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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:53:59 UTC

Update Date

2022-03-07 02:55:26 UTC

HMDB ID

HMDB0037650

Secondary Accession Numbers

HMDB37650

Metabolite Identification

Common Name

Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate

Description

Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 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''. Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea and black tea. This could make epigallocatechin-(4beta->8)-epicatechin 3-O-gallate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate.

Structure

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

Epigallocatechin-(4b,8)-epicatechin-3-O-gallate ester
  Mrv1572001071617282D          

 54 60  0  0  1  0            999 V2000
    9.7846   10.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3581   12.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7870   10.9541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2135    8.4963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0815    9.9916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9291   10.3869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    7.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001   12.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9304   12.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5014   14.6666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.3570   11.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6425    5.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1 20  1  0  0  0  0
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 52 54  2  0  0  0  0
 53 54  1  0  0  0  0
M  END

HMDB0037650
     RDKit          3D
Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate
 84 90  0  0  0  0  0  0  0  0999 V2000
    4.4231    0.8920   -2.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7277    1.1317   -0.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Epigallocatechin-(4b,8)-epicatechin-3-O-gallate ester
  Mrv1572001071617282D          

 54 60  0  0  1  0            999 V2000
    9.7846   10.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3581   12.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7870   10.9541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2135    8.4963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0815    9.9916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9291   10.3869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    7.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001   12.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5014   14.6666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.0714    7.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6425    5.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0714    6.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3581   10.9541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3557   10.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0701    9.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6435   11.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0725   11.3666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0701    8.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6435   12.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0725   12.1915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6411    9.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9291   10.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    8.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4990    9.7338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4990    8.9087    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7846    8.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6411    8.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7870   12.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9291   12.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2135   10.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2146   11.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2146   12.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5014   12.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7870   13.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2159   12.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5014   13.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9280    9.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2135   10.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2135    7.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2159   13.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6425   10.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9280    7.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6425   10.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9280   11.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6425    7.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9280    6.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3570    7.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6425    6.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3570    6.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  1 29  1  0  0  0  0
  2 24  1  0  0  0  0
  2 25  1  0  0  0  0
 22  3  1  6  0  0  0
 30  4  1  6  0  0  0
  4 44  1  0  0  0  0
  5 26  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 37  1  0  0  0  0
  9 40  1  0  0  0  0
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 52 54  2  0  0  0  0
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037650

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1[C@H](OC2=C([C@@H]1C1=C(O)C=C(O)C3=C1O[C@@H]([C@@H](C3)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(O)=CC(O)=C2)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C37H30O17/c38-15-8-20(42)28-26(9-15)52-35(13-4-22(44)31(48)23(45)5-13)33(50)30(28)29-21(43)11-18(40)16-10-27(53-37(51)14-6-24(46)32(49)25(47)7-14)34(54-36(16)29)12-1-2-17(39)19(41)3-12/h1-9,11,27,30,33-35,38-50H,10H2/t27-,30-,33-,34-,35-/m1/s1

> <INCHI_KEY>
LQQNPVZIFKLQPE-RGOYVLDUSA-N

> <FORMULA>
C37H30O17

> <MOLECULAR_WEIGHT>
746.63

> <EXACT_MASS>
746.148299506

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
71.23709507310133

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
4.396783575666666

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.753149189324416

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.001657823545285

> <JCHEM_PKA_STRONGEST_BASIC>
-5.216193122819395

> <JCHEM_POLAR_SURFACE_AREA>
307.75

> <JCHEM_REFRACTIVITY>
184.25360000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037650
     RDKit          3D
Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate
 84 90  0  0  0  0  0  0  0  0999 V2000
    4.4231    0.8920   -2.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7277    1.1317   -0.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687    1.3140    0.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059    1.2831   -0.2500 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7437    2.6520    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    2.7308   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    3.7770   -1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268    4.8915   -1.4397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130    3.7272   -1.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005    2.5927   -1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    2.6179   -2.0411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686    1.5079   -0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    0.3303   -0.5793 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8614    0.7091    0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0289    1.2220    1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9228    1.3482    2.1024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2634    1.6220    1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3895    1.5219    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0363    0.6108   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9530   -1.0104   -2.1712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5275   -2.1675   -1.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9022   -2.3476   -1.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5844   -3.3992   -1.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9157   -3.5806   -1.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9056   -4.3681   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6153   -5.4236    0.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5520   -4.1933   -0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8260   -5.1088    0.5463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -3.1109   -0.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -0.5431   -1.7839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6983   -1.5919   -1.8228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919    1.5942   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1649    0.5675    0.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5234    0.1462    0.2749 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0782   -0.6553    1.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.3559    2.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3639   -1.0842    3.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686   -2.1951    3.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7138   -2.9653    4.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4139   -2.5165    2.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056   -3.6110    1.7332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748   -1.7546    1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1309    1.1843   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1012    1.0105   -1.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630    1.0484   -1.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4148    0.8678   -2.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8768    1.2710    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2300    1.3303    0.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9044    1.4515    1.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3925    1.6708    2.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5534    1.4107    0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1647    1.2143   -1.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5620    2.7096    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6564    5.0126   -1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6601    4.5790   -2.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0268    1.0218    1.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9886    1.2343   -0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6404    1.8425    3.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7946    1.5410    1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  5  6  1  0
  6  7  2  0
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 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  1  0
 43 45  2  0
  2 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  1  0
 48 50  2  0
 50 51  1  0
 50 52  1  0
 52 53  1  0
 52 54  2  0
 37  4  1  0
 45 38  1  0
 54 46  1  0
 35  6  1  0
 33 13  1  0
 21 14  1  0
 32 24  1  0
  4 55  1  6
  5 56  1  0
  5 57  1  0
  8 58  1  0
  9 59  1  0
 11 60  1  0
 13 61  1  1
 16 62  1  0
 17 63  1  0
 19 64  1  0
 20 65  1  0
 23 66  1  6
 25 67  1  0
 27 68  1  0
 29 69  1  0
 31 70  1  0
 32 71  1  0
 33 72  1  6
 34 73  1  0
 37 74  1  6
 39 75  1  0
 40 76  1  0
 42 77  1  0
 44 78  1  0
 45 79  1  0
 47 80  1  0
 49 81  1  0
 51 82  1  0
 53 83  1  0
 54 84  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Epigallocatechin-(4b,8)-epicatechin-3-O-gallate es
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0      18.265  18.940   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      15.602  23.528   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.269  20.448   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      20.932  15.860   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.219  18.651   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.934  19.389   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      15.597  14.320   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      10.267  23.528   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      22.270  22.757   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      19.603  27.378   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      19.598  13.550   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      22.270  25.838   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      24.933  18.170   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      24.933  21.250   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      26.267  14.320   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      23.599   9.700   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      26.267  11.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      15.602  20.448   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.597  18.940   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.931  18.170   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.268  21.218   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.935  21.218   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.931  16.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.268  22.757   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.935  22.757   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.263  18.170   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.934  20.448   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.597  15.860   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.598  18.170   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.598  16.630   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.265  15.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.263  16.630   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.269  23.528   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.934  23.528   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.932  18.940   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.601  21.218   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.601  22.757   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      19.603  22.757   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      18.269  25.068   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.936  23.528   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      19.603  25.838   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      22.266  18.170   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      20.932  20.480   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      20.932  14.320   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      20.936  25.068   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      23.599  18.940   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      22.266  13.550   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      23.599  20.480   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      22.266  21.250   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      23.599  14.320   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      22.266  12.010   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      24.933  13.550   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      23.599  11.240   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      24.933  12.010   0.000  0.00  0.00           C+0
CONECT    1   20   29                                                       
CONECT    2   24   25                                                       
CONECT    3   22                                                            
CONECT    4   30   44                                                       
CONECT    5   26                                                            
CONECT    6   27                                                            
CONECT    7   28                                                            
CONECT    8   37                                                            
CONECT    9   40                                                            
CONECT   10   41                                                            
CONECT   11   44                                                            
CONECT   12   45                                                            
CONECT   13   46                                                            
CONECT   14   48                                                            
CONECT   15   52                                                            
CONECT   16   53                                                            
CONECT   17   54                                                            
CONECT   18   19   21   22                                                  
CONECT   19   18   20   26                                                  
CONECT   20    1   19   23                                                  
CONECT   21   18   24   27                                                  
CONECT   22    3   18   25                                                  
CONECT   23   20   28   31                                                  
CONECT   24    2   21   34                                                  
CONECT   25    2   22   33                                                  
CONECT   26    5   19   32                                                  
CONECT   27    6   21   36                                                  
CONECT   28    7   23   32                                                  
CONECT   29    1   30   35                                                  
CONECT   30    4   29   31                                                  
CONECT   31   23   30                                                       
CONECT   32   26   28                                                       
CONECT   33   25   38   39                                                  
CONECT   34   24   37                                                       
CONECT   35   29   42   43                                                  
CONECT   36   27   37                                                       
CONECT   37    8   34   36                                                  
CONECT   38   33   40                                                       
CONECT   39   33   41                                                       
CONECT   40    9   38   45                                                  
CONECT   41   10   39   45                                                  
CONECT   42   35   46                                                       
CONECT   43   35   49                                                       
CONECT   44    4   11   47                                                  
CONECT   45   12   40   41                                                  
CONECT   46   13   42   48                                                  
CONECT   47   44   50   51                                                  
CONECT   48   14   46   49                                                  
CONECT   49   43   48                                                       
CONECT   50   47   52                                                       
CONECT   51   47   53                                                       
CONECT   52   15   50   54                                                  
CONECT   53   16   51   54                                                  
CONECT   54   17   52   53                                                  
MASTER        0    0    0    0    0    0    0    0   54    0  120    0
END

COMPND    HMDB0037650
HETATM    1  O1  UNL     1       4.423   0.892  -2.038  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.728   1.132  -0.816  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.669   1.314   0.011  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.306   1.283  -0.250  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.744   2.652   0.127  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.405   2.731  -0.501  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.055   3.777  -1.219  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.727   4.892  -1.440  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.313   3.727  -1.729  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.101   2.593  -1.497  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.348   2.618  -2.041  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.669   1.508  -0.772  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.529   0.330  -0.579  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.861   0.709   0.001  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.029   1.222   1.263  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.923   1.348   2.102  1.00  0.00           O  
HETATM   17  C12 UNL     1      -5.263   1.622   1.753  1.00  0.00           C  
HETATM   18  C13 UNL     1      -6.390   1.522   0.991  1.00  0.00           C  
HETATM   19  O6  UNL     1      -7.648   1.905   1.427  1.00  0.00           O  
HETATM   20  C14 UNL     1      -6.277   1.011  -0.281  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.036   0.611  -0.766  1.00  0.00           C  
HETATM   22  O7  UNL     1      -4.907   0.086  -2.044  1.00  0.00           O  
HETATM   23  C16 UNL     1      -3.953  -1.010  -2.171  1.00  0.00           C  
HETATM   24  C17 UNL     1      -4.527  -2.167  -1.516  1.00  0.00           C  
HETATM   25  C18 UNL     1      -5.902  -2.348  -1.662  1.00  0.00           C  
HETATM   26  C19 UNL     1      -6.584  -3.399  -1.103  1.00  0.00           C  
HETATM   27  O8  UNL     1      -7.916  -3.581  -1.236  1.00  0.00           O  
HETATM   28  C20 UNL     1      -5.906  -4.368  -0.338  1.00  0.00           C  
HETATM   29  O9  UNL     1      -6.615  -5.424   0.220  1.00  0.00           O  
HETATM   30  C21 UNL     1      -4.552  -4.193  -0.193  1.00  0.00           C  
HETATM   31  O10 UNL     1      -3.826  -5.109   0.546  1.00  0.00           O  
HETATM   32  C22 UNL     1      -3.896  -3.111  -0.776  1.00  0.00           C  
HETATM   33  C23 UNL     1      -2.609  -0.543  -1.784  1.00  0.00           C  
HETATM   34  O11 UNL     1      -1.698  -1.592  -1.823  1.00  0.00           O  
HETATM   35  C24 UNL     1      -0.392   1.594  -0.274  1.00  0.00           C  
HETATM   36  O12 UNL     1       0.165   0.567   0.466  1.00  0.00           O  
HETATM   37  C25 UNL     1       1.523   0.146   0.275  1.00  0.00           C  
HETATM   38  C26 UNL     1       2.078  -0.655   1.338  1.00  0.00           C  
HETATM   39  C27 UNL     1       1.849  -0.356   2.656  1.00  0.00           C  
HETATM   40  C28 UNL     1       2.364  -1.084   3.718  1.00  0.00           C  
HETATM   41  C29 UNL     1       3.169  -2.195   3.422  1.00  0.00           C  
HETATM   42  O13 UNL     1       3.714  -2.965   4.449  1.00  0.00           O  
HETATM   43  C30 UNL     1       3.414  -2.517   2.106  1.00  0.00           C  
HETATM   44  O14 UNL     1       4.206  -3.611   1.733  1.00  0.00           O  
HETATM   45  C31 UNL     1       2.875  -1.755   1.098  1.00  0.00           C  
HETATM   46  C32 UNL     1       6.131   1.184  -0.449  1.00  0.00           C  
HETATM   47  C33 UNL     1       7.101   1.010  -1.396  1.00  0.00           C  
HETATM   48  C34 UNL     1       8.463   1.048  -1.119  1.00  0.00           C  
HETATM   49  O15 UNL     1       9.415   0.868  -2.110  1.00  0.00           O  
HETATM   50  C35 UNL     1       8.877   1.271   0.163  1.00  0.00           C  
HETATM   51  O16 UNL     1      10.230   1.330   0.539  1.00  0.00           O  
HETATM   52  C36 UNL     1       7.904   1.452   1.150  1.00  0.00           C  
HETATM   53  O17 UNL     1       8.393   1.671   2.427  1.00  0.00           O  
HETATM   54  C37 UNL     1       6.553   1.411   0.859  1.00  0.00           C  
HETATM   55  H1  UNL     1       2.165   1.214  -1.379  1.00  0.00           H  
HETATM   56  H2  UNL     1       2.456   3.411  -0.197  1.00  0.00           H  
HETATM   57  H3  UNL     1       1.562   2.710   1.229  1.00  0.00           H  
HETATM   58  H4  UNL     1       1.656   5.013  -1.097  1.00  0.00           H  
HETATM   59  H5  UNL     1      -1.660   4.579  -2.301  1.00  0.00           H  
HETATM   60  H6  UNL     1      -3.731   3.384  -2.586  1.00  0.00           H  
HETATM   61  H7  UNL     1      -2.049  -0.298   0.232  1.00  0.00           H  
HETATM   62  H8  UNL     1      -2.027   1.022   1.896  1.00  0.00           H  
HETATM   63  H9  UNL     1      -5.317   2.015   2.744  1.00  0.00           H  
HETATM   64  H10 UNL     1      -8.186   1.160   1.897  1.00  0.00           H  
HETATM   65  H11 UNL     1      -7.147   0.913  -0.926  1.00  0.00           H  
HETATM   66  H12 UNL     1      -3.951  -1.217  -3.284  1.00  0.00           H  
HETATM   67  H13 UNL     1      -6.486  -1.635  -2.222  1.00  0.00           H  
HETATM   68  H14 UNL     1      -8.735  -3.690  -1.319  1.00  0.00           H  
HETATM   69  H15 UNL     1      -6.231  -6.153   0.776  1.00  0.00           H  
HETATM   70  H16 UNL     1      -2.828  -4.995   0.657  1.00  0.00           H  
HETATM   71  H17 UNL     1      -2.846  -3.053  -0.607  1.00  0.00           H  
HETATM   72  H18 UNL     1      -2.260   0.131  -2.646  1.00  0.00           H  
HETATM   73  H19 UNL     1      -1.490  -1.917  -2.734  1.00  0.00           H  
HETATM   74  H20 UNL     1       1.403  -0.597  -0.601  1.00  0.00           H  
HETATM   75  H21 UNL     1       1.231   0.503   2.957  1.00  0.00           H  
HETATM   76  H22 UNL     1       2.179  -0.837   4.745  1.00  0.00           H  
HETATM   77  H23 UNL     1       3.523  -2.688   5.391  1.00  0.00           H  
HETATM   78  H24 UNL     1       4.617  -4.185   2.469  1.00  0.00           H  
HETATM   79  H25 UNL     1       3.071  -1.999   0.072  1.00  0.00           H  
HETATM   80  H26 UNL     1       6.787   0.829  -2.430  1.00  0.00           H  
HETATM   81  H27 UNL     1       9.173   0.709  -3.098  1.00  0.00           H  
HETATM   82  H28 UNL     1      10.989   1.234  -0.106  1.00  0.00           H  
HETATM   83  H29 UNL     1       7.640   1.843   3.159  1.00  0.00           H  
HETATM   84  H30 UNL     1       5.795   1.541   1.610  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   46
CONECT    3    4
CONECT    4    5   37   55
CONECT    5    6   56   57
CONECT    6    7    7   35
CONECT    7    8    9
CONECT    8   58
CONECT    9   10   10   59
CONECT   10   11   12
CONECT   11   60
CONECT   12   13   35   35
CONECT   13   14   33   61
CONECT   14   15   15   21
CONECT   15   16   17
CONECT   16   62
CONECT   17   18   18   63
CONECT   18   19   20
CONECT   19   64
CONECT   20   21   21   65
CONECT   21   22
CONECT   22   23
CONECT   23   24   33   66
CONECT   24   25   25   32
CONECT   25   26   67
CONECT   26   27   28   28
CONECT   27   68
CONECT   28   29   30
CONECT   29   69
CONECT   30   31   32   32
CONECT   31   70
CONECT   32   71
CONECT   33   34   72
CONECT   34   73
CONECT   35   36
CONECT   36   37
CONECT   37   38   74
CONECT   38   39   39   45
CONECT   39   40   75
CONECT   40   41   41   76
CONECT   41   42   43
CONECT   42   77
CONECT   43   44   45   45
CONECT   44   78
CONECT   45   79
CONECT   46   47   47   54
CONECT   47   48   80
CONECT   48   49   50   50
CONECT   49   81
CONECT   50   51   52
CONECT   51   82
CONECT   52   53   54   54
CONECT   53   83
CONECT   54   84
END

HMDB0037650
     RDKit          3D
Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate
 84 90  0  0  0  0  0  0  0  0999 V2000
    4.4231    0.8920   -2.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7277    1.1317   -0.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687    1.3140    0.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059    1.2831   -0.2500 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7437    2.6520    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    2.7308   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    3.7770   -1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268    4.8915   -1.4397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130    3.7272   -1.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1005    2.5927   -1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    2.6179   -2.0411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686    1.5079   -0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    0.3303   -0.5793 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8614    0.7091    0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0289    1.2220    1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9228    1.3482    2.1024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2634    1.6220    1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3895    1.5219    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6477    1.9046    1.4273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2774    1.0113   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0363    0.6108   -0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9072    0.0865   -2.0440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9530   -1.0104   -2.1712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5275   -2.1675   -1.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9022   -2.3476   -1.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5844   -3.3992   -1.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9157   -3.5806   -1.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9056   -4.3681   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6153   -5.4236    0.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5520   -4.1933   -0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8260   -5.1088    0.5463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -3.1109   -0.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -0.5431   -1.7839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6983   -1.5919   -1.8228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919    1.5942   -0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1649    0.5675    0.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5234    0.1462    0.2749 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0782   -0.6553    1.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.3559    2.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3639   -1.0842    3.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686   -2.1951    3.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7138   -2.9653    4.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4139   -2.5165    2.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056   -3.6110    1.7332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748   -1.7546    1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1309    1.1843   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1012    1.0105   -1.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630    1.0484   -1.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4148    0.8678   -2.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8768    1.2710    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2300    1.3303    0.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9044    1.4515    1.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3925    1.6708    2.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5534    1.4107    0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1647    1.2143   -1.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4561    3.4105   -0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5620    2.7096    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6564    5.0126   -1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6601    4.5790   -2.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7314    3.3835   -2.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0488   -0.2983    0.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0268    1.0218    1.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3174    2.0149    2.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1863    1.1604    1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1468    0.9128   -0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9509   -1.2168   -3.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4861   -1.6354   -2.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7350   -3.6899   -1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2308   -6.1534    0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8282   -4.9948    0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -3.0532   -0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2595    0.1312   -2.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4902   -1.9167   -2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4027   -0.5972   -0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308    0.5031    2.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789   -0.8369    4.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5227   -2.6879    5.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -4.1848    2.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0707   -1.9994    0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7869    0.8290   -2.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1732    0.7090   -3.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9886    1.2343   -0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6404    1.8425    3.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7946    1.5410    1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Epigallocatechin-(4b->8)-epicatechin 3-O-gallate	Generator
Epigallocatechin-(4b->8)-epicatechin 3-O-gallic acid	Generator
Epigallocatechin-(4beta->8)-epicatechin 3-O-gallic acid	Generator
Epigallocatechin-(4β->8)-epicatechin 3-O-gallate	Generator
Epigallocatechin-(4β->8)-epicatechin 3-O-gallic acid	Generator
Epigallocatechin(4b->8)epicatechin 3-O-gallate	HMDB
Epigallocatechin-(4beta->8)-epicatechin-3-O-gallate	HMDB
Epigallocatechin-(4beta->8)-epicatechin-3-O-gallate ester	HMDB
Epigallocatechin-(4b->8)-epicatechin-3-O-gallate ester	Generator
Epigallocatechin-(4b->8)-epicatechin-3-O-gallic acid ester	Generator
Epigallocatechin-(4beta->8)-epicatechin-3-O-gallic acid ester	Generator
Epigallocatechin-(4β->8)-epicatechin-3-O-gallate ester	Generator
Epigallocatechin-(4β->8)-epicatechin-3-O-gallic acid ester	Generator
Epigallocatechin-(4b->8)-epicatechin 3'-gallate	Generator
Epigallocatechin-(4b->8)-epicatechin 3'-gallic acid	Generator
Epigallocatechin-(4beta->8)-epicatechin 3'-gallic acid	Generator
Epigallocatechin-(4β->8)-epicatechin 3'-gallate	Generator
Epigallocatechin-(4β->8)-epicatechin 3'-gallic acid	Generator

Chemical Formula

C₃₇H₃₀O₁₇

Average Molecular Weight

746.63

Monoisotopic Molecular Weight

746.148299506

IUPAC Name

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

Traditional Name

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

CAS Registry Number

126715-82-0

SMILES

O[C@H]1[C@H](OC2=C([C@@H]1C1=C(O)C=C(O)C3=C1O[C@@H]([C@@H](C3)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(O)=CC(O)=C2)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C37H30O17/c38-15-8-20(42)28-26(9-15)52-35(13-4-22(44)31(48)23(45)5-13)33(50)30(28)29-21(43)11-18(40)16-10-27(53-37(51)14-6-24(46)32(49)25(47)7-14)34(54-36(16)29)12-1-2-17(39)19(41)3-12/h1-9,11,27,30,33-35,38-50H,10H2/t27-,30-,33-,34-,35-/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

proanthocyanidin (CHEBI:4807 )
Proanthocyanidins (C10223 )
Condensed tannins (Proanthocyanidins) (C10223 )
Proanthocyanidins (LMPK12030008 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037650)

Cellular substructure

Membrane (HMDB: HMDB0037650)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037650)

Source

Exogenous

Food

Food (HMDB: HMDB0037650)

Tea

Endogenous

Plant

Plant (HMDB: HMDB0037650)

Not Available

Nutrient (HMDB: HMDB0037650)

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	0.11 g/L	ALOGPS
logP	3.21	ALOGPS
logP	4.4	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	307.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	184.25 m³·mol⁻¹	ChemAxon
Polarizability	71.24 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
DeepCCS	[M+H]+	250.069	30932474
DeepCCS	[M-H]-	248.173	30932474
DeepCCS	[M-2H]-	282.2	30932474
DeepCCS	[M+Na]+	256.22	30932474
AllCCS	[M+H]+	262.3	32859911
AllCCS	[M+H-H2O]+	261.6	32859911
AllCCS	[M+NH4]+	262.8	32859911
AllCCS	[M+Na]+	263.0	32859911
AllCCS	[M-H]-	260.2	32859911
AllCCS	[M+Na-2H]-	263.5	32859911
AllCCS	[M+HCOO]-	267.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate	O[C@H]1[C@H](OC2=C([C@@H]1C1=C(O)C=C(O)C3=C1O[C@@H]([C@@H](C3)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(O)=CC(O)=C2)C1=CC(O)=C(O)C(O)=C1	9412.1	Standard polar	33892256
Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate	O[C@H]1[C@H](OC2=C([C@@H]1C1=C(O)C=C(O)C3=C1O[C@@H]([C@@H](C3)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(O)=CC(O)=C2)C1=CC(O)=C(O)C(O)=C1	6201.6	Standard non polar	33892256
Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate	O[C@H]1[C@H](OC2=C([C@@H]1C1=C(O)C=C(O)C3=C1O[C@@H]([C@@H](C3)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(O)=CC(O)=C2)C1=CC(O)=C(O)C(O)=C1	7413.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_1_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 10V, Positive-QTOF	splash10-002g-0500940600-f890cc25d2d93e71e4da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 20V, Positive-QTOF	splash10-0kbr-0962621000-937983ab06b23bf69ae9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 40V, Positive-QTOF	splash10-0pb9-0691000000-7502defb3d188a39fe24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 10V, Negative-QTOF	splash10-0002-0300111900-6c89ffa57f657fd3dffb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 20V, Negative-QTOF	splash10-0gb9-0914202200-36a55a42a503069c0e9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 40V, Negative-QTOF	splash10-004i-0901000000-f39354ee36147f60cf68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 10V, Negative-QTOF	splash10-002b-0000070900-df0f0f53fd872f682c62	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 20V, Negative-QTOF	splash10-0fvj-0900038700-b81b0f6bdfaf188846c8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 40V, Negative-QTOF	splash10-00p3-0911404300-9fdc79cc26555c4b36b4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 10V, Positive-QTOF	splash10-002b-0110344900-1d73ec93c53526d32c84	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 20V, Positive-QTOF	splash10-0ffw-0930416800-eced173636d46e985be5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 40V, Positive-QTOF	splash10-0f7a-0720938200-f1e154215093e560de3b	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442678

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 Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate (HMDB0037650)

MOL for HMDB0037650 (Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate)

3D MOL for HMDB0037650 (Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate)

3D SDF for HMDB0037650 (Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate)

3D-SDF for HMDB0037650 (Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate)

PDB for HMDB0037650 (Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate)

3D PDB for HMDB0037650 (Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate)

SMILES for HMDB0037650 (Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate)

INCHI for HMDB0037650 (Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate)

Structure for HMDB0037650 (Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate)

3D Structure for HMDB0037650 (Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra