1  0
 43 77  1  0
 44 78  1  0
 46 79  1  0
 48 80  1  0
 50 81  1  0
 52 82  1  0
 53 83  1  0
M  END

HEADER    PROTEIN                                 22-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-OCT-12         0                                  
HETATM    1  C   UNK     0     -17.412   3.764   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -17.412   5.304   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -18.746   6.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -20.079   5.304   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -20.079   3.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -18.746   2.994   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -14.744   3.764   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -14.744   5.304   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -16.078   6.074   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0     -16.078   2.994   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -18.746   1.454   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0     -21.413   6.074   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0     -13.411   6.074   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.743   6.074   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -10.743   7.614   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.077   8.384   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -13.411   7.614   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.077   5.304   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -9.410   8.384   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -12.077   9.924   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -15.972  -2.811   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -17.306  -3.581   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -17.306  -5.121   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -15.972  -5.891   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.638  -5.121   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -14.638  -3.581   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -13.305  -2.811   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -13.305  -5.891   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.971  -5.121   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -11.971  -3.581   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.637  -2.811   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.304  -0.501   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.637  -1.271   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -9.304  -3.581   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -7.970  -2.811   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.970  -1.271   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.636  -0.501   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -15.972  -7.431   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -10.637  -5.891   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -18.639  -2.811   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -6.636  -3.581   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -13.411   2.994   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -7.970 -10.511   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -6.636  -9.741   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -6.636  -8.201   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -7.970  -7.431   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -9.304  -8.201   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -9.303  -9.741   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -5.302 -10.511   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -5.303  -7.431   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -7.970 -12.051   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0     -10.637  -7.431   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0     -11.971  -8.201   0.000  0.00  0.00           O+0
CONECT    1    6    2   10                                                  
CONECT    2    3    9    1                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   11                                                  
CONECT    7    8   10   42                                                  
CONECT    8    7    9   13                                                  
CONECT    9    2    8                                                       
CONECT   10    1    7   21                                                  
CONECT   11    6                                                            
CONECT   12    4                                                            
CONECT   13    8   17   18                                                  
CONECT   14   15   18                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   20                                                  
CONECT   17   13   16                                                       
CONECT   18   13   14                                                       
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   22   26   10                                                  
CONECT   22   21   23   40                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   38                                                  
CONECT   25   24   28   26                                                  
CONECT   26   21   25   27                                                  
CONECT   27   26   30                                                       
CONECT   28   25   29                                                       
CONECT   29   28   30   39                                                  
CONECT   30   27   29   31                                                  
CONECT   31   30   33   34                                                  
CONECT   32   33   36                                                       
CONECT   33   31   32                                                       
CONECT   34   31   35                                                       
CONECT   35   34   36   41                                                  
CONECT   36   32   35   37                                                  
CONECT   37   36                                                            
CONECT   38   24                                                            
CONECT   39   29   52                                                       
CONECT   40   22                                                            
CONECT   41   35                                                            
CONECT   42    7                                                            
CONECT   43   44   48   51                                                  
CONECT   44   43   45   49                                                  
CONECT   45   44   46   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   52                                                  
CONECT   48   43   47                                                       
CONECT   49   44                                                            
CONECT   50   45                                                            
CONECT   51   43                                                            
CONECT   52   39   47   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  118    0
END

COMPND    HMDB0301932
HETATM    1  O1  UNL     1       4.646  -1.180  -2.751  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.374  -0.876  -1.586  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.199  -0.228  -1.352  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.258   0.127  -2.343  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.188   1.621  -2.560  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.325   2.312  -1.609  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.580   3.583  -1.176  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.677   4.314  -1.595  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.698   4.187  -0.267  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.411   3.500   0.180  1.00  0.00           C  
HETATM   11  O4  UNL     1      -1.250   4.124   1.067  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.676   2.222  -0.247  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.861   1.507   0.224  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.885   1.277   1.698  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.696   1.243   2.423  1.00  0.00           C  
HETATM   16  O5  UNL     1       0.502   1.432   1.726  1.00  0.00           O  
HETATM   17  C12 UNL     1      -0.752   1.031   3.763  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.938   0.843   4.463  1.00  0.00           C  
HETATM   19  O6  UNL     1      -1.938   0.629   5.844  1.00  0.00           O  
HETATM   20  C14 UNL     1      -3.106   0.879   3.734  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.082   1.095   2.355  1.00  0.00           C  
HETATM   22  O7  UNL     1      -4.270   1.132   1.623  1.00  0.00           O  
HETATM   23  C16 UNL     1      -4.377   1.856   0.417  1.00  0.00           C  
HETATM   24  C17 UNL     1      -5.539   1.296  -0.327  1.00  0.00           C  
HETATM   25  C18 UNL     1      -6.428   2.136  -0.963  1.00  0.00           C  
HETATM   26  C19 UNL     1      -7.527   1.663  -1.663  1.00  0.00           C  
HETATM   27  C20 UNL     1      -7.760   0.312  -1.739  1.00  0.00           C  
HETATM   28  O8  UNL     1      -8.867  -0.125  -2.447  1.00  0.00           O  
HETATM   29  C21 UNL     1      -6.887  -0.552  -1.113  1.00  0.00           C  
HETATM   30  O9  UNL     1      -7.153  -1.914  -1.210  1.00  0.00           O  
HETATM   31  C22 UNL     1      -5.786  -0.061  -0.412  1.00  0.00           C  
HETATM   32  C23 UNL     1      -3.144   1.940  -0.380  1.00  0.00           C  
HETATM   33  O10 UNL     1      -3.412   1.248  -1.597  1.00  0.00           O  
HETATM   34  C24 UNL     1       0.214   1.652  -1.146  1.00  0.00           C  
HETATM   35  O11 UNL     1      -0.038   0.376  -1.580  1.00  0.00           O  
HETATM   36  C25 UNL     1       0.909  -0.467  -2.174  1.00  0.00           C  
HETATM   37  C26 UNL     1       0.943  -1.786  -1.483  1.00  0.00           C  
HETATM   38  C27 UNL     1       0.988  -1.849  -0.105  1.00  0.00           C  
HETATM   39  C28 UNL     1       1.021  -3.044   0.594  1.00  0.00           C  
HETATM   40  C29 UNL     1       1.007  -4.227  -0.132  1.00  0.00           C  
HETATM   41  O12 UNL     1       1.039  -5.419   0.555  1.00  0.00           O  
HETATM   42  C30 UNL     1       0.962  -4.214  -1.508  1.00  0.00           C  
HETATM   43  O13 UNL     1       0.949  -5.429  -2.183  1.00  0.00           O  
HETATM   44  C31 UNL     1       0.930  -2.989  -2.178  1.00  0.00           C  
HETATM   45  C32 UNL     1       5.342  -1.236  -0.536  1.00  0.00           C  
HETATM   46  C33 UNL     1       5.091  -0.963   0.798  1.00  0.00           C  
HETATM   47  C34 UNL     1       5.996  -1.282   1.803  1.00  0.00           C  
HETATM   48  O14 UNL     1       5.702  -0.990   3.117  1.00  0.00           O  
HETATM   49  C35 UNL     1       7.188  -1.889   1.494  1.00  0.00           C  
HETATM   50  O15 UNL     1       8.157  -2.243   2.446  1.00  0.00           O  
HETATM   51  C36 UNL     1       7.439  -2.163   0.156  1.00  0.00           C  
HETATM   52  O16 UNL     1       8.652  -2.780  -0.152  1.00  0.00           O  
HETATM   53  C37 UNL     1       6.536  -1.844  -0.835  1.00  0.00           C  
HETATM   54  H1  UNL     1       2.689  -0.262  -3.294  1.00  0.00           H  
HETATM   55  H2  UNL     1       3.202   2.037  -2.630  1.00  0.00           H  
HETATM   56  H3  UNL     1       1.725   1.752  -3.584  1.00  0.00           H  
HETATM   57  H4  UNL     1       3.380   4.010  -2.235  1.00  0.00           H  
HETATM   58  H5  UNL     1       0.922   5.201   0.063  1.00  0.00           H  
HETATM   59  H6  UNL     1      -2.119   3.657   1.354  1.00  0.00           H  
HETATM   60  H7  UNL     1      -1.734   0.437  -0.174  1.00  0.00           H  
HETATM   61  H8  UNL     1       1.389   1.426   2.164  1.00  0.00           H  
HETATM   62  H9  UNL     1       0.166   0.999   4.352  1.00  0.00           H  
HETATM   63  H10 UNL     1      -1.881  -0.314   6.238  1.00  0.00           H  
HETATM   64  H11 UNL     1      -4.073   0.741   4.223  1.00  0.00           H  
HETATM   65  H12 UNL     1      -4.705   2.898   0.717  1.00  0.00           H  
HETATM   66  H13 UNL     1      -6.231   3.217  -0.895  1.00  0.00           H  
HETATM   67  H14 UNL     1      -8.178   2.406  -2.136  1.00  0.00           H  
HETATM   68  H15 UNL     1      -9.068  -1.116  -2.522  1.00  0.00           H  
HETATM   69  H16 UNL     1      -6.542  -2.598  -0.768  1.00  0.00           H  
HETATM   70  H17 UNL     1      -5.131  -0.760   0.061  1.00  0.00           H  
HETATM   71  H18 UNL     1      -3.001   3.000  -0.755  1.00  0.00           H  
HETATM   72  H19 UNL     1      -3.987   1.816  -2.172  1.00  0.00           H  
HETATM   73  H20 UNL     1       0.500  -0.692  -3.207  1.00  0.00           H  
HETATM   74  H21 UNL     1       1.000  -0.909   0.437  1.00  0.00           H  
HETATM   75  H22 UNL     1       1.058  -3.067   1.693  1.00  0.00           H  
HETATM   76  H23 UNL     1       1.035  -6.332   0.157  1.00  0.00           H  
HETATM   77  H24 UNL     1       0.917  -5.563  -3.163  1.00  0.00           H  
HETATM   78  H25 UNL     1       0.895  -2.990  -3.256  1.00  0.00           H  
HETATM   79  H26 UNL     1       4.155  -0.485   1.047  1.00  0.00           H  
HETATM   80  H27 UNL     1       6.275  -1.176   3.901  1.00  0.00           H  
HETATM   81  H28 UNL     1       8.032  -2.073   3.426  1.00  0.00           H  
HETATM   82  H29 UNL     1       8.840  -2.984  -1.121  1.00  0.00           H  
HETATM   83  H30 UNL     1       6.745  -2.061  -1.872  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   45
CONECT    3    4
CONECT    4    5   36   54
CONECT    5    6   55   56
CONECT    6    7    7   34
CONECT    7    8    9
CONECT    8   57
CONECT    9   10   10   58
CONECT   10   11   12
CONECT   11   59
CONECT   12   13   34   34
CONECT   13   14   32   60
CONECT   14   15   15   21
CONECT   15   16   17
CONECT   16   61
CONECT   17   18   18   62
CONECT   18   19   20
CONECT   19   63
CONECT   20   21   21   64
CONECT   21   22
CONECT   22   23
CONECT   23   24   32   65
CONECT   24   25   25   31
CONECT   25   26   66
CONECT   26   27   27   67
CONECT   27   28   29
CONECT   28   68
CONECT   29   30   31   31
CONECT   30   69
CONECT   31   70
CONECT   32   33   71
CONECT   33   72
CONECT   34   35
CONECT   35   36
CONECT   36   37   73
CONECT   37   38   38   44
CONECT   38   39   74
CONECT   39   40   40   75
CONECT   40   41   42
CONECT   41   76
CONECT   42   43   44   44
CONECT   43   77
CONECT   44   78
CONECT   45   46   46   53
CONECT   46   47   79
CONECT   47   48   49   49
CONECT   48   80
CONECT   49   50   51
CONECT   50   81
CONECT   51   52   53   53
CONECT   52   82
CONECT   53   83
END

HMDB0301932
     RDKit          3D
Epicatechin-(4beta->8)-epicatechin 3'-gallate
 83 89  0  0  0  0  0  0  0  0999 V2000
    4.6461   -1.1799   -2.7515 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740   -0.8761   -1.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1990   -0.2281   -1.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2584    0.1275   -2.3425 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1877    1.6214   -2.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249    2.3115   -1.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5799    3.5831   -1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    4.3140   -1.5947 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6979    4.1871   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4108    3.5001    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2499    4.1242    1.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6765    2.2222   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8606    1.5069    0.2237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8845    1.2767    1.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957    1.2434    2.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023    1.4323    1.7259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7522    1.0311    3.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9383    0.8433    4.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9377    0.6285    5.8436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1057    0.8793    3.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824    1.0954    2.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701    1.1317    1.6228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3772    1.8562    0.4165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5388    1.2962   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4283    2.1357   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5271    1.6633   -1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7596    0.3115   -1.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8669   -0.1251   -2.4466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8873   -0.5524   -1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1531   -1.9143   -1.2101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7857   -0.0610   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1443    1.9404   -0.3803 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4124    1.2476   -1.5967 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2136    1.6516   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378    0.3764   -1.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9088   -0.4673   -2.1735 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9426   -1.7857   -1.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9883   -1.8491   -0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211   -3.0441    0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0070   -4.2274   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -5.4191    0.5547 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616   -4.2140   -1.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494   -5.4289   -2.1828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295   -2.9886   -2.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -1.2364   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912   -0.9631    0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9958   -1.2816    1.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7019   -0.9903    3.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1877   -1.8886    1.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1566   -2.2433    2.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4392   -2.1630    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6522   -2.7802   -0.1519 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5358   -1.8438   -0.8351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885   -0.2621   -3.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2020    2.0366   -2.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7246    1.7520   -3.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3800    4.0096   -2.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9224    5.2011    0.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    3.6565    1.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7344    0.4371   -0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894    1.4259    2.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1661    0.9993    4.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8806   -0.3139    6.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0733    0.7406    4.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7051    2.8984    0.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2315    3.2173   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1775    2.4059   -2.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0681   -1.1161   -2.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5418   -2.5980   -0.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1315   -0.7605    0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0014    2.9999   -0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9874    1.8156   -2.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003   -0.6923   -3.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002   -0.9094    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -3.0672    1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0348   -6.3324    0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171   -5.5626   -3.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948   -2.9904   -3.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1550   -0.4853    1.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2747   -1.1756    3.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0322   -2.0726    3.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8397   -2.9836   -1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7446   -2.0610   -1.8716 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
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  7  8  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Epicatechin-(4beta->8)-(-)-epicatechin-3'-O-gallate	ChEBI
(-)-Epicatechin-(4b->8)-(-)-epicatechin-3'-O-gallate	Generator
(-)-Epicatechin-(4b->8)-(-)-epicatechin-3'-O-gallic acid	Generator
(-)-Epicatechin-(4beta->8)-(-)-epicatechin-3'-O-gallic acid	Generator
(-)-Epicatechin-(4β->8)-(-)-epicatechin-3'-O-gallate	Generator
(-)-Epicatechin-(4β->8)-(-)-epicatechin-3'-O-gallic acid	Generator
Procyanidin b2 3'-O-gallic acid	Generator
Epicatechin-(4b->8)-epicatechin 3'-gallate	Generator
Epicatechin-(4b->8)-epicatechin 3'-gallic acid	Generator
Epicatechin-(4beta->8)-epicatechin 3'-gallic acid	Generator
Epicatechin-(4β->8)-epicatechin 3'-gallate	Generator
Epicatechin-(4β->8)-epicatechin 3'-gallic acid	Generator

Chemical Formula

C₃₇H₃₀O₁₆

Average Molecular Weight

730.6245

Monoisotopic Molecular Weight

730.153384912

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](OC2=CC(O)=CC(O)=C2[C@@H]1C1=C(O)C=C(O)C2=C1O[C@@H]([C@@H](C2)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C37H30O16/c38-16-9-23(44)29-27(10-16)51-35(14-2-4-19(40)22(43)6-14)33(49)31(29)30-24(45)12-20(41)17-11-28(52-37(50)15-7-25(46)32(48)26(47)8-15)34(53-36(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,28,31,33-35,38-49H,11H2/t28-,31-,33-,34-,35-/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:75647 )
gallate ester (CHEBI:75647 )
proanthocyanidin (CHEBI:75647 )
biflavonoid (CHEBI:75647 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301932)

Food

Cereal and cereal product

Cereal

Common buckwheat (FooDB: FOOD00079)

Tea

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

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	3.32	ALOGPS
logP	4.7	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.03	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	287.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	182.27 m³·mol⁻¹	ChemAxon
Polarizability	68.5 Å³	ChemAxon
Number of Rings	7	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
AllCCS	[M+H]+	261.785	32859911
AllCCS	[M+H-H2O]+	261.064	32859911
AllCCS	[M+Na]+	262.585	32859911
AllCCS	[M+NH4]+	262.412	32859911
AllCCS	[M-H]-	252.259	32859911
AllCCS	[M+Na-2H]-	255.165	32859911
AllCCS	[M+HCOO]-	258.486	32859911
DeepCCS	[M+H]+	248.17	30932474
DeepCCS	[M-H]-	246.275	30932474
DeepCCS	[M-2H]-	280.221	30932474
DeepCCS	[M+Na]+	254.242	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epicatechin-(4beta->8)-epicatechin 3'-gallate,2TMS,isomer #20	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H](C1=C(O[Si](C)(C)C)C=C(O)C3=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)C3)[C@@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O2	6804.7	Semi standard non polar	33892256
Epicatechin-(4beta->8)-epicatechin 3'-gallate,2TMS,isomer #20	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H](C1=C(O[Si](C)(C)C)C=C(O)C3=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)C3)[C@@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O2	5587.2	Standard non polar	33892256
Epicatechin-(4beta->8)-epicatechin 3'-gallate,2TMS,isomer #20	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H](C1=C(O[Si](C)(C)C)C=C(O)C3=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)C3)[C@@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O2	9823.4	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 - Epicatechin-(4beta->8)-epicatechin 3'-gallate 10V, Positive-QTOF	splash10-01u0-0510940600-86b1b7089e99f624871a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 20V, Positive-QTOF	splash10-0pbi-0972511100-dfee234fea53ce5f1e33	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 40V, Positive-QTOF	splash10-0pb9-0691000000-ef5b24d7cb68459abc48	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 10V, Negative-QTOF	splash10-004i-0300111900-27b6457ff92e59214905	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 20V, Negative-QTOF	splash10-0gdi-0923202200-42e7a77963f6441053b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 40V, Negative-QTOF	splash10-00or-0910000000-749f45a9d688840195ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 10V, Positive-QTOF	splash10-01q9-0100153900-41a928c12f5b41f3c09e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 20V, Positive-QTOF	splash10-0fl3-0641916500-1898991c3855716ce921	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 40V, Positive-QTOF	splash10-00di-0960344100-9ea07afc55b5ea9c6453	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 10V, Negative-QTOF	splash10-004i-0300070900-132b4b350214afa8d79b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 20V, Negative-QTOF	splash10-0fb9-0900023300-dca9be94836b87320d82	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin-(4beta->8)-epicatechin 3'-gallate 40V, Negative-QTOF	splash10-00bc-2822609100-fffd213c35ea07cc7bb7	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

FDB001640

KNApSAcK ID

Not Available

Chemspider ID

10252512

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15593124

PDB ID

Not Available

ChEBI ID

75647

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 Epicatechin-(4beta->8)-epicatechin 3'-gallate (HMDB0301932)

MOL for HMDB0301932 (Epicatechin-(4beta->8)-epicatechin 3'-gallate)

3D MOL for HMDB0301932 (Epicatechin-(4beta->8)-epicatechin 3'-gallate)

3D SDF for HMDB0301932 (Epicatechin-(4beta->8)-epicatechin 3'-gallate)

3D-SDF for HMDB0301932 (Epicatechin-(4beta->8)-epicatechin 3'-gallate)

PDB for HMDB0301932 (Epicatechin-(4beta->8)-epicatechin 3'-gallate)

3D PDB for HMDB0301932 (Epicatechin-(4beta->8)-epicatechin 3'-gallate)

SMILES for HMDB0301932 (Epicatechin-(4beta->8)-epicatechin 3'-gallate)

INCHI for HMDB0301932 (Epicatechin-(4beta->8)-epicatechin 3'-gallate)

Structure for HMDB0301932 (Epicatechin-(4beta->8)-epicatechin 3'-gallate)

3D Structure for HMDB0301932 (Epicatechin-(4beta->8)-epicatechin 3'-gallate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra